阅读说明：本技术 化合物及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 2020-09-10 设计创作，主要内容包括：本说明书提供由化学式1表示的化合物及包含其的有机发光器件。(The present specification provides a compound represented by 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 organic solvents,

a1 and A2 are the same as or different from each other and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,

x1 and X2, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group, or a group selected from the group consisting of-CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO₂-, -SiRfRg-or-BRh-are directly linked,

ra to Rh, which are the same as or different from each other, are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

r1 to R5 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfenoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring,

y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, or represented by the following chemical formula 2,

chemical formula 2

In the chemical formula 2,

b1 and B2, which are the same as or different from each other, are each independently a substituted or unsubstituted aliphatic hydrocarbon ring or a substituted or unsubstituted aromatic hydrocarbon ring,

r6 and R7 are the same as or different from each other and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

r1 and r2, which are the same as or different from each other, are each independently an integer of 1 to 3,

r3 and r5 to r7, which are the same or different from each other, are each independently an integer of 1 to 11,

r4 is an integer of 1 or 2,

n is an integer of 1 or 2,

r4+ n is an integer of 2 or 3,

when r1 to r7 and n are each 2 or more, the substituents in the parentheses are the same as or different from each other,

when Y is an alkyl group of 1 to 3 carbon atoms substituted with deuterium, at least one of X1, X2, and R1 to R5 is an alkyl group of 1 to 3 carbon atoms substituted with deuterium,

when Y is represented by the above chemical formula 2, at least one of X1, X2, and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

represents the binding site of chemical formula 1.

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

chemical formula 1-1

Chemical formula 1-2

In the chemical formulas 1-1 and 1-2,

r1 to R7, A1, A2, B1, B2, X1, X2 and R1 to R7 are the same as defined in said chemical formula 1,

z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

m is an integer of 1 or 2, and when m is 2, Z are the same or different from each other,

r4+ m is an integer of 2 or 3.

3. The compound of claim 1, wherein said A1 and a2, equal to or different from each other, are each independently represented by any one of the following formulae a100 to a 103:

in the chemical formulae a100 to a103,

g1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combines with each other with adjacent groups to form a substituted or unsubstituted ring,

x11 is O, S or CR101R102,

r101 and R102, which may be the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

g1 is an integer from 0 to 5, g1 'is an integer from 0 to 11, g1 "is an integer from 0 to 7, g 1'" is an integer from 0 to 11,

a1 is an integer of 1 to 2,

when G1, G1', G1' and G1' are each 2 or more, 2 or more G1 s may be the same as or different from each other,

represents the binding site of chemical formula 1.

4. The compound of claim 1, wherein when the R1 or R2 and an adjacent group are combined with each other to form a substituted or unsubstituted ring, the ring is represented by any one of the following chemical formulae C1 to C3:

in the chemical formulae C1 to C3,

x21, X22 and X31, equal to or different from each other, are each independently O, S, CP11P12 or NP13,

p1 and P11 to P13, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring,

b1 is an integer of 1 to 3,

p1 is an integer of 0 to 10, p2 and p3 are each an integer of 0 to 4,

when P1 to P3 are each 2 or more, 2 or more P1 s may be the same as or different from each other,

indicates where the formed rings are fused.

5. The compound according to claim 1, wherein the chemical formula 2 is represented by any one of the following chemical formulae 201 to 203:

in the chemical formulae 201 to 203,

g6 and G7, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring,

g16 and G17, which are identical to or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

g6 and g7 are each integers from 1 to 5, g6 'and g7' are integers from 1 to 4, g7 "is an integer from 1 to 8,

when G6, G7, G6', G7' and G7' are each 2 or more, each of 2 or more G6 and G7 is the same as or different from each other,

represents the binding site of chemical formula 1.

6. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-3 to 1-7:

chemical formulas 1 to 3

Chemical formulas 1 to 4

Chemical formulas 1 to 5

Chemical formulas 1 to 6

Chemical formulas 1 to 7

In the chemical formulas 1-3 to 1-7,

r1 to R7, X1, X2 and R1 to R7 are the same as defined in said chemical formula 1,

z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

m is an integer of 1 or 2, and when m is 2, Z are the same or different from each other.

7. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formulae 1 to 8:

chemical formulas 1 to 8

In the chemical formulae 1 to 8,

a1, A2, R1 to R5, R1 to R5, Y and n are as defined in chemical formula 1,

x3 is CRaRb, NRc, O, PRd, S, PORe, SO₂SiRfRg or BRh,

ra to Rh are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

8. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formulae 1-9 or 1-10:

chemical formulas 1 to 9

Chemical formulas 1 to 10

In the chemical formulas 1 to 9 and 1 to 10,

x1, X2, A1, A2, R1, R3 to R5, R1, R3 to R5, Y and n are as defined in chemical formula 1,

a3 and A4 are the same as or different from each other and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,

r21 and R22 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring,

r21 and r22 are each an integer of 1 to 9,

when R21 and R22 are each 2 or more, 2 or more of R21 and R22 are each the same as or different from each other.

9. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formulae 1-11 or 1-12:

chemical formulas 1 to 11

Chemical formulas 1 to 12

In the chemical formulas 1 to 11 and 1 to 12,

x1, X2, R1 to R5, R1, R3, R4, A1, Y and n are as defined in said chemical formula 1,

x101 is a direct bond or-BR 103-,

r103, G101 and G102, which may be the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

r2' is 1 or 2,

r5' is an integer from 1 to 4,

r5' is an integer from 1 to 8,

when R2', R5' and R5 "are each 2 or more, 2 or more of R2 and R5 are each the same as or different from each other.

10. The compound of claim 1, wherein said Y is-CD₃、-C₂D₅、CH₂CD₃、CD(CD₃)₂Or CH (CD)₃)₂。

11. The compound according to claim 1, wherein when Y is represented by an alkyl group of carbon number 1 to 3 substituted with deuterium, at least 2 of X1, X2, and R1 to R5 are alkyl groups of carbon number 1 to 3 substituted with deuterium.

12. The compound according to claim 1, wherein when Y is represented by the chemical formula 2, at least 2 of X1, X2, and R1 to R7 are alkyl groups having 1 to 3 carbon atoms substituted with deuterium.

13. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:

14. an organic light emitting device, comprising: a first electrode; a second electrode; and 1 or more organic layers disposed between the first electrode and the second electrode, 1 or more of the organic layers comprising the compound of any one of claims 1 to 13.

15. The organic light emitting device of claim 14, wherein the organic layer comprises a light emitting layer comprising the compound.

16. The organic light emitting device of claim 14, wherein the organic layer comprises a light emitting layer comprising a dopant comprising the compound.

17. The organic light emitting device according to claim 16, wherein 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, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,

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

r20 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

r20 is an integer of 0 to 8, and when R20 is 2 or more, R20 may be the same as or different from each other.

18. The organic light emitting device of claim 16, wherein the light emitting layer further comprises a host compound having at least one hydrogen substituted with deuterium.

19. The organic light emitting device according to claim 14, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound.

20. The organic light emitting device according to claim 14, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises the compound.

Technical Field

The present application claims priority of korean patent application No. 10-2019-0112000, filed by the korean patent office at 9/10 in 2019, the entire contents of which are incorporated herein.

The present specification relates to a compound including an alkyl group substituted with deuterium and an organic light emitting device including the same.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.

There is a continuing demand for the development of new materials for organic light emitting devices as described above.

Documents of the prior art

(patent document 1) Chinese patent publication 108586441

Disclosure of Invention

Technical subject

Provided in the present specification are a compound including an alkyl group substituted with deuterium and an organic light emitting device including the same.

Means for solving the problems

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

[ chemical formula 1]

In the above-described chemical formula 1,

a1 and A2 are the same as or different from each other and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,

x1 and X2, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group, or a group selected from the group consisting of-CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO₂-, -SiRfRg-or-BRh-are directly linked,

ra to Rh, which are the same as or different from each other, are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

r1 to R5, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted alkylsulfoxy groupSubstituted or unsubstituted arylsulfenoxy Substituted or unsubstituted alkylthioSubstituted or unsubstituted arylthio Substituted or unsubstituted alkylsulfonylSubstituted or unsubstituted arylsulfonylA substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, or represented by the following chemical formula 2,

[ chemical formula 2]

In the above-described chemical formula 2,

b1 and B2, which are the same as or different from each other, are each independently a substituted or unsubstituted aliphatic hydrocarbon ring or a substituted or unsubstituted aromatic hydrocarbon ring,

r6 and R7 are the same as or different from each other and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

r1 and r2, which are the same as or different from each other, are each independently an integer of 1 to 3,

r3 and r5 to r7, which are the same or different from each other, are each independently an integer of 1 to 11,

r4 is an integer of 1 or 2,

n is an integer of 1 or 2,

r4+ n is an integer of 2 or 3,

when r1 to r7 and n are each 2 or more, the substituents in the parentheses are the same as or different from each other,

when Y is an alkyl group of 1 to 3 carbon atoms substituted with deuterium, at least one of X1, X2, and R1 to R5 is an alkyl group of 1 to 3 carbon atoms substituted with deuterium,

when Y is represented by the above chemical formula 2, at least one of X1, X2, and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

represents the binding site of chemical formula 1.

In addition, according to an embodiment of the present specification, there is provided an organic light emitting device including: a first electrode; a second electrode; and 1 or more organic layers disposed between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound represented by chemical formula 1.

Effects of the invention

The compound described in this specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment may achieve an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics in an organic light emitting device. In particular, the compound described in the present specification can be used as a material for hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection. In addition, compared with the existing organic light emitting device, the organic light emitting device has the effects of low driving voltage, high efficiency or long service life.

In addition, chemical formula 1 of the present application has an effect of improving conjugation and stability of the compound by including an alkyl group substituted with deuterium.

Drawings

Fig. 1 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 7, and a cathode 11 are sequentially stacked.

Fig. 2 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a first hole injection layer 3, a second hole injection layer 4, a hole transport layer 5, an electron blocking layer 6, a light emitting layer 7, a first electron transport layer 8, a second electron transport layer 9, an electron injection layer 10, and a cathode 11 are sequentially stacked.

[ description of symbols ]

1: substrate

2: anode

3: a first hole injection layer

4: second hole injection layer

5: hole transport layer

6: electron blocking layer

7: luminescent layer

8: a first electron transport layer

9: a second electron transport layer

10: electron injection layer

11: cathode electrode

Detailed Description

The present specification will be described in more detail below.

Conventional boron compounds have a half-width of about 23nm to 30nm and a basic core structure wavelength of about 453nm, but have a limit of a reduction in lifetime due to relatively low stability of the compounds compared to amine compounds. Therefore, a method of securing a long life by improving the stability of a substance while maintaining excellent optical characteristics by adjusting the substituent of the boron compound is required.

Provided are a compound including an alkyl group having 1 to 3 carbon atoms substituted with deuterium, and an organic light-emitting device including the same. The C-D bond of the compound of the present invention is stronger than the C-H bond, and thus the stability of the compound can be improved. Chemical decomposition in luminescent compounds is accompanied by relatively weak C (sp)³) When the-H bond is broken, the C-D bond, which is stronger than the C-H bond, is used, and the stability of the compound can be further improved.

At this time, if an alkyl group is used as a substituent which can donate electrons, the light emission characteristics can be effectively adjusted, but in a high energy state, the introduced alkyl group falls off, and decomposition of the compound is caused, thereby causing a problem in the life characteristics of the entire device. Methyl, ethyl, and propyl radicals, which are alkyl radicals having 1 to 3 carbon atoms, are unstable compared to tertiary carbon radicals (having 4 or more carbon atoms), and therefore have C (sp)³)-C(sp²) The decomposition process of the compound caused by the bond cleavage is relatively inhibited. Therefore, when the alkyl group of carbon atoms 1 to 3 substituted with deuterium is used, the stability of the blue device is ensured while the light emission characteristics can be effectively adjusted.

Further, with a smaller deuterium van der waals radius, the steric hindrance of methyl, ethyl, and propyl groups is smaller than that of the prior art, and thus conjugation can be improved.

In the context of the present specification,indicates the position of the binding to the chemical formula or compound.

In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.

In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.

In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted with a group selected from deuterium, a halogen group, a nitrile group (-CN), nitro, hydroxyl, alkyl, cycloalkyl, alkoxy, phosphinoxide, aryloxy, alkylsulfoxyAryl sulfo-oxoAlkylthio groupArylthio radicalsAlkyl sulfonyl radical Aryl sulfonyl radicalAlkyl sulfonyl radicalAryl sulfonyl radical1 or 2 of alkenyl, silyl, boryl, amino, aryl, or heterocyclic groupOr a substituent formed by connecting 2 or more substituents among the above-exemplified substituents, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boryl group, an amino group, an aryl group, or a heterocyclic group, or substituted with a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent.

In the present specification, the phrase "substituted or unsubstituted with A, B or C" means that the substituent is substituted or unsubstituted with 1 or more groups selected from the group consisting of substituents a to C or 2 or more groups selected from the above group. For example, substituted or unsubstituted by A, or substituted or unsubstituted by B, or substituted or unsubstituted by C, or substituted or unsubstituted by-A-B, or substituted or unsubstituted by-B-C, or substituted or unsubstituted by-C-A, or substituted or unsubstituted by-C-C, or may be substituted or unsubstituted by-A-B-C, or may be substituted or unsubstituted by-B-C-A, or may be substituted or unsubstituted by-A-A-B, or may be substituted or unsubstituted by-A- (C)₂The substituent is not limited to the above examples.

In this specification, N% substituted by deuterium means that N% of available hydrogens in the structure are substituted by deuterium. For example, when it is stated that 25% of the dibenzofurans are substituted with deuterium, it is meant that 2 of the 8 hydrogens of the dibenzofurans are substituted with deuterium.

