Compound and organic light emitting device including the same

文档序号：1966665 发布日期：2021-12-14 浏览：15次中文

阅读说明：本技术 化合物和包含其的有机发光器件 (Compound and organic light emitting device including the same ) 是由金宣佑洪玩杓琴水井金明坤金京嬉于 2020-09-18 设计创作，主要内容包括：本说明书提供了化学式1的化合物和包含其的有机发光器件。(The present specification provides a compound of chemical formula 1 and an organic light emitting device including the same.)

1. A compound represented by the following chemical formula 1:

[ chemical formula 1]

In the chemical formula 1, the first and second,

x1 is O or

A1 is an aromatic hydrocarbon ring, or a heterocyclic ring, at least one of A2 and A3 is a heterocyclic ring containing S or O, and the remainder is an aromatic hydrocarbon ring, or a ring represented by chemical formula 1,

when A2 and A3 are heterocyclic rings containing S or O, A2 and A3 are the same as or different from each other,

a4 and a5 are the same as or different from each other and each is independently an alkyl group; a cycloalkyl group; an aryl group; or a heterocyclic group,

two or more adjacent of A1-A5 are optionally bonded to each other to form a substituted or unsubstituted ring,

r1 is substituted or unsubstituted alkyl; substituted or unsubstituted heterocyclyl; or a group represented by the following chemical formula 2, or bonded to an adjacent group to form a substituted or unsubstituted ring,

r2 to R5 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; substituted or unsubstituted alkyl; substituted or unsubstituted aryloxy; substituted or unsubstituted alkoxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; substituted or unsubstituted haloalkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or unsubstituted arylalkyl; a substituted or unsubstituted boron group; substituted or unsubstituted aryl; substituted or unsubstituted heterocyclyl; or a group represented by the following chemical formula 2, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

r1 to r5 are each an integer of 1 to 15,

when each of r1 to r5 is 2 or more, two or more substituents in parentheses are the same as or different from each other,

[ chemical formula 2]

In the chemical formula 2, the first and second organic solvents,

b1 and B2 are the same as or different from each other and each independently is an alkyl group; a cycloalkyl group; an aryl group; or a heterocyclic group,

r6 and R7 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted haloalkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or unsubstituted arylalkyl; a substituted or unsubstituted boron group; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

r6 and r7 are each an integer of 1 to 10,

when r6 and r7 are each 2 or more, two or more substituents in parentheses are the same as or different from each other, and

at least one hydrogen at the substitutable position of chemical formula 1 is replaced with deuterium.

2. The compound according to claim 1, wherein chemical formula 1 is represented by the following chemical formula 1-1 or 1-2:

[ chemical formula 1-1]

[ chemical formulas 1-2]

In chemical formulas 1-1 and 1-2,

definitions of a1 to a5, R1 to R5, and R1 to R5 are the same as those defined in chemical formula 1.

3. The compound according to claim 1, wherein chemical formula 1 is represented by any one of the following chemical formulae 1-3 to 1-10:

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

[ chemical formulas 1 to 5]

[ chemical formulas 1 to 6]

[ chemical formulas 1 to 7]

[ chemical formulas 1 to 8]

[ chemical formulas 1 to 9]

[ chemical formulas 1-10]

In chemical formulas 1-3 to 1-10,

the definitions of X1, a1, a4, R1 to R4 and R1 to R4 are the same as those defined in chemical formula 1,

r12, R13, R22, R23, R32, R33, R42 and R43 are the same as each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted haloalkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or unsubstituted arylalkyl; a substituted or unsubstituted boron group; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group; or a group represented by chemical formula 2, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

r12 and r13 are each 1 or 2,

r22, r23, r32 and r33 are each integers of 1 to 4,

r42 and r43 are each an integer of 1 to 6,

when r12 and r13 are each 2, the two structures in parentheses are the same as or different from each other,

when r22, r23, r32, r33, r42 and r43 are each 2 or more, two or more structures in parentheses are the same as or different from each other,

x and X' are identical to or different from each other and are each independently O or S, and

a '2 and a' 3 are the same as or different from each other, and each independently is an aromatic hydrocarbon ring; or a ring represented by chemical formula 1.

4. The compound according to claim 1, wherein chemical formula 1 is represented by any one of the following chemical formulae 1-11 to 1-26:

[ chemical formulas 1 to 11]

[ chemical formulas 1 to 12]

[ chemical formulas 1 to 13]

[ chemical formulas 1 to 14]

[ chemical formulas 1 to 15]

[ chemical formulas 1 to 16]

[ chemical formulas 1 to 17]

[ chemical formulas 1 to 18]

[ chemical formulas 1 to 19]

[ chemical formulas 1 to 20]

[ chemical formulas 1 to 21]

[ chemical formulas 1 to 22]

[ chemical formulas 1 to 23]

[ chemical formulas 1 to 24]

[ chemical formulas 1 to 25]

[ chemical formulas 1 to 26]

In chemical formulas 1-11 to 1-26,

the definitions of X1, A1, A4, R1, R4, R1 and R4 are the same as those defined in chemical formula 1,

r12 and r13 are each 1 or 2,

r22, r23, r32 and r33 are each integers of 1 to 4,

r42 and r43 are each an integer of 1 to 6,

when r12 and r13 are each 2, the two structures in parentheses are the same as or different from each other,

when r22, r23, r32, r33, r42 and r43 are each 2 or more, two or more structures in parentheses are the same as or different from each other, and

x and X' are the same or different from each other and are each independently O or S.

5. The compound of claim 1, wherein a1 is a phenyl ring; or a ring represented by chemical formula 1.

6. The compound of claim 1, wherein adjacent two or more of a 1-a 5 are bonded to each other to form a ring represented by chemical formula 1.

7. The compound of claim 1, wherein R1 is a linear or branched alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; a straight-chain or branched haloalkyl group having 1 to 30 carbon atoms; monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; a substituted or unsubstituted polycyclic heterocyclic group containing N having 2 to 30 carbon atoms; or a group represented by chemical formula 2.

8. The compound of claim 1, wherein R2 to R7 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a linear or branched alkyl group having 1 to 30 carbon atoms; monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; monocyclic or polycyclic arylsilyl groups having 6 to 30 carbon atoms; monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; a linear or branched arylalkyl group having from 6 to 30 carbon atoms; a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and the substituent is substituted with one or more selected from the group consisting of: deuterium, a halogen group, an unsubstituted or deuterium-substituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, and a straight-chain or branched haloalkyl group having 1 to 30 carbon atoms.

9. The compound of claim 1, wherein any one or more of two adjacent R2, two adjacent R3, two adjacent R4, two adjacent R5, two adjacent R6, and two adjacent R7 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

10. The compound of claim 1, wherein at least one of R1-R7 is a substituted or unsubstituted polycyclic heterocycle having 2-30 carbon atoms that includes N.

11. The compound of claim 1, wherein chemical formula 1 is any one selected from the group consisting of:

12. the compound of claim 1, wherein R1 comprises deuterium.

13. The compound of claim 1, wherein R2 comprises deuterium.

14. The compound of claim 1, wherein the degree of deuteration of chemical formula 1 is 5% or more and 75% or less.

15. The compound of claim 1, wherein chemical formula 1 comprises: a linear or branched alkyl group having 1 to 10 carbon atoms substituted with deuterium; a monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms substituted with one or more of deuterium and a linear or branched alkyl group having 1 to 10 carbon atoms substituted with deuterium; or monocyclic or polycyclic aliphatic hydrocarbon fused rings having 3 to 10 carbon atoms substituted with one or more of deuterium and a linear or branched alkyl group having 1 to 10 carbon atoms substituted with deuterium.

16. An organic light emitting device comprising:

a first electrode;

a second electrode; and

an organic material layer having one or more layers disposed between the first electrode and the second electrode,

wherein one or more of the layers of organic material comprise a compound according to any one of claims 1 to 15.

17. The organic light-emitting device according to claim 16, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer contains the compound.

18. The organic light emitting device of claim 16, wherein the organic material layer comprises a light emitting layer comprising a dopant material, and the dopant material comprises the compound.

19. The organic light-emitting device according to claim 16, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer further comprises a compound represented by the following chemical formula H:

[ chemical formula H ]

In the chemical formula H, the compound represented by the formula,

l20 and L21 are the same or different from each other and are each independently a direct bond; substituted or unsubstituted arylene; or a substituted or unsubstituted heteroarylene group,

ar20 and Ar21 are the same or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, and

R20 is hydrogen; deuterium; a halogen group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group.

20. The organic light-emitting device of claim 19, wherein Ar20 is a substituted or unsubstituted heterocyclic group and Ar21 is a substituted or unsubstituted aryl group.

21. The organic light-emitting device according to claim 16, wherein the organic material layer comprises a light-emitting layer further containing a host compound, and at least one hydrogen at a substitutable position of the host compound is substituted with deuterium.

22. The organic light emitting device of claim 16, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises a host and two or more mixed dopants.

23. An organic light-emitting device according to claim 16 wherein the organic material layer comprises a light-emitting layer and the light-emitting layer comprises a dopant and one or more hosts.

24. The organic light-emitting device according to claim 16, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer contains a dopant and two or more mixed hosts.

Technical Field

This application claims priority and benefit to korean patent application No. 10-2019-.

The present specification relates to compounds and organic light emitting devices comprising the same.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer interposed therebetween. Here, in many cases, the organic material layer may have a multi-layered structure composed of different materials to improve efficiency and stability of the organic light emitting device, and the organic material layer may be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, if a voltage is applied between two electrodes, holes are injected from a positive electrode into an organic material layer, electrons are injected from a negative electrode into the organic material layer, excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall to the ground state again.

There is a continuing need to develop new materials for the aforementioned organic light emitting devices.

Disclosure of Invention

Technical problem

The present specification provides compounds and organic light emitting devices comprising the same.

Technical scheme

An exemplary embodiment of the present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the chemical formula 1, the first and second,

x1 is O or

A1 is an aromatic hydrocarbon ring, or a heterocyclic ring,

at least one of A2 and A3 is a heterocyclic ring including S or O, and the remaining is an aromatic hydrocarbon ring, or a ring represented by chemical formula 1,

when A2 and A3 are heterocyclic rings containing S or O, A2 and A3 are the same as or different from each other,

a4 and a5 are the same as or different from each other and each is independently an alkyl group; a cycloalkyl group; an aryl group; or a heterocyclic group,

two or more adjacent of a 1-a 5 may be bonded to each other to form a substituted or unsubstituted ring,

r1 to r5 are each an integer of 1 to 15,

when each of r1 to r5 is 2 or more, two or more substituents in parentheses are the same as or different from each other,

[ chemical formula 2]

In the chemical formula 2, the first and second organic solvents,

b1 and B2 are the same as or different from each other and each independently is an alkyl group; a cycloalkyl group; an aryl group; or a heterocyclic group,

r6 and r7 are each an integer of 1 to 10,

when r6 and r7 are each 2 or more, two or more substituents in parentheses are the same as or different from each other, and

at least one hydrogen at the substitutable position of chemical formula 1 is replaced with deuterium.

Further, the present specification provides an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer include the compound.

Advantageous effects

The compound described in this specification can be used as a material for an organic material layer of an organic light-emitting device. The compound according to another exemplary embodiment may improve efficiency, achieve a low driving voltage, and/or improve lifetime characteristics in an organic light emitting device. In particular, the compounds described in the present specification can be used as materials for hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection. In addition, the organic light emitting device according to one exemplary embodiment of the present specification has low driving voltage, high efficiency, or long lifespan effects.

Drawings

Fig. 1 to 3 illustrate an example of an organic light emitting device according to an exemplary embodiment of the present specification.

[ description of reference numerals ]

1: substrate

2: a first electrode

3: luminescent layer

4: second electrode

5: hole injection layer

6: hole blocking layer

7: electron injection and transport layer

8: hole transport layer

9: electron blocking layer

10: a first electron transport layer

11: a second electron transport layer

12: electron injection layer

Detailed Description

Hereinafter, the present specification will be described in more detail.

The boron compound in the related art has a full width at half maximum of about 23nm to 30nm and a wavelength of its basic core structure of about 453nm, but the boron compound in the related art has a limitation in that the lifespan is deteriorated because the stability of the material is relatively lowered compared to the amine compound. Therefore, a method of improving the stability of a material while maintaining excellent optical characteristics by adjusting the substituent of the boron compound to ensure a long service life is required.

The present specification provides a compound in which at least one hydrogen at a substitutable position is replaced with deuterium, and an organic light-emitting device including the same. Since the C-D bond of the compound of the present invention is stronger than the C-H bond, the stability of the compound can be improved. When the chemical decomposition of the light-emitting compound is accompanied by the destruction of a relatively weak C (sp3) -H bond, there is an effect that the stability of the compound can be further improved by using a C-D bond stronger than the C-H bond.

