CN117440960A

CN117440960A - Compounds and organic light-emitting devices containing the same

Info

Publication number: CN117440960A
Application number: CN202380012143.1A
Authority: CN
Inventors: 李多精; 金明坤; 金京嬉; 李禹哲; 黄晟现
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2022-03-11
Filing date: 2023-03-10
Publication date: 2024-01-23
Also published as: WO2023172110A1; KR20230133804A; KR102855164B1

Abstract

The present specification provides a compound of formula 1 and an organic light emitting device including the same.

Description

Compound and organic light emitting device comprising the same

Technical Field

The present application claims priority from korean patent application No. 10-2022-0030805, filed to the korean patent office on 3-11 of 2022, the entire contents of which are incorporated herein.

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

Background

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

There is a continuing need to develop new materials for use in organic light emitting devices as described above. Among them, in the case of blue organic light emitting devices, high color purity and long life characteristics are necessary, but a technique for simultaneously realizing them is lacking because of instability caused by high energy of blue substances. In recent years, a thermally activated delayed fluorescent substance having a core structure containing boron has been newly developed and attracting attention with high efficiency and color purity, but has disadvantages of high triplet energy, slow rate of intersystem crossing in reverse direction, and short lifetime. Accordingly, development of a blue organic light-emitting body that achieves both high color purity and long lifetime characteristics is demanded.

Disclosure of Invention

Technical problem

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

Solution to the problem

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

[ chemical formula 1]

In the above-mentioned chemical formula 1,

a1 is a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring,

a2 is a substituted or unsubstituted hydrocarbon ring,

the above A1 and A2 are bonded to each other to form a substituted or unsubstituted ring, or to form no ring,

r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G1) (G2), substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or any one or more pairs of adjacent ones of the above R1 and R2 are bonded to each other to form a substituted or unsubstituted ring,

Z1 is deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G3) (G4), substituted or unsubstituted aryl, a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or Z2 is combined with each other to form a substituted or unsubstituted hydrocarbon ring,

when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G3) (G4), substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group,

g1 to G4 are the same or different from each other and each independently is 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 of 1 to 5, and when R1 is 2 or more, the 2 or more R1 s are the same or different from each other,

r2 is an integer of 1 to 4, and when R2 is 2 or more, the 2 or more R2 are the same or different from each other.

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

Effects of the invention

The compound according to an embodiment of the present specification can be used as a material of an organic layer of an organic light emitting device, and by using the compound, improvement of high color purity, high efficiency, and/or lifetime characteristics can be achieved in the organic light emitting device.

Drawings

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

[ description of the symbols ]

1: substrate board

2: first electrode

3: light-emitting layer

4: second electrode

5: first hole injection layer

6: a second hole injection layer

7: hole transport layer

8: electron blocking layer

9: a first electron transport layer

10: a second electron transport layer

11: electron injection layer

Detailed Description

The present specification will be described in more detail below.

An embodiment of the present specification relates to a compound of formula 1 above.

The organic light-emitting device to which the conventional boron compound is applied has a disadvantage of a short lifetime, although the organic light-emitting device to which the pyrene compound is applied has a higher efficiency than the organic light-emitting device to which the conventional boron compound is applied. However, the compound of formula 1 has a narrow half width, and the organic light emitting device including the same has advantages of increased efficiency and lifetime. The six-membered ring of boron and amine maintains a narrow half width and fills insufficient electrons of boron by direct bonding of the opposite side boron and amine, thereby increasing stability of the nucleus in an unstable state such as a polaron state to increase lifetime, and the polaron smoothly migrates to an exciton state, thereby exhibiting a pattern of increased efficiency of an organic light emitting device including the same.

Throughout the specification of the present application, the term "a combination of these" included in the markush-type expression means that one or more components selected from the group consisting of the components described in the markush-type expression are mixed or combined, and that one or more components selected from the group consisting of the components are included.

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

In the present description of the invention,indicating the location of the connection.

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

In the present specification, the term "substituted or unsubstituted" means substituted or unsubstituted by a group selected from deuterium, halogen group, cyano, alkyl, cycloalkyl, alkoxy, aryloxy, alkylthioArylthio->Alkenyl, haloalkyl, haloalkoxy, arylalkyl, silyl, boron, amino, aryl, fused ring groups of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and 1 or more substituents in a heterocyclic group, or substituents formed by connecting 2 or more substituents among the above-exemplified substituents, or no substituent.

In the present specification, the connection of 2 or more substituents means that hydrogen of any substituent is connected to other substituents. For example, 2 substituents may be linked by phenyl to naphthylSuch substituents. Further, 3 substituent linkages include not only (substituent 1) - (substituent 2) - (substituent 3) linked continuously, but also (substituent 2) and (substituent 3) linked to (substituent 1). For example, phenyl, naphthyl and isopropyl groups can be attached as +.>Such substituents. The same definition as above applies to the connection of more than 4 substituents.

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

In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof 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-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, cycloalkyl is not particularly limited, but cycloalkyl having 3 to 30 carbon atoms is preferable, 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, bicyclo [2.2.1] heptyl, bicyclo [2.2.1] octyl, norbornyl, and the like are included, but not limited thereto.

In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.

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

In the present specification, the haloalkoxy group refers to hydrogen substituted with at least one halogen group instead of an alkoxy group in the definition of the alkoxy group.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be a single ring or a multiple ring.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, or 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, but is preferably 10 to 30. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, phenalenyl, perylenyl,A group, a fluorenyl group, etc., but is not limited thereto.

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

As examples of the above fluorenyl group, there are And the like, but is not limited thereto.

In this specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted by the substituent. For example, 2 substituents substituted in the benzene ring at the ortho (ortho) position and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, arylalkyl means that the alkyl group is substituted with an aryl group, and examples of the aryl group and the alkyl group of the arylalkyl group are applicable.

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

In the present specification, the alkyl group of the alkylthio group is the same as exemplified for the alkyl group described above. Specifically, the alkylthio group includes, but is not limited to, a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and the like.

In the present specification, the aryl group in the arylthio group is the same as exemplified for the aryl group described above. Specifically, the arylthio group includes, but is not limited to, phenylthio group, 2-methylphenylthio group, 4-tert-butylphenylthio group and the like.

In the present specification, a heterocyclic group contains 1 or more heteroatoms which are non-carbon atoms, specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se, S and the like, and the heterocyclic group contains 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 is preferably 2 to 30, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl Indolyl, carbazolyl, benzo +.>Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthridinyl (phenanthrinyl), phenanthroline (phenanthrinyl), iso->Azolyl, thiadiazolyl, dibenzofuranyl, dibenzosilol and pheno +.>Thioyl (phenoxathiine), pheno +.>Oxazinyl (phenoxazine), phenothiazinyl (phenothiazine), decahydrobenzocarbazolyl, hexahydrocarbazolyl, dihydrobenzosilacyclohexane, indanocarbazolyl, spirofluorenxanthenyl, spirofluorenothioyl, tetrahydronaphthothienyl, tetrahydronaphthofuranyl, tetrahydrobenzothienyl, tetrahydrobenzofuranyl, and the like, but are not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, arylsilyl group, alkylarylsilyl group, heteroarylsilyl group or the like. The alkyl group in the alkylsilyl group may be exemplified by the alkyl group, the aryl group in the arylsilyl group may be exemplified by the aryl group, the alkyl group and the aryl group in the alkylarylsilyl group may be exemplified by the alkyl group and the aryl group, and the heteroaryl group in the heteroarylsilyl group may be exemplified by the heterocyclic group.

In the present specification, the boron group may be-BR ₁₀₀ R ₁₀₁ R is as described above ₁₀₀ And R is ₁₀₁ The same or different, each independently may be selected from hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted monocyclic or polycyclic cycloalkyl of 3 to 30 carbon atoms, substituted or unsubstituted straight or branched alkyl of 1 to 30 carbon atoms, substituted or unsubstitutedA monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.

In the present specification, the amine group may be selected from the group consisting of-NH ₂ The alkyl amine group, the N-alkylaryl amine group, the aryl amine group, the N-arylheteroaryl amine group, the N-alkylheteroaryl amine group and the heteroaryl amine group are not particularly limited, but are preferably 1 to 30 in carbon number. Specific examples of the amine group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamine group, a naphthylamino group, a biphenylamino group, an anthracenylamino group, a 9-methyl-anthracenylamino group, a diphenylamino group, a xylylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrenylamino group, an N-phenylfluorenylamino group, an N-biphenylfluorenylamino group, and the like, but are not limited thereto.

In the present specification, the N-alkylaryl amine group means an amine group in which an alkyl group and an aryl group are substituted on N of the amine group. The alkyl group and the aryl group in the above-mentioned N-alkylaryl amine group are the same as exemplified for the alkyl group and the aryl group described above.

In the present specification, an N-arylheteroarylamino group means an amino group substituted with an aryl group and a heteroaryl group on N of the amino group. The aryl and heteroaryl groups in the above-mentioned N-arylheteroarylamino groups are the same as those exemplified for the aryl and heterocyclic groups described above.

In the present specification, an N-alkylheteroarylamino group means an amino group in which an alkyl group and a heteroaryl group are substituted on N of the amino group. The alkyl group and heteroaryl group in the above-mentioned N-alkylheteroaryl amine group are the same as exemplified for the alkyl group and heterocyclic group described above.

In the present specification, as examples of the alkylamino group, there are a substituted or unsubstituted monoalkylamino group, or a substituted or unsubstituted dialkylamino group. The alkyl group in the above-mentioned alkylamino group may be a linear or branched alkyl group. The alkylamino group containing 2 or more of the above-mentioned alkyl groups may contain a linear alkyl group, a branched alkyl group, or may contain both a linear alkyl group and a branched alkyl group. For example, the alkyl group in the above-mentioned alkylamino group may be selected from the examples of the alkyl group described above.

In the present specification, as examples of the heteroarylamino group, there is a substituted or unsubstituted mono-heteroarylamino group or a substituted or unsubstituted di-heteroarylamino group. The heteroarylamine group containing 2 or more of the above heteroaryl groups may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or may contain both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the above heteroaryl amine 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 exemplified by the cycloalkyl group, the aryl group, and combinations thereof, and the hydrocarbon ring group is exemplified by phenyl group, cyclohexyl group, adamantyl group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.1] octyl group, tetrahydronaphthyl group, tetrahydroanthryl group, 1,2,3, 4-tetrahydro-1, 4-methylenenaphthyl group, 1,2,3, 4-tetrahydro-1, 4-ethylenenaphthyl group, and the like, but is not limited thereto.

In this specification, "adjacent" means the same as the above definition in "forming a ring with adjacent groups being bonded to each other," the above "ring" means a substituted or unsubstituted hydrocarbon ring, or 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, and may be selected from the cycloalkyl group, the aryl group, and combinations thereof, other than the above 1-valent hydrocarbon ring, and the hydrocarbon ring is exemplified by benzene, cyclohexane, adamantane, bicyclo [2.2.1] heptane, bicyclo [2.2.1] octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2,3, 4-tetrahydro-1, 4-methylenenaphthalene, 1,2,3, 4-tetrahydro-1, 4-ethylenenaphthalene, and the like, but is not limited thereto.

The aliphatic hydrocarbon ring includes all of a single-bond hydrocarbon ring, a hydrocarbon ring containing multiple bonds, which is not aromatic, and a ring in which a single bond and multiple bonds are condensed. Therefore, the ring composed of a single bond in the aliphatic hydrocarbon ring is not a 1-valent group, and may be selected from the above examples of cycloalkyl groups, and hydrocarbon rings containing a single bond and a double bond but not an aromatic ring, such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclononene, cyclodecene, and cyclonorbornene, belong to the aliphatic hydrocarbon ring.

In this specification, a heterocyclic ring contains 1 or more heteroatoms which are non-carbon atoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se, S and the like. The heterocyclic ring may be a single ring or multiple rings, and may be an aromatic heterocyclic ring; aliphatic heterocycles; condensed rings of an aromatic heterocycle and an aliphatic heterocycle; condensed rings of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and an aromatic heterocyclic ring; or a condensed ring of an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring and an aliphatic heterocyclic ring, and the aromatic heterocyclic ring may be exemplified by heteroaryl groups selected from the heterocyclic groups except for 1-valent aromatic heterocyclic rings.

In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more hetero atoms. Aliphatic heterocycles include all of single-bond aliphatic rings, multi-bond aliphatic rings, or single-bond and multi-bond ring-fused forms of aliphatic rings. Examples of aliphatic heterocycles include ethylene oxide (oxalane), tetrahydrofuran, and 1, 4-di-Alkyl (1, 4-dioxane), pyrrolidine, piperidine, morpholine (morpholine), oxetane, azacyclooctane, thietane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, tetrahydrobenzofuran, and the like, but are not limited thereto.