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

Examples of the above-mentioned substituent are described below, but the substituent is not limited thereto.

In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).

In the present specification, the silyl group may be represented by-SiY_aY_bY_cThe above-mentioned chemical formula is Y_a、Y_bAnd Y_cMay each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In this specification, the boron group may be represented BY-BY_dY_eThe above-mentioned chemical formula is Y_dAnd Y_eMay each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, and n-octyl.

In the present specification, the above description of the alkyl group can be applied to the arylalkyl group except for the aryl group.

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 the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc., but is not limited thereto.

The alkyl group, the alkoxy group and other substituents containing an alkyl moiety described in the present specification are all included in a linear or branched form.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, and the like.

In the present specification, the amino group is-NH₂The above-mentioned amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, a combination thereof, or the like. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms of the amine group is 1 to 20. According to one embodiment, the number of carbon atoms of the amine group is 1 to 10. Specific examples of the substituted amino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a 9, 9-dimethylfluorenylphenylamino group, a pyridylphenylamino group, a diphenylamino group, a phenylpyridinylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a dibenzofuranylphenylamino group, a 9-methylanthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a ditolylamino group, a phenyltolylamino group, and a diphenylamino group.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. With respect to the above aryl group, as a monocyclic ringThe aryl group may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a triphenyl group, a perylene group,Examples of the group include, but are not limited to, a fluorenyl group, a triphenylene group, and the like.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.

When the fluorenyl group is substituted, the compound may beIsospirofluorene group;(9, 9-dimethylfluorenyl group) andand substituted fluorenyl groups such as (9, 9-diphenylfluorenyl) and the like. But is not limited thereto.

In the present specification, the aryl group in the aryloxy group can be applied to the description about the aryl group described above.

In the present specification, the above description about the alkyl group can be applied to the alkyl group in the above alkylthio group and alkylsulfonyl group.

In the present specification, the aryl group in the above arylthio group and arylsulfonyl group can be applied to the description about the aryl group described above.

In the present specification, the above description about the alkyl group can be applied to the alkyl group in the above alkylsulfoxy group and alkylsulfonyl group.

In the present specification, the aryl group in the arylsulfonyl group and the arylsulfonyl group described above can be applied to the aryl group described above.

In the present specification, the heterocyclic group is a cyclic group containing 1 or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuryl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuryl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like.

In the present specification, the heteroaryl group is an aromatic group, and the above description of the heterocyclic group can be applied thereto.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a hydrocarbon ring or a heterocyclic ring.

The hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and may be selected from the cycloalkyl groups and the aryl groups described above, in addition to the 1-valent group.

In the present specification, the term "form a ring by bonding adjacent groups to each other" means that a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or a fused ring thereof is formed by bonding adjacent groups to each other. The above-mentioned hydrocarbon ring means a ring composed of only carbon atoms and hydrogen atoms. The heterocyclic ring means a ring containing 1 or more selected from N, O, P, S, Si and Se. In the present specification, the above-mentioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring and aromatic heterocyclic ring may be monocyclic or polycyclic.

In the present specification, an aliphatic hydrocarbon ring means a ring which is not an aromatic ring and is composed of only carbon atoms and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1, 4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, but are not limited thereto.

In the present specification, the aromatic hydrocarbon ring refers to an aromatic ring composed of only carbon atoms and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, perylene, and the like,Tetracene,Pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, etc., but is not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more heteroatoms. Examples of the aliphatic heterocyclic ring include ethylene oxide (oxirane), tetrahydrofuran, and 1, 4-bisAlkanes (1,4-dioxane), pyrrolidine, piperidine, morpholine (morpholine), oxepane AzacyclooctaneThiocyclooctaneAnd the like, but is not limited thereto.

In the present specification, an aromatic heterocyclic ring means an aromatic ring containing 1 or more heteroatoms. Examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, and the like,Oxazole, isoOxazole, thiazole, isothiazole, triazole, and the like,Oxadiazoles, thiadiazoles, dithiazoles, tetrazoles, pyrans, thiopyrans, diazines,Oxazine, thiazine, IIAlkene, triazine, tetrazine, isoquinoline, quinoline, benzoquinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazindene, indole, indolizine, benzothiazole, benzoquinoneOxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, thiopheneOxazines, indolocarbazoles, indenocarbazoles, and the like, but are not limited thereto.

Preferred embodiments of the present invention will be described in detail below. However, the embodiment of the present invention may be modified into various forms, and the scope of the present invention is not limited to the embodiments described below.

Preferred embodiments of the present invention will be described in detail below. However, the embodiment of the present invention may be modified into various forms, and the scope of the present invention is not limited to the embodiments described below.

The present specification provides a compound represented by the following chemical formula 1. When the compound represented by the following chemical formula 1 is used for an organic layer of an organic light emitting device, not only the efficiency of the organic light emitting device is improved, but also a low driving voltage is provided and excellent life characteristics are provided.

[ chemical formula 1]

In the above-described chemical formula 1,

a1 and A2 are the same as or different from each other and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,

x1 and X2, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group, or a group selected from the group consisting of-CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO₂-, -SiRfRg-or-BRh-are directly linked,

ra to Rh, which are the same as or different from each other, are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

r1 to R5 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfenoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring,

y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, or represented by the following chemical formula 2,

[ chemical formula 2]

In the above-described chemical formula 2,

b1 and B2, which are the same as or different from each other, are each independently a substituted or unsubstituted aliphatic hydrocarbon ring or a substituted or unsubstituted aromatic hydrocarbon ring,

r6 and R7 are the same as or different from each other and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

r1 and r2, which are the same as or different from each other, are each independently an integer of 1 to 3,

r3 and r5 to r7, which are the same or different from each other, are each independently an integer of 1 to 11,

r4 is an integer of 1 or 2,

n is an integer of 1 or 2,

r4+ n is an integer of 2 or 3,

when r1 to r7 and n are each 2 or more, the substituents in the parentheses are the same as or different from each other,

when Y is an alkyl group of 1 to 3 carbon atoms substituted with deuterium, at least one of X1, X2, and R1 to R5 is an alkyl group of 1 to 3 carbon atoms substituted with deuterium,

when Y is represented by the above chemical formula 2, at least one of X1, X2, and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

represents the binding site of chemical formula 1.

In one embodiment of the present specification, the half width of the compound represented by the above chemical formula 1 is 17nm to 35 nm.

In one embodiment of the present specification, the alkyl group having 1 to 3 carbon atoms substituted with deuterium may be substituted with-CDH₂、-CD₂H、-CD₃、-C₂D₅、-CH₂CD₃、-CD(CD₃)₂or-CH (CD)₃)₂And (4) showing.

According to an embodiment of the present description, the methyl group substituted with deuterium may be represented by-CD₃And (4) showing.

According to an embodiment of the present description, the ethyl group substituted with deuterium may be substituted with-C₂D₅(-CD₂CD₃) Or CH₂CD₃And (4) showing.

According to an embodiment of the present specification, the propyl group substituted with deuterium may be substituted with deuterium(-CD(CD₃)₂) Or(CH(CD₃)₂) And (4) showing.Indicating the binding site.

According to an embodiment of the present specification, a1 and a2 are the same as or different from each other, and each independently is a substituted or unsubstituted monocyclic to tetracyclic aliphatic hydrocarbon ring, a substituted or unsubstituted monocyclic to tetracyclic aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of a monocyclic to tetracyclic aliphatic hydrocarbon ring and a monocyclic to tetracyclic aromatic hydrocarbon ring.

According to one embodiment of the present specification, a1 and a2 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring, a substituted or unsubstituted monocyclic to tetracyclic aromatic hydrocarbon ring, a substituted or unsubstituted monocyclic to tricyclic aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of a monocyclic or bicyclic aliphatic hydrocarbon ring and a monocyclic or bicyclic aromatic hydrocarbon ring.

According to one embodiment of the present specification, a1 and a2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 30 carbon atoms, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to one embodiment of the present specification, a1 and a2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 20 carbon atoms, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an embodiment of the present specification, a1 and a2, which are the same as or different from each other, are each independently a benzene ring substituted or unsubstituted with a phenyl group or a naphthyl group, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted triphenylene ring, a substituted or unsubstituted cyclohexane ring, a substituted or unsubstituted benzene ring to which a substituted or unsubstituted cyclopentene or a substituted or unsubstituted cyclohexene is fused, or a substituted or unsubstituted dibenzofuran ring.

According to an embodiment of the present specification, A1 and a2 are the same as or different from each other, and each is independently represented by any one of the following chemical formulae a100 to a 103.

In the above chemical formulae a100 to a103,

g1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combines with each other with adjacent groups to form a substituted or unsubstituted ring,

x11 is O, S or CR101R102,

r101 and R102, which may be the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

g1 is an integer from 0 to 5, g1 'is an integer from 0 to 11, g1 "is an integer from 0 to 7, g 1'" is an integer from 0 to 11,

a1 is an integer of 1 to 2,

when G1, G1', G1' and G1' are each 2 or more, 2 or more G1 s may be the same as or different from each other,

represents the binding site of chemical formula 1.

According to one embodiment of the present specification, G1 is hydrogen, deuterium, or a substituted or unsubstituted alkyl group, or combines with adjacent groups to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, G1 is hydrogen, deuterium, or an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or is bonded to adjacent groups to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, or is directly bonded to R1 or R2 to form a carbazole ring, a hexahydrocarbazole ring, orAnd (4) a ring.

According to one embodiment of the present specification, G1 is hydrogen, deuterium, or an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, or is bonded to adjacent groups to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or is directly bonded to R1 or R2 to form a carbazole ring, a hexahydrocarbazole ring, orAnd (4) a ring.

According to one embodiment of the present specification, G1 is hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium, or is bonded to adjacent groups to form a benzene ring or a phenanthrene ring, or is directly bonded to R1 or R2 to form a carbazole ring, a hexahydrocarbazole ring, orAnd (4) a ring.

According to one embodiment of the present specification, G1 is hydrogen, deuterium, or an alkyl group of 1 to 4 carbon atoms substituted or unsubstituted with deuteriumOr combined with adjacent groups to form a benzene ring or a phenanthrene ring, or directly bonded with R1 or R2 to form a carbazole ring, a hexahydrocarbazole ring, orAnd (4) a ring.

According to one embodiment of the present specification, G1 is hydrogen, deuterium, or methyl substituted or unsubstituted with deuterium, ethyl substituted or unsubstituted with deuterium, propyl substituted or unsubstituted with deuterium, or butyl substituted or unsubstituted with deuterium, or combines with adjacent groups to form a phenanthrene ring, or directly bonds with R1 or R2 to form a carbazole ring, a hexahydrocarbazole ring, orAnd (4) a ring.

According to one embodiment of the present specification, G1 is hydrogen, deuterium, or methyl substituted or unsubstituted with deuterium, ethyl substituted or unsubstituted with deuterium, isopropyl substituted or unsubstituted with deuterium, or tert-butyl substituted or unsubstituted with deuterium, or combines with adjacent groups to form a phenanthrene ring, or directly bonds with R1 or R2 to form a carbazole ring, hexahydrocarbazole ring, orAnd (4) a ring.

According to one embodiment of the present specification, X11 is O or CR101R 102.

According to an embodiment of the present specification, R101 and R102, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

According to an embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present specification, R101 and R102, which are the same or different from each other, are each independently an alkyl group substituted or unsubstituted with deuterium, or an aryl group substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, R101 and R102, which are the same or different from each other, are each independently a methyl group substituted or unsubstituted with deuterium, or a phenyl group.

According to an embodiment of the present description, R101 and R102 are methyl substituted or unsubstituted with deuterium.

According to an embodiment of the present description, R101 and R102 are methyl or CD₃。

According to an embodiment of the present description, a1 is 1 or 2.

According to an embodiment of the present description, g1 is 1 to 4.

According to an embodiment of the present description, g1' is 1 to 4.

According to an embodiment of the present description, g1 "is 1 to 4.

According to an embodiment of the present description, g1 "' is 1 to 4.

According to an embodiment of the present specification, a1 and a2 are the same as or different from each other, and each is independently represented by any one of the following structures.

In the above-described structure, the first and second electrodes,

r101 to R103, G101 and G102, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

represents a binding site to chemical formula 1,

indicates the position of binding to R1 or R2.

According to an embodiment of the present description, R103 is substituted or unsubstituted aryl.

According to an embodiment of the present specification, R103 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, R103 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present description, R103 is deuterium, methyl or CD₃Substituted or unsubstituted aryl.

According to an embodiment of the present description, R103 is deuterium, methyl or CD₃Substituted or unsubstituted phenyl.

According to one embodiment of the present specification, R103 is CD₃Substituted or unsubstituted phenyl.

According to an embodiment of the present specification, G101 and G102, which are the same or different from each other, are each independently a substituted or unsubstituted alkyl group.

According to an embodiment of the present specification, G101 and G102 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, G101 and G102 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present specification, G101 and G102, which are the same or different from each other, are each independently an alkyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present description, G101 and G102 are methyl or CD₃。

According to an embodiment of the present specification, a1 and a2 are the same or different from each other, and each independently represents a benzene ring, a triphenylene ring, a fluorene ring, a cyclohexane ring, a dibenzofuran ring, a benzene ring fused with cyclopentene, or a benzene ring fused with cyclohexane, and the above substituents are substituted with G1 or unsubstituted.

According to an embodiment of the present specification, a1 and a2 are the same as or different from each other, and each is independently represented by any one of the following structures.

The above groups are substituted or unsubstituted with deuterium or an alkyl group having 1 to 3 carbon atoms.

According to one embodiment of the present specification, X1 and X2, equal to or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group, or a group selected from the group consisting of-CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO-, -Y-C-, -O-, -C-O-, -PRd-, -S-, -PORe-, -Y-C-O-and-C-O-are used₂-, -SiRfRg-or-BRh-.

