Compound (I)

文档序号：90666 发布日期：2021-10-08 浏览：44次中文

阅读说明：本技术 化合物 (Compound (I) ) 是由浅津悠司小泽昭一小桥亚依于 2020-02-21 设计创作，主要内容包括：分子量为3000以下且具有式(X)所示的局部结构的化合物。式(X)中,环W～(1)表示具有至少1个双键作为环的构成要素且不具有芳香族性的环结构。R～(3)表示杂环基、卤素原子、硝基、氰基、羟基、巯基、羧基、－SF-5、－SF-3、－SO-3H、－SO-2H、任选具有取代基的碳数1～25的脂肪族烃基或者任选具有取代基的碳数为6～18的芳香族烃基。(A compound having a molecular weight of 3000 or less and having a partial structure represented by formula (X). In the formula (X), ring W 1 Represents a ring structure having at least 1 double bond as a ring constituent and having no aromatic character. R 3 Represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF 5 、－SF 3 、－SO 3 H、－SO 2 H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.)

1. A compound having a molecular weight of 3000 or less and a partial structure represented by the formula (X),

in the formula (X), ring W¹Represents a ring structure having at least 1 double bond as a constituent of the ring and having no aromatic character,

R³represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－、－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－，

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10AAnd R^11AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

2. The compound of claim 1, wherein,

the compound having a molecular weight of 3000 or less and a partial structure represented by formula (X) is any of a compound represented by formula (I) to a compound represented by formula (VIII),

in the formulae (I) to (VIII),

ring W¹And R³Are meant to have the same meaning as above,

ring W²Ring W³Ring W⁴Ring W⁵Ring W⁶Ring W⁷Ring W⁸Ring W⁹Ring W¹⁰Ring W¹¹And a ring W¹²Each independently represents a ring structure having at least 1 double bond as a constituent of the ring,

ring W¹¹¹Represents a ring having at least 2 nitrogen atoms as a constituent,

ring W¹¹²And a ring W¹¹³Each independently represents a ring having at least 1 nitrogen atom as a constituent,

R¹、R⁴¹、R⁵¹、R⁶¹、R⁹¹、R¹⁰¹、R¹¹¹、R²、R¹²、R⁴²、R⁵²、R⁶²、R⁷²、R⁸²、R⁹²、R¹⁰²and R¹¹²Each independently represents a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH is optionally substituted by-NR^12A－、－SO₂－、－CO－、－O－、－COO－、－OCO－、－CONR^13A－、－NR^14A－CO－、－S－、－SO－、－CF₂-or-CHF-,

R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³and R¹¹³Each independently represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group or-SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A－CS－S－、－S－CS－、－CS－S－、—S－CS-S-, -SO-or-SO₂—，

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10A、R^11A、R^12A、R^13AAnd R^14AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

R⁴、R¹⁴、R²⁴、R³⁴、R⁴⁴、R⁵⁴、R⁶⁴、R⁷⁴、R⁸⁴、R⁹⁴、R¹⁰⁴、R¹¹⁴、R⁵、R¹⁵、R²⁵、R³⁵、R⁷⁵and R⁸⁵Each independently represents an electron withdrawing group,

R¹and R²Optionally bonded to each other to form a ring,

R⁴¹and R⁴²Optionally bonded to each other to form a ring,

R⁵¹and R⁵²Optionally bonded to each other to form a ring,

R⁶¹and R⁶²Optionally bonded to each other to form a ring,

R⁹¹and R⁹²Optionally bonded to each other to form a ring,

R¹⁰¹and R¹⁰²Optionally bonded to each other to form a ring,

R¹¹¹and R¹¹²Optionally bonded to each other to form a ring,

R²and R³Optionally bonded to each other to form a ring,

R¹²and R¹³Optionally bonded to each other to form a ring,

R⁴²and R⁴³Optionally bonded to each other to form a ring,

R⁵²and R⁵³Optionally bonded to each other to form a ring,

R⁶²and R⁶³Optionally bonded to each other to form a ring,

R⁷²and R⁷³Optionally bonded to each other to form a ring,

R⁸²and R⁸³Optionally bonded to each other to form a ring,

R⁹²and R⁹³Optionally bonded to each other to form a ring,

R¹⁰²and R¹⁰³Optionally bonded to each other to form a ring,

R¹¹²and R¹¹³Optionally bonded to each other to form a ring,

R⁴and R⁵Optionally bonded to each other to form a ring,

R¹⁴and R¹⁵Optionally bonded to each other to form a ring,

R²⁴and R²⁵Optionally bonded to each other to form a ring,

R³⁴and R³⁵Optionally bonded to each other to form a ring,

R⁷⁴and R⁷⁵Optionally bonded to each other to form a ring,

R⁸⁴and R⁸⁵Optionally bonded to each other to form a ring,

R⁶and R⁸Each independently represents a divalent linking group,

R⁷represents a single bond or a divalent linking group,

R⁹and R¹⁰Each independently represents a trivalent linking group,

R¹¹represents a tetravalent linker.

3. The compound of claim 2, wherein R is selected from⁴And R⁵At least one of which is nitro, cyano, a halogen atom, -OCF₃、－SCF₃、－SF₅、－SF₃Fluoroalkyl, fluoroaryl, -CO-O-R²²²、－SO₂—R²²²or-CO-R²²²，

R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.

4. The compound of claim 2 or 3,

is selected from R⁴And R⁵At least one of which is nitro, cyano, fluorine atom, chlorine atom, -OCF₃、－SCF₃Fluoroalkyl, -CO-O-R²²²or-SO₂—R²²²，

R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.

5. The compound according to any one of claims 2 to 4,

is selected from R⁴And R⁵At least one of which is cyano, -CO-O-R²²²or-SO₂—R²²²，

R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.

6. The compound according to any one of claims 2 to 5,

is selected from R⁴And R⁵At least one of which is cyano.

7. The compound according to any one of claims 2 to 6,

R⁴is a cyano group, and is a cyano group,

R⁵is cyano, -CO-O-R²²²or-SO₂－R²²²，

R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.

8. The compound according to any one of claims 2 to 7,

R⁴and R⁵Are all cyano groups.

9. The compound according to any one of claims 2 to 8,

R¹and R²Each independently is an optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms.

10. The compound according to any one of claims 2 to 8,

R¹and R²Are connected to each other to form a ring.

11. The compound of claim 10, wherein,

R¹and R²The rings formed by the mutual connection are alicyclic rings.

12. The compound according to any one of claims 2 to 11,

ring W²Ring W³Ring W⁴Ring W⁵Ring W⁶Ring W⁷Ring W⁸Ring W⁹Ring W¹⁰Ring W¹¹And a ring W¹²Each independently is a ring having no aromatic character.

13. The compound according to any one of claims 2 to 12,

ring W²Ring W³Ring W⁴Ring W⁵Ring W⁶Ring W⁷Ring W⁸Ring W⁹Ring W¹⁰Ring W¹¹And a ring W¹²Each independently a five-to seven-membered ring structure.

14. The compound of claim 13, wherein,

ring W²Ring W³Ring W⁴Ring W⁵Ring W⁶Ring W⁷Ring W⁸Ring W⁹Ring W¹⁰Ring W¹¹And a ring W¹²Each independently is a six-membered ring structure.

15. The compound according to any one of claims 1 to 14,

R³is nitro, cyano, halogen, -OCF₃、－SCF₃、－SF₅、－SF₃Fluoroalkyl, fluoroaryl, -CO-O-R^111Aor-SO₂－R^112A，

R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom.

16. The compound according to any one of claims 1 to 15,

R³is cyano, fluorine, chlorine, -OCF₃、－SCF₃Fluoroalkyl, -CO-O-R^111Aor-SO₂－R^112A，

R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom.

17. The compound according to any one of claims 1 to 16,

R³is cyano.

18. The compound according to any one of claims 1 to 17,

ring W¹Is a five-seven membered ring.

19. The compound of claim 18, wherein,

ring W¹Is a six-membered ring.

20. The compound according to any one of claims 1 to 19,

the molar absorptivity epsilon at lambda max is more than 0.5,

λ max represents a maximum absorption wavelength of a compound having a molecular weight of 3000 or less and having a local structure represented by formula (X), the unit of the maximum absorption wavelength being nm.

21. The compound according to any one of claims 1 to 20,

which satisfies the formula (B),

ε(λmax)/ε(λmax+30nm)≥5 (B)

ε (λ max) represents an molar absorption coefficient at the maximum absorption wavelength of a compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X),

ε (λ max +30nm) represents an molar absorption coefficient at a wavelength (maximum absorption wavelength +30nm) of a compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X),

the units of the maximum absorption wavelength and the wavelength of (maximum absorption wavelength +30nm) are nm.

22. A composition comprising a compound of any one of claims 1-21.

23. A shaped article formed from the composition of claim 22.

24. A composition for an eyeglass lens, comprising the compound according to any one of claims 1 to 21.

25. An eyeglass lens formed from the composition for an eyeglass lens of claim 24.

26. A method for producing a compound represented by the formula (I), which comprises a step of reacting a compound represented by the formula (I-1) with a compound represented by the formula (I-2),

in the formula (I-1),

ring W¹Represents a ring structure having at least 1 double bond as a constituent of the ring and having no aromatic character,

R¹and R²Each independently represents a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH is optionally substituted by-NR^12A－、－SO₂－、－CO－、－O－、－COO－、－OCO－、－CONR^13A－、－NR^14A－CO－、－S－、－SO－、－CF₂-or-CHF-,

R¹and R²Optionally linked to each other to form a ring,

R³represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－，

R²And R³Optionally bonded to each other to form a ring,

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10A、R^11A、R^12A、R^13Aand R^14AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

in the formula (I-2), R⁴And R⁵Each independently represents an electron withdrawing group, R⁴And R⁵Optionally bonded to each other to form a ring,

in the formula (I), ring W¹、R¹、R²、R³、R⁴And R⁵The same meaning as above is indicated.

27. The production process according to claim 26, further comprising a step of reacting the compound represented by the formula (I-3) with the compound represented by the formula (I-4) to obtain a compound represented by the formula (I-1),

in the formula (I-3), ring W¹、R¹And R²Are meant to have the same meaning as above,

R³-E₁ (I-4)

in the formula (I-4), R³Denotes the same meaning as above, E₁Represents a leaving group.

28. The production method according to claim 27, further comprising a step of reacting the compound represented by the formula (I-5) with the compound represented by the formula (I-6) to obtain a compound represented by the formula (I-3),

in the formula (I-5), ring W¹Are meant to have the same meaning as above,

in the formula (I-6), R¹And R²The same meaning as above is indicated.

29. A method for producing a compound represented by the formula (I), which comprises a step of reacting a compound represented by the formula (I-7) with a compound represented by the formula (I-6),

in the formula (I-7),

ring W¹Represents a ring structure having at least 1 double bond as a constituent of the ring and having no aromatic character,

R³represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－，

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10AAnd R^11AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

R⁴and R⁵Each independently represents an electron withdrawing group,

R⁴and R⁵Optionally bonded to each other to form a ring,

in the formula (I-6),

R¹and R²Each independently represents a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH is optionally substituted by-NR^12A－、－SO₂－、－CO－、－O－、－COO－、－OCO－、－CONR^13A－、－N^14A－CO－、－S－、－SO－、－SO₂－、－CF₂-or-CHF-,

R¹and R²Optionally linked to each other to form a ring,

R^12A、R^13Aand R^14AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

in the formula (I), the compound is shown in the specification,ring W¹、R¹、R²、R³、R⁴And R⁵Denotes the same meaning as above, R²And R³Optionally bonded to each other to form a ring.

30. The production process according to claim 29, further comprising a step of reacting the compound represented by the formula (I-8) with the compound represented by the formula (I-4) to obtain a compound represented by the formula (I-7),

in the formula (I-8), ring W¹、R⁴And R⁵Are meant to have the same meaning as above,

R³-E₁ (I-4)

in the formula (I-4), R³Denotes the same meaning as above, E₁Represents a leaving group.

31. The production process according to claim 30, further comprising a step of reacting the compound represented by the formula (I-5) with the compound represented by the formula (I-2) to obtain a compound represented by the formula (I-8),

in the formula (I-5), ring W¹Are meant to have the same meaning as above,

in the formula (I-2), R⁴And R⁵The same meaning as above is indicated.

32. The production process according to claim 26, further comprising a step of reacting the compound represented by the formula (I-5-1) with the compound represented by the formula (I-6) to obtain a compound represented by the formula (I-1),

in the formula (I-5-1), the ring W¹And R³Are meant to have the same meaning as above,

in the formula (I-6), R¹And R²The same meaning as above is indicated.

33. The production process according to claim 29, further comprising a step of reacting the compound represented by the formula (I-5-1) with the compound represented by the formula (I-2) to obtain a compound represented by the formula (I-7),

in the formula (I-5-1), the ring W¹And R³Are meant to have the same meaning as above,

in the formula (I-2), R⁴And R⁵The same meaning as above is indicated.

34. The production method according to claim 32 or 33, further comprising a step of reacting the compound represented by the formula (I-5) with the compound represented by the formula (I-4) to obtain a compound represented by the formula (I-5-1),

in the formula (I-5), ring W¹Are meant to have the same meaning as above,

R³-E₁ (I-4)

in the formula (I-4), R³Denotes the same meaning as above, E₁Represents a leaving group.

Technical Field

The present invention relates to compounds.

Background

Conventionally, ultraviolet absorbers have been used in various applications and products in order to protect human bodies and resin materials from deterioration due to ultraviolet rays. Ultraviolet absorbers are broadly classified into inorganic ultraviolet absorbers and organic absorbers. Inorganic ultraviolet absorbers have good durability such as light resistance and heat resistance, and tend to be poor in control of absorption wavelength and compatibility with organic materials. On the other hand, although organic ultraviolet absorbers are inferior to inorganic ultraviolet absorbers in durability, they can control absorption wavelength, compatibility with organic materials, and the like in view of the degree of freedom of molecular structures in organic ultraviolet absorbers, and are used in a wide range of fields such as sunscreen, coating materials, optical materials, building materials, and automobile materials.

Examples of the organic ultraviolet absorber generally include compounds having a triazole skeleton, a benzophenone skeleton, a triazine skeleton, and a cyanoacrylate skeleton. However, most organic ultraviolet absorbers having the above-mentioned skeleton have a maximum absorption wavelength (λ max) of 360nm or less, and therefore cannot efficiently absorb ultraviolet to near ultraviolet regions having wavelengths of 380 to 400nm, and a very large amount of the organic ultraviolet absorbers is required to sufficiently absorb light in the region. Many of the compounds having the above skeleton have a broad absorption spectrum, and if light having a wavelength of 380 to 400nm is sufficiently absorbed, there is a problem that light having a wavelength of 420nm or more is also absorbed not only in a wavelength region of 380 to 400nm, and a composition containing an ultraviolet absorber is colored.

As a means for solving the above problems, for example, patent document 1 proposes a compound having a merocyanine skeleton represented by the following formula as an organic ultraviolet absorber. Patent document 1 describes that a film containing a compound having a merocyanine skeleton represented by the following formula has low light transmittance at a wavelength of around 390 nm.

Documents of the prior art

Patent document

Patent document 1: japanese patent laid-open publication No. 2010-111823

Disclosure of Invention

Problems to be solved by the invention

However, the compounds having a merocyanine skeleton have low durability (particularly, weather resistance), and are difficult to be applied to applications requiring severe weather resistance.

The purpose of the present invention is to provide a novel compound having a merocyanine skeleton which efficiently absorbs light having a wavelength of 380 to 400nm and can be used as an ultraviolet-near ultraviolet absorber having excellent weather resistance.

Means for solving the problems

The present invention includes the following inventions.

[1] A compound having a molecular weight of 3000 or less and having a partial structure represented by the formula (X).

[ in the formula (X), the ring W¹Is represented by having at least1 double bond is a constituent of a ring and has no aromatic ring structure.

R³Represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－、－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－。

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10AAnd R^11AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

[2] The compound according to [1], wherein the compound having a molecular weight of 3000 or less and a partial structure represented by the formula (X) is any one of a compound represented by the formula (I) to a compound represented by the formula (VIII).

[ formulae (I) to (VIII),

ring W¹And R³The same meaning as above is indicated.

Ring W²Ring W³Ring W⁴Ring W⁵Ring W⁶Ring W⁷Ring W⁸Ring W⁹Ring W¹⁰Ring W¹¹And a ring W¹²Each independently represents a ring structure having at least 1 double bond as a constituent of the ring.

Ring W¹¹¹Represents a ring having at least 2 nitrogen atoms as a constituent.

Ring W¹¹²And a ring W¹¹³Each independently represents a ring having at least 1 nitrogen atom as a constituent.

R¹、R⁴¹、R⁵¹、R⁶¹、R⁹¹、R¹⁰¹、R¹¹¹、R²、R¹²、R⁴²、R⁵²、R⁶²、R⁷²、R⁸²、R⁹²、R¹⁰²And R¹¹²Each independently represents a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH is optionally substituted by-NR^12A－、－SO₂－、－CO－、－O－、－COO－、－OCO－、－CONR^13A－、－NR^14A－CO－、－S－、－SO－、－CF₂-or-CHF-.

R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³And R¹¹³Each independently represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group or-SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms orAn aromatic hydrocarbon group having 6 to 18 carbon atoms and optionally a substituent, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－。

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10A、R^11A、R^12A、R^13AAnd R^14AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

R⁴、R¹⁴、R²⁴、R³⁴、R⁴⁴、R⁵⁴、R⁶⁴、R⁷⁴、R⁸⁴、R⁹⁴、R¹⁰⁴、R¹¹⁴、R⁵、R¹⁵、R²⁵、R³⁵、R⁷⁵And R⁸⁵Each independently represents an electron withdrawing group.

R¹And R²Optionally bonded to each other to form a ring.

R⁴¹And R⁴²Optionally bonded to each other to form a ring.

R⁵¹And R⁵²Optionally bonded to each other to form a ring.

R⁶¹And R⁶²Optionally bonded to each other to form a ring.

R⁹¹And R⁹²Optionally bonded to each other to form a ring.

R¹⁰¹And R¹⁰²Optionally bonded to each other to form a ring.

R¹¹¹And R¹¹²Optionally bonded to each other to form a ring.

R²And R³Optionally bonded to each other to form a ring.

R¹²And R¹³Optionally bonded to each other to form a ring.

R⁴²And R⁴³Optionally bonded to each other to form a ring.

R⁵²And R⁵³Optionally bonded to each other to form a ring.

R⁶²And R⁶³Optionally bonded to each other to form a ring.

R⁷²And R⁷³Optionally bonded to each other to form a ring.

R⁸²And R⁸³Optionally bonded to each other to form a ring.

R⁹²And R⁹³Optionally bonded to each other to form a ring.

R¹⁰²And R¹⁰³Optionally bonded to each other to form a ring.

R¹¹²And R¹¹³Optionally bonded to each other to form a ring.

R⁴And R⁵Optionally bonded to each other to form a ring.

R¹⁴And R¹⁵Optionally bonded to each other to form a ring.

R²⁴And R²⁵Optionally bonded to each other to form a ring.

R³⁴And R³⁵Optionally bonded to each other to form a ring.

R⁷⁴And R⁷⁵Optionally bonded to each other to form a ring.

R⁸⁴And R⁸⁵Optionally bonded to each other to form a ring.

R⁶And R⁸Each independently represents a divalent linking group.

R⁷Represents a single bond or a divalent linking group.

R⁹And R¹⁰Each independently represents a trivalent linking group.

R¹¹To representA tetravalent linker.]

[3]Such as [2]]The compound of (A) wherein R is selected from⁴And R⁵At least one of which is nitro, cyano, a halogen atom, -OCF₃、－SCF₃、－SF₅、－SF₃Fluoroalkyl, fluoroaryl, -CO-O-R²²²、－SO₂－R²²²or-CO-R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms).

[4]Such as [2]]Or [ 3]]The compound of (A) wherein R is selected from⁴And R⁵At least one of which is nitro, cyano, fluorine atom, chlorine atom, -OCF₃、－SCF₃Fluoroalkyl, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms).

[5]Such as [2]]～[4]The compound of any one of (1) above, wherein R is selected from⁴And R⁵At least one of which is cyano, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms).

[6]Such as [2]]～[5]The compound of any one of (1) above, wherein R is selected from⁴And R⁵At least one of which is cyano.

[7]Such as [2]]～[6]The compound of any one of (1), wherein R⁴Is a cyano group, and is a cyano group,

R⁵is cyano, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms).

[8]Such as [2]]～[7]The compound of any one of (1), wherein R⁴And R⁵Are all cyano groups.

[9]Such as [2]]～[8]The compound of any one of (1), wherein R¹And R²Each independently is an optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms.

[10]Such as [2]]～[8]The compound of any one of (1), wherein R¹And R²Are connected to each other to form a ring.

[11]Such as [10 ]]The compound of (1), wherein R¹And R²The rings formed by the mutual connection are alicyclic rings.

[12]Such as [2]]～[11]The compound of any one of, wherein, ring W²Ring W³Ring W⁴Ring W⁵Ring W⁶Ring W⁷Ring W⁸Ring W⁹Ring W¹⁰Ring W¹¹And a ring W¹²Each independently is a ring having no aromatic character.

[13]Such as [2]]～[12]The compound of any one of, wherein, ring W²Ring W³Ring W⁴Ring W⁵Ring W⁶Ring W⁷Ring W⁸Ring W⁹Ring W¹⁰Ring W¹¹And a ring W¹²Each independently a five-to seven-membered ring structure.

[14]Such as [13 ]]The compound of (1), wherein, ring W²Ring W³Ring W⁴Ring W⁵Ring W⁶Ring W⁷Ring W⁸Ring W⁹Ring W¹⁰Ring W¹¹And a ring W¹²Each independently is a six-membered ring structure.

[15]Such as [1]]～[14]The compound of any one of (1), wherein R³Is nitro, cyano, halogen, -OCF₃、－SCF₃、－SF₅、－SF₃Fluoroalkyl, fluoroaryl, -CO-O-R^111Aor-SO₂－R^112A(R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom).