In one embodiment of the present specification, the moiety in which a substituent is not indicated in the above chemical formula 1 may represent a substitution with hydrogen.

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

According to an embodiment of the present specification, the above chemical formula 1 is any one of the following chemical formulas 2 to 6.

[ chemical formula 2]

[ chemical formula 3]

[ chemical formula 4]

[ chemical formula 5]

[ chemical formula 6]

In the above-mentioned chemical formulas 2 to 6,

a1, R1, R2, R1, R2, Z1 and Z2 are as defined in the above chemical formula 1,

r3 to R6 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G5) (G6), substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or any one or more of the above R3 to R6 and the above A1 are combined with each other to form a substituted or unsubstituted ring,

g5 and G6 are the same or different from each other and each independently is a substituted or unsubstituted aryl group, a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group,

r3 is an integer of 1 to 4, and when R3 is 2 or more, the 2 or more R3 are the same or different from each other,

r4 is an integer of 1 to 6, and when R4 is 2 or more, the 2 or more R4 are the same or different from each other,

R5 is an integer of 1 to 4, and when R5 is 2 or more, the 2 or more R5 are the same or different from each other,

r6 is an integer of 1 to 4, and when R6 is 2 or more, the 2 or more R6 are the same or different from each other.

According to an embodiment of the present specification, the above chemical formula 1 is any one of the following chemical formulas 7 to 9.

[ chemical formula 7]

[ chemical formula 8]

[ chemical formula 9]

In the above-mentioned chemical formulas 7 to 9,

a1, R1, R2, R1, R2, Z1 and Z2 are as defined in the above chemical formula 1,

r7 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G5) (G6), substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or is combined with the above A1 to form a substituted or unsubstituted ring,

g5 and G6 are the same or different from each other and each independently is 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,

r7 is an integer of 1 to 10, and when R7 is 2 or more, the 2 or more R7 are the same or different from each other.

According to one embodiment of the present specification, A1 is a substituted or unsubstituted aromatic hydrocarbon ring; condensed rings of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring containing 1 or more of O, N, S and Si.

According to an embodiment of the present specification, the above chemical formula 1 is the following chemical formula 10 or 11.

[ chemical formula 10]

[ chemical formula 11]

In the above-mentioned chemical formulas 10 and 11,

a2, R1, R2, R1, R2, Z1 and Z2 are as defined in the above chemical formula 1,

x1 is-C (R13) (R14) -, -Si (R15) (R16) -, -O-, or-S-,

r11 to R16 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G7) (G8), substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or any one or more pairs of adjacent ones of the above R11 to R16 are bonded to each other to form a substituted or unsubstituted ring,

r11 and A2 are bonded to each other to form a substituted or unsubstituted ring or not,

R12 and A2 are bonded to each other to form a substituted or unsubstituted ring or not,

g7 and G8 are the same or different from each other and each independently is 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,

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

r12 is an integer of 1 to 4, and when R12 is 2 or more, the 2 or more R12 are the same or different from each other.

According to an embodiment of the present specification, chemical formula 1 above is any one of the following chemical formulas 12 to 23.

[ chemical formula 12]

[ chemical formula 13]

[ chemical formula 14]

[ chemical formula 15]

[ chemical formula 16]

[ chemical formula 17]

[ chemical formula 18]

[ chemical formula 19]

[ chemical formula 20]

[ chemical formula 21]

[ chemical formula 22]

[ chemical formula 23]

In the above-mentioned chemical formulas 12 to 23,

a2, R1, R2, R1, R2, Z1 and Z2 are as defined in the above chemical formula 1,

x1 is-C (R13) (R14) -, -Si (R15) (R16) -, -O-, or-S-,

x2 and X3 are the same or different from each other, each independently is-C (R19) (R20) -, -Si (R21) (R22) -, -O-, or-S-,

x4 and X5 are the same or different from each other, each independently is-C (R23) (R24) -, -Si (R25) (R26) -, -N (R27), -O-, or-S-,

Y1 to Y4 are identical to or different from one another and are each independently-C (R28) -or N,

r '2, R'2, R '11, R'11 and R12 to R28 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G9) (G10), substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or any one or more adjacent pairs of the above-mentioned R '2, R'2, R '11, R'11 and R12 to R28 are bonded to each other to form a substituted or unsubstituted ring,

g9 and G10 are the same or different from each other and each independently is 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,

r '11 is an integer of 1 to 4, and when R '11 is 2 or more, R '11 of 2 or more are the same or different from each other,

r '11 is an integer of 1 to 3, and when R '11 is 2 or more, R '11 of 2 or more are the same or different from each other,

r ' "11 is 1 or 2, and when R '" 11 is 2, the 2R ' "11 are the same or different from each other,

R '2 is an integer of 1 to 4, and when R '2 is 2 or more, the 2 or more R '2 s are the same or different from each other,

r "2 is 1 or 2, and when R"2 is 2, the 2R "2 are the same or different from each other,

r12 is an integer of 1 to 4, and when R12 is 2 or more, the 2 or more R12 are the same or different from each other,

r17 is an integer of 1 to 4, and when R17 is 2 or more, the 2 or more R17 are the same or different from each other,

r18 is an integer of 1 to 4, and when R18 is 2 or more, the 2 or more R18 are the same or different from each other.

According to an embodiment of the present specification, the above chemical formula 1 is the following chemical formula 24 or 25.

[ chemical formula 24]

[ chemical formula 25]

In the above-mentioned chemical formulas 24 and 25,

a1, A2, R1, R1, R2, R2 and Z1 are as defined in the above chemical formula 1,

r101 is hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G11) (G12), substituted or unsubstituted aryl, condensed ring group of substituted or unsubstituted aromatic hydrocarbon ring and aliphatic hydrocarbon ring, or substituted or unsubstituted heterocyclic group,

g11 and G12 are the same or different from each other and each independently is 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,

R101 is an integer of 1 to 4, and when R101 is 2 or more, the 2 or more R101 are the same or different from each other.

According to an embodiment of the present specification, A1 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 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, -N (G7) (G8), a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and a combination thereof; condensed rings 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring containing 2 to 30 carbon atoms of 1 or more of O, N and S, which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group of 1 to 30 carbon atoms, -N (G7) (G8), a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms, and combinations thereof,

the A2 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, -N (G5) (G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a condensed ring 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, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms,

The above A1 and A2 are combined with each other to form a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is substituted or unsubstituted by 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof; or the formation of a loop may not be performed,

each of the above R1 and R2 is the same or different from each other and is independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, -N (G1) (G2), a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of the above R1 and R2 are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; condensed rings 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl having 6 to 30 carbon atoms, and a combination thereof,

The above-mentioned Z1 is a straight-chain or branched alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; -N (G3) (G4); substituted or unsubstituted monocyclic or polycyclic aryl group of 6 to 30 carbon atoms with deuterium, linear or branched alkyl group of 1 to 30 carbon atoms, or monocyclic or polycyclic aryl group of 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is bonded to Z2,

when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen,

the above-mentioned G1 to G8 are the same or different from each other and each independently is a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the present specification, A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; condensed rings 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 substituted or unsubstituted heterocyclic ring containing 1 or more of O, N and S and having 2 to 30 carbon atoms, which is a single ring or a plurality of rings.

According to one embodiment of the present specification, A1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; condensed rings 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 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 6 to 20 carbon atoms containing 1 or more of O, N and S.

According to an embodiment of the present specification, A1 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 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, -N (G7) (G8), a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and a combination thereof; condensed rings 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring containing 2 to 30 carbon atoms of 1 or more of O, N and S, which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group of 1 to 30 carbon atoms, -N (G7) (G8), a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, A1 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 6 to 20 carbon atoms, a linear or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G7) (G8), a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a monocyclic or polycyclic heterocyclic group having 6 to 20 carbon atoms, and a combination thereof; condensed rings of a monocyclic or polycyclic aromatic hydrocarbon ring of 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring of 6 to 20 carbon atoms, which are substituted or unsubstituted with a linear or branched alkyl group of 1 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic ring containing 1 or more of O, N and S and having 6 to 20 carbon atoms, which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms, -N (G7) (G8), a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, A1 is benzene substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 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, -N (G7) (G8), a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, and a combination thereof; naphthalene; fluorene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthalene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran; dibenzothiophenes; tetrahydronaphthofuran substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydronaphthothiophene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; benzo substituted or unsubstituted by monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms An azole; benzothiazole substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; benzimidazole substituted or unsubstituted with 1 or more groups selected from the group consisting of straight or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; a benzofuran substituted or unsubstituted with 1 or more substituents selected from the group consisting of linear or branched alkyl groups having 1 to 30 carbon atoms, -N (G7) (G8), monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; or a benzothiophene substituted or unsubstituted with 1 or more groups selected from the group consisting of straight or branched alkyl groups having 1 to 30 carbon atoms, -N (G7) (G8), monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof.

According to one embodiment of the present specification, A1 is selected from the group consisting of carbon atoms1 to 20, a cyclic or polycyclic cycloalkyl group having 6 to 20 carbon atoms, a linear or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G7) (G8), a cyclic or polycyclic aryl group having 6 to 20 carbon atoms, a cyclic or polycyclic heterocyclic group having 6 to 20 carbon atoms, and a combination thereof; naphthalene; fluorene substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; tetrahydronaphthalene substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; dibenzofuran; dibenzothiophenes; tetrahydronaphthofuran substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; tetrahydronaphthothiophene substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; benzo substituted or unsubstituted by monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms An azole; benzothiazole substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; benzimidazole substituted or unsubstituted with 1 or more groups selected from the group consisting of straight or branched alkyl groups having 1 to 20 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, and combinations thereof; a benzofuran substituted or unsubstituted with 1 or more substituents selected from the group consisting of linear or branched alkyl groups of 1 to 20 carbon atoms, -N (G7) (G8), monocyclic or polycyclic aryl groups of 6 to 20 carbon atoms, and combinations thereof; or a benzothiophene substituted or unsubstituted with 1 or more groups selected from the group consisting of linear or branched alkyl groups having 1 to 20 carbon atoms, -N (G7) (G8), monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, and combinations thereof.

According to an embodiment of the present specification, A1 is benzene substituted or unsubstituted with 1 or more groups selected from the group consisting of methyl, t-butyl, cyclohexyl, trimethylsilyl, phenyl, biphenyl, hexahydrocarbazolyl, -N (G7) (G8), and combinations thereof; naphthalene; fluorene substituted or unsubstituted with methyl; tetrahydronaphthalene substituted or unsubstituted with methyl; dibenzofuran; dibenzothiophenes; tetrahydronaphthofuran substituted or unsubstituted with methyl; tetrahydronaphthothiophenes substituted or unsubstituted with methyl groups The method comprises the steps of carrying out a first treatment on the surface of the Benzo substituted or unsubstituted by phenylAn azole; benzothiazole substituted or unsubstituted with phenyl; benzimidazole substituted or unsubstituted with 1 or more selected from the group consisting of methyl, phenyl, and combinations thereof; benzofuran substituted or unsubstituted with 1 or more members selected from the group consisting of methyl, t-butyl, -N (G7) (G8), phenyl, and combinations thereof; or a benzothiophene substituted or unsubstituted with 1 or more groups selected from methyl, t-butyl, -N (G7) (G8), phenyl, and combinations thereof.

According to one embodiment of the present specification, A2 is a substituted or unsubstituted aromatic 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.

According to an embodiment of the present specification, A2 is a substituted or unsubstituted aromatic 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 6 to 20 carbon atoms.

According to an embodiment of the present specification, A2 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, -N (G5) (G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a condensed ring 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, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, A2 is a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, -N (G5) (G6), or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present specification, A2 is benzene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, -N (G5) (G6), or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; naphthalene; or tetrahydronaphthalene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, A2 is benzene substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, -N (G5) (G6), or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthalene; or straight or branched alkyl substituted or unsubstituted tetrahydronaphthalene having 1 to 20 carbon atoms.

According to an embodiment of the present specification, the above A2 is benzene substituted or unsubstituted with methyl, tert-butyl, -N (G5) (G6), or phenyl; naphthalene; or tetrahydronaphthalene substituted or unsubstituted with methyl.

According to an embodiment of the present specification, A1 and A2 described above are combined with each other to form or not form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, A1 and A2 described above are bonded to each other to form or not form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 6 to 20 carbon atoms.

According to an embodiment of the present specification, A1 and A2 described above are bonded to each other to form or not to form a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, which is substituted or unsubstituted by 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, A1 and A2 described above are bonded to each other to form or not to form a monocyclic or polycyclic heterocyclic ring having 6 to 20 carbon atoms which is substituted or unsubstituted by 1 or more selected from a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, the above A1 and A2 are combined with each other to form or not to form a substituted or unsubstituted dihydroacridine with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof; spiroacridine fluorene; or a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, the above A1 and A2 are combined with each other to form or not to form a substituted or unsubstituted dihydroacridine with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof; spiroacridine fluorene; or a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present specification, the above A1 and A2 are combined with each other to form or not to form a dihydroacridine substituted or unsubstituted with 1 or more selected from t-butyl, phenyl, naphthyl, and combinations thereof; spiroacridine fluorene; or a methyl-substituted or unsubstituted indano acridine.