In this case, when an alkyl group is used as a substituent capable of supplying electrons, the light emitting characteristics can be effectively adjusted, but the C — H bond of the alkyl group introduced in a high energy state is broken, causing decomposition of the compound, so that the overall life characteristics of the device become problematic. Therefore, when the deuterium substituted alkyl group is used, the light emission characteristics can be effectively adjusted while ensuring the stability of the blue device. Further, when deuterium with a smaller van der waals radius is used, steric hindrance is smaller than that of the existing alkyl group, so that conjugation can be improved.

In addition, due to the carbon-deuterium bond of the heterocycle including O or S in the central core of chemical formula 1 of the present specification, the long lifespan of the organic light emitting device including the same may be shown to be maximized. Further, the boron compound of chemical formula 1 having a heterocycle including O or S exhibits a characteristic of having lower excited triplet energy than the boron compound in the related art. Unlike a singlet state that rapidly returns to a ground state through a luminescence process, the triplet state slowly returns to the ground state while dissipating energy by thermal or vibrational energy, so that a problem occurs in that the boron compound in the related art deteriorates through intermolecular interaction with a molecule having high triplet energy. Therefore, in the boron compound in the related art, in a process in which the compound is decomposed by light or current, a carbon-hydrogen bond, which is a weak bond in a molecule, is dissociated to form a radical and an ion, but the compound of chemical formula 1 may effectively prevent the decomposition of the compound by changing the carbon-hydrogen bond to a stronger carbon-deuterium bond.

Examples of the substituent in the present specification will be described below, but are not limited thereto.

In the context of the present specification,meaning the linking moiety.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound becomes an additional substituent, and the position of substitution is not limited as long as the position is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more substitutions are made, the two or more substituents may be the same as or different from each other.

In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from: deuterium; a halogen group; a cyano group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkenyl group; a haloalkoxy group; an arylalkyl group; a haloalkyl group; a silyl group; a boron group; an amine group; an aryl group; and a heterocyclic group, substituted with a substituent connected to two or more substituents among the exemplified substituents, or having no substituent.

In the present specification, the fact that two or more substituents are linked means that the hydrogen of any substituent is linked to another substituent. For example, when two substituents are linked to each other, phenyl and naphthyl groups may be linked to each other to be A substituent of (1). Further, the case where three substituents are linked to each other includes not only the case where (substituent 1) - (substituent 2) - (substituent 3) are continuously linked to each other but also the case where (substituent 2) and (substituent 3) are linked to (substituent 1). For example, phenyl, naphthyl and isopropyl groups may be linked to each other to beA substituent of (1). The above definition also applies equally to the case where four or more substituents are linked to each other.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo [2.2.1] octyl, norbornyl and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentoxy group, neopentoxy group, isopentoxy group, n-hexoxy group, 3-dimethylbutoxy group, 2-ethylbutoxy group, n-octoxy group, n-nonoxy group, n-decoxy group, benzyloxy group, p-methylbenzyloxy group and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, Phenyl, styryl, and the like, but are not limited thereto.

In the present specification, haloalkyl means an alkyl group, in the definition of alkyl, substituted with at least one halogen group in place of hydrogen.

In the present specification, haloalkoxy means that in the definition of alkoxy, at least one halogen group is substituted in the alkoxy in place of hydrogen.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 30. Specific examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aromatic group include naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, phenalkenyl, perylenyl, perylene, and the like,A phenyl group, a fluorenyl group, and the like, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

Examples of the case where the fluorenyl group is substituted include And the like, but are not limited thereto.

In the present specification, an "adjacent" group may mean a substituent substituted for an atom directly connected to an atom substituted with the corresponding substituent, a substituent located sterically closest to the corresponding substituent, or another substituent substituted for an atom substituted with the corresponding substituent. For example, two substituents in the phenyl ring that are ortho-substituted and two substituents in the aliphatic ring that substitute the same carbon can be interpreted as groups that are "adjacent" to each other.

In the present specification, arylalkyl means an alkyl group substituted with an aryl group, and the above examples of aryl and alkyl groups can be applied to aryl and alkyl groups of the arylalkyl group.

In the present specification, aryloxy means that in the definition of alkoxy, alkoxy is substituted with aryl instead of alkyl, and examples of aryloxy include phenoxy, p-tolyloxy, m-tolyloxy, 3, 5-dimethyl-phenoxy, 2,4, 6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, 9-phenanthrenyloxy, and the like, but are not limited thereto.

In the present specification, the alkyl group in the alkylthio group is the same as the above example of the alkyl group. Specific examples of the alkylthio group include methylthio, ethylthio, tert-butylthio, hexylthio, octylthio and the like, but are not limited thereto.

In the present specification, the aryl group in the arylthio group is the same as the above-mentioned example of the aryl group. Specific examples of the arylthio group include, but are not limited to, phenylthio group, 2-methylphenylthio group, 4-tert-butylphenylthio group and the like.

In the present specification, the heterocyclic group contains one or more atoms other than carbon, i.e., one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, and the like. The number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30, and the heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl group,Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinylPhthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoAzolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthridinyl, phenanthrolinyl, isooxazolylAzolyl, thiadiazolyl, dibenzofuranyl, dibenzothiapyrrolyl, thiophenylThienyl, thiophenOxazinyl, phenothiazinyl, dihydroindenocarbazolyl, spirofluoreneXanthenyl, spirofluoreneXanthenyl group, spirofluorenylthioxanthyl group, and the like, but are not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like. The above examples of alkyl groups can be applied to alkyl groups in alkylsilyl groups, the above examples of aryl groups can be applied to aryl groups in arylsilyl groups, and examples of heterocyclic groups can be applied to heteroaryl groups in heteroarylsilyl groups.

In the present specification, the boron group may be-BR₁₀₀R₁₀₁And R is₁₀₀And R₁₀₁Are identical or different from each other and can each be independently selected from hydrogen; deuterium; halogen; a nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted, linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted with 6 to 30A monocyclic or polycyclic aromatic group of carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. Specific examples of the boron group include a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but are not limited thereto.

In the present specification, the amine group may be selected from-NH₂Alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino groups, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methyl-anthrylamino group, a diphenylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrylfluorenylamino group, an N-biphenylfluorenylamino group, and the like.

In the present specification, an N-alkylarylamino group means an amino group in which N of the amino group is substituted with an alkyl group and an aryl group. The alkyl and aryl groups in the N-alkylarylamino group are the same as the above examples for alkyl and aryl groups.

In the present specification, N-arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group. The aryl and heteroaryl groups in the N-arylheteroarylamino group are the same as the above examples of aryl and heterocyclic groups.

In the present specification, N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group. The alkyl and heteroaryl groups in the N-alkylheteroarylamino groups are the same as the above examples of alkyl and heterocyclic groups.

In the present specification, examples of the alkylamino group include a substituted or unsubstituted monoalkylamino group or a substituted or unsubstituted dialkylamino group. The alkyl group in the alkylamino group may be a straight-chain or branched alkyl group. The alkylamino group comprising two or more alkyl groups can comprise a straight chain alkyl group, a branched alkyl group, or both a straight chain alkyl group and a branched alkyl group. For example, the alkyl group in the alkylamino group may be selected from the above-mentioned examples of alkyl groups.

In the present specification, examples of heteroarylamino groups include substituted or unsubstituted monoheteroarylamino groups or substituted or unsubstituted diheteroarylamino groups. Heteroarylamine groups comprising two or more heteroaryls may comprise a monocyclic heteroaryl, a polycyclic heteroaryl, or both a monocyclic heteroaryl and a polycyclic heteroaryl. For example, the heteroaryl group in the heteroarylamine group may be selected from the above-mentioned examples of heterocyclic groups.

In the present specification, "adjacent two of the substituents are bonded to each other to form a ring" means that the substituents are bonded to adjacent groups to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups, "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from examples of cycloalkyl groups or aryl groups, except that the hydrocarbon ring is not monovalent.

In the present specification, the heterocyclic ring contains one or more atoms other than carbon, i.e., one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic ring and an aliphatic ring, and the aromatic heterocyclic ring may be selected from examples of heterocyclic groups except that the aromatic heterocyclic ring is not monovalent.

In the present specification, aliphatic heterocyclic ring means an aliphatic ring containing one or more hetero atoms. Examples of aliphatic heterocycles include ethylene oxide, tetrahydrofuran, 1, 4-bis Alkanes, pyrrolidines, piperidines, morpholines, oxaringsHeptane, azocane, thiacyclooctane, and the like, but are not limited thereto.

In the present specification, the heterocyclic ring includes a ring represented by chemical formula 1.

In the present specification, arylene means a group having two bonding positions in an aryl group, i.e., a divalent group. The above description for aryl groups applies to arylene groups, except that arylene groups are each divalent groups.

In the present specification, heteroarylene means a group having two bonding positions in heteroaryl, i.e., a divalent group. The above description for heterocyclyl groups can be applied to heteroarylenes, except that the heteroarylenes are each divalent groups.

In this specification, "deuterated," "substituted with deuterium" or "containing deuterium" means that at least one substitutable H (hydrogen) is substituted with D (deuterium). "x% deuterated," "substituted with x% deuterium," or "comprising x% deuterium" means that deuterium is present at least 100 times the natural abundance level of hydrogen at the substitutable position of chemical formula 1. Specifically, deuterium is present at the substitutable position of chemical formula 1 at least 50 times the natural abundance level of hydrogen.

In the present specification, the degree of deuteration can be determined by a known method such as nuclear magnetic resonance spectroscopy ( ¹HNMR) or GC/MS.

According to an exemplary embodiment of the present specification, the deuteration degree of chemical formula 1 is 10% to 100%.

According to an exemplary embodiment of the present specification, the degree of deuteration of chemical formula 1 is 10% or more and less than 100%.

According to an exemplary embodiment of the present specification, the degree of deuteration of chemical formula 1 is 75% or less.

According to an exemplary embodiment of the present specification, the deuteration degree of chemical formula 1 is 5% or more and 75% or less. When the deuteration degree of chemical formula 1 is in the above range, it is possible to economically configure a device having a long lifetime by replacing the C-H bond at the position where dissociation easily occurs in the excited state with a relatively stronger C-D bond, compared to by using a compound having a deuteration degree of 100%.

Hereinafter, the heterocyclic compound represented by chemical formula 1 will be described in detail.

According to an exemplary embodiment of the present specification, in chemical formula 1, X1 is O.

According to an exemplary embodiment of the present specification, in chemical formula 1, X1 is

According to an exemplary embodiment of the present specification, chemical formula 1 is represented by the following chemical formula 1-1 or 1-2.

[ chemical formula 1-1]

[ chemical formulas 1-2]

In chemical formulas 1-1 and 1-2,

definitions of a1 to a5, R1 to R5, and R1 to R5 are the same as those defined in chemical formula 1.

According to an exemplary embodiment of the present specification, chemical formula 1 is represented by any one of the following chemical formulae 1-3 to 1-10.

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

[ chemical formulas 1 to 5]

[ chemical formulas 1 to 6]

[ chemical formulas 1 to 7]

[ chemical formulas 1 to 8]

[ chemical formulas 1 to 9]

[ chemical formulas 1-10]

In chemical formulas 1-3 to 1-10,

the definitions of X1, a1, a4, R1 to R4 and R1 to R4 are the same as those defined in chemical formula 1,

r12 and r13 are each 1 or 2,

r22, r23, r32 and r33 are each integers of 1 to 4,

r42 and r43 are each an integer of 1 to 6,

when r12 and r13 are each 2, the two structures in parentheses are the same as or different from each other,

when r22, r23, r32, r33, r42 and r43 are each 2 or more, two or more structures in parentheses are the same as or different from each other,

x and X' are identical to or different from each other and are each independently O or S, and

a '2 and a' 3 are the same as or different from each other, and each independently is an aromatic hydrocarbon ring; or a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, chemical formula 1 is represented by any one of the following chemical formulae 1-11 to 1-26.

