WO2021107680A1

WO2021107680A1 - Compound and organic light-emitting element comprising same

Info

Publication number: WO2021107680A1
Application number: PCT/KR2020/017074
Authority: WO
Inventors: 금수정; 조혜민; 김선우; 홍완표; 이재구; 김훈준
Original assignee: 주식회사 엘지화학
Priority date: 2019-11-29
Filing date: 2020-11-27
Publication date: 2021-06-03

Abstract

The present specification provides a compound expressed by chemical formula 1, and an organic light-emitting element comprising the compound.

Description

Compound and organic light emitting device comprising same

This application is based on the filing date of Korean Patent Application No. 10-2019-0156840, filed with the Korean Intellectual Property Office on November 29, 2019, and Korean Patent Application No. 10-2020-0060630, filed with the Korean Intellectual Property Office on May 20, 2020 claims, the entire contents of which are incorporated herein by reference.

The present specification relates to a compound and an organic light emitting device including the same.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and these excitons are When it falls back to the ground state, it lights up.

The development of new materials for the organic light emitting device as described above is continuously required. Among them, in the case of a blue organic light emitting device, high color purity and long lifespan characteristics are essential, but due to instability due to high energy of a blue material, there is a lack of technology for simultaneously implementing them. Recently, a thermally activated delayed fluorescent material having a core structure including boron has been newly developed and has been attracting attention for its high efficiency and color purity, but has a disadvantage in that the triplet energy is high and the reverse intersystem transition rate is slow, so the lifespan is short. Accordingly, there is a demand for the development of a blue organic light emitting material that simultaneously realizes high color purity and long life characteristics.

The present specification provides a compound and an organic light emitting device including the same.

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

[Formula 1]

In Formula 1,

X1 is O or S;

A1 is a substituted or unsubstituted heterocyclic ring; a substituted or unsubstituted aromatic hydrocarbon ring; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

A2 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; Or a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,

r1 is an integer from 1 to 3,

When r1 is 2 or more, the 2 or more R1 are the same as or different from each other,

Formula 1 includes at least one condensed aliphatic hydrocarbon ring substituted with a substituted or unsubstituted alkyl group.

In addition, the present specification is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer includes the compound.

The compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, high color purity and/or lifespan characteristics may be improved in the organic light emitting device.

1 and 2 illustrate an organic light emitting diode according to an exemplary embodiment of the present specification.

3 is a diagram illustrating a photoluminescence analysis graph according to Experimental Example 2 of the present specification.

4 to 12 are diagrams illustrating molecular models implemented by simulation of Experimental Example 1 of the present specification.

13 is a diagram showing a thermogravimetric analysis graph of Example 46 of the present specification.

14 is a diagram showing a thermogravimetric analysis graph of Comparative Example 16 of the present specification.

15 is a diagram showing a thermogravimetric analysis graph of Comparative Example 17 of the present specification.

[Explanation of code]

1: substrate

2: first electrode

3: light emitting layer

4: second electrode

5: hole injection layer

6: hole transport layer

7: Electron blocking layer

8: first electron transport layer

9: Second electron transport layer

10: electron injection layer

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

The conventional organic light-emitting device to which a boron-based compound is applied has better efficiency than an organic light-emitting device to which a pyrene-based compound is applied, but has a short lifespan. However, since the compound represented by Formula 1 includes S or O, the first triplet excitation energy of Formula 1 is lowered, and thus the difference between the first singlet excitation energy and the first triplet excitation energy increases. Therefore, by suppressing triplet quenching, an organic light emitting device including the same is increased in device lifetime in the host-dopant system.

In addition, since Formula 1 includes at least one condensed aliphatic hydrocarbon ring substituted with a substituted or unsubstituted alkyl group, and has an asymmetric structure, 1) the sublimation temperature is lower than that of the conventional boron-based compound and has thermal stability, 2) Because it has high oxidation stability, it is possible to increase the lifespan of the organic light emitting device including the same, 3) minimize molecular planarity as the structural features, and 4) increase the volume of the molecule, so it is included by minimizing concentration quenching The efficiency of the organic light emitting device is increased.

Throughout this specification, the term "combination of these" included in the expression of the Markush form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the Markush form, and the components It is meant to include one or more selected from the group consisting of.

Examples of substituents in the present specification are described below, but are not limited thereto.

In this specification,

means the part to be connected.

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; an alkyl group; cycloalkyl group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; alkenyl group; haloalkyl group; haloalkoxy group; an arylalkyl group; silyl group; boron group; amine group; aryl group; hydrocarbon ring group; And it means that it is substituted with one or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

In the present specification, that two or more substituents are connected means that the hydrogen of any one substituent is connected with another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.

or

may be a substituent of In addition, the connection of three substituents means that (substituent 1)-(substituent 2)-(substituent 3) is continuously connected, as well as (substituent 2) and (substituent 3) are connected to (substituent 1). include For example, a phenyl group, a naphthyl group and an isopropyl group are connected,

,

or

may be a substituent of The above definition applies equally to the case where 4 or more substituents are connected.

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

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

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

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.

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

In the present specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.

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

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

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.

In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.

When the fluorene group is substituted,

,

and

and the like, but is not limited thereto.

As used herein, the "adjacent" group refers to a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the arylalkyl group means that the alkyl group is substituted with an aryl group, and examples of the aryl group and the alkyl group described above may be applied to the aryl group and the alkyl group of the arylalkyl group.

In the present specification, the aryloxy group means substituted with an aryl group instead of an alkyl group of the alkoxy group in the definition of the alkoxy group, and the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5- Dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4 -Methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenane a toryloxy group, a 9-phenanthryloxy group, and the like, but is not limited thereto.

In the present specification, the alkyl group of the alkyltioxy group is the same as the example of the alkyl group described above. Specifically, the alkyl thiooxy group includes, but is not limited to, methyl thiooxy group, ethyl thiooxy group, tert-butyl thiooxy group, hexyl thiooxy group, octyl thiooxy group, and the like.

In the present specification, the aryl group in the arylthioxy group is the same as the example of the aryl group described above. Specifically, the arylthioxy group includes, but is not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like.

In the present specification, the heterocyclic group includes atoms other than carbon and one or more heteroatoms, specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, etc., an aromatic heterocyclic group, or an aliphatic heterocyclic group. The aromatic heterocyclic group may be represented by a heteroaryl group. The number of carbon atoms of the heterocyclic group is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), decahydrobenzocarbazole group, hexahydrocarbazole group, dihydrobenzoazacillin group, dihydroindenocarbazole group, spirofluorene xanthene group, spirofluorene thioxanthene group, tetrahydronaphthothiophene group, tetrahydronaphthofuran group, tetrahydrobenzothiophene group, tetrahydrobenzofuran group, etc. However, it is not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, or the like. Examples of the above-described alkyl group may be applied to the alkyl group in the alkylsilyl group, the examples of the aryl group may be applied to the aryl group in the arylsilyl group, and the alkyl group and aryl group in the alkylarylsilyl group may include the alkyl group and the aryl group. Examples of can be applied, the heteroaryl group among the heteroarylsilyl group, the examples of the heterocyclic group can be applied.

In the present specification, the boron group _{may be -BR 100} R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. Specifically, the boron group includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre nylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

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

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

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a straight-chain or branched alkyl group. The alkylamine group including two or more alkyl groups may include a straight-chain alkyl group, a branched-chain alkyl group, or a straight-chain alkyl group and a branched alkyl group at the same time. For example, the alkyl group in the alkylamine group may be selected from the examples of the alkyl group described above.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heterocyclic group described above.

In the present specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of the cycloalkyl group, aryl group, and combinations thereof. and the hydrocarbon ring group is a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo [2.2.1] heptyl group, a bicyclo [2.2.1] octyl group, a tetrahydronaphthalene group, a tetrahydroanthracene group, 1,2, 3,4-tetrahydro-1,4-methanonaphthalene group, and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group, and the like, but are not limited thereto.

In the present specification, the meaning of "adjacent" in "adjacent groups combine with each other to form a ring" is the same as described above, and the "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, except that the cycloalkyl group, the aryl group, and combinations thereof are not monovalent. It may be selected from among examples, and the hydrocarbon ring is benzene, cyclohexane, adamantane, bicyclo [2.2.1] heptane, bicyclo [2.2.1] octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2, 3,4-tetrahydro-1,4-methanonaphthalene, and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, and the like, but are not limited thereto.

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

In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, but are not limited thereto.

Unless defined otherwise herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of a conflict the present specification, including definitions, will control unless a specific passage is recited. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

According to an exemplary embodiment of the present specification, X1 is O.

According to an exemplary embodiment of the present specification, X1 is S.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following

Chemical Formula

2 or 3.

[Formula 2]

[Formula 3]

In

Formulas

2 and 3,

The definitions of A1, A2, X1, Ar1, Ar2, R1, and r1 are the same as those defined in Formula 1 above.

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

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

The definitions of A1, A2, Ar1, Ar2, R1 and r1 are the same as those defined in Formula 1 above.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1-1, 1-1-2, 1-2-1, and 1-2-2.

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-2-1]

[Formula 1-2-2]

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

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formulas 1-3 or 1-4.

[Formula 1-3]

[Formula 1-4]

In Formulas 1-3 and 1-4,

The definitions of X1, A2, Ar1, Ar2, R1 and r1 are the same as those defined in Formula 1 above,

A "1 is a substituted or unsubstituted aliphatic hydrocarbon ring,

R11 and R12 are the same as or different from each other, and each independently hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine 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 ring.

r11 is an integer of 1 to 4, and when r11 is 2 or more, R11 of 2 or more are the same as or different from each other,

r12 is 1 or 2, and when r12 is 2, the two R12s are the same as or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-3-1, 1-3-2, 1-4-1, and 1-4-2.

[Formula 1-3-1]

[Formula 1-3-2]

[Formula 1-4-1]

[Formula 1-4-2]

In Formulas 1-3-1, 1-3-2, 1-4-1 and 1-4-2,

A "1 is a substituted or unsubstituted aliphatic hydrocarbon ring,

R11 and R12 are the same as or different from each other, and each independently hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine 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 ring,

According to an exemplary embodiment of the present specification, Chemical Formula 1-4 is represented by the following Chemical Formula 1-4-3 or 1-4-4.

[Formula 1-4-3]

[Formula 1-4-4]

In Formulas 1-4-3 and 1-4-4,

A "1 is a substituted or unsubstituted aliphatic hydrocarbon ring,

R12 is hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

According to an exemplary embodiment of the present specification, Chemical Formula 1-4 is represented by any one of Chemical Formulas 1-4-5, 1-4-6, 1-4-7, and 1-4-8.

[Formula 1-4-5]

[Formula 1-4-6]

[Formula 1-4-7]

[Formula 1-4-8]

In the formulas 1-4-5, 1-4-6, 1-4-7, and 1-4-8,

A "1 is a substituted or unsubstituted aliphatic hydrocarbon ring,

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes one condensed aliphatic hydrocarbon ring substituted with a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes two condensed aliphatic hydrocarbon rings substituted with a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes three condensed aliphatic hydrocarbon rings substituted with a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes four condensed aliphatic hydrocarbon rings substituted with a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one condensed monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted with a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms. .

According to an exemplary embodiment of the present specification, Formula 1 includes at least one condensed monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms substituted with a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms. .

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one condensed monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 10 carbon atoms substituted with a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms. .

According to an exemplary embodiment of the present specification, Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 3 to 30 carbon atoms substituted with a linear or branched alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 3 to 20 carbon atoms substituted with a linear or branched alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Chemical Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 3 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Formula 1 includes at least one monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium do.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 5 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Chemical Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 6 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 5 to 8 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Chemical Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 6 to 8 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 5 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 6 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 5 to 8 carbon atoms substituted with a linear or branched alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Formula 1 is a monocyclic or polycyclic aliphatic hydrocarbon condensed ring having 6 to 8 carbon atoms substituted with a linear or branched alkyl group having 1 to 5 carbon atoms unsubstituted or substituted with deuterium at least one include

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one condensed monocyclic aliphatic hydrocarbon ring having 5 or 6 carbon atoms substituted with a linear or branched alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium. .

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one condensed monocyclic aliphatic hydrocarbon ring having 5 or 6 carbon atoms substituted with a linear or branched alkyl group having 1 to 10 carbon atoms that is unsubstituted or substituted with deuterium. .

According to an exemplary embodiment of the present specification, Chemical Formula 1 is a cyclohexane condensed ring substituted with one or more selected from the group consisting of a methyl group substituted with deuterium, a methyl group, and deuterium; a condensed bicyclo[2.2.1]heptane ring substituted with a methyl group; and at least one selected from the group consisting of a condensed bicyclo [2.2.1] octane ring substituted with a methyl group.