According to one embodiment of the present specification, X1 and X2, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a compound represented by the formula-CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO₂-, -SiRfRg-or-BRh-.

According to one embodiment of the present specification, X1 and X2, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a compound represented by the formula-CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO₂-, -SiRfRg-or-BRh-.

According to one embodiment of the present specification, X1 and X2, which are the same or different from each other, are each independently hydrogen, deuterium, or an alkyl group substituted or unsubstituted with deuterium, or are substituted or unsubstituted with-CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO₂-, -SiRfRg-or-BRh-.

According to an embodiment of the present specification, X1 and X2, which are the same or different from each other, are each independently hydrogen, deuterium, or an alkyl group of 1 to 3 carbon atoms substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, X1 and X2, which are the same or different from each other, are each independently hydrogen, deuterium, a methyl group substituted or unsubstituted with deuterium, an ethyl group substituted or unsubstituted with deuterium, or a propyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, X1 and X2, which are the same or different from each other, are each independently hydrogen, deuterium, a methyl group substituted or unsubstituted with deuterium, an ethyl group substituted or unsubstituted with deuterium, or an isopropyl group substituted or unsubstituted with deuterium.

According to one embodiment of the present specification, X1 and X2 are represented by-CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO₂-, -SiRfRg-or-BRh-.

According to one embodiment of the present specification, X1 and X2 are represented by-CRaRb-, -NRc-, -O-, -S-, -PORe-, -SO₂-, -SiRfRg-or-BRh-.

According to an embodiment of the present specification, Ra to Rh are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring.

According to an embodiment of the present specification, Ra to Rh are the same as or different from each other, and each independently is an alkyl group substituted or unsubstituted with deuterium, an alkenyl group substituted or unsubstituted with deuterium, an alkynyl group substituted or unsubstituted with deuterium, an arylalkyl group substituted or unsubstituted with deuterium, an aryl group substituted or unsubstituted with deuterium, or a heterocyclic group substituted or unsubstituted with deuterium, or adjacent groups are combined with each other to form a ring substituted or unsubstituted with deuterium or deuterium-substituted methyl group.

According to an embodiment of the present specification, Ra to Rh are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 12 to 30 carbon atoms.

According to an embodiment of the present specification, Ra to Rh are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 20 carbon atoms or a substituted or unsubstituted heterocyclic ring having 12 to 20 carbon atoms.

According to an embodiment of the present specification, Ra to Rh are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 20 carbon atoms or a substituted or unsubstituted heterocyclic ring having 12 to 20 carbon atoms.

According to an embodiment of the present disclosure, Ra to Rh are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

According to an embodiment of the present specification, Ra to Rh are the same as or different from each other, and each independently is an alkyl group substituted or unsubstituted by deuterium, an aryl group substituted or unsubstituted by deuterium, or a heterocyclic group substituted or unsubstituted by deuterium, or adjacent groups are bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted by deuterium or a substituted or unsubstituted heterocyclic ring.

According to an embodiment of the present specification, Ra to Rh, equal to or different from each other, are each independently deuterated or CD₃Substituted or unsubstituted alkyl, deuterium or CD₃Substituted or unsubstituted aryl, or by deuterium or CD₃Substituted or unsubstituted heterocyclic group, or adjacent groups combined with each other to form deuterium or CD₃Substituted or unsubstituted aromatic hydrocarbon rings or substituted or unsubstituted aromatic hydrocarbon rings substituted by deuterium orCD₃Substituted or unsubstituted heterocycle.

According to an embodiment of the present disclosure, Ra to Rh are the same or different from each other, and each independently is a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted structure described below.

In the following construction, it is preferable that,indicating the position of the loop.

According to an embodiment of the present specification, Ra to Rh, which are the same or different from each other, are each independently a methyl group substituted or unsubstituted with deuterium; or a phenyl group which is unsubstituted or substituted with 1 or more groups or 2 or more groups linked together selected from deuterium, methyl and hexahydrocarbazolyl groups, or adjacent groups are bonded to each other to form a fluorene ring, or the following structure. The following structure is used for warp knitting CD₃Substituted or unsubstituted phenyl is substituted or unsubstituted,indicating the position of the loop.

According to an embodiment of the present specification, Ra to Rh are the same or different from each other, and each is independently CD₃Methyl, or via CD₃Or by CD₃Substituted or unsubstituted phenyl groups substituted with substituted hexahydrocarbazolyl groups, or adjacent groups are combined with each other to form a fluorene ring, or the following structure. The following structure is used for warp knitting CD₃Substituted or unsubstituted phenyl is substituted or unsubstituted,indicating the position of the loop.

According to an embodiment of the present specification, R1 to R5 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring.

According to an embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted arylalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms, Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylsulfonyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted arylalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having, Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

According to an embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 10 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 14 carbon atoms, a substituted or unsubstituted alkylsulfonyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 14 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted arylalkyl group having 1 to 14 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, or a substituted or unsubstituted heteroaryl group having 6 to 14 carbon atoms, Or a substituted or unsubstituted heterocyclic group having 2 to 14 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 14 carbon atoms.

According to an embodiment of the present description, R1 to R5, equal to or different from each other, are each independently hydrogen; deuterium; an alkyl group which is unsubstituted or substituted with 1 or more groups selected from deuterium, a halogen group, an alkyl group, an aryl group and a heterocyclic group, or 2 or more groups connected to each other; an alkoxy group which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group; aryloxy substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group; alkylthio which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, a halogen group, an alkyl group, an aryl group and a heterocyclic group; arylthio substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group; alkylsulfonyl substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group; arylsulfonyl substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group; an amino group which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, a halogen group, an alkyl group, an aryl group and a heterocyclic group; a silyl group which is unsubstituted or substituted with 1 or more groups selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group in which 2 or more groups are bonded to each other; a boron group which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group; an arylalkyl group substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group; cycloalkyl which is unsubstituted or substituted with 1 or more groups selected from deuterium, a halogen group, an alkyl group, an aryl group and a heterocyclic group, or 2 or more groups connected to each other; aryl substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group; or a heterocyclic group which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium, a halogen group, an alkyl group, an aryl group and a heterocyclic group, or adjacent groups are bonded to each other to form a ring which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium, a halogen group, an alkyl group, an aryl group and a heterocyclic group.

According to an embodiment of the present specification, R1 and R2 are the same as or different from each other and each independently is hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted methylthio group, a substituted or unsubstituted phenylthio group, a substituted or unsubstituted methylsulfonyl group, a substituted or unsubstituted tert-butylsulfonyl group, a substituted or unsubstituted phenylsulfonyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted phenylpropyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazolyl group, Substituted or unsubstituted pyridyl, or substituted or unsubstituted hexahydrocarbazolyl, or bonded directly to R3 or R5, or bound through B substituted with substituted or unsubstituted phenyl, or bound to each other with adjacent groups to form a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted cyclopentene ring, a substituted or unsubstituted cyclohexene ring, a substituted or unsubstituted cycloheptene ring, a substituted or unsubstituted tetralin ring, a substituted or unsubstituted dihydrobenzodiazepine ringAlkene (dihydrobenzol [ b ]]dioxine) ring, a substituted or unsubstituted tetrahydroethyl bridged naphthalene (tetrahydronaphthalene) ring, a substituted or unsubstituted bicycloheptene ring, a substituted or unsubstituted bicyclooctene ring, or a substituted or unsubstituted hexahydrocarbazolyl group. The above groups are substituted or unsubstituted with 1 or more groups or 2 or more groups bonded selected from deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms.

In accordance with one embodiment of the present description,r1 and R2 are selected from deuterium, -F, methyl, CD₃And 1 or more groups or 2 or more groups in the isopropyl group, the tert-butyl group and the phenyl group are substituted or unsubstituted.

According to an embodiment of the present description, R1 and R2, equal to or different from each other, are each independently hydrogen; deuterium; methyl substituted or unsubstituted with deuterium or-F; ethyl substituted or unsubstituted with deuterium or-F; a propyl group which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, -F, and phenyl; butyl substituted or unsubstituted with deuterium or-F; pentyl substituted or unsubstituted with deuterium or-F; methoxy substituted or unsubstituted with deuterium or-F; methylthio substituted or unsubstituted with deuterium or-F; by deuterium, methyl or CD₃Substituted or unsubstituted thiophenyl; methylsulfonyl substituted or unsubstituted with deuterium; tert-butylsulfonyl substituted or unsubstituted with deuterium; by deuterium, methyl or CD₃Substituted or unsubstituted phenylsulfonyl; by deuterium, -F, methyl, or by CD₃Substituted or unsubstituted phenyl, or CD₃A substituted amino group; trimethylsilyl substituted or unsubstituted with deuterium; by deuterium, methyl or CD₃Substituted or unsubstituted triphenylsilyl; by deuterium, methyl, or by CD₃Substituted or unsubstituted phenyl substituted or unsubstituted boryl; by deuterium, methyl or CD₃Substituted or unsubstituted cyclopentyl; by deuterium, methyl or CD₃A substituted or unsubstituted cyclohexyl group; by deuterium, methyl or CD₃Substituted or unsubstituted phenylpropyl; by deuterium, -F, methyl or CD₃Substituted or unsubstituted phenyl; is selected from deuterium, methyl, CD₃A substituted or unsubstituted carbazolyl group formed by connecting more than 1 group or more than 2 groups in the tert-butyl and phenyl; quilt CD₃Substituted or unsubstituted pyridyl; or by methyl, CD₃Or tert-butyl substituted or unsubstituted hexahydrocarbazolyl, or bonded directly to R3 or R5, or through a CD-bonded linker₃Substituted or unsubstituted phenyl-substituted B, or adjacent groups to each other to form deuterium, methyl or CD₃A substituted or unsubstituted phenanthrene ring; by methyl or CD₃Substituted or notSubstituted indene rings; by deuterium, methyl, CD₃Or a tert-butyl substituted or unsubstituted benzofuran ring; by deuterium, methyl or CD₃A substituted or unsubstituted benzothiophene ring; is selected from CD₃And a substituted or unsubstituted indole ring having 1 or more groups or 2 or more groups bonded to the phenyl group; carbazole rings substituted or unsubstituted with 1 or more groups or 2 or more groups selected from deuterium, methyl, tert-butyl, and phenyl; by deuterium, methyl or CD₃A substituted or unsubstituted cyclopentene ring; by deuterium, methyl or CD₃A substituted or unsubstituted cyclohexene ring; by deuterium, methyl or CD₃A substituted or unsubstituted cycloheptene ring; by deuterium, methyl or CD₃A substituted or unsubstituted tetralin ring; by deuterium, methyl or CD₃Substituted or unsubstituted dihydrobenzodiAlkene (dihydrobenzol [ b ]]dioxine) ring; by deuterium, methyl or CD₃A substituted or unsubstituted tetrahydroethyl bridged naphthalene (tetrahydrohanonapthalene) ring; by deuterium, methyl or CD₃A substituted or unsubstituted bicycloheptene ring; by deuterium, methyl or CD₃A substituted or unsubstituted bicyclooctene ring; or by deuterium, methyl, CD₃And tert-butyl substituted or unsubstituted hexahydrocarbazolyl.

According to an embodiment of the present description, R1 and R2, equal to or different from each other, are each independently hydrogen; deuterium; methyl substituted or unsubstituted with deuterium or-F; ethyl substituted or unsubstituted with deuterium; isopropyl substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium and phenyl; a tertiary butyl group; a tertiary amyl group; methoxy substituted or unsubstituted with deuterium or-F; methylthio substituted or unsubstituted with deuterium or-F; a phenylthio group; methylsulfonyl substituted or unsubstituted with deuterium; tert-butylsulfonyl substituted or unsubstituted with deuterium; a phenylsulfonyl group; by deuterium, -F, methyl, or by CD₃Substituted or unsubstituted phenyl, or CD₃A substituted amino group; trimethylsilyl substituted or unsubstituted with deuterium; a triphenylsilyl group; a diphenylboron group;by deuterium or CD₃Substituted or unsubstituted cyclopentyl; by deuterium or CD₃A substituted or unsubstituted cyclohexyl group; phenylpropyl substituted or unsubstituted with deuterium; by deuterium, -F or CD₃Substituted or unsubstituted phenyl; is selected from deuterium, methyl, CD₃A substituted or unsubstituted carbazolyl group formed by connecting more than 1 group or more than 2 groups in the tert-butyl and phenyl; quilt CD₃Substituted or unsubstituted pyridyl; or by methyl, CD₃Or tert-butyl substituted or unsubstituted hexahydrocarbazolyl, or bonded directly to R3 or R5, or through a CD-bonded linker₃Substituted or unsubstituted phenyl-substituted B, or adjacent groups to each other to form a phenanthrene ring; by methyl or CD₃A substituted or unsubstituted indene ring; quilt CD₃Or a tert-butyl substituted or unsubstituted benzofuran ring; a benzothiophene ring substituted or unsubstituted with deuterium; is selected from CD₃And a substituted or unsubstituted indole ring having 1 or more groups or 2 or more groups bonded to the phenyl group; is selected from CD₃1 or more groups or 2 or more groups in the tert-butyl and phenyl groups are combined to form a substituted or unsubstituted carbazole ring; by deuterium, methyl or CD₃A substituted or unsubstituted cyclopentene ring; by deuterium, methyl or CD₃A substituted or unsubstituted cyclohexene ring; a cycloheptene ring substituted or unsubstituted with deuterium; by deuterium, methyl or CD₃A substituted or unsubstituted tetralin ring; dihydrobenzodi substituted or unsubstituted by deuteriumAlkene (dihydrobenzol [ b ]]dioxine) ring; a tetrahydroethylnaphthalene (tetrahydrohanonapthalene) ring; a bicycloheptene ring substituted or unsubstituted with methyl; a bicyclooctene ring substituted or unsubstituted with methyl; or hexahydrocarbazolyl substituted or unsubstituted with methyl or tert-butyl.