[16]Such as [1]]～[15]The compound of any one of (1), wherein R³Is cyano, fluorine, chlorine, -OCF₃、－SCF₃Fluoroalkyl, -CO-O-R^111Aor-SO₂－R^112A(R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom).

[17]Such as [1]]～[16]The compound of any one of (1), wherein R³Is cyano.

[18]Such as [1]]～[17]The compound of any one of, wherein, ring W¹Is a five-seven membered ring.

[19]Such as [18 ]]The compound of (1), wherein, ring W¹Is a six-membered ring.

[20] The compound according to any one of [1] to [19], which has a molar absorption coefficient ε at λ max of 0.5 or more.

(λ max represents a maximum absorption wavelength [ nm ] of a compound having a molecular weight of 3000 or less and a partial structure represented by the formula (X))

[21] The compound according to any one of [1] to [20], which satisfies the formula (B).

ε(λmax)/ε(λmax+30nm)≥5(B)

[ ε (λ max) represents the molar absorption coefficient at the maximum absorption wavelength [ nm ] of a compound having a molecular weight of 3000 or less and a partial structure represented by formula (X).

ε (λ max +30nm) represents a molar absorption coefficient at a wavelength [ nm ] (maximum absorption wavelength +30nm) of a compound having a molecular weight of 3000 or less and a partial structure represented by the formula (X). ]

[22] A composition comprising the compound according to any one of [1] to [21 ].

[23] A molded article formed from the composition containing a compound according to [22 ].

[24] A composition for an eyeglass lens, comprising the compound according to any one of [1] to [21 ].

[25] An eyeglass lens formed from the composition for an eyeglass lens according to [24 ].

[26] A method for producing a compound represented by the formula (I), which comprises a step of reacting a compound represented by the formula (I-1) with a compound represented by the formula (I-2).

[ in the formula (I-1),

ring W¹Represents a ring structure having at least 1 double bond as a ring constituent and having no aromatic character.

R¹And R²Each independently represents a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH is optionally substituted by-NR^12A－、－SO₂－、－CO－、－O－、－COO－、－OCO－、－CONR^13A－、－NR^14A－CO－、－S－、－SO－、－CF₂-or-CHF-.

R¹And R²Optionally joined to each other to form a ring.

R³Represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－。

R²And R³Optionally bonded to each other to form a ring.

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10A、R^11A、R^12A、R^13AAnd R^14AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

[ in the formula (I-2), R⁴And R⁵Each independently represents an electron withdrawing group. R⁴And R⁵Optionally bonded to each other to form a ring.]

[ in the formula (I), the ring W¹、R¹、R²、R³、R⁴And R⁵The same meaning as above is indicated.]

[27] The production method according to [26], further comprising a step of reacting the compound represented by the formula (I-3) with the compound represented by the formula (I-4) to obtain the compound represented by the formula (I-1).

[ in the formula (I-3), the ring W¹、R¹And R²The same meaning as above is indicated.]

R³-E₁ (I-4)

[ in the formula (I-4), R³The same meaning as above is indicated. E₁Represents a leaving group.]

[28] The production method according to [27], further comprising a step of reacting the compound represented by the formula (I-5) with the compound represented by the formula (I-6) to obtain the compound represented by the formula (I-3).

[ in the formula (I-5), the ring W¹The same meaning as above is indicated.]

[ in the formula (I-6), R¹And R²The same meaning as above is indicated.]

[29] A method for producing a compound represented by the formula (I), which comprises a step of reacting a compound represented by the formula (I-7) with a compound represented by the formula (I-6).

[ in the formula (I-7),

ring W¹Represents a ring structure having at least 1 double bond as a ring constituent and having no aromatic character.

R³Represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－。

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10AAnd R^11AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

R⁴And R⁵Each independently represents an electron withdrawing group.

R⁴And R⁵Optionally bonded to each other to form a ring.]

[ in the formula (I-6),

R¹and R²Each independently represents a hydrogen atom, a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group, -SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH is optionally substituted by-NR^12A－、－SO₂－、－CO－、－O－、－COO－、－OCO－、－CONR^13A－、－N^14A－CO－、－S－、－SO－、－SO₂－、－CF₂-or-CHF-.

R¹And R²Optionally joined to each other to form a ring.

R^12A、R^13AAnd R^14AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

[ in the formula (I), the ring W¹、R¹、R²、R³、R⁴And R⁵The same meaning as above is indicated. R²And R³Optionally bonded to each other to form a ring.]

[30] The production method according to [29], further comprising a step of reacting the compound represented by the formula (I-8) with the compound represented by the formula (I-4) to obtain a compound represented by the formula (I-7).

[ in the formula (I-8), the ring W¹、R⁴And R⁵The same meaning as above is indicated.]

R³-E₁ (I-4)

[ in the formula (I-4), R³The same meaning as above is indicated. E₁Represents a leaving group.]

[31] The production method according to [30], further comprising a step of reacting the compound represented by the formula (I-5) with the compound represented by the formula (I-2) to obtain a compound represented by the formula (I-8).

[ in the formula (I-5), the ring W¹The same meaning as above is indicated.]

[ in the formula (I-2), R⁴And R⁵The same meaning as above is indicated.]

[32] The production method according to [26], further comprising a step of reacting the compound represented by the formula (I-5-1) with the compound represented by the formula (I-6) to obtain the compound represented by the formula (I-1).

[ in the formula (I-5-1), the ring W¹And R³The same meaning as above is indicated.]

[ in the formula (I-6), R¹And R²The same meaning as above is indicated.]

[33] The production method according to [29], which further comprises a step of obtaining a compound represented by the formula (I-7) by reacting the compound represented by the formula (I-5-1) with the compound represented by the formula (I-2).

[ in the formula (I-5-1), the ring W¹And R³The same meaning as above is indicated.]

[ in the formula (I-2), R⁴And R⁵The same meaning as above is indicated.]

[34] The production method according to [32] or [33], further comprising a step of reacting the compound represented by the formula (I-5) with the compound represented by the formula (I-4) to obtain the compound represented by the formula (I-5-1).

[ in the formula (I-5), the ring W¹The same meaning as above is indicated.]

R³-E₁ (I-4)

[ in the formula (I-4), R³The same meaning as above is indicated. E₁Represents a leaving group.]

ADVANTAGEOUS EFFECTS OF INVENTION

The present invention provides a novel compound having a merocyanine skeleton, which has high absorption selectivity for short-wavelength visible light having a wavelength of 380 to 400 nm. In addition, the compounds of the present invention have good weatherability.

Detailed Description

< Compound (X) >

The compound of the present invention is a compound having a molecular weight of 3000 or less and a partial structure represented by formula (X) (hereinafter, sometimes referred to as compound (X)).

[ in the formula (X), the ring W¹Represents a ring structure having at least 1 double bond as a ring constituent and having no aromatic character.

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10AAnd R^11AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.]

In the present specification, the carbon number does not include the carbon number of the substituent at-CH₂When — or — CH is substituted as described above, for example, it refers to the number of carbons before substitution.

Ring W¹The ring is not particularly limited as long as it has 1 or more double bonds as a constituent of the ring and is not aromatic. Ring W¹May be a single ring or a condensed ring.

Ring W¹The heterocyclic ring may have a hetero atom (for example, an oxygen atom, a sulfur atom, a nitrogen atom, or the like) as a constituent element of the ring, or may be an aliphatic hydrocarbon ring formed of a carbon atom and a hydrogen atom.

Ring W¹Having 1 or more double bonds as a constituent of the ring, ring W¹The number of double bonds contained in (1) is usually 1 to 4, preferably 1 to 3, more preferably 1 or 2, and still more preferably 1.

Ring W¹The ring is usually a ring having 5 to 18 carbon atoms, preferably a five-to seven-membered ring structure, and more preferably a six-membered ring structure.

Ring W¹Preferably a single ring.

Ring W¹Optionally having a substituent. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; alkyl groups having 1 to 12 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and the like; a halogenated alkyl group having 1 to 12 carbon atoms such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2-fluoroethyl group, a2, 2-difluoroethyl group, a2, 2, 2-trifluoroethyl group, a1, 1, 2, 2-tetrafluoroethyl group, a1, 1, 2, 2, 2-pentafluoroethyl group and the like; alkoxy having 1 to 12 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, etc.; alkylthio groups having 1 to 12 carbon atoms such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, and a hexylthio group; monofluoromethoxy, diA fluoroalkoxy group having 1 to 12 carbon atoms such as a fluoromethoxy group, a trifluoromethoxy group, a 2-fluoroethoxy group, a1, 1, 2, 2, 2-pentafluoroethoxy group, etc.; amino groups optionally substituted with an alkyl group having 1 to 6 carbon atoms, such as amino, methylamino, ethylamino, dimethylamino, diethylamino, or methylethylamino; an alkylcarbonyloxy group having 2 to 12 carbon atoms such as a methylcarbonyloxy group, an ethylcarbonyloxy group and the like; an alkylsulfonyl group having 1 to 12 carbon atoms such as a methylsulfonyl group and an ethylsulfonyl group; arylsulfonyl groups having 6 to 12 carbon atoms such as phenylsulfonyl groups; a cyano group; a nitro group; a hydroxyl group; a mercapto group; a carboxyl group; -SF₃；－SF₅And the like.

Ring W¹The optional substituent is preferably an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, or an amino group optionally substituted with an alkyl group having 1 to 6 carbon atoms.

As a ring W¹Examples thereof include the following groups.

[ in the formula, a1 represents a bond to a nitrogen atom, and a2 represents a bond to a carbon atom. ]

As R³Examples of the heterocyclic group include pyridyl, pyrrolidinyl, tetrahydrofurfuryl, tetrahydrothienyl, pyrrolyl, furyl, thienyl (Japanese: チオフェノ yl), piperidyl, tetrahydropyranyl, tetrahydrothiopyranyl, thiapyranyl, imidazolinyl (Japanese: イミダゾリノ yl), pyrazolyl, oxazolyl, thiazolyl, dioxanyl, morpholinyl, thiazinyl, triazolyl, tetrazolyl, dioxolanyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolyl, isoindolyl, benzimidazolyl, purinyl, benzotriazolyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, pteridinyl, benzopyranyl, anthracenyl, acridinyl, xanthenyl, and the likeAliphatic heterocyclic groups having 3 to 16 carbon atoms such as a pyridyl group, carbazolyl group, tetracenyl group, porphinyl group, chlorinyl group, corrin group, adenine group, guanine group, cytosine group, thymidylyl group, uracil group, quinolyl group, thienyl group, imidazolyl group, oxazolyl group, thiazolyl group and the like, and aromatic heterocyclic groups having 3 to 16 carbon atoms are preferably a pyrrolidinyl group, piperidyl group, tetrahydrofurfuryl group, tetrahydropyranyl group, tetrahydrothienyl group (Japanese: テトラヒドロチオフェノ group), tetrahydrothiopyranyl group or pyridyl group.

As R³Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms include: a straight-chain or branched alkyl group having 1 to 25 carbon atoms such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a sec-butyl group, a n-pentyl group, an isopentyl group, a n-hexyl group, an isohexyl group, a n-octyl group, an isooctyl group, a n-nonyl group, an isononyl group, a n-decyl group, an isodecyl group, a n-dodecyl group, an isododecyl group, an undecyl group, a lauryl group, a myristyl group, a cetyl group, a stearyl group, and the like: cycloalkyl groups having 3 to 25 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl; cycloalkyl alkyl group having 4 to 25 carbon atoms such as cyclohexylmethyl group, and the like.

R³The aliphatic hydrocarbon group having 1 to 25 carbon atoms is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 12 carbon atoms.

As R³Examples of the substituent optionally contained in the aliphatic hydrocarbon group include a halogen atom, a hydroxyl group, a nitro group, a cyano group and-SO₃H, and the like.

R³-CH contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A－CS－S－、－S－CS－、－CS－S-, -S-CS-S-, -SO-or-SO₂－。

-CH contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms₂when-or-CH-is substituted, it is preferably-O-, -S-, -CO-O-or-SO₂-a permutation.

-CH contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms₂When — or — CH is replaced with — O —, the aliphatic hydrocarbon group is preferably an alkoxy group represented by — O-R '(R' is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom). Further, a polyalkyleneoxy group such as a polyethyleneoxy group or a polypropyleneoxy group may be used. Examples of the alkoxy group represented by-O-R' include methoxy, ethoxy and-OCF₃And a poly (ethyleneoxy) group, a poly (propyleneoxy) group, and the like.

-CH contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms₂when-or-CH-is substituted by-S-, the aliphatic hydrocarbon group is preferably an alkylthio group represented by-S-R '(R' is an alkyl group having 1 to 24 carbon atoms which may have a halogen atom). Furthermore, a polyalkylenethiol group such as a polyethylenethio group or a polypropylenylthio group may be mentioned. Examples of the alkylthio group represented by-S-R' include a methylthio group, an ethylthio group and-SCF₃Poly (ethylenethio), poly (propylenylthio), and the like.

-CH contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms₂when-CH-is replaced by-COO-, the aliphatic hydrocarbon group is preferably a group represented by-COO-R '(R' is an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom).

-CH contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms₂-or-CH ═ by-SO₂In the case of substitution, the aliphatic hydrocarbon radical is preferably-SO₂R '(R' is an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom) and may be-SO₂CHF₂Radical, -SO₂CH₂F radicals and the like.

As R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10AAnd R^11AExamples of the alkyl group having 1 to 6 carbon atoms include straight-chain or branched-chain alkyl groups having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a sec-butyl group, a n-pentyl group, a n-hexyl group, and a 1-methylbutyl group.

As R³Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include phenyl, naphthyl, anthryl, tetracenyl, pentacenyl, phenanthryl, and the like,Radical, triphenylene radical, benzo [ a ]]Aryl groups having 6 to 18 carbon atoms such as an anthracenyl group (Japanese: テトラフェニル), a pyrenyl group, a perylene group, a coronene group (Japanese: コロネニル) and a biphenyl group; aralkyl group having 7 to 18 carbon atoms such as benzyl group, phenylethyl group, naphthylmethyl group and the like, preferably aryl group having 6 to 18 carbon atoms, more preferably phenyl group or benzyl group.

As R³Examples of the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms may optionally have include a halogen atom; a hydroxyl group; a mercapto group; an amino group; a nitro group; a cyano group; -SO₃H group, etc.

R³-CH contained in an aromatic hydrocarbon group having 6 to 18 carbon atoms₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－、－S－CO－S－、－S－CO－NR^8A－、-NR^9A-CO-S－、－CS－、-O－CS-、-CS-O-、-NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－。

-CH contained in the C6-18 aromatic hydrocarbon group₂when-or-CH-is substituted, it is preferably substituted by-O-or-SO₂-a permutation.

-CH contained in the C6-18 aromatic hydrocarbon group₂when-CH-is replaced by-O-, the aromatic hydrocarbon group is preferably an aryloxy group having 6 to 17 carbon atoms such as a phenoxy group; and aralkyloxy groups such as phenoxyethyl, phenoxydiethylene glycol, and phenoxypolyalkylene glycol.

-CH contained in the C6-18 aromatic hydrocarbon group₂-or-CH ═ by-SO₂In the case of substitution, the aromatic hydrocarbon group is preferably-SO₂-R "(R" represents an aryl group having 6 to 17 carbon atoms or an aralkyl group having 7 to 17 carbon atoms).

As R³Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

R³Preferably nitro; a cyano group; a halogen atom; -OCF₃；-SCF₃；－SF₅；－SF₃(ii) a A fluoroalkyl group (preferably having 1 to 25 carbon atoms); a fluorinated aryl group (preferably having 6 to 18 carbon atoms); -CO-O-R^111Aor-SO₂－R^112A(R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom. ),

more preferably a cyano group; a fluorine atom; a chlorine atom; -OCF₃；－SCF₃(ii) a A fluoroalkyl group (preferably having 1 to 12 carbon atoms); -CO-O-R^111Aor-SO₂－R^112A(R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom),

cyano is particularly preferred.

The molecular weight of the compound (X) is preferably 2500 or less, more preferably 2000 or less, still more preferably 1500 or less, and particularly preferably 1000 or less.

Further, it is preferably 100 or more, 150 or more, or 200 or more.

The compound (X) may be a copolymer as long as it has a molecular weight of 3000 or less, and is preferably a monomer.

The compound (X) preferably exhibits a maximum absorption wavelength at a wavelength of 370nm or more and 420nm or less. When the compound (X) exhibits a maximum absorption wavelength at a wavelength of 370nm or more and 420nm or less, ultraviolet to near ultraviolet light having a wavelength of 380nm or more and 400nm or less can be efficiently absorbed. The maximum absorption wavelength (λ max) of the compound (X) is preferably a wavelength of 375nm or more and 415nm or less, more preferably a wavelength of 375nm or more and 410nm or less, and further preferably a wavelength of 380nm or more and 400nm or less.

The compound (X) has a molar absorptivity ε at λ max of preferably 0.5 or more, more preferably 0.75 or more, and particularly preferably 1.0 or more. The upper limit is not particularly limited, but is generally 10 or less. λ max represents the maximum absorption wavelength of the compound (X).

When the molar absorptivity epsilon at lambda max of the compound (X) is 0.5 or more, even a small amount of the compound (X) can efficiently absorb ultraviolet to near ultraviolet light having a wavelength of 380 to 400 nm.

The compound (X) preferably has ε (λ max)/ε (λ max +30nm) of 5 or more, more preferably 10 or more, and particularly preferably 20 or more. The upper limit is not particularly limited, but is generally 1000 or less. ε (λ max) represents the molar absorption coefficient at the maximum absorption wavelength [ nm ] of the compound (X), and ε (λ max +30nm) represents the molar absorption coefficient at the wavelength [ nm ] (maximum absorption wavelength [ nm ] +30nm) of the compound (X).

When ∈ (λ max)/∈ (λ max +30nm) is 5 or more, the side absorption at a wavelength of 420nm or more can be minimized, and therefore coloration is less likely to occur.

The molar absorption coefficient is expressed in units of L/(g · cm).

The compound (X) is preferably any one of a compound represented by formula (I) to a compound represented by formula (VIII), and more preferably a compound represented by formula (I).

[ formulae (I) to (VIII),

ring W¹And R³The same meaning as above is indicated.

Ring W¹¹¹Represents a ring having at least 2 nitrogen atoms as a constituent.

Ring W¹¹²And a ring W¹¹³Each independently represents a ring having at least 1 nitrogen atom as a constituent.

R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³And R¹¹³Each independently represents a heterocyclic group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a mercapto group, a carboxyl group or-SF₅、－SF₃、－SO₃H、－SO₂H. An optionally substituted aliphatic hydrocarbon group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms, -CH contained in the aliphatic hydrocarbon group or the aromatic hydrocarbon group₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－。

R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10A、R^11A、R^12A、R^13AAnd R^14AEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

R¹And R²Optionally bonded to each other to form a ring.

R⁴¹And R⁴²Optionally bonded to each other to form a ring.

R⁵¹And R⁵²Optionally bonded to each other to form a ring.

R⁶¹And R⁶²Optionally bonded to each other to form a ring.

R⁹¹And R⁹²Optionally bonded to each other to form a ring.

R¹⁰¹And R¹⁰²Optionally bonded to each other to form a ring.

R¹¹¹And R¹¹²Optionally bonded to each other to form a ring.

R²And R³Optionally bonded to each other to form a ring.

R¹²And R¹³Optionally bonded to each other to form a ring.

R⁴²And R⁴³Optionally bonded to each other to form a ring.

R⁵²And R⁵³Optionally bonded to each other to form a ring.

R⁶²And R⁶³Optionally bonded to each other to form a ring.

R⁷²And R⁷³Optionally bonded to each other to form a ring.

R⁸²And R⁸³Optionally bonded to each other to form a ring.

R⁹²And R⁹³Optionally bonded to each other to form a ring.

R¹⁰²And R¹⁰³Optionally bonded to each other to form a ring.

R¹¹²And R¹¹³Optionally bonded to each other to form a ring.

R⁴And R⁵Optionally bonded to each other to form a ring.

R¹⁴And R¹⁵Optionally bonded to each other to form a ring.

R²⁴And R²⁵Optionally bonded to each other to form a ring.

R³⁴And R³⁵Optionally bonded to each other to form a ring.

R⁷⁴And R⁷⁵Optionally bonded to each other to form a ring.

R⁸⁴And R⁸⁵Optionally bonded to each other to form a ring.

R⁶And R⁸Each independently represents a divalent linking group.

R⁷Represents a single bond or a divalent linking group.

R⁹And R¹⁰Each independently represents a trivalent linking group.

R¹¹Represents a tetravalent linker.]

Ring W²Ring W³Ring W⁴Ring W⁵Ring W⁶Ring W⁷Ring W⁸Ring W⁹Ring W¹⁰Ring W¹¹And a ring W¹²Each independently is not particularly limited as long as it is a ring having 1 or more double bonds as a constituent of the ring. Ring W²Ring W¹²Each may be a monocyclic ring or a condensed ring. In addition, a ring W²Ring W¹²May be an aliphatic ring or an aromatic ring.

Ring W²Ring W¹²May be a heterocyclic ring containing a hetero atom (for example, an oxygen atom, a sulfur atom, a nitrogen atom, etc.) as a constituent element of the ring.

Ring W²Ring W¹²Having 1 or more double bonds as a constituent of the ring, ring W²Ring W¹²The number of double bonds contained in (a) is usually 1 to 4, preferably 1 to 3, more preferably 1 or 2, and further preferably 1.

Ring W²Ring W¹²Each independently is a ring having usually 5 to 18 carbon atoms, preferably a five-to seven-membered ring structure, and more preferably a six-membered ring structure.

Ring W²Ring W¹²Each independently is preferably a single ring. In addition, a ring W²Ring W¹²Each independently is preferably a ring having no aromatic character.

Ring W²Ring W¹²Optionally having a substituent. Examples of the substituent include a group bonded to the ring W¹And a group having the same substituent as the optional group.

As a ring W²Ring W¹²The optional substituent is preferably an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, or an amino group optionally substituted with an alkyl group having 1 to 6 carbon atoms.