According to an exemplary embodiment of the present specification, Formula 1 is a tetramethylcyclohexane condensed ring; tetradeuterium tetramethylcyclohexane; tetratrideuterium methylcyclohexane condensed ring; dimethylbicyclo[2.2.1]heptane condensed ring; and at least one selected from the group consisting of a dimethylbicyclo[2.2.1]octane condensed ring.

According to an exemplary embodiment of the present specification, Formula 1 is a cyclohexane condensed ring substituted with one or more selected from the group consisting of deuterium, a methyl group, and a methyl group substituted with deuterium; a condensed bicyclo[2.2.1]heptane ring substituted with a methyl group; or at least one condensed bicyclo[2.2.1]octane ring substituted with a methyl group.

According to an exemplary embodiment of the present specification, Formula 1 is a tetramethylcyclohexane condensed ring; tetradeuterium tetramethylcyclohexane; tetratrideuterium methylcyclohexane condensed ring; a condensed bicyclo[2.2.1]heptane ring substituted with a methyl group; or at least one condensed bicyclo[2.2.1]octane ring substituted with a methyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one condensed cyclohexane ring substituted with a methyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one condensed cyclohexane ring substituted with a methyl group substituted with deuterium.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one condensed cyclohexane ring substituted with a methyl group and deuterium.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one condensed bicyclo[2.2.1]heptane ring substituted with a methyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one condensed bicyclo[2.2.1]octane ring substituted with a methyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one tetramethylcyclohexane.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one tetramethylcyclohexane substituted with deuterium.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one tetradeuterium tetramethylcyclohexane.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one tetratrideuterium methylcyclohexane condensed ring.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one tetratrideuterium methylcyclohexane condensed ring substituted with deuterium.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one dimethylbicyclo[2.2.1]heptane condensed ring.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one dimethylbicyclo[2.2.1]octane condensed ring.

According to an exemplary embodiment of the present specification, Chemical Formula 1 includes at least one of the following structures.

In the structure,

denotes a site bonded to Chemical Formula 1, and in the structure, hydrogen at a position that can be substituted with deuterium may be substituted with deuterium.

The structure may be formed by bonding two tert-butyl groups.

According to an exemplary embodiment of the present specification, the meaning of "including at least one condensed aliphatic hydrocarbon ring substituted with a substituted or unsubstituted alkyl group" means an aliphatic hydrocarbon ring substituted with an alkyl group at at least one of the condensable positions of Formula 1 above. will be condensed

According to an exemplary embodiment of the present specification, the condensed aliphatic hydrocarbon ring substituted with an alkyl group is included in at least one of A1, A2, Ar1, Ar2, and R1 of Formula 1 above.

In the present specification, the inclusion of at least one aliphatic hydrocarbon condensed ring substituted with an alkyl group in Formula 1 is described as an example as follows, but is not limited thereto.

For example, 1) when Ar1 of Formula 1 includes an aliphatic hydrocarbon condensed ring substituted with an alkyl group

Ar1 of Formula 1 is a phenyl group, and Ar1 is an aliphatic hydrocarbon condensed ring substituted with the alkyl group.

When including, Ar2 may be represented by a tetrahydronaphthalene group substituted with a methyl group, and may be represented by the following structure, but is not limited thereto.

2) When A2 of Formula 1 includes an aliphatic hydrocarbon condensed ring substituted with an alkyl group

A2 of Formula 1 is benzene, and A2 is an aliphatic hydrocarbon condensed ring substituted with the alkyl group.

In the case of including, A2 may be represented by tetrahydronaphthalene substituted with a methyl group, and may be represented by the following structure, but Formula 1 is not limited to the following structure.

According to an exemplary embodiment of the present specification, A1 is a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms; a substituted or unsubstituted 6 to 30 monocyclic or polycyclic aromatic hydrocarbon ring; a substituted or unsubstituted 3 to 30 monocyclic or polycyclic aliphatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, wherein A2 is a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms. or a polycyclic aromatic hydrocarbon ring; a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms; or a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, wherein R1 is hydrogen; a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted amine group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A1 is a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms; a substituted or unsubstituted 6 to 30 monocyclic or polycyclic aromatic hydrocarbon ring; a substituted or unsubstituted 3 to 30 monocyclic or polycyclic aliphatic hydrocarbon ring; or a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A1 is a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms; a substituted or unsubstituted 6 to 20 monocyclic or polycyclic aromatic hydrocarbon ring; a substituted or unsubstituted 3 to 20 monocyclic or polycyclic aliphatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A1 is substituted or unsubstituted tetrahydronaphthalene; substituted or unsubstituted naphthalene; substituted or unsubstituted 1,2,3,4-tetrahydro-1,4-methanonaphthalene; or substituted or unsubstituted 1,2,3,4-tetrahydro-1,4-ethanonaphthalene; substituted or unsubstituted benzene; substituted or unsubstituted dibenzofuran; substituted or unsubstituted dibenzothiophene; substituted or unsubstituted fluorene; substituted or unsubstituted xanthene; Or a substituted or unsubstituted dibenzosilol.

In A1, "substituted or unsubstituted" is deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Monocyclic or polycyclic having 6 to 30 carbon atoms, unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms aryl group; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylsilyl group having 6 to 30 carbon atoms; Monocyclic or polycyclic aryl having 6 to 30 carbon atoms, unsubstituted or substituted with one or more selected from the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a linear or branched alkylsilyl group having 1 to 30 carbon atoms amine group; N-aryl heteroarylamine group; an amine group containing a condensed ring group of monocyclic or polycyclic aromatic and aliphatic hydrocarbon rings having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; A monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

In A1, "substituted or unsubstituted" is deuterium; a cumyl group unsubstituted or substituted with deuterium; a methyl group unsubstituted or substituted with deuterium; isopropyl group; tert-butyl group; a phenyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, F, a methyl group, a tert-butyl group, and a phenyl group; a diphenylamine group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a methyl group, a tert-butyl group, and a trimethylsilyl group; a phenyltetrahydronaphthylamine group unsubstituted or substituted with one or more selected from the group consisting of a methyl group and a tert-butyl group; phenylbiphenylamine group; a ditetrahydronaphthylamine group unsubstituted or substituted with a methyl group; a phenyl fluorenylamine group unsubstituted or substituted with a methyl group; N-phenyldibenzofuranamine group; trimethylsilyl group; triphenylsilyl group; a carbazole group; a methyl group, and a hexahydrocarbazole group unsubstituted or substituted with one or more selected from the group consisting of a phenyl group; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, A1 is tetrahydronaphthalene; naphthalene; 1,2,3,4-tetrahydro-1,4-methanonaphthalene; 1,2,3,4-tetrahydro-1,4-ethanonaphthalene; benzene; dibenzofuran; dibenzothiophene; fluorene; xanten; or dibenzosilol, wherein the substituent is deuterium; queuing; a cumyl group substituted with deuterium; methyl group; isopropyl group; tert-butyl group; a phenyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, F, a methyl group, a tert-butyl group, and a phenyl group; a diphenylamine group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a methyl group, a tert-butyl group, and a trimethylsilyl group; a phenyltetrahydronaphthylamine group unsubstituted or substituted with one or more selected from the group consisting of a methyl group and a tert-butyl group; phenylbiphenylamine group; a ditetrahydronaphthylamine group unsubstituted or substituted with a methyl group; a phenyl fluorenylamine group unsubstituted or substituted with a methyl group; N-phenyldibenzofuranamine group; trimethylsilyl group; triphenylsilyl group; a carbazole group; a methyl group, and a hexahydrocarbazole group unsubstituted or substituted with one or more selected from the group consisting of a phenyl group; And it may be unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, A2 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A2 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms; or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A2 is substituted or unsubstituted benzene; substituted or unsubstituted cyclohexane; substituted or unsubstituted tetrahydronaphthalene; substituted or unsubstituted 1,2,3,4-tetrahydro-1,4-methanonaphthalene; or substituted or unsubstituted 1,2,3,4-tetrahydro-1,4-ethanonaphthalene.

In A2, "substituted or unsubstituted" is deuterium; a linear or branched alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

In A2, "substituted or unsubstituted" is deuterium; a cumyl group unsubstituted or substituted with deuterium; a methyl group unsubstituted or substituted with deuterium; isopropyl group; tert-butyl group; adamantyl group; a phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, A2 is benzene; cyclohexane; tetrahydronaphthalene; 1,2,3,4-tetrahydro-1,4-methanonaphthalene; or 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, wherein the substituent is deuterium; a cumyl group unsubstituted or substituted with deuterium; a methyl group unsubstituted or substituted with deuterium; isopropyl group; tert-butyl group; adamantyl group; a phenyl group unsubstituted or substituted with a methyl group or a tert-butyl group; And it may be unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms; or a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and 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 anthracene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted fluorene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted dibenzosilol group; a substituted or unsubstituted benzofluorene group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted naphthobenzothiophene group; a substituted or unsubstituted tetrahydronaphthobenzofuran group; Or a substituted or unsubstituted tetrahydronaphthalene group.

In Ar1 and Ar2, "substituted or unsubstituted" is deuterium; halogen group; cyano group; a linear or branched alkoxy group having 1 to 30 carbon atoms; a linear or branched alkyl group having 1 to 30 carbon atoms, unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylsilyl group having 6 to 30 carbon atoms; NRR' unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a condensed ring group of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; Deuterium, a halogen group, a cyano group, a linear or branched haloalkyl group having 1 to 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, and a straight chain having 1 to 30 carbon atoms substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more selected from the group consisting of a branched alkyl group; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

In Ar1 and Ar2, "substituted or unsubstituted" is deuterium; F; cyano group; methoxy group; trifluoromethyl group; trideuterium methyl group; methyl group; isopropyl group; tert-butyl group; n-butyl group; a cumyl group unsubstituted or substituted with deuterium; cyclohexyl group; trimethylsilyl group; triphenylsilyl group; a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, F, a cyano group, a trifluoromethyl group, a trideuterium methyl group, a trimethylsilyl group, a methyl group, an isopropyl group, a tert-butyl group and a phenyl group; a naphthyl group unsubstituted or substituted with deuterium; biphenyl group; phenanthrene group; anthracene group; tetrahydronaphthyl group unsubstituted or substituted with a methyl group; NRR'; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of a combination thereof, wherein R and R' are the same as or different from each other, and each independently substituted or unsubstituted with a methyl group or a tert-butyl group phenyl group; biphenyl group; Or a tetrahydronaphthyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; naphthyl group; anthracene group; phenanthrene group; fluorene group; dibenzofuran group; dibenzothiophene group; dibenzosilol group; benzofluorene group; naphthobenzofuran group; naphthobenzothiophene group; tetrahydronaphthobenzofuran group; Or a tetrahydronaphthalene group, wherein the substituent is deuterium; F; cyano group; methoxy group; trifluoromethyl group; trideuterium methyl group; methyl group; isopropyl group; tert-butyl group; n-butyl group; a cumyl group unsubstituted or substituted with deuterium; cyclohexyl group; trimethylsilyl group; triphenylsilyl group; a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, F, a cyano group, a trifluoromethyl group, a trideuterium methyl group, a trimethylsilyl group, a methyl group, an isopropyl group, a tert-butyl group and a phenyl group; a naphthyl group unsubstituted or substituted with deuterium; biphenyl group; phenanthrene group; anthracene group; tetrahydronaphthyl group unsubstituted or substituted with a methyl group; NRR'; And may be unsubstituted or substituted with one or more substituents selected from the group consisting of a combination thereof, wherein R and R' are the same as or different from each other, and each independently a methyl group or a phenyl group unsubstituted or substituted with a tert-butyl group ; biphenyl group; Or a tetrahydronaphthyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, R1 is hydrogen; a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted amine group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and the amine group is represented by NR"R"'.

According to an exemplary embodiment of the present specification, R1 is hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted isopropyl group; a substituted or unsubstituted n-butyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted cyclohexyl group; a substituted or unsubstituted adamantyl group; a substituted or unsubstituted hexahydrocarbazole group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted dihydrobenzoazacilline group; a substituted or unsubstituted phenoxazine group; a substituted or unsubstituted phenothiazine group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted tetrahydronaphthyl group; a substituted or unsubstituted decahydrobenzocarbazole group; or substituted or unsubstituted NR"R"', R" and R"' are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted fluorene group; Or a substituted or unsubstituted tetrahydronaphthyl group.