According to an embodiment of the present description, R1 and R2, equal to or different from each other, are each independently hydrogen; deuterium; methyl substituted or unsubstituted with deuterium or-F; ethyl substituted or unsubstituted with deuterium; by 1 or more groups selected from deuterium and phenyl or 2Isopropyl substituted or unsubstituted with more than one group connected; a tertiary butyl group; a tertiary amyl group; methoxy substituted or unsubstituted with deuterium or-F; by deuterium, -F, methyl, or by CD₃Substituted or unsubstituted phenyl, or CD₃A substituted amino group; trimethylsilyl substituted or unsubstituted with deuterium; or by deuterium, -F or CD₃Substituted or unsubstituted phenyl, or with adjacent groups bound to each other to form a CD-protected group₃Or a tert-butyl substituted or unsubstituted benzofuran ring; a benzothiophene ring substituted or unsubstituted with deuterium; by deuterium, methyl or CD₃A substituted or unsubstituted cyclohexene ring; a cycloheptene ring substituted or unsubstituted with deuterium; a tetrahydroethylnaphthalene (tetrahydrohanonapthalene) ring; or hexahydrocarbazolyl substituted or unsubstituted with methyl or tert-butyl.

According to an embodiment of the present specification, R3 and R5 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted phenylpropyl group, a substituted or unsubstituted adamantyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, or is bonded to R1 or R2 directly or through a substituted or unsubstituted B, or adjacent groups are bonded to each other to form a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted cyclopentene ring, a substituted or unsubstituted cyclohexene ring, a substituted or unsubstituted indole ring, a substituted or indole ring, a pyrimidine ring, a substituted or indole ring, a pharmaceutically acceptable salt thereof, or solvate thereof, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable carrier, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable carrier or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable carrier, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable carrier, or a pharmaceutically acceptable carrier, a pharmaceutically acceptable carrier, a pharmaceutically acceptable carrier, a, Or a substituted or unsubstituted benzofuran ring. The above groups are substituted or unsubstituted with 1 or more groups or 2 or more groups bonded selected from deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present description, R3 and R5 are chosen from deuterium, -F, methyl, CD₃And 1 or more groups or 2 or more groups in the isopropyl group, the tert-butyl group and the phenyl group are substituted or unsubstituted.

According to an embodiment of the present description, R3 and R5, equal to or different from each other, are each independently hydrogen; deuterium; methyl substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, -F, methyl and phenyl; an ethyl group which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, -F, methyl, and phenyl; a propyl group which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, -F, methyl, and phenyl; a butyl group which is substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, -F, methyl and phenyl; silyl substituted or unsubstituted with methyl or phenyl; by deuterium, methyl, CD₃Or a phenyl substituted or unsubstituted boron group; by deuterium, methyl or CD₃Substituted or unsubstituted phenylpropyl; by deuterium, methyl or CD₃Substituted or unsubstituted adamantyl; phenyl substituted or unsubstituted with 1 or more groups or 2 or more groups linked together selected from deuterium, -F, methyl, ethyl, propyl, and butyl; by deuterium, methyl or CD₃Substituted or unsubstituted naphthyl; by deuterium, methyl or CD₃Substituted or unsubstituted dibenzofuranyl; by deuterium, methyl or CD₃Substituted or unsubstituted pyridyl; or carbazolyl which is substituted or unsubstituted by 1 or more groups or 2 or more groups linked from deuterium, methyl and phenyl, or directly bonded to R1 or R2, or bonded to CD₃Substituted or unsubstituted phenyl substituted or unsubstituted B, or adjacent groups are bonded to each other to form deuterium, methyl or CD₃A substituted or unsubstituted phenanthrene ring; by deuterium, methyl or CD₃A substituted or unsubstituted indene ring; by deuterium, methyl or CD₃A substituted or unsubstituted cyclopentene ring; by deuterium, methyl or CD₃A substituted or unsubstituted cyclohexene ring; or by deuterium, methyl or CD₃A substituted or unsubstituted benzofuran ring.

According to an embodiment of the present description, R3 and R5, equal to or different from each other, are each independently hydrogen; deuterium; methyl substituted or unsubstituted with deuterium or-F; substituted or not by deuteriumA substituted ethyl group; isopropyl substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium and phenyl; tert-butyl substituted or unsubstituted with deuterium; a trimethylsilyl group; a diphenylboron group; phenylpropyl substituted or unsubstituted with deuterium; an adamantyl group; phenyl substituted or unsubstituted with deuterium, -F, methyl substituted or unsubstituted with deuterium, or isopropyl substituted or unsubstituted with deuterium; a naphthyl group; a dibenzofuranyl group; a pyridyl group; or deuterium, methyl substituted or unsubstituted by deuterium or by CD₃Substituted or unsubstituted carbazolyl substituted or unsubstituted with substituted or unsubstituted phenyl, either directly bonded to R1 or R2 or through a CD-bonded bridge₃Substituted or unsubstituted phenyl-substituted B, or adjacent groups are bonded to each other to form deuterium, methyl or CD₃A substituted or unsubstituted phenanthrene ring; by deuterium, methyl or CD₃A substituted or unsubstituted indene ring; by deuterium, methyl or CD₃A substituted or unsubstituted cyclopentene ring; by deuterium, methyl or CD₃A substituted or unsubstituted cyclohexene ring; or by deuterium, methyl or CD₃A substituted or unsubstituted benzofuran ring.

According to an embodiment of the present description, R3 and R5, equal to or different from each other, are each independently hydrogen; deuterium; methyl substituted or unsubstituted with deuterium; ethyl substituted or unsubstituted with deuterium; isopropyl substituted or unsubstituted with 1 or more groups or 2 or more groups linked from deuterium and phenyl; tert-butyl substituted or unsubstituted with deuterium; phenylpropyl substituted or unsubstituted with deuterium; or phenyl substituted or unsubstituted by deuterium, methyl substituted or unsubstituted by deuterium or isopropyl substituted or unsubstituted by deuterium, or directly bonded to R1 or R2, or by being bound by CD₃Substituted or unsubstituted phenyl-substituted B, or adjacent groups are bonded to each other to form deuterium, methyl or CD₃A substituted or unsubstituted indene ring; by deuterium, methyl or CD₃A substituted or unsubstituted cyclohexene ring; or by deuterium, methyl or CD₃A substituted or unsubstituted benzofuran ring.

According to an embodiment of the present description, adjacent R1 and R3 combine with each other to form a substituted or unsubstituted ring.

According to an embodiment of the present description, adjacent R1 and R3 combine with each other to form a substituted or unsubstituted carbazole ring, a substituted or unsubstituted hexahydrocarbazole ring, or join through B to form a substituted or unsubstituted carbazole ringAnd (4) a ring.

According to an embodiment of the present specification, adjacent R1 and R3 combine with each other to form a carbazole ring substituted with deuterium, or an alkyl group of 1 to 3 carbon atoms substituted with deuterium; a hexahydrocarbazole ring substituted or unsubstituted with deuterium or an alkyl group having 1 to 3 carbon atoms substituted with deuterium, or linked through B to form a structure containing a C-substituted amino group₃Substituted phenyl substituted or unsubstitutedAnd (4) a ring.

According to one embodiment of the present description, adjacent R1 and R3 combine with each other to form a CD-protected article₃A substituted or unsubstituted hexahydrocarbazole ring.

According to an embodiment of the present description, adjacent R2 and R5 combine with each other to form a substituted or unsubstituted ring.

According to an embodiment of the present description, adjacent R2 and R5 combine with each other to form a substituted or unsubstituted carbazole ring, a substituted or unsubstituted hexahydrocarbazole ring, or join through B to form a substituted or unsubstituted carbazole ringAnd (4) a ring.

According to an embodiment of the present specification, adjacent R2 and R5 combine with each other to form a carbazole ring substituted with deuterium, or an alkyl group of 1 to 3 carbon atoms substituted with deuterium; a hexahydrocarbazole ring substituted or unsubstituted with deuterium or an alkyl group having 1 to 3 carbon atoms substituted with deuterium, or linked through B to form a structure containing a C-substituted amino group₃Substituted phenyl substituted or unsubstitutedAnd (4) a ring.

According to one embodiment of the present description, adjacent R2 and R5 combine with each other to form a CD-protected article₃A substituted or unsubstituted hexahydrocarbazole ring.

According to an embodiment of the present specification, the above R1 to R5 are represented by-L-R11,

l is a direct bond, O, S, SO₂A substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group,

r11 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present specification, L is a direct bond, O, S, SO₂A substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, L is a direct bond, O, S, SO₂A substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

According to one embodiment of the present specification, L is a direct bond, O, S, SO₂Or a substituted or unsubstituted alkylene group having 1 to 5 carbon atoms.

According to one embodiment of the present specification, L is a direct bond, O, S, SO₂A substituted or unsubstituted methylene group, or a substituted or unsubstituted methylenepropylene group.

According to one embodiment of the present specification, L is a direct bond, O, S, SO₂Quilt CD₃A substituted or unsubstituted methylene group, or a propylene group substituted or unsubstituted with deuterium.

According to one embodiment of the present specification, L is a direct bond, O, or CD₃A substituted or unsubstituted methylene group, or a propylene group substituted or unsubstituted with deuterium.

According to one embodiment of the present description, R11 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present specification, R11 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted amine group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to one embodiment of the present specification, R11 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted amine group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms.

According to one embodiment of the present specification, R11 is hydrogen, deuterium, CD₃、CF₃Or by deuterium or CD₃Substituted or unsubstituted phenyl.

According to one embodiment of the present specification, R11 is hydrogen, deuterium, CD₃Or by deuterium or CD₃Substituted or unsubstituted phenyl.

According to one embodiment of the present specification, R1 or R2 and adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring.

According to one embodiment of the present specification, R1 or R2 and adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic to tetracyclic aliphatic hydrocarbon ring, a substituted or unsubstituted monocyclic to tetracyclic aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of a monocyclic to tetracyclic aliphatic hydrocarbon ring and a monocyclic to tetracyclic aromatic hydrocarbon ring.

According to one embodiment of the present specification, R1 or R2 and adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring, a substituted or unsubstituted monocyclic to tetracyclic aromatic hydrocarbon ring, a substituted or unsubstituted monocyclic to tricyclic aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of a monocyclic or bicyclic aliphatic hydrocarbon ring and a monocyclic or bicyclic aromatic hydrocarbon ring.

According to one embodiment of the present specification, R1 or R2 and adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 30 carbon atoms, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to one embodiment of the present specification, R1 or R2 and adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 2 to 20 carbon atoms, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an embodiment of the present description, R1 or R2 is directly bonded to R3 or R5, respectively, or is bonded through B substituted with a substituted or unsubstituted phenyl group, or is bonded to adjacent groups to each other to form a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted carbazole ring, a substituted or unsubstituted cyclopentene ring, a substituted or unsubstituted cyclohexene ring, a substituted or unsubstituted cycloheptene ring, a substituted or unsubstituted tetrahydronaphthalene ring, a substituted or unsubstituted dihydrobenzodiazepine ringAlkene (dihydrobenzol [ b ]]dioxine) ring, substituted or unsubstituted tetrahydroethyl bridged naphthalene (tetrahydronaphthalene) ring, substituted or unsubstituted bicycloheptene ring, substituted or unsubstitutedOr a substituted or unsubstituted hexahydrocarbazolyl group. The above groups are substituted or unsubstituted with 1 or more groups or 2 or more groups bonded selected from deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present description, R1 or R2 is directly bonded to R3 or R5, respectively, or is combined with adjacent groups to each other to form a substituted or unsubstituted indene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted cyclopentene ring, a substituted or unsubstituted cyclohexene ring, or a substituted or unsubstituted tetrahydroethyl bridged naphthalene (tetrahydronaphthalene) ring. The above groups are substituted or unsubstituted with 1 or more groups or 2 or more groups selected from deuterium, methyl, ethyl, propyl, butyl and phenyl.

According to an embodiment of the present specification, when R1 or R2 and an adjacent group are bonded to each other to form a substituted or unsubstituted ring, R1 or R2 is directly bonded to R3 or R5, respectively, to form a carbazole ring or a hexahydrocarbazole ring, or includes a linkage through B to form a carbazole ringThe case of a ring. The above rings are substituted or unsubstituted.

According to an embodiment of the present disclosure, when R1 or R2 and an adjacent group are bonded to each other to form a substituted or unsubstituted ring, the ring is represented by any one of the following chemical formulas C1 to C3.

In the above chemical formulas C1 to C3,

x21, X22 and X31, equal to or different from each other, are each independently O, S, CP11P12 or NP13,

p1 and P11 to P13, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with adjacent groups to form a substituted or unsubstituted ring,

b1 is an integer of 1 to 3,

p1 is an integer of 0 to 10, p2 and p3 are each an integer of 0 to 4,

when P1 to P3 are each 2 or more, 2 or more P1 s may be the same as or different from each other,

indicates where the formed rings are fused.

According to an embodiment of the present description, X21 and X22 are the same or different from each other, and are each independently O, S or CP11P 12.

According to an embodiment of the present description, X31 is O, S, CP11P12 or NP 13.

According to one embodiment of the present specification, P1 and P11 to P13 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combines with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

According to one embodiment of the present specification, P1 and P11 to P13 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or combines with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

According to an embodiment of the present specification, P1 and P11 to P13, which are the same or different from each other, are each independently hydrogen, deuterium, an alkyl group substituted or unsubstituted with deuterium, a phenyl group, or combine with adjacent groups to each other to form a benzene ring substituted or unsubstituted with deuterium or an alkyl group substituted or unsubstituted with deuterium, or form a bicycloheptane ring or bicyclooctane ring.