According to an embodiment of the present specification, each of the above R1 and R2 is the same or different from each other, and is independently hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, N (G1) (G2), 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, or any one or more adjacent pairs of the above R1 and R2 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, 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, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, each of the above R1 and R2 is the same or different from each other, and is independently hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G1) (G2), 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, or any one or more adjacent pairs of the above R1 and R2 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, 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 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms.

According to an embodiment of the present specification, the above R1 and R2 are the same or different from each other, and each is independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, -N (G1) (G2), a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of the above R1 and R2 are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; condensed rings 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, the above R1 and R2 are the same or different from each other, and each is independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G1) (G2), a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or any one or more adjacent pairs of the above R1 and R2 are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; condensed rings of a monocyclic or polycyclic aromatic hydrocarbon ring of 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring of 6 to 20 carbon atoms, which are substituted or unsubstituted with a linear or branched alkyl group of 1 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, the above-mentioned R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, methyl, isopropyl, tert-butyl, trimethylsilyl, -N (G1) (G2), phenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, biphenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, naphthyl, fluorenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or hexahydrocarbazolyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of the above-mentioned R1 and R2 are bonded to each other to form cyclohexene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; benzene; indene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; substituted by straight-chain or branched alkyl radicals having 1 to 30 carbon atomsUnsubstituted tetrahydronaphthofurans; tetrahydronaphthothiophene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; naphthofuran; naphthothiophene; cyclopentene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; tetrahydrocyclopentanaphthalene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuran; dibenzothiophenes; fluorene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a dihydropyridine substituted or unsubstituted with 1 or more groups selected from the group consisting of linear or branched alkyl groups having 1 to 30 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and combinations thereof; spirofluorene pyridine; pyrrole; An oxazine; or dihydropyrazinoindoles.

According to an embodiment of the present specification, the above-mentioned R1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, methyl, isopropyl, tert-butyl, trimethylsilyl, -N (G1) (G2), phenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, biphenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, naphthyl, fluorenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, or hexahydrocarbazolyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, or any one or more adjacent pairs of the above-mentioned R1 and R2 are bonded to each other to form cyclohexene substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; benzene; indene substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; tetrahydronaphthofuran substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; tetrahydronaphthothiophene substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; naphthofuran; naphthothiophene; cyclopentene substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; tetrahydrocyclopentanaphthalene substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; dibenzofuran; dibenzothiophenes; straight-chain or branched alkyl groups having 1 to 20 carbon atoms Substituted or unsubstituted fluorene; a dihydropyridine substituted or unsubstituted with 1 or more groups selected from the group consisting of linear or branched alkyl groups having 1 to 20 carbon atoms, monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, and combinations thereof; spirofluorene pyridine; pyrrole;an oxazine; or dihydropyrazinoindoles.

According to an embodiment of the present specification, R1 and R2 are the same or different from each other, and each is independently hydrogen; deuterium; a methyl group; an isopropyl group; a tertiary butyl group; trimethylsilyl; -N (G1) (G2); phenyl substituted or unsubstituted with tert-butyl; biphenyl substituted or unsubstituted with tert-butyl; a naphthyl group; fluorenyl substituted or unsubstituted with methyl; or a hexahydrocarbazolyl group substituted or unsubstituted with a methyl group, or any one or more adjacent pairs of the above R1 and R2 are bonded to each other to form a cyclohexene substituted or unsubstituted with a methyl group; benzene; indene substituted or unsubstituted with methyl; tetrahydronaphthofuran substituted or unsubstituted with methyl; tetrahydronaphthothiophene substituted or unsubstituted with methyl; naphthofuran; naphthothiophene; cyclopentene substituted or unsubstituted with methyl; tetrahydrocyclopentanaphthalene substituted or unsubstituted with methyl; dibenzofuran; dibenzothiophenes; fluorene substituted or unsubstituted with methyl; dihydropyridines substituted or unsubstituted with 1 or more groups selected from methyl, phenyl, and combinations thereof; spirofluorene pyridine; pyrrole; An oxazine; or dihydropyrazinoindoles.

According to an embodiment of the present specification, R1 is hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N (G1) (G2), 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, or any one or more adjacent pairs of R1 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to an embodiment of the present specification, R1 is hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G1) (G2), 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, or any one or more adjacent pairs of R1 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an embodiment of the present specification, R1 is hydrogen, deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, -N (G1) (G2), a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of the above R1 are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, R1 is hydrogen, deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G1) (G2), a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or any one or more adjacent pairs of the above R1 are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present specification, the above-mentioned R1 is hydrogen, deuterium, methyl, isopropyl, tert-butyl, trimethylsilyl, -N (G1) (G2), phenyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, biphenyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, naphthyl, fluorenyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or hexahydrocarbazolyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of the above-mentioned R1 are bonded to each other to form cyclohexene substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, benzene, or indene substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, the above-mentioned R1 is hydrogen, deuterium, methyl, isopropyl, tert-butyl, trimethylsilyl, -N (G1) (G2), phenyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, biphenyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, naphthyl, fluorenyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or hexahydrocarbazolyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or any one or more adjacent pairs of the above-mentioned R1 are bonded to each other to form cyclohexene substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, benzene, or indene substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present specification, the above R1 is hydrogen, deuterium, methyl, isopropyl, tert-butyl, trimethylsilyl, -N (G1) (G2), phenyl substituted or unsubstituted by tert-butyl, biphenyl substituted or unsubstituted by tert-butyl, naphthyl, fluorenyl substituted or unsubstituted by methyl, or hexahydrocarbazolyl substituted or unsubstituted by methyl, or any one or more adjacent pairs of the above R1 are combined with each other to form cyclohexene substituted or unsubstituted by methyl, benzene, or indene substituted or unsubstituted by methyl.

According to an embodiment of the present specification, R2 is hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N (G1) (G2), 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, or any one or more adjacent pairs of R2 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, 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, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, R2 is hydrogen, deuterium, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G1) (G2), 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, or any one or more adjacent pairs of R2 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, a fused 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 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms.

According to an embodiment of the present specification, the above R2 is hydrogen, deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, -N (G1) (G2), a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of the above R2 are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; condensed rings 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, the above R2 is hydrogen, deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, a linear or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G1) (G2), a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or any one or more adjacent pairs of the above R2 are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; condensed rings of a monocyclic or polycyclic aromatic hydrocarbon ring of 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring of 6 to 20 carbon atoms, which are substituted or unsubstituted with a linear or branched alkyl group of 1 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, the above-mentioned R2 is hydrogen, deuterium, methyl, isopropyl, tert-butyl, trimethylsilyl, -N (G1) (G2), phenyl substituted or unsubstituted by straight-chain or branched alkyl having 1 to 30 carbon atoms, biphenyl substituted or unsubstituted by straight-chain or branched alkyl having 1 to 30 carbon atoms, naphthyl, fluorenyl substituted or unsubstituted by straight-chain or branched alkyl having 1 to 30 carbon atoms, hexahydrocarbazolyl substituted or unsubstituted by straight-chain or branched alkyl having 1 to 30 carbon atoms, or any one or more pairs of adjacent ones of the above-mentioned R2 combine with each other to form cyclohexene substituted or unsubstituted by straight-chain or branched alkyl having 1 to 30 carbon atoms, benzene, indene substituted or unsubstituted by straight-chain or branched alkyl having 1 to 30 carbon atoms, tetrahydronaphthofuran substituted or unsubstituted by straight-chain or branched alkyl having 1 to 30 carbon atoms, naphthothiophene substituted or unsubstituted by straight-chain or branched naphthofuran having 1 to 30 carbon atoms; tetrahydrocyclopentanaphthalene, dibenzofuran, dibenzothiophene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or fluorene substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, the above-mentioned R2 hydrogen, deuterium, methyl, isopropyl, tert-butyl, trimethylsilyl, -N (G1) (G2), phenyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, biphenyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, naphthyl, fluorenyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or hexahydrocarbazolyl substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, or any one or more pairs of adjacent R2 groups combine with each other to form cyclohexene substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, benzene, tetrahydronaphthofuran substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, tetrahydronaphthothiophene substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, tetrahydrothiophene substituted or unsubstituted by a linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted naphthalene having 1 to 20 carbon atoms.

According to an embodiment of the present specification, the above R2 is hydrogen, deuterium, methyl, isopropyl, tert-butyl, trimethylsilyl, -N (G1) (G2), phenyl substituted or unsubstituted by tert-butyl, biphenyl substituted or unsubstituted by tert-butyl, naphthyl, fluorenyl substituted or unsubstituted by methyl, or hexahydrocarbazolyl substituted or unsubstituted by methyl, or any one or more pairs adjacent to the above R2 are combined with each other to form cyclohexene substituted or unsubstituted by methyl, benzene, indene substituted or unsubstituted by methyl, tetrahydronaphthofuran substituted or unsubstituted by methyl, tetrahydronaphthothiophene substituted or unsubstituted by methyl, naphthofuran, cyclopentanaphthalene substituted or unsubstituted by methyl, tetrahydrocyclopentanaphthalene substituted or unsubstituted by methyl, dibenzofuran, dibenzothiophene, or fluorene substituted or unsubstituted by methyl.

According to an embodiment of the present specification, the above R1 and R2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, the above R1 and R2 are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms.

According to an embodiment of the present specification, the above R1 and R2 are bonded to each other to form a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, which is substituted or unsubstituted by 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, the above R1 and R2 are combined with each other to form a monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms, which is substituted or unsubstituted by 1 or more selected from the group consisting of a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof.

According to an embodiment of the present specification, the above R1 and R2 are combined with each other to form a dihydropyridine substituted or unsubstituted with 1 or more groups selected from a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a combination thereof; spirofluorene pyridine; pyrrole;an oxazine; or dihydropyrazinoindoles.

According to an embodiment of the present specification, the above R1 and R2 are combined with each other to form a dihydropyridine substituted or unsubstituted with 1 or more groups selected from a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a combination thereof; spirofluorene pyridine; pyrrole; An oxazine; or dihydropyrazinoindoles.

According to an embodiment of the present specification, R1 and R2 are bonded to each other to form a dihydropyridine substituted or unsubstituted with one or more groups selected from the group consisting of methyl, phenyl, and combinations thereof; spirofluorene pyridine; pyrrole;an oxazine; or dihydropyrazinoindoles.

According to an embodiment of the present specification, Z1 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 30 carbon atoms, -N (G3) (G4), 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 substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is bonded to Z2.

According to an embodiment of the present specification, Z1 is a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted straight-chain or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G3) (G4), 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 6 to 20 carbon atoms, or is combined with Z2 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an embodiment of the present specification, Z1 is a linear or branched alkyl group having 1 to 30 carbon atoms, which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; -N (G3) (G4); substituted or unsubstituted monocyclic or polycyclic aryl group of 6 to 30 carbon atoms with deuterium, linear or branched alkyl group of 1 to 30 carbon atoms, or monocyclic or polycyclic aryl group of 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is bonded to each other with Z2.

According to an embodiment of the present specification, Z1 is a linear or branched alkyl group having 1 to 20 carbon atoms, which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a linear or branched alkylsilyl group having 1 to 20 carbon atoms; -N (G3) (G4); substituted or unsubstituted monocyclic or polycyclic aryl group of 6 to 20 carbon atoms with deuterium, linear or branched alkyl group of 1 to 20 carbon atoms, or monocyclic or polycyclic aryl group of 6 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 6 to 20 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms which is formed by bonding Z2 to each other.

According to an embodiment of the present specification, Z1 is a methyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; an isopropyl group; a tertiary butyl group; trimethylsilyl; -N (G3) (G4); phenyl substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; biphenyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a terphenyl group; a fluorenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuranyl; dibenzothienyl; carbazolyl; phenonesAn oxazinyl group; a hexahydrocarbazolyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a dihydroacridinyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or Z2 is bonded to each other to form a benzene ring.

According to an embodiment of the present specification, Z1 is a methyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; an isopropyl group; a tertiary butyl group; trimethylsilyl; -N (G3) (G4); phenyl substituted or unsubstituted with deuterium, a linear or branched alkyl group of 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group of 6 to 20 carbon atoms; biphenyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a terphenyl group; a fluorenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; dibenzofuranyl; dibenzothienyl; carbazolyl; phenones An oxazinyl group; a hexahydrocarbazolyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; or a dihydroacridinyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, or Z2 is bonded to each other to form a benzene ring.