[ chemical formulas 1 to 11]

[ chemical formulas 1 to 12]

[ chemical formulas 1 to 13]

[ chemical formulas 1 to 14]

[ chemical formulas 1 to 15]

[ chemical formulas 1 to 16]

[ chemical formulas 1 to 17]

[ chemical formulas 1 to 18]

[ chemical formulas 1 to 19]

[ chemical formulas 1 to 20]

[ chemical formulas 1 to 21]

[ chemical formulas 1 to 22]

[ chemical formulas 1 to 23]

[ chemical formulas 1 to 24]

[ chemical formulas 1 to 25]

[ chemical formulas 1 to 26]

In chemical formulas 1-11 to 1-26,

the definitions of X1, A1, A4, R1, R4, R1 and R4 are the same as those defined in chemical formula 1,

r12 and r13 are each 1 or 2,

r22, r23, r32 and r33 are each integers of 1 to 4,

r42 and r43 are each an integer of 1 to 6,

when r12 and r13 are each 2, the two structures in parentheses are the same as or different from each other,

when r22, r23, r32, r33, r42 and r43 are each 2 or more, two or more structures in parentheses are the same as or different from each other, and

x and X' are the same or different from each other and are each independently O or S.

According to another exemplary embodiment of the present description, X is O.

According to yet another exemplary embodiment of the present description, X' is O.

According to yet another exemplary embodiment of the present description, X is S.

According to another exemplary embodiment of the present description, X' is S.

According to yet another exemplary embodiment of the present description, X is O, and X' is O.

According to yet another exemplary embodiment of the present description, X is O and X' is S.

According to another exemplary embodiment of the present description, X is S, and X' is O.

According to yet another exemplary embodiment of the present description, X is S, and X' is S.

According to an exemplary embodiment of the present specification, in chemical formula 1, a1 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in chemical formula 1, a1 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; or a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in chemical formula 1, a1 is a benzene ring; or a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, in chemical formula 1, at least one of a2 and A3 is a monocyclic or polycyclic heterocyclic ring containing S or O and having 2 to 30 carbon atoms, and the remainder is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, in chemical formula 1, at least one of a2 and A3 is a monocyclic or polycyclic heterocyclic ring containing S or O and having 2 to 20 carbon atoms, and the remainder is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; or a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, in chemical formula 1, at least one of a2 and A3 is a monocyclic or bicyclic heterocyclic ring containing S or O and having 2 to 10 carbon atoms, and the remainder is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 12 carbon atoms; or a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, in chemical formula 1, at least one of a2 and A3 is a furan ring; a benzofuran ring; a dibenzofuran ring; a thiophene ring; a benzothiophene ring; or a dibenzothiophene ring, and the remainder a benzene ring; a fluorene ring; or a ring represented by chemical formula 1.

According to one exemplary embodiment of the present description, a4 and a5 are the same or different from each other and each independently is a linear or branched alkyl group having 1 to 30 carbon atoms; monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

According to one exemplary embodiment of the present description, a4 and a5 are the same or different from each other and each independently is a linear or branched alkyl group having 1 to 20 carbon atoms; monocyclic or polycyclic cycloalkyl groups having 3 to 20 carbon atoms; monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present description, a4 and a5 are the same or different from each other and each is independently a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a fluorenyl group; a triphenylene group; a tertiary butyl group; an adamantyl group; a benzofuranyl group; or dibenzothienyl.

According to an exemplary embodiment of the present description, two or more adjacent of a1 to a5 are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

According to an exemplary embodiment of the present specification, two or more adjacent of a1 to a5 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, two or more adjacent ones of a1 to a5 are bonded to each other to form a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, two or more adjacent ones of a1 to a5 are bonded to each other to form any one ring in the structure represented by the following group a.

< group A >

In the above-described structure, the first and second electrodes are formed on the substrate,

g10 to G14 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted haloalkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or unsubstituted arylalkyl; a substituted or unsubstituted boron group; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring,

g10 is an integer from 1 to 10,

g11 is an integer from 1 to 8,

g12 is an integer from 1 to 6,

when each of g10 to g12 is 2 or more, two or more structures in parentheses are the same as or different from each other,

g1 is 0 or 1 and,

when g1 is 0, the structures in parentheses are directly bonded to each other without a carbon atom,

g2 is 0 or 1, and

when g2 is 0, the structures in parentheses are directly bonded to each other without a carbon atom.

< group B >

In the above-described structure, the first and second electrodes are formed on the substrate,

g100 to G120 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted haloalkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or unsubstituted arylalkyl; a substituted or unsubstituted boron group; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic ring,

g100, g101, g108, g109 and g116 to g118 are each an integer of 1 to 8,

g102 and g107 are each an integer of 1 to 12,

g103 and g104 are each an integer of 1 to 10,

g105 and g110 to g113 are each an integer of 1 to 4,

g114 is an integer of 1 to 14,

g115 is an integer of 1 to 18, and

when each of g100 to g118 is 2 or more, two or more structures in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present description, G100 to G120 are the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted silyl; or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present description, G100 to G120 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted, linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted, linear or branched alkylsilyl group of 1 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G120 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted, linear or branched alkylsilyl group of 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G120 are the same as or different from each other, and each is independently hydrogen; deuterium; unsubstituted or deuterium-substituted straight-chain or branched alkyl having 1 to 30 carbon atoms; unsubstituted or deuterium-substituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms; unsubstituted or deuterium-substituted linear or branched alkylsilyl group having 1 to 30 carbon atoms; or unsubstituted or deuterium-substituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G120 are the same as or different from each other, and each is independently hydrogen; deuterium; unsubstituted or deuterium-substituted straight-chain or branched alkyl having 1 to 20 carbon atoms; unsubstituted or deuterium-substituted monocyclic or polycyclic cycloalkyl having 3 to 20 carbon atoms; unsubstituted or deuterium-substituted linear or branched alkylsilyl group having 1 to 20 carbon atoms; or unsubstituted or deuterium-substituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G120 are the same as or different from each other, and each is independently hydrogen; deuterium; a methyl group; -CD ₃(ii) a A tertiary butyl group; a cyclohexyl group; a trimethylsilyl group; or unsubstituted or substitutedDeuterium substituted phenyl.

According to one exemplary embodiment of the present description, a1 and a4 are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

According to an exemplary embodiment of the present description, a1 and a4 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, a1 and a4 are bonded to each other to form a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, a1 and a4 are bonded to each other to form any one of rings in the structures represented by group a and group B.

According to one exemplary embodiment of the present description, a1 and a5 are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

According to an exemplary embodiment of the present description, a1 and a5 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, a1 and a5 are bonded to each other to form a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, a1 and a5 are bonded to each other to form any one of rings in the structures represented by group a and group B.

According to one exemplary embodiment of the present description, a2 and a4 are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

According to an exemplary embodiment of the present description, a2 and a4 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, a2 and a4 are bonded to each other to form a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, a2 and a4 are bonded to each other to form any one of rings in the structures represented by group a and group B.

According to one exemplary embodiment of the present description, A3 and a5 are bonded to each other to form a substituted or unsubstituted heterocyclic ring.

According to an exemplary embodiment of the present description, A3 and a5 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A3 and a5 are bonded to each other to form a ring represented by chemical formula 1.

According to an exemplary embodiment of the present specification, A3 and a5 are bonded to each other to form any one of rings in the structures represented by group a and group B.

According to an exemplary embodiment of the present description, any one or more of adjacent two R2, adjacent two R3, adjacent two R4, adjacent two R5, adjacent two R6, and adjacent two R7 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present description, any one or more of adjacent two R2, adjacent two R3, adjacent two R4, adjacent two R5, adjacent two R6, and adjacent two R7 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring, aromatic hydrocarbon ring, or aliphatic and aromatic fused hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted, mono-or polycyclic aliphatic heterocycle having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, any one or more of adjacent two R2, adjacent two R3, adjacent two R4, adjacent two R5, adjacent two R6, and adjacent two R7 are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring, aromatic hydrocarbon ring, or aliphatic and aromatic condensed hydrocarbon ring having 3 to 30 carbon atoms which is unsubstituted or substituted with deuterium or unsubstituted or substituted with deuterium with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic aliphatic heterocyclic ring having 2 to 30 carbon atoms which is unsubstituted or substituted by deuterium or a linear or branched alkyl group having 1 to 30 carbon atoms which is unsubstituted or substituted by deuterium.

According to an exemplary embodiment of the present description, any one or more of adjacent two R2, adjacent two R3, adjacent two R4, adjacent two R5, adjacent two R6, and adjacent two R7 are bonded to each other to form a cyclopentane ring; a cyclohexane ring; a cycloheptane ring; bicyclo [2.2.1] octane rings; a norbornane ring; an adamantane ring; an indene ring; phenanthrene rings; a tetrahydrofuran ring; a tetrahydrothiophene ring; a pyrrolidine ring; an octahydrobenzofuran ring; an octahydrobenzothiophene ring; or an octahydroindene ring, and the ring is unsubstituted or substituted with deuterium, methyl substituted with deuterium, or unsubstituted methyl.

According to one exemplary embodiment of the present description, R1 is a substituted or unsubstituted alkyl; substituted or unsubstituted haloalkyl; substituted or unsubstituted cycloalkyl; or a substituted or unsubstituted polycyclic heterocyclic group containing N; or a group represented by chemical formula 2.

According to one exemplary embodiment of the present description, R1 is a substituted or unsubstituted, straight or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted, linear or branched haloalkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted polycyclic heterocyclic group containing N having 2 to 30 carbon atoms; or a group represented by chemical formula 2.

According to one exemplary embodiment of the present description, R1 is a substituted or unsubstituted, straight or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted, linear or branched haloalkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted polycyclic heterocyclic group containing N having 2 to 30 carbon atoms; or a group represented by chemical formula 2.

According to one exemplary embodiment of the present description, R1 is a linear or branched alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium; a straight-chain or branched haloalkyl group having 1 to 30 carbon atoms; monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; a substituted or unsubstituted polycyclic heterocyclic group containing N having 2 to 30 carbon atoms; or a group represented by chemical formula 2.

According to one exemplary embodiment of the present description, R1 is a linear or branched alkyl group having 1 to 20 carbon atoms that is unsubstituted or substituted with deuterium; a straight-chain or branched haloalkyl group having 1 to 20 carbon atoms; monocyclic or polycyclic cycloalkyl groups having 3 to 20 carbon atoms; a substituted or unsubstituted polycyclic heterocyclic group containing N having 2 to 30 carbon atoms; or a group represented by chemical formula 2.

According to an exemplary embodiment of the present description, R1 is methyl; -CD₃；-OCF₃(ii) a A tertiary butyl group; a cyclohexyl group; an adamantyl group; a substituted or unsubstituted polycyclic heterocyclic group containing N having 2 to 30 carbon atoms; or a group represented by chemical formula 2.

According to an exemplary embodiment of the present description, R1 is methyl; a tertiary butyl group; a cyclohexyl group; an adamantyl group; a polycyclic heterocyclic group having 2 to 30 carbon atoms containing N; or a group represented by chemical formula 2, and a tert-butyl group; a cyclohexyl group; an adamantyl group; a polycyclic heterocyclic group having 2 to 30 carbon atoms containing N; or the group represented by chemical formula 2 is substituted with deuterium.

According to an exemplary embodiment of the present description, R1 comprises deuterium.

According to an exemplary embodiment of the present specification, the polycyclic heterocyclic group having 2 to 30 carbon atoms containing N is a group represented by any one of the structures of the following group C.

< group C >

In the above-described structure, the first and second electrodes are formed on the substrate,

g10 and G11 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted haloalkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or unsubstituted arylalkyl; a substituted or unsubstituted boron group; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring,

g10 is an integer from 1 to 10,

g11 is an integer from 1 to 8,

when each of g10 and g11 is 2 or more, two or more structures in parentheses are the same as or different from each other,

g1 is 0 or 1 and,

when g1 is 0, the structures in parentheses are directly bonded to each other without a carbon atom,

g2 is 0 or 1 and,

when g2 is 0, the structures in parentheses are directly bonded to each other without a carbon atom, and

is a moiety bonded to chemical formula 1.

< group D >

In the above-described structure, the first and second electrodes are formed on the substrate,

g100 to G115 are the same or different from each other and each independently hydrogen; deuterium; a halogen group; a cyano group; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted haloalkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted silyl; substituted or unsubstituted arylalkyl; a substituted or unsubstituted boron group; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic ring,

g100, g101, g108 and g109 are each an integer of 1 to 8,

g102 and g107 are each an integer of 1 to 12,

g103 and g104 are each an integer of 1 to 10,

g105 and g110 to g113 are each an integer of 1 to 4,

g114 is an integer of 1 to 14,

g115 is an integer of 1 to 18,

when each of g100 to g115 is 2 or more, two or more structures in parentheses are the same as or different from each other, and

is a moiety bonded to chemical formula 1.