According to an embodiment of the present specification, P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen, deuterium, methyl substituted or unsubstituted by deuterium, ethyl substituted or unsubstituted by deuterium, propyl substituted or unsubstituted by deuterium, butyl substituted or unsubstituted by deuterium, or phenyl, or combine with adjacent groups to form a benzene ring substituted or unsubstituted by deuterium or methyl substituted or unsubstituted by deuterium, or form a bicycloheptane ring or bicyclooctane ring.

According to an embodiment of the present description, b1 is 1 or 2.

According to an embodiment of the present description, p1 is an integer from 1 to 6.

According to an embodiment of the present description, p1 is an integer from 1 to 4.

According to an embodiment of the present description, p2 and p3 are integers from 1 to 4.

According to an embodiment of the present specification, R1 or R2, when bonded to an adjacent group to form a substituted or unsubstituted ring, is represented by any one of the following structures.

In the above structures, denotes a position where a formed ring is fused, and the above structures are substituted or unsubstituted with deuterium or an alkyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, the above structure is substituted or unsubstituted with deuterium, or with deuterium substituted or unsubstituted methyl, deuterium substituted or unsubstituted ethyl, deuterium substituted or unsubstituted propyl, or deuterium substituted or unsubstituted butyl.

According to an embodiment of the present specification, the above structure is substituted or unsubstituted with deuterium, or with deuterium substituted or unsubstituted methyl, deuterium substituted or unsubstituted ethyl, deuterium substituted or unsubstituted isopropyl, or deuterium substituted or unsubstituted tert-butyl.

According to one embodiment of the present disclosure, the structure is deuterium or CD₃Substituted or unsubstituted.

According to an embodiment of the present specification, when Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, at least one of X1, X2, and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present specification, when Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, at least one of R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present description, at least 2 of X1, X2, and R1 to R5 are alkyl groups of 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present description, at least 3 of X1, X2, and R1 to R5 are alkyl groups of 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present description, at least one of X1, X2, and R1 through R5 is selected from methyl substituted with deuterium, ethyl substituted with deuterium, or propyl substituted with deuterium.

According to an embodiment of the present description, at least one of X1, X2, and R1 through R5 is selected from methyl substituted with deuterium, ethyl substituted with deuterium, or isopropyl substituted with deuterium.

According to an embodiment of the present description, at least 2 of X1, X2, and R1 through R5 are selected from methyl substituted with deuterium, ethyl substituted with deuterium, or isopropyl substituted with deuterium.

According to an embodiment of the present description, at least 3 of X1, X2, and R1 through R5 are selected from methyl substituted with deuterium, ethyl substituted with deuterium, or isopropyl substituted with deuterium.

According to an embodiment of the present disclosure, at least 2 of the R1 to R5 are alkyl groups having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present disclosure, at least 3 of the R1 to R5 are alkyl groups having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present description, at least one of R1 to R5 is selected from-CD₃、-C₂D₅、CH₂CD₃、CD(CD₃)₂Or CH (CD)₃)₂。

According to the bookIn one embodiment of the specification, at least 2 of R1-R5 are selected from the group consisting of-CD₃、-C₂D₅、CH₂CD₃、CD(CD₃)₂Or CH (CD)₃)₂。

According to an embodiment of the present description, at least 3 of R1 to R5 are selected from-CD₃、-C₂D₅、CH₂CD₃、CD(CD₃)₂Or CH (CD)₃)₂。

According to an embodiment of the present description, at least one of R1 to R5 is CD₃。

According to an embodiment of the present description, at least 2 of R1 to R5 are CD₃。

According to an embodiment of the present description, at least 3 of R1 to R5 are CD₃。

According to one embodiment of the present description, R4, equal to or different from each other, are each independently hydrogen or CD_---₃。

According to an embodiment of the present disclosure, chemical formula 1 may be represented by chemical formula 101 below.

[ chemical formula 101]

In the above chemical formula 101, the definition of the substituent is the same as that in chemical formula 1.

According to one embodiment of the present specification, Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, or is represented by the following chemical formula 2.

According to an embodiment of the present specification, Y is methyl substituted with deuterium, ethyl substituted with deuterium, or propyl substituted with deuterium.

According to an embodiment of the present specification, Y is methyl substituted with deuterium, ethyl substituted with deuterium, or isopropyl substituted with deuterium.

According to one embodiment of the present disclosure, Y is CDH₂、CD₂H、CD₃、C₂D₅、CH₂CD₃、CD(CD₃)₂Or CH (CD)₃)₂。

According to one embodiment of the present disclosure, Y is-CD₃、-C₂D₅、CH₂CD₃、CD(CD₃)₂Or CH (CD)₃)₂。

According to one embodiment of the present disclosure, Y is CDH₂、CD₂H or CD₃。

According to an embodiment of the present specification, Y is CD₃。

According to one embodiment of the present specification, Y is represented by the following chemical formula 2.

[ chemical formula 2]

In the above-described chemical formula 2,

b1 and B2, which are the same or different from each other, are each independently an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring,

r6 and R7 are the same as or different from each other and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, 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, which are the same or different from each other, are each independently an integer of 1 to 11, and when r6 and r7 are each 2 or more, the substituents in parentheses are the same or different from each other,

represents the binding site of chemical formula 1.

According to an embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to an embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tricyclic aliphatic hydrocarbon ring or a substituted or unsubstituted monocyclic to tricyclic aromatic hydrocarbon ring.

According to an embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring or a substituted or unsubstituted monocyclic aromatic hydrocarbon ring.

According to an embodiment of the present specification, B1 and B2, which are the same or different from each other, are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted cyclohexane ring.

According to an embodiment of the present specification, B1 and B2, which are the same or different from each other, are each independently a benzene ring or are each CD₃A substituted or unsubstituted cyclohexane ring.

According to one embodiment of the present description, B1 and B2 are benzene rings.

According to one embodiment of the present disclosure, B1 is a benzene ring, B2 is a substituted CD₃A substituted or unsubstituted cyclohexane ring.

According to an embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsulfoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12 to 30 carbon atoms.

According to an embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsulfoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12 to 20 carbon atoms.

According to an embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylsulfoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12 to 16 carbon atoms.

According to an embodiment of the present specification, R6 and R7, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, ethyl substituted or unsubstituted with deuterium, propyl substituted or unsubstituted with deuterium, butyl substituted or unsubstituted with deuterium, trimethylsilyl substituted or unsubstituted with deuterium, or CD₃Substituted or unsubstituted phenyl, or R6 and R7 combine with each other to form a substituted or unsubstituted phenyl group that is deuterated, methylated, or CDed₃Or a tert-butyl substituted or unsubstituted carbazole ring; or by deuterium, methyl,CD₃Or tert-butyl-substituted or unsubstituted hexahydrocarbazole rings, or with adjacent groups bound to each other to form deuterium, methyl, CD₃Or a tert-butyl substituted or unsubstituted cyclohexene ring.

According to an embodiment of the present specification, R6 and R7, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, isopropyl substituted or unsubstituted with deuterium, tert-butyl, trimethylsilyl or phenyl, or R6 and R7 are combined with each other to form a methyl-, CD-or a methyl-, CD-or a phenyl-substituted or unsubstituted with deuterium₃Or a tert-butyl substituted or unsubstituted carbazole ring; or by methyl, CD₃Or a tert-butyl substituted or unsubstituted hexahydrocarbazole ring, or a cyclohexene ring substituted or unsubstituted with a methyl group by bonding to each other with adjacent groups.

According to an embodiment of the present specification, R6 and R7, which are the same or different from each other, are each independently hydrogen, deuterium, methyl substituted or unsubstituted with deuterium, isopropyl substituted or unsubstituted with deuterium, tert-butyl, trimethylsilyl or phenyl, or combine with each other with adjacent groups to form the following structure. The following structures are substituted or unsubstituted with deuterium, methyl substituted or unsubstituted with deuterium, isopropyl or tert-butyl substituted or unsubstituted with deuterium,represents the binding site of chemical formula 1.

According to an embodiment of the present description, R6 and R7, equal to or different from each other, are each independently hydrogen, methyl, CD₃Or tert-butyl, or R6 and R7 combine with each other to form a methyl, CD₃Or a tert-butyl substituted or unsubstituted carbazole ring; or by methyl, CD₃Or a tert-butyl substituted or unsubstituted hexahydrocarbazole ring.

According to an embodiment of the present description, R6 and R7, equal to or different from each other, are each independently hydrogen or tert-butyl, or R6 and R7 are bound to each otherTo form a coated CD₃Substituted or unsubstituted carbazole ring, or by CD₃A substituted or unsubstituted hexahydrocarbazole ring.

According to an embodiment of the present specification, when Y is represented by the above chemical formula 2, at least one of X1, X2, and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present specification, when Y is represented by the above chemical formula 2, at least one of R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present description, at least 2 of X1, X2, and R1 to R7 are alkyl groups of 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present description, at least 3 of X1, X2, and R1 to R7 are alkyl groups of 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present description, at least one of X1, X2, and R1 through R7 is selected from methyl substituted with deuterium, ethyl substituted with deuterium, or propyl substituted with deuterium.

According to an embodiment of the present description, at least one of X1, X2, and R1 through R7 is selected from methyl substituted with deuterium, ethyl substituted with deuterium, or isopropyl substituted with deuterium.

According to an embodiment of the present description, at least 2 of X1, X2, and R1 through R7 are selected from methyl substituted with deuterium, ethyl substituted with deuterium, or isopropyl substituted with deuterium.

According to an embodiment of the present description, at least 3 of X1, X2, and R1 through R7 are selected from methyl substituted with deuterium, ethyl substituted with deuterium, or isopropyl substituted with deuterium.

According to an embodiment of the present disclosure, at least 2 of the R1 to R7 are alkyl groups having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present disclosure, at least 3 of the R1 to R7 are alkyl groups having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present description, at least one of R1 to R7 is selected from-CD₃、-C₂D₅、CH₂CD₃、CD(CD₃)₂Or CH (CD)₃)₂。

According to an embodiment of the present description, at least 2 of R1 to R7 are selected from-CD₃、-C₂D₅、CH₂CD₃、CD(CD₃)₂Or CH (CD)₃)₂。

According to an embodiment of the present description, at least 3 of R1 to R7 are selected from-CD₃、-C₂D₅、CH₂CD₃、CD(CD₃)₂Or CH (CD)₃)₂。

According to an embodiment of the present description, at least one of R1 to R7 is CD₃。

According to an embodiment of the present description, at least 2 of R1 to R7 are CD₃。

According to an embodiment of the present description, at least 3 of R1 to R7 are CD₃。

According to an embodiment of the present specification, r1 and r2 are the same as or different from each other, and each is independently an integer of 1 to 3.

According to an embodiment of the present description, r1 and r2 are the same as or different from each other, and each is independently 1 or 2.

According to an embodiment of the present specification, r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 11.

According to an embodiment of the present specification, r3 and r5 to r7 are the same as or different from each other, and each is independently an integer of 1 to 9.

According to an embodiment of the present specification, r3 and r5 to r7 are the same as or different from each other, and each is independently an integer of 1 to 5.

According to an embodiment of the present specification, r3 and r5 to r7 are the same as or different from each other, and each is independently an integer of 1 to 3.

According to an embodiment of the present description, r4 is an integer of 1 or 2.

According to one embodiment of the present description, r4 is 1.

According to one embodiment of the present description, r4 is 2.

According to an embodiment of the present specification, n is an integer of 1 or 2.

According to one embodiment of the present specification, n is 1.

According to an embodiment of the present specification, n is 2.

According to an embodiment of the present description, r4+ n is an integer of 2 or 3.

According to an embodiment of the present specification, when r1 to r7 and n are each 2 or more, the substituents in parentheses are the same as or different from each other.

According to an embodiment of the present disclosure, the chemical formula 2Represented by any one of the following chemical formulas 201 to 203.

In the above-described chemical formulas 201 to 203,

g6 and G7, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring,

g16 and G17, which are identical to or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group,

g6 and g7 are each integers from 1 to 5, g6 'and g7' are integers from 1 to 4, g7 "is an integer from 1 to 8,

when G6, G7, G6', G7' and G7' are each 2 or more, each of 2 or more G6 and G7 is the same as or different from each other,

represents the binding site of chemical formula 1.

According to one embodiment of the present disclosure, G6 and G7 are as defined above for R6 and R7.

According to an embodiment of the present specification, G16 and G17, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present specification, G16 and G17, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to an embodiment of the present specification, G16 and G17, equal to or different from each other, are each independently hydrogen, deuterium, or an alkyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, G16 and G17, equal to or different from each other, are each independently hydrogen, deuterium, or methyl substituted or unsubstituted with deuterium.

According to an embodiment of the present description, G16 and G17 are methyl or CD₃。

According to one embodiment of the present specification, the chemical formula 2 is represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,indicating the binding site.

According to an embodiment of the present disclosure, each of g6, g7, g6', g7' and g7 ″ is an integer of 1 to 4.

According to an embodiment of the present disclosure, each of g6, g7, g6', g7' and g7 ″ is an integer of 1 to 3.

According to an embodiment of the present disclosure, each of g6, g7, g6', g7' and g7 "is 1 or 2.

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

[ chemical formula 1-1]

[ chemical formulas 1-2]

In the above chemical formulas 1-1 and 1-2,

r1 to R7, A1, A2, B1, B2, X1, X2 and R1 to R7 are as defined in the above chemical formula 1,

z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

m is an integer of 1 or 2, and when m is 2, Z are the same or different from each other,

r4+ m is an integer of 2 or 3.