According to an embodiment of the present specification, Z1 is methyl substituted or unsubstituted with phenyl; an isopropyl group; tert-butyl groupThe method comprises the steps of carrying out a first treatment on the surface of the Trimethylsilyl; -N (G3) (G4); phenyl substituted or unsubstituted with deuterium, methyl, tert-butyl, phenyl or biphenyl; biphenyl substituted or unsubstituted with phenyl; a terphenyl group; fluorenyl substituted or unsubstituted with methyl; dibenzofuranyl; dibenzothienyl; carbazolyl; phenonesAn oxazinyl group; a hexahydrocarbazolyl group substituted or unsubstituted with methyl; or a dihydroacridinyl group substituted or unsubstituted with a methyl group, or Z2 and Z are combined with each other to form a benzene ring.

According to an embodiment of the present specification, when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 1 to 30 carbon atoms, -N (G3) (G4), 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.

According to an embodiment of the present specification, when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkylsilyl group having 1 to 20 carbon atoms, -N (G3) (G4), 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 6 to 20 carbon atoms.

According to an embodiment of the present specification, when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; -N (G3) (G4); substituted or unsubstituted monocyclic or polycyclic aryl group of 6 to 30 carbon atoms with deuterium, linear or branched alkyl group of 1 to 30 carbon atoms, or monocyclic or polycyclic aryl group of 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a linear or branched alkylsilyl group having 1 to 20 carbon atoms; -N (G3) (G4); substituted or unsubstituted monocyclic or polycyclic aryl group of 6 to 20 carbon atoms with deuterium, linear or branched alkyl group of 1 to 20 carbon atoms, or monocyclic or polycyclic aryl group of 6 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 6 to 20 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present specification, when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen; methyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; an isopropyl group; a tertiary butyl group; trimethylsilyl; -N (G3) (G4); phenyl substituted or unsubstituted with deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; biphenyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a terphenyl group; a fluorenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuranyl; dibenzothienyl; carbazolyl; phenonesAn oxazinyl group; a hexahydrocarbazolyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a dihydroacridinyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen; methyl substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; an isopropyl group; a tertiary butyl group; trimethylsilyl; -N (G3) (G4); phenyl substituted or unsubstituted with deuterium, a linear or branched alkyl group of 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group of 6 to 20 carbon atoms; by a single ring of 6 to 20 carbon atoms Polycyclic aryl substituted or unsubstituted biphenyl; a terphenyl group; a fluorenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; dibenzofuranyl; dibenzothienyl; carbazolyl; phenonesAn oxazinyl group; a hexahydrocarbazolyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; or a dihydroacridinyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an embodiment of the present specification, when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen; methyl substituted or unsubstituted with phenyl; an isopropyl group; a tertiary butyl group; trimethylsilyl; -N (G3) (G4); phenyl substituted or unsubstituted with deuterium, methyl, tert-butyl, phenyl or biphenyl; biphenyl substituted or unsubstituted with phenyl; a terphenyl group; fluorenyl substituted or unsubstituted with methyl; dibenzofuranyl; dibenzothienyl; carbazolyl; phenonesAn oxazinyl group; a hexahydrocarbazolyl group substituted or unsubstituted with methyl; or a dihydroacridinyl group substituted or unsubstituted with a methyl group.

According to an embodiment of the present specification, when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen.

According to an embodiment of the present specification, the above-mentioned G1 to G8 are the same or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 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.

According to an embodiment of the present specification, the above-mentioned G1 to G8 are the same or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, 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.

According to an embodiment of the present specification, the above-mentioned G1 to G8 are the same or different from each other, and each is independently a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

According to an embodiment of the present specification, the above-mentioned G1 to G8 are the same or different from each other, and each is independently a linear or branched alkyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

According to an embodiment of the present specification, the above-mentioned G1 to G8 are the same or different from each other, each independently being a methyl group; a tertiary butyl group; phenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; biphenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; a naphthyl group; a fluorenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; dibenzofuranyl; or benzothienyl.

According to an embodiment of the present specification, the above-mentioned G1 to G8 are the same or different from each other, each independently being a methyl group; a tertiary butyl group; phenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; biphenyl substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; a naphthyl group; a fluorenyl group substituted or unsubstituted with a linear or branched alkyl group having 1 to 20 carbon atoms; dibenzofuranyl; or dibenzothienyl.

According to an embodiment of the present specification, the above-mentioned G1 to G8 are the same or different from each other, each independently being a methyl group; a tertiary butyl group; phenyl substituted or unsubstituted with methyl, tert-butyl or phenyl; biphenyl substituted or unsubstituted with methyl; a naphthyl group; fluorenyl substituted or unsubstituted with methyl; dibenzofuranyl; or dibenzothienyl.

According to an embodiment of the present specification, the above chemical formula 1 is any one of the following compounds.

In the above compounds, t-Bu means tert-butyl.

The present specification provides an organic light emitting device comprising the above-mentioned compound.

In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.

In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.

In the present specification, the term "layer" is used interchangeably with "film" mainly used in the art, and means a coating layer covering a target region. The size of the "layers" is not limited, and the respective "layers" may be the same or different in size. According to an embodiment, the size of the "layer" may be equal to the size of the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel (sub-pixel).

In the present specification, the meaning that a specific a substance is contained in a B layer includes all of i) a case where 1 or more a substances are contained in a B layer of one layer, and ii) a case where a B layer is composed of 1 or more layers and a substance is contained in 1 or more layers of a multi-layer B layer.

In the present specification, the inclusion of a specific substance a in the C layer or the D layer means that all cases where i) is included in 1 layer or more of the C layers of 1 layer or more, or ii) is included in 1 layer or more of the D layers of 1 layer or more, or iii) is included in the C layers of 1 layer or more and the D layers of 1 layer or more, respectively, are included.

In the present specification, "deuterated", "deuterium-substituted" or "deuterated" means that hydrogen at a position of a compound that can be substituted is substituted with deuterium.

In the present specification, "X%" substituted with deuterium, "X% deuterated," "deuterated degree X%", or "deuterium substitution rate X%" means that X% of hydrogen at a position where substitution is possible in the structure is substituted with deuterium. For example, when the structure is a dibenzofuran, the "25% substitution with deuterium" of the dibenzofuran, "25% deuterated" of the dibenzofuran, the "25% deuteration degree" of the dibenzofuran, or the "25% substitution rate of deuterium" of the dibenzofuran means that 2 of 8 hydrogens of the position where the dibenzofuran can be substituted are substituted with deuterium.

In the present specification, the degree of deuteration may be determined by nuclear magnetic resonance spectroscopy ¹ H NMR), TLC/MS (Thin layer chromatography/mass spectrometry, thin-Layer Chromatography/Mass Spectrometry), or MALDI-TOF MS (matrix assisted laser Desorption/ionization Time of flight mass spectrometry, matrix assisted laser desorption/ionization Time-of-Flight Mass Spectrometry).

The present specification provides an organic light emitting device, including: a first electrode, a second electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound of the chemical formula 1.

The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, 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 may be provided. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound of formula 1.

In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound of formula 1 as a dopant of the light emitting layer.

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

In an embodiment of the present specification, the organic light emitting device further includes 1 layer or 2 layers or more selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

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

In one embodiment of the present disclosure, the light-emitting layer further includes a host compound, and at least one hydrogen at a position where the host compound can be substituted is substituted with deuterium.

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

In an embodiment of the present disclosure, the light emitting layer further includes a compound of the following chemical formula H.

[ chemical formula H ]

In the above-mentioned chemical formula H,

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

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

r200 and R201 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r201 is an integer of 1 to 7, and when R201 is 2 or more, 2 or more R201 are the same or different from each other.

In one embodiment of the present specification, L20 and L21 are the same or different from each other, and each is 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 one embodiment of the present specification, L20 and L21 are the same or different from each other, and each is 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 embodiment of the present specification, the above L20 and L21 are the same or different from each other, and each is independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, a deuterium-substituted or unsubstituted naphthylene group, a 2-valent dibenzofuranyl group, or a 2-valent dibenzothienyl group.

In one embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is 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 one embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is 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 one embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

In an embodiment of the present specification, ar20 and Ar21 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenacyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted naphthobenzothienyl group.

In an embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a dibenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a dibenzobenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a benzodibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In an embodiment of the present specification, ar20 and Ar21 are the same or different from each other, and each is independently a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a terphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a phenanthryl group, a phenyl-substituted or unsubstituted dibenzofuranyl group, a naphthobenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, or a benzodibenzofuranyl group.

In one embodiment of the present specification, ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R200 is hydrogen, deuterium, a halogen group, 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 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 one embodiment of the present specification, R200 is hydrogen, deuterium, fluorine, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R200 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 one embodiment of the present specification, R200 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 one embodiment of the present specification, R200 is hydrogen, a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R200 is hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted phenacyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted naphthobenzothienyl.

In one embodiment of the present specification, R200 is hydrogen, deuterium, a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a naphthyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, a dibenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a naphthobenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R200 is hydrogen; deuterium; phenyl substituted or unsubstituted with deuterium, phenyl or naphthyl; a biphenyl group; naphthyl substituted or unsubstituted with deuterium, phenyl or naphthyl; dibenzofuranyl; naphthobenzofuranyl; dibenzothienyl; or a naphtobenzothienyl group.

According to an embodiment of the present disclosure, R201 is hydrogen.

According to an embodiment of the present disclosure, R201 is deuterium.

In one embodiment of the present specification, when the compound of formula H is substituted with deuterium, hydrogen at a position that can be substituted is substituted with deuterium by 30% or more. In another embodiment, the hydrogen at the position where it can be substituted of the structure of formula H above is substituted by deuterium by 40% or more. In another embodiment, the hydrogen at the position where it can be substituted of the structure of formula H above is substituted by deuterium by 60% or more.

In another embodiment, the hydrogen at the position where it can be substituted in the structure of formula H above is substituted by deuterium by 80% or more. In another embodiment, the hydrogen at the position where the structure of formula H above can be substituted is 100% substituted with deuterium.

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

According to an embodiment of the present specification, the compound represented by the above chemical formula H may be manufactured by the following general formula 1, but is not limited thereto.

[ general formula 1]

In the above-mentioned general formula 1,

Ar ₁ the definition of-L20-Ar 20 is the same as that of the above chemical formula H,

Ar ₂ r200 and R201 may be further substituted in the anthracene nucleus of the above general formula 1 as defined for-L21-Ar 21 of the above chemical formula H.

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

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

The light-emitting layer may further include a host material, and the host may include an aromatic condensed ring derivative, a heterocyclic compound, or the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds The pyrimidine derivative, the triazine derivative, or the like may be a mixture of 2 or more of them, but is not limited thereto.

According to an embodiment of the present disclosure, the organic layer includes a light emitting layer, and the light emitting layer further includes 1 or more dopants and a host.

According to an embodiment of the present disclosure, the organic layer includes a light emitting layer including 2 or more mixed dopants and a host.

According to an embodiment of the present specification, 1 or more of the 2 or more mixed dopants include the compound of formula 1, and the host includes the compound of formula H. The chemical formula 1 is contained in 1 or more of the 2 or more mixed dopants, and the remaining dopant substances known in the past can be used, but are not limited thereto.

According to an embodiment of the present specification, 1 or more of the 2 or more mixed dopants include the chemical formula 1, and 1 or more of a boron compound, a pyrene compound, and a delayed fluorescence compound different from the chemical formula 1 may be used in the rest, but is not limited thereto.

According to an embodiment of the present disclosure, the organic layer includes a light-emitting layer, and the light-emitting layer further includes 1 or more hosts.

According to an embodiment of the present disclosure, the organic layer includes a light-emitting layer including 2 or more kinds of mixed hosts.

According to an embodiment of the present specification, 1 or more of the 2 or more kinds of mixed bodies are the compounds of the chemical formula H.

According to an embodiment of the present specification, the above 2 or more kinds of mixed bodies are different from each other, and each is independently a compound of the above formula H.

According to an embodiment of the present specification, the organic layer includes a light emitting layer including 2 kinds of mixed hosts.

According to an embodiment of the present disclosure, the organic layer includes a light emitting layer including 2 kinds of mixed hosts, the 2 kinds of mixed hosts being different from each other, and the 2 kinds of hosts being compounds of the chemical formula H.

According to an embodiment of the present specification, the organic layer includes a light emitting layer including a first body of the chemical formula H and a second body of the chemical formula H, and the first body and the second body are different from each other.

According to an embodiment of the present disclosure, the first body and the second body are contained in a weight ratio of 95:5 to 5:95, preferably in a weight ratio of 70:30 to 30:70.

According to an embodiment of the present specification, the organic layer includes a light emitting layer including 1 or more host and dopant.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer including 1 or more kinds of host including the compound of formula H and a dopant including the compound of formula 1.