In R1, R" and R"', "substituted or unsubstituted" is deuterium; halogen group; cyano group; a linear or branched alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a linear or branched alkoxy group having 1 to 30 carbon atoms that is unsubstituted or substituted with a halogen group; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylsilyl group having 6 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium; a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

In R1, R" and R"', "substituted or unsubstituted" is deuterium; F; cyano group; methoxy group; trifluoromethyl group; trideuterium methyl group; trifluoromethoxy group; trimethylsilyl group; a triphenylsilyl group; dimethyl tert-butylsilyl group; a methyl group unsubstituted or substituted with deuterium; a cumyl group unsubstituted or substituted with deuterium; isopropyl group; tert-butyl group; a phenyl group unsubstituted or substituted with deuterium; a carbazole group unsubstituted or substituted with a tert-butyl group; And it means unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R1 is hydrogen; methyl group; ethyl group; isopropyl group; n-butyl group; tert-butyl group; cyclohexyl group; adamantyl group; hexahydrocarbazole group; a carbazole group; fluorene group; dihydroacridine group; dihydrobenzoazacillin group; phenoxazine; phenothiazine group; phenyl group; biphenyl group; naphthyl group; tetrahydronaphthyl group; decahydrobenzocarbazole group; or NR″R″′, R″ and R″′ are the same as or different from each other, and each independently a phenyl group; biphenyl group; dibenzofuran group; naphthyl group; dibenzothiophene group; fluorene group; Or a tetrahydronaphthyl group, wherein the substituent is deuterium; F; cyano group; methoxy group; trifluoromethyl group; trideuterium methyl group; trifluoromethoxy group; trimethylsilyl group; a triphenylsilyl group; dimethyl tert-butylsilyl group; a methyl group unsubstituted or substituted with deuterium; a cumyl group unsubstituted or substituted with deuterium; isopropyl group; tert-butyl group; a phenyl group unsubstituted or substituted with deuterium; a carbazole group unsubstituted or substituted with a tert-butyl group; And it may be unsubstituted or substituted with one or more substituents selected from the group consisting of combinations thereof.

The cumulus

means

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

In the compound, Ph represents a phenyl group, and D represents deuterium.

The present specification provides an organic light emitting device including the above-described compound.

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

In the present specification, when a part "includes" a certain component, this means that other components may be further included, rather than excluding other components, unless otherwise stated.

In the present specification, the 'layer' means compatible with the 'film' mainly used in the present technical field, and refers to a coating covering a desired area. The size of the 'layers' is not limited, and each 'layer' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.

In this specification, the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.

In this specification, the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers D, or iii) ) means all of which are included in one or more C-layers and one or more D-layers, respectively.

As used herein, "deuterated", "substituted with deuterium" or "deuterated" means that a hydrogen at a substitutable position of a compound is replaced with deuterium.

In the present specification, "X% substitution with deuterium", "X% deuterated", "degree of deuteration X%", or "deuterium substitution rate X%" means that X% of hydrogens at substitutable positions in the structure is deuterium. means that it has been For example, when the structure is dibenzofuran, the dibenzofuran is “25% substituted with deuterium”, the dibenzofuran is “25% deuterated”, the dibenzofuran is “25% deuterated”, or The "deuterium substitution rate of 25%" of the dibenzofuran means that two of 8 hydrogens at substitutable positions of the dibenzofuran are substituted with deuterium.

In the present specification, the degree of deuteration is nuclear magnetic resonance spectroscopy ( ¹ H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or MALDI-TOF MS (Matrix assisted laser desorption / ionization Time-of-Flight Mass Spectrometry) ) can be confirmed by a known method.

The present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound represented by Formula 1 above. do.

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

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

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a dopant of the emission layer.

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

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

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

In an exemplary embodiment of the present specification, the light emitting layer further includes a host compound, wherein at least one hydrogen at a substitutable position is substituted with deuterium in the host compound.

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

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

[Formula H]

In the formula (H),

L20 and L21 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,

Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R20 and R21 are the same as or different from each other, and each independently represent hydrogen; heavy hydrogen; 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 heterocyclic group,

r21 is an integer of 1 to 7, and when r21 is 2 or more, 2 or more R21 are the same as or different from each other.

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

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

In an exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.

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

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

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4cyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to 4cyclic heterocyclic group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and 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 anthracene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted phenalene group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted benzofluorene group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; a naphthyl group unsubstituted or substituted with deuterium; phenanthrene group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.

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

In an exemplary embodiment of the present specification, R 20 is hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R 20 is hydrogen; heavy hydrogen; fluorine; a substituted or unsubstituted C1-C10 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R 20 is hydrogen; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R 20 is hydrogen; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R 20 is hydrogen; a substituted or unsubstituted monocyclic to 4cyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to 4cyclic heterocyclic group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R 20 is hydrogen; 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 anthracene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted phenalene group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted benzofluorene group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.

In an exemplary embodiment of the present specification, R 20 is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R 20 is hydrogen; heavy hydrogen; a phenyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; biphenyl group; a naphthyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.

According to an exemplary embodiment of the present specification, R21 is hydrogen.

According to an exemplary embodiment of the present specification, R21 is deuterium.

In an exemplary embodiment of the present specification, when the compound represented by Formula H is substituted with deuterium, 30% or more of hydrogen at a substitutable position is substituted with deuterium. In another exemplary embodiment, in the structure of Formula H, 40% or more of hydrogen at a substitutable position is substituted with deuterium. In another exemplary embodiment, in the structure of Formula H, 60% or more of hydrogen at a substitutable position is substituted with deuterium.

In another exemplary embodiment, in the structure of Formula H, 80% or more of hydrogen at a substitutable position is substituted with deuterium. In another exemplary embodiment, in the structure of Formula H, hydrogen at a substitutable position is 100% substituted with deuterium.

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

According to an exemplary embodiment of the present specification, the compound represented by Formula H may be prepared by the following Formula 1, but is not limited thereto.

[General formula 1]

In the general formula 1,

Ar ₁ is the same as defined for -L20-Ar20 of Formula H,

Ar ₂ has the same definition as -L21-Ar21 of Formula H, and R20 and R21 may be further substituted in the anthracene core of Formula 1 above.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is used as a dopant in the emission layer, and the compound represented by Formula H is used as a host.

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

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

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

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes one or more dopants and a host.

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

According to an exemplary embodiment of the present specification, at least one of the two or more mixed dopants includes Formula 1, and the host includes a compound represented by Formula H. At least one of the two or more mixed dopants may include Chemical Formula 1, and for the rest, a dopant material known in the art may be used, but the present invention is not limited thereto.

According to an exemplary embodiment of the present specification, at least one of the two or more mixed dopants includes Formula 1, and the remainder uses at least one of a boron-based compound, a pyrene-based compound, and a delayed fluorescence-based compound different from Formula 1 However, the present invention is not limited thereto.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes at least one host.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes two or more types of mixed hosts.

According to an exemplary embodiment of the present specification, at least one of the two or more types of mixed hosts is a compound represented by Formula H.

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

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes two types of mixed hosts.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes two types of mixed hosts, the two types of mixed hosts are different from each other, and the two types of hosts are represented by Formula H is a compound that becomes

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the first host represented by the formula (H); and a second host represented by Formula H, wherein the first host and the second host are different from each other.

According to an exemplary embodiment of the present specification, the first host: the second host is included in a weight ratio of 95:5 to 5:95, preferably 70:30 to 30:70 by weight.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes at least one host and a dopant.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes at least one host and a dopant, the host includes a compound represented by Formula H, and the dopant includes the above formula The compound represented by 1 is included.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes two or more mixed hosts, and a dopant.

According to an exemplary embodiment of the present specification, at least one of the two or more mixed hosts includes the compound represented by Formula H, and the dopant includes the compound represented by Formula 1 above.

In the present specification, the two or more types of mixed hosts are different from each other.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes two types of mixed hosts, and a dopant.

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

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the first host represented by the formula (H); a second host represented by the formula (H); and a dopant represented by Formula 1, wherein the first host and the second host are different from each other. According to an exemplary embodiment of the present specification, the organic material layer uses at least one host and at least one dopant, , The at least one host includes a compound represented by Formula H, and the at least one dopant includes a compound represented by Formula 1 above.

According to an exemplary embodiment of the present specification, the organic material layer uses two or more types of mixed hosts, and two or more types of mixed dopants, and the two or more types of mixed hosts may use the same material as described above, and a mixture of the two or more types The dopant may use the same material as described above.

In an exemplary 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 two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes a compound represented by Formula 1 above.

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

In the exemplary embodiment of the present specification, the organic light emitting device may include two or more electron transport layers, but is not limited thereto.

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

In addition, in the exemplary embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other.

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

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

In addition, in an exemplary embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other. have.

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

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

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

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

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

For example, the structure of the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2 . 1 and 2 illustrate an organic light emitting device, but is not limited thereto.

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

2 is a substrate (1), a first electrode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), a first electron transport layer (8), the second An example of an organic light emitting device in which the electron transport layer 9 , the electron injection layer 10 , and the second electrode 4 are sequentially stacked is shown. In such a structure, the compound may be included in the light emitting layer 3 .

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Formula 1 above.

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. It may be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Laid-Open No. 2003/012890). However, the manufacturing method is not limited thereto.

As the material for the first electrode, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The second electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a _{multi-layered material such as LiO 2} /Al, but is not limited thereto.

The emission layer may include a host material and a dopant material. Examples of the host material include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

As the dopant material, when an additional compound is included in addition to the compound represented by Formula 1, there are an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

In the present specification, when the compound represented by Formula 1 is included in an organic material layer other than the light emitting layer or an additional light emitting layer is provided, the light emitting material of the light emitting layer receives and bonds holes and electrons from the hole transport layer and the electron transport layer, respectively. As a material capable of emitting light in the visible light region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; and rubrene, but is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole injection effect at the first electrode and an excellent hole injection effect on the light emitting layer or the light emitting material. Also, a material excellent in the ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; carbazole-based organics; nitrile-based organics; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic materials; Polythiophene-based conductive polymers such as anthraquinone and polyaniline or mixtures of two or more of the above examples, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material capable of transporting holes from the first electrode or the hole injection layer to the light emitting layer, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a carbazole-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material capable of well injecting electrons from the second electrode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes; triazine derivatives; LiQ, etc., but is not limited thereto. The electron transport layer may be used with any desired first electrode material, as used in accordance with the prior art. In particular, suitable first electrode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium, samarium, and the like, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from the electrode. It is preferable that the electron injection material has excellent electron transporting ability and has excellent electron injection effect from the second electrode and electron injection effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof, metal complex compounds and nitrogen-containing 5-membered ring derivatives, and mixtures of two or more of the above examples, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.

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

The hole blocking layer is a layer that blocks holes from reaching the cathode through the light emitting layer, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, but is not limited thereto.

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

In an exemplary embodiment of the present specification, the compound represented by 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 may act on a principle similar to that applied to an organic light emitting device in an organic light emitting device including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and the like. For example, the organic solar cell may have a structure including a negative electrode, a positive electrode, and a photoactive layer provided between the negative electrode and the positive electrode, and the photoactive layer may include the compound.

The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming one or more organic material layers using the above-described compound.