According to an embodiment of the present description, Z is methyl substituted with deuterium, ethyl substituted with deuterium, or propyl substituted with deuterium.

According to an embodiment of the present specification, Z is methyl substituted with deuterium, ethyl substituted with deuterium, or isopropyl substituted with deuterium.

According to an embodiment of the present description, Z is methyl substituted with deuterium.

According to an embodiment of the present disclosure, Z is CDH₂、CD₂H or CD₃。

According to an embodiment of the present description, Z is CD₃。

According to an embodiment of the present specification, m is an integer of 1 or 2.

According to an embodiment of the present specification, m is 1.

According to an embodiment of the present description, m is 2.

According to an embodiment of the present specification, in the above chemical formula 1-1, at least one of X1, X2, and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present specification, in the chemical formula 1-1, at least one of R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present specification, in the above chemical formula 1-2, at least one of X1, X2, and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present specification, in the chemical formula 1-2, at least one of R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

According to an embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-3 to 1-7.

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

[ chemical formulas 1 to 5]

[ chemical formulas 1 to 6]

[ chemical formulas 1 to 7]

In the above chemical formulas 1-3 to 1-7,

r1 to R7, X1, X2 and R1 to R7 are as defined in the above chemical formula 1, Z is an alkyl group of 1 to 3 carbon atoms substituted with deuterium,

m is an integer of 1 or 2, and when m is 2, Z are the same or different from each other.

According to one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formulae 1 to 8.

[ chemical formulas 1 to 8]

In the above-mentioned chemical formulas 1 to 8,

a1, A2, R1 to R5, R1 to R5, Y and n are as defined in chemical formula 1,

x3 is CRaRb, NRc, O, PRd, S, PORe, SO₂SiRfRg or BRh,

ra to Rh are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

According to an embodiment of the present disclosure, the definitions of Ra to Rh in the above chemical formulas 1 to 8 are the same as those of Ra to Rh in chemical formula 1.

According to an embodiment of the present specification, the chemical formula 1 is represented by the following chemical formulas 1 to 9 or 1 to 10.

[ chemical formulas 1 to 9]

[ chemical formulas 1-10]

In the above chemical formulas 1 to 9 and 1 to 10,

x1, X2, A1, A2, R1, R3 to R5, R1, R3 to R5, Y and n are as defined in chemical formula 1,

a3 and A4 are the same as or different from each other and each independently represents a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic heterocyclic ring, or a substituted or unsubstituted fused ring of an aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,

r21 and R22 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring,

r21 and r22 are each an integer of 1 to 9,

when R21 and R22 are each 2 or more, 2 or more of R21 and R22 are each the same as or different from each other.

According to one embodiment of the present specification, a3 is represented by any one of the following structural formulae.

According to an embodiment of the present disclosure, the above definitions of R1 or R2 and the adjacent group are applied to A3 and a 4.

According to an embodiment of the present specification, A3 and a4 are the same as or different from each other, and each is independently represented by any one of the following structures.

In the above structures, denotes a position where a formed ring is fused, and the above structures are substituted or unsubstituted with deuterium or an alkyl group substituted or unsubstituted with deuterium.

According to an embodiment of the present disclosure, the definitions of P1 apply to R21 and R22.

According to an embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1 to 11 or 1 to 12.

[ chemical formulas 1 to 11]

[ chemical formulas 1 to 12]

In the above chemical formulas 1 to 11 and 1 to 12,

x1, X2, R1 to R5, R1, R3, R4, A1, Y and n are as defined in the above chemical formula 1,

x101 is a direct bond or-BR 103-,

r103, G101 and G102, which may be the same or different from each other, are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

r2' is 1 or 2,

r5' is an integer from 1 to 4,

r5' is an integer from 1 to 8,

when R2', R5' and R5 "are each 2 or more, 2 or more of R2 and R5 are each the same as or different from each other.

According to one embodiment of the present disclosure, the chemical formula 1 is represented by any one of the following compounds.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In the present invention, the HOMO and LUMO levels of the compounds can also be adjusted by introducing various substituents into the core structure of the above-described structure.

The compound of chemical formula 1 of the present invention can produce a core structure as shown in the following reaction formula. The substituents may be combined by a method known in the art, and the kind, position and number of the substituents may be changed according to a technique known in the art.

< reaction formula >

[ general formula 1]

In the above general formula 1, Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, or a substituted or unsubstituted amine group, and n is 1 to 3.

In the above formula 1, based on a dibromobenzene compound containing a deuterium substituted alkyl group or an amine group, and a diarylamine compound containing or not containing a deuterium substituted alkyl group, a Buckwald-Hartwig amination (Buckwald-Hartwig amine) reaction is used to obtain [ intermediate 1] having the same amine group. Next, boron can be introduced using boron triiodide to synthesize the above [ final product 1 ].

[ general formula 2]

In the above general formula 2, Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, or a substituted or unsubstituted amine group, and n is 1 to 3.

In the above formula 2, based on a bromochlorobenzene compound containing a deuterium substituted alkyl group or an amine group, and a diarylamine compound containing or not containing a deuterium substituted alkyl group, the respective different amine groups are obtained by a braz wald-hart vich amination reaction [ intermediate 2-b ]. Next, boron can be introduced using boron triiodide to synthesize the above [ final product 2 ].

[ general formula 3]

Deuterium-substituted methyl groups can be introduced by deuterium substitution reaction using a transition metal catalyst based on a boron compound containing a methyl group, i.e., [ intermediate 3 ]. In the above reaction formula 3, a compound in which a methyl group is present at a specific position is exemplified, but a deuterium-substituted alkyl group may be introduced by replacing a C — H bond of an alkyl group present at various positions of a boron compound with a C — D bond at a substitution rate of 15% or more, in addition to a methyl group.

The conjugated length and the energy band gap of the above compounds have a close relationship. Specifically, the longer the conjugation length of the compound, the smaller the band gap.

In the present invention, as described above, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure. In addition, in the present specification, by introducing various substituents into the core structure having the above-described structure to adjust the HOMO and LUMO levels of the compound, and by replacing the C — H bond of the methyl group in the thus-introduced substituents with a stronger C — D bond, a compound having improved optical characteristics and lifetime characteristics can be synthesized.

In addition, the present specification provides an organic light emitting device comprising the compound as described above.

In one embodiment of the present specification, there is provided an organic light emitting device including: a first electrode; a second electrode; and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.

In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.

In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.

The organic layer of the organic light-emitting device in the present specification may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, as a representative example of the organic light emitting device of the present specification, 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 as an organic layer. 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 embodiment of the present disclosure, the organic layer includes a light emitting layer including the compound represented by chemical formula 1.

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

In one embodiment of the present disclosure, the organic layer includes a light emitting layer including the compound represented by the chemical formula 1 as a blue fluorescent dopant of the light emitting layer.

In one embodiment of the present disclosure, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound represented by chemical formula 1.

In one embodiment of the present disclosure, the organic layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons includes the compound represented by chemical formula 1.

In one embodiment of the present disclosure, the organic layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by the chemical formula 1.

In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by the chemical formula 1.

In one embodiment of the present specification, the organic light-emitting device further includes 1 or 2 or more layers selected from 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 embodiment of the present specification, the light-emitting layer further includes a host compound.

In one embodiment of the present specification, the light-emitting layer further includes a host compound, and at least one hydrogen of the host compound is substituted by deuterium.

In one 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 embodiment, more than 40% of the host compound is substituted with deuterium. In another embodiment, more than 60% of the host compound is substituted with deuterium. In another embodiment, more than 80% of the host compound is substituted with deuterium. In another embodiment, 100% of the host compound is substituted with deuterium.

In one 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 above-mentioned chemical formula H,

l20 and L21, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,

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

r20 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

r20 is an integer of 0 to 8, and when R20 is 2 or more, R20 may be the same as or different from each other.

In one embodiment of the present specification, L20 and L21, which are the same or different from each other, are each independently a direct bond, an arylene group having 6 to 40 carbon atoms, or a 2-valent heterocyclic group having 6 to 40 carbon atoms.

In one embodiment of the present specification, L20 and L21, which are the same or different from each other, are each independently a direct bond, an arylene group having 6 to 20 carbon atoms, or a 2-valent heterocyclic group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L20 and L21, which are the same or different from each other, are each independently a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a 2-valent dibenzofuranyl group, or a 2-valent dibenzothiophenyl group.

In one embodiment of the present specification, Ar20 and Ar21, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21, which are the same as or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar20 and Ar21, which are the same or different from each other, are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group.

In one embodiment of the present specification, Ar20 and Ar21, which are the same or different from each other, are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenalkenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted naphthalene benzofuryl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted naphthobenzothienyl group.

In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a biphenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a naphthyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a dibenzofuranyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a naphthobenzofuranyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a dibenzothiophenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, or a naphthobenzothiophenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

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

In one embodiment of the present specification, Ar20 and Ar21, which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with deuterium, a naphthyl group substituted or unsubstituted with deuterium, or a dibenzofuranyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R20 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In one embodiment of the present specification, R20 is hydrogen, deuterium, a fluoro group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R20 is hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R20 is hydrogen, deuterium, a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

In one embodiment of the present specification, R20 is hydrogen, deuterium, or naphthyl substituted or unsubstituted with deuterium.

In one embodiment of the present specification, r20 is an integer from 1 to 8.

In one embodiment of the present disclosure, the formula H may include at least one deuterium.

In one embodiment of the present specification, the chemical formula H is represented by the following chemical formula I or J.

[ chemical formula I ]

[ chemical formula J ]

In the above formulae I and J, the substituents are defined as in formula H.

In one embodiment of the present specification, when the compound represented by the above chemical formula H is substituted with deuterium, 30% or more is substituted with deuterium. In another embodiment, greater than 40% of the structure of formula H is substituted with deuterium. In another embodiment, more than 60% of the structure of formula H is substituted with deuterium. In another embodiment, 80% or more of the structure of formula H is substituted with deuterium. In another embodiment, 100% of the structure of formula H above is substituted with deuterium.

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

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

In one embodiment of the present specification, the light-emitting layer further contains 2 or more host compounds. When the light-emitting layer includes 2 types of hosts, the content of the hosts may be 10:90 to 90:10 based on the first host and the second host. The content between the above bodies may be 20:80 to 80:20 in one example, and 40:60 to 60:40 in another example.

The light-emitting layer may further contain a host material, and the host may contain an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like. Specifically, the aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, triazine derivatives, and the like, and mixtures of 2 or more of them are possible, but not limited thereto.

In one embodiment of the present specification, the 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 2 or more organic layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, at least one of the 2 or more organic layers including the compound represented by the chemical formula 1.

In one embodiment of the present specification, the 2 or more organic layers may be 2 or more selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a layer that simultaneously transports and injects holes, and an electron-blocking layer.

In one embodiment of the present disclosure, the organic layer includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes the compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the above chemical formula 1 may be contained in 1 layer of the above 2 or more electron transport layers, and may be contained in each of the 2 or more electron transport layers.

In addition, in an embodiment of the present specification, when the compound is included in each of the 2 or more electron transport layers, materials other than the compound represented by the above chemical formula 1 may be the same as or different from each other.

When the organic 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. The n-type dopant may be a material known in the art, and for example, a metal or a metal complex may be used. For example, the electron transport layer including the compound represented by the above chemical formula 1 may further include LiQ (Lithium Quinolate).

In one embodiment of the present disclosure, the organic layer includes 2 or more hole transport layers, and at least one of the 2 or more hole transport layers includes the compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the above chemical formula 1 may be contained in 1 layer of the 2 or more hole transport layers, and may be contained in each of the 2 or more hole transport layers.

In addition, in one embodiment of the present specification, when the compound represented by the above chemical formula 1 is included in each of the 2 or more hole transport layers, materials other than the compound represented by the above chemical formula 1 may be the same as or different from each other.

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

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

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

In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present disclosure, the organic light emitting device may have a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.

For example, fig. 1 and 2 show examples of the structure of an organic light emitting device according to an embodiment of the present specification. The above-described fig. 1 and 2 illustrate the organic light emitting device, and are not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 7, and a cathode 11 are sequentially stacked. In the structure as described above, the above-described compound may be contained in the above-described light-emitting layer 3.

Fig. 2 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, a first hole injection layer 3, a second hole injection layer 4, a hole transport layer 5, an electron blocking layer 6, a light emitting layer 7, a first electron transport layer 8, a second electron transport layer 9, an electron injection layer 10, and a cathode 11 are sequentially stacked. In the structure as described above, the compound may be contained in 1 or more of the first hole injection layer 3, the second hole injection layer 4, the hole transport layer 5, the electron blocking layer 6, the light emitting layer 7, the first electron transport layer 8, the second electron transport layer 9, and the electron injection layer 10.

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

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

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order.

In addition, the compound represented by the above chemical formula 1 may be formed into an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to these methods, an organic light-emitting device can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.

The first electrode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. For example, there are metals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO₂A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The second electrode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. For example, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives or heterocyclic compounds. Specifically, the aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic-containing compounds include dibenzofuran derivatives and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.

As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like, in addition to the compound represented by the above chemical formula 1. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, perylene, and the like having an arylamine group,Diindenopyrene, and the like. Further, the styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 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. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.