According to an embodiment of the present disclosure, the organic layer includes a light emitting layer including 2 or more mixed hosts and dopants.

According to an embodiment of the present specification, 1 or more of the 2 or more mixed hosts include the compound of formula H, and the dopant includes the compound of formula 1.

In the present specification, the above 2 or more kinds of mixing bodies are different from each other.

According to an embodiment of the present specification, the organic layer includes a light emitting layer including 2 kinds of mixed hosts and dopants.

According to an embodiment of the present specification, the 2 kinds of mixed hosts are different from each other, each independently including the compound of formula H, and the dopant includes the compound of formula 1.

According to an embodiment of the present specification, the dopant includes a first host of the chemical formula H, a second host of the chemical formula H, and a dopant of the chemical formula 1, and the first host and the second host are different from each other.

According to one embodiment of the present specification, the organic layer uses 1 or more hosts and 1 or more dopants, the 1 or more hosts include the compound of formula H, and the 1 or more dopants include the compound of formula 1.

According to an embodiment of the present disclosure, the organic layer may use 2 or more kinds of mixed hosts and 2 or more kinds of mixed dopants, the 2 or more kinds of mixed hosts may use the same material as the above, and the 2 or more kinds of mixed dopants may use the same material as the above.

According to one embodiment of the present disclosure, the organic layer includes a light emitting layer including a dopant substance including the compound of formula 1.

According to an embodiment of the present disclosure, the light emitting layer further includes 1 or more dopants and a host. The above 1 or more dopants may be conventionally known dopant substances, but are not limited thereto.

According to an embodiment of the present disclosure, the light emitting layer further includes 1 or more kinds of host. The above 1 or more main bodies contain a compound of the above formula H.

According to an embodiment of the present disclosure, the light emitting layer further includes 2 or more kinds of mixed hosts. More than 1 of the 2 or more mixed bodies contains the compound of the chemical formula H.

According to an embodiment of the present disclosure, the light emitting layer further includes 2 or more kinds of mixed hosts. The 2 kinds of mixed bodies are different from each other and each independently include the compound of the formula H.

In an 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 at least 2 organic 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 at least 2 organic layers contains the compound of formula 1.

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

In an embodiment of the present specification, the organic light emitting device may include 2 or more electron transport layers, but is not limited thereto.

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

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

In an embodiment of the present invention, the materials of the layers of the electron transport layer of 2 or more layers may be the same or different from each other.

In an embodiment of the present specification, the organic light emitting device may include 2 or more hole injection layers, but is not limited thereto.

In an embodiment of the present invention, the materials of the layers of the hole injection layer of 2 or more layers may be the same or different from each other.

When the organic layer including the compound of chemical formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. The n-type dopant may use materials known in the art, for example, a metal or a metal complex may be used. For example, the electron transport layer including the compound of the above chemical formula 1 may further include LiQ (Lithium Quinolate, lithium quinolinolate).

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

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

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

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

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

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

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

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

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

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

In addition to the above-described compound, that is, the compound of chemical formula 1, 1 or more of the organic layers of the organic light-emitting device of the present specification may be manufactured using materials and methods known in the art.

When the organic light emitting device includes a plurality of organic layers, the organic 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 layer, and a second electrode on a substrate. This can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

In addition, the compound of chemical formula 1 may be used not only in the vacuum deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, 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 a cathode material, an organic layer, and an anode material on a substrate (international patent application publication No. 2003/012890). However, the manufacturing method is not limited thereto.

As the first electrode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. For example, there are metals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO ₂ A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.

As the second electrode material, a material having a small work function is generally preferable in order to facilitate injection of electrons into the organic layer. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; liF/Al or LiO ₂ And/or Al, but is not limited thereto.

In the present specification, the compound of the above chemical formula 1 is contained except forWhen an organic layer other than the light-emitting layer or a separate light-emitting layer is provided, the light-emitting substance of the light-emitting layer is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. For example, there are 8-hydroxyquinoline aluminum complex (Alq ₃ ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The light emitting layer may include a host material and a dopant material. Examples of the host material include aromatic condensed ring derivatives and heterocyclic compounds. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include dibenzofuran derivatives and ladder-type furan compounds Pyrimidine derivatives, etc., but are not limited thereto.

When the dopant material contains a compound other than the compound of chemical formula 1, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene having an arylamine group,Bisindenopyrene, and the like. In addition, styreneThe arylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.

The hole injection layer is a layer that injects holes from the electrode. The hole injection substance is preferably the following: a substance having a hole transporting ability, an effect of injecting holes from the first electrode, and an excellent hole injecting effect to the light emitting layer or the light emitting material. Further, a substance which can prevent migration of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material is preferable. Further, a substance having excellent film forming ability is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injecting substance is interposed between the work function of the first electrode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include metalloporphyrin (porphyrin); an oligothiophene; an arylamine-based organic substance; carbazole-based organic material; nitrile organic matter; hexanitrile hexaazatriphenylene organic compounds; quinacridone (quinacridone) is an organic substance; perylene (perylene) based organic compounds; anthraquinone, polyaniline, polythiophene-based conductive polymers, and the like; or a mixture of 2 or more of the above examples, but is not limited thereto.

According to an embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.

[ chemical formula HI-1]

In the above-mentioned chemical formula HI-1,

r301 to R306 are the same as or different from each other and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,

l301 and L302 are the same 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 having a valence of 2.

According to an embodiment of the present specification, R301 and R302 are the same as or different from each other, and each is independently a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present disclosure, R301 and R302 are methyl groups.

According to an embodiment of the present specification, R301 and R302 are combined with each other to form a substituted or unsubstituted heterocycle.

According to one embodiment of the present disclosure, R301 and R302 are combined with each other to form a substituted or unsubstituted dihydroacridine ring or a substituted or unsubstituted indoloacridine ring.

According to an embodiment of the present specification, R301 and R302 are combined with each other to form a dihydroacridine ring substituted or unsubstituted with a phenyl group, or an indoloacridine ring.

According to an embodiment of the present disclosure, the L301 and L302 are directly bonded.

According to an embodiment of the present specification, the above-mentioned R303 to R306 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present specification, R303 to R306 are the same or different from each other, and each is independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, R303 to R306 are the same or different from each other, and each is independently a phenyl group or a carbazolyl group substituted or unsubstituted with a phenyl group.

According to an embodiment of the present specification, the above formula HI-1 is represented by the following compound, but is not limited thereto.

According to an embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-2.

[ chemical formula HI-2]

In the above-mentioned chemical formula HI-2,

at least one of X '1 to X'6 is N, the remainder are CH,

r309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with each other with an adjacent group to form a substituted or unsubstituted ring.

According to an embodiment of the present specification, X '1 to X'6 are N.

According to an embodiment of the present disclosure, R309 to R314 are cyano groups.

According to one embodiment of the present specification, the above formula HI-2 is represented by the following compounds.

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

According to an embodiment of the present specification, the hole transport layer includes a compound represented by the following chemical formula HT-1, but is not limited thereto.

[ chemical formula HT-1]

In the above-mentioned chemical formula HT-1,

r'314, R315 and R316 are the same or different from each other and are each independently any one selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with each other with adjacent groups to form a substituted or unsubstituted ring,

r315 is an integer of 1 to 5, and when R315 is 2 or more, 2 or more of R315 are the same or different from each other,

r316 is an integer of 1 to 5, and when R316 is 2 or more, 2 or more R316 are the same or different from each other.

According to an embodiment of the present disclosure, the R'314 is any one selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof.

According to an embodiment of the present disclosure, R'314 is any one selected from the group consisting of carbazolyl, phenyl, biphenyl, naphthyl, and combinations thereof.

According to an embodiment of the present specification, R315 and R316 are the same or different from each other, and each is independently a substituted or unsubstituted aryl group, or are combined with each other to form an alkyl or aryl substituted or unsubstituted aromatic hydrocarbon ring.

According to an embodiment of the present specification, R315 and R316 are the same or different from each other, and are each independently phenyl, or are combined with each other with adjacent groups to form benzene, or are substituted or unsubstituted indene with phenyl or methyl.

According to one embodiment of the present specification, the above formula HT-1 is represented by the following compounds.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transporting layer material is a material that can satisfactorily receive electrons from the second electrode and transfer the electrons to the light emitting layer, and preferably has a high mobility to electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq ₃ But not limited to, complexes of (a) and (b), organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, liQ, and the like. The electron transport layer may be used with any desired first electrode material as used in the art. In particular, a suitable first electrode material has a low work function and is accompanied by a usual material of an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium are present, in each case accompanied by an aluminum layer or a silver layer.

According to an embodiment of the present specification, the electron transport layer includes a compound represented by the following chemical formula ET-1.

[ chemical formula ET-1]

In the above-mentioned chemical formula ET-1,

at least one of X '7 to X'8 is N, the remainder are CH,

r317 to R322 are identical to or different from each other and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with each other with the adjacent groups to form a substituted or unsubstituted ring,

l'1 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

r322 is an integer of 1 to 7, and when R322 is 2 or more, R322 is the same or different from each other,

l '1 is an integer of 1 to 5, and when L '1 is 2 or more, L '1 is the same as or different from each other.

According to an embodiment of the present specification, R317 to R322 are the same as or different from each other, and each is independently hydrogen, or a substituted or unsubstituted aryl group, or adjacent groups are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an embodiment of the present specification, the above-mentioned R317 to R322 are the same or different from each other, each independently is hydrogen, phenyl or naphthyl, or adjacent groups are bonded to each other to form benzene.

According to one embodiment of the present specification, the L'1 is a substituted or unsubstituted arylene group.

According to one embodiment of the present specification, the L'1 is phenylene.

According to an embodiment of the present specification, the above ET-1 is selected from the following compounds.

According to an embodiment of the present specification, the electron transport layer includes a compound represented by the following chemical formula ET-2.

[ chemical formula ET-2]

In the above-mentioned chemical formula ET-2,

t1 to T3 are the same or different from each other and are each independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with each other with adjacent groups to form a substituted or unsubstituted ring,

t1 is an integer of 1 to 4, and when T1 is 2 or more, 2 or more of T1 s are the same or different from each other,

t2 is an integer of 1 to 4, and when T2 is 2 or more, 2 or more of T2 are the same or different from each other,

t3 is an integer of 1 to 10, and when T3 is 2 or more, 2 or more T3 s are the same or different from each other.

According to an embodiment of the present specification, the above-mentioned T1 to T3 are the same or different from each other, each independently is any one selected from the group consisting of hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and combinations thereof.

According to an embodiment of the present specification, T1 to T3 are the same or different from each other, and each is independently any one selected from the group consisting of hydrogen, carbazolyl, phenyl, biphenyl, triazinyl, and combinations thereof.

According to an embodiment of the present specification, the above ET-2 is selected from the following compounds.

The electron transport layer may further comprise a metal complex. The above metal may be a metal used in the art.

The electron injection layer is a layer that injects electrons from the electrode. The electron injection material is preferably the following: a substance having an excellent electron-transporting ability, an excellent electron-injecting effect into the second electrode, and an excellent electron-injecting effect into the light-emitting layer or the light-emitting material. Further, it is preferable that excitons generated in the light-emitting layer are prevented from migrating to the hole injection layer, and that the thin film forming ability is excellent. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the nitrogen-containing compound include, but are not limited to, diazoles, triazoles, triazines, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and mixtures of 2 or more of the foregoing examples.

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

The electron blocking layer is a layer that can prevent electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer, thereby improving the lifetime and efficiency of the device. The 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 a layer that performs hole injection and hole transport at the same time.

According to an embodiment of the present disclosure, the electron blocking layer is represented by the chemical formula HT-1.

The hole blocking layer is a layer that prevents holes from passing through the light emitting layer to the cathode, and can be formed generally under the same conditions as those of the electron injection layer. Specifically, there are The diazole derivative or triazole derivative, phenanthroline derivative, aluminum complex (aluminum complex), pyridine, pyrimidine, triazine derivative, or the like, but is not limited thereto.

The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.

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

The compounds according to the present specification can also function in organic light-emitting devices typified by organic phosphorescent devices, organic solar cells, organic photoreceptors, organic transistors, and the like, on principles similar to those applicable to organic light-emitting devices. For example, the organic solar energy may have a structure including a cathode, an anode, and a photoactive layer disposed between the cathode and the anode, and the photoactive layer may include the compound.

The organic light emitting device according to the present specification may be included in various electronic apparatuses to be used. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, or the like, but is not limited thereto.

The organic light-emitting device of the present specification can be manufactured by a general method and material for manufacturing an organic light-emitting device, in addition to forming one or more organic layers using the above-described compound.

Modes for carrying out the invention

In the following, examples, comparative examples, and the like will be described in detail for the purpose of specifically describing the present specification. However, the examples and comparative examples according to the present specification may be modified into various forms, and the scope of the present specification is not to be construed as being limited to the examples and comparative examples described in detail below. Examples and comparative examples of the present description are provided to more fully illustrate the present description to those skilled in the art.