According to an exemplary embodiment of the present description, G100 to G115 are the same or different from each other and each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted silyl; or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present description, G100 to G115 are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted, linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted, linear or branched alkylsilyl group of 1 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G115 are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted, linear or branched alkylsilyl group of 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G115 are the same or different from each other and each independently hydrogen; deuterium; unsubstituted or deuterium-substituted straight-chain or branched alkyl having 1 to 30 carbon atoms; unsubstituted or deuterium-substituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms; unsubstituted or deuterium-substituted linear or branched alkylsilyl group having 1 to 30 carbon atoms; or unsubstituted or deuterium-substituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G115 are the same or different from each other and each independently hydrogen; deuterium; unsubstituted or deuterium-substituted straight-chain or branched alkyl having 1 to 20 carbon atoms; unsubstituted or deuterium-substituted monocyclic or polycyclic cycloalkyl having 3 to 20 carbon atoms; unsubstituted or deuterium-substituted linear or branched alkylsilyl group having 1 to 20 carbon atoms; or unsubstituted or deuterium-substituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G115 are the same or different from each other and each independently hydrogen; deuterium; a methyl group; -CD₃(ii) a A tertiary butyl group; a cyclohexyl group; a trimethylsilyl group; or unsubstituted or deuterium substituted phenyl.

According to an exemplary embodiment of the present specification, in chemical formula 2, B1 and B2 are the same as or different from each other, and each is independently an aryl group.

According to an exemplary embodiment of the present specification, in chemical formula 2, B1 and B2 are the same as or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in chemical formula 2, B1 and B2 are the same as or different from each other, and each is independently a phenyl group; or a biphenyl group.

According to an exemplary embodiment of the present specification, in chemical formula 2, B1 and B2 are phenyl groups.

According to an exemplary embodiment of the present specification, in chemical formula 2, B1 and B2 are biphenyl groups.

According to an exemplary embodiment of the present description, R2 to R7 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; substituted or unsubstituted arylalkyl; or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present description, R2 to R7 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted, linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted, linear or branched alkylsilyl group of 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylsilyl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted, linear or branched arylalkyl group having from 6 to 30 carbon atoms; or a substituted or unsubstituted, mono-or polycyclic heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present description, R2 to R7 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted, linear or branched alkylsilyl group of 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylsilyl group having 6 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; substituted or unsubstituted, straight-chain or branched arylalkyl having from 6 to 20 carbon atoms; or a substituted or unsubstituted, mono-or polycyclic heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present description, R2 to R7 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a linear or branched alkyl group having 1 to 30 carbon atoms; monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; monocyclic or polycyclic arylsilyl groups having 6 to 30 carbon atoms; monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; a linear or branched arylalkyl group having from 6 to 30 carbon atoms; a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and the substituent is unsubstituted or substituted with one or more selected from the group consisting of: deuterium, a halogen group, an unsubstituted or deuterium-substituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, and a straight-chain or branched haloalkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present description, R2 to R7 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a linear or branched alkyl group having 1 to 20 carbon atoms; monocyclic or polycyclic cycloalkyl groups having 3 to 20 carbon atoms; a linear or branched alkylsilyl group having 1 to 20 carbon atoms; monocyclic or polycyclic arylsilyl groups having 6 to 20 carbon atoms; monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; a linear or branched arylalkyl group having from 6 to 20 carbon atoms; a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, and the substituent is unsubstituted or substituted with one or more selected from the group consisting of: deuterium, a halogen group, an unsubstituted or deuterium-substituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, and a straight-chain or branched haloalkyl group having 1 to 20 carbon atoms.

According to one embodiment of the present description, R2 to R7 are the same or different from each other and are each independently hydrogen; deuterium; -F; a cyano group; -CD₃(ii) a A methyl group; isopropyl group; a tertiary butyl group; a cyclohexyl group; an adamantyl group; cumyl; a phenyl group; a biphenyl group; a naphthyl group; a trimethylsilyl group; a triphenylsilyl group; a pyridyl group; a triazine group; or carbazolyl, and said substituent is unsubstituted or substituted with one or more selected from: deuterium, -F, -CF ₃、-CD₃And tert-butyl unsubstituted or substituted with deuterium.

Cumyl means

According to an exemplary embodiment of the present description, R2 comprises deuterium.

According to an exemplary embodiment of the present description, R2 is deuterium; -F; a cyano group; -CD₃(ii) a A methyl group; isopropyl group; a tertiary butyl group; a cyclohexyl group; an adamantyl group; cumyl; a phenyl group; a biphenyl group; a naphthyl group; a trimethylsilyl group; a triphenylsilyl group; a pyridyl group; a triazine group; or carbazolyl, and methyl; isopropyl group; a tertiary butyl group; a cyclohexyl group; an adamantyl group; cumyl; a phenyl group; a biphenyl group; a naphthyl group; a trimethylsilyl group; a triphenylsilyl group; a pyridyl group; a triazine group; or carbazolyl is substituted with deuterium.

According to an exemplary embodiment of the present specification, R6 and R7 are bonded to each other to form any one of rings in a structure represented by the following group a.

< group A >

In the above-described structure, the first and second electrodes are formed on the substrate,

g10 is an integer from 1 to 10,

g11 is an integer from 1 to 8,

g12 is an integer from 1 to 6,

when each of g10 to g12 is 2 or more, two or more structures in parentheses are the same as or different from each other,

g1 is 0 or 1 and,

when g1 is 0, the structures in parentheses are directly bonded to each other without a carbon atom,

g2 is 0 or 1, and

when g2 is 0, the structures in parentheses are directly bonded to each other without a carbon atom.

According to an exemplary embodiment of the present description, R6 and R7 are bonded to each other to form any one of the rings in the structure represented by group B of the following structures.

< group B >

In the above-described structure, the first and second electrodes are formed on the substrate,

g100, g101, g108, g109 and g116 to g118 are each an integer of 1 to 8,

g102 and g107 are each an integer of 1 to 12,

g103 and g104 are each an integer of 1 to 10,

g105 and g110 to g113 are each an integer of 1 to 4,

g114 is an integer of 1 to 14,

g115 is an integer of 1 to 18, and

when each of g100 to g118 is 2 or more, two or more structures in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present description, G100 to G120 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted, linear or branched alkylsilyl group of 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G120 are the same as or different from each other, and each is independently hydrogen; deuterium; unsubstituted or deuterium-substituted straight-chain or branched alkyl having 1 to 20 carbon atoms; unsubstituted or deuterium-substituted monocyclic or polycyclic cycloalkyl having 3 to 20 carbon atoms; unsubstituted or deuterium-substituted linear or branched alkylsilyl group having 1 to 20 carbon atoms; or unsubstituted or deuterium-substituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms.

According to one exemplary embodiment of the present specification, at least one of R1 to R7 is a group represented by any one of the structures of the following group C.

< group C >

In the above-described structure, the first and second electrodes are formed on the substrate,

g10 is an integer from 1 to 10,

g11 is an integer from 1 to 8,

when each of g10 and g11 is 2 or more, two or more structures in parentheses are the same as or different from each other,

g1 is 0 or 1 and,

when g1 is 0, the structures in parentheses are directly bonded to each other without a carbon atom,

g2 is 0 or 1 and,

When g2 is 0, the structures in parentheses are directly bonded to each other without a carbon atom, and

is a moiety bonded to chemical formula 1.

According to one exemplary embodiment of the present specification, at least one of R1 to R7 is a group represented by any one of the structures of the following group D.

< group D >

In the above-described structure, the first and second electrodes are formed on the substrate,

g100, g101, g108 and g109 are each an integer of 1 to 8,

g102 and g107 are each an integer of 1 to 12,

g103 and g104 are each an integer of 1 to 10,

g105 and g110 to g113 are each an integer of 1 to 4,

g114 is an integer of 1 to 14,

g115 is an integer of 1 to 18,

when each of g100 to g115 is 2 or more, two or more structures in parentheses are the same as or different from each other, and

Is a moiety bonded to chemical formula 1.

According to an exemplary embodiment of the present description, G100 to G115 are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted, linear or branched alkylsilyl group of 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G115 are the same or different from each other and each independently hydrogen; deuterium; unsubstituted or deuterium-substituted straight-chain or branched alkyl having 1 to 20 carbon atoms; unsubstituted or deuterium-substituted monocyclic or polycyclic cycloalkyl having 3 to 20 carbon atoms; unsubstituted or deuterium-substituted linear or branched alkylsilyl group having 1 to 20 carbon atoms; or unsubstituted or deuterium-substituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present description, G100 to G115 are the same or different from each other and each independently hydrogen; deuterium; a methyl group; -CD ₃(ii) a A tertiary butyl group; a cyclohexyl group; a trimethylsilyl group; or unsubstituted or deuterium substituted phenyl.

According to an exemplary embodiment of the present specification, chemical formula 1 includes: a linear or branched alkyl group having 1 to 10 carbon atoms substituted with deuterium; a monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms substituted with one or more of deuterium and a linear or branched alkyl group having 1 to 10 carbon atoms substituted with deuterium; or monocyclic or polycyclic aliphatic hydrocarbon fused rings having 3 to 10 carbon atoms substituted with one or more of deuterium and a linear or branched alkyl group having 1 to 10 carbon atoms substituted with deuterium.

According to an exemplary embodiment of the present specification, chemical formula 1 includes: deuterium substituted methyl; ethyl substituted with deuterium; deuterium substituted isopropyl group; tert-butyl substituted with deuterium; cyclopentyl substituted with one or more of deuterium and methyl substituted with deuterium; cyclohexyl substituted with one or more of deuterium and methyl substituted with deuterium; cycloheptyl substituted with one or more of deuterium and methyl substituted with deuterium; bicyclo [2.2.1] octyl substituted with one or more of deuterium and methyl substituted with deuterium; norbornyl substituted with one or more of deuterium and methyl substituted with deuterium; adamantyl substituted with one or more of deuterium and methyl substituted with deuterium; a cyclopentane ring substituted with one or more of deuterium and methyl substituted with deuterium; a cyclohexane ring substituted with one or more of deuterium and methyl substituted with deuterium; a cycloheptane ring substituted with one or more of deuterium and a methyl group substituted with deuterium; a bicyclo [2.2.1] octane ring substituted with one or more of deuterium and methyl substituted with deuterium; a norbornane ring substituted with one or more of deuterium and methyl substituted with deuterium; or an adamantane ring substituted with one or more of deuterium and a methyl group substituted with deuterium.

According to one exemplary embodiment of the present specification, chemical formula 1 is any one selected from the following compounds.

The present specification provides an organic light emitting device comprising the above compound. In this specification, when one member is provided "on" another member, this includes not only a case where one member is in contact with another member but also a case where another member is present between the two members.

In this specification, unless specifically described otherwise, when a portion "includes" one constituent element, this does not mean that another constituent element is excluded, but means that another constituent element may also be included.

In the present specification, "layer" has a similar meaning to "film" generally used in the art, and means a coating layer covering a target area. The size of the "layers" is not limited, and the sizes of the respective "layers" may be the same as or different from each other.

According to an exemplary embodiment, the size of the "layer" may be the same as the size of the entire device, may correspond to the size of a particular functional area, and may also be as small as a single sub-pixel.

In the present specification, when a specific a material is contained in the B layer, this means the following two cases: i) the fact that one or more a materials are contained in one B layer; and ii) the fact that the B layer is composed of one or more layers, and the A material is contained in one or more of the B layers of the plurality of layers.

In the present specification, when a specific a material is contained in the C layer or the D layer, this means all of the following cases: i) the fact that the a material is contained in one or more of the C layers having one or more layers; ii) the fact that the A material is contained in one or more of the D layers having one or more layers; and iii) the fact that the A material is contained in each of the C layer having one or more layers and the D layer having one or more layers.

The present specification provides an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer include the compound represented by chemical formula 1.

The organic material layer of the organic light emitting device of the present specification may be composed of a single layer structure, but may also be composed of a multilayer structure in which organic material layers having two or more layers are stacked. For example, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.

In one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by chemical formula 1.

In one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by chemical formula 1 as a dopant of the light emitting layer.

In one exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound represented by chemical formula 1 as a blue fluorescent dopant of the emission layer.

In one exemplary embodiment of the present specification, the organic light emitting device further includes one or two or more layers selected from the group consisting of: a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

In one exemplary embodiment of the present specification, the light emitting layer further includes a host compound.

In one exemplary embodiment of the present specification, the light-emitting layer further contains a host compound, and at least one hydrogen at a substitutable position of the host compound is substituted with deuterium.