Hereinafter, in order to describe the present specification in detail, it will be described in detail with reference to Examples and Comparative Examples. However, the Examples and Comparative Examples according to the present specification may be modified in various other 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. Examples and comparative examples of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

Synthesis Example 1. Synthesis of compound A-2-1

In a three-necked flask, 1-bromo-3-chloro-5-methylbenzene (146 mmol, 30 g, 1eq.) and bis(4-(terbutyl)phenyl)amine (146 mmol, 41.1 g, 1eq.) were added Dissolve in toluene (0.2 M, 730 ml), sodium terbutoxide (219 mmol, 21 g, 1.5 eq.), bis (tri-tert-butylphosphine) palladium (0) (1.46 mmol, 0.75 g, 0.01 eq. ), and stirred for 1 hour under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, distilled water was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract _{was dried over MgSO 4} , concentrated, and the sample was purified by silica gel column chromatography to obtain Compound A-2-1, 49g. (Yield 83%, MS[M+H]+= 405)

Synthesis Example 2. Synthesis of compound A-2-2

5-terbutyl-[1,1'-biphenyl]-2-amine (66.6 mmol, 15 g, 1eq.) and 3-bromo-5,5,8,8-tetramethyl-5 in a 3-neck flask ,6,7,8-tetrahydronaphtho[2,3- b ]thiophene (66.6 mmol, 21.5 g, 1eq.) was dissolved in toluene (0.2 M, 335 ml) and sodium terbutoxide (99.9 mmol, 9.60) g, 1.5eq), bis(tri-terbutylphosphine)palladium(0) (0.666 mmol, 0.340 g, 0.01eq.) were added, and the mixture was stirred for 12 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, H ₂ O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract _{was dried over MgSO 4} , concentrated, and the sample was purified by silica gel column chromatography to obtain Compound A-2-2, 24.2 g. (Yield 78%, MS[M+H]+= 468)

Synthesis Example 3. Synthesis of compound A-2-3

Dissolve compound A-2-1 (49.3 mmol, 20 g, 1eq.) and compound A-2-2 (49.3 mmol, 23.0 g, 1eq.) in toluene (0.2 M, 250 ml) in a three-necked flask, sodium taboo Toxide (73.9 mmol, 7.10 g, 1.5eq.) and bis(tri-terbutylphosphine)palladium(0) (0.493 mmol, 0.252 g, 0.01eq.) were added, and then under reflux conditions under argon atmosphere for 12 hours. stirred. Upon completion of the reaction, after cooling to room temperature, H ₂ O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract _{was dried over MgSO 4} , concentrated, and the sample was purified by silica gel column chromatography to obtain Compound A-2-3, 36.1 g. (Yield 88%, MS[M+H]+= 837)

Synthesis Example 4. Synthesis of Compound A-2

In a three-necked flask, compound A-2-3 (43.1 mmol, 36.1 g, 1eq.) was dissolved in 1,2-dichlorobenzene (0.1 M, 430 ml) and borontriiodide (69.0 mmol, 27.0 g, 1.6eq.) .), and stirred for 3 hours at ^{140 o C in an argon atmosphere.} The reaction ^{mass was cooled to 0 o} C, and N,N-diisopropylethylamine (388 mmol, 50.2 g, 9eq.) was added thereto, followed by stirring for 1 hour. Extraction was performed in a separatory funnel using toluene and H _{2 O.} The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography, followed by sublimation purification to obtain Compound A-2, 7.1g. (yield 19%, MS[M+H]+= 603)

Synthesis Example 5. Synthesis of compound A-3-1

In Synthesis Example 2, compounds A-3-1 and 18.2 g were prepared in the same manner except that compounds S-4-1 (13g, 1eq.) and S-5 were used instead of compounds S-3 and S-4. got it (yield 95%, MS[M+H]+=476)

Synthesis Example 6. Synthesis of compound A-3-2

In Synthesis Example 3, compounds A-2-1 (15g. 1eq.) and A-3-1 were used instead of compounds A-2-1 and A-2-2, except that A-3-1 was prepared in the same manner as compound A- 3-2, 18.4 g was obtained. (yield 59%, MS[M+H]+= 845)

Synthesis Example 7. Synthesis of compound A-3

Compound A-3, 3.2 g was obtained in the same manner as in Synthesis Example 4, except that Compound A-3-2 (18.4 g. 1eq.) was used instead of Compound A-2-3. (yield 59%, MS[M+H]+=853)

Synthesis Example 8. Synthesis of compound A-7-1

Compounds A-7-1, 14.6g were obtained in the same manner as in Synthesis Example 2, except that compounds S-6 (13g, 1eq.) and S-7 were used instead of compounds S-3 and S-4. (Yield 62%, MS[M+H]+= 538)

Synthesis Example 9. Synthesis of compound A-7-2

Compound A-7 was prepared in the same manner as in Synthesis Example 3, except that compounds A-2-1 (10g. 1eq.) and A-7-1 were used instead of compounds A-2-1 and A-2-2. -2 16.5 g was obtained. (Yield 74%, MS[M+H]+=907)

Synthesis Example 10. Synthesis of Compound A-7

Compound A-7, 2.8 g was obtained in the same manner as in Synthesis Example 4, except that Compound A-7-2 (16.5 g. 1eq.) was used instead of Compound A-2-3. (Yield 17%, MS[M+H]+= 915)

Synthesis Example 11. Synthesis of compound A-1-1

Compound A-1-1, 29.4g was obtained in the same manner as in Synthesis Example 1, except that compound S-8 (g. 1eq.) was used instead of compound S-2. (yield 75%, MS[M+H]+=592)

Synthesis Example 12. Synthesis of compound A-1-2

Compound A-1-1 (29.4 g, 49.6 mmol, 1eq.), 4-(tert-butyl)aniline (7.78 g, 52.1 mmol, 1.05eq), Pd(Pt-Bu ₃ ) ₂ (0.25 g, 0.01eq) .), NaOt-Bu (7.2 g, 1.5eq.) was dissolved in toluene (250 ml) and stirred under reflux. Upon completion of the reaction, after cooling to room temperature, the reactant was transferred to a separatory funnel and extracted. After _{drying, filtration, and concentration with MgSO 4} , the next reaction proceeds without further purification.

Compound S-10 (11.1 g, 51.1 mmol, 1.5eq.), Pd(Pt-Bu ₃ ) ₂ (0.25 g, 0.1eq.), NaOt-Bu (7.2 g, 1.5eq.) in toluene (204 ml) It was dissolved under reflux and stirred. Upon completion of the reaction, after cooling to room temperature, the reactant was transferred to a separatory funnel and extracted. It _{was dried over MgSO 4} , filtered, concentrated, and purified by column chromatography to obtain compound A-1-2 (22.9 g, 55%).

MS:[M+H] ⁺ =837

Synthesis Example 13. Synthesis of Compound A-1

Compound A-1, 4.2g was obtained in the same manner as in Synthesis Example 4, except that Compound A-1-2 (15g. 1eq.) was used instead of Compound A-2-3. (Yield 28%, MS[M+H]+= 846)

Synthesis Example 14. Synthesis of Compound A-4-1

Compound A-4-1, 17.9 g, was obtained in the same manner as in Synthesis Example 1, except that compound S-11 (20.3 g. 1eq.) was used instead of compound S-2. (Yield 68%, MS[M+H]+=541)

Synthesis Example 14-1. Synthesis of compound A-4-2

Compound A-4-2, 15.5 g was obtained in the same manner as in Synthesis Example 2, except that compound S-9 (10 g, 1eq.) was used instead of compound S-3. (yield 59%, MS[M+H]+= 392)

Synthesis Example 15. Synthesis of compound A-4-3

Same as in Synthesis Example 3 except that compounds A-4-1 (16g. 1eq.) and A-4-2 (11.6g. 1eq.) were used instead of compounds A-2-1 and A-2-2 18.8 g of Compound A-4-3 was obtained. (Yield 71%, MS[M+H]+= 857)

Synthesis Example 16. Synthesis of Compound A-4

Compound A-4, 4.2g was obtained in the same manner as in Synthesis Example 4, except that Compound A-4-3 (18g. 1eq.) was used instead of Compound A-2-3. (Yield 23%, MS[M+H]+= 905)

Synthesis Example 17. Synthesis of compound A-5-1

Compound A-5-1, 18.5 g, was obtained in the same manner as in Synthesis Example 1, except that compound S-12 (18 g. 1eq.) and xylene instead of toluene were used instead of compound S-2. (Yield 77%, MS[M+H]+= 494)

Synthesis Example 18. Synthesis of compound A-5-2

Same as in Synthesis Example 3, except that compounds A-5-1 (9g. 1eq.) and A-4-2 (7.1g. 1eq.) were used instead of compounds A-2-1 and A-2-2 to obtain Compound A-5-2, 9.9 g. (Yield 64%, MS[M+H]+=849)

Synthesis Example 19. Synthesis of Compound A-5

Compound A-5 and 3.5 were obtained in the same manner as in Synthesis Example 4, except that Compound A-5-2 (9.9 g. 1eq.) was used instead of Compound A-2-3. (Yield 35%, MS[M+H]+= 857)

Synthesis Example 20. Synthesis of compound A-6-1

Compound A-6-1 and 124.1 g were obtained in the same manner as in Synthesis Example 1, except that compound S-13 (22.7 g. 1eq.) was used instead of compound S-2. (Yield 84%, MS[M+H]+=590)

Synthesis Example 21. Synthesis of compound A-6-2

In Synthesis Example 2, compounds A-6-2, 8.8 were prepared in the same manner except that compounds S-9 (8g, 1eq.) and S-14 (12.3g) were used instead of compounds S-3 and S-4. g was obtained. (Yield 55%, MS[M+H]+=299)

Synthesis Example 22. Synthesis of compound A-6-3

In Synthesis Example 3, compounds A-6-1 (12 g. 1eq.) and A-6-2 (6.1 g) were used instead of compounds A-2-1 and A-2-2, except that A-6-2 (6.1 g) was prepared in the same manner. 10.6 g of Compound A-6-3 was obtained. (Yield 61%, MS[M+H]+= 523)

Synthesis Example 23. Synthesis of Compound A-6

Compound A-6, 2.5 g was obtained in the same manner as in Synthesis Example 4, except that Compound A-6-3 (9.5 g. 1eq.) was used instead of Compound A-2-3. (Yield 26%, MS[M+H]+=861)

Synthesis Example 24. Synthesis of compound A-11-1

Compound A-11-1, 18.0 g was obtained in the same manner as in Synthesis Example 1, except that compound S-15 (18.6 g. 1eq.) was used instead of compound S-2. (Yield 77%, MS[M+H]+= 601)

Synthesis Example 25. Synthesis of compound A-11-2

Compounds A-11-2, 12.5 prepared in the same manner as in Synthesis Example 2, except that compounds S-16 (8g, 1eq.) and S-4 (12.7g) were used instead of compounds S-3 and S-4. g was obtained. (Yield 71%, MS[M+H]+= 446)

Synthesis Example 26. Synthesis of compound A-11

Prepared in the same manner except that in Synthesis Example 3, compounds A-11-1 (15.5 g. 1eq.) and A-11-2 (11.5 g) were used instead of compounds A-2-1 and A-2-2 Thus, 18.5 g of Compound A-11-3 was obtained. (Yield 71%, MS[M+H]+= 1010)

Compound A-11, 3.2 g, was obtained in the same manner as in Synthesis Example 4, except that Compound A-11-3 (14.5 g. 1eq.) was used instead of Compound A-2-3. (Yield 22%, MS[M+H]+= 1017)

Synthesis Example 27. Synthesis of compound A-13-1

Compound A-13-1, 13.5 g, was obtained in the same manner as in Synthesis Example 1, except that Compound S-17 (10g. 1eq.) was used instead of Compound S-1. (Yield 84%, MS[M+H]+= 526)

Synthesis Example 28. Synthesis of compound A-13-2

Compound A-13-2, 9.0 g, prepared in the same manner as in Synthesis Example 2, except that compounds S-19 (10 g, 1eq.) and S-18 (11.9 g) were used instead of compounds S-3 and S-4 got (Yield 49%, MS[M+H]+=422)

Synthesis Example 29. Synthesis of compound A-13

In Synthesis Example 3, compounds A-13-1 (10.2 g. 1eq.) and A-13-2 (8.2 g) were used instead of compounds A-2-1 and A-2-2, except that A-13-2 (8.2 g) was prepared in the same manner. Thus, 10.8 g of Compound A-13-3 was obtained. (Yield 61%, MS[M+H]+= 911)

Compound A-13, 1.9g was obtained in the same manner as in Synthesis Example 4, except that Compound A-13-3 (9.7g. 1eq.) was used instead of Compound A-2-3. (yield 19%, MS[M+H]+= 919)

Synthesis Example 30. Synthesis of compound A-12-1

Compounds A-12-1 and 35.5 were prepared in the same manner as in Synthesis Example 1, except that compounds S-21 (20g. 1eq.) and S-20 (31.5g) were used instead of compounds S-1 and S-2. g was obtained. (yield 79%, MS[M+H]+= 556)

Synthesis Example 31. Synthesis of compound A-12

Compounds prepared in the same manner as in Synthesis Example 3 except that compounds A-12-1 (10g. 1eq.) and A-11-2 (8g) were used instead of compounds A-2-1 and A-2-2 A-12-2 11.8 g was obtained. (Yield 68%, MS[M+H]+=966)

Compound A-12, 3.9g, was obtained in the same manner as in Synthesis Example 4, except that Compound A-12-2 (10g. 1eq.) was used instead of Compound A-2-3. (Yield 39%, MS[M+H]+=973)

Synthesis Example 32. Synthesis of compound A-8-1

In Synthesis Example 1, the following reaction was carried out without further purification except that compounds S-22 (20g. 1eq.) and S-2 (27.1g) were used instead of compounds S-1 and S-2. do.