Synthesis example 1

1) Production of Compound a-1

2-chloro-4-methyl-9H-carbazole (2-chloro-4-methyl-9H-carbazole) (100 g,463.6 mmol) and 1- (tert-butyl) -4-iodobenzene (1- (tert-butyl) -4-iodobenzene) (120.6 g,463.6 mmol), sodium tert-butoxide (89.1 g,927.3 mmol) were added to 2000ml toluene (tolene) under nitrogen atmosphere, stirred and returnedAnd (3) flow. Then, bis (tri-tert-butylphosphine) palladium (0) (bis (tris-tert-butylphosphine) palladium (0)) (2.4 g,4.6 mmol) was charged. After 3 hours, at the end of the reaction, the mixture was cooled to room temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, after washing with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the slurry filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 120.7g of compound a-1 was obtained. (yield 75%, MS: [ M+H) ] ⁺ ＝348)

2) Production of Compound a

The compounds a-1 (120.7 g,346.9 mmol) and 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline (4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxab-an-2-yl) aniline) (155.5 g,381.6 mmol) were added to 2414ml of 1, 4-bis (1, 4-dioxido)The mixture was stirred and refluxed in alkane (1, 4-dioxane). Then, potassium phosphate (potassim phosphate) (220.9 g,1040.8 mmol) was dissolved in 663ml of water and then poured, and after stirring thoroughly, bis (tri-t-butylphosphine) palladium (0) (1.8 g,3.5 mmol) was poured. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 100.8g of compound a was produced. (yield 49%, MS: [ M+H)] ⁺ ＝593)

3) Production of Compound 1

Compound a (20 g,33.7 mmol) and boron triiodide (19.8 g,50.6 mmol) were added to 200ml of 1,2-dichlorobenzene (1, 2-dichloro-benzene) under nitrogen atmosphere and stirred at 160 ℃. After 5 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 8.1g of Compound 1. (yield 40%, MS: [ M+H) ] ⁺ ＝601)

Synthesis example 2

1) Production of Compound b-2

Compound b-2 was synthesized by the same method as the production method of compound a, using 7-bromo-9-chloro-11H-benzo [ a ] carbazole (7-bromoo-9-chloroo-11H-benzocarbazole) instead of compound a-1, and using phenylboronic acid (phenylboronic acid) instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline.

2) Production of Compound b-1

Compound b-1 was synthesized by the same method as the production method of compound a-1, using compound b-2 instead of 2-chloro-4-methyl-9H-carbazole and 6-iodo-1, 4-tetramethyl-1,2,3,4-tetrahydronaphthalene (6-iodo-1, 4-tetrahyd-roaphthane) instead of 1- (tert-butyl) -4-iodobenzene.

3) Production of Compound b

Compound b-1 was used instead of compound a-1, using 5- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline (5- (tert-butyl) -N- (4- (t-butyl) phenyl) -2-; 4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound b was synthesized by the same method as the production method of compound a.

4) Production of Compound 2

Compound b (20 g,26.3 mmol) and boron triiodide (15.5 g,39.5 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 4 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 9.3g of Compound 2. (yield 46%, MS: [ M+H)] ⁺ ＝767)

Synthesis example 3

1) Production of Compound c-2

Compound c-2 was synthesized by the same method as the production method of compound a, using 1-bromo-3-chloro-5H-benzo [ b ] carbazole (1-bromoo-3-chloro-5H-carbaz ole) instead of compound a-1, using (4- (tert-butyl) phenyl) boronic acid instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline.

2) Production of Compound c-1

Compound c-1 was synthesized by the same method as the production method of compound a-1, using compound c-2 instead of 2-chloro-4-methyl-9H-carbazole and 6-iodo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene instead of 1- (tert-butyl) -4-iodobenzene.

3) Production of Compound c

Compound c-1 was used instead of compound a-1, using 5, 8-tetramethyl-3- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) -N- (5, 8-tetramethyl-5,6,7, 8-tetrahydronaphthalen-2-yl) -5,6,7, 8-tetrahydronaphthalen-2-amine (5, 8-tetramethy-3- (4, 5-tetramethy-1, 3, 2-dioxab-rate) olan-2-yl) -N- (5, 8-tetramethy l-5,6,7, 8-tetrahydrononaphthlen-2-yl) -5,6,7,8-te trahydronaphthalen-2-amine) replaces 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound c was synthesized by the same method as the production method of compound a.

4) Production of Compound 3

Compound c (20 g,21.7 mmol) and boron triiodide (12.7 g,32.5 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction for 2 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 6.9g of Compound 3. (yield 34%, MS: [ M+H)] ⁺ ＝932)

Synthesis example 4

1) Production of Compound d-2

Compound d-2 was synthesized by the same method as the production method of compound a-1, using 7-bromo-9-chloro-11H-benzo [ a ] carbazole instead of 2-chloro-4-methyl-9H-carbazole and 1- (tert-butyl) -3-iodobenzene (1- (tert-butyl) -3-iodobenzene) instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound d-1

Compound d-1 was synthesized by the same method as the production method of compound a-1 using bis (4- (tert-butyl) phenyl) amine instead of 2-chloro-4-methyl-9H-carbazole and compound d-2 instead of 1- (tert-butyl) -4-iodobenzene.

3) Production of Compound d

Compound d was synthesized by the same method as the production method of compound a, using compound d-1 instead of compound a-1 and N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline.

4) Production of Compound 4

Compound d (20 g,23.5 mmol) and boron triiodide (13.8 g,35.2 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 3 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 8.7g of Compound 4. (yield 43%, MS: [ M+H)] ⁺ ＝861)

Synthesis example 5

1) Production of Compound e-2

Compound e-2 was synthesized by the same method as the production method of compound a-1, using 4-bromo-2-chloro-9H-carbazole (4-bromoo-2-chloroo-9H-carbazole) instead of 2-chloro-4-methyl-9H-carbazole, and using 6-iodo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound e-1

Compound e-1 was synthesized by the same method as the production method of compound a-1 using diphenylamine (diphenylamine) instead of 2-chloro-4-methyl-9H-carbazole and compound e-2 instead of 1- (tert-butyl) -4-iodobenzene.

3) Production of Compound e

Compound e-1 was used instead of compound a-1, use of 5, 8-tetramethyl-3- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -N- (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalen-2-yl) -5,6,7,8 tetrahydronaphthalen-2-amine in place of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline, compound e was synthesized by the same method as the production method of compound a.

4) Production of Compound 5

Compound e (20 g,22 mmol) and boron triiodide (12.9 g,33 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 2 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 9.5g of Compound 5. (yield 47%, MS: [ M+H)] ⁺ ＝917)

Synthesis example 6

1) Production of Compound f-1

Compound f-1 was synthesized by the same method as the production method of compound a-1 using 5-chloro-7H-dibenzo [ c, g ] carbazole (5-chloro-7H-dibenzo [ c, g ] carbazole) instead of 2-chloro-4-methyl-9H-carbazole and 1- (tert-butyl) -3-iodobenzene instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound f

Compound f-1 was used instead of compound a-1, using N- (5- (tert-butyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) phenyl) -5, 8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (N- (5- (tert-butyl) -2- (4, 5-tetramethy-l-1, 3,2- -Dioxaborolan-2-yl) phenyl) -5, 8-tetramethy-5, 6,7, 8-tetrahydroaphthalen-2-amine in place of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound f was synthesized by the same method as the production method of compound a.

3) Production of Compound 6

Compound f (20 g,27.3 mmol) and boron triiodide (16 g,40.9 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction for 1 hour, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 6.1g of Compound 6. (yield 30%, MS: [ M+H)] ⁺ ＝741)

Synthesis example 7

1) Production of Compound g-1

Compound g-1 was synthesized by the same method as the production method of compound a-1 using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and 11-bromo-13-chloro-5, 5-dimethyl-5H-benzo [ a ] indolo [3,2, 1-des ] acridine (11-bromoo-13-chloro-5, 5-dimethyl-5H-benzo [ a ] indolo [3,2,1-de ] acridine) instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound g

Compound g was synthesized by the same method as the production method of compound a, using compound g-1 instead of compound a-1 and N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline.

3) Production of Compound 7

Compound g (20 g,27.6 mmol) and boron triiodide (16.2 g,41.4 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 4 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 7.1g of Compound 7. (yield 35%, MS: [ M+H) ] ⁺ ＝732)

Synthesis example 8

1) Production of Compound h-1

Compound H-1 was synthesized by the same method as the production method of compound a-1 using 4a,9a-dimethyl-2,3, 4a, 9a-hexahydro-1H-carbazole (4 a,9a-dimethyl-2,3, 4a,9 a-hexahydro-1H-carbazole) instead of 1- (tert-butyl) -4-iodobenzene and using 4-bromo-2-chloro-8, 8-dimethyl-8H-indolo [3,2, 1-des ] acridine (4-bromo-2-chloro-8, 8-dimethyl-8H-indolo [3,2,1-de ] acridine) instead of 2-chloro-4-methyl-9H-carbazole.

2) Production of Compound h

Compound h was synthesized by the same method as the production method of compound a, using compound h-1 instead of compound a-1.

3) Production of Compound 8

Compound h (20 g,26.2 mmol) and boron triiodide (15.4 g,39.4 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction for 2 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 6.7g of Compound 8. (yield 33%, MS: [ M+H)] ⁺ ＝770)

Synthesis example 9

1) Production of Compound i-1

Compound i-1 was synthesized by the same method as the production method of compound a-1 using 6- (tert-butyl) -2-chloro-4-methyl-9H-carbazole (6- (tert-butyl) -2-chloro-4-methyl-9H-carbazole) instead of 2-chloro-4-methyl-9H-carbazole and iodobenzene (iodobenzene) instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound i

Compound i-1 was used instead of compound a-1, use of 4- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) -10H-spiro [ acridine-9,9'-fluorene ] (4- (4, 5-tetramethy l-1,3, 2-dioxaab orolan-2-yl) -10H-spiro [ acridine-9,9' -fluorene ]) instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound i was synthesized by the same method as the production method of compound a.

3) Production of Compound 9

Compound i (20 g,31.1 mmol) and boron triiodide (18.3 g,46.7 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction for 6 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 8.7g of Compound 9. (yield 43%, MS: [ M+H)] ⁺ ＝651)

Synthesis example 10

1) Production of Compound j-2

Compound j-2 was synthesized by the same method as the production method of compound a using 4-bromo-6- (tert-butyl) -2-chloro-9H-carbazole (4-bromoo-6- (tert-butyl) -2-chloro-9H-carbazole) instead of compound a-1, using phenylboronic acid instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline.

2) Production of Compound j-1

Compound j-1 was synthesized by the same method as the production method of compound a-1, using compound j-2 instead of 2-chloro-4-methyl-9H-carbazole and 2-iododibenzo [ b, d ] thiophene instead of 1- (tert-butyl) -4-iodobenzene.

3) Production of Compound j

Compound j was synthesized by the same method as the production method of compound a, using compound j-1 instead of compound a-1 and N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline.

4) Production of Compound 10

Compound j (20 g,28.4 mmol) and boron triiodide (16.7 g,42.6 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 2 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 10.1g of compound 10. (yield 50%, MS: [ M+H)] ⁺ ＝713)

Synthesis example 11

1) Production of Compound k-2

Compound k-2 was synthesized by the same method as the production method of compound a using 1-bromo-3-chloro-7,7,10,10-tetramethyl-7, 8,9,10-tetrahydro-5H-benzo [ b ] carbazole (1-bromo-3-chloro-7,7,10,10-tetramethy l-7,8,9, 10-tetrahydroo-5H-benzob ] carbazole) instead of compound a-1 and using [1,1'-biphenyl ] -2-ylboronic acid ([ 1,1' -biphen ] -2-ylboronic acid) instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline.

2) Production of Compound k-1

Compound k-1 was synthesized by the same method as the production method of compound a-1 using compound k-2 instead of 2-chloro-4-methyl-9H-carbazole.

3) Production of Compound k

Using the compound k-1 instead of the compound a-1, using N- (4- (tert-butyl) phenyl) -3- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) dibenzo [ b, d ] furan-2-amine (N- (4- (tert-butyl) phenyl) -3- (4, 5-tetramethy-1, 3, 2-dioxab-oloan-2-yl) dibenzo [ b, d ] Furan-2-amine) was used instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, to synthesize compound k by the same method as the production method of compound a.