In an exemplary embodiment of the present specification, when the host compound is substituted with deuterium, 30% or more of the host compound is substituted with deuterium. In another exemplary embodiment, 40% or more of the host compound is substituted with deuterium. In yet another exemplary embodiment, 60% or more of the host compounds are substituted with deuterium. In yet another exemplary embodiment, 80% or more of the host compound is substituted with deuterium. In yet another embodiment, 100% of the host compounds are substituted with deuterium.

In one exemplary embodiment of the present specification, the light emitting layer further includes a compound represented by the following chemical formula H.

[ chemical formula H ]

In the chemical formula H, the compound represented by the formula,

l20 and L21 are the same or different from each other and are each independently a direct bond; substituted or unsubstituted arylene; or a substituted or unsubstituted heteroarylene group,

ar20 and Ar21 are the same or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, and

r20 is hydrogen; deuterium; a halogen group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently a direct bond; a phenylene group; a biphenylene group; a naphthylene group; a divalent dibenzofuranyl group; or a divalent dibenzothienyl group.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and each independently is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted, mono-or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and each independently is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted, mono-or polycyclic heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

In one exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted anthracenyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted phenalkenyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted benzofluorenyl; substituted or unsubstituted furyl; substituted or unsubstituted thienyl; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted naphthobenzofuranyl group; substituted or unsubstituted dibenzothienyl; or a substituted or unsubstituted naphthobenzothienyl group.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and each independently is phenyl unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; biphenyl unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthyl unsubstituted or substituted with monocyclic or polycyclic aryl having 6 to 20 carbon atoms; dibenzofuranyl which is unsubstituted or substituted by monocyclic or polycyclic aryl having from 6 to 20 carbon atoms; naphthobenzofuranyl which is unsubstituted or substituted by a monocyclic or polycyclic aryl group having from 6 to 20 carbon atoms; dibenzothienyl unsubstituted or substituted by monocyclic or polycyclic aryl having from 6 to 20 carbon atoms; or naphthobenzothienyl which is unsubstituted or substituted by a monocyclic or polycyclic aryl group having from 6 to 20 carbon atoms.

In one exemplary embodiment of the present description, Ar20 is a substituted or unsubstituted heterocyclic group and Ar21 is a substituted or unsubstituted aryl group.

In one exemplary embodiment of the present description, R20 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted, linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted, mono-or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In one exemplary embodiment of the present description, R20 is hydrogen; deuterium; fluorine; a substituted or unsubstituted, linear or branched alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted, mono-or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, when the compound represented by formula H is substituted with deuterium, 30% or more of H at the substitutable position is substituted with deuterium. In another exemplary embodiment, in the structure of formula H, 40% or more of H at the substitutable positions is replaced with deuterium.

In yet another exemplary embodiment, in the structure of formula H, 60% or more of H at the substitutable positions is replaced with deuterium. In still another exemplary embodiment, in the structure of formula H, 80% or more of H at the substitutable positions is substituted with deuterium.

In still another exemplary embodiment, in the structure of formula H, 100% of H at the substitutable positions is replaced with deuterium.

In one exemplary embodiment of the present specification, the compound represented by formula H is any one selected from the following compounds.

In one exemplary embodiment of the present specification, in the light emitting layer, the compound represented by chemical formula 1 is used as a dopant and the compound represented by chemical formula H is used as a host.

In one exemplary embodiment of the present specification, when the light emitting layer includes a host and a dopant, the content of the dopant may be selected in the range of 0.01 parts by weight to 10 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

In one exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant, and the host and the dopant are included in a weight ratio of 99:1 to 1:99, preferably 99:1 to 70:30, and more preferably 99:1 to 90: 10.

The light-emitting layer may further contain a host material, and examples of the host include a fused aromatic ring derivative, a heterocyclic ring-containing compound, and the like. Specifically, examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, triazine derivatives, and the like, and examples thereof may be a mixture of two or more thereof, but are not limited thereto.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes two or more mixed dopants and a host.

According to an exemplary embodiment of the present specification, one or more of the two or more mixed dopants includes chemical formula 1, and the host includes a compound represented by chemical formula H. One or more of the two or more mixed dopants include chemical formula 1, and the rest may use a dopant material known in the related art, but the present invention is not limited thereto.

According to an exemplary embodiment of the present specification, one or more of the two or more mixed dopants include chemical formula 1, and the rest may use one or more of a boron-based compound, a pyrene-based compound and a delayed fluorescence-based compound, which are different from the compound of chemical formula 1, but the present invention is not limited thereto.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes one or more hosts.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes two or more mixed hosts.

According to one exemplary embodiment of the present description, one or more of the two or more mixed hosts is a compound represented by formula H.

According to an exemplary embodiment of the present specification, two or more mixed hosts are different from each other and each independently is a compound represented by formula H.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes two mixed hosts.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer including two mixed hosts, the two mixed hosts are different from each other, and the two hosts are a compound represented by chemical formula H.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and includes: a first body represented by formula H; and a second body represented by chemical formula H, and the first body and the second body are different from each other.

According to an exemplary embodiment of the present description, the first body to the second body are comprised in a weight ratio of 95:5 to 5:95, preferably in a weight ratio of 70:30 to 30: 70.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes one or more hosts, and a dopant.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes one or more hosts, and a dopant, the hosts include a compound represented by chemical formula H, and the dopant includes a compound represented by chemical formula 1.

According to an exemplary embodiment of the present specification, one or more of the two or more mixed hosts includes a compound represented by chemical formula H and the dopant includes a compound represented by chemical formula 1.

In the present specification, the two or more mixed bodies are different from each other.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes two mixed hosts, and a dopant.

According to an exemplary embodiment of the present specification, the two mixed hosts are different from each other and each independently include a compound represented by chemical formula H, and the dopant includes a compound represented by chemical formula 1.

According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and includes: a first body represented by formula H; a second body represented by formula H; and a dopant represented by chemical formula 1, and the first body and the second body are different from each other.

According to an exemplary embodiment of the present specification, one or more hosts and one or more dopants are used in an organic material layer, the one or more hosts include a compound represented by chemical formula H, and the one or more dopants include a compound represented by chemical formula 1.

According to an exemplary embodiment of the present specification, two or more mixed hosts and two or more mixed dopants are used in the organic material layer, the same materials as described above may be used in the two or more mixed hosts, and the same materials as described above may be used in the two or more mixed dopants.

In one exemplary embodiment of the present specification, an organic light emitting device includes: a first electrode; a second electrode; a light-emitting layer provided between the first electrode and the second electrode; and an organic material layer having two or more layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the compound represented by chemical formula 1.

In one exemplary embodiment of the present specification, as the organic material layer having two or more layers, two or more may be selected from a light emitting layer, a hole transporting layer, a hole injecting layer, a layer simultaneously transporting and injecting holes, and an electron blocking layer.

In one exemplary embodiment of the present specification, the organic material layer includes an electron transport layer having two or more layers, and at least one of the electron transport layer having two or more layers includes the compound represented by chemical formula 1. Specifically, in one exemplary embodiment of the present specification, the compound represented by chemical formula 1 may be included in one layer of electron transport layers having two or more layers, and may also be included in each of the electron transport layers having two or more layers.

Further, in one exemplary embodiment of the present specification, when the compound is included in each of the electron transport layers having two or more layers, other materials than the compound represented by chemical formula 1 may be the same as or different from each other.

When the organic material layer including the compound represented by chemical formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, a metal or a metal complex can be used. For example, the electron transport layer including the compound represented by chemical formula 1 may further include lithium quinolate (LiQ).

In one exemplary embodiment of the present specification, the organic material layer includes a hole transport layer having two or more layers, and at least one of the hole transport layer having two or more layers includes the compound represented by chemical formula 1. Specifically, in one exemplary embodiment of the present specification, the compound represented by chemical formula 1 may be included in one layer of hole transport layers having two or more layers, and may also be included in each of the hole transport layers having two or more layers.

Further, in one exemplary embodiment of the present specification, when the compound represented by chemical formula 1 is included in each of the hole transport layers having two or more layers, other materials than the compound represented by chemical formula 1 may be the same as or different from each other.

In one exemplary embodiment of the present specification, the organic material layer may include a hole injection layer or a hole transport layer including a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic material layer including the compound represented by chemical formula 1.

In one exemplary embodiment of the present description, the first electrode is an anode or a cathode.

In one exemplary embodiment of the present description, the second electrode is a cathode or an anode.

In one exemplary embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, an organic material layer having one or more layers, and a cathode are sequentially stacked on a substrate.

In one exemplary embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.

For example, fig. 1 to 3 illustrate the structure of an organic light emitting device according to an exemplary embodiment of the present specification. Fig. 1 to 3 illustrate the organic light emitting device, and the organic light emitting device is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked. In the above structure, the compound may be contained in the light-emitting layer 3.

Fig. 2 shows an example of an organic light emitting device in which a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 8, an electron blocking layer 9, a light emitting layer 3, a hole blocking layer 6, an electron injection and transport layer 7, and a second electrode 4 are sequentially stacked. In the above structure, the compound may be contained in one or more layers of the light emitting layer 3, the hole blocking layer 6, the electron injection and transport layer 7, and the electron injection layer 8.

Fig. 3 shows an example of an organic light emitting device in which a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 8, an electron blocking layer 9, a light emitting layer 3, a first electron transport layer 10, a second electron transport layer 11, an electron injection layer 12, and a second electrode 4 are sequentially stacked. In the above structure, the compound may be contained in the light-emitting layer 3.

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that one or more layers of the organic material layer include the compound, i.e., the compound represented by chemical formula 1.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device of the present specification can be manufactured by: a positive electrode is formed by depositing a metal, or a metal oxide having conductivity, or an alloy thereof on a substrate using a Physical Vapor Deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the positive electrode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to the above-described method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, in manufacturing the organic light emitting device, the compound represented by chemical formula 1 may be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In addition to the above-described methods, an organic light emitting device may be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate (international publication No. 2003/012890). However, the manufacturing method is not limited thereto.

As the first electrode material, a material having a high work function is generally preferable to facilitate hole injection into the organic material layer. Examples thereof include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SnO₂Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole and polyaniline; and the like, but are not limited thereto.

As the second electrode material, a material having a low work function is generally preferred to facilitate electron injection into the organic material layer. Examples thereof include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO ₂Al; and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. Examples of the host material include a fused aromatic ring derivative or a heterocyclic ring-containing compound and the like. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and specific examples of the heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but the examples are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like, in addition to the compound represented by chemical formula 1. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and examples thereof include pyrene, anthracene, having an arylamine group,Diindenopyrene, and the like. Further, the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. Further, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto.

In this specification, when the compound represented by chemical formula 1 is contained in an organic material layer other than the light emitting layer or provided with an additional light emitting layer, the light emitting material of the light emitting layer is a material that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and the electrons, and is preferably a material having high quantum efficiency for fluorescence or phosphorescence. Examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; based on benzeneOxazole, benzothiazole-based and benzimidazole-based compounds; polymers based on poly (p-phenylene vinylene) (PPV); a spiro compound; a polyfluorene; rubrene; and the like, but are not limited thereto.

The hole injection layer is a layer that injects holes from the electrode. The hole injection material has the ability to transport holes, so that preferably the hole injection material has an effect of injecting holes in the first electrode and an excellent hole injection effect to the light-emitting layer or the light-emitting material. Further, the hole injection material is preferably a material excellent in the ability to prevent excitons generated from the light emitting layer from moving to the electron injection layer or the electron injection material. The hole injection material is preferably a material having excellent ability to form a thin film. Further, the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is preferably a value between the work function of the first electrode material and the HOMO of the adjacent organic material layer. Specific examples of the hole injection material include: a metalloporphyrin; an oligothiophene; an arylamine-based organic material; a carbazole-based organic material; a nitrile-based organic material; a hexanitrile hexaazatriphenylene-based organic material; quinacridone-based organic materials; a perylene-based organic material; polythiophene-based conductive polymers such as anthraquinone and polyaniline, etc.; or a mixture of two or more of the examples; and the like, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is preferably a material having high hole mobility that can receive holes from the first electrode or the hole injection layer and transfer the holes to the light emitting layer. Specific examples thereof include arylamine-based organic materials, carbazole-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material preferably can well receive electrons from the second electrode and transfer the electrons to the light emitting layerA material having a high electron mobility. Specific examples thereof include: al complexes of 8-hydroxyquinoline; comprising Alq₃The complex of (1); an organic radical compound; a hydroxyflavone-metal complex; a triazine derivative; LiQ; and the like, but are not limited thereto. The electron transport layer may be used with any desired first electrode material as used according to the related art. In particular, suitable examples of the first electrode material are typical materials having a low work function followed by an aluminum or silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.