The unrefined reaction product is dissolved in tetrahydrofuran (THF) (240 mL), and then 17.3 g (1.3 eq.) of potassium carbonate is dissolved in 80 mL of water and slowly added. 43.7 g (1.5 eq.) of perfluorobutanesulfonyl fluoride was added and stirred at room temperature for 2 hours. After the reaction was completed, water and ethyl acetate were added to separate the mixture, followed by MgSO ₄ (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by column chromatography to obtain Compound A-8-1, 44.7 g. (Yield 67%)

Synthesis Example 33. Synthesis of compound A-8-2

Compound A-8-1 (12 g, 17.4 mmol, 1eq.), A-4-2 (7.2 g, 1.05 eq.), Palladium(0) bis(dibenzylideneacetone) (Pd(dba) ₂ ) (0.1 g, 0.01 eq/), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) (0.17 g, 0.02eq.), Cs ₂ CO ₃ (17 g, 3eq.) and xylene (90 ml) Heat at 140° C. and stir for 12 hours. The reaction solution was cooled to room temperature, and sat. After separation by adding aq.NH ₄ Cl and toluene, the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography (ethylacetate/hexane) gave compound A-8-2, 9.8 g. (Yield 72%, MS[M+H]+=781)

Synthesis Example 34. Synthesis of compound A-8-3

Compound A-8-3, 4.0g, was obtained in the same manner as in Synthesis Example 4, except that Compound A-8-2 (9.7g. 1eq.) was used instead of Compound A-2-3. (Yield 42%, MS[M+H]+=775)

Synthesis Example 35. Synthesis of compound A-8

In the same manner as in Synthesis Example 3, except that compounds A-8-3 (4g. 1eq.) and S-23 (1.5g, 1.2eq.) were used instead of compounds A-2-1 and A-2-2 prepared to obtain Compound A-8, 3.8 g. (Yield 74%, MS[M+H]+=995)

Synthesis Example 36. Synthesis of compound A-9-2

Compound A-9-1, 40.6 g was obtained in the same manner as in Synthesis Example 32, except that Compound S-24 (27.1 g. 1eq.) was used instead of Compound S-2. (Yield 71%)

In Synthesis Example 33, compound A-9-2, 11.6 g, was obtained in the same manner except that compound A-9-1 (15 g, 1eq.) was used instead of compound A-8-1. (Yield 68%, MS[M+H]+=781)

Synthesis Example 37. Synthesis of Compound A-9

Except for using Compound A-9-2 (10.5 g. 1eq.) instead of Compound A-2-3 in Synthesis Example 4, it was prepared in the same manner to obtain Compound A-9-3, 4.2 g. (Yield 40%, MS[M+H]+=775)

Compounds prepared in the same manner as in Synthesis Example 3 except that compounds A-9-3 (4.2 g. 1eq.) and S-25 (1.3 g) were used instead of compounds A-2-1 and A-2-2 A-9, 3.4 g was obtained. (Yield 66%, MS[M+H]+=955)

Synthesis Example 38. Synthesis of compound A-10-2

Compound A-10-1, 51g was obtained in the same manner as in Synthesis Example 32, except that Compound S-20 (37.6g. 1eq.) was used instead of Compound S-2. (Yield 66%)

Compound A-10-2, 8.4 g was obtained in the same manner as in Synthesis Example 33, except that Compound A-10-1 (13 g, 1eq.) was used instead of Compound A-8-1. (Yield 66%, MS[M+H]+=779)

Synthesis Example 39. Synthesis of Compound A-10

Compound A-10-3, 3.5 g was obtained in the same manner as in Synthesis Example 4, except that Compound A-10-2 (8.3 g. 1eq.) was used instead of Compound A-2-3. (Yield 42%, MS[M+H]+=787)

Compounds prepared in the same manner as in Synthesis Example 3 except that compounds A-10-3 (3.5 g. 1eq.) and S-27 (1.7 g) were used instead of compounds A-2-1 and A-2-2 A-10, 3.7 g was obtained. (yield 77%, MS[M+H]+= 1073)

Synthesis Example 40. Synthesis of compound A-14-1

Compound A-14-1, 12.4 g, was obtained in the same manner as in Synthesis Example 1, except that Compound S-28 was used instead of Compound S-2. (yield 59%, MS[M+H]+= 515)

Synthesis Example 40-1. Synthesis of compound A-14-2

In Synthesis Example 12, compounds A-14-1 (12.4 g, 1eq), S-29 and S-4 were used instead of compounds A-1-1, S-9 and S-10. Compound A-14-3, 10.8 g was obtained (yield 42%, MS[M+H]+=1070)

Synthesis Example 41. Synthesis of compound A-14

In Synthesis Example 4, compound A-14, 2.6 g was obtained in the same manner as in Synthesis Example 4, except that Compound A-14-3 (10.8 g. 1eq.) was used instead of Compound A-2-3. (yield 24%, MS[M+H]+= 1078)

Synthesis Example 42. Synthesis of compound A-15-1

In Synthesis Example 1, compounds A-15-1, 20.1 g were prepared in the same manner except that compounds S-30 and 1-bromo-3-chloro-5-fluorobenzene were used instead of compounds S-2 and S-1. got it (Yield 68%, MS[M+H]+= 519)

Synthesis Example 43. Synthesis of compound A-15-3

Compound A-15-1 (15g, 1eq), 4-(tert-butyl)-2-methylaniline and 3-bromo-5- instead of compound A-1-1, S-9 and S-10 in Synthesis Example 12 Compound A-15-3, 11.2 g, was obtained in the same manner except that methylbenzo[b]thiophene was used (yield 49%, MS[M+H]+=792)

Synthesis Example 44. Synthesis of compound A-15

Compound A-15, 1.8 g, was obtained in the same manner as in Synthesis Example 4, except that Compound A-15-3 (10 g. 1eq.) was used instead of Compound A-2-3. (Yield 18%, MS[M+H]+=799)

Synthesis Example 45. Synthesis of compound A-16-1

Compound A-16-1, 18.7 g, was obtained in the same manner as in Synthesis Example 33, except that the compound diphenylamine was used instead of the compound A-4-2. (Yield 73%, MS[M+H]+=559)

Synthesis Example 46. Synthesis of compound A-16-3

In Synthesis Example 12, compounds A-16-1 (16g, 1eq), dibenzo[b,d]furan-1-amine and S-4 were used instead of compounds A-1-1, S-9 and S-10. Except for the same preparation, compound A-16-3, 15.7 g, was obtained (yield 58%, MS[M+H]+=949)

Synthesis Example 47. Synthesis of compound A-16

Compound A-16, 2.1g, was obtained in the same manner as in Synthesis Example 4, except that Compound A-16-3 (10g. 1eq.) was used instead of Compound A-2-3. (Yield 21%, MS[M+H]+=957)

Synthesis Example 48. Synthesis of compound B-1-1

In a 3-necked flask, 1-bromo-3-chloro-5-terbutylbenzene (121 mmol, 30 g) and 4-terbutyl-N-(4-terbutylphenyl)-2,6-dimethylaniline (121 mmol) , 37.5 g) was dissolved in toluene (0.2 M, 605 ml), sodium terbutoxide (182 mmol, 17.5 g), bis (tri-terbutylphosphine) palladium (0) (1.2 mmol, 0.62 g) was added. , and stirred for 4 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, H ₂ O was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract _{was dried over MgSO 4} , concentrated, and the sample was purified by silica gel column chromatography to obtain compound B-1-1, 51.2 g. (yield 89%, MS[M+H]+=476)

Synthesis Example 49. Synthesis of compound B-1-2

In a three-neck flask, compound S-31 (97.6 mmol, 30 g) and 4-terbutylaniline (97.6 mmol, 14.6 g) were dissolved in toluene (0.2 M, 488 ml), and sodium terbutoxide (146.5 mmol, 14.1 g) , bis(tri-terbutylphosphine)palladium(0) (0.98 mmol, 0.5 g) was added, and the mixture was stirred for 6 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, H 2 O was added and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to obtain Compound B-1-2, 35.4 g. (yield 97%, MS[M+H]+=376)

Synthesis Example 50. Synthesis of compound B-1-3

In a three-necked flask, compound B-1-1 (44.1 mmol, 21 g) and compound B-1-2 (44.1 mmol, 16.6 g) were dissolved in toluene (0.2 M, 220 ml), and sodium terbutoxide (66.2 mmol, 6.4 g) and bis(tri-terbutylphosphine)palladium(0) (0.44 mmol, 0.23 g) were added thereto, and the mixture was stirred for 6 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, H 2 O was added and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to obtain Compound B-1-3, 21.8 g. (Yield 61%, MS[M+H]+= 815)

Synthesis Example 51. Synthesis of Compound B-1

In Synthesis Example 4, compound B-1-3 (21.8 g. 1eq.) was used instead of compound A-2-3, and the same preparation was performed except that the mixture was stirred at 140° C. to obtain compound B-1, 5.3 g. (Yield 21%, MS[M+H]+=957)

Synthesis Example 52. Synthesis of compound B-8-1

Compound B-8-1 19.4 prepared in the same manner as in Synthesis Example 1, except that compound 3-bromo-4'-terbutyl-5-chloro-1,1'-biphenyl was used instead of compound S-1 g was obtained. (yield 80%, MS[M+H]+= 524)

Synthesis Example 53. Synthesis of compound B-8-2

Compound B-8-2, 20.6 g, was obtained in the same manner as in Synthesis Example 49, except that compound S-32 was used instead of compound S-31. (Yield 70%, MS[M+H]+=376)

Synthesis Example 54. Synthesis of compound B-8

In Synthesis Example 3, compounds B-8-1 (19.4 g. 1eq.) and B-8-2 were used instead of compounds A-2-1 and A-2-2 in the same preparation as compound B- 8-3 22 g were obtained. (yield 69%, MS[M+H]+=863)

Compound B-8, 4.8 g, was obtained in the same manner as in Synthesis Example 51, except that Compound B-8-3 (11 g. 1eq.) was used instead of Compound B-1-3. (Yield 22%, MS[M+H]+=871)

Synthesis Example 55. Synthesis of compound B-9-1

Compound B-9-1, 24.5 g, was obtained in the same manner as in Synthesis Example 1, except that compound S-33 was used instead of compound S-2. (Yield 94%, MS[M+H]+= 543)

Synthesis Example 56. Synthesis of compound B-9-2

Compound B-9-2, 11.2 g, was obtained in the same manner as in Synthesis Example 49, except that Compound S-34 was used instead of Compound S-31. (Yield 88%, MS[M+H]+= 331)

Synthesis Example 57. Synthesis of compound B-9-3

Compound B-9 was prepared in the same manner as in Synthesis Example 3, except that compounds B-9-1 (18g. 1eq.) and B-8-2 were used instead of compounds A-2-1 and A-2-2. -3, 21.2 g were obtained. (Yield 77%, MS[M+H]+= 832)

Synthesis Example 58. Synthesis of compound B-9

Compound B-9, 3.8 g, was obtained in the same manner as in Synthesis Example 51, except that Compound B-9-3 (11 g. 1eq.) was used instead of Compound B-1-3. (yield 19%, MS[M+H]+= 859)

Synthesis Example 59. Synthesis of compound B-2-1

Compound B-2-1, 15.2 g, was obtained in the same manner as in Synthesis Example 1, except that compound S-27 was used instead of compound S-2. (Yield 88%, MS[M+H]+= 446)

Synthesis Example 60. Synthesis of compound B-2

Compound B-2-2, 12.2 g, prepared in the same manner as in Synthesis Example 12, except that compounds B-2-1 (15 g, 1eq) and S-35 were used instead of compounds A-1-1 and S-10 was obtained (yield 47%, MS [M + H] + = 783)

Compound B-2, 3.5g was obtained in the same manner as in Synthesis Example 51, except that Compound B-2-2 (9g. 1eq.) was used instead of Compound B-1-3. (Yield 38%, MS[M+H]+=791)

Synthesis Example 61. Synthesis of compound B-3-1

Compound B-3-1, 11.1 g, was obtained in the same manner as in Synthesis Example 1, except that compound S-36 was used instead of compound S-2. (Yield 78%, MS[M+H]+=520)

Synthesis Example 62. Synthesis of compound B-3

Prepared in the same manner except for using Compound B-3-1 (10g, 1eq), S-37 and S-10-1 instead of Compound A-1-1, S-9 and S-10 in Synthesis Example 12 to obtain compound B-3-2, 8.7 g (yield 56%, MS[M+H]+=806)

Compound B-3, 2.3 g was obtained in the same manner as in Synthesis Example 51, except that Compound B-3-2 (8.7 g. 1eq.) was used instead of Compound B-1-3. (Yield 26%, MS[M+H]+= 813)