In the present specification, when the compound represented by the above chemical formula 1 is contained in an organic layer other than the light-emitting layer or another light-emitting layer is provided, the light-emitting substance of the light-emitting layer is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and a substance having high quantum efficiency with respect to fluorescence or phosphorescence is preferable. For example, there are 8-hydroxyquinoline aluminum complexes (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) isAzole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; a polyfluorene; and rubrene, but the present invention is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode. The hole injection substance is preferably as follows: a substance having an ability to transport holes, having an effect of injecting holes from the first electrode, and having an excellent hole injection effect for the light-emitting layer or the light-emitting material. Further, a substance having excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material is preferable. Further, a substance having excellent film-forming ability is preferable. Further, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the first electrode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include metalloporphyrin (porphyrin), oligothiophene, and arylamine-based organic substances; a carbazole-based organic substance; a nitrile-based organic compound; hexanenitrile hexaazatriphenylene series organic matter; quinacridone (quinacridone) -based organic compounds; perylene (perylene) -based organic compounds; and polythiophene-based conductive polymers such as anthraquinone and polyaniline, or a mixture of 2 or more kinds of them in the above examples, but the present invention is 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-transporting substance is a substance capable of receiving holes from the first electrode or the hole-injecting layer and transferring the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic substances, carbazole-based organic substances, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The electron transport layer receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron-transporting substance is a substance that can satisfactorily receive electrons from the second electrode and transfer the electrons to the light-emitting layer, and is preferably a substance having a high mobility to electrons. As an example, there is an Al complex of 8-hydroxyquinolineCompound comprising Alq₃The complex of (3), an organic radical compound, a hydroxyflavone-metal complex, a triazine derivative, LiQ, etc., but are not limited thereto. The electron transport layer may be used with any desired first electrode material as used in the art. Suitable first electrode substances are, in particular, the usual substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium, samarium, etc., in each case accompanied by an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron-injecting substance is preferably as follows: a substance having an excellent ability to transport electrons, having an effect of injecting electrons from the second electrode, and having an excellent electron injection effect for the light-emitting layer or the light-emitting material. Further, it is preferable that the exciton generated in the light-emitting layer is prevented from migrating to the hole-injecting layer and that the thin film-forming ability is excellent. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,Oxadiazole, triazole, triazine, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, and mixtures of 2 or more of the above examples, but not limited thereto.

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

The electron blocking layer is a layer that prevents holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, so that the lifetime and efficiency of the device can be improved. A known material can be used without limitation, and the light-emitting layer and the hole-injecting layer or the light-emitting layer and the layer which performs hole injection and hole transport simultaneously can be formed therebetween.

The hole blocking layer is a layer that prevents holes from reaching the second electrode, and can be formed under the same conditions as those of the hole injection layer. Specifically, there areAn oxadiazole derivative or a triazole derivative, a phenanthroline derivative, an aluminum complex (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 bi-directional emission type, depending on the material used.

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

The compound according to the present specification can also function in a principle similar to that applied to an organic light-emitting device in an organic light-emitting device typified by an organic phosphorescent device, an organic solar cell, an organic photoreceptor, an organic transistor, or the like. For example, the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer disposed between the cathode and the anode, and the photoactive layer may include the compound.

Modes for carrying out the invention

Hereinafter, in order to specifically explain the present specification, the details will be explained by referring to examples, comparative examples, and the like. However, the examples and comparative examples according to the present specification may be modified into various forms, and the scope of the present specification is not to be construed as being limited to the examples and comparative examples described in detail below. The examples and comparative examples of the present specification are provided to more fully describe the present specification to those skilled in the art.

Synthesis example 1 Synthesis of Compound 1

<1-a > production of Compound 1-a

In a three-necked flask, 1-bromo-3-chloro-5- (methyl-d)₃) Benzene (1 equivalent) and 5-tert-butyl-N- (4-tert-butylphenyl) - [1,1' -biphenylyl]After (1 equivalent) of the-2-amine was dissolved in toluene (0.3M), sodium tert-butoxide (1.2 equivalents) and bis (tri-tert-butylphosphine) palladium (0) (0.01 equivalent) were added, and the mixture was stirred under reflux in an argon atmosphere for 2 hours. After the reaction is finished, cooling to normal temperature, and adding H₂And O, transferring the reaction liquid to a separating funnel, and extracting. The extract was washed with MgSO₄The resulting mixture was dried and concentrated, and the sample was purified by silica gel column chromatography to obtain compound 1-a. (yield 82%, MS [ M + H ]]⁺＝486)。

<1-b > production of Compound 1-b

Through comparison with synthetic example<1-a>The same method, from 1-a and bis (4- (prop-2-yl-d)₇) Phenyl) amine gave 1-b. (yield 86%, MS [ M + H ]]⁺＝717)。

<1-c > production of Compound 1

In a three-necked flask, compound 1-b was dissolved in 1, 2-dichlorobenzene (0.1M), and after adding boron triiodide (2 equivalents), the mixture was stirred at 160 ℃ for 4 hours under an argon atmosphere. The reaction was cooled to 0 ℃, N-diisopropylethylamine (20 eq) was added and stirred for 1 hour. Using toluene and H₂The O was extracted in a separatory funnel. The extract was washed with MgSO₄Drying, concentrating, and purifying the sample by silica gel column chromatographyAfter that, sublimation purification was performed, thereby obtaining compound 1. (yield 15%, MS [ M + H ]]⁺＝724)。

Synthesis example 2 Synthesis of Compound 2

<2-a > production of Compound 2-a

Through comparison with synthetic example<1-a>In the same way, from 1-bromo-3-chloro-5- (methyl-d)₃) Benzene and bis (4-tert-butylphenyl) amine give 2-a. (yield 88%, MS [ M + H ]]⁺＝410)。

<2-b > production of Compound 2-b

Through comparison with synthetic example<1-a>The same procedure, starting from 2-a and 4-tert-butyl-N- (4-tert-butylphenyl) -2- (methyl-d₃) Aniline gave 2-b. (yield 92%, MS [ M + H ]]⁺＝672)

<2-c > production of Compound 2

Through comparison with synthetic example<1-c>In the same manner, Compound 2 was obtained from 2-b. (yield 17%, MS [ M + H ]]⁺＝679)

Synthesis example 3 Synthesis of Compound 3

<3-a > production of Compound 3-a

Through comparison with synthetic example<1-a>The same method, from 2-a and 5- (2- (phenyl-d)₅) Prop-2-yl-1, 1,1,3,3,3-d₅) -N- (4-propan-2-yl-d₇) Phenyl) - [1,1' -biphenyl]-2',3,3',4,4',5',6,6'-d₈The 2-amine gives 3-a. (yield 69%, MS [ M + H ]]⁺＝804)。

<3-b > production of Compound 3

Through comparison with synthetic example<1-c>In the same manner, Compound 3 was obtained from 3-a. (yield 20%, MS [ M + H ]]⁺＝812)。

Synthesis example 4 Synthesis of Compound 4

<4-a > production of Compound 4-a

Through comparison with synthetic example<1-a>In the same way, from 1-bromo-3-chloro-5- (methyl-d)₃) Benzene and bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine gave 4-a. (yield 86%, MS [ M + H ]]⁺＝517)。

<4-b > production of Compound 4-b

Through comparison with synthetic example<1-a>The same procedure was followed, starting from 4-a and N- (5-tert-butyl-2 ',4',6' -tris (prop-2-yl-d)₇) - [1,1' -Biphenyl]-2-yl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine gives 4-b. (yield 82%, MS [ M + H ]]⁺＝1039)。

<4-c > production of Compound 4

Through comparison with synthetic example<1-c>In the same manner, a compound derived from 4-bAnd (4) an object. (yield 12%, MS [ M + H ]]⁺＝1047)。

Synthesis example 5 Synthesis of Compound 5

<5-a > production of Compound 5-a

Through comparison with synthetic example<1-a>The same method, from 1-bromo-3-chloro-5- (prop-2-yl-d)₇) Benzene and N- (4-tert-butylphenyl) -5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-amine gave 5-a. (yield 79%, MS [ M + H ]]⁺＝495)。

<5-b > production of Compound 5-b

Through comparison with synthetic example<1-a>The same procedure was followed, starting from 5-a and 7-tert-butyl-N- (2,4, 6-tris (methyl-d)₃) Dibenzo [ b, d ]]Furan-3-amine gives 5-b. (yield 80%, MS [ M + H ]]⁺＝825)。

<5-c > production of Compound 5

Through comparison with synthetic example<1-c>In the same manner, Compound 5 was obtained from 5-b. (yield 10%, MS [ M + H ]]⁺＝833)。

Synthesis example 6 Synthesis of Compound 6

<6-a > production of Compound 6-a

Through comparison with synthetic example<1-a>The same method, from 1-bromo-3-chloro-5- (prop-2-yl-d)₇) Benzene and bis (4-tert-butyl)Phenyl) amine gave 6-a. (yield 88%, MS [ M + H ]]⁺＝441)。

<6-b > production of Compound 6-b

Through comparison with synthetic example<1-a>The same method, from 6-a and N- (4-tert-butyl-2- (methyl-d)₃) Phenyl) -5,6,7, 8-tetrahydronaphthalene-5, 5,6,6,7,7,8,8-d₈The 2-amine gives 6-b. (yield 71%, MS [ M + H ]]⁺＝709)。

<6-c > production of Compound 6

Through comparison with synthetic example<1-c>In the same manner, Compound 6 was obtained from 6-b. (yield 13%, MS [ M + H ]]⁺＝717)。

Synthesis example 7 Synthesis of Compound 7

<7-a > production of Compound 7-a

Through comparison with synthetic example<1-a>In the same manner, 1-bromo-3, 5-dichlorobenzene and bis (4-tert-butylphenyl) amine gave 7-a. (yield 92%, MS [ M + H ]]⁺＝426)。

<7-b > production of Compound 7-b

Through comparison with synthetic example<1-a>In the same manner, 7-b was obtained from 7-a and bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine. (yield 87%, MS [ M + H ]]⁺＝779)。

<7-c > production of Compound 7-c

In a three-necked flask, compound 7-b was dissolved in 1, 2-dichlorobenzene (0.1M), and after adding boron triiodide (2 equivalents), the mixture was stirred at 160 ℃ for 8 hours under an argon atmosphere. The reaction was cooled to 0 ℃, N-diisopropylethylamine (20 eq) was added and stirred for 1 hour. Using toluene and H₂The O was extracted in a separatory funnel. The extract was washed with MgSO₄The sample was dried and concentrated, and purified by silica gel column chromatography to obtain compound 7-c. (yield 23%, MS [ M + H ]]⁺＝787)。

<7-d > production of Compound 7

In a three-necked flask, compound 7-c (1 equivalent) and 4a,9 a-bis (methyl-d) were placed₃) -2,3,4,4a,9,9 a-hexahydro-1H-carbazole (1.1 eq) was dissolved in toluene (0.3M), and after adding sodium tert-butoxide (1.5 eq) and bis (tri-tert-butylphosphine) palladium (0) (0.01 eq), stirring was carried out under reflux conditions under argon atmosphere for 4 hours. After the reaction is finished, cooling to normal temperature, and adding H₂And O, transferring the reaction liquid to a separating funnel, and extracting. The extract was washed with MgSO₄The resulting mixture was dried and concentrated, and the sample was purified by silica gel column chromatography and purified by sublimation to obtain compound 7. (yield 63%, MS [ M + H ]]⁺＝958)。

Synthesis example 8 Synthesis of Compound 8

<8-a > production of Compound 8-a

Through comparison with synthetic example<1-a>The same method, from 1-bromo-3-chloro-5- (prop-2-yl-d)₇) Benzene and N- (4-Tert-butylphenyl) -5,5,8, 8-tetramethyl-3-phenyl-5, 6,7, 8-tetrahydronaphthalen-2-amine gives 8-a. (yield 88%, MS [ M + H ]]⁺＝571)。

<8-b > production of Compound 8-b

Through comparison with synthetic example<1-a>The same method is used for preparing the catalyst from 8-a and N- (4-tert-butylphenyl) -2- (methyl-d₃) -4- (tert-butyl-d)₉) Aniline gave 8-b. (yield 76%, MS [ M + H ]]⁺＝842)。

<8-c > production of Compound 8

Through comparison with synthetic example<1-c>In the same manner, Compound 8 was obtained from 8-b. (yield 10%, MS [ M + H ]]⁺＝850)。

Synthesis example 9 Synthesis of Compound 9

<9-a > production of Compound 9-a

Through comparison with synthetic example<1-a>In the same manner, 1-bromo-3, 5-dichlorobenzene and bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine gave compound 9-a. (yield 86%, MS [ M + H ]]⁺＝534)。

<9-b > production of Compound 9-b

Through comparison with synthetic example<1-a>The same procedure was followed, starting from 9-a and 4-tert-butyl-N- (3- (4a,9 a-dimethyl-1, 2,3,4,4a,9 a-hexahydro-9H-carbazol-9-yl) phenyl) -2- (methyl-d₃) The aniline gives the compound 9-b. (yield 66%, MS [ M + H ]]⁺＝939)。

<9-c > production of Compound 9-c

Through comparison with synthetic example<7-c>In the same manner, Compound 9-c was obtained from Compound 9-b. (yield 31%, MS [ M + H ]]⁺＝947)。

<9-d > production of Compound 9

Through comparison with synthetic example<7-d>In the same manner, Compound 9 was obtained from Compound 9-c. (yield 72%, MS [ M + H ]]⁺＝1118)。

Synthesis example 10 Synthesis of Compound 10

<10-a > production of Compound 10-a

Through comparison with synthetic example<1-a>In the same way, from 1-bromo-3-chloro-5- (ethyl-d)₅) Benzene and 4-tert-butyl-2- (methyl-d)₃) The (3-tert-amylphenyl) aniline gave 10-a. (yield 95%, MS [ M + H ]]⁺＝456)。

<10-b > production of Compound 10-b

Through comparison with synthetic example<1-a>The same method is carried out by using 10-a and N- (4- (tert-butyl) phenyl) dibenzo [ b, d]Thienyl-2-amine gives 10-b. (yield 76%, MS [ M + H ]]⁺＝751)。

<10-c > production of Compound 10

Through comparison with synthetic example<1-c>In the same manner, Compound 10 was obtained from 10-b. (yield 12%, MS [ M + H ]]⁺＝759)。