The electron injection layer is a layer that injects electrons from the electrode. Preferably, the electron injection material is excellent in an ability to transport electrons, and has an effect of injecting electrons from the second electrode and an excellent electron injection effect to the light emitting layer or the light emitting material. Further, the electron injection material is preferably a material which prevents excitons generated from the light-emitting layer from moving to the hole injection layer and which is excellent in the ability to form a thin film. Specific examples thereof include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, and the like,Azole,Oxadiazole, triazole, triazine, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, mixtures of two or more of the examples, and the like, but are not limited thereto.

Examples of the metal complex compounds include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), chlorogallium bis (2-methyl-8-quinolinolato), gallium bis (2-methyl-8-quinolino) (o-cresol), aluminum bis (2-methyl-8-quinolino) (1-naphthol), gallium bis (2-methyl-8-quinolino) (2-naphthol), and the like, but are not limited thereto.

The electron blocking layer is a layer that can improve the lifetime and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole injection layer. As the electron blocking layer, a known material may be used without limitation, and the electron blocking layer may be formed between the light emitting layer and the hole injection layer or between the light emitting layer and the layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that blocks holes from passing through the light emitting layer and reaching the negative electrode, and may be generally formed under the same conditions as those of the electron injection layer. Specific examples thereof includeAn oxadiazole derivative or a triazole derivative, a phenanthroline derivative, an aluminum complex, pyridine, pyrimidine or triazine derivative, and the like, but is not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type, depending on the material used.

In one exemplary embodiment of the present specification, the compound represented by chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

Even in an organic light emitting device including an organic phosphorescent device, an organic solar cell, an organic photoconductor, an organic transistor, or the like, the compound according to the present specification can operate by a principle similar to that applied to the organic light emitting device. For example, the organic solar cell may have a structure including a negative electrode, a positive electrode, and a photoactive layer disposed between the negative electrode and the positive electrode, and the photoactive layer may include the compound.

The organic light emitting device of the present specification may be manufactured using typical manufacturing methods and materials of organic light emitting devices, except that the above-described compounds are used to form an organic material layer having one or more layers.

EMBODIMENTS FOR CARRYING OUT THE INVENTION

Hereinafter, the present specification will be described in detail with reference to examples, comparative examples, and the like for specifically describing the present specification. However, the embodiments and comparative examples according to the present specification may be modified into various forms, and should not be construed that the scope of the present specification is limited to the embodiments and comparative examples described in detail below. The examples and comparative examples of the present specification are provided to more fully illustrate the present specification to those of ordinary skill in the art.

Synthesis example 1 Synthesis of Compound 1

<1-a > preparation of Compound 1-a

After 1-bromo-3-chloro-5-methylbenzene (1 equivalent) and bis (4-tert-butylphenyl) amine (1 equivalent) were dissolved in toluene (0.3M) in a three-necked flask and sodium tert-butoxide (1.2 equivalents) and bis (tri-tert-butylphosphine) palladium (0) (0.01 equivalent) were added thereto, the resulting mixture was stirred under reflux conditions for 2 hours under an argon atmosphere. When the reaction was complete, the flask was cooled to room temperature, and H was added thereto₂O, and the reaction solution was transferred to a separatory funnel for extraction. Extracting with MgSO 2 ₄Dried and concentrated, and the sample was purified by silica gel column chromatography to obtain compound 1-a. (yield 86%, MS [ M + H ]]⁺＝407)

<1-b > preparation of Compound 1-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 1-a and N- (4-tert-butylphenyl) -4,4,7, 7-tetramethyl-4, 5,6, 7-tetrahydrobenzo [ b ] was used]Thiophen-3-amine was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 68%, MS [ M + H ]]⁺＝712)

<1-c > preparation of Compound 1-c

After the compound 1-b was dissolved in 1, 2-dichlorobenzene (0.1M) and boron triiodide (2 equivalents) was added thereto in a three-necked flask, the resulting mixture was stirred at 160 ℃ for 5 hours under an argon atmosphere. The reaction product was cooled to 0 ℃, N-diisopropylethylamine (20 equivalents) was added thereto, and the resulting mixture was stirred for 1 hour. Using toluene and H₂The O was extracted in a separatory funnel. Extracting with MgSO 2₄Dried and concentrated, and the sample was purified by silica gel column chromatography to obtain compound 1-c. (yield 22%, MS [ M + H ]]⁺＝719)

<1-d > preparation of Compound 1

Compounds 1-C (1 equivalent), 10% Pt/C (0.05 equivalent), isopropanol (2.5M), cyclohexane (0.3M) and D₂O (0.15M) was placed in a two-necked flask, and the resulting mixture was stirred under an argon atmosphere under reflux for 24 hours. When the reaction was complete, the flask was cooled to room temperature and the reaction product was then filtered through celite. The filtrate was transferred to a separatory funnel, extraction was performed using toluene, and the extract was extracted with MgSO ₄Dried and concentrated, and then subjected to sublimation purification by silica gel column chromatography to obtain compound 1. (yield 69%, MS [ M + H ]]⁺＝732)

Synthesis example 2 Synthesis of Compound 2

<2-a > preparation of Compound 2-a

Bis (2, 2-dimethyl-2, 3-dihydro-1H-inden-5-yl) amine (1 eq), 10% Pt/C (0.05 eq), isopropanol (2.5M), cyclohexane (0.3M) and D₂O (0.15M) was placed in a two-necked flask, and the resulting mixture was stirred under an argon atmosphere under reflux for 24 hours. When it is reversedWhen this was complete, the flask was cooled to room temperature and the reaction product was then filtered through celite. The filtrate was transferred to a separatory funnel, extraction was performed using toluene, and the extract was extracted with MgSO₄Dried and concentrated, and then the sample was purified by silica gel chromatography to obtain compound 2-a. (yield 82%, MS [ M + H ]]⁺＝306)

<2-b > preparation of Compound 2-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 2-a and 1-bromo-3-chloro-5- (methyl-d) were used to obtain the compound 2-b₃) Benzene replaces 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 79%, MS [ M + H ]]⁺＝440)

<2-c > preparation of Compound 2-c

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 2-b and N- (2, 2-dimethyl-2, 3-dihydro-1H-inden-5-yl) -5, 5-dimethyl-5, 6-dihydro-4-H-cyclopenta [ b ] were used to obtain the compound 2-c ]Furan-2-amine was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 81%, MS [ M + H ]]⁺＝698)

<2-d > preparation of Compound 2

After compound 2-c was dissolved in 1, 2-dichlorobenzene (0.1M) and boron triiodide (2 equivalents) was added thereto in a three-necked flask, the resulting mixture was stirred at 160 ℃ for 5 hours under an argon atmosphere. The reaction product was cooled to 0 ℃, N-diisopropylethylamine (20 equivalents) was added thereto, and the resulting mixture was stirredStirring for 1 hour. Using toluene and H₂The O was extracted in a separatory funnel. Extracting with MgSO 2₄Dried and concentrated, and the sample was subjected to sublimation purification with silica gel column chromatography to obtain compound 2. (yield 16%, MS [ M + H ]]⁺＝705)

Synthesis example 3 Synthesis of Compound 3

<3-a > preparation of Compound 3-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that 1-bromo-3, 5-dichlorobenzene was used instead of 1-bromo-3-chloro-5-methylbenzene to obtain compound 3-a. (yield 92%, MS [ M + H ]]⁺＝427)

<3-b > preparation of Compound 3-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 3-a and N- (4-tert-butylphenyl) -4, 7-dimethyl-4, 5,6, 7-tetrahydro-4, 7-ethanobenzo [ b ] were used ]Thiophen-3-amine was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 74%, MS [ M + H ]]⁺＝730)

<3-c > preparation of Compound 3-c

By the following synthetic example<1-c>The preparation was carried out in the same manner as in (1) except that the compound 3-b was used instead of the compound 1-b to obtain the compound 3-c. (yield 31%, MS [ M + H ]]⁺＝738)

<3-d > preparation of Compound 3-d

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) to obtain the compound 3-d except that the compound 3-c and 10, 10-dimethyl-5, 10-dihydroindeno [1,2-b ] were used]Indole replaces 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 83%, MS [ M + H ]]⁺＝935)

<3-e > preparation of Compound 3

By the following synthetic example<1-d>The preparation was carried out in the same manner as in (1) except that the compound 3-d was used instead of the compound 1-c to obtain the compound 3. (yield 59%, MS [ M + H ]]⁺＝956)

Synthesis example 4 Synthesis of Compound 4

<4-a > preparation of Compound 4-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) to obtain compound 4-a except that compound 3-a and N- (4-tert-butylphenyl) -5- (2,4, 6-tris (methyl-d) were used₃) Phenyl) furan-3-amine in place of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 55%, MS [ M + H ] ]⁺＝733)

<4-b > preparation of Compound 4-b

By the following synthetic example<1-c>The preparation was carried out in the same manner as in (1) except that the compound 4-a was used instead of the compound 1-b to obtain the compound 4-b. (yield 25%, MS [ M + H ]]⁺＝741)

<4-c > preparation of Compound 4

In a three-necked flask, compound 4-b (1 eq.) and 6, 6-dimethyl-5, 6-dihydroindeno [2,1-b ] were placed]After indole (1 equivalent) was dissolved in toluene (0.3M) and sodium tert-butoxide (1.2 equivalents) and bis (tri-tert-butylphosphine) palladium (0) (0.01 equivalent) were added thereto, the resulting mixture was stirred under reflux conditions for 6 hours under an argon atmosphere. When the reaction was complete, the flask was cooled to room temperature, and H was added thereto₂O, and the reaction solution was transferred to a separatory funnel for extraction. Extracting with MgSO 2₄Dried and concentrated, and the sample was subjected to sublimation purification with silica gel column chromatography to obtain compound 4. (yield 66%, MS [ M + H ]]⁺＝938)

Synthesis example 5 Synthesis of Compound 5

<5-a > preparation of Compound 5-a

In a three-necked flask, 1, 3-dibromo-5-chlorobenzene (1 equivalent) and 4-tert-butylbenzene-2, 3,5,6-d were placed_-4After the amine (2 equivalents) was dissolved in toluene (0.2M) and sodium tert-butoxide (2.5 equivalents) and bis (tri-tert-butylphosphine) palladium (0) (0.015 equivalent) were added thereto, the resulting mixture was stirred under reflux conditions for 3 hours under an argon atmosphere. When the reaction was complete, the flask was cooled to room temperature, and H was added thereto ₂O, and the reaction solution was transferred to a separatory funnel for extraction. Extracting with MgSO 2₄Dried and concentrated, and the sample was purified by silica gel column chromatography to obtain compound 5-a. (yield 93%, MS [ M + H ]]⁺＝416)

<5-b > preparation of Compound 5-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 5-a and 1- (2- (3-bromophenyl-2, 4,5, 6-d) were used to obtain the compound 5-b₄) Prop-2-yl) benzene-2, 3,4,5,6-d₅In place of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 65%, MS [ M + H ]]⁺＝619)

<5-c > preparation of Compound 5-c

By the following synthetic example<1-a>The production was carried out in the same manner as in (1) except that the compound 5-b and 3-bromo-5-tert-butylbenzo [ b ] were used to obtain the compound 5-c]Thiophene-2, 4,6,7-d₄In place of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 79%, MS [ M + H ]]⁺＝811)

<5-d > preparation of Compound 5-d

Compound 5-d was obtained by conducting the preparation in the same manner as in Synthesis example <1-c > except that Compound 5-c was used in place of Compound 1-b. (yield 24%, MS [ M + H ] + ═ 817)

<5-e > preparation of Compound 5

By the following synthetic example<4-c>The preparation was carried out in the same manner as in (1) to obtain compound 5, except that compound 5-d and bis (phenyl-d) were used ₅) Amine instead of Compounds 4-b and 6, 6-dimethyl-5, 6-dihydroindeno [2,1-b ]]Indole. (yield 49%, MS [ M + H ]]⁺＝960)

Synthesis example 6 Synthesis of Compound 6

<6-a > preparation of Compound 6-b

To prepare examples<1-a>In the same manner as in (1) from compound 5-a and 1-bromo-4-tert-butyl-phenyl-2, 4,5,6-d₄Compound 6-b is obtained. (yield 83%, MS [ M + H ]]⁺＝552)

<6-b > preparation of Compound 6-c

By the following synthetic example<1-a>The production was carried out in the same manner as in (1) except that the compound 6-b and 3-bromo-5-tert-butylbenzo [ b ] were used to obtain the compound 6-c]Thiophene-2, 4,6,7-d₄In place of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 79%, MS [ M + H ]]⁺＝811)