As a ring W²Ring W¹²Specific examples of (3) include¹Tool (A)The same embodiment is exemplified.

Ring W¹¹¹Is a ring containing 2 nitrogen atoms as a constituent of the ring. Ring W¹¹¹The ring may be a single ring or a condensed ring, and is preferably a single ring.

Ring W¹¹¹Generally, it is a five-to ten-membered ring, preferably a five-to seven-membered ring, more preferably a five-or six-membered ring.

Ring W¹¹¹Optionally having a substituent. As a ring W¹¹¹Examples of the optional substituent include a hydroxyl group; a mercapto group; a formyl group; alkyl groups having 1 to 6 carbon atoms such as methyl group and ethyl group; alkoxy groups having 1 to 6 carbon atoms such as methoxy and ethoxy; alkylthio groups having 1 to 6 carbon atoms such as methylthio and ethylthio; amino groups optionally substituted with alkyl groups having 1 to 6 carbon atoms, such as amino, methylamino, dimethylamino, and methylethylamino; -CONR^1fR^2f(R^1fAnd R^2fEach independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ) (ii) a -COSR^3f(R^3fRepresents an alkyl group having 1 to 6 carbon atoms. ) (ii) a -CSSR^4f(R^4fRepresents an alkyl group having 1 to 6 carbon atoms. ) (ii) a -CSOR^5f(R^5fRepresents an alkyl group having 1 to 6 carbon atoms. ) (ii) a -SO₂R^6f(R^5fRepresents an aryl group having 6 to 12 carbon atoms or an alkyl group having 1 to 6 carbon atoms optionally having a fluorine atom. ) And the like.

As a ring W¹¹¹Examples thereof include the following rings.

Ring W¹¹²And a ring W¹¹³Each independently is a ring containing 1 nitrogen atom as a constituent of the ring. Ring W¹¹²And a ring W¹¹³Each independently may be a monocyclic ring or a fused ring, and is preferably a monocyclic ring.

Ring W¹¹²And a ring W¹¹³Each independently is typically a five to ten membered ring, preferably a five to seven membered ring, more preferably a five or six membered ring.

Ring W¹¹²And a ring W¹¹³Optionally having a substituent. As a ring W¹¹²And a ring W¹¹³Examples of the optionally substituted group include those related to the ring W¹The same substituents as in (1).

As a ring W¹¹²And a ring W¹¹³Examples thereof include the following rings.

As R⁴、R¹⁴、R²⁴、R³⁴、R⁴⁴、R⁵⁴、R⁶⁴、R⁷⁴、R⁸⁴、R⁹⁴、R¹⁰⁴、R¹¹⁴、R⁵、R¹⁵、R²⁵、R³⁵、R⁷⁵And R⁸⁵Examples of the electron-withdrawing group include a halogen atom, a nitro group, a cyano group, a carboxyl group, a haloalkyl group, a haloaryl group and-OCF₃、－SCF₃、－SF₅、-SF₃、－SO₃H、－SO₂H、－SO₂CF₃、－SO₂CHF₂、－SO₂CH₂F. A group represented by the formula (X-1).

*-X¹-R²²² (X-1)

[ in the formula (X-1),

X¹represents-CO-, -COO-, -OCO-, -CS-, -CSS-, -COS-, -CSO-, -SO₂－、－NR²²³CO-or-CONR²²⁴－。

R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms.

R²²³And R²²⁴Each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group.

Denotes a bond. ]

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of the haloalkyl group include fluoroalkyl groups such as a trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl group, and perfluorohexyl group, and a perfluoroalkyl group is preferable. The number of carbon atoms of the haloalkyl group is usually 1 to 25, preferably 1 to 12. The haloalkyl group may be linear or branched.

Examples of the halogenated aryl group include a fluorophenyl group, a chlorophenyl group, a bromophenyl group and the like, a fluorinated aryl group is preferable, and a perfluorinated aryl group is more preferable. The number of carbon atoms of the aryl group containing a halogen atom is usually 6 to 18, preferably 6 to 12.

X¹preferably-COO-or-SO₂－。

As R²²²Examples of the alkyl group having 1 to 25 carbon atoms include straight-chain or branched-chain alkyl groups having 1 to 25 carbon atoms such as a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a sec-butyl group, a n-pentyl group, a n-hexyl group, a 1-methylbutyl group, a 3-methylbutyl group, a n-octyl group, a n-decyl group, and a 2-hexyloctyl group. R²²²Preferably an alkyl group having 1 to 12 carbon atoms.

As R²²²Examples of the substituent optionally having the alkyl group having 1 to 25 carbon atoms include a halogen atom and a hydroxyl group.

As R²²²Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include aryl groups having 6 to 18 carbon atoms such as phenyl, naphthyl, anthryl and biphenyl groups; aralkyl groups having 7 to 18 carbon atoms such as benzyl, phenylethyl, and naphthylmethyl.

As R²²²Examples of the substituent which the aromatic hydrocarbon group having 6 to 18 carbon atoms may optionally have include a halogen atom and a hydroxyl group.

As R²²³And R²²⁴Examples of the alkyl group having 1 to 6 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, sec-butyl, n-pentyl, n-hexyl, 1-methylbutyl, and 3-methylbutyl.

As R⁴、R¹⁴、R²⁴、R³⁴、R⁴⁴、R⁵⁴、R⁶⁴、R⁷⁴、R⁸⁴、R⁹⁴、R¹⁰⁴、R¹¹⁴、R⁵、R¹⁵、R²⁵、R³⁵、R⁷⁵And R⁸⁵The electron-withdrawing groups are preferably nitro, cyano, halogen atoms, -OCF₃、－SCF₃、－SF₅、－SF₃Fluoroalkyl (preferably having 1 to 25 carbon atoms), fluoroaryl (preferably having 6 to 18 carbon atoms), -CO-O-R²²²、－SO₂－R²²²or-CO-R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms. ),

more preferably nitro, cyano, fluorine atom, chlorine atom, -OCF₃、－SCF₃Fluoroalkyl, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms. ) More preferably, a cyano group.

Preferably R⁴And R⁵At least one of which is cyano, more preferably R⁴Is cyano and R⁵Is cyano, -CO-O-R²²²or-SO₂－R²²²(R²²²Each independently represents a hydrogen atom, an alkyl group having 1 to 25 carbon atoms and optionally having a halogen atom, or an aromatic hydrocarbon group having 6 to 18 carbon atoms and optionally having a halogen atom. ).

R⁴And R⁵Optionally bonded to each other to form a ring. R⁴And R⁵The rings bonded to each other may be monocyclic or condensed, and monocyclic is preferable. In addition, R⁴And R⁵The ring formed by bonding may contain a hetero atom (nitrogen atom, oxygen atom, sulfur atom) or the like as a constituent element of the ring.

R⁴And R⁵The rings formed by bonding to each other are usually three-to ten-membered rings, preferably five-to seven-membered rings, and more preferably five-membered or six-membered rings.

AsR⁴And R⁵The rings formed by bonding to each other include, for example, the following structures.

[ in the formula, a represents a bond to a carbon atom. R^1E～R^16EEach independently represents a hydrogen atom or a substituent.]

R⁴And R⁵The rings formed by bonding may have a substituent (R in the above formula)^1E～R^16E). Examples of the substituent include a group related to the ring W¹And a group having the same substituent as the optional group. R is as defined above^1E～R^16EEach independently is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and further preferably a methyl group.

R¹⁴And R¹⁵Examples of the ring bonded to each other include⁴And R⁵The rings are bonded to each other to form the same ring.

R²⁴And R²⁵Examples of the ring bonded to each other include⁴And R⁵The rings are bonded to each other to form the same ring.

R³⁴And R³⁵Examples of the ring bonded to each other include⁴And R⁵The rings are bonded to each other to form the same ring.

R⁷⁴And R⁷⁵Examples of the ring bonded to each other include⁴And R⁵The rings are bonded to each other to form the same ring.

R⁸⁴And R⁸⁵Examples of the ring bonded to each other include⁴And R⁵The rings are bonded to each other to form the same ring.

As R¹、R⁴¹、R⁵¹、R⁶¹、R⁹¹、R¹⁰¹、R¹¹¹、R²、R¹²、R⁴²、R⁵²、R⁶²、R⁷²、R⁸²、R⁹²、R¹⁰²、R¹¹²、R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³And R¹¹³Examples of the heterocyclic group include the heterocyclic group represented by the formula³The heterocyclic group shown is the same group, and is preferably a pyrrolidinyl group, a piperidinyl group, a tetrahydrofurfuryl group, a tetrahydropyranyl group, a tetrahydrothienyl group (Japanese: テトラヒドロチオフェノ group), a tetrahydrothiopyranyl group or a pyridyl group.

As R¹、R⁴¹、R⁵¹、R⁶¹、R⁹¹、R¹⁰¹、R¹¹¹、R²、R¹²、R⁴²、R⁵²、R⁶²、R⁷²、R⁸²、R⁹²、R¹⁰²、R¹¹²、R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³And R¹¹³Examples of the aliphatic hydrocarbon group having 1 to 25 carbon atoms include³The aliphatic hydrocarbon groups having 1 to 25 carbon atoms are the same.

The aliphatic hydrocarbon group having 1 to 25 carbon atoms is preferably an alkyl group having 1 to 15 carbon atoms, and more preferably an alkyl group having 1 to 12 carbon atoms.

As R¹、R⁴¹、R⁵¹、R⁶¹、R⁹¹、R¹⁰¹、R¹¹¹、R²、R¹²、R⁴²、R⁵²、R⁶²、R⁷²、R⁸²、R⁹²、R¹⁰²、R¹¹²、R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³And R¹¹³Examples of the substituent optionally contained in the aliphatic hydrocarbon group include a halogen atom, a hydroxyl group, a nitro group, a cyano group and-SO₃H, and the like.

In addition, R¹、R⁴¹、R⁵¹、R⁶¹、R⁹¹、R¹⁰¹、R¹¹¹、R²、R¹²、R⁴²、R⁵²、R⁶²、R⁷²、R⁸²、R⁹²、R¹⁰²、R¹¹²-CH contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms₂-or-CH is optionally substituted by-NR^12A-、－SO₂－、－CO－、－O－、－COO－、－OCO－、－CONR^13A－、－NR^14A－CO－、－S－、－SO－、－CF₂-or-CHF-.

R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³And R¹¹³-CH contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－。

-CH contained in the aliphatic hydrocarbon group having 1 to 25 carbon atoms₂when-or-CH-is substituted, it is preferably-O-, -S-, -CO-O-or-SO₂-a permutation.

As R^1A、R^2A、R^3A、R^4A、R^5A、R^6A、R^7A、R^8A、R^9A、R^10A、R^11A、R^12A、R^13AAnd R^14AExamples of the alkyl group having 1 to 6 carbon atoms include the group represented by the formula^1AThe alkyl groups having 1 to 6 carbon atoms are the same.

As R¹、R⁴¹、R⁵¹、R⁶¹、R⁹¹、R¹⁰¹、R¹¹¹、R²、R¹²、R⁴²、R⁵²、R⁶²、R⁷²、R⁸²、R⁹²、R¹⁰²、R¹¹²、R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³And R¹¹³Shown inAromatic hydrocarbon group having 6 to 18 carbon atoms, for example, R³The same aromatic hydrocarbon group having 6 to 18 carbon atoms is preferably an aryl group having 6 to 18 carbon atoms, more preferably a phenyl group or a benzyl group.

Examples of the substituent optionally contained in the aromatic hydrocarbon group having 6 to 18 carbon atoms include a halogen atom; a hydroxyl group; a mercapto group; an amino group; a nitro group; a cyano group; -SO₃H group, etc.

R¹、R⁴¹、R⁵¹、R⁶¹、R⁹¹、R¹⁰¹、R¹¹¹、R²、R¹²、R⁴²、R⁵²、R⁶²、R⁷²、R⁸²、R⁹²、R¹⁰²、R¹¹²-CH contained in an aromatic hydrocarbon group having 6 to 18 carbon atoms₂-or-CH is optionally substituted by-NR^12A－、－SO₂－、－CO－、－O－、－COO－、－OCO－、－CONR^13A－、－NR^14A－CO－、－S－、－SO－、－CF₂-or-CHF-.

R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³And R¹¹³-CH contained in an aromatic hydrocarbon group having 6 to 18 carbon atoms₂-or-CH-optionally substituted by-O-, -S-, -NR ═^1A－、－CO－、－CO－O－、－O－CO－、－O－CO－O－、－CONR^2A－、－O－CO－NR^3A－、－NR^4A－CO－、－NR^5A－CO－O－、－NR^6A－CO－NR^7A－、－CO－S－，－S－CO－S－、－S－CO－NR^8A－、－NR^9A－CO－S－、－CS－、－O－CS－、－CS－O－、－NR^10A－CS－、－NR^11A-CS-S-, -S-CS-, -CS-S-, -S-CS-S-, -SO-or-SO₂－。

-CH contained in the C6-18 aromatic hydrocarbon group₂-or-CH ═ is replacedIn the case of (2), it is preferably substituted by-O-or-SO₂-a permutation.

R²And R³May be connected to each other to form a ring. As R²And R³The component of the connected ring comprises a ring W¹The double bond of (a). Namely, R²And R³The ring formed by connection with the ring W¹Forming a fused ring. As R²And R³The ring formed by connection with the ring W¹Specific examples of the condensed ring to be formed include the ring structures described below.

R¹²And R¹³In rings formed by bonding to each other, as R¹²And R¹³The component of the connected ring comprises a ring W²The double bond of (a). Namely, R¹²And R¹³Ring formed by bonding with ring W²Forming a fused ring. Specifically, the following may be mentionedR²And R³The ring formed by connection with the ring W¹The fused rings formed are identical rings.

R⁴²And R⁴³In rings formed by bonding to each other, as R⁴²And R⁴³The component of the connected ring comprises a ring W⁵The double bond of (a). Namely, R⁴²And R⁴³Ring formed by bonding with ring W⁵Forming a fused ring. Specifically, R may be mentioned²And R³The ring formed by connection with the ring W¹The fused rings formed are identical rings.

R⁵²And R⁵³In rings formed by bonding to each other, as R⁵²And R⁵³The component of the connected ring comprises a ring W⁶The double bond of (a). Namely, R⁵²And R⁵³Ring formed by bonding with ring W⁶Forming a fused ring. Specifically, R may be mentioned²And R³The ring formed by connection with the ring W¹The fused rings formed are identical rings.

R⁶²And R⁶³In rings formed by bonding to each other, as R⁶²And R⁶³The component of the connected ring comprises a ring W⁷The double bond of (a). Namely, R⁶²And R⁶³Ring formed by bonding with ring W⁷Forming a fused ring. Specifically, R may be mentioned²And R³The ring formed by connection with the ring W¹The fused rings formed are identical rings.

R⁷²And R⁷³In rings formed by bonding to each other, as R⁷²And R⁷³The component of the connected ring comprises a ring W⁸The double bond of (a). Namely, R⁷²And R⁷³Ring formed by bonding with ring W⁸Forming a fused ring. Specifically, R may be mentioned²And R³The ring formed by connection with the ring W¹The fused rings formed are identical rings.

R⁸²And R⁸³In rings formed by bonding to each other, as R⁸²And R⁸³The component of the connected ring comprises a ring W⁹The double bond of (a). Namely, R⁸²And R⁸³Ring formed by bonding with ring W⁹Forming a fused ring. Specifically, R may be mentioned²And R³The ring formed by connection with the ring W¹The fused rings formed are identical rings.

R⁹²And R⁹³In rings formed by bonding to each other, as R⁹²And R⁹³The component of the connected ring comprises a ring W¹²The double bond of (a). Namely, R⁹²And R⁹³Ring formed by bonding with ring W¹²Forming a fused ring. Specifically, R may be mentioned²And R³The ring formed by connection with the ring W¹The fused rings formed are identical rings.

R¹⁰²And R¹⁰³In rings formed by bonding to each other, as R¹⁰²And R¹⁰³The component of the connected ring comprises a ring W¹⁰The double bond of (a). Namely, R¹⁰²And R¹⁰³Ring formed by bonding with ring W¹⁰Forming a fused ring. Specifically, R may be mentioned²And R³The ring formed by connection with the ring W¹The fused rings formed are identical rings.

R¹¹²And R¹¹³In rings formed by bonding to each other, as R¹¹²And R¹¹³The component of the connected ring comprises a ring W¹¹The double bond of (a). Namely, R¹¹²And R¹¹³Ring formed by bonding with ring W¹¹Forming a fused ring. Specifically, R may be mentioned²And R³The ring formed by connection with the ring W¹The fused rings formed are identical rings.

R¹And R²May be bonded to each other to form a ring. R¹And R²The rings formed by bonding to each other contain 1 nitrogen atom as a constituent of the ring. R¹And R²The rings bonded to each other may be monocyclic or condensed, and monocyclic is preferable. R¹And R²The ring formed by bonding may further contain a hetero atom (oxygen atom, sulfur atom, nitrogen atom, etc.) as a constituent element of the ring. R¹And R²Each otherThe ring formed by bonding is preferably an alicyclic ring, and more preferably an alicyclic ring having no unsaturated bond.

R¹And R²The rings formed by bonding to each other are usually three-to ten-membered rings, preferably five-to seven-membered rings, and more preferably five-membered or six-membered rings.

R¹And R²The rings formed by bonding to each other may have a substituent, and examples thereof include a ring W²Ring W¹²And a group having the same substituent as the optional group.

As R¹And R²Examples of the rings bonded to each other include the following rings.

R⁴¹And R⁴²Examples of the ring bonded to each other include¹And R²The rings are bonded to each other to form the same ring.

R⁵¹And R⁵²Examples of the ring bonded to each other include¹And R²The rings are bonded to each other to form the same ring.

R⁶¹And R⁶²Examples of the ring bonded to each other include¹And R²The rings are bonded to each other to form the same ring.

R⁹¹And R⁹²Examples of the ring bonded to each other include¹And R²The rings are bonded to each other to form the same ring.

R¹⁰¹And R¹⁰²Examples of the ring bonded to each other include¹And R²The rings are bonded to each other to form the same ring.

R¹¹¹And R¹¹²Examples of the ring bonded to each other include¹And R²The rings are bonded to each other to form the same ring.

As R⁶、R⁷And R⁸The divalent linking group is a C1-18 divalent aliphatic hydrocarbon group optionally having a substituent orOptionally a C6-18 divalent aromatic hydrocarbon group having a substituent. -CH contained in the divalent aliphatic hydrocarbon group and divalent aromatic hydrocarbon group₂Optionally substituted by-O-, -S-, -NR^1B－(R^1BHydrogen atom or C1-6 alkyl group), -CO-, -SO-₂－、－SO－、－PO₃-a permutation.

Examples of the optional substituent of the divalent aliphatic hydrocarbon group and the divalent aromatic hydrocarbon group include a halogen atom, a hydroxyl group, a carboxyl group, an amino group, and the like.

R⁶、R⁷And R⁸The divalent linking groups are each independently preferably a divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms, which may be substituted, and more preferably a divalent aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be substituted.

As R⁶、R⁷And R⁸Specific examples of the divalent linking group include the following linking groups. Wherein denotes a bond.

R⁶And R⁷Independently of each other, the aliphatic hydrocarbon group is preferably a C1-18 divalent aliphatic hydrocarbon group optionally having a substituent or a linking group represented by the following formula, and more preferably a C1-12 divalent aliphatic hydrocarbon group optionally having a substituent or a linking group represented by the following formulaAnd (4) clustering.

R⁸Preferably a C1-18 divalent aliphatic hydrocarbon group optionally having a substituent or a linking group represented by the following formula.

As R⁹And R¹⁰The trivalent linking group may be, independently, a trivalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted or a trivalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted. -CH contained in the trivalent aliphatic hydrocarbon group₂May be substituted by-O-, -S-, -CS-, -CO-, -SO-, -NR-, -C-O-C-C^11B－(R^11BRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms).

Examples of the substituent which the trivalent aliphatic hydrocarbon group and the trivalent aromatic hydrocarbon group may optionally have include a halogen atom, a hydroxyl group, a carboxyl group, an amino group, and the like.

R⁹And R¹⁰The trivalent connecting groups are preferably trivalent aliphatic hydrocarbon groups having 1 to 12 carbon atoms and optionally having a substituent.

As R⁹And R¹⁰Specific examples of the trivalent linking group include the linking groups described below.

As R¹¹Examples of the tetravalent linking group include a tetravalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted, or a tetravalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may be substituted. -CH contained in the tetravalent aliphatic hydrocarbon group₂May be substituted by-O-, -S-, -CS－、－CO－、－SO－、－NR^11C－(R^11CRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms).

Examples of the optional substituent of the tetravalent aliphatic hydrocarbon group and the tetravalent aromatic hydrocarbon group include a halogen atom, a hydroxyl group, a carboxyl group, an amino group and the like.

R¹¹The tetravalent connecting groups are preferably tetravalent aliphatic hydrocarbon groups having 1 to 12 carbon atoms and optionally having substituents.

As R¹¹Specific examples of the tetravalent linker include the following linkers.

R¹Preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms.

R²Preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms.

R¹And R²The compound is preferably linked to each other to form a ring, more preferably an aliphatic ring, even more preferably an aliphatic ring having no unsaturated bond, and particularly preferably a pyrrolidine ring or piperidine ring structure. R³Preferably nitro, cyano, halogen atoms, -OCF₃、－SCF₃、－SF₅、－SF₃Fluoroalkyl (preferably having 1 to 25 carbon atoms), fluoroaryl (preferably having 6 to 18 carbon atoms), -CO-O-R^111Aor-SO₂－R^112A(R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms),

more preferably a cyano group, a fluorine atom, a chlorine atom, -OCF₃、－SCF₃Fluoroalkyl, -CO-O-R^111Aor-SO₂－R^112A(R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom), more preferably a cyano group or a fluorine atom, and particularly preferably a cyano group.