Synthesis example 11 Synthesis of Compound 11

<11-a > production of Compound 11-a

Through comparison with synthetic example<1-a>The same method, from 1-bromo-3-chloro-5- (prop-2-yl-d)₇) Benzene and bis (4-tert-butylphenyl) amine give 11-a. (yield 91%, MS [ M + H ]]⁺＝441)。

<11-b > production of Compound 11-b

Through comparison with synthetic example<1-a>Same method, from 11-a and N¹,N¹-bis (2-fluorophenyl) -N³- (2,4, 6-tris (methyl-d)^- ₃) Phenyl) benzene-1, 3-diamine gave 11-b. (yield 63%, MS [ M + H ]]⁺＝828)。

<11-c > production of Compound 11

Through comparison with synthetic example<1-c>In the same manner, Compound 11 was obtained from 11-b. (yield 8%, MS [ M + H ]]⁺＝836)。

Synthesis example 12 Synthesis of Compound 12

<12-a > production of Compound 12-a

Through comparison with synthetic example<1-a>In the same way, from 1-bromo-3-chloro-5- (ethyl-d)₅) Benzene and N- (4-tert-butylphenyl) dibenzo [ b, d]Furan-2-amine gives 12-a. (yield 88%, MS [ M + H ]]⁺＝459)。

<12-b > production of Compound 12-b

Through comparison with synthetic example<1-a>The same method is used for preparing the compound from 12-a and 5,5,8, 8-tetramethyl-N- (2,4, 5-tri (methyl-d)₃) Phenyl) -5,6,7, 8-tetrahydronaphthalen-2-amine gave 12-b. (yield 82%, MS [ M + H ]]⁺＝753)。

<12-c > production of Compound 12

Through comparison with synthetic example<1-c>In the same manner, Compound 12 was obtained from 12-b. (yield 11%, MS [ M + H ]]⁺＝761)。

Synthesis example 13 Synthesis of Compound 13

<13-a > production of Compound 13-a

Through comparison with synthetic example<1-a>The same method is used for preparing the compound 2-a and N- (4-tert-butylphenyl) -2, 8-bis (methyl-d)₃) Dibenzo [ b, d ]]Furan-4-amine gives 13-a. (yield 81%, MS [ M + H ]]⁺＝722)。

<13-b > production of Compound 13

Through comparison with synthetic example<1-c>In the same manner, Compound 13 was obtained from 13-a. (yield 16%, MS [ M + H ]]⁺＝730)。

Synthesis example 14 Synthesis of Compound 14

<14-a > production of Compound 14-a

Through comparison with synthetic example<1-a>The same procedure was followed for the preparation of the compounds 1-a and 2,4, 6-tris (methyl-d)₃) -N- (4- (trimethylsilyl) phenyl) aniline gave 14-a. (yield 89%, MS [ M + H ]]⁺＝741)。

<14-b > production of Compound 14

Through comparison with synthetic example<1-c>In the same manner, Compound 14 was obtained from 14-a. (yield 14%, MS [ M + H ]]⁺＝749)。

Synthesis example 15 Synthesis of Compound 15

<15-a > production of Compound 15-a

Through comparison with synthetic example<1-a>In the same way, from 1-bromo-3-chloro-5- (ethyl-d)₅) Benzene and bis (5,5,8, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) amine gave 15-a. (yield 81%, MS [ M + H ]]⁺＝533)。

<15-b > production of Compound 15-b

Through comparison with synthetic example<1-a>The same method is used for preparing the compound from 15-a and N- (4-tert-butylphenyl) -2,9, 9-tri (methyl-d)₃) -9H-fluorene-1, 4,5,6,7,8-d₆The-3-amine gives 15-a. (yield 71%, MS [ M + H ]]⁺＝867)。

<15-c > production of Compound 15

Through comparison with synthetic example<1-c>In the same manner, Compound 15 was obtained from 15-b. (yield 12%, MS [ M + H ]]⁺＝875)。

Synthesis example 16 Synthesis of Compound 16

<16-a > production of Compound 16-a

Through comparison with synthetic example<1-a>The same method, from 1-bromo-3-chloro-5- (prop-2-yl-d)₇) Benzene and N- (5,5,8, 8-tetramethyl-3- (methyl-d 3) -5,6,7, 8-tetrahydronaphthalen-2-yl) -9, 10-dihydro-9, 10-ethylxanthen-2-amine gave 16-a. (yield 85%, MS [ M + H ]]⁺＝584)。

<16-b > production of Compound 16-b

Through comparison with synthetic example<1-a>The same method is used for preparing the product from 16-a and N- (4-tert-butylphenyl) -2- (ethyl-d₅) -4- (methyl-d)₃) Benzene-3, 5,6-d₃The amine gives 16-b. (yield 82%, MS [ M + H ]]⁺＝826)。

<16-c > production of Compound 16

Through comparison with synthetic example<1-c>In the same manner, Compound 16 was obtained from 16-b. (yield 11%, MS [ M + H ]]⁺＝834)。

Synthesis example 17 Synthesis of Compound 17

<17-a > production of Compound 17-a

Through comparison with synthetic example<1-a>The same process, from 2-a and 6-tert-butyl-4 a,9 a-bis (methyl-d)₃) -2,3,4,4a,9,9 a-hexahydro-1H-carbazole gave 17-a. (yield 88%, MS [ M + H ]]⁺＝636)。

<17-b > production of Compound 17

Through comparison with synthetic example<1-c>In the same manner, Compound 17 was obtained from 17-a. (yield 17%, MS [ M + H ]]⁺＝644)。

Synthesis example 18 Synthesis of Compound 18

<18-a > production of Compound 18-a

Through comparison with synthetic example<1-a>The same procedure was carried out using 1-bromo-3, 5-dichlorobenzene and bis (4- (methyl-d)₃) Phenyl) amine gave 18-a. (yield 83%, MS [ M + H ]]⁺＝348)。

<18-b > production of Compound 18-b

Through comparison with synthetic example<1-a>The same method is carried out by 18-a and N- (4- (methyl-d)₃) Phenyl) -3- (trifluoromethoxy) aniline gave compound 18-b. (yield 81%, MS [ M + H ]]⁺＝582)。

<18-c > production of Compound 18-c

Through comparison with synthetic example<7-c>In the same manner, Compound 18-c was obtained from Compound 18-b. (yield 24%, MS [ M + H ]]⁺＝590)。

<18-d > production of Compound 18

Through comparison with synthetic example<7-d>In the same manner, Compound 18 was obtained from Compound 18-c and bis (4-tert-butylphenyl) amine. (yield 59%, MS [ M + H ]]⁺＝835)。

Synthesis example 19 Synthesis of Compound 19

<19-a > production of Compound 19-a

Through comparison with synthetic example<1-a>In the same way, from 7-a and N- (4-tert-butylphenyl) dibenzo [ b, d]Furan-3-amine gave 19-a. (yield 89%, MS [ M + H ]]⁺＝705)。

<19-b > production of Compound 19-b

Through comparison with synthetic example<7-c>In the same manner, 19-b was obtained from 19-a. (yield 17%, MS [ M + H ]]⁺＝713)。

<19-c > production of Compound 19

Through comparison with synthetic example<7-d>The same method is used for preparing the compound from 19-b and 2,3,6, 7-tetra (methyl-d)₃) -9H-carbazole gave compound 19. (yield 63%, MS [ M + H ]]⁺＝912)。

Synthesis example 20 Synthesis of Compound 20

<20-a > production of Compound 20-a

In a three-necked flask, 1-bromo-3-chloro-5- (methyl-d)₅) Benzene (1 equivalent) and 4-tert-butylaniline (2.1 equivalent) were dissolved in toluene (0.3M), and after adding sodium tert-butoxide (3 equivalents) and bis (tri-tert-butylphosphine) palladium (0) (0.01 equivalent), the mixture was stirred under reflux conditions under argon atmosphere for 2 hours. After the reaction is finished, cooling to normal temperature, and adding H₂And O, transferring the reaction liquid to a separating funnel, and extracting. The extract was washed with MgSO₄The sample was dried and concentrated, and purified by silica gel column chromatography to obtain compound 20-a. (yield 85%, MS [ M + H ]]⁺＝390)。

<20-b > production of Compound 20-b

Through comparison with synthetic example<1-a>The same method is used for preparing the compound from 20-a and 2,2' - (propyl-2, 2-diyl-1, 1,1,1,3,3,3-d₆) Bis (4-bromo-1- (methyl-d)₃) Benzene) gave 20-b. (yield 71%, MS [ M + H ]]⁺＝622)。

<20-c > production of Compound 20

Through comparison with synthetic example<1-c>In the same manner, Compound 20 was obtained from 20-b. (yield 5%, MS [ M + H ]]⁺＝630)。

< experimental example 1: example of device

Example 1.

Indium Tin Oxide (ITO) and a process for producing the sameThe glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, the following HI-A and HI-B were addedThe first hole injection layer and the second hole injection layer are formed by thermal vacuum evaporation.

On the hole injection layer, the following HT-A andthe hole transport layer is formed by vacuum evaporation.

On the hole transport layer, the following HT-B andthe electron blocking layer is formed by vacuum evaporation.

Next, on the electron blocking layer, the following compound 1 was added as a blue light emitting dopant in an amount of 4 wt% based on the total weight of the light emitting layer; as a host, the following BH-1 was added in an amount of 96 wt% based on the total weight of the light-emitting layerThe thickness of (2) is vacuum-evaporated to form a light-emitting layer.

Then, on the light-emitting layer, as a first electron transporting layer, the following compound ET-A andvacuum evaporation was performed, and then ET-B and LiQ, described below, were vacuum evaporated at a weight ratio of 1:1, to obtainForming a second electron transport layer.

Vacuum evaporating LiQ on the second electron transport layer to obtain a third electron transport layerThe electron injection layer is formed by vacuum evaporation.

On the electron injection layer, toThe thickness of (2) is obtained by evaporating aluminum and silver at a weight ratio of 10:1, and then depositing aluminum thereonIs deposited to form a cathode.

In the above process, the evaporation speed of the organic material is maintainedAluminum maintenance of cathodeThe vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition^-7～5×10^-8And supporting to thereby fabricate an organic light emitting device.

Examples 2 to 20 and comparative examples 1 to 4

Except that in example 1 above, compounds described in table 1 below were used instead of compound 1 and BH-1 as dopants and hosts of the light-emitting layer, organic light-emitting devices of examples 2 to 20 and comparative examples 1 to 4 were respectively produced by the same method as in example 1.

The application of 10mA/cm to the organic light emitting devices of the above-described examples 1 to 20 and comparative examples 1 to 4 was measured²Voltage at current density of (1), efficiency (cd/A/y), and application of 20mA/cm²Current density of (2) and life time (T)₉₅) The results are shown in table 1 below. At this time, T₉₅Expressed in that the current density is 20mA/cm²The initial luminance below is a ratio of the time required for the luminance to decrease to 95% at 100% based on comparative example 1.

[ Table 1]

Examples 21 to 24 and comparative example 5

Organic light-emitting devices of examples 21 to 24 and comparative example 5 were produced in the same manner as in example 1, except that in example 1, compounds described in table 2 below were used as dopants in the light-emitting layer instead of compound 1, and compounds described in table 2 below were used as hosts in the light-emitting layer.

The weight ratio of the first host to the second host of the light emitting layer is 50: 50.

The application of 10mA/cm to the organic light emitting devices of the above-mentioned examples 21 to 24 and comparative example 5 was measured²Voltage at current density of (1), efficiency (cd/A/y), and application of 20mA/cm²Current density of (2) and life time (T)₉₅) The results are shown in table 1 below. At this time, T₉₅Expressed in that the current density is 20mA/cm²The initial luminance below is a ratio of the time required for the luminance to decrease to 95% at 100% based on comparative example 1.

[ Table 2]

The conversion efficiency (cd/a/y) is considered from the current efficiency (cd/a) to the color purity (CIEy) of the material, and is an important efficiency reference value in small and large organic light emitting devices aiming at high luminance and high color reproduction rate.

As is apparent from the device results of tables 1 and 2, when an organic light emitting device is configured using a dopant substance containing an alkyl group having 1 to 3 carbon atoms substituted with deuterium, which is represented by [ chemical formula 1] according to an embodiment of the present specification, the device is superior in both conversion efficiency and lifetime performance compared to a device other than this.

Specifically, the compound of chemical formula 1 of the present invention is characterized by binding an alkyl group substituted with deuterium at a specific position, and thus shows the results of about 10% maximum efficiency and about 2 to 3 times longer lifetime as compared with the compounds BD-A, BD-C and BD-D which are not such comparative examples.

In a state where a compound is excited, a phenomenon occurs in which electrons constituting a resonance structure in the compound are aggregated. In this case, the light-emitting characteristics of the compound can be effectively controlled by substituting an alkyl group at a specific position where the current density becomes higher or lower. When an alkyl group substituted with deuterium is introduced as in the compound of chemical formula 1 of the present invention, the light emitting characteristics of the compound can be effectively adjusted without greatly changing the molecular weight, and thus the device using the same shows particularly excellent results in terms of efficiency and lifetime.

In addition, the compound of chemical formula 1 including the alkyl group having 1 to 3 carbon atoms substituted with deuterium shows the effects of superior efficiency and lifetime compared to the comparative example BD-B including the butyl group substituted with deuterium.

This is because a methyl radical, an ethyl radical, and a propyl radical, which are alkyl radicals having 1 to 3 carbon atoms, are unstable as compared with a butyl radical, which is a tertiary carbon radical (having 4 or more carbon atoms), and therefore C (sp) is present³)-C(sp²) The decomposition process of the compound due to the bond cleavage is relatively suppressed, thereby ensuring the stability of the compound structure.