<6-c > preparation of Compound 6-d

To prepare examples<1-c>Compound 6-d was obtained in the same manner as in (1) except that Compound 6-c was used instead of Compound 1-b. (yield 24%, MS [ M + H ]]⁺＝817)

<6-d > preparation of Compound 6

By the following synthetic example<4-c>The preparation was carried out in the same manner as in (1) except that the compound 6-d and 4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole-5, 6,7,8-d were used to obtain the compound 6₄Instead of the compounds 4-b and 6, 6-dimethyl-5, 6-dihydroindeno [2,1-b ]]Indole. (yield 49%, MS [ M + H ]]⁺＝902)

Synthesis example 7 Synthesis of Compound 7

<7-a > preparation of Compound 7-a

By the following synthetic example <1-a>The preparation was carried out in the same manner as in (1-bromo-3, 5-dichlorobenzene) and N- (5-tert-butyl- [1,1' -biphenyl) to obtain the compound 7-a, except that]-2-yl-2 ',3,3',4,4',5',6,6' -d₈) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalene-1, 3,4-d₃-2-amine instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 88%, MS [ M + H ]]⁺＝568)

<7-b > preparation of Compound 7-b

By the following synthetic example<1-a>The production was carried out in the same manner as in (1) except that the compound 7-a and N- (4-tert-butylphenyl-2, 3,5,6-d were used to obtain the compound 7-b₄) Benzo [ b ]]Thiophene-d₅-3-amine instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 51%, MS [ M + H ]]⁺＝822)

<7-c > preparation of Compound 7-c

By the following synthetic example<1-c>The preparation was carried out in the same manner as in (1) except that the compound 7-b was used instead of the compound 1-b to obtain the compound 7-c. (yield 29%, MS [ M + H ]]⁺＝828)

<7-d > preparation of Compound 7

By the following synthetic example<4-c>The preparation was carried out in the same manner as in (1) to obtain Compound 7, except that Compound 7-c and bis (phenyl-d) were used₅) Amine instead of Compounds 4-b and 6, 6-dimethyl-5, 6-dihydroindeno [2,1-b ]]Indole. (yield 49%, MS [ M + H ]]⁺＝971)

Synthesis example 8 Synthesis of Compound 8

<8-a > preparation of Compound 8-a

By the following synthetic example<5-a>The preparation was carried out in the same manner as in (1) except that 1, 3-dibromo-5- (methyl-d) was used to obtain the compound 8-a₃) Benzene was substituted for 1, 3-dibromo-5-chlorobenzene. (yield 95%, MS [ M + H ]]⁺＝398)

<8-b > preparation of Compound 8-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) to obtain the compound 8-b except that the compound 8-a and (3-bromophenyl-2, 4,5, 6-d) were used₄) Trimethylsilane was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 82%, MS [ M + H ]]⁺＝550)

<8-c > preparation of Compound 8-c

By the following synthetic example<1-a>The production was carried out in the same manner as in (1) except that the compound 8-b and 3-bromo-5-tert-butylbenzo [ b ] were used to obtain the compound 8-c]Thiophene-2, 4,6,7-d₄In place of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 81%, MS [ M + H ]]⁺＝742)

<8-d > preparation of Compound 8

By the following synthetic example<2-d>The preparation was carried out in the same manner as in (1) to obtain compound 8, except that compound 8-c was used instead of compound 2-c. (yield 15%, MS [ M + H ]]⁺＝748)

Synthesis example 9 Synthesis of Compound 9

<9-a > preparation of Compound 9-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1-bromo-3, 5-dichlorobenzene) and bis (2, 2-dimethyl-2, 3-dihydro-1H-inden-5-yl-4, 6, 7-d) to obtain compound 9-a, except that ₃) Amines were substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 88%, MS [ M + H ]]⁺＝456)

<9-b > preparation of Compound 9-b

By the following synthetic example<1-a>The production was carried out in the same manner as in (1) except that the compound 9-a and N- (4-tert-butylphenyl-2, 3,5,6-d were used to obtain the compound 9-b₄) Benzofuran-d₅-2-amine instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 62%, MS [ M + H ]]⁺＝694)

<9-c > preparation of Compound 9-c

By the following synthetic example<1-c>Prepared in the same manner as inTo obtain compound 9-c, except that compound 9-b was used instead of compound 1-b. (yield 25%, MS [ M + H ]]⁺＝700)

<9-d > preparation of Compound 9

By the following synthetic example<4-c>The preparation was carried out in the same manner as in (1) to obtain compound 9, except that compound 9-c and bis (phenyl-d) were used₅) Amine instead of Compounds 4-b and 6, 6-dimethyl-5, 6-dihydroindeno [2,1-b ]]Indole. (yield 65%, MS [ M + H ]]⁺＝843)

Synthesis example 10 Synthesis of Compound 10

<10-a > preparation of Compound 10-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1-bromo-3-chloro-5-methylbenzene) except that 1-bromo-N- (4-tert-butylphenyl) benzo [ b ] was used]Thiophen-3-amine was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 67%, MS [ M + H ] ]⁺＝462)

<10-b > preparation of Compound 10-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 10-a and 5-tert-butyl-N- (4-tert-butylphenyl) benzofuran-3-amine were used instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine to obtain the compound 10-b. (yield 52%, MS [ M + H ]]⁺＝747)

<10-c > preparation of Compound 10-c

By the following synthetic example<1-c>The preparation was carried out in the same manner as in (1) except that the compound 10-b was used instead of the compound 1-b to obtain the compound 10-c. (yield 29%, MS [ M + H ]]⁺＝755)

<10-d > preparation of Compound 10

By the following synthetic example<1-d>The preparation was carried out in the same manner as in (1) except that the compound 10-c was used instead of the compound 1-c to obtain the compound 10. (yield 59%, MS [ M + H ]]⁺＝771)

Synthesis example 11 Synthesis of Compound 11

<11-a > preparation of Compound 11-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1-bromo-3, 5-dichlorobenzene) and (5-tert-butyl-N- (4-tert-butylphenyl) benzo [ b ] to obtain compound 11-a, except that]Thiophen-3-amine was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 83%, MS [ M + H ]]⁺＝482)

<11-b > preparation of Compound 11-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 11-a and N- (4-tert-butylphenyl) benzofuran-2-amine were used instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine to obtain the compound 11-b. (yield 62%, MS [ M + H ] ]⁺＝711)

<11-c > preparation of Compound 11-c

By the following synthetic example<1-c>The preparation was carried out in the same manner as in (1) except that the compound 11-b was used instead of the compound 1-b to obtain the compound 11-c. (yield 23%, MS [ M + H ]]⁺＝719)

<11-d > preparation of Compound 11-d

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 11-c and bis (4-t-butylphenyl) amine were used instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-t-butylphenyl) amine to obtain the compound 11-d. (yield 67%, MS [ M + H ]]⁺＝964)

<11-e > preparation of Compound 11

By the following synthetic example<1-d>The preparation was carried out in the same manner as in (1) except that the compound 11-d was used instead of the compound 1-c to obtain the compound 11. (yield 47%, MS [ M + H ]]⁺＝989)

Synthesis example 12 Synthesis of Compound 12

<12-a > preparation of Compound 12-a

By the following synthetic example<2-a>The preparation was carried out in the same manner as in (1) to obtain the compound 12-a except that N- ([1,1' -biphenylyl) was used]-3-yl) -7-tert-butyldibenzo [ b, d]Furan-2-amine substitutionBis (2, 2-dimethyl-2, 3-dihydro-1H-inden-5-yl) amine. (yield 73%, MS [ M + H ]]⁺＝407)

<12-b > preparation of Compound 12-b

By the following synthetic example<2-a>The preparation was carried out in the same manner as in (1) except that 8-tert-butyl-N- (4-phenoxyphenyl) dibenzo [ b, d ] was used to obtain compound 12-b ]Furan-3-amine instead of bis (2, 2-dimethyl-2, 3-dihydro-1H-inden-5-yl) amine. (yield 68%, MS [ M + H ]]⁺＝423)

<12-c > preparation of Compound 12-c

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 12-a and 1-bromo-3-chloro-5-methylbenzene were used in place of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine to obtain the compound 12-c. (yield 84%, MS [ M + H ]]⁺＝531)

<12-d > preparation of Compound 12-d

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 12-c and the compound 12-b were used in place of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine to obtain the compound 12-d. (yield 71%, MS [ M + H ]]⁺＝917)

<12-e > preparation of Compound 12

By the reaction withExample (b)<2-d>The preparation was carried out in the same manner as in (1) to obtain compound 12, except that compound 12-d was used instead of compound 2-c. (yield 16%, MS [ M + H ]]⁺＝923)

Synthesis example 13 Synthesis of Compound 13

<13-a > preparation of Compound 13-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that 5-tert-butyl-N- (3- (2-phenylprop-2-yl) phenyl) - [1,1' -biphenylyl ] was used to obtain the compound 13-a]-2-amine instead of bis (4-tert-butylphenyl) amine. (yield 90%, MS [ M + H ] ]⁺＝544)

<13-b > preparation of Compound 13-b

By the following synthetic example<1-a>The production was carried out in the same manner as in (1) except that the compound 13-a and N- (4-tert-butylphenyl-2, 3,5,6-d were used to obtain the compound 13-b₄) -2- (phenyl-d)₅) Benzofuran-3, 6,7-d₃-4-amine instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 72%, MS [ M + H ]]⁺＝861)

<13-c > preparation of Compound 13

By the following synthetic example<2-d>The preparation was carried out in the same manner as in (1) to obtain compound 13, except that compound 13-b was used instead of compound 2-c. (yield 22%, MS [ M + H ]]⁺＝869)

Synthesis example 14 Synthesis of Compound 14

<14-a > preparation of Compound 14-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1-bromo-3, 5-dichlorobenzene) and bis ((3-propan-2-yl-d) to obtain compound 14-a, except that₆) Phenyl) amine instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 93%, MS [ M + H ]]⁺＝410)

<14-b > preparation of Compound 14-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 14-a and N- (4-tert-butylphenyl) -6,6,9, 9-tetramethyl-6, 7,8, 9-tetrahydrodibenzo [ b, d ] were used to obtain the compound 14-b]Thiophen-3-amine was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 78%, MS [ M + H ] ]⁺＝765)

<14-c > preparation of Compound 14-c

By the following synthetic example<1-c>The preparation was carried out in the same manner as in (1) except that the compound 14-b was used instead of the compound 1-b to obtain the compound 14-c. (yield 84%, MS [ M + H ]]⁺＝529)

<14-d > preparation of Compound 14

By the following synthetic example<4-c>The preparation was carried out in the same manner as in (1) to obtain compound 14, except that compound 14-c and 6-cyclohexyl-4 a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbo-xide were usedAzole instead of Compounds 4-b and 6, 6-dimethyl-5, 6-dihydroindeno [2,1-b ]]Indole. (yield 64%, MS [ M + H ]]⁺＝1020)

Synthesis example 15 Synthesis of Compound 15

<15-a > preparation of Compound 15-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1-bromo-3-chloro-5-tert-butylphenyl) and N- (4-tert-butylphenyl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphtho [2,3-b ] to obtain compound 15-a, except that]Furan-3-amine replaces 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 88%, MS [ M + H ]]⁺＝542)

<15-b > preparation of Compound 15-b

By the following synthetic example<1-a>The production was carried out in the same manner as in (1) except that the compound 15-a and N- (4-tert-butylphenyl-2, 3,5,6-d were used to obtain the compound 15-b₄) Benzofuran-2, 3,4,7-d ₄-5-amine instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 76%, MS [ M + H ]]⁺＝779)

<15-c > preparation of Compound 15

By the following synthetic example<2-d>The preparation was carried out in the same manner as in (1) to obtain compound 15, except that compound 15-b was used instead of compound 2-c. (yield 17%, MS [ M + H ]]⁺＝787)

Synthesis example 16 Synthesis of Compound 16

<16-a > preparation of Compound 16-a

By the following synthetic example<5-a>The preparation was carried out in the same manner as in (1) except that 1, 3-dibromo-5- (methyl-d) was used to obtain compound 16-a₃) Benzene and 4-tert-butylaniline instead of 1, 3-dibromo-5-chlorobenzene and 4-tert-butylbenzene-2, 3,5,6-d_-4-an amine. (yield 92%, MS [ M + H ]]⁺＝390)

<16-b > preparation of Compound 16-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) to obtain compound 16-b except that compound 16-a and 8-bromo-1, 4-dimethyl-1, 2,3, 4-tetrahydro-1, 4-ethanodibenzo [ b, d ] were used]Furan was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 85%, MS [ M + H ]]⁺＝614)