R⁴And R⁵Each independently of the others is preferably nitro, cyano, halogen atom, -OCF₃、－SCF₃、－SF₅、－SF₃Fluoroalkyl, fluoroaryl, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms),

more preferably nitro, cyano, fluorine atom, chlorine atom, -OCF₃、－SCF₃Fluoroalkyl, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms),

further preferred is cyano, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms), and is particularly preferably a cyano group.

Preferably R⁴And R⁵At least one of which is cyano, more preferably R⁴Is cyano and R⁵Is cyano, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents a hydrogen atom, an optionally substituted alkyl group having 1 to 25 carbon atoms, or an optionally substituted aromatic hydrocarbon group having 6 to 18 carbon atoms).

R⁴And R⁵Preferably of the same construction.

R⁴And R⁵Preferably both cyano groups.

R⁴¹、R⁵¹、R⁶¹、R⁹¹、R¹⁰¹And R¹¹¹Each independently preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms.

R¹²、R⁴²、R⁵²、R⁶²、R⁷²、R⁸²、R⁹²、R¹⁰²And R¹¹²Each independently preferablyIs an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms.

R⁴¹And R⁴²The compound is preferably linked to each other to form a ring, more preferably an aliphatic ring, even more preferably an aliphatic ring having no unsaturated bond, and particularly preferably a pyrrolidine ring or piperidine ring structure.

R⁵¹And R⁵²The compound is preferably linked to each other to form a ring, more preferably an aliphatic ring, even more preferably an aliphatic ring having no unsaturated bond, and particularly preferably a pyrrolidine ring or piperidine ring structure.

R⁶¹And R⁶²The compound is preferably linked to each other to form a ring, more preferably an aliphatic ring, even more preferably an aliphatic ring having no unsaturated bond, and particularly preferably a pyrrolidine ring or piperidine ring structure.

R⁹¹And R⁹²The compound is preferably linked to each other to form a ring, more preferably an aliphatic ring, even more preferably an aliphatic ring having no unsaturated bond, and particularly preferably a pyrrolidine ring or piperidine ring structure.

R¹⁰¹And R¹⁰²The compound is preferably linked to each other to form a ring, more preferably an aliphatic ring, even more preferably an aliphatic ring having no unsaturated bond, and particularly preferably a pyrrolidine ring or piperidine ring structure.

R¹¹¹And R¹¹²The compound is preferably linked to each other to form a ring, more preferably an aliphatic ring, even more preferably an aliphatic ring having no unsaturated bond, and particularly preferably a pyrrolidine ring or piperidine ring structure.

R¹³、R²³、R³³、R⁴³、R⁵³、R⁶³、R⁷³、R⁸³、R⁹³、R¹⁰³And R¹¹³Each independently is preferably nitro; a cyano group; a halogen atom; -OCF₃；－SCF₃；－SF₅；－SF₃(ii) a A fluoroalkyl group having 1 to 25 carbon atoms; a fluorinated aryl group having 6 to 18 carbon atoms; -CO-O-R^111Aor-SO₂－R^112A(R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom),

more preferably a cyano group; a fluorine atom; a chlorine atom; -OCF₃；－SCF₃(ii) a A C1-12 fluoroalkyl group; -CO-O-R^111Aor-SO₂－R^112A(R^111AAnd R^112AEach independently represents an alkyl group having 1 to 24 carbon atoms and optionally having a halogen atom),

cyano is particularly preferred.

R¹⁴、R²⁴、R³⁴、R⁴⁴、R⁵⁴、R⁶⁴、R⁷⁴、R⁸⁴、R⁹⁴、R¹⁰⁴、R¹¹⁴、R¹⁵、R²⁵、R³⁵、R⁷⁵And R⁸⁵Each independently of the others is preferably nitro, cyano, halogen atom, -OCF₃、－SCF₃、－SF₅、－SF₃、－CO－O－R²²²、－SO₂－R²²²(R²²²An alkyl group having 1 to 25 carbon atoms optionally having a halogen atom), a fluoroalkyl group having 1 to 25 carbon atoms or a fluoroaryl group having 6 to 18 carbon atoms,

more preferably nitro, cyano, fluorine atom, chlorine atom, -OCF₃、－SCF₃Fluoroalkyl, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents an alkyl group having 1 to 25 carbon atoms and optionally having a halogen atom),

further preferred is cyano, -CO-O-R²²²or-SO₂－R²²²(R²²²Represents an alkyl group having 1 to 25 carbon atoms and optionally having a halogen atom),

cyano is particularly preferred.

R¹⁴And R¹⁵Preferably of the same construction.

R²⁴And R²⁵Preferably of the same construction.

R³⁴And R³⁵Preferably of the same construction.

R⁷⁴And R⁷⁵Preferably of the same construction.

R⁸⁴And R⁸⁵Preferably of the same construction.

The compound represented by the formula (I) is more preferably any of the compound represented by the formula (I-1A), the compound represented by the formula (I-2A) or the compound represented by the formula (I-3A).

[ in the formula, R¹、R²、R³、R⁴And R⁵The same meaning as above is indicated.

Rx₁、Rx₂、Rx₃、Rx₄、Rx₅、Rx₆、Rx₇And Rx₈Each independently represents a hydrogen atom or a substituent.

m1 represents an integer of 0 to 4, and m2 represents an integer of 0 to 5. ]

As Rx₁～Rx₈Examples of the substituent include a group bonded to the ring W¹And a group having the same substituent as the optional group.

m1 and m2 are each independently preferably 0 or 1.

The compound represented by the formula (II) is preferably a compound represented by the formula (II-A).

[ in the formula, R²、R³、R⁴、R⁵、R⁶、R¹²、R¹³、R¹⁴And R¹⁵The same meaning as above is indicated.

R_x9、R_x10、R_x11And R_x12Each independently represents a hydrogen atom or a substituent.]

As R_x9～R_x12Examples of the substituent include a group bonded to the ring W¹Optionally havingThe same substituents.

The compound represented by the formula (III) is preferably a compound represented by the formula (III-A).

[ in the formula, R³、R⁴、R⁵、R²³、R²⁴And R²⁵The same meaning as above is indicated.

R_x13、R_x14、R_x15And R_x16Each independently represents a hydrogen atom or a substituent.]

As R_x13～R_x16Examples of the substituent include a group bonded to the ring W¹And a group having the same substituent as the optional group.

Examples of the compound represented by the formula (I) (hereinafter, may be referred to as compound (I)) include the compounds described below.

The compound (I) is preferably a compound represented by the formula (1-1) to the formula (1-4), the formula (1-7), the formula (1-8), the formula (1-10), the formula (1-12), the formula (1-20) to the formula (1-25), the formula (1-54) to the formula (1-57), the formula (1-59), the formula (1-63) to the formula (1-68), the formula (1-70) to the formula (1-78), the formula (1-80), the formula (1-124) to the formula (1-132), the formula (1-135), the formula (1-137) to the formula (1-142), the formula (1-158) to the formula (1-172), the formula (1-218) to the formula (1-229),

more preferably a compound represented by the formula (1-1), the formula (1-2), the formula (1-4), the formula (1-7), the formula (1-10), the formula (1-12), the formula (1-20), the formula (1-22), the formula (1-54) to the formula (1-56), the formula (1-59), the formula (1-63) to the formula (1-65), the formula (1-66), the formula (1-71), the formula (1-124), the formula (1-125), the formula (1-126), the formula (1-128), the formula (1-131), the formula (1-158), the formula (1-160), the formula (1-164), the formula (1-169), the formula (1-218) to the formula (1-227),

more preferred are compounds represented by the formulae (1-54) to (1-56), the formulae (1-59), the formulae (1-64), the formulae (1-125), the formulae (1-218) to (1-229).

Examples of the compound represented by the formula (II) (hereinafter, sometimes referred to as compound (II)) include the compounds described below.

The compound (II) is preferably a compound represented by the formula (2-1), the formula (2-2), the formula (2-5) to the formula (2-12), the formula (2-24) to the formula (2-28), the formula (2-32), the formula (2-33), the formula (2-38) to the formula (2-44), the formula (2-70), the formula (2-71), the formula (2-103) to the formula (2-106), more preferably a compound represented by the formula (2-1), the formula (2-2), the formula (2-5) to the formula (2-10), the formula (2-103) to the formula (2-106).

Examples of the compound represented by the formula (III) (hereinafter, sometimes referred to as compound (III)) include the compounds described below.

Examples of the compound represented by the formula (IV) (hereinafter, sometimes referred to as compound (IV)) include the compounds described below.

Examples of the compound represented by the formula (V) (hereinafter, sometimes referred to as compound (V)) include the compounds described below.

The compound (V) is preferably a compound represented by any one of the formulae (5-1) to (5-3), the formula (5-6), the formula (5-7), the formula (5-9), the formula (5-15), the formula (5-21), the formula (5-23), the formula (5-25), the formula (5-26), the formula (5-32), the formula (5-36) or the formula (5-38), more preferably a compound represented by any one of the formulae (5-1) to (5-3), the formula (5-21), the formula (5-25) or the formula (5-36).

Examples of the compound represented by the formula (VI) (hereinafter, sometimes referred to as compound (VI)) include the compounds described below.

As the compound (VI), preferred are compounds represented by the formula (6-1), the formula (6-2), the formula (6-4), the formula (6-5), the formula (6-7), the formula (6-8), the formula (6-9), the formula (6-12), the formula (6-15), the formula (6-18), the formula (6-19), the formula (6-22), the formula (6-23), the formula (6-50), the formula (6-57), the formula (6-69), the formula (6-80), the formula (6-85) and the formula (6-94), more preferred are compounds represented by the formula (6-1), the formula (6-2), the formula (6-4), the formula (6-8), the formula (6-15), the formula (6-22) and the formula (6-80).

Examples of the compound represented by the formula (VII) (hereinafter, sometimes referred to as compound (VII)) include the compounds described below.

The compound (VII) is preferably a compound represented by the formula (7-1) to the formula (7-9), the formula (7-12), the formula (7-14), the formula (7-17), the formula (7-42) to the formula (7-44), or the formula (7-57), more preferably a compound represented by the formula (7-1) to the formula (7-8).

Examples of the compound represented by the formula (VIII) (hereinafter, sometimes referred to as compound (VIII)) include the compounds described below.

The compound (VIII) is preferably a compound represented by the formula (8-1), the formula (8-2), the formula (8-4), the formula (8-5), the formula (8-11), the formula (8-13) to the formula (8-17), the formula (8-25), the formula (8-26), the formula (8-47) or the formula (8-48), more preferably a compound represented by the formula (8-1), the formula (8-4), the formula (8-5), the formula (8-15), the formula (8-17) or the formula (8-25).

< method for producing Compound (I) >

The compound (I) can be obtained, for example, by reacting a compound represented by the formula (I-1) (hereinafter, sometimes referred to as compound (I-1)) with a compound represented by the formula (I-2) (hereinafter, sometimes referred to as compound (I-2)).

[ in the formula, a ring W¹、R¹～R⁵The same meaning as above is indicated.]

The reaction of compound (I-1) with compound (I-2) is usually carried out by mixing compound (I-1) with compound (I-2), and preferably adding compound (I-2) to compound (I-1).

Further, the reaction of compound (I-1) with compound (I-2) is preferably carried out by mixing compound (I-1) with compound (I-2) in the presence of a base and a methylating agent,

it is preferable to mix the compound (1-1), the compound (I-2), a base and a methylating agent,

more preferably, compound (I-2) and a base are mixed into a mixture of compound (1-1) and a methylating agent,

it is further preferred to add a mixture of the compound (I-2) and a base to a mixture of the compound (1-1) and a methylating agent.

Examples of the base include metal hydroxides (preferably, alkali metal hydroxides) such as sodium hydroxide, lithium hydroxide, potassium hydroxide, cesium hydroxide, rubidium hydroxide, calcium hydroxide, barium hydroxide, and magnesium hydroxide; metal alkoxides (preferably alkali metal alkoxides) such as sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, sodium isopropoxide, sodium tert-butoxide, and potassium tert-butoxide; metal hydrides such as lithium hydride, sodium hydride, potassium hydride, lithium aluminum hydride, sodium borohydride, aluminum hydride, and sodium aluminum hydride; metal oxides such as calcium oxide and magnesium oxide; metal carbonates (preferably alkaline earth metal carbonates) such as sodium hydrogen carbonate, sodium carbonate, and potassium carbonate; organic alkyl metal compounds such as n-butyllithium, t-butyllithium, methyllithium and grignard reagents; amine compounds (preferably tertiary amines such as triethylamine and diisopropylethylamine) such as ammonia, triethylamine, diisopropylethylamine, ethanolamine, pyrrolidine, piperidine, diazabicycloundecene, diazabicyclononene, guanidine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, pyridine, aniline, dimethoxyaniline, ammonium acetate, and β -alanine; an amino metal compound (preferably an alkali metal amide) such as lithium diisopropylamide, sodium amide, potassium hexamethyldisilazide, or the like; sulfonium compounds such as trimethylsulfonium hydroxide; iodonium compounds such as diphenyliodonium hydroxide; phosphazene bases, and the like.

The amount of the base used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-1).

Examples of the methylating agent include methyl iodide, dimethyl sulfate, methyl methanesulfonate, methyl fluorosulfonate, methyl p-toluenesulfonate, methyl trifluoromethanesulfonate, and trimethyloxonium tetrafluoroborate.

The amount of the methylating agent used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-1).

The reaction of compound (I-1) with compound (I-2) may be carried out in the presence of a solvent. Examples of the solvent include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N-dimethylacetamide, N-dimethylformamide, and water. Acetonitrile, tetrahydrofuran, chloroform, dichloromethane, and diethyl ether are preferable, acetonitrile, tetrahydrofuran, and chloroform are more preferable, and acetonitrile is further preferable.

In addition, the solvent is preferably a dehydration solvent.

The reaction time of the compound (I-1) with the compound (I-2) is usually 0.1 to 10 hours, preferably 0.2 to 3 hours.

The reaction temperature of the compound (I-1) and the compound (I-2) is usually-50 to 150 ℃ and preferably-20 to 100 ℃.

The amount of the compound (I-2) to be used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, based on 1 mol of the compound (I-1).

Examples of the compound (I-1) include the following compounds.

As the compound (I-2), commercially available products can be used, and examples thereof include the compounds described below.

The compound (I-1) can be obtained, for example, by reacting a compound represented by the formula (I-3) (hereinafter sometimes referred to as the compound (I-3)) with a compound represented by the formula (I-4) (hereinafter sometimes referred to as the compound (I-4)).

[ in the formula (I-3), the ring W¹、R¹、R²And R³The same meaning as above is indicated. E₁Represents a leaving group.]

As E₁Examples of the leaving group include a halogen atom, a p-toluenesulfonyl group, a trifluoromethanesulfonyl group and the like.

The reaction of compound (I-3) with compound (I-4) is carried out by mixing compound (I-3) with compound (I-4).

The amount of the compound (I-4) to be used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-3).

The reaction of compound (I-3) with compound (I-4) may be carried out in the presence of a solvent. Examples of the solvent include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N-dimethylacetamide, N-dimethylformamide, and water. Acetonitrile, tetrahydrofuran, chloroform, dichloromethane, and diethyl ether are preferable, acetonitrile, tetrahydrofuran, and chloroform are more preferable, and methanol, ethanol, isopropanol, and acetonitrile are even more preferable.

The reaction time of the compound (I-3) with the compound (I-4) is usually 0.1 to 10 hours.

The reaction temperature of the compound (I-3) and the compound (I-4) is usually-50 to 150 ℃.

Examples of the compound (I-3) include the following compounds.

The compound (I-4) may be a commercially available compound. Examples thereof include: cyanogen chloride, cyanogen bromide, p-toluenesulfonyl cyanide, trifluoromethanesulfonyl cyanide, 1-chloromethyl-4-fluoro-1, 4-diazabicylbicyclo [2.2.2] octanebis (tetrafluoroborate) (also known as Selectfluor (a registered trademark of Air Products and Chemicals)), benzoyl (phenyliodo) (trifluoromethanesulfonyl) methanide, 2, 8-difluoro-5- (trifluoromethyl) -5H-dibenzo [ b, d ] thiophen-5-ium trifluoromethanesulfonate, N-bromosuccinimide, N-chlorosuccinimide, N-iodosuccinimide, and the like.

The compound (I-3) can be obtained by reacting a compound represented by the formula (I-5) (hereinafter, sometimes referred to as the compound (I-5)) with a compound represented by the formula (I-6) (hereinafter, sometimes referred to as the compound (I-6)).

[ in the formula, a ring W¹、R¹And R²The same meaning as above is indicated.]

The reaction of compound (I-5) with compound (I-6) is carried out by mixing compound (I-5) with compound (I-6).

The amount of the compound (I-6) to be used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-5).

The reaction of compound (I-5) with compound (I-6) may be carried out in the presence of a solvent. Examples thereof include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N-dimethylacetamide, N-dimethylformamide, and water. Preferably benzene, toluene, ethanol, acetonitrile.

The reaction time of the compound (I-5) with the compound (I-6) is usually 0.1 to 10 hours.

The reaction temperature of the compound (I-5) and the compound (I-6) is usually-50 to 150 ℃.

Examples of the compound (I-5) include the compounds described below.

As the compound (I-6), ammonia; primary amines such as methylamine, ethylamine, ethanolamine, 4-hydroxybutylamine and the like; secondary amines such as dimethylamine, diethylamine, dibutylamine, pyrrolidine, piperidine, 3-hydroxypyrrolidine, 4-hydroxypiperidine and azetidine.

Further, the compound (I-1) can also be obtained by reacting a compound represented by the formula (I-5-1) (hereinafter, sometimes referred to as the compound (I-5-1)) with the compound (I-6).

[ in the formula (I-5-1), the ring W¹And R³The same meaning as above is indicated.]

The reaction of compound (I-5-1) with compound (I-6) is carried out by mixing compound (I-5-1) with compound (I-6).

The amount of the compound (I-6) to be used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-5-1).

The reaction of compound (I-5-1) with compound (I-6) may be carried out in the presence of a solvent. Examples thereof include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N-dimethylacetamide, N-dimethylformamide, and water. Preferably benzene, toluene, ethanol, acetonitrile.

The reaction time of the compound (I-5-1) with the compound (I-6) is usually 0.1 to 10 hours.

The reaction temperature of the compound (I-5-1) and the compound (I-6) is usually-50 to 150 ℃.

Examples of the compound represented by the formula (I-5-1) include the compounds described below.

Compound (I) can also be obtained by reacting a compound represented by formula (I-7) (hereinafter sometimes referred to as compound (I-7)) with compound (I-6).

[ in the formula (I-7), the ring W¹、R³、R⁴And R⁵The same meaning as above is indicated.]

The reaction of compound (I-7) with compound (I-6) is usually carried out by mixing compound (I-7) with compound (I-6), and preferably adding compound (I-6) to compound (I-7).

Further, the reaction of compound (I-7) with compound (I-6) is preferably carried out by mixing compound (I-7) with compound (I-6) in the presence of a base and a methylating agent,

more preferably, compound (I-7), compound (I-6), a base and a methylating agent are mixed,

it is further preferable to mix compound (I-6) in a mixture of compound (I-7), a methylating agent and a base.

Examples of the base include the same bases as those used in the reaction of the compound (I-1) and the compound (I-2).

The amount of the base used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-7).

Examples of the methylating agent include the same methylating agents as used for the reaction of the compound (I-1) and the compound (I-2).

The amount of the methylating agent used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-7).

The amount of the compound (I-6) to be used is usually 0.1 to 10 mol, preferably 0.5 to 5 mol, based on 1 mol of the compound (I-7).

The reaction of compound (I-7) with compound (I-6) may be carried out in the presence of a solvent. Examples of the solvent include the same solvents as those used for the reaction of the compound (I-1) and the compound (I-2). Methanol, ethanol, isopropanol, toluene, acetonitrile are preferred.

The reaction time of the compound (I-7) with the compound (I-6) is usually 0.1 to 10 hours.

The reaction temperature of the compound (I-7) and the compound (I-6) is usually-50 to 150 ℃.

Examples of the compound (I-7) include the compounds described below.

Compound (I-7) can also be obtained by reacting a compound represented by formula (I-8) with compound (I-4).

[ in the formula (I-8), the ring W¹、R⁴And R⁵Is shown and described aboveThe same meaning is used.]

The reaction of compound (I-8) with compound (I-4) can be carried out by mixing compound (I-8) with compound (I-4).

The reaction of compound (I-8) with compound (I-4) is preferably carried out in the presence of a base. Examples of the base include the same bases as those used in the reaction of the compound (I-1) and the compound (I-2). Preferably, the metal hydroxide (more preferably, an alkali metal hydroxide), the metal alkoxide (more preferably, an alkali metal alkoxide), the amine compound, and the amino metal compound (more preferably, an alkali metal amide) are used.

The amount of the base to be used is usually 0.1 to 10 moles, preferably 0.5 to 2 moles, based on 1 mole of the compound (I-8).

The reaction of compound (I-8) with compound (I-4) may be carried out in the presence of a solvent. Examples of the solvent include the same solvents as those used in the reaction of the compound (I-1) and the compound (I-2). Toluene, acetonitrile, methanol, ethanol, isopropanol are preferred.

The reaction time of the compound (I-8) with the compound (I-4) is usually 0.1 to 10 hours.

The reaction temperature of the compound (I-8) and the compound (I-4) is usually-50 to 150 ℃.

Examples of the compound (I-8) include the compounds described below.

Compound (I-8) can also be obtained by reacting compound (I-5) with compound (I-2). The reaction of compound (I-5) with compound (I-2) can be carried out by mixing compound (I-5) with compound (I-2).

The reaction of compound (I-5) with compound (I-2) is preferably carried out in the presence of a base. Examples of the base include the same bases as those used in the reaction of the compound (I-1) and the compound (I-2). The amount of the base to be used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-5).

The reaction of compound (I-5) with compound (I-2) may be carried out in the presence of a solvent. Examples of the solvent include the same solvents as those used in the reaction of the compound (I-1) and the compound (I-2). Methanol, ethanol, isopropanol, toluene, acetonitrile are preferred.

The reaction time of the compound (I-5) with the compound (I-2) is usually 0.1 to 10 hours.

The reaction temperature of the compound (I-5) and the compound (I-2) is usually-50 to 150 ℃.