4) Production of Compound 11

Compound k (20 g,22.9 mmol) and boron triiodide (1)3.4g,34.3 mmol) was added to 200ml of 1, 2-dichlorobenzene and stirred at 160 ℃. After the reaction for 1 hour, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 9.5g of Compound 11. (yield 47%, MS: [ M+H)] ⁺ ＝883)

Synthesis example 12

1) Production of Compound l-2

Compound l-2 was synthesized by the same method as the production method of compound a, using 4-bromo-2-chloro-9H-carbazole instead of compound a-1, using [1,1'-biphenyl ] -2-ylboronic acid ([ 1,1' -biphenyl ] -2-ylboronic acid) instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline.

2) Production of Compound l-1

Compound l-1 was synthesized by the same method as the production method of compound a-1 using compound l-2 instead of 2-chloro-4-methyl-9H-carbazole.

3) Production of Compound I

Compound l-1 was used instead of compound a-1, N- (4- (tert-butyl) phenyl) -7,7,10,10-tetramethyl-3- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) -7,8,9,10-tetrahydrobenzo [ b ] naphtho [2,3-d ] thiophen-2-amine (N- (4- (tert-butyl) phenyl) -7,7,10,10-tetramethy l-3-; 4, 5-tetramethy-1, 3, 2-dioxaborolan-2-yl) -7,8,9, 10-tetrahydrob-nano-2, 3-d-thiophen-2-amine instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound i was synthesized by the same method as the production method of compound a.

4) Production of Compound 12

Compound l (20 g,22.4 mmol) and boron triiodide (13.2 g,33.7 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 3 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to give 7.9g of a compound12. (yield 39%, MS: [ M+H)] ⁺ ＝899)

Synthesis example 13

1) Production of Compound m-1

Compound m-1 was synthesized by the same method as the production method of compound a-1 using 9-chloro-11-methyl-7H-benzo [ c ] carbazole (9-chloro-11-methyl-7H-benzozo [ c ] ca rbazole) instead of 2-chloro-4-methyl-9H-carbazole.

2) Production of Compound m

Compound m-1 was used instead of compound a-1, N- (4- (tert-butyl) phenyl) -9,9-dimethyl-2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) -9H-fluoren-3-amine (N- (4- (tert-b utyl) phenyl) -9,9-dimethyl-2- (4, 5) -tetramethyl-1,3, 2-dioxaborolan-2-yl) -9H-fluoroen-3-amine instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound m was synthesized by the same method as the production method of compound a.

3) Production of Compound 13

Compound m (20 g,28.4 mmol) and boron triiodide (16.7 g,42.7 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 3 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 8.7g of Compound 13. (yield 43%, MS: [ M+H)] ⁺ ＝711)

Synthesis example 14

1) Production of Compound n-1

Compound n-1 was synthesized by the same method as the production method of compound a-1 using 1- (tert-butyl) -3-chloro-7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo [ b ] carbazole (1- (tert-butyl) -3-chloro-7,7,10,10-tetramethy l-7,8,9, 10-tetrahydroo-5H-benzob ] carbazole) instead of 2-chloro-4-methyl-9H-carbazole.

2) Production of Compound n

Compound N-1 was used instead of compound a-1, N- (4- (tert-butyl) phenyl) -7,7,10,10-tetramethyl-2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) -7,8,9,10-tetrahydronaphtho [2,3-b ] benzofuran-3-amine (N- (4- (tert-butyl) phenyl) -7,7,10,10-tetramethy l-2- (4, 5) -tetramethyl-1,3, 2-dioxaborolan-2-yl) -7,8,9, 10-tetrahydrononapoh [2,3-b ] benzofuran-3-amine instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound N was synthesized by the same method as the production method of compound a.

3) Production of Compound 14

Compound n (20 g,22.5 mmol) and boron triiodide (13.2 g,33.7 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction was carried out for 7 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 8.3g of Compound 14. (yield 41%, MS: [ M+H)] ⁺ ＝898)

Synthesis example 15

1) Production of Compound o-2

Compound o-2 was synthesized by the same method as the production method of compound a, using 1-bromo-3-chloro-5H-benzo [ b ] carbazole instead of compound a-1, using phenylboronic acid instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline.

2) Production of Compound o-1

Compound o-1 was synthesized by the same method as the production method of compound a-1 using compound o-2 instead of 2-chloro-4-methyl-9H-carbazole.

3) Production of Compound o

Using the compound o-1 instead of the compound a-1, using N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) dibenzo [ b, d ] thiophen-3-amine (N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethy-1, 3, 2-dioxaborolan-2-yl) dib-zo [ b ], d ] thiophen-3-amine) instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound o was synthesized by the same method as the production method of compound a.

4) Production of Compound 15

Compound o (20 g,26.5 mmol) and boron triiodide (15.6 g,39.7 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction was carried out for 5 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography, whereby 9.7g of compound 15 was produced. (yield 48%, MS: [ M+H)] ⁺ ＝763)

Synthesis example 16

1) Production of Compound p-1

Compound p-1 was synthesized by the same method as the production method of compound a-1 using 6- (tert-butyl) -2-chloro-4-methyl-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole.

2) Production of Compound p

Compound p-1 was used instead of compound a-1, N- (4- (tert-butyl) phenyl) -9,9-dimethyl-3- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) -9H-fluoren-2-amine (N- (4- (tert-butyl) phenyl) -9,9-dimethyl-3- (4, 5) -tetramethyl-1,3, 2-dioxaboom-2-yl) -9H-fluoroen-2-amine instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound p was synthesized by the same method as the production method of compound a.

3) Production of Compound 16

Compound p (20 g,28.2 mmol) and boron triiodide (16.6 g,42.3 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 2 hours of reaction, the mixture is cooled to normal temperature and extracted, and then a silica gel column layer is usedThe reaction mixture was purified by chromatography to obtain 7.7g of Compound 16. (yield 38%, MS: [ M+H)] ⁺ ＝717)

Synthesis example 17

1) Production of Compound q-1

Compound q-1 was synthesized by the same method as the production method of compound a-1 using 5-chloro-7H-benzo [ c ] carbazole (5-chloro-7H-benzo [ c ] carbazole) instead of 2-chloro-4-methyl-9H-carbazole.

2) Production of Compound q

Compound q was synthesized by the same method as the production method of compound a, using compound q-1 instead of compound a-1 and N- (4- (tert-butyl) phenyl) -9,9-dimethyl-3- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) -9H-fluoren-2-amine instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline.

3) Production of Compound 17

Compound q (20 g,29 mmol) and boron triiodide (17 g,43.5 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen and stirred at 160 ℃. After the reaction for 2 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 9.3g of Compound 17. (yield 46%, MS: [ M+H)] ⁺ ＝697)

Synthesis example 18

1) Production of Compound r-2

Compound r-2 was synthesized by the same method as the production method of compound a-1, using 4-bromo-2-chloro-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole and 5- (tert-butyl) -3-iodobenzofuran (5- (tert-butyl) -3-iodobenzofuran) instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound r-1

Compound r-1 was synthesized by the same method as the production method of compound a-1 using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound r-2 instead of 1- (tert-butyl) -4-iodobenzene.

3) Production of Compound r

Compound r was synthesized by the same method as the production method of compound a, using compound r-1 instead of compound a-1 and N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline.

4) Production of Compound 18

Compound r (20 g,27.4 mmol) and boron triiodide (16.1 g,41.1 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction for 1 hour, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 8.5g of Compound 18. (yield 42%, MS: [ M+H)] ⁺ ＝738)

Synthesis example 19

1) Production of Compound s-2

Compound s-2 was synthesized by the same method as the production method of compound a-1 using 4-bromo-6- (tert-butyl) -2-chloro-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole and 3-iodo-5, 8-tetramethyl-5,6,7,8-tetrahydronaphtho [2,3-b ] thiophene (3-iodo-5, 8-tetramethy-5, 6,7, 8-tetrahydroapatho [2,3-b ] thiophene) instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound s-1

Compound s-1 was synthesized by the same method as the production method of compound a-1 using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound s-2 instead of 1- (tert-butyl) -4-iodobenzene.

3) Production of Compound s

Compound s was synthesized by the same method as the production method of compound a, using compound s-1 instead of compound a-1 and N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline.

4) Production of Compound 19

Compounds s (20 g,23.4 mmol) and boron triiodide (13.7 g,35 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen and stirred at 160 ℃. After 3 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 8.3g of Compound 19. (yield 41%, MS: [ M+H)] ⁺ ＝864)

Synthesis example 20

1) Production of Compound t-2

Compound t-2 was synthesized by the same method as the production method of compound a-1 using 4-bromo-2-chloro-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole and 3-iodo-5-phenylbenzo [ b ] thiophene (3-iodoo-5-phenylbenzob ] thiophen) instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound t-1

Compound t-1 was synthesized by the same method as the production method of compound a-1 using diphenylamine instead of 2-chloro-4-methyl-9H-carbazole and compound t-2 instead of 1- (tert-butyl) -4-iodobenzene.

3) Production of Compound t

Compound t-1 was used instead of compound a-1, use of N- (4- (tert-butyl) phenyl) -6,6,9,9,11,11-hexamethyl-3- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) -7,8,9,11-tetrahydro-6H-benzo [ b ] fluoren-2-amine (N- (4- (tert-butyl) phenyl) -6,6,9,9,11,11-hexa-methyl-3- (4, 5) -tetramethyl-1,3, 2-dioxaborolan-2-yl) -7,8,9, 11-tetrahydro-6H-benzoen-2-amine instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound t was synthesized by the same method as the production method of compound a.

4) Production of Compound 20

Compound t (20 g,20.2 mmol) and boron triiodide (11.8 g,30.2 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction was carried out for 2 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 7.5g of Compound 20. (yield 37%, MS: [ M+H)] ⁺ ＝1000)

Synthesis example 21

1) Production of Compound u-2

Compound u-2 was synthesized by the same method as the production method of compound a using 4-bromo-6- (tert-butyl) -2-chloro-9H-carbazole instead of compound a-1 and (4- (tert-butyl) phenyl) boronic acid instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline.

2) Production of Compound u-1

Use of the Compound u-2 instead of 2-chloro-4-methyl-9H-carbazole, 5-bromo-2-phenylbenzo [ d ]]Azole (5-bromoo-2-phenylbenzol [ d ]]oxazole) was used in place of 1- (tert-butyl) -4-iodobenzene to synthesize compound u-1 by the same method as the production method of compound a-1.

3) Production of Compound u

Compound u-1 was used instead of compound a-1, use of 7,7,10,10-tetramethyl-2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -N- (5, 8-tetramethyl-5,6,7, 8-tetrahydronaphthalen-2-yl) -7,8,9,10-tetrahydronaphtho [2,3-b ] benzofuran-3-amine (7,7,10,10-tetramethy-2- (4, 5-te-trameth-yl-1, 3,2 ] Dioxabolan-2-yl) -N- (5, 8-tetramethyl-5,6,7,8-tetrahydron aphthalen-2-yl) -7,8,9, 10-tetrahydronoaphtha [2,3-b ] benzofuran-3-amine) replaces 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline, compound u was synthesized by the same method as the production method of compound a.

4) Production of Compound 21

Compound u (20 g,19.5 mmol) and boron triiodide (11.4 g,29.2 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 5 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 9.9g of Compound 21. (yield 49%, MS: [ M+H)] ⁺ ＝1035)

Synthesis example 22

1) Production of Compound v-1

Compound v-1 was synthesized by the same method as the production method of compound a-1 using 9-chloro-11-methyl-7H-benzo [ c ] carbazole instead of 2-chloro-4-methyl-9H-carbazole and 3-bromo-5-phenylbenzofuran (3-bromoo-5-phenylbenzofuran) instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound v

Use of Compound v-1 instead of Compound a-1, use of N ¹ ,N ¹ -diphenyl-4- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -N ³ - (5, 8-tetramethyl-5,6,7, 8-tetrahydronaphthalen-2-yl) benzene-1, 3-diamine (N ¹ ,N ¹ -diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N ³ - (5, 8-tetramethy-5, 6,7, 8-tetrahydroaphthalen-2-yl) benzene-1, 3-diamine) instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline, compound v was synthesized by the same method as the production method of compound a.

3) Production of Compound 22

Compound v (20 g,23 mmol) and boron triiodide (13.5 g,34.6 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 4 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography6.9g of compound 22 was thus produced. (yield 34%, MS: [ M+H)] ⁺ ＝876)

Synthesis example 23

1) Production of Compound w-2

Compound w-2 was synthesized by the same method as the production method of compound a-1, using 4-bromo-2-chloro-9H-carbazole instead of 2-chloro-4-methyl-9H-carbazole and 2-iododibenzo [ b, d ] thiophene instead of 1- (tert-butyl) -4-iodobenzene.

2) Production of Compound w-1

Use of 10H-phenonesThe compound w-1 was synthesized by the same method as the production method of the compound a-1, using the compound w-2 instead of 1- (tert-butyl) -4-iodobenzene instead of 2-chloro-4-methyl-9H-carbazole with the oxazine (10H-phenoxazine).