Synthesis Example 63. Synthesis of compound B-4-1

Compound B-4-1, 16.3 g, was obtained in the same manner as in Synthesis Example 1, except that compound S-38 was used instead of compound S-2. (Yield 73%, MS[M+H]+= 524)

Synthesis Example 64. Synthesis of compound B-4

Compounds prepared in the same manner as in Synthesis Example 12, except that compounds B-4-1 (14g, 1eq), S-39 and S-31 were used instead of compounds A-1-1, S-9 and S-10 B-4-2, 12.8 g was obtained (yield 52%, MS[M+H]+=918)

Compound B-4, 2.8 g, was obtained in the same manner as in Synthesis Example 51, except that Compound B-4-2 (11 g. 1eq.) was used instead of Compound B-1-3. (Yield 25%, MS[M+H]+= 926)

Synthesis Example 65. Synthesis of compound B-5-1

Compound B-5-1, 17.8 g, was obtained in the same manner as in Synthesis Example 1, except that compound S-40 was used instead of compound S-2. (Yield 65%, MS[M+H]+= 612)

Synthesis Example 66. Synthesis of compound B-5

Compounds prepared in the same manner as in Synthesis Example 12, except that compounds B-5-1 (17g, 1eq), S-41 and S-31 were used instead of compounds A-1-1, S-9 and S-10 B-5-2, 12.7 g was obtained (yield 47%, MS[M+H]+=972)

Compound B-5, 2.2 g, was obtained in the same manner as in Synthesis Example 51, except that Compound B-5-2 (11.7 g. 1eq.) was used instead of Compound B-1-3. (Yield 19%, MS[M+H]+=980)

Synthesis Example 67. Synthesis of compound B-6-1

Compound B-6-1, 13.2 g, was obtained in the same manner as in Synthesis Example 1, except that compound S-42 was used instead of compound S-2. (Yield 82%, MS[M+H]+= 545)

Synthesis Example 68. Synthesis of compound B-6

Compound B-6-2, 11.8 g in the same manner as in Synthesis Example 12, except that compounds B-6-1 (12 g, 1eq) and S-31 were used instead of compounds A-1-1 and S-10 was obtained (yield 61%, MS [M + H] + = 885)

Compound B-6, 2.7 g was obtained in the same manner as in Synthesis Example 51, except that Compound B-6-2 (11.7 g. 1eq.) was used instead of Compound B-1-3. (yield 24%, MS[M+H]+= 893)

Synthesis Example 69. Synthesis of compound B-7-1

Compound B-7-1, 19.1 g, was obtained in the same manner as in Synthesis Example 32, except that compound S-43 was used instead of compound S-2. (yield 79%)

Synthesis Example 70. Synthesis of compound B-7-2

Compound B-7-2, 10.7 g, was obtained in the same manner as in Synthesis Example 33, except that Compound B-7-1 (18 g, 1eq.) was used instead of Compound A-8-1. (Yield 72%, MS[M+H]+=609)

Synthesis Example 71. Synthesis of compound B-7

In Synthesis Example 12, compounds B-7-2 and 7.8 were prepared in the same manner except that compounds B-7-2 (10.7 g, 1eq) and S-31 were used instead of compounds A-1-1 and S-10. g (yield 47%, MS[M+H]+=949)

Compound B-7, 1.7 g was obtained in the same manner as in Synthesis Example 51, except that Compound B-7-2 (7.8 g. 1eq.) was used instead of Compound B-1-3. (Yield 21%, MS[M+H]+=957)

Synthesis Example 72. Synthesis of compound A-17

In the same manner as in Synthesis Example 3, except that compounds A-8-3 (2g. 1eq.) and S-44 (0.6g, 1.2eq.) were used instead of compounds A-2-1 and A-2-2 prepared to obtain Compound A-17, 1.9 g. (Yield 78%, MS[M+H]+=937)

Synthesis Example 73. Synthesis of compound A-18-1

In Synthesis Example 1, compounds A-18-1 and 37.2 g were prepared in the same manner except that compounds S-1-1 (20g. 1eq.) and S-20 were used instead of compounds S-1 and S-2. got it (yield 75%, MS[M+H]+= 517)

Synthesis Example 74. Synthesis of compound A-18

9.7 g of compound A-18-2 was prepared in the same manner as in Synthesis Example 12, except that compounds A-18-1 (g, 1eq) and S-4 were used instead of compounds A-1-1 and S-10 obtained (yield 58%, MS[M+H]+=873)

In Synthesis Example 51, the compound A-18, 2.2g was obtained in the same manner except that Compound A-18-2 (6.5 g. 1eq.) was used instead of Compound B-1-3. (Yield 33%, MS[M+H]+= 881)

Synthesis Example 75. Synthesis of compound A-19-1

Compound A-19-1, 20.5 g was obtained in the same manner as in Synthesis Example 1, except that Compound S-20 (19g) was used instead of Compound S-2. (Yield 82%, MS[M+H]+= 514)

Synthesis Example 76. Synthesis of compound A-19

Compound A was prepared in the same manner as in Synthesis Example 3, except that Compound A-12-1 (10 g. 1eq.) and S-45 (6.6 g) were used instead of Compound A-2-1 and A-2-2 -19-2 8.9 g was obtained. (Yield 56%, MS[M+H]+= 816)

In Synthesis Example 4, Compound A-19, 4.0g, was obtained in the same manner except that Compound A-19-2 (8g. 1eq.) was used instead of Compound A-2-3. (Yield 31%, MS[M+H]+= 824)

Synthesis Example 77. Synthesis of compound A-20-1

Compounds prepared in the same manner as in Synthesis Example 3 except that compounds A-6-1 (8g. 1eq.) and A-11-2 (6g) were used instead of compounds A-2-1 and A-2-2 A-20-1, 8 g was obtained. (yield 59%, MS[M+H]+= 1000)

Synthesis Example 78. Synthesis of compound A-20

Compound A-20, 2.7g was obtained in the same manner as in Synthesis Example 4, except that Compound A-20-1 (8g. 1eq.) was used instead of Compound A-2-3. (Yield 33%, MS[M+H]+= 1008)

Synthesis Example 79. Synthesis of compound A-21-1

Compound A-10-1 (8.5 g, 1eq.) instead of Compound A-8-1 in Synthesis Example 33, and A-11-2 instead of A-4-2 were prepared in the same manner as Compound A- 21-1, 7.1 g were obtained. (Yield 71%, MS[M+H]+=944)

Synthesis Example 80. Synthesis of compound A-21-2

Except for using Compound A-21-1 (6.5 g. 1eq.) instead of Compound A-2-3 in Synthesis Example 4, it was prepared in the same manner to obtain Compound A-21-2, 2.9 g. (Yield 45%, MS[M+H]+= 952)

Synthesis Example 81. Synthesis of compound A-21

Intermediate A-21-2 2.9 g (1 eq.), A-21-3 0.82 g (1.5 eq), Cs ₂ CO ₃ 2.9 g (3 eq), bis (tri-tert-butylphosphine) palladium under nitrogen atmosphere (0) 0.03 (0.02eq.) was added to 30l of toluene, and the mixture was stirred under reflux for 4 hours. After completion of the reaction, extraction was performed, and compound A-21, 1.9 g, was obtained through recrystallization. (Yield 62%). MS[M+H]+ = 1036

Synthesis Example 82. Synthesis of compound A-22-1

Compound A-22-1, 22.8g was obtained in the same manner as in Synthesis Example 32, except that Compound S-47 (18.9 g) was used instead of Compound S-2. (yield 59%)

Synthesis Example 83. Synthesis of compound A-22-3

In Synthesis Example 33, Compound A-22-1 (15g, 1eq.) was used instead of Compound A-8-1 to obtain Compound A-22-2, 10.2g. (Yield 61%, MS[M+H]+=892)

Except for using Compound A-22-2 (9g. 1eq.) instead of Compound A-2-3 in Synthesis Example 4, it was prepared in the same manner to obtain Compound A-22-3, 4.5g. (Yield 50%, MS[M+H]+= 900)

Synthesis Example 84. Synthesis of compound A-22

Compound A-22, 2.9g was obtained in the same manner as in Synthesis Example 81, except that Compound A-22-3 (4g, 1eq.) was used instead of Compound A-21-2. (Yield 62%, MS[M+H]+=1067)

Synthesis Example 85. Synthesis of compound A-23-2

Compound A-23-1, 18.2g was obtained in the same manner as in Synthesis Example 1, except that Compound S-49 (10g) instead of Compound S-1 and Compound S-50 instead of S-2 were used. (Yield 76%, MS[M+H]+= 558)

Compound A-23 was prepared in the same manner as in Synthesis Example 3, except that compounds A-23-1 (15 g. 1eq.) and A-11-2 were used instead of compounds A-2-1 and A-2-2. -2, 17.7 g was obtained. (Yield 68%, MS[M+H]+=968)

Synthesis Example 86. Synthesis of compound A-23

Compound A-23, 3.3g was obtained in the same manner as in Synthesis Example 4, except that Compound A-23-2 (10g. 1eq.) was used instead of Compound A-2-3. (Yield 33%, MS[M+H]+=975)

Synthesis Example 87. Synthesis of compound A-24-2

Compound A-24-1, 22.9g was obtained in the same manner as in Synthesis Example 32, except that Compound S-51 (g) was used instead of Compound S-2. (Yield 64%)

Compound A-24 was prepared in the same manner as in Synthesis Example 33, except for using Compound A-24-1 (20g, 1eq.) instead of Compound A-8-1 and A-11-2 instead of A-4-2 -2, 15 g were obtained. (Yield 63%, MS[M+H]+=890)

Synthesis Example 88. Synthesis of compound A-24

Except for using Compound A-24-2 (13g. 1eq.) instead of Compound A-2-3 in Synthesis Example 4, it was prepared in the same manner to obtain Compound A-24-3, 5.6g. (Yield 43%, MS[M+H]+=897)

Compound A-24, 3.4g was prepared in the same manner as in Synthesis Example 3, except that Compound A-24-3 (5g. 1eq.) and diphenylamine were used instead of Compounds A-2-1 and A-2-2 got it (yield 59%, MS[M+H]+=1031)

Example 1

A system including compounds BD-1 and BH-B in a weight ratio of 5:95 was implemented. Specifically, using the OPLS3e force field, 300 molecules (BH-B 95%, A-1 5% ratio), temperature 300K, simulation time 3ns, NVT and 30ns NPT calculation The environment of the doped device was realized computationally and chemically by calculating Molecular Dynamics through The implemented molecular model is shown in FIG. 8 .

At this time, the volume and density of all molecules and the average distance between different molecules were obtained by calculation. The results are shown in Table 1 below.

Examples 2 to 5

A molecular system was calculated in the same manner as in Example 1, except that the dopant shown in Table 1 was used instead of Compound A-1 in Example 1.

Comparative Examples 1 to 4

Specifically, the molecular models implemented by Examples 1 to 5 and Comparative Examples 1 to 3 are shown in FIGS. 4 to 12 .

Specifically, FIG. 4 is a view showing a molecular model implemented by simulation of the X-1 and BH-B systems of Comparative Example 1. Referring to FIG.

5 is a view showing a molecular model implemented by simulation of the X-2 and BH-B systems of Comparative Example 2.

6 is a view showing a molecular model implemented by simulation of the X-3 and BH-B systems of Comparative Example 3.

7 is a view showing a molecular model implemented by simulation of the X-4 and BH-B systems of Comparative Example 4;

8 is a diagram illustrating a molecular model implemented by simulation of the BD-1 and BH-B systems of Example 1. FIG.

9 is a diagram illustrating a molecular model implemented by simulation of the BD-2 and BH-B systems of Example 2. FIG.