The amount of the compound (I-2) to be used is usually 0.1 to 10 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-5).

Further, the compound (I-7) can also be obtained by reacting the compound (I-5-1) with the compound (I-2).

The reaction of compound (I-5-1) with compound (I-2) is carried out by mixing compound (I-5-1) with compound (I-2).

The amount of the compound (I-2) to be used is usually 0.1 to 5 mol, preferably 0.5 to 2 mol, based on 1 mol of the compound (I-5-1).

The reaction of compound (I-5-1) with compound (I-2) may be carried out in the presence of a solvent. Examples thereof include acetonitrile, benzene, toluene, acetone, ethyl acetate, chloroform, dichloroethane, monochlorobenzene, methanol, ethanol, isopropanol, tert-butanol, 2-butanone, tetrahydrofuran, diethyl ether, dimethyl sulfoxide, N-dimethylacetamide, N-dimethylformamide, and water. Preferably benzene, toluene, ethanol, acetonitrile.

The reaction time of the compound (I-5-1) with the compound (I-2) is usually 0.1 to 10 hours.

The reaction temperature of the compound (I-5-1) and the compound (I-2) is usually-50 to 150 ℃.

< production method of Compound (II) to Compound (VIII) >)

Compound (II) can be obtained, for example, by reacting 2 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (II-1).

[ in the formula, R²、R¹²And R⁶The same meaning as above is indicated.]

Examples of the compound represented by the formula (II-1) include the compounds described below.

Compound (III) can be obtained, for example, by reacting 2 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (III-1).

[ in the formula, a ring W¹¹¹The same meaning as above is indicated.]

Examples of the compound represented by the formula (III-1) include the compounds described below.

Compound (IV) can be obtained, for example, by reacting 2 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (IV-1).

[ in the formula, a ring W¹¹²Ring W¹¹³、R⁷The same meaning as above is indicated.]

Examples of the compound represented by the formula (IV-1) include the compounds described below.

Compound (V) can be obtained, for example, by reacting 2 molar equivalents of compound (I-1) with 1 molar equivalent of the compound represented by formula (V-1).

[ in the formula, R⁴、R⁸And R⁴⁴The same meaning as above is indicated.]

Examples of the compound represented by the formula (V-1) include the compounds described below.

Compound (VI) can be obtained, for example, by reacting 3 molar equivalents of compound (I-1) with 1 molar equivalent of the compound represented by formula (VI-1).

[ in the formula, R⁴、R⁸、R⁵⁴And R⁶⁴The same meaning as above is indicated.]

Examples of the compound represented by the formula (VI-1) include the compounds described below.

Compound (VII) can be obtained, for example, by reacting 3 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (VII-1).

[ in the formula, R²、R¹⁰、R⁷²And R⁸²The same meaning as above is indicated.]

Examples of the compound represented by the formula (VII-1) include the compounds described below.

Compound (VIII) can be obtained, for example, by reacting 4 molar equivalents of compound (I-7) with 1 molar equivalent of the compound represented by formula (VIII-1).

[ in the formula, R⁴、R¹¹、R⁹⁴、R¹⁰⁴And R¹¹⁴The same meaning as above is indicated.]

Examples of the compound represented by the formula (VIII-1) include the compounds described below.

< composition comprising Compound (X) >

The present invention also includes a composition containing the compound (X) (preferably any one of the compounds (I) to (VIII)).

The composition containing the compound (X) (preferably any one of the compounds (I) to (VIII)) of the present invention is preferably a resin composition containing the compound (X) (preferably any one of the compounds (I) to (VIII)) and a resin.

The above composition can be used for all purposes, and among them, can be particularly suitably used for purposes where exposure to light including sunlight or ultraviolet rays is possible. Specific examples thereof include glass substitutes and surface coating materials thereof; coating materials for window glass, lighting glass and light source protective glass for houses, facilities, transportation equipment and the like; window films for houses, facilities, transportation equipment, and the like; interior and exterior materials for houses, facilities, transportation facilities, and the like, interior and exterior coatings, and coating films formed using the coatings; alkyd resin paint and coating film formed by the paint; an acrylic paint coating and a coating film formed by using the same; a light source member emitting ultraviolet rays, such as a fluorescent lamp and a mercury lamp; shielding materials for electromagnetic waves and the like generated from precision machinery, electronic and electrical equipment members, and various displays; containers or packaging materials for foods, chemicals, medicines, and the like; bottles, boxes, blisters, cups, special packaging, optical disc coatings, industrial and agricultural sheets or films; fading inhibitors for printed matter, dyed matter, dyes/pigments, and the like; protective films for polymer supports (e.g., for plastic parts such as machine and automotive parts); coating the printed matter; coating an ink jet medium; sanding the interlayer; an optical light film; a safety glass/front windshield interlayer; electrochromic/photochromic applications; coating a protective film outside; a solar thermal control film; cosmetics such as sunscreen cream, shampoo, hair conditioner, and styling agent; fiber products and fibers for clothing such as sportswear, stockings, hats, and the like; household internal articles such as curtains, flannelette blankets, wallpaper, etc.; medical instruments such as plastic lenses, contact lenses, and artificial eyes; optical articles such as filters, backlight display films, prisms, mirrors, and photographic materials; stationery such as a mold film, a transfer printing type label, an anti-doodling film, an adhesive tape, ink and the like; a signboard, a marker, etc., and a surface coating material thereof.

The polymer molded article formed from the resin composition may have any shape such as a flat film, a powder, a spherical pellet, a crushed pellet, a continuous block, a fiber, a tube, a hollow fiber, a pellet, a plate, or a porous shape.

Examples of the resin used in the resin composition include known thermoplastic resins and thermosetting resins that have been conventionally used for the production of various molded articles, sheets, films, and the like.

Examples of the thermoplastic resin include olefin resins such as polyethylene resin, polypropylene resin, and polycycloolefin resin, poly (meth) acrylate resins, polystyrene resins, styrene-acrylonitrile resins, acrylonitrile-butadiene-styrene resins, polyvinyl chloride resins, polyvinylidene chloride resins, polyvinyl acetate resins, polyvinyl butyral resins, polyester resins such as ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol resins, polyethylene terephthalate resins, polybutylene terephthalate resins, and liquid crystal polyester resins, polyacetal resins, polyamide resins, polycarbonate resins, polyurethane resins, and polyphenylene sulfide resins. These resins may be used in the form of one or two or more polymer blends or polymer alloys.

Examples of the thermosetting resin include epoxy resins, melamine resins, unsaturated polyester resins, phenol resins, urea resins, alkyd resins, thermosetting polyimide resins, and the like.

When the resin composition is used as an ultraviolet absorption filter or an ultraviolet absorption film, the resin is preferably a transparent resin.

The resin composition can be obtained by mixing the compound (X) with a resin. The compound (X) may be contained in an amount necessary for imparting desired properties, and for example, may be contained in an amount of 0.01 to 20 parts by mass per 100 parts by mass of the resin.

The composition of the present invention may contain other additives such as a solvent, a crosslinking catalyst, a tackifier, a plasticizer, a softener, a dye, a pigment, an inorganic filler, and the like, as required.

The composition and the resin composition may be a composition for spectacle lenses. The spectacle lens can be formed by molding or the like using the composition for spectacle lenses. The molding method of the composition for spectacle lenses may be injection molding or injection polymerization molding. The injection polymerization molding is a method in which: a composition for an eyeglass lens mainly composed of a monomer or oligomer resin is injected into a lens mold, and the composition for an eyeglass lens is cured by heat or light to be molded into a lens.

The composition for spectacle lenses may be appropriately set according to the molding method. For example, when the spectacle lens is formed by injection molding, the resin composition for a spectacle lens may contain a resin and the compound (X). In addition, when the spectacle lens is formed by injection polymerization molding, a composition for a spectacle lens comprising a curable monomer curable by heat or light and the compound (X) may be used.

The resin contained in the composition for spectacle lenses includes the resins described above, and is preferably a transparent resin. The resin contained in the composition for spectacle lenses is preferably used in the form of one or a polymer blend or a polymer alloy of two or more of a poly (meth) acrylate resin, a polycarbonate resin, a polyamide resin, a polyurethane resin, and a polythiourethane resin. In addition, not only the polymer but also a monomer component may be contained.

The lens composition for spectacles may be a composition comprising a curable monomer and the compound (X). More than 2 curable monomers may be included. Specifically, a mixture of a polyol compound and an isocyanate compound, a mixture of a thiol compound and an isocyanate compound, preferably a mixture of a thiol compound and an isocyanate, and more preferably a mixture of a polyfunctional thiol compound and a polyfunctional isocyanate compound may be mentioned.

The thiol compound is not particularly limited as long as it is a compound having at least 1 mercapto group in the molecule. The shape may be a chain or a ring. Further, the polymer may have a thioether bond, a polysulfide bond, and other functional groups in the molecule. Specific examples of the thiol compound include a thiol-group-containing organic compound having 1 or more thiol groups in 1 molecule, such as an aliphatic polythiol compound, an aromatic polythiol compound, a thiol-group-containing cyclic compound, and a thiol-group-containing thioether compound, which are described in Japanese patent laid-open publication No. 2004-315556. Among these, in view of improving the refractive index and glass transition temperature of the optical material, a polyfunctional thiol compound having 2 or more mercapto groups is preferable, an aliphatic polythiol compound having 2 or more mercapto groups is more preferable, a thioether compound having 2 or more mercapto groups is further preferable, and bis (mercaptomethyl) sulfide, 1, 2-bis [ (2-mercaptoethyl) thio ] -3-mercaptopropane, pentaerythritol tetrathiopropionate, and 4, 8-dimercaptomethyl-1, 11-mercapto-3, 6, 9-trithiaundecane are further preferable. The thiol compounds may be used alone or in combination of 2 or more.

The isocyanate compound is preferably a polyfunctional isocyanate compound having at least 2 isocyanate groups (-NCO) in the molecule, and examples thereof include: aliphatic isocyanate-based compounds (e.g., hexamethylene diisocyanate), alicyclic isocyanate-based compounds (e.g., isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate), aromatic isocyanate-based compounds (e.g., toluene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, naphthalene diisocyanate, triphenylmethane triisocyanate, etc.), and the like. Further, the isocyanate compound may be a polyol compound adduct (adduct) [ for example, an adduct obtained by using glycerin, trimethylolpropane or the like ], an isocyanurate compound, a biuret type compound, a urethane prepolymer type isocyanate compound obtained by addition reaction with a polyether polyol, a polyester polyol, an acrylic polyol, a polybutadiene polyol, a polyisoprene polyol or the like, or the like.

When the lens composition for spectacles contains a curable monomer, a curing catalyst may be contained to improve the curability. Examples of the curing catalyst include tin compounds such as dibutyltin chloride, amines, phosphines, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, inorganic acids, lewis acids, organic acids, silicic acids, tetrafluoroboric acids, peroxides, azo compounds, condensates of aldehydes and ammonia compounds, guanidines, thioureas, thiazoles, sulfenamides, thiurams, dithiocarbamates, xanthates, and acid phosphates described in jp 2004-315556 a. These curing catalysts may be used alone or in combination of 2 or more.

The content of the compound (X) in the composition for spectacle lenses may be, for example, 0.01 to 20 parts by mass per 100 parts by mass of the resin when the composition for spectacle lenses is a resin composition. When the spectacle lens composition is a curable composition, the content of the compound (X) may be 0.00001 to 20 parts by mass per 100 parts by mass of the curable component, for example. The content of the compound (X) is preferably 0.0001 to 15 parts by mass, more preferably 0.001 to 10 parts by mass, still more preferably 0.01 to 5 parts by mass, and particularly preferably 0.1 to 3 parts by mass, per 100 parts by mass of the resin or the curable component.

The amount of the curing catalyst added is preferably 0.0001 to 10.0% by mass, more preferably 0.001 to 5.0% by mass, based on 100% by mass of the spectacle lens composition.

The additive described above may be contained in the composition for spectacle lenses.

Examples

The present invention will be further specifically described below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the examples,% and parts indicating the content or amount used are based on mass unless otherwise specified.

Example 1 Synthesis of Compound represented by formula (UVA-1)

A300 mL four-necked flask equipped with a Dimroth (Dimroth) condenser and a thermometer was placed in a nitrogen atmosphere, and 5 parts of 2-methyl-1, 3-cyclohexanedione, 3.7 parts of piperidine and 50 parts of toluene were charged and stirred under reflux for 5 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 6.8 parts of a compound represented by the formula (M-1).

The obtained compound represented by the formula (M-1), 1.3 parts of dimethyl sulfate and 4 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture, 0.75 part of malononitrile, 1.2 parts of triethylamine and 4 parts of isopropyl alcohol were added, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and the mixture was purified to obtain 0.3 part of a compound represented by the formula (UVA-1).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-1) was produced.

¹H-NMR (deuterated dimethyl sulfoxide (hereinafter sometimes referred to as deuterated DMSO). delta.1.68-1.75 (m, 8H), 2.16(s, 3H), 2.50-2.62 (dt, 4H), 3.40-3.43 (t, 4H)

LC－MS；[M+H]⁺＝242.5

< determination of maximum absorption wavelength and molar absorptivity >

The obtained 2-butanone solution (0.006g/L) of the compound represented by the formula (UVA-1) was added to a 1cm quartz cuvette, which was set in a spectrophotometer UV-2450 (manufactured by Shimadzu corporation), and the absorbance in the wavelength range of 300 to 800nm was measured in units of 1nm step by the two-beam method. The molar absorption coefficient for each wavelength was calculated from the obtained absorbance value, the concentration of the compound represented by the formula (UVA-1) in the solution, and the optical path length of the quartz cuvette.

ε(λ)＝A(λ)/CL

[ in the formula,. epsilon. (. lamda.). lamda. ] represents the molar absorption coefficient (L/(g. cm)) of the compound represented by the formula (UVA-1) at a wavelength of. lamda.,. lamda. -. represents the absorbance at a wavelength of. lamda.,. C represents the concentration (g/L), and L represents the optical path length (cm) of the quartz cuvette. ]

The maximum absorption wavelength of the obtained compound represented by the formula (UVA-1) was 412.9 nm. The compound represented by the formula (UVA-1) obtained had an ε (λ max) of 1.946L/(g · cm), an ε (λ max +30nm) of 0.138L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 14.1.

Example 2 Synthesis of Compound represented by formula (UVA-2)

A300 mL four-necked flask equipped with a Dimerosal condenser and a thermometer was placed in a nitrogen atmosphere, and 5 parts of 2-methyl-1, 3-cyclopentadione, 4.2 parts of piperidine and 50 parts of toluene were charged and stirred under reflux for 5 hours. The solvent was distilled off from the obtained mixture and purified to obtain 4 parts of a compound represented by the formula (M-2).

The obtained compound represented by the formula (M-2), 1.7 parts of dimethyl sulfate and 4.5 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture were added 2.4 parts of cyanoacetic acid (2-ethylbutyl) ester, 1.4 parts of triethylamine and 4.5 parts of isopropyl alcohol, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.5 parts of a compound represented by the formula (UVA-2).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-2) was produced.

¹H-NMR (deuterated DMSO) delta: 0.89-0.93 (t, 6H), 1.36-1.48 (m, 4H), 1.52-1.62(m, 2H), 1.69-1.71 (m, 6H), 2.22(s, 3H), 2.57-2.60 (t, 2H), 3.15-3.18 (t, 2H), 3.53-3.55 (t, 4H), 4.05-4.06 (d, 2H)

LC－MS；[M+H]⁺＝331.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-2) was 382.6 nm. The compound represented by the formula (UVA-2) obtained had an ε (λ max) of 1.9L/(g · cm), an ε (λ max +30nm) of 0.057L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 33.3.

Example 3 Synthesis of Compound represented by formula (UVA-3)

2 parts of a compound represented by the formula (M-2), 1.5 parts of dimethyl sulfate and 4 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. Further, 0.8 part of malononitrile, 1.2 parts of triethylamine and 4 parts of isopropyl alcohol were added to the obtained mixture, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.7 parts of a compound represented by the formula (UVA-3).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-3) was produced.

¹H-NMR (deuterated DMSO) delta: 1.69-1.74 (m, 6H), 2.19(s, 3H), 2.65-2.81 (dt, 4H), 3.57-3.59 (t, 4H)

LC－MS；[M+H]⁺＝228.5(+H)

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-3) was 376.8 nm. The compound represented by the formula (UVA-3) obtained had an ε (λ max) of 2.81L/(g · cm), an ε (λ max +30nm) of 0.058L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 48.4.

Example 4 Synthesis of Compound represented by formula (UVA-4)

Under a nitrogen atmosphere, 1.5 parts of 1, 7-dimethyl-1-2, 3, 4, 6, 7, 8-hexahydroquinolin-5 (1H) -one, 1.1 parts of dimethyl sulfate and 9 parts of acetonitrile were charged and stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture, 0.6 part of malononitrile, 0.9 part of triethylamine and 9 parts of isopropyl alcohol were added, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.2 parts of a compound represented by the formula (UVA-4).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-4) was produced.

¹H-NMR (deuterated DMSO) delta: 1.08-1.09 (d, 3H), 1.76-2.13 (m, 5H), 2.55-2.59 (dd, 1H), 2.66-2.74(m, 1H), 2.81-2.93 (m, 2H), 3.12(s, 3H), 3.28-3.37 (m, 2H)

LC-MS；[M+H]⁺＝228.2

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-4) was 401.8 nm. The compound represented by the formula (UVA-4) obtained had an ε (λ max) of 2.76L/(g · cm), an ε (λ max +30nm) of 0.055L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 50.1.

Example 5 Synthesis of Compound represented by formula (UVA-5)

1.5 parts of 1, 7-dimethyl-1-2, 3, 4, 6, 7, 8-hexahydroquinolin-5 (1H) -one, 1.1 parts of dimethyl sulfate and 9 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture were added 1.6 parts of cyanoacetic acid (2-ethylbutyl) ester, 0.9 parts of triethylamine and 9 parts of isopropyl alcohol, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture and the mixture was purified to obtain 1 part of a compound represented by the formula (UVA-5).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-5) was produced.

¹H-NMR (deuterated DMSO) delta: 0.89-0.93 (t, 6H), 1.07-1.08 (d, 3H), 1.36-1.48 (m, 4H), 1.57-1.62 (m, 3H), 1.82-2.04(m, 4H), 2.04-2.21 (dd, 1H), 2.52-2.57(dd, 1H), 2.73(m, 1H), 3.09(s, 3H), 3.30-3.33 (t, 2H), 4.04-4.06 (dd, 2H)

LC－MS；[M+H]⁺＝：331.2

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-5) was 412.7 nm. The compound represented by the formula (UVA-5) obtained had an ε (λ max) of 1.36L/(g · cm), an ε (λ max +30nm) of 0.202L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 6.74.

Example 6 Synthesis of Compound represented by formula (UVA-6)

A500 mL four-necked flask equipped with a Dimerone condenser and a thermometer was placed in a nitrogen atmosphere, and 20 parts of damascenone (Dimedone), 11.2 parts of pyrrolidine and 200 parts of toluene were charged and stirred under reflux for 5 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 27.4 parts of a compound represented by the formula (M-3).

1.0 part of the obtained compound represented by the formula (M-3), 2.8 parts of p-toluenesulfonylcyanide and 10 parts of acetonitrile were mixed under a nitrogen atmosphere. The resulting mixture was stirred at 0-5 ℃ for 5 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 0.6 part of a compound represented by the formula (M-4).

4.8 parts of a compound represented by the formula (M-4), 4.6 parts of methyl trifluoromethanesulfonate and 24 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture, 1.9 parts of malononitrile, 3 parts of triethylamine and 24 parts of acetonitrile were added, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 2.9 parts of a compound represented by the formula (UVA-6).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-6) was produced.

¹H-NMR(CDCl₃)δ：0.99(s、6H)、1.90-1.96(m、4H)、2.48－2.51(m、4H)、3.70-3.88(dt、4H)

LC－MS；[M+H]⁺＝284.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-6) was 380 nm. The compound represented by the formula (UVA-6) obtained had an ε (λ max) of 1.75L/(g · cm), an ε (λ max +30nm) of 0.032L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 54.53.

Example 7 Synthesis of Compound represented by formula (UVA-7)

1 part of a compound represented by the formula (M-4), 0.6 part of methyl trifluoromethanesulfonate and 10 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture were added 5.2 parts of ethyl cyanoacetate, 4.6 parts of triethylamine and 10 parts of acetonitrile, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 0.5 part of a compound represented by the formula (UVA-7).

LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-7) was produced.

¹H-NMR (deuterated DMSO) delta: 0.960-0.994 (d, 6H), 1.20-1.26 (m, 3H), 1.93(m, 4H), 2.53-2.91 (m, 4H), 3.77-3.81 (m, 4H), 4.10-4.19 (m, 2H)

LC－MS；[M+H]⁺＝314.5(+H)

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-7) was 382.7 nm. The compound represented by the formula (UVA-7) obtained had an ε (λ max) of 1.08L/(g · cm), an ε (λ max +30nm) of 0.153L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 7.04.

Example 8 Synthesis of Compound represented by formula (UVA-8)

0.5 part of a compound represented by the formula (M-4), 0.5 part of dimethyl sulfate and 5 parts of acetonitrile are mixed under a nitrogen atmosphere, and the mixture is stirred at 20 to 30 ℃ for 3 hours to carry out a reaction. Further, 0.4 part of pivaloyl acetonitrile, 0.5 part of triethylamine and 5.0 parts of acetonitrile were added thereto, and the mixture was stirred at 20 to 30 ℃ for 3 hours to effect a reaction. After completion of the reaction, the solvent was distilled off and purified to obtain 0.07 part of a compound represented by the formula (UVA-8).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-8) was produced.

¹H-NMR (deuterated DMSO) delta: 0.92(s, 6H), 1.26(s, 9H), 1.90(s, 4H), 2.55(m, 4H), 3.64-3.71 (m, 4H)

LC－MS；[M+H]⁺＝326.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-8) was 377.4 nm. The compound represented by the formula (UVA-8) obtained had an ε (λ max) of 0.66L/(g · cm), an ε (λ max +30nm) of 0.395L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 1.68.