3) Production of Compound w

Compound w-1 was used instead of compound a-1, 1- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) -9H-carbazole (1- (4, 5-tetramethy l-1,3, 2-dioxaborolan-2-yl) -9H-carbazole) instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) aniline, compound w was synthesized by the same method as the production method of compound a.

4) Production of Compound 23

Compound w (20 g,28.7 mmol) and boron triiodide (16.9 g,43.1 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction for 2 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 7.5g of Compound 23. (yield 37%, MS: [ M+H)] ⁺ ＝704)

Synthesis example 24

1) Production of Compound x-2

Using 7-bromo-9-chloro-11H-benzo [ a ]]Carbazole is used instead of compound a-1 (phenyl-d) ₅ ) Boric acid ((phenyl-d) ₅ ) The compound x-2 was synthesized by the same method as the production method of the compound a, instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline.

2) Production of Compound x-1

Compound x-1 was synthesized by the same method as the production method of compound a-1 using compound x-2 instead of 2-chloro-4-methyl-9H-carbazole.

3) Production of Compound x

Compound x was synthesized by the same method as the production method of compound a, using compound x-1 instead of compound a-1 and N- (4- (tert-butyl) phenyl) -9, 9-dimethyl-3- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -9H-fluoren-2-amine instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline.

4) Production of Compound 24

Compound x (20 g,26 mmol) and boron triiodide (15.3 g,39 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After 5 hours of reaction, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 6.7g of compound 24. (yield 33%, MS: [ M+H)] ⁺ ＝778)

Synthesis example 25

1) Production of Compound y-2

Use of 4-bromo-2-chloro-9H-carbazole instead of compound a-1, (phenyl-d ₅ ) Preparation of boric acid in place of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline by reaction with Compound aThe compound y-2 was synthesized in the same manner as the production method.

2) Production of Compound y-1

Compound y-1 was synthesized by the same method as the production method of compound a-1, using compound y-2 instead of 2-chloro-4-methyl-9H-carbazole and 3-bromo-5, 8-tetramethyl-5,6,7, 8-tetrahydronaphtho [2,3-b ] thiophene (3-bromoo-5, 8-tetramethyl-5,6,7,8-tetrahydr onaphtho [2,3-b ] thiopene) instead of 1- (tert-butyl) -4-iodobenzene.

3) Production of Compound y

Compound y was synthesized by the same method as the production method of compound a, using compound y-1 instead of compound a-1 and N- (4- (tert-butyl) phenyl) -9, 9-dimethyl-3- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -9H-fluoren-2-amine instead of 4- (tert-butyl) -N- (4- (tert-butyl) phenyl) -2- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline.

4) Production of Compound 25

Compound y (20 g,24.1 mmol) and boron triiodide (14.1 g,36.1 mmol) were added to 200ml of 1, 2-dichlorobenzene under nitrogen atmosphere and stirred at 160 ℃. After the reaction for 5 hours, the mixture was cooled to room temperature, extracted, and purified by silica gel column chromatography to obtain 7.1g of compound 25. (yield 35%, MS: [ M+H)] ⁺ ＝838)

Examples

To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. In addition, oxygen plasma is utilized to makeAfter the substrate was cleaned for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.

On the ITO transparent electrode thus prepared, the following HI-A and HAT-CN were respectively used as And performing thermal vacuum evaporation to form first and second hole injection layers. On the hole injection layer, HT-A as described below is added +.>Vacuum deposition is performed to form a hole transport layer. On the hole transport layer, HT-B as described below is added +.>And vacuum evaporation is performed to form an electron blocking layer. Next, 4 parts by weight of the compound 1 of synthesis example 1 as a blue light-emitting dopant based on 100 parts by weight of the light-emitting layer was vacuum-deposited on the electron blocking layer, and the following BH-a as a main component was ∈ ->And vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer. Then, on the light-emitting layer, as a first electron transport layer, the following compound ET-A was vacuum-evaporated +.>Next, the following ET-B and LiQ were vacuum evaporated at a weight ratio of 1:1 to give +.>Forming a second electron transport layer. Vacuum evaporating LiQ on the second electron transport layer to obtain +.>And vacuum vapor deposition is performed to form an electron injection layer. On the electron injection layer, by +.>Aluminum and silver were vapor deposited at a weight ratio of 10:1, and aluminum was added thereto at +.>And the thickness of the metal layer is evaporated to form a cathode.

In the above process, the vapor deposition rate of the organic matter is maintained Aluminum maintenance of cathode/sec->Vapor deposition rate per second, vacuum degree was maintained at 1×10 during vapor deposition ^-7 ～5×10 ^-8 The support is thus fabricated into an organic light emitting device. />

Comparative example substance

Examples 2 to 25

An organic light-emitting device was fabricated by the same method as in example 1 above, except that the compounds of table 1 below were used as dopants of the light-emitting layer instead of the compound 1 above.

Comparative examples 1 to 5

An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compounds described in table 1 below were used in place of the compound 1 in the organic light-emitting device of example 1.

When a current was applied to the organic light emitting devices manufactured in examples 1 to 25 and comparative examples 1 to 5, the voltage, efficiency, and lifetime were measured (based on 6000 nits), and the results are shown in table 1 below. Lifetime T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

TABLE 1

In table 1 above, it is known that the organic light emitting device according to an embodiment of the present specification is excellent in voltage, light emitting efficiency, and lifetime as compared with the organic light emitting devices of comparative examples 1 to 5.

Specifically, the organic light emitting devices of examples 1 to 25 according to an embodiment of the present specification include substituents other than hydrogen in Z1 to stabilize the structure to prevent generation of unstable portions, and the efficiency of the organic light emitting device can be improved. Therefore, it was confirmed that the driving voltage, the light-emitting efficiency and the lifetime were excellent as compared with the organic light-emitting layer devices of comparative examples 1 to 4 using the above-mentioned compound in which Z1 is hydrogen.

In addition, the compounds of comparative examples 3 to 5 in which A1 and R1 described above are bonded to each other to form a ring have many rapid degradation (degradation) portions, and the driving voltage increases based on the characteristic that the organic light emitting device depends on intermolecular hopping (hoping).

However, if the unstable moiety (A1 and R1 are bonded to each other to form a ring) is eliminated as in the compound of chemical formula 1 in the present specification, electron and hole injection is reduced to suppress Quenching (Quenching) and degradation, and thus the efficiency of the organic light emitting device is improved, the lifetime of the device is improved, and the voltage is also reduced. Therefore, it was confirmed that the organic light emitting devices of examples 1 to 25 according to an embodiment of the present specification were excellent in driving voltage, light emitting efficiency, and lifetime as compared with comparative examples 3 to 5.

Claims

1. A compound of the following chemical formula 1:

[ chemical formula 1]

In the chemical formula 1 described above, a compound having the formula,

a2 is a substituted or unsubstituted hydrocarbon ring,

the A1 and A2 are combined with each other to form a substituted or unsubstituted ring or not,

r1 and R2 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G1) (G2), substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or any one or more pairs of adjacent ones of the R1 and R2 are bonded to each other to form a substituted or unsubstituted ring,

2. The compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 2 to 6:

[ chemical formula 2]

[ chemical formula 3]

[ chemical formula 4]

[ chemical formula 5]

[ chemical formula 6]

In the chemical formulas 2 to 6 described above,

a1, R1, R2, R1, R2, Z1 and Z2 are as defined in said formula 1,

r3 to R6 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G5) (G6), substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, any one or more of the R3 to R6 and the A1 being combined with each other to form a substituted or unsubstituted ring,

3. The compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 7 to 9:

[ chemical formula 7]

[ chemical formula 8]

[ chemical formula 9]

In the chemical formulas 7 to 9 described above,

a1, R1, R2, R1, R2, Z1 and Z2 are as defined in said formula 1,

r7 is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G5) (G6), substituted or unsubstituted aryl, a fused ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or is combined with the A1 to form a substituted or unsubstituted ring,

4. The compound of claim 1, wherein A1 is a substituted or unsubstituted aromatic hydrocarbon ring; condensed rings of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring containing 1 or more of O, N, S and Si.

5. The compound of claim 1, wherein the chemical formula 1 is the following chemical formula 10 or 11:

[ chemical formula 10]

[ chemical formula 11]

In the chemical formulas 10 and 11 described above,

a2, R1, R2, R1, R2, Z1 and Z2 are as defined in the chemical formula 1,

x1 is-C (R13) (R14) -, -Si (R15) (R16) -, -O-, or-S-,

r11 to R16 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted silyl, -N (G7) (G8), substituted or unsubstituted aryl, a condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heterocyclic group, or any one or more pairs of adjacent ones of the R11 to R16 are bonded to each other to form a substituted or unsubstituted ring,

said R11 and said A2 are bonded to each other to form a substituted or unsubstituted ring, or to form no ring,

Said R12 and said A2 are bonded to each other to form a substituted or unsubstituted ring, or to form no ring,

6. The compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 12 to 23:

[ chemical formula 12]

[ chemical formula 13]

[ chemical formula 14]

[ chemical formula 15]

[ chemical formula 16]

[ chemical formula 17]

[ chemical formula 18]

[ chemical formula 19]

[ chemical formula 20]

[ chemical formula 21]

[ chemical formula 22]

[ chemical formula 23]

In the chemical formulas 12 to 23 described above,

a2, R1, R2, R1, R2, Z1 and Z2 are as defined in the chemical formula 1,

x1 is-C (R13) (R14) -, -Si (R15) (R16) -, -O-, or-S-,

r '11 is an integer of 1 to 4, and when R '11 is 2 or more, the 2 or more R '11 are the same or different from each other,

r '11 is an integer of 1 to 3, and when the R '11 is 2 or more, the 2 or more R '11 are the same or different from each other,

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

7. The compound of claim 1, wherein A1 is a monocyclic or polycyclic aromatic hydrocarbon ring of 6 to 30 carbon atoms substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl of 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl of 3 to 30 carbon atoms, a linear or branched alkylsilyl of 1 to 30 carbon atoms, -N (G7) (G8), a monocyclic or polycyclic aryl of 6 to 30 carbon atoms, a monocyclic or polycyclic heterocyclyl of 2 to 30 carbon atoms, and combinations thereof; condensed rings 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring containing 2 to 30 carbon atoms of 1 or more of O, N and S, which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl group of 1 to 30 carbon atoms, -N (G7) (G8), a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms, and combinations thereof,

The A2 is a monocyclic or polycyclic aromatic hydrocarbon ring of 6 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group of 1 to 30 carbon atoms, -N (G5) (G6), or a monocyclic or polycyclic aryl group of 6 to 30 carbon atoms; or a condensed ring 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, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms,

the A1 and A2 are combined with each other to form or not to form a mono-or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is substituted or unsubstituted by 1 or more selected from the group consisting of a linear or branched alkyl having 1 to 30 carbon atoms, a mono-or polycyclic aryl having 6 to 30 carbon atoms, and a combination thereof,

the R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, -N (G1) (G2), a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or any one or more adjacent pairs of R1 and R2 are bonded to each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; condensed rings 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, which are substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms which is substituted or unsubstituted with 1 or more selected from the group consisting of a linear or branched alkyl having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl having 6 to 30 carbon atoms, and a combination thereof,

The Z1 is a linear or branched alkyl group having 1 to 30 carbon atoms which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; -N (G3) (G4); substituted or unsubstituted monocyclic or polycyclic aryl group of 6 to 30 carbon atoms with deuterium, linear or branched alkyl group of 1 to 30 carbon atoms, or monocyclic or polycyclic aryl group of 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms which is bonded to Z2,

when Z2 and Z1 are bonded to each other without forming a ring, Z2 is hydrogen,

the G1 to G8 are the same or different from each other and each independently is a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

8. The compound of claim 1, wherein the chemical formula 1 is any one of the following compounds:

In the compounds mentioned, t-Bu refers to tert-butyl.

9. An organic light emitting device, comprising: a first electrode, a second electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 8.

10. The organic light-emitting device of claim 9, wherein the organic layer comprises a light-emitting layer comprising the compound.

11. The organic light-emitting device of claim 9, wherein the organic layer comprises a light-emitting layer comprising a dopant species comprising the compound.

12. The organic light-emitting device of claim 9, wherein the organic layer comprises a light-emitting layer further comprising a compound of formula H:

[ chemical formula H ]

In the chemical formula H described above, the amino acid sequence,

13. An organic light emitting device according to claim 11 wherein the light emitting layer further comprises more than 1 dopant and a host.

14. The organic light-emitting device according to claim 11, wherein the light-emitting layer further comprises 1 or more hosts.

15. The organic light-emitting device of claim 11, wherein the light-emitting layer further comprises more than 2 hybrid hosts.