10 is a view showing a molecular model implemented by simulation of the BD-3 and BH-B systems of Example 3;

11 is a diagram illustrating a molecular model implemented by simulation of the BD-4 and BH-B systems of Example 4;

12 is a view showing a molecular model implemented by simulation of the BD-5 and BH-B systems of Example 5;

entryentry	시스템system	전체 부피 (cm ³)total volume (cm ³ )	전체 밀도 (g/ cm ³)overall density (g/cm ³ )	분자간 거리 (Å)intermolecular distance (Å)
비교예 1Comparative Example 1	X-1 와 BH-B 시스템X-1 and BH-B systems	193.60 × 10 ^-27 193.60 × 10 ^-27	1.1071.107	7.17.1
비교예 2Comparative Example 2	X-2 와 BH-B 시스템X-2 and BH-B systems	196.32 × 10 ^-27 196.32 × 10 ^-27	1.1071.107	14.7514.75
비교예 3Comparative Example 3	X-3 와 BH-B 시스템X-3 and BH-B systems	195.07 × 10 ^-27 195.07 × 10 ^-27	1.1071.107	14.8814.88
비교예 4Comparative Example 4	X-4 와 BH-B 시스템X-4 and BH-B systems	202.66 × 10 ^-27 202.66 × 10 ^-27	1.0931.093	15.1015.10
실시예 1Example 1	BD-1 와 BH-B 시스템BD-1 and BH-B systems	198.49 × 10 ^-27 198.49 × 10 ^-27	1.1021.102	14.9514.95
실시예 2Example 2	BD-2 와 BH-B 시스템BD-2 and BH-B systems	203.71 × 10 ^-27 203.71 × 10 ^-27	1.0941.094	15.1515.15
실시예 3Example 3	BD-3 와 BH-B 시스템BD-3 and BH-B systems	203.84 × 10 ^-27 203.84 × 10 ^-27	1.0941.094	15.1915.19
실시예 4Example 4	BD-4 와 BH-B 시스템BD-4 and BH-B systems	208.18 × 10 ^-27 208.18 × 10 ^-27	1.0901.090	15.2615.26
실시예 5Example 5	BD-5 와 BH-B 시스템BD-5 and BH-B systems	208.14 × 10 ^-27 208.14 × 10 ^-27	1.0891.089	15.3915.39

In Table 1 and FIGS. 4 to 12, the distance between the host and the dopant in Example 1, which is a system in which compound BD-1 containing an aliphatic hydrocarbon condensed ring substituted with an alkyl group is a dopant and BH-B as a host, is Compound X It was confirmed that -1 and BH-B were 2.1 times farther apart than in the system, and when comparing Comparative Examples 3 and 1, the compound containing the aliphatic hydrocarbon condensed ring substituted with an alkyl group was intermolecular in the molecular model with the host. It could be seen that the distance increased. In addition, even when compared with the system of Compound X-4 in which all tert-butyl groups are substituted in the compound, it was confirmed that the distance between the host and the dopant increased as the aliphatic hydrocarbon condensed ring substituted with an alkyl group was introduced. Therefore, if a device is manufactured by introducing a dopant in the light emitting layer with a compound according to an exemplary embodiment of the present specification including at least one aliphatic hydrocarbon condensed ring group substituted with an alkyl group, Dexter energy transfer with the triplet energy of the host occurs less Therefore, it could be expected that the device efficiency would increase.

Examples 6 and 7 and Comparative Examples 5 to 7

The maximum emission wavelengths of the compounds of Table 2 were measured and described in Table 2 below, and the measuring equipment used to measure them is a JASCO FP-8600 fluorescence spectrophotometer.

The maximum emission wavelength of the compound of Table 2 in the solution state can be obtained as follows. Prepare a sample for measurement by dissolving each compound to be measured at a concentration of 1 μM (microM) using toluene as a solvent. The sample solution is placed in a quartz cell and _{degassed using nitrogen gas (N 2} ) to remove oxygen in the solution, and then the fluorescence spectrum is measured at room temperature (300K) using a measuring device. At this time, the wavelength value (nm) of the maximum emission peak can be obtained.

The maximum emission wavelength in the film state of the compound can be obtained as follows. The host compound BH-1 and the dopant compound of Table 2 below were vacuum-deposited at a weight ratio of 98:2 on a glass substrate to prepare a light emitting layer film having a thickness of 1000 Å. In the above process, the deposition rate of organic material was maintained at 0.1 nm/sec. The produced film was measured for fluorescence spectrum at room temperature (300K) using a measuring device. At this time, the wavelength value (nm) of the maximum emission peak can be obtained, and a measurement graph is shown in FIG. 3 .

entryentry	화합물compound	용액 상태solution state		필름 상태film condition	(film-solution)(film-solution)
entryentry	화합물compound	최대발광파장 (nm)maximum emission wavelength (nm)	CIEyCIEy	최대발광파장 (nm)maximum emission wavelength (nm)	(film-solution)(film-solution)
비교예 5Comparative Example 5	X-4X-4	456456	0.10430.1043	460460	44
비교예 6Comparative Example 6	X-5X-5	463463	0.17770.1777	466466	33
비교예 7Comparative Example 7	X-6X-6	456456	0.08590.0859	460460	44
실시예 6Example 6	BD-6BD-6	456456	0.10170.1017	458458	22
실시예 7Example 7	BD-7BD-7	457457	0.10490.1049	459459	22

Comparing the emission spectra of the compounds X-4, X-5 and X-6 in the solution state in Table 2 and FIG. 3, each time the heterocycle increases by one in the compound based on the compound X-6, the main peak (main peak), it was confirmed that the intensity of the second peak formed in the longer wavelength band was increased. When looking at the CIEy value indicating color purity, the value of compound X-5 with the largest second peak was the largest. However, it was confirmed that compound BD-6 represented by Formula 1 of the present specification has the same maximum emission wavelength value in solution state as compound X-4, but color purity (CIEy) is more improved than that of X-4. , the compound of Formula 1 according to an exemplary embodiment of the present specification, that is, BD-6 and BD-7, which are compounds including at least one condensed aliphatic hydrocarbon ring substituted with an alkyl group, does not contain an aliphatic hydrocarbon condensed ring substituted with an alkyl group Comparing the maximum emission wavelength value in the film state of compound X-4, which is not, it was observed that when an aliphatic hydrocarbon condensed ring substituted with an alkyl group was introduced, the wavelength was shorter than that in the case where it was not. This is because the intermolecular interaction between the host and the dopant is minimized as shown in the simulation results of Experimental Example 1. Therefore, the compound of Formula 1 of the present specification can implement a device with high color purity and high efficiency in an organic light emitting device.

Example 8

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,400 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of the following HI-A and LG-101 to a thickness of 650 Å and 50 Å, respectively, on the ITO transparent electrode prepared as described above. On the hole injection layer, the following HT-A was vacuum deposited to a thickness of 600 Å to form a hole transport layer. On the hole transport layer, the following HT-B was vacuum deposited to a thickness of 50 Å to form an electron blocking layer. Then, on the electron blocking layer, 4 parts by weight of the following compound A-1 as a blue light emitting dopant and 100 parts by weight of the light emitting layer were vacuum deposited with the following BH-A as a host to a thickness of 200 Å to form a light emitting layer. Then, 50 Å of the following compound ET-A was vacuum-deposited as a first electron transport layer on the light emitting layer, followed by vacuum deposition of ET-B and LiQ in a 1:1 weight ratio to form a second electron transport layer to a thickness of 360 Å. On the second electron transport layer, LiQ was vacuum-deposited to a thickness of 5 Å to form an electron injection layer. On the electron injection layer, aluminum and silver were deposited to a thickness of 220 Å in a weight ratio of 10:1, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.9 Å/sec, the deposition rate of the aluminum of the cathode was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 × 10 ^-7 ~ 5 × 10 ^-8 torr to manufacture an organic light emitting device.

Examples 9 to 32 and Comparative Examples 8 to 11

Example 8 and Example 8 except that in Example 8, the compound shown in Table 3 was used instead of Compound A-1 as the dopant of the light emitting layer, and the compound shown in Table 3 was used instead of BH-A as the host material. Using the same method, the organic light emitting devices of Examples 9 to 32 and Comparative Examples 8 to 11 were respectively manufactured.

Voltage, conversion efficiency (cd/A/y) and 20 mA/cm ² of ^{applying a current density of 10 mA/cm 2} to the organic light emitting devices of Examples 8 to 32 and Comparative Examples 8 to 11 _{The lifetime (T 95} ) when the current density was applied was measured, and the results are shown in Table 3 below. At this time, T ₉₅ represents the ratio of the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm ^{2 is 100% based on Comparative Example 8.}

entryentry	발광층light emitting layer		10mA/cm ² 10mA/cm ²		20mA/cm ² 20mA/cm ²
entryentry	호스트host	도펀트dopant	구동전압 (V)drive voltage (V)	환산효율 (cd/A/y)conversion efficiency (cd/A/y)	LT95 (ratio)LT95 (ratio)
실시예 8Example 8	BH-ABH-A	A-1A-1	3.87 3.87	44.7 44.7	1.201.20
실시예 9Example 9	BH-ABH-A	A-2A-2	3.86 3.86	45.4 45.4	1.521.52
실시예 10Example 10	BH-ABH-A	A-3A-3	3.88 3.88	45.3 45.3	1.501.50
실시예 11Example 11	BH-ABH-A	A-7A-7	3.89 3.89	45.9 45.9	1.451.45
실시예 12Example 12	BH-ABH-A	A-12A-12	3.90 3.90	46.7 46.7	1.531.53
실시예 13Example 13	BH-ABH-A	A-13A-13	3.85 3.85	46.1 46.1	1.451.45
실시예 14Example 14	BH-BBH-B	A-5A-5	3.85 3.85	46.0 46.0	1.301.30
실시예 15Example 15	BH-BBH-B	A-6A-6	3.90 3.90	45.1 45.1	1.251.25
실시예 16Example 16	BH-BBH-B	A-11A-11	3.89 3.89	46.4 46.4	1.421.42
실시예 17Example 17	BH-CBH-C	A-9A-9	3.89 3.89	45.5 45.5	1.331.33
실시예 18Example 18	BH-DBH-D	A-4A-4	3.79 3.79	45.9 45.9	1.55 1.55
실시예 19Example 19	BH-DBH-D	A-8A-8	3.78 3.78	45.1 45.1	1.30 1.30
실시예 20Example 20	BH-EBH-E	A-10A-10	3.83 3.83	45.0 45.0	1.28 1.28
실시예 21Example 21	BH-ABH-A	B-1B-1	3.86 3.86	45.1 45.1	1.38 1.38
실시예 22Example 22	BH-ABH-A	B-8B-8	3.87 3.87	45.6 45.6	1.35 1.35
실시예 23Example 23	BH-ABH-A	B-9B-9	3.77 3.77	45.8 45.8	1.36 1.36
실시예 24Example 24	BH-BBH-B	B-2B-2	3.89 3.89	45.2 45.2	1.27 1.27
실시예 25Example 25	BH-BBH-B	B-4B-4	3.85 3.85	45.4 45.4	1.34 1.34
실시예 26Example 26	BH-BBH-B	B-5B-5	3.85 3.85	45.5 45.5	1.32 1.32
실시예 27Example 27	BH-CBH-C	B-7B-7	3.82 3.82	45.1 45.1	1.33 1.33
실시예 28Example 28	BH-DBH-D	B-3B-3	3.77 3.77	44.5 44.5	1.11 1.11
실시예 29Example 29	BH-EBH-E	B-6B-6	3.73 3.73	45.6 45.6	1.30 1.30
실시예 30Example 30	BH-DBH-D	A-21A-21	3.783.78	45.845.8	1.161.16
실시예 31Example 31	BH-CBH-C	A-23A-23	3.81 3.81	44.9 44.9	1.271.27
실시예 32Example 32	BH-BBH-B	A-24A-24	3.86 3.86	45.2 45.2	1.181.18
비교예 8Comparative Example 8	BH-ABH-A	X-7X-7	3.99 3.99	43.2 43.2	1.00 1.00
비교예 9Comparative Example 9	BH-ABH-A	X-8X-8	3.97 3.97	41.0 41.0	1.15 1.15
비교예 10Comparative Example 10	BH-ABH-A	X-9X-9	4.00 4.00	44.1 44.1	0.75 0.75
비교예 11Comparative Example 11	BH-BBH-B	X-10X-10	3.97 3.97	42.3 42.3	1.03 1.03

Examples 33 to 40, Comparative Examples 12 and 13

Example 8 and Example 8 except that in Example 8, the compound shown in Table 4 was used instead of Compound A-1 as the dopant of the light emitting layer, and the compound shown in Table 4 was used instead of BH-A as the dopant material Using the same method, the organic light emitting devices of Examples 33 to 40 and Comparative Examples 12 and 13 were fabricated, respectively.

In Examples 30 to 36 and Comparative Examples 12 and 13, the weight ratio of the first host to the second host in the emission layer was 50:50.