Example 9 Synthesis of Compound represented by formula (UVA-9)

A300 mL four-necked flask equipped with a Dimerosal condenser and a thermometer was placed under a nitrogen atmosphere, and 70.0 parts of damimetone, 10.4 parts of malononitrile, 40.6 parts of diisopropylethylamine and 100.0 parts of ethanol were added thereto, followed by heating, refluxing and stirring for 3 hours. After completion of the reaction, the solvent was distilled off and purified to obtain 15.1 parts of a compound represented by the formula (M-5).

5 parts of a compound represented by the formula (M-5), 5.8 parts of p-toluenesulfonyl cyanide, 3 parts of potassium tert-butoxide and 50 parts of ethanol were mixed under a nitrogen atmosphere. The resulting mixture was stirred at 0-5 ℃ for 3 hours.

The solvent was distilled off from the obtained mixture, and purification was performed to obtain 3.3 parts of a compound represented by the formula (M-6).

1 part of a compound represented by the formula (M-6), 1 part of methyl trifluoromethanesulfonate, 0.8 part of diisopropylethylamine and 20 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture, 1.4 parts of piperidine and 20 parts of acetonitrile were added, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 0.5 part of a compound represented by the formula (UVA-9).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-9) was produced.

¹H-NMR (deuterated DMSO) delta: 0.99(s, 6H), 1.60(m, 6H), 2.71(s, 2H), 3.80(m, 4H)

LC－MS；[M+H]⁺＝281.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-9) was 385.6 nm. The compound represented by the formula (UVA-9) obtained had an ε (λ max) of 1.65L/(g · cm), an ε (λ max +30nm) of 0.088L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 18.8.

Synthesis example 1 Synthesis of Compound represented by formula (UVA-A1)

A200 mL four-necked flask equipped with a Dimerosal condenser and a thermometer was placed in a nitrogen atmosphere, 10 parts of the compound represented by the formula (M-7) synthesized in Japanese patent laid-open publication No. 2014-194508, 3.6 parts of acetic anhydride, 6.9 parts of cyanoacetic acid (2-butyloctyl) ester and 60 parts of acetonitrile were charged, and the mixture was stirred at 20 to 30 ℃. To the resulting mixture, 4.5 parts of diisopropylethylamine was added dropwise over 1 hour, and the mixture was stirred for 2 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 4.6 parts of a compound represented by the formula (UVA-A1).

Synthesis example 2 Synthesis of Compound represented by formula (UVA-A2)

A100 mL four-necked flask equipped with a Dimerosal condenser and a thermometer was placed in a nitrogen atmosphere, and 6 parts of the compound represented by the formula (M-8), 14.2 parts of dibutylamine and 31.3 parts of isopropanol were mixed, heated under reflux, and then stirred for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 4.6 parts of a compound represented by the formula (UVA-A2).

Synthesis example 3 Synthesis of Compound represented by formula (UVA-A3)

A300 mL four-necked flask equipped with a Dimrot condenser and a thermometer was placed in a nitrogen atmosphere, 30 parts of malondialdehyde diphenylamine hydrochloride, 18.4 parts of Meldrum's acid, 12.9 parts of triethylamine and 90 parts of methanol were added, and the mixture was stirred at 20 to 30 ℃ for 3 hours to effect a reaction. After the completion of the reaction, the solvent was distilled off and the reaction mixture was purified to obtain 24.4 parts of a compound represented by the formula (M-8).

6 parts of the compound represented by the formula (M-8), 21.7 parts of dibenzylamine and 31.3 parts of isopropyl alcohol were mixed, and the mixture was refluxed and then stirred for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 3.5 parts of a compound represented by the formula (UVA-A3).

Synthesis example 4 Synthesis of Compound represented by formula (UVA-A4)

A100 mL four-necked flask equipped with a Dimerosal condenser and a thermometer was placed under a nitrogen atmosphere, and 5 parts of 2-phenyl-1-methylindole-3-carbaldehyde, 1.8 parts of piperidine, 1.5 parts of malononitrile and 20 parts of ethanol were mixed, heated under reflux, and then stirred for 18 hours. The resulting mixture was heated to 80 ℃ and incubated at 80 ℃ for 18 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 4.9 parts of a compound represented by the formula (UVA-A4).

Example 10 preparation of light selective absorption composition (1)

The components were mixed in the following proportions to prepare a light selective absorbing composition (active energy ray-curable resin composition) (1).

70 parts of a polyfunctional acrylate ("A-DPH-12E": manufactured by Ningzhou chemical industries, Ltd.)

Urethane acrylate ("UV-7650B": manufactured by Nippon chemical industries Co., Ltd.) 30 parts

3 parts of a polymerization initiator ("NCI-730": manufactured by ADEKA, Inc.)

2 parts of the Compound represented by formula (UVA-1) synthesized in example 1

Methyl ethyl ketone 34 parts

Example 11 preparation of light selective absorption composition (2)

A light selective absorbing composition (2) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-2).

Example 12 preparation of light selective absorption composition (3)

A light selective absorbing composition (3) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-3).

Example 13 preparation of light Selective absorbing composition (4)

A light selective absorbing composition (4) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-4).

Example 14 preparation of light Selective absorbing composition (5)

A light selective absorbing composition (5) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-5).

Example 15 preparation of light Selective absorbing composition (6)

A light selective absorbing composition (6) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-6).

Example 16 preparation of light Selective absorbing composition (7)

A light selective absorbing composition (7) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-7).

Example 17 preparation of light Selective absorbing composition (8)

A light selective absorbing composition (8) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-8).

Example 18 preparation of light Selective absorbing composition (9)

A light selective absorbing composition (9) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-9).

Preparation example 1 preparation of light selective absorbing composition (A1)

A light selective absorbing composition (a1) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-a 1).

Preparation example 2 preparation of light selective absorbing composition (A2)

A light selective absorbing composition (a2) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-a 2).

Preparation example 3 preparation of light selective absorbing composition (A3)

A light selective absorbing composition (A3) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-a 4).

Example 19 production of film with cured layer (1)

The surface of a resin film [ trade name "ZEONOR", manufactured by japan regen corporation ] made of a cyclic polyolefin resin having a thickness of 23 μm was subjected to corona discharge treatment, and the corona discharge-treated surface was coated with a light selective absorbing composition (6) using a bar coater. The coated film was put into a drying oven and dried at 100 ℃ for 2 minutes. The dried coating film was put into a nitrogen substitution tank, nitrogen was sealed in the tank for 1 minute, and then ultraviolet light was irradiated from the coating surface side to obtain a film (6) with a cured layer. The cured layer had a film thickness of about 6.0 μm.

As the ultraviolet irradiation apparatus, an ultraviolet irradiation apparatus equipped with a belt conveyor was used [ lamp used was "H Lamp (H Bulb)" manufactured by Fusion UV Systems Co., Ltd.) "]To achieve a cumulative light amount of 400mJ/cm²The ultraviolet ray is irradiated in the form of (UVB).

Comparative example 1 production of film with cured layer (A1)

A film with a cured layer (a1) was obtained in the same manner as in example 19, except that the light selective absorbing composition (6) was replaced with the light selective absorbing composition (a 1).

Comparative example 2 production of film with cured layer (A2)

A film with a cured layer (a2) was obtained in the same manner as in example 19, except that the light selective absorbing composition (6) was replaced with the light selective absorbing composition (a 2).

Comparative example 3 production of film with cured layer (A3)

A film with a cured layer (A3) was obtained in the same manner as in example 19, except that the light selective absorbing composition (6) was replaced with the light selective absorbing composition (A3).

< measurement of absorbance of film with cured layer >

The cured layer-bearing film (1) obtained in example 19 was cut into a size of 30mm × 30mm as a sample (1). The obtained sample (1) was bonded to alkali-free glass [ trade name "EAGLE XG" manufactured by corning corporation ] with an acrylic adhesive interposed therebetween to obtain a sample (2). The absorbance of the sample (2) was measured in a wavelength range of 300 to 800nm in units of 1nm step length using a spectrophotometer (UV-2450: manufactured by Shimadzu corporation). The measured absorbance at the wavelength of 395nm and the measured absorbance at the wavelength of 430nm were set as the absorbance at the wavelength of 395nm and the wavelength of 430nm of the film (1) with a cured layer. The results are shown in table 1. The absorbance at 395nm and 430nm of the alkali-free glass was almost 0, the absorbance at 395nm and 430nm of the resin film made of the cyclic polyolefin resin was almost 0, and the absorbance at 395nm and 430nm of the acrylic adhesive was almost 0.

< measurement of the absorbance Retention Rate of film with cured layer >

The sample (2) after the measurement of the absorbance was put into a Sunshine weatherometer (Sunshine weather meter) (manufactured by Suga Test Instruments) for 48 hours under the conditions of a temperature of 63 ℃ and a relative humidity of 50% RH, and a weather resistance Test was performed. The absorbance of the sample (2) after the weather resistance test was measured by the same method as described above. From the measured absorbance, the absorbance retention of the sample (2) at a wavelength of 395nm was determined based on the following formula. The results are shown in Table 1. The closer the absorbance retention rate is to 100, the less the deterioration of the light selective absorption function is exhibited, and the better the weather resistance is exhibited. A (395) represents the absorbance at 395 nm.

Absorbance retention (%) (a (395) after durability test/a (395) before durability test) x 100

The same evaluation as that of the film with a cured layer (1) was carried out using the film with a cured layer (a1), the film with a cured layer (a2), and the film with a cured layer (A3), respectively, instead of the film with a cured layer (1). The results are shown in Table 1.

[ Table 1]

TABLE 1

	Compound (I)	A(395)	A(430)	A(395)/A(430)	Absorbance retention ratio
						Example 19	Formula (UVA-6)	1.24	0.03	40.0	63.9
Comparative example 1	Formula (UVA-A1)	2.08	0.05	40.8	4.9
						Comparative example 2	Formula (UVA-A2)	2.51	0.04	58.3	6.6
Comparative example 3	Formula (UVA-A4)	1.72	0.26	6.7	35.1

Example 20 production of optical film (1)

A resin solution (solid content concentration: 25 mass%) comprising 70 parts of polymethyl methacrylate resin (SUMIPEX MH, manufactured by Sumitomo chemical Co., Ltd.), 30 parts of rubber particles having a particle diameter of 250nm and formed of a core-shell structure of polymethyl methacrylate resin (PMMA)/polybutyl acrylate resin (PBA), 2 parts of a compound represented by the formula (UVA-6) and 2-butanone was put into a mixing tank and stirred to dissolve the respective components.

The resulting dissolved substance was uniformly cast on a glass support using an applicator (applicator), dried in an oven at 40 ℃ for 10 minutes, and then further dried in an oven at 80 ℃ for 10 minutes. After drying, the optical film (1) is peeled from the glass support to obtain an optical film (1) having a light selective absorption ability. The thickness of the dried optical film (1) was 30 μm.

Example 21 production of optical film (2)

A resin solution (solid content concentration: 7 mass%) prepared from 100 parts of cellulose triacetate (degree of substitution with acetyl group: 2.87), 2 parts of a compound represented by formula (UVA-6), and a mixed solution of chloroform and ethanol (mass ratio, chloroform: ethanol: 90: 10) was put into a mixing pot, and the components were dissolved by stirring.

The resulting solution was uniformly cast on a glass support using an applicator, dried in an oven at 40 ℃ for 10 minutes, and then further dried in an oven at 80 ℃ for 10 minutes. After drying, the optical film (2) is peeled from the glass support to obtain an optical film (2) having a light selective absorption ability. The thickness of the dried optical film (2) was 30 μm.

Example 22 production of optical film (3)

A resin solution (solid content concentration: 20 mass%) comprising 100 parts of a cycloolefin polymer resin (manufactured by JSR: ARTON F4520), 2 parts of a compound represented by the formula (UVA-6), and a mixed solution of dichloromethane and toluene (mass ratio, dichloromethane: toluene: 50) was charged into a mixing tank, and the components were dissolved by stirring.

The resulting solution was uniformly cast on a glass support using an applicator, dried in an oven at 40 ℃ for 10 minutes, and then further dried in an oven at 80 ℃ for 10 minutes. After drying, the optical film (3) is peeled from the glass support to obtain an optical film (3) having a light selective absorption ability. The thickness of the dried optical film (3) was 30 μm.

Comparative example 4 production of optical film (4)

An optical film (4) was produced in the same manner as in example 20, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-a 1).

Comparative example 5 production of optical film (5)

An optical film (5) was produced in the same manner as in example 21, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-a 1).

Comparative example 6 production of optical film 6

An optical film (6) was produced in the same manner as in example 20, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-a 4).

Comparative example 7 production of optical film 7

An optical film (7) was produced in the same manner as in example 21, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-a 4).

< measurement of Absorbance of optical film >

After one side of the optical film (1) obtained in example 20 was subjected to corona discharge treatment, an acrylic adhesive was laminated by a laminator and aged at 23 ℃ and 65% RH for 7 days to obtain an optical film (1) with an adhesive. Next, the optical film (1) with an adhesive was cut into a size of 30mm × 30mm, and bonded to alkali-free glass [ trade name "EAGLE XG" manufactured by corning corporation ], to prepare a sample (3). The absorbance of the sample (3) was measured in a unit of 1nm step using a spectrophotometer (UV-2450: manufactured by Shimadzu corporation) in a wavelength range of 300 to 800 nm. The measured absorbances at the wavelength of 395nm and the wavelength of 430nm were set as the absorbances at the wavelength of 395nm and the wavelength of 430nm of the optical film (1). The results are shown in Table 2. The absorbance at 395nm and 430nm of the alkali-free glass was almost 0, and the absorbance at 395nm and 430nm of the acrylic adhesive was almost 0.

The sample (3) after the absorbance measurement was put into a sunshine weatherometer (manufactured by Suga Test Instruments) under the conditions of a temperature of 63 ℃ and a relative humidity of 50% RH, and a weatherometer Test was performed for 200 hours. The absorbance of the sample (3) after the weather resistance test was measured by the same method as described above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 395nm was determined based on the following formula. The results are shown in Table 2. The closer the absorbance retention rate is to 100, the less the deterioration of the light selective absorption function is exhibited, and the better the weather resistance is exhibited.

Absorbance retention (%) (a (395) after durability test/a (395) before durability test) x 100

The same evaluation as that of the optical film (1) was performed using the optical films (2) to (7) instead of the optical film (1). The results are shown in Table 2.

[ Table 2]

TABLE 2

	Compound (I)	Resin composition	A(395)	A(430)	A(395)/A(430)	Absorbance retention ratio
							Example 20	Formula (UVA-6)	Polymethyl methacrylate resin	3.01	0.03	103.8	100.0
Example 21	Formula (UVA-6)	Cellulose acetate resin	3.42	0.03	126.6	95.6
							Example 22	Formula (UVA-6)	Cycloolefin resin	3.26	0.02	163.1	76.3
Comparative example 4	Formula (UVA-A1)	Polymethyl methacrylate resin	3.56	0.02	161.9	11.3
							Comparative example 5	Formula (UVA-A1)	Cellulose acetate resin	3.64	0.04	93.4	3.4
Comparative example 6	Formula (UVA-A4)	Polymethyl methacrylate resin	4.04	0.56	7.2	53.8
							Comparative example 7	Formula (UVA-A4)	Cellulose acetate resin	4.22	0.74	5.7	46.6

Example 23 production of adhesive composition (1)

< preparation of acrylic resin (A) >

A reaction vessel equipped with a condenser, a nitrogen inlet, a thermometer and a stirrer was charged with a mixed solution of 81.8 parts of ethyl acetate as a solvent, 70.4 parts of butyl acrylate, 20.0 parts of methyl acrylate, and 8.0 parts of 2-phenoxyethyl acrylate, 1.0 part of 2-hydroxyethyl acrylate and 0.6 part of acrylic acid as monomers, and the internal temperature was increased to 55 ℃ while the air in the reaction vessel was replaced with nitrogen gas so as not to contain oxygen. Thereafter, a solution of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in an amount of 0.14 part by weight in total. After the initiator was added, the temperature was maintained for 1 hour, ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hour while maintaining the internal temperature at 54 to 56 ℃, the addition of ethyl acetate was stopped when the concentration of the acrylic resin reached 35%, and the temperature was maintained at that temperature from the start of the addition of ethyl acetate to the elapse of 12 hours. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The weight-average molecular weight Mw of the obtained acrylic resin was 142 ten thousand in terms of polystyrene based on GPC, and Mw/Mn was 5.2. This was used as the acrylic resin (A).

< preparation of adhesive composition (1) >

An adhesive composition (1) was obtained by mixing a crosslinking agent (an ethyl acetate solution of trimethylolpropane adduct of toluene diisocyanate (solid content concentration: 75%), 0.5 part of a product name "CORONATE L" manufactured by tokyo co., ltd., 3-glycidoxypropyltrimethoxysilane, a product name "KBM 403" manufactured by shin-Etsu chemical Co., Ltd., and 2.0 parts of a compound represented by the formula (UVA-1) with 100 parts of the solid content of the ethyl acetate solution (1) (resin concentration: 20%) of the acrylic resin (a) synthesized above, and further adding ethyl acetate so that the solid content concentration became 14%. The amount of the crosslinking agent is the mass part based on the active ingredient.

Example 24 preparation of adhesive composition (2)

An adhesive composition (2) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-2).

Example 25 production of adhesive composition (3)

An adhesive composition (3) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-3).

Example 26 production of adhesive composition (4)

An adhesive composition (4) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-4).

Example 27 preparation of adhesive composition (5)

An adhesive composition (5) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-5).

Example 28 production of adhesive composition (6)

An adhesive composition (6) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-6).

Example 29 preparation of adhesive composition (7)

An adhesive composition (7) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-7).

Example 30 production of adhesive composition (8)

An adhesive composition (8) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-8).

Example 31 production of adhesive composition (9)

An adhesive composition (9) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-9).

Comparative example 8 production of adhesive composition (10)

An adhesive composition (10) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-a 1).

Example 32 production of adhesive layer (1) and adhesive sheet (1)

The obtained adhesive composition (6) was applied to a release-treated surface of a release film [ trade name "PLR-382190" available from linec corporation ] formed of a polyethylene terephthalate film, which was subjected to release treatment, using an applicator, and dried at 100 ℃ for 1 minute to prepare an adhesive layer (1). The thickness of the resulting adhesive layer was 15 μm.

The obtained pressure-sensitive adhesive layer (1) was laminated to a 23 μm ultraviolet absorber-containing cycloolefin film [ trade name "ZEONOR" available from japan regen corporation ] by a laminator, and cured at 23 ℃ and a relative humidity of 65% for 7 days to obtain a pressure-sensitive adhesive sheet (1).

Example 33 production of adhesive layer (2) and adhesive sheet (2)

A pressure-sensitive adhesive layer (2) and a pressure-sensitive adhesive sheet (2) were produced in the same manner as in example 32, except that the pressure-sensitive adhesive composition (6) was changed to the pressure-sensitive adhesive composition (7).

Comparative example 9 production of adhesive layer (3) and adhesive sheet (3)

A pressure-sensitive adhesive layer (3) and a pressure-sensitive adhesive sheet (3) were produced in the same manner as in example 32, except that the pressure-sensitive adhesive composition (6) was changed to the pressure-sensitive adhesive composition (10).

< measurement of Absorbance of adhesive sheet >

The obtained adhesive sheet (1) was cut into a size of 30mm × 30mm, and the separator was peeled off, and the adhesive layer (1) was bonded to alkali-free glass [ trade name "EAGLE XG" manufactured by corning corporation ], which was used as a sample (4). The absorbance of the sample (4) was measured in a unit of 1nm step using a spectrophotometer (UV-2450: manufactured by Shimadzu corporation) in a wavelength range of 300 to 800 nm. The measured absorbances at the wavelength of 395nm and the wavelength of 430nm were taken as the absorbances at the wavelength of 395nm and the wavelength of 430nm of the adhesive sheet (1). The results are shown in Table 3. In addition, the absorbance at 395nm and the absorbance at 430nm were 0 in both of the single cycloolefin film and the single alkali-free glass.

< measurement of Absorbance Retention ratio of adhesive sheet >

The sample (4) after the absorbance measurement was put into a sunshine weatherometer (manufactured by Suga Test Instruments) at a temperature of 63 ℃ and a relative humidity of 50% RH for 200 hours to carry out a weather resistance Test. The absorbance of the sample (4) thus taken was measured in the same manner as described above. From the measured absorbance, the absorbance retention of the 395nm sample was determined based on the following formula. The results are shown in Table 3. The closer the absorbance retention rate is to 100, the less the deterioration of the light selective absorption function is exhibited, and the better the weather resistance is exhibited.

Absorbance retention (%) (a (395) after durability test/a (395) before durability test) x 100

The same evaluation as that of the adhesive sheet (1) was performed using the adhesive sheet (2) and the adhesive sheet (3) instead of the adhesive sheet (1). The results are shown in Table 3.

[ Table 3]

TABLE 3

	Compound (I)	A(395)	A(430)	A(395)/A(430)	Absorbance retention ratio
						Example 32	Formula (UVA-6)	1.45	0.01	111.4	100
Example 33	Formula (UVA-7)	1.26	0.03	43.3	99.4
						Comparative example 9	Formula (UVA-A1)	2.82	0.01	216.7	6.8

Example 34 Synthesis of Compound represented by the formula (UVA-10)

Under a nitrogen atmosphere, 2.5 parts of the compound represented by the formula (M-9), 15.1 parts of benzoyl (phenyliodo) (trifluoromethanesulfonyl) methanide, 0.4 part of copper (I) chloride and 100 parts of dioxane were mixed. The resulting mixture was stirred at 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.7 parts of a compound represented by the formula (M-10).

1.5 parts of a compound represented by the formula (M-10), 1.4 parts of methyl trifluoromethanesulfonate and 10 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture were added 1.3 parts of diisopropylethylamine and 0.7 part of malononitrile, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.0 part of a compound represented by the formula (UVA-10).

LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-10) was produced.