<16-c > preparation of Compound 16-c

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that the compound 16-b and 3-bromo-5- (2-phenylprop-2-yl) benzofuran were used instead of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine to obtain the compound 16-c. (yield 65%, MS [ M + H ] ]⁺＝848)

<16-d > preparation of Compound 16

By the following synthetic example<2-d>The preparation was carried out in the same manner as in (1) to obtain Compound 16, except thatCompound 16-c replaces compound 2-c. (yield 18%, MS [ M + H ]]⁺＝856)

Synthesis example 17 Synthesis of Compound 17

<17-a > preparation of Compound 17-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1-bromo-3-chloro-5- (trifluoromethoxy) benzene and N- (4-tert-butylphenyl) -6,6,9, 9-tetramethyl-6, 7,8, 9-tetrahydrodibenzo [ b, d ] to obtain compound 17-a, except that]Thiophen-3-amine was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 72%, MS [ M + H ]]⁺＝586)

<17-b > preparation of Compound 17-b

By the following synthetic example<1-a>The production was carried out in the same manner as in (1) except that the compound 17-a and N- (5-tert-butyl- [1,1' -biphenylyl) were used to obtain the compound 17-b]-2-yl) -6- (phenyl-d₅) Benzofuran-2-amine replaces 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 81%, MS [ M + H ]]⁺＝972)

<17-c > preparation of Compound 17

By the following synthetic example<2-d>The preparation was carried out in the same manner as in (1) to obtain compound 17, except that compound 17-b was used instead of compound 2-c. (yield 17%, MS [ M + H ] ]⁺＝980)

Synthesis example 18 Synthesis of Compound 18

<18-a > preparation of Compound 18-a

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) except that 1-bromo-3-chloro-5- (methyl-d) was used to obtain compound 18-a₃) Benzene and 8- (2- (methyl-d)₃) Prop-2-yl-1, 1,1,3,3,3-d₆) -N- (4- (2- (methyl-d)₃) Prop-2-yl-1, 1,1,3,3,3-d₆) Phenyl) dibenzo [ b, d]Furan-2-amine was substituted for 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 87%, MS [ M + H ]]⁺＝517)

<18-b > preparation of Compound 18-b

By the following synthetic example<1-a>The preparation was carried out in the same manner as in (1) to obtain compound 18-b, except that compound 18-a and 5- (2- (methyl-d) were used₃) Prop-2-yl-1, 1,1,3,3,3-d₆) -N- (4- (2- (methyl-d)₃) Prop-2-yl-1, 1,1,3,3,3-d₆) Phenyl) furan-3-amine in place of 1-bromo-3-chloro-5-methylbenzene and bis (4-tert-butylphenyl) amine. (yield 74%, MS [ M + H ]]⁺＝770)

<18-c > preparation of Compound 18

By the following synthetic example<2-d>The preparation was carried out in the same manner as in (1) to obtain compound 18, except that compound 18-b was used instead of compound 2-c. (yield 22%, MS [ M + H ]]⁺＝778)

Synthesis example 19 Synthesis of Compound 19

<19-a > preparation of Compound 19-a

By the following synthetic example<5-a>The preparation was carried out in the same manner as in (1) to obtain compound 19-a except that N was used ²,N⁶-bis (4-tert-butylphenyl) naphthalene-d₆-2, 6-diamine and 4-tert-butylaniline instead of 1, 3-dibromo-5-chlorobenzene and 4-tert-butylbenzene-2, 3,5,6-d_-4-an amine. (yield 86%, MS [ M + H ]]⁺＝429)

<19-b > preparation of Compound 19-b

By the following synthetic example<5-a>The preparation was carried out in the same manner as in the above except that the compound 19-a and 1-bromo-3, 5-dichlorobenzene were used in place of 1, 3-dibromo-5-chlorobenzene and 4-tert-butylbenzene-2, 3,5,6-d to obtain the compound 19-b_-4-an amine. (yield 79%, MS [ M + H ]]⁺＝715)

<19-c > preparation of Compound 19-c

By the following synthetic example<5-a>The production was carried out in the same manner as in (1) except that the compound 19-b and N- (4-tert-butylphenyl) benzofuran-d were used_-52-amines instead of 1, 3-dibromo-5-chlorobenzene and 4-tert-butylbenzene-2, 3,5,6-d_-4-an amine. (yield 85%, MS [ M + H ]]⁺＝1185)

<19-d > preparation of Compound 19-d

After compound 19-c was dissolved in 1, 2-dichlorobenzene (0.1M) and boron triiodide (4 equivalents) was added thereto in a three-necked flask, the resulting mixture was stirred at 160 ℃ for 5 hours under an argon atmosphere. The reaction product was cooled to 0 ℃ and charged theretoN, N-diisopropylethylamine (40 eq) was added and the resulting mixture was stirred for 1 hour. Using toluene and H₂The O was extracted in a separatory funnel. Extracting with MgSO 2 ₄Dried and concentrated, and the sample was purified by silica gel column chromatography to obtain compound 19-d. (yield 12%, MS [ M + H ]]⁺＝1197)

<19-e > preparation of Compound 19

After compound 19-d (1 equivalent) and 9, 9-dimethyl-9, 10-dihydroacridine (2.2 equivalents) were dissolved in toluene (0.3M) in a three-necked flask and sodium tert-butoxide (3 equivalents) and bis (tri-tert-butylphosphine) palladium (0) (0.015 equivalent) were added thereto, the resulting mixture was stirred under reflux conditions for 6 hours under an argon atmosphere. When the reaction was complete, the flask was cooled to room temperature, and H was added thereto₂O, and the reaction solution was transferred to a separatory funnel for extraction. Extracting with MgSO 2₄Dried and concentrated, and the sample was subjected to sublimation purification with silica gel column chromatography to obtain compound 19. (yield 57%, MS [ M + H ]]⁺＝1543)

Synthesis example 20 Synthesis of Compound 20

<20-a > preparation of Compound 20-a

To prepare examples<1-a>In the same manner as in (1-bromo-3-chloro-5- (ethyl-d)₅) Benzene and N- (4-tert-butyl-2- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) phenyl) -9, 9-dimethyl-9H-fluoren-3-amine to give compound 20-a. (yield 84%, MS [ M + H ]]⁺＝671)

<20-b > preparation of Compound 20-b

To prepare examples<1-a>In the same manner as in (1) from the compound 20-a and N- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) dibenzo [ b, d ]Furan-3-amine to give compound 20-b. (yield 84%, MS [ M + H ]]⁺＝1004)

<20-c > preparation of Compound 20

To prepare examples<2-d>Compound 20 was obtained from Compound 20-b in the same manner as in (1). (yield 15%, MS [ M + H ]]⁺＝1012)

Synthesis example 21 Synthesis of Compound 21

<21-a > preparation of Compound 21-a

To prepare examples<1-a>In the same manner as in (1-bromo-3-chloro-5- (tert-butyl-d)₉) Benzene and 4a,9 a-dimethyl-2, 3,4,4a,9,9 a-hexahydro-1H-carbazole-5, 6,7-d₃Compound 21-a is obtained. (yield 84%, MS [ M + H ]]⁺＝380)

<21-b > preparation of Compound 21-b

To prepare examples<1-a>In the same manner as in (1) from compound 21-a and N- (4-tert-butylphenyl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphtho [2,3-b ]]Thiophene-3-amine to give compound 21-b. (yield 77%, MS [ M + H ]]⁺＝735)

<21-c > preparation of Compound 21

To prepare examples<2-d>Compound 21 was obtained from Compound 21-b in the same manner as in (1). (yield 20%, MS [ M + H ]]⁺＝743)

Synthesis example 22 Synthesis of Compound 22

<22-a > preparation of Compound 22-a

To prepare examples<5-a>In the same manner as in (1) and (4) are prepared from 2, 6-dibromonaphthalene-1, 3, 5,7,8-d₆And N- (4-tert-butylphenyl) -3-chloro-5- (tert-butyl-d₉) Aniline yields compound 22-a. (yield 72%, MS [ M + H ]]⁺＝779)

<22-b > preparation of Compound 22-b

To prepare examples<5-a>In the same manner as in (1) from compound 22-a and N- (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) benzo [ b ]Thiophene-d₅2-amine to give compound 22-b. (yield 59%, MS [ M + H ]]⁺＝1387)

<22-c > preparation of Compound 22

Examples of use and Synthesis<19-d>After the same procedure as in (1), compound 22 was obtained by purification from compound 22-b by sublimation. (yield 6%, MS [ M + H ]]⁺＝1399)

Experimental example 2 production of organic light emitting device

Example 1

Thinly coated with a thickness ofThe glass substrate of Indium Tin Oxide (ITO) of (1) is put in distilled water in which a detergent is dissolved, and subjected to super-treatmentAnd (4) sonic washing. In this case, a product manufactured by Fischer co. was used as a cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeatedly performed twice for 10 minutes using distilled water. After completion of the washing with distilled water, ultrasonic washing was performed by using solvents of isopropyl alcohol, acetone and methanol, and the resultant was dried and then transferred to a plasma washing machine. Further, the substrate was cleaned for 5 minutes by using oxygen plasma and then conveyed to a vacuum deposition machine.

The following HI-A and LG-101 were thermally vacuum deposited on the ITO transparent electrodes prepared as described to haveAndthereby forming a hole injection layer. Vacuum depositing the following HT-A on the hole injection layer Thereby forming a hole transport layer. Vacuum depositing the following HT-B on the hole transport layerThereby forming an electron blocking layer. Subsequently, 4 parts by weight of compound 1 of synthesis example 1 as a blue light emitting dopant based on 100 parts by weight of the light emitting layer was used on the electron blocking layer, and the following BH-a as a host was vacuum-deposited to have a structure havingThereby forming a light emitting layer. Then, the following compound ET-A as a first electron transport layer was vacuum-deposited on the light emitting layer to haveThen, the following ET-BAnd LiQ is vacuum deposited at a weight ratio of 1:1 to form a film having a thickness ofThe second electron transport layer of (1). Vacuum depositing LiQ on the second electron transport layer to haveThereby forming an electron injection layer. Depositing aluminum and silver on the electron injection layer at a weight ratio of 10:1 toAnd depositing aluminum thereon to haveThereby forming a negative electrode.

In the foregoing process, the deposition rate of the organic material is maintained atToMaintaining the deposition rate of aluminum of the negative electrode atThe degree of vacuum during deposition was maintained at 1X 10^-7Hold in the palm to 5 x 10^-8And supporting to thereby manufacture an organic light emitting device.

Examples 2 to 22 and comparative examples 1 to 3

Organic light emitting devices of examples 2 to 22 and comparative examples 1 to 3 were manufactured in the same manner as in example 1, except that compounds described in the following table 5 were respectively used as dopants of the light emitting layer instead of compound 1 in example 1.

Measurement when 10mA/cm was applied to the organic light emitting devices in examples 1 to 22 and comparative examples 1 to 3²Voltage and efficiency at a current density of 20mA/cm and when applied to the device²The current density (T95), and the results are shown in Table 1 below. In this case, LT95 means when 20mA/cm²The initial luminance at the current density of (1) is set to 100% and the ratio is shown based on comparative example 1 (100%) based on the time taken for the luminance to decrease to 95%.

[ Table 1]

In table 1, it can be seen that examples 1 to 22 including chemical formula 1 (i.e., including a boron compound including a heterocycle including O or S and including deuterium) according to one exemplary embodiment of the present specification in an organic light emitting material have better efficiency and exhibit a long lifespan effect, as compared to comparative examples 1 and 2 including boron compounds not including a heterocycle including O or S; examples 1 to 22 exhibited longer life effects than comparative example 3, which contained a heterocyclic boron compound containing no deuterium. These long-life effects are shown to be maximized by the carbon-deuterium bond of the heterocyclic compound containing O or S at the central core of chemical formula 1 of the present specification. In addition, the boron compound of chemical formula 1 having a heterocycle including O or S exhibits a characteristic of having lower triplet energy than the boron compound in the related art. Unlike a singlet state that rapidly returns to a ground state through a luminescence process, the triplet state slowly returns to the ground state while dissipating energy by heat or vibration energy, so that there arises a problem that boron compounds in the related art deteriorate through intramolecular or intermolecular interaction in a state having high triplet state energy. In addition, a process in which the compound is decomposed by light or current is performed while a carbon-hydrogen bond, which is a weak bond in the molecule, is dissociated to form a radical and an ion, but the compound of chemical formula 1 can effectively prevent the decomposition of the compound by including a stronger carbon-deuterium bond.

150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：有机化合物及包含其的有机电致发光元件

Compound and organic light emitting device including the same

相关技术

网友询问留言