Voltage, conversion efficiency (cd/A/y) and current density of ^{20 mA/cm 2} ^{when a current density of 10 mA/cm 2} is applied to the organic light emitting devices of Examples 33 to 40 and Comparative Examples 12 and 13 The lifetime (T ₉₅ ) when applying was measured, and the results are shown in Table 4 below. At this time, T ₉₅ represents the ratio of the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm ^{2 is 100% based on Comparative Example 8.}

entryentry	발광층light emitting layer			10mA/cm ² 10mA/cm ²		20mA/cm ² 20mA/cm ²
entryentry	제 1 호스트first host	제 2 호스트2nd host	도판트dopant	구동전압 (V)drive voltage (V)	환산효율 (cd/A/y)conversion efficiency (cd/A/y)	LT95 (ratio)LT95 (ratio)
실시예 33Example 33	BH-ABH-A	BH-DBH-D	A-2A-2	3.823.82	44.4944.49	1.371.37
실시예 34Example 34	BH-ABH-A	BH-EBH-E	A-4A-4	3.813.81	46.1346.13	1.511.51
실시예 35Example 35	BH-BBH-B	BH-DBH-D	A-8A-8	3.83.8	46.0046.00	1.301.30
실시예 36Example 36	BH-DBH-D	BH-EBH-E	A-11A-11	3.743.74	45.0145.01	1.241.24
실시예 37Example 37	BH-ABH-A	BH-EBH-E	B-5B-5	3.813.81	44.6444.64	1.251.25
실시예 38Example 38	BH-BBH-B	BH-DBH-D	B-6B-6	3.783.78	46.4946.49	1.351.35
실시예 39Example 39	BH-BBH-B	BH-EBH-E	B-9B-9	3.733.73	44.2044.20	1.201.20
실시예 40Example 40	BH-BBH-B	BH-DBH-D	A-22A-22	3.783.78	46.346.3	1.221.22
비교예 12Comparative Example 12	BH-ABH-A	BH-DBH-D	X-7X-7	3.943.94	41.9041.90	0.940.94
비교예 13Comparative Example 13	BH-BBH-B	BH-DBH-D	X-8X-8	3.913.91	40.1840.18	1.101.10

The conversion efficiency (cd/A/y) considers the current efficiency (cd/A) to the color purity (CIEy) of the material, and is an important reference value of efficiency in small and large organic light emitting devices aiming for high luminance and high color reproducibility. . As can be seen from the device results in Tables 3 and 4, the compounds including at least one condensed aliphatic hydrocarbon ring substituted with an alkyl group represented by Formula 1 according to an exemplary embodiment of the present specification have higher conversion efficiency and lifespan performance of the device than those that do not. All were excellent. In particular, when compared with compounds X-9 and X-10 containing an unsubstituted aliphatic hydrocarbon condensed ring, it was possible to confirm the excellent efficiency and lifespan performance of the dopant introducing the aliphatic hydrocarbon condensed ring substituted with an alkyl group. In addition, it was observed that the efficiency of the device improved as the number of aliphatic hydrocarbon condensed rings substituted with an alkyl group increased, which was consistent with the simulation test results of Experimental Example 1.

Examples 41 to 43, Comparative Examples 14 and 15

The same method as in Example 8 was used, except that in Example 8, the dopant compounds described in Table 5 were used instead of Compound A-1 as the dopant for the emission layer (parts by weight of the dopant relative to 100 parts by weight of the emission layer of the dopant) Thus, the organic light emitting devices of Examples 41 to 43 and Comparative Examples 14 and 15 were manufactured, respectively.

entryentry	도판트 (발광층)dopant (light emitting layer)	10mA/cm ² 10mA/cm ²				20mA/cm ² 20mA/cm ²
entryentry	도판트 (발광층)dopant (light emitting layer)	도핑 농도doping concentration	전류효율 (cd/A)current efficiency (cd/A)	환산효율 (cd/A/y)conversion efficiency (cd/A/y)	CIEyCIEy	LT95 (ratio)LT95 (ratio)
실시예 41Example 41	A-1A-1	0.5 중량부0.5 parts by weight	3.77 3.77	42.9 42.9	0.088 0.088	--
		2 중량부2 parts by weight	4.01 4.01	44.6 44.6	0.090 0.090	--
		4 중량부4 parts by weight	4.29 4.29	44.7 44.7	0.096 0.096	1.201.20
실시예 42Example 42	A-2A-2	0.5 중량부0.5 parts by weight	3.85 3.85	43.8 43.8	0.088 0.088	--
		2 중량부2 parts by weight	4.43 4.43	45.2 45.2	0.098 0.098	--
		4 중량부4 parts by weight	4.86 4.86	45.4 45.4	0.107 0.107	1.521.52
실시예 43Example 43	A-12A-12	0.5 중량부0.5 parts by weight	3.75 3.75	45.1 45.1	0.083 0.083	--
		2 중량부2 parts by weight	4.12 4.12	46.3 46.3	0.089 0.089	--
		4 중량부4 parts by weight	4.39 4.39	46.7 46.7	0.094 0.094	1.531.53
비교예 14Comparative Example 14	X-7X-7	0.5 중량부0.5 parts by weight	3.35 3.35	41.9 41.9	0.080 0.080	--
		2 중량부2 parts by weight	3.83 3.83	45.0 45.0	0.085 0.085	--
		4 중량부4 parts by weight	3.93 3.93	43.2 43.2	0.091 0.091	1.001.00
비교예 15Comparative Example 15	X-5X-5	0.5 중량부0.5 parts by weight	4.19 4.19	29.5 29.5	0.142 0.142	--
		2 중량부2 parts by weight	4.79 4.79	30.7 30.7	0.156 0.156	--
		4 중량부4 parts by weight	5.02 5.02	30.1 30.1	0.167 0.167	1.401.40

In Table 5, the compounds including at least one aliphatic hydrocarbon condensed ring substituted with an alkyl group of Formula 1 according to an exemplary embodiment of the present specification does not decrease efficiency even with high doping of the device, but rather increases the efficiency could confirm that In addition, when compared with the case of using the compound X-7 of Comparative Example 14 as a dopant of the light emitting layer of the organic light emitting device in the low doping concentration (0.5 parts by weight of dopant based on 100 parts by weight of the light emitting layer), the compound of Formula 1 of the present specification When A-1, A-2 and A-12 were used as a dopant in the emission layer of an organic light emitting device, higher efficiency performance was obtained. When Compound X-5 of Comparative Example 15 was used as a dopant in the emission layer of an organic light emitting device Although the current efficiency is very good, it can be seen that the conversion efficiency is low due to a decrease in color purity (CIEy) due to light emission in a long wavelength region.

Through the above various experiments, it was confirmed that the compound of Formula 1 according to an exemplary embodiment of the present specification has excellent performance of high efficiency and long life.

Examples 44 to 46, Comparative Examples 16 and 17

TGA (thermos gravimetric analyzer, thermogravimetric analyzer) is a device that measures the change in mass of a sample as a function of time or temperature by applying temperature to the sample. Mass loss of a material is caused by evaporation or chemical reactions that produce gaseous products. Using Q-500, 3 mg or more and less than 5 mg of the compound of Table 6, which had completed sublimation purification, was removed on a Pt pan and heated from room temperature to 700° C. at a rate of 10° C./min. At this time, the temperature at which the mass of the compound is reduced by 5% relative to the total weight (=Td-5% loss) and the amount (percent) of the residue remaining in the pan after heating to 700°C were measured. The TGA graph of Compound A-20 of Example 46 is shown in FIG. 13, and the TGA graph of Compounds X-5 and X-4 of Comparative Examples 16 and 17 are shown in FIGS. 14 and 15, respectively.

entryentry	비교예 16Comparative Example 16	비교예 17Comparative Example 17	실시예 44Example 44	실시예 45Example 45	실시예 46Example 46
화합물compound	X-5X-5	X-4X-4	A-2A-2	A-19A-19	A-20A-20
분자량Molecular Weight	770.95770.95	714.86714.86	845.05845.05	823.05823.05	1007.331007.33
Td-5% loss (℃)Td-5% loss (℃)	459459	386386	375375	390390	397397
잔류(%)Residual (%)	30.130.1	22.722.7	4.24.2	0.60.6	2.22.2

In Table 6 and FIGS. 13 to 15, as a result of thermogravimetric analysis of the symmetric compound X-5 of Comparative Example 16, the Td-5% loss value was measured to be very high at 459° C., and after analysis, 30% of the compound in the pan was remained. In addition, the Td-5% loss value of the asymmetric compound X-4 containing a heterocycle of Comparative Example 17 was slightly reduced, but the ratio of the compound remaining in Pan after analysis was measured to be about 23%. On the other hand, compounds A-2, A-19 and A-20, which are compounds including at least one condensed aliphatic hydrocarbon ring substituted with an alkyl group of Formula 1 according to the present specification of Examples 44 to 46, have a molecular weight greater than that of Compound X-4 , but with a lower or similar Td-5% loss.

Through this experiment, the compound of Formula 1 according to an exemplary embodiment of the present specification has a low Td% loss value compared to a similar molecular weight, so it can have a low sublimation temperature, so it is excellent in thermal stability and is an organic material suitable for a deposition device. Confirmed.

Claims

A compound represented by the following formula (1):

[Formula 1]

In Formula 1,

X1 is O or S;

A1 is a substituted or unsubstituted heterocyclic ring; a substituted or unsubstituted aromatic hydrocarbon ring; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

A2 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; Or a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group,

r1 is an integer from 1 to 3,

When r1 is 2 or more, the 2 or more R1 are the same as or different from each other,

Formula 1 includes at least one condensed aliphatic hydrocarbon ring substituted with a substituted or unsubstituted alkyl group.
The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 1-1 or 1-2:

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

The definitions of A1, A2, Ar1, Ar2, R1 and r1 are the same as those defined in Formula 1 above.
The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formulas 1-3 or 1-4:

[Formula 1-3]

[Formula 1-4]

In Formulas 1-3 and 1-4,

The definitions of X1, A2, Ar1, Ar2, R1 and r1 are the same as those defined in Formula 1 above,

A "1 is a substituted or unsubstituted aliphatic hydrocarbon ring,

R11 and R12 are the same as or different from each other, and each independently hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

r11 is an integer of 1 to 4, and when r11 is 2 or more, R11 of 2 or more are the same as or different from each other,

r12 is 1 or 2, and when r12 is 2, the two R12s are the same as or different from each other.
The compound according to claim 3, wherein Chemical Formula 1-4 is represented by the following Chemical Formula 1-4-1 or 1-4-2:

[Formula 1-4-1]

[Formula 1-4-2]

In Formulas 1-4-1 and 1-4-2,

The definitions of X1, A2, Ar1, Ar2, R1 and r1 are the same as those defined in Formula 1 above,

A "1 is a substituted or unsubstituted aliphatic hydrocarbon ring,

R12 is hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r12 is 1 or 2, and when r12 is 2, the two R12s are the same as or different from each other.
The method according to claim 1, wherein Chemical Formula 1 comprises at least one condensed monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 10 carbon atoms substituted with a linear or branched alkyl group having 1 to 30 carbon atoms that is unsubstituted or substituted with deuterium. compound.
The method according to claim 1, wherein A1 is a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms; a substituted or unsubstituted 6 to 30 monocyclic or polycyclic aromatic hydrocarbon ring; a substituted or unsubstituted 3 to 30 monocyclic or polycyclic aliphatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms,

A2 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or a condensed ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms,

wherein Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms; Or a condensed ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms,

wherein R1 is hydrogen; a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted amine group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or a compound that is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

In the compound, Ph represents a phenyl group, and D represents deuterium.
a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 7 light emitting element.
The organic light-emitting device of claim 8 , wherein the organic material layer includes an emission layer, and the emission layer includes the compound.
The organic light-emitting device of claim 8 , wherein the organic material layer includes an emission layer, the emission layer includes a dopant material, and the dopant material includes the compound.
The organic light-emitting device according to claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer further comprises a compound represented by the following Chemical Formula H:

[Formula H]

In the formula (H),

L20 and L21 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R20 and R21 are the same as or different from each other, and each independently represent hydrogen; heavy hydrogen; 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 heterocyclic group,

r21 is an integer of 1 to 7, and when r21 is 2 or more, 2 or more R21 are the same as or different from each other.
The organic light-emitting device of claim 11 , wherein Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.
The organic light emitting device of claim 8 , wherein the organic material layer includes a light emitting layer, the light emitting layer further comprises a host compound, and in the host compound, at least one hydrogen at a substitutable position is substituted with deuterium.
The organic light-emitting device of claim 8 , wherein the organic material layer includes an emission layer, and the emission layer includes one or more dopants and a host.
The organic light-emitting device of claim 8 , wherein the organic material layer includes an emission layer, and the emission layer includes two or more mixed dopants and a host.
The organic light-emitting device of claim 8 , wherein the organic material layer includes an emission layer, and the emission layer includes at least one host and a dopant.
The organic light emitting device of claim 8 , wherein the organic material layer includes an emission layer, and the emission layer includes two or more mixed hosts and a dopant.