¹H-NMR (deuterated DMSO) delta: 1.00(s, 3H), 1.15(s, 3H), 1.86(m, 2H), 2.18(m, 2H), 2.32 to 2.91(m, 4H), 3.50 to 4.20(m, 4H)

LC－MS；[M+H]⁺＝343.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-10) was 384.2 nm. The compound represented by the formula (UVA-10) obtained had an ε (λ max) of 1.29L/(g · cm), an ε (λ max +30nm) of 0.075L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 17.2.

Example 35 Synthesis of Compound represented by formula (UVA-11)

5 parts of a compound represented by the formula (M-6), 4.9 parts of methyl trifluoromethanesulfonate, 3.8 parts of diisopropylethylamine and 10 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture, 5 parts of dimethylamine was added, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 3.1 parts of a compound represented by the formula (UVA-11).

LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-11) was produced.

¹H-NMR (deuterated DMSO) delta: 1.08(s, 6H), 2.42(s, 2H), 2.55(s, 2H), 3.40(m, 6H)

LC－MS；[M+H]⁺＝241.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-11) was 379.4 nm. The compound represented by the formula (UVA-11) obtained had an ε (λ max) of 1.93L/(g · cm), an ε (λ max +30nm) of 0.063L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 30.6.

Example 36 Synthesis of Compound represented by formula (UVA-12)

5 parts of a compound represented by the formula (M-6), 4.9 parts of methyl trifluoromethanesulfonate, 3.8 parts of diisopropylethylamine and 10 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. 8.4 parts of diethylamine was added to the obtained mixture, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 2.9 parts of a compound represented by the formula (UVA-12).

LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-12) was produced.

¹H-NMR (deuterated DMSO) delta: 1.08(s, 6H), 1.39(t, 6H), 2.44(s, 2H), 2.58(s, 2H), 3.74(m, 4H)

LC－MS；[M+H]⁺＝269.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-12) was 380.5 nm. The compound represented by the formula (UVA-12) obtained had an ε (λ max) of 1.75L/(g · cm), an ε (λ max +30nm) of 0.098L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 17.6.

Example 37 Synthesis of Compound represented by the formula (UVA-13)

5 parts of a compound represented by the formula (M-6), 4.9 parts of methyl trifluoromethanesulfonate, 3.8 parts of diisopropylethylamine and 10 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture, 14.8 parts of dibutylamine was added, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 2.5 parts of a compound represented by the formula (UVA-13).

LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-13) was produced.

¹H-NMR (deuterated DMSO) delta: 0.99(t, 6H), 1.07(s, 6H), 1.32 to 1.46(m, 4H), 1.70(m, 4H), 2.40(s, 2H), 2.57(s, 2H), 3.32 to 3.85(m, 4H).

LC－MS；[M+H]⁺＝325.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-13) was 382.8 nm. The compound represented by the formula (UVA-13) obtained had an ε (λ max) of 1.42L/(g · cm), an ε (λ max +30nm) of 0.095L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 14.9.

Example 38 Synthesis of Compound represented by formula (UVA-14)

5 parts of a compound represented by the formula (M-6), 3.6 parts of potassium carbonate, 7.7 parts of methyl trifluoromethanesulfonate and 40 parts of methyl ethyl ketone were mixed under a nitrogen atmosphere, and the mixture was stirred at 0 to 5 ℃ for 4 hours. To the resulting mixture was added 2 parts of azetidine, and the mixture was stirred at 0 to 5 ℃ for 10 minutes. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 2.6 parts of a compound represented by the formula (UVA-14).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-14) was produced.

¹H-NMR (deuterated DMSO) delta: 1.05(s, 6H), 2.14(s, 2H), 2.45 to 2.53(m, 4H), 4.36(t, 2H), 4.91(t, 2H)

LC－MS；[M+H]⁺＝253.3

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-14) was 377.2 nm. The compound represented by the formula (UVA-14) obtained had an ε (λ max) of 1.93L/(g · cm), an ε (λ max +30nm) of 0.028L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 68.9.

Example 39 Synthesis of Compound represented by formula (UVA-15)

4.0 parts of a compound represented by the formula (M-6), 3.7 parts of methyl trifluoromethanesulfonate and 40 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the obtained mixture, 2.9 parts of diisopropylethylamine and 40 parts of a solution (methylamine concentration: 7% by mass) in which methylamine is dissolved in tetrahydrofuran were added, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.9 parts of a compound represented by the formula (UVA-15).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-15) was produced.

¹H-NMR (deuterated DMSO) delta: 0.98(s, 6H), 2.48 to 2.58(m, 4H), 3.03(s, 3H), 9.15(s, 1H)

LC－MS；[M+H]⁺＝226.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-15) was 364.8 nm. The compound represented by the formula (UVA-15) obtained had an ε (λ max) of 1.86L/(g · cm), an ε (λ max +30nm) of 0.066L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 28.2.

Example 40 Synthesis of Compound represented by formula (UVA-16)

4.0 parts of a compound represented by the formula (M-6), 3.7 parts of methyl trifluoromethanesulfonate and 40 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the obtained mixture, 2.9 parts of diisopropylethylamine and 40 parts of a solution (concentration of ethylamine: 10% by mass) of ethylamine dissolved in tetrahydrofuran were added, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.5 parts of a compound represented by the formula (UVA-16).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-16) was produced.

¹H-NMR (deuterated DMSO) delta: 0.98(s, 6H), 2.48 to 2.58(m, 4H), 3.03(t, 3H), 4.21(m, 2H), 9.15(s, 1H)

LC－MS；[M+H]⁺＝240.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-16) was 364.8 nm. The compound represented by the formula (UVA-16) obtained had an ε (λ max) of 1.80L/(g · cm), an ε (λ max +30nm) of 0.074L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 24.4.

Example 41 Synthesis of Compound represented by formula (UVA-17)

1.7 parts of a compound represented by the formula (M-6), 1.6 parts of methyl trifluoromethanesulfonate and 17 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the obtained mixture, 1.2 parts of diisopropylethylamine and 100 parts of a solution (molar concentration of ammonia; 0.4 mol%) obtained by dissolving ammonia in tetrahydrofuran were added, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 0.7 part of a compound represented by the formula (UVA-17).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-17) was produced.

¹H-NMR (deuterated DMSO) delta: 0.98(s, 6H), 2.48 to 2.58(m, 4H), 9.15(m, 2H)

LC－MS；[M+H]⁺＝213.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-17) was 352.6 nm. The compound represented by the formula (UVA-17) obtained had an ε (λ max) of 1.75L/(g · cm), an ε (λ max +30nm) of 0.11L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 15.9.

Example 42 Synthesis of Compound represented by formula (UVA-18)

3.5 parts of a compound represented by the formula (M-6), 3.2 parts of methyl trifluoromethanesulfonate and 35 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture were added 2.2 parts of potassium carbonate and 0.8 part of N, N' -dimethylethylenediamine, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 0.4 part of a compound represented by the formula (UVA-18).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-18) was produced.

¹H-NMR (deuterated DMSO) delta: 0.98(s, 12H), 2.67(m, 4H), 3.44(m, 8H), 4.05(m, 6H)

LC－MS；[M+H]⁺＝479.7

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-18) was 391.4 nm. The compound represented by the formula (UVA-18) obtained had an ε (λ max) of 1.52L/(g · cm), an ε (λ max +30nm) of 0.036L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 42.2.

Example 43 Synthesis of Compound represented by formula (UVA-19)

3.5 parts of a compound represented by the formula (M-6), 3.2 parts of methyl trifluoromethanesulfonate and 35 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture were added 2.2 parts of potassium carbonate and 1.0 part of N, N' -dimethyltrimethylene diamine, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 0.2 part of a compound represented by the formula (UVA-19).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-19) was produced.

¹H-NMR (deuterated DMSO) delta: 0.99(s, 12H), 2.50(m, 8H), 2.66(m, 6H), 3.32(m, 6H)

LC－MS；[M+H]⁺＝493.7

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-19) was 384.9 nm. The compound represented by the formula (UVA-19) obtained had an ε (λ max) of 1.63L/(g · cm), an ε (λ max +30nm) of 0.036L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 45.3.

Example 44 preparation of light Selective absorbing composition (10)

A light selective absorbing composition (10) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-10).

Example 45 preparation of light Selective absorbing composition (11)

A light selective absorbing composition (11) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-11).

Example 46 preparation of light Selective absorbing composition (12)

A light selective absorbing composition (12) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-12).

Example 47 preparation of light Selective absorbing composition (13)

A light selective absorbing composition (13) was prepared in the same manner as in example 10, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-13).

Example 48 production of film (2) with cured layer

A film (2) with a cured layer was obtained in the same manner as in example 19, except that the light selective absorbing composition (1) was replaced with the light selective absorbing composition (11).

Example 49 production of film (3) with cured layer

A film (3) with a cured layer was obtained in the same manner as in example 19, except that the light selective absorbing composition (1) was replaced with the light selective absorbing composition (12).

< measurement of absorbance and measurement of Absorbance Retention Rate of cured layer-bearing film >

The absorbance was measured in the same manner as in the above-described < absorbance measurement of film with a cured layer > except that the film with a cured layer (2) and the film with a cured layer (3) were used instead of the film with a cured layer (1).

The absorbance retention ratios of the cured layer-attached film (1) obtained in example 19 and the cured layer-attached film (a3) obtained in comparative example 3 were measured in the same manner as in the above-described measurement of the absorbance retention ratio of the cured layer-attached film, except that the time of putting the cured layer-attached film in the solar weatherometer was 75 hours.

The absorbance retention rate was measured in the same manner as the above-described measurement of the absorbance retention rate of the film with a cured layer > except that the film with a cured layer (2) and the film with a cured layer (3) were used instead of the film with a cured layer (1) and the time of input to the sunshine weatherometer was 75 hours.

These results are shown in table 4. Table 4 also shows the values of absorbance of the cured layer-bearing film (1) obtained in example 19 and the cured layer-bearing film (a3) obtained in comparative example 3.

[ Table 4]

TABLE 4

	Compound (I)	A(395)	A(430)	A(395)/A(430)	Absorbance retention ratio
						Example 48	Formula (UVA-11)	1.199	0.044	27.3	56
Example 49	Formula (UVA-12)	1.163	0.022	52.9	54
						Example 19	Formula (UVA-6)	1.24	0.03	40.0	39.8
Comparative example 3	Formula (UVA-A4)	1.72	0.26	6.7	7.1

Example 50 production of adhesive composition (11)

An adhesive composition (11) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-10).

Example 51 production of adhesive composition (12)

An adhesive composition (12) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-11).

Example 52 production of adhesive composition (13)

An adhesive composition (13) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-12).

Example 53 production of adhesive composition (14)

An adhesive composition (14) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-13).

Example 54 production of adhesive layer (4) and adhesive sheet (4)

A pressure-sensitive adhesive layer (4) and a pressure-sensitive adhesive sheet (4) were produced in the same manner as in example 32, except that the pressure-sensitive adhesive composition (6) was changed to the pressure-sensitive adhesive composition (9).

Example 55 production of adhesive layer (5) and adhesive sheet (5)

A pressure-sensitive adhesive layer (5) and a pressure-sensitive adhesive sheet (5) were produced in the same manner as in example 32, except that the pressure-sensitive adhesive composition (6) was changed to the pressure-sensitive adhesive composition (11).

Example 56 production of adhesive layer (6) and adhesive sheet (6)

A pressure-sensitive adhesive layer (6) and a pressure-sensitive adhesive sheet (6) were produced in the same manner as in example 32, except that the pressure-sensitive adhesive composition (6) was changed to the pressure-sensitive adhesive composition (12).

Example 57 production of adhesive layer (7) and adhesive sheet (7)

A pressure-sensitive adhesive layer (7) and a pressure-sensitive adhesive sheet (7) were produced in the same manner as in example 32, except that the pressure-sensitive adhesive composition (6) was changed to the pressure-sensitive adhesive composition (13).

Example 58 production of adhesive layer (8) and adhesive sheet (8)

A pressure-sensitive adhesive layer (8) and a pressure-sensitive adhesive sheet (8) were produced in the same manner as in example 32, except that the pressure-sensitive adhesive composition (6) was changed to the pressure-sensitive adhesive composition (14).

Example 59 preparation of adhesive composition (15)

A pressure-sensitive adhesive composition (15) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-18), and the content thereof was changed to 1.0 part by mass based on 100 parts by mass of the acrylic resin (a).

Example 60 production of adhesive layer (9) and adhesive sheet (9)

A pressure-sensitive adhesive layer (9) and a pressure-sensitive adhesive sheet (9) were produced in the same manner as in example 32, except that the pressure-sensitive adhesive composition (6) was changed to the pressure-sensitive adhesive composition (15).

< measurement of Absorbance and Absorbance Retention of adhesive sheet >

The absorbance and the absorbance retention rate were measured in the same manner as in the above-described < measurement of absorbance of adhesive sheet > and < measurement of absorbance retention rate of adhesive sheet > except that the adhesive sheets (4) to (9) were used instead of the adhesive sheet (1). The results are shown in Table 5.

[ Table 5]

TABLE 5

	Compound (I)	A(395)	A(430)	A(395)/A(430)	Absorbance retention ratio
						Example 54	Formula (UVA-9)	3.18	0.025	127.4	96.2
Example 55	Formula (UVA-10)	2.35	0.031	75.9	84.8
						Example 56	Formula (UVA-11)	2.02	0.009	224.3	98.9
Example 57	Formula (UVA-12)	2.29	0.014	163.9	98.2
						Example 58	Formula (UVA-13)	0.97	0.001	974.0	85.8
Example 60	Formula (UVA-18)	2.16	0.200	10.8	72.8

Example 61 Synthesis of Compound represented by formula (UVA-20)

17 parts of the compound represented by the formula (M-3), 12.2 parts of potassium carbonate, 15.9 parts of 1-chloromethyl-4-fluoro-1, 4-diaza-cationic bicyclo [2.2.2] octanebis (tetrafluoroborate) (registered trademark of Selectfluor, Air Products and Chemicals) and 85 parts of methyl ethyl ketone were mixed under a nitrogen atmosphere, and stirred in an ice bath for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 3.7 parts of a compound represented by the formula (M-11).

18 parts of a compound represented by the formula (M-11), 28 parts of methyl trifluoromethanesulfonate and 90 parts of methyl ethyl ketone were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 3 hours. To the resulting mixture were added 13.0 parts of potassium carbonate and 8.4 parts of malononitrile, and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 5.8 parts of a compound represented by the formula (UVA-20).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-20) was produced.

¹H-NMR (deuterated DMSO) delta: 1.08(s, 6H), 1.97(m, 4H), 2.40(d, 2H), 2.50(d, 2H), 3.53(m, 2H), 3.86(m, 2H)

LC－MS；[M+H]⁺＝260.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-20) was 407.5 nm. The compound represented by the formula (UVA-20) obtained had an ε (λ max) of 2.30L/(g · cm), an ε (λ max +30nm) of 0.041L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 56.0.

Example 62 Synthesis of Compound represented by formula (UVA-21)

5 parts of 3-hydroxypiperidine, 13.6 parts of tert-butyldiphenylchlorosilane, 6.7 parts of imidazole and 40 parts of dichloromethane are mixed under a nitrogen atmosphere, and stirred at 20-30 ℃ for 4 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 10.5 parts of a compound represented by the formula (M-12).

4.0 parts of a compound represented by the formula (M-6), 3.2 parts of diisopropylethylamine, 4.0 parts of methyl trifluoromethanesulfonate and 80 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 4 hours. To the resulting mixture was added 8.3 parts of the compound represented by formula (M-12), and the mixture was stirred at 20 to 30 ℃ for 3 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 6.5 parts of a compound represented by the formula (UVA-21).

Performing LC-MS measurementAnd¹H-NMR analysis confirmed that the compound represented by the formula (UVA-21) was produced.

¹H-NMR (deuterated DMSO) delta: 0.97(s, 6H), 1.04(s, 9H), 1.70(m, 2H), 1.85(m, 2H), 2.48(s, 2H), 2.65(s, 2H), 3.72(m, 2H), 3.94(m, 2H), 4.13(m, 1H), 7.42 to 7.52(m, 6H), 7.61 to 7.64(m, 4H)

LC－MS；[M+H]⁺＝535.9

Example 63 Synthesis of Compound represented by formula (UVA-22)

4.2 parts of a compound represented by the formula (UVA-21) and 50 parts of a tetrabutylammonium fluoride/tetrahydrofuran 1M solution were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 40 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.8 parts of a compound represented by the formula (UVA-22).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-22) was produced.

¹H-NMR (deuterated DMSO) delta: 0.98(s, 6H), 1.59(m, 2H), 1.92(m, 2H), 2.67(s, 2H), 3.68-3.95 (m, 4H), 4.97(m, 1H)

LC－MS；[M+H]⁺＝297.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-21) was 384.6 nm. The compound represented by the formula (UVA-21) obtained had an ε (λ max) of 1.43L/(g · cm), an ε (λ max +30nm) of 0.085L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 16.8.

Example 64 Synthesis of Compound represented by the formula (UVA-23)

5.0 parts of a compound represented by the formula (M-6), 3.6 parts of potassium carbonate, 7.7 parts of methyl trifluoromethanesulfonate and 40 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 4 hours. To the resulting mixture was added 2.0 parts of azetidine, and the mixture was stirred at 20 to 30 ℃ for 4 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 2.3 parts of a compound represented by the formula (UVA-23).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-23) was produced.

¹H-NMR (deuterated DMSO) delta: 1.05(s, 6H), 2.14(s, 2H), 2.44 ~ 2.53(m, 4H), 4.36(t, 2H), 4.91(t, 2H)

LC－MS；[M+H]⁺＝253.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-23) was 377.2 nm. The compound represented by the formula (UVA-23) obtained had an ε (λ max) of 1.93L/(g · cm), an ε (λ max +30nm) of 0.028L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 68.9.

Example 65 Synthesis of Compound represented by formula (UVA-24)

2.5 parts of a compound represented by the formula (M-6), 1.6 parts of potassium carbonate, 2.3 parts of methyl trifluoromethanesulfonate and 25 parts of acetonitrile were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 4 hours. To the resulting mixture, 0.6 part of piperazine was added, and the mixture was stirred at 20 to 30 ℃ for 4 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.0 part of a compound represented by the formula (UVA-24).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-24) was produced.

¹H-NMR (deuterated DMSO) delta: 0.93(s, 2H), 1.01(s, 12H), 1.24(s, 2H), 2.65(s, 4H), 4.09(m, 8H)

LC－MS；[M+H]⁺＝477.5

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-24) was 390.5 nm. The compound represented by the formula (UVA-24) obtained had an ε (λ max) of 1.92L/(g · cm), an ε (λ max +30nm) of 0.033L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 58.2.

Example 66 Synthesis of Compound represented by formula (UVA-25)

2.5 parts of a compound represented by the formula (M-6), 1.6 parts of potassium carbonate, 2.3 parts of methyl trifluoromethanesulfonate and 25 parts of methyl ethyl ketone were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 4 hours. To the resulting mixture, 1.0 part of 1, 4-bis (aminomethyl) cyclohexane was added, and the mixture was stirred at 20 to 30 ℃ for 4 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 1.0 part of a compound represented by the formula (UVA-25).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-25) was produced.

¹H-NMR (deuterated DMSO) delta: 0.98(m, 12H), 1.38 to 1.78(m, 10H), 2.67(m, 6H), 3.40(m, 2H), 9.15(m, 2H)

LC－MS；[M+H]⁺＝533.6

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-25) was 372.7 nm. The compound represented by the formula (UVA-25) obtained had an ε (λ max) of 1.59L/(g · cm), an ε (λ max +30nm) of 0.036L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 44.1.

Example 67 Synthesis of Compound represented by formula (UVA-26)

2.5 parts of a compound represented by the formula (M-6), 1.6 parts of potassium carbonate, 2.3 parts of methyl trifluoromethanesulfonate and 25 parts of methyl ethyl ketone were mixed under a nitrogen atmosphere, and the mixture was stirred at 20 to 30 ℃ for 4 hours. To the resulting mixture, 0.8 part of 1, 2-bis (ethylamino) ethane was added, and the mixture was stirred at 20 to 30 ℃ for 4 hours. The solvent was distilled off from the obtained mixture, and purification was performed to obtain 0.9 part of a compound represented by the formula (UVA-26).

Performing LC-MS measurements and¹H-NMR analysis confirmed that the compound represented by the formula (UVA-26) was produced.

¹H-NMR (deuterated DMSO) delta: 1.00(s, 12H), 1.29(t, 6H), 2.56(s, 4H), 2.70(s, 4H), 3.85(m, 4H), 4.05(m, 4H)

LC－MS；[M+H]⁺＝507.7

Further, the maximum absorption wavelength and molar absorption coefficient were measured in the same manner as above. The maximum absorption wavelength of the obtained compound represented by the formula (UVA-26) was 390.7 nm. The compound represented by the formula (UVA-26) obtained had an ε (λ max) of 1.30L/(g · cm), an ε (λ max +30nm) of 0.048L/(g · cm) and an ε (λ max)/ε (λ max +30nm) of 27.1.

EXAMPLE 68 preparation of adhesive composition (16)

An adhesive composition (16) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-23), and the content thereof was changed to 0.5 parts by weight based on 100 parts by weight of the acrylic resin (a).

EXAMPLE 69 preparation of adhesive composition (17)

An adhesive composition (17) was obtained in the same manner as in example 23, except that the compound represented by the formula (UVA-1) was changed to the compound represented by the formula (UVA-26), and the content thereof was changed to 0.2 parts by weight based on 100 parts by weight of the acrylic resin (a).

Example 70 production of adhesive layer (10) and adhesive sheet (10)

An adhesive layer (10) and an adhesive sheet (10) were produced in the same manner as in example 32, except that the adhesive composition (6) was changed to the adhesive composition (16).

Example 71 production of adhesive layer (11) and adhesive sheet (11)

A pressure-sensitive adhesive layer (11) and a pressure-sensitive adhesive sheet (11) were produced in the same manner as in example 32, except that the pressure-sensitive adhesive composition (6) was changed to the pressure-sensitive adhesive composition (17).

< measurement of Absorbance and Absorbance Retention of adhesive sheet >

The absorbance and the absorbance retention rate were measured in the same manner as in the above < measurement of absorbance of adhesive sheet > and < measurement of absorbance retention rate of adhesive sheet > except that the adhesive sheet (10) and the adhesive sheet (11) were used instead of the adhesive sheet (1). The results are shown in Table 6.

[ Table 6]

TABLE 6

	Compound (I)	A(395)	A(430)	A(395)/A(430)	Absorbance retention ratio
						Example 70	Formula (UVA-23)	0.78	0.001	778.0	99.6
Example 71	Formula (U)VA-26)	1.15	0.309	3.7	62.2

Example 72 preparation of adhesive composition (18)

< preparation of acrylic resin (A-2) >

A mixed solution of 81.8 parts of ethyl acetate as a solvent, 96 parts of butyl acrylate as a monomer, 3 parts of 2-hydroxyethyl acrylate and 1 part of acrylic acid was charged into a reaction vessel equipped with a condenser, a nitrogen inlet, a thermometer and a stirrer, and the internal temperature was raised to 55 ℃ while replacing the air in the reaction vessel with nitrogen gas so as not to contain oxygen. Thereafter, a solution of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in an amount of 0.14 part by weight in total. After the initiator was added, the temperature was maintained for 1 hour, ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hour while maintaining the internal temperature at 54 to 56 ℃, the addition of ethyl acetate was stopped when the concentration of the acrylic resin reached 35%, and the temperature was maintained at that temperature from the start of the addition of ethyl acetate to the elapse of 12 hours. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The weight average molecular weight Mw of the obtained acrylic resin was 140 ten thousand in terms of polystyrene based on GPC. Mw/Mn was 4.8. This was used as the acrylic resin (A-2).

< preparation of adhesive composition (18) >

An adhesive composition (18) was obtained by mixing a crosslinking agent (ethyl acetate solution of trimethylolpropane adduct of toluene diisocyanate (solid content concentration 75%), 0.5 part of a trade name "CORONATE L" manufactured by tokyo co., ltd., a product of 1, 6-bis (trimethoxysilyl) hexane, 0.3 part of a trade name "KBM 3066" manufactured by shin-Etsu chemical industries, and 3 parts of a compound represented by the formula (UVA-6) with 100 parts of the solid content of the ethyl acetate solution (resin concentration: 20%) of the acrylic resin (a-2) synthesized above, and further adding ethyl acetate so that the solid content concentration became 14%. The amount of the crosslinking agent is the mass part based on the active ingredient.

Example 73 production of adhesive composition (19)

< preparation of acrylic resin (A-3) >

A reaction vessel equipped with a condenser, a nitrogen inlet, a thermometer and a stirrer was charged with a mixed solution of 81.8 parts of ethyl acetate as a solvent, 60 parts of methyl acrylate as a monomer, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 20 parts of 2-phenoxyethyl acrylate, and the internal temperature was raised to 55 ℃ while the atmosphere in the reaction vessel was replaced with nitrogen gas so as not to contain oxygen. Thereafter, a solution of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in an amount of 0.14 part by weight in total. After the initiator was added, the temperature was maintained for 1 hour, ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hour while maintaining the internal temperature at 54 to 56 ℃, the addition of ethyl acetate was stopped when the concentration of the acrylic resin reached 35%, and the temperature was maintained at that temperature from the start of the addition of ethyl acetate to the elapse of 12 hours. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The weight average molecular weight Mw of the obtained acrylic resin was 92 ten thousand in terms of polystyrene based on GPC. Mw/Mn was 7.8. This was used as the acrylic resin (A-3).

< preparation of adhesive composition (19) >

An adhesive composition (19) was obtained in the same manner as in example 72, except that the acrylic resin (a-3) synthesized above was used in place of the acrylic resin (a-2).

Example 74 production of adhesive composition (20)

< preparation of acrylic resin (A-4) >

A reaction vessel equipped with a condenser, a nitrogen inlet, a thermometer and a stirrer was charged with a mixed solution of 81.8 parts of ethyl acetate as a solvent, 10 parts of butyl acrylate, 60 parts of methyl acrylate, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 10 parts of 2-phenoxyethyl acrylate as monomers, and the internal temperature was increased to 55 ℃ while replacing the air in the reaction vessel with nitrogen gas so as not to contain oxygen. Thereafter, a solution of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in an amount of 0.14 part by weight in total. After the initiator was added, the temperature was maintained for 1 hour, ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hour while maintaining the internal temperature at 54 to 56 ℃, the addition of ethyl acetate was stopped when the concentration of the acrylic resin reached 35%, and the temperature was maintained at that temperature from the start of the addition of ethyl acetate to the elapse of 12 hours. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The weight average molecular weight Mw of the obtained acrylic resin was 94 ten thousand in terms of polystyrene based on GPC. Mw/Mn was 8.5. This was used as the acrylic resin (A-4).

< preparation of adhesive composition (20) >

An adhesive composition (20) was obtained in the same manner as in example 72, except that the acrylic resin (a-4) synthesized above was used in place of the acrylic resin (a-2).

Example 75 production of adhesive composition (21)

< preparation of acrylic resin (A-5) >

A reaction vessel equipped with a condenser, a nitrogen inlet, a thermometer and a stirrer was charged with a mixed solution of 81.8 parts of ethyl acetate as a solvent, 20 parts of butyl acrylate, 50 parts of methyl acrylate, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 10 parts of 2-phenoxyethyl acrylate as monomers, and the internal temperature was increased to 55 ℃ while replacing the air in the reaction vessel with nitrogen gas so as not to contain oxygen. Thereafter, a solution of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in an amount of 0.14 part by weight in total. After the initiator was added, the temperature was maintained for 1 hour, ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hour while maintaining the internal temperature at 54 to 56 ℃, the addition of ethyl acetate was stopped when the concentration of the acrylic resin reached 35%, and the temperature was maintained at that temperature from the start of the addition of ethyl acetate to the elapse of 12 hours. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The weight average molecular weight Mw of the obtained acrylic resin was 91 ten thousand in terms of polystyrene based on GPC. This was used as the acrylic resin (A-5).

< preparation of adhesive composition (21) >

An adhesive composition (21) was obtained in the same manner as in example 72, except that the acrylic resin (a-5) synthesized above was used in place of the acrylic resin (a-2).

EXAMPLE 76 preparation of adhesive composition (22)

< preparation of acrylic resin (A-6)

A reaction vessel equipped with a condenser, a nitrogen inlet, a thermometer and a stirrer was charged with a mixed solution of 81.8 parts of ethyl acetate as a solvent, 50 parts of butyl acrylate, 10 parts of methyl acrylate, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 20 parts of 2-phenoxyethyl acrylate as monomers, and the internal temperature was increased to 55 ℃ while replacing the air in the reaction vessel with nitrogen gas so as not to contain oxygen. Thereafter, a solution of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in an amount of 0.14 part by weight in total. After the initiator was added, the temperature was maintained for 1 hour, ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hour while maintaining the internal temperature at 54 to 56 ℃, the addition of ethyl acetate was stopped when the concentration of the acrylic resin reached 35%, and the temperature was maintained at that temperature from the start of the addition of ethyl acetate to the elapse of 12 hours. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The weight average molecular weight Mw of the obtained acrylic resin was 120 ten thousand in terms of polystyrene based on GPC. This was designated as acrylic resin (A-6).

< preparation of adhesive composition (22) >

An adhesive composition (22) was obtained in the same manner as in example 72 except that the acrylic resin (a-6) synthesized above was used in place of the acrylic resin (a-2).

Example 77 preparation of adhesive composition 23

< preparation of acrylic resin (A-7) >

A reaction vessel equipped with a condenser, a nitrogen inlet, a thermometer and a stirrer was charged with a mixed solution of 81.8 parts of ethyl acetate as a solvent, 60 parts of butyl acrylate, 10 parts of methyl acrylate, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 10 parts of 2-phenoxyethyl acrylate as monomers, and the internal temperature was increased to 55 ℃ while replacing the air in the reaction vessel with nitrogen gas so as not to contain oxygen. Thereafter, a solution of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in an amount of 0.14 part by weight in total. After the initiator was added, the temperature was maintained for 1 hour, ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hour while maintaining the internal temperature at 54 to 56 ℃, the addition of ethyl acetate was stopped when the concentration of the acrylic resin reached 35%, and the temperature was maintained at that temperature from the start of the addition of ethyl acetate to the elapse of 12 hours. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The weight average molecular weight Mw of the obtained acrylic resin was 118 ten thousand in terms of polystyrene based on GPC. This was used as an acrylic resin (A-7).

< preparation of adhesive composition (23) >

An adhesive composition (23) was obtained in the same manner as in example 72 except that the acrylic resin (a-7) synthesized above was used in place of the acrylic resin (a-2).

Example 78 preparation of adhesive composition (24)

< preparation of acrylic resin (A-8) >

A reaction vessel equipped with a condenser, a nitrogen inlet, a thermometer and a stirrer was charged with a mixed solution of 81.8 parts of ethyl acetate as a solvent, 70 parts of butyl acrylate as a monomer, 10 parts of 2-hydroxyethyl acrylate, 10 parts of acrylic acid and 10 parts of 2-phenoxyethyl acrylate, and the internal temperature was raised to 55 ℃ while the atmosphere in the reaction vessel was replaced with nitrogen gas so as not to contain oxygen. Thereafter, a solution of azobisisobutyronitrile (polymerization initiator) in 10 parts of ethyl acetate was added in an amount of 0.14 part by weight in total. After the initiator was added, the temperature was maintained for 1 hour, ethyl acetate was continuously added into the reaction vessel at an addition rate of 17.3 parts/hour while maintaining the internal temperature at 54 to 56 ℃, the addition of ethyl acetate was stopped when the concentration of the acrylic resin reached 35%, and the temperature was maintained at that temperature from the start of the addition of ethyl acetate to the elapse of 12 hours. Finally, ethyl acetate was added to adjust the concentration of the acrylic resin to 20%, to prepare an ethyl acetate solution of the acrylic resin. The weight average molecular weight Mw of the obtained acrylic resin was 110 ten thousand in terms of polystyrene based on GPC. This was used as an acrylic resin (A-8).

< preparation of adhesive composition (24) >

An adhesive composition (23) was obtained in the same manner as in example 72 except that the acrylic resin (a-8) synthesized above was used in place of the acrylic resin (a-2).

< evaluation of crystallization of adhesive layer (bleed-out resistance) >

The pressure-sensitive adhesive composition (18) was applied to a release-treated surface of a release film (obtained from linetec corporation under the trade name "PLR-382190") formed of a polyethylene terephthalate film, which had been subjected to release treatment, using an applicator, and dried at 100 ℃ for 1 minute to prepare a pressure-sensitive adhesive layer. And a separator was laminated on the other surface of the pressure-sensitive adhesive layer to obtain a pressure-sensitive adhesive layer of a double-sided separator. The thickness of the resulting adhesive layer was 15 μm.

The adhesive layer of the obtained double-sided separator was cured at 23 ℃ and 65% relative humidity for 7 days. The pressure-sensitive adhesive layer of the cured double-sided tape separator was checked for the presence or absence of crystal deposition of the in-plane compound using a microscope. The case where no crystal was precipitated was evaluated as "a", and the case where crystal was precipitated was evaluated as "b". The evaluation results are shown in the column of "after aging" in table 7.

The pressure-sensitive adhesive layer of the obtained double-sided separator was stored in air at a temperature of 40 ℃ for 1 month. The pressure-sensitive adhesive layer of the double-sided tape separator after storage was checked by using a microscope to see whether or not the compound was crystallized in the surface. The case where no crystal was precipitated was evaluated as "a", and the case where crystal was precipitated was evaluated as "b". The evaluation results are shown in Table 7 under the column "1M at 40 ℃.

The presence or absence of crystal precipitation was confirmed in the same manner as except that the pressure-sensitive adhesive composition (18) was replaced with each of the pressure-sensitive adhesive compositions (19) to (24). The results are shown in Table 7.

[ Table 7]

TABLE 7

Example 79 production of adhesive layer (12) and adhesive sheet (12)

The obtained adhesive composition (18) was applied to a release-treated surface of a release film [ trade name "PLR-382190" available from linec corporation ] formed of a polyethylene terephthalate film, which was subjected to release treatment, using an applicator, and dried at 100 ℃ for 1 minute to prepare an adhesive layer (12). The thickness of the resulting adhesive layer was 15 μm.

The obtained pressure-sensitive adhesive layer (12) was laminated to a 23 μm cycloolefin film containing no ultraviolet absorber by a laminator, and then aged at a temperature of 23 ℃ and a relative humidity of 65% for 7 days to obtain a pressure-sensitive adhesive sheet (12).

Example 80 production of adhesive layer (13) and adhesive sheet (13)

A pressure-sensitive adhesive layer (13) and a pressure-sensitive adhesive sheet (13) were produced in the same manner as in example 79, except that the pressure-sensitive adhesive composition (18) was changed to the pressure-sensitive adhesive composition (19).

Example 81 production of adhesive layer (14) and adhesive sheet (14)

A pressure-sensitive adhesive layer (14) and a pressure-sensitive adhesive sheet (14) were produced in the same manner as in example 79, except that the pressure-sensitive adhesive composition (18) was changed to the pressure-sensitive adhesive composition (20).

Example 82 production of adhesive layer (15) and adhesive sheet (15)

A pressure-sensitive adhesive layer (15) and a pressure-sensitive adhesive sheet (15) were produced in the same manner as in example 79, except that the pressure-sensitive adhesive composition (18) was changed to the pressure-sensitive adhesive composition (21).

Example 83 production of adhesive layer (16) and adhesive sheet (16)

A pressure-sensitive adhesive layer (16) and a pressure-sensitive adhesive sheet (16) were produced in the same manner as in example 79, except that the pressure-sensitive adhesive composition (18) was changed to the pressure-sensitive adhesive composition (22).

Example 84 production of adhesive layer 17 and adhesive sheet 17

A pressure-sensitive adhesive layer (17) and a pressure-sensitive adhesive sheet (17) were produced in the same manner as in example 79, except that the pressure-sensitive adhesive composition (18) was changed to the pressure-sensitive adhesive composition (23).

Example 85 production of adhesive layer (18) and adhesive sheet (18)

A pressure-sensitive adhesive layer (18) and a pressure-sensitive adhesive sheet (18) were produced in the same manner as in example 79, except that the pressure-sensitive adhesive composition (18) was changed to the pressure-sensitive adhesive composition (24).

< measurement of Absorbance Retention ratio of adhesive sheet >

The obtained adhesive sheet (12) was cut into a size of 30mm × 30mm, and the separator was peeled off, and the adhesive layer (12) was bonded to alkali-free glass [ trade name "EAGLE XG" manufactured by corning corporation ], which was used as a sample (5). The absorbance of the sample (5) was measured in a unit of 1nm step using a spectrophotometer (UV-2450: manufactured by Shimadzu corporation) in a wavelength range of 300 to 800 nm. The absorbance at the wavelength of 400nm was measured as the absorbance at the wavelength of 400nm of the pressure-sensitive adhesive sheet (12). The results are shown in Table 8. In addition, the absorbance at a wavelength of 400nm was 0 in both of the single cycloolefin film and the single alkali-free glass.

The sample (5) after the absorbance measurement was put into a sunshine weatherometer (manufactured by Suga Test Instruments) at a temperature of 63 ℃ and a relative humidity of 50% RH for 150 hours to perform a weatherometer Test. The absorbance of the sample (5) taken out was measured by the same method as described above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 400nm was determined based on the following formula. The results are shown in Table 8. The closer the absorbance retention rate is to 100, the less the deterioration of the light selective absorption function is exhibited, and the better the weather resistance is exhibited.

The absorbance retention ratio of the sample (5) was also determined by placing the sample in a sunshine weatherometer (manufactured by Suga Test Instruments) at a temperature of 63 ℃ and a relative humidity of 50% RH for 225 hours.

Absorbance retention (%) (a (400) after durability test/a (400) before durability test) x 100

The absorbance retention was measured in the same manner as in the case where the pressure-sensitive adhesive sheet (12) was replaced with the pressure-sensitive adhesive sheets (13) to (18). The results are shown in Table 8.

[ Table 8]

TABLE 8

EXAMPLE 86 production of adhesive sheet (19)

An adhesive sheet (19) was produced in the same manner as in example 79, except that the 23 μm cycloolefin film containing no ultraviolet absorber was changed to the 23 μm cycloolefin film containing an ultraviolet absorber.

Example 87 production of adhesive sheet (20)

An adhesive sheet (20) was produced in the same manner as in example 80, except that the 23 μm uv-absorbent-free cycloolefin film was changed to the 23 μm uv-absorbent-containing cycloolefin film.

Example 88 production of adhesive sheet (21)

An adhesive sheet (21) was produced in the same manner as in example 81, except that the 23 μm cycloolefin film containing no ultraviolet absorber was changed to the 23 μm cycloolefin film containing an ultraviolet absorber.

EXAMPLE 89 production of adhesive sheet (22)

An adhesive sheet (22) was produced in the same manner as in example 82, except that the 23 μm cycloolefin film containing no ultraviolet absorber was changed to the 23 μm cycloolefin film containing an ultraviolet absorber.

Example 90 production of adhesive sheet (23)

An adhesive sheet (23) was produced in the same manner as in example 83, except that the 23 μm cycloolefin film containing no ultraviolet absorber was changed to the 23 μm cycloolefin film containing an ultraviolet absorber.

Example 91 production of adhesive sheet (24)

An adhesive sheet (24) was produced in the same manner as in example 84, except that the 23 μm cycloolefin film containing no ultraviolet absorber was changed to the 23 μm cycloolefin film containing an ultraviolet absorber.

Example 92 production of adhesive sheet (25)

An adhesive sheet (25) was produced in the same manner as in example 85, except that the 23 μm cycloolefin film containing no ultraviolet absorber was changed to the 23 μm cycloolefin film containing an ultraviolet absorber.

< measurement of Absorbance Retention ratio of adhesive sheet >

The obtained adhesive sheet (19) was cut into a size of 30mm × 30mm, and the separator was peeled off, and the adhesive layer (19) was bonded to alkali-free glass [ trade name "EAGLE XG" manufactured by corning corporation ], which was used as a sample (6). The absorbance of the sample (5) was measured in a unit of 1nm step using a spectrophotometer (UV-2450: manufactured by Shimadzu corporation) in a wavelength range of 300 to 800 nm. The absorbance at a wavelength of 405nm thus measured was defined as the absorbance at a wavelength of 405nm of the adhesive sheet (19). The results are shown in Table 9. The absorbance of a single alkali-free glass and a single cycloolefin film at a wavelength of 405nm was 0.

The sample (6) after the absorbance measurement was put into a sunshine weatherometer (manufactured by Suga Test Instruments) at a temperature of 63 ℃ and a relative humidity of 50% RH for 150 hours to carry out a weather resistance Test. The absorbance of the sample (5) taken out was measured by the same method as described above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 405nm was determined based on the following formula. The results are shown in Table 9. The closer the absorbance retention rate is to 100, the less the deterioration of the light selective absorption function is exhibited, and the better the weather resistance is exhibited.

The absorbance retention ratio of the sample (6) was also determined by placing the sample in a sunshine weatherometer (manufactured by Suga Test Instruments) at a temperature of 63 ℃ and a relative humidity of 50% RH for 225 hours.

Absorbance retention (%) (a (405) after the durability test/a (405) before the durability test) x 100

The absorbance retention was measured in the same manner as in the case where the pressure-sensitive adhesive sheet (19) was replaced with each of the pressure-sensitive adhesive sheets (20) to (25). The results are shown in Table 9.

[ Table 9]

TABLE 9

(example 93)

< preparation of resin composition for spectacle lens >

40 parts of xylylene diisocyanate, 60 parts of trimethylolpropane tris (thioglycolate) (Japanese: トリメチロールプロパントリス (チオグリコラート)), 1.6 parts of a compound represented by the formula (UVA-6), 0.2 part of a mold release agent (trade name: ZELEC-UN, available from Sigma-Aldrich Co., Ltd.), and 0.03 part of dibutyltin dichloride were mixed and stirred. The resulting mixture was allowed to stand in a vacuum drier for 1 hour, and was degassed. The resulting mixture was poured into a glass mold and heated at 120 ℃ for 1 hour. Only the resin plate was peeled off to prepare a resin plate having a thickness of 2mm and 3 cm. times.3 cm.

< measurement of Absorbance Retention Rate of resin plate >

The absorbance of the resin plate obtained above at a wavelength of 300 to 800nm was measured in units of 1nm step using a spectrophotometer (UV-2450: Shimadzu corporation).

The resin plate after the measurement was put into a sunshine weatherometer (manufactured by Suga Test Instruments) at a temperature of 63 ℃ and a relative humidity of 50% RH for 75 hours to perform a weather resistance Test. The absorbance of the removed resin plate was measured by the same method as described above. From the measured absorbance, the absorbance retention of the sample at a wavelength of 420nm was determined based on the following formula. The results are shown in Table 10. The closer the absorbance retention rate is to 100, the less the deterioration of the light selective absorption function is exhibited, and the better the weather resistance is exhibited.

In order to efficiently intercept blue light, which is likely to adversely affect health, as a spectacle lens, it is required that the absorbance retention ratio at a wavelength of 420nm is good. In addition, the larger the value of a (420)/a (480), the more the blue light can be blocked with less coloring.

Absorbance retention (%) (a (420) after durability test/a (420) before durability test) x 100

[ Table 10]

Watch 10

	Compound (I)	A(420)	A(480)	A(420)/A(480)	Absorbance retention ratio
						Example 93	Formula (UVA-6)	3.26	0.049	66.5	100

The novel compound having a merocyanine skeleton has high absorption selectivity for visible light having a short wavelength of 380-400 nm. In addition, the compound of the present invention has high absorbance retention rate after weather resistance test and good weather resistance.

136页详细技术资料下载

上一篇：一种医用注射器针头装配设备

下一篇：含有甲硅烷基醚的磺酸盐

Compound (I)

相关技术

网友询问留言