KR101830709B1 - Hetero-cyclic compound and organic light emitting device using the same - Google Patents

Abstract

The present invention provides a heterocyclic compound capable of greatly improving the lifetime, efficiency, electrochemical stability, and thermal stability of an organic light emitting device, and an organic light emitting device in which the heterocyclic compound is contained in an organic compound layer.

Description

HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME [0002]

This application claims the benefit of Korean Patent Application No. 10-2015-0155886 filed with the Korean Intellectual Property Office on Nov. 6, 2015, the entire contents of which are incorporated herein by reference.

The present invention relates to a heterocyclic compound and an organic light emitting device using the same.

An electroluminescent device is one type of self-luminous display device, and has advantages of wide viewing angle, excellent contrast, and high response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if necessary.

The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used. In addition, as the material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc. may be used.

In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

U.S. Patent No. 4,356,429

A compound having a chemical structure capable of satisfying the conditions required for a material usable in an organic light emitting device, for example, an appropriate energy level, electrochemical stability and thermal stability, The organic light-emitting device is required to be studied.

An embodiment of the present application provides a heterocyclic compound represented by any one of the following formulas (1) to (3):

[Chemical Formula 1]

(2)

(3)

In the above Formulas 1 to 3,

Ar 1 to Ar 6 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

R1 to R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group of; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R "; and -P (= O) RR ', and substituted or unsubstituted C ₁ to C ₂₀ alkyl groups, substituted or unsubstituted C ₆ to C ₆₀ aryl groups, or C ₂ to C ₆₀ heteroaryl groups. And an unsubstituted amine group,

Substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, A substituted or unsubstituted C ₆ to C ₆₀ aryl group or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

m, n, o, p, q, r, s, t and u are each independently an integer of 0 to 4;

Another embodiment of the present application is an organic light emitting device comprising a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers is represented by any one of Formulas 1 to 3 And a heterocyclic compound which is capable of reacting with an organic compound.

Another embodiment of the present application provides an organic light-emitting device, wherein the organic compound layer containing the heterocyclic compound further comprises a compound represented by the following formula (4) or (5):

[Chemical Formula 4]

In Formula 4,

And L1 and L2 are the same or different and are each independently a direct bond or a substituted or unsubstituted C ₆ to C ₆₀ arylene group of one another,

Ar7 is a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group containing at least one N,

Ar8 is represented by the following formula (6) or (7)

[Chemical Formula 6]

(7)

Y1 to Y4 are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aromatic hydrocarbon ring; Or a substituted or unsubstituted C ₂ to C ₆₀ aromatic heterocycle,

R10 to R16 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group of; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R "; and -P (= O) RR ', and substituted or unsubstituted C ₁ to C ₂₀ alkyl groups, substituted or unsubstituted C ₆ to C ₆₀ aryl groups, or C ₂ to C ₆₀ heteroaryl groups. Or an unsubstituted amine group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

Substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, A substituted or unsubstituted C ₆ to C ₆₀ aryl group or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

[Chemical Formula 5]

In Formula 5,

At least one of X1 to X3 is N, and the others are each independently N or CR35,

R17, R18 and R35 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group of; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R "; and -P (= O) RR ', and substituted or unsubstituted C ₁ to C ₂₀ alkyl groups, substituted or unsubstituted C ₆ to C ₆₀ aryl groups, or C ₂ to C ₆₀ heteroaryl groups. Or an unsubstituted amine group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

R19 to R21, and R27 to R30 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group of; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R "; and -P (= O) RR ', and substituted or unsubstituted C ₁ to C ₂₀ alkyl groups, substituted or unsubstituted C ₆ to C ₆₀ aryl groups, or C ₂ to C ₆₀ heteroaryl groups. And an unsubstituted amine group,

R31 to R34 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group of; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R "; and -P (= O) RR ', and substituted or unsubstituted C ₁ to C ₂₀ alkyl groups, substituted or unsubstituted C ₆ to C ₆₀ aryl groups, or C ₂ to C ₆₀ heteroaryl groups. Or an unsubstituted amine group, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,

At least one of R22 to R26 is -CN and the others are each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group of; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R "; and -P (= O) RR ', and substituted or unsubstituted C ₁ to C ₂₀ alkyl groups, substituted or unsubstituted C ₆ to C ₆₀ aryl groups, or C ₂ to C ₆₀ heteroaryl groups. Or an unsubstituted amine group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

Substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, A substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group.

The heterocyclic compound according to one embodiment of the present application can be used as an organic material layer material of an organic light emitting device. The heterocyclic compound can be used as a material for a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer in an organic light emitting device. In particular, the heterocyclic compound represented by any one of formulas 1 to 3 may be used as an electron transport layer, a hole transport layer, or a material of a light emitting layer of an organic light emitting device. When the heterocyclic compound represented by any one of Chemical Formulas 1 to 3 is used for an organic light emitting device, the driving voltage of the device may be lowered, the light efficiency may be improved, and the lifetime characteristics of the device may be improved by thermal stability of the compound .

In particular, the organic light emitting device according to one embodiment of the present application includes a heterocyclic compound represented by any one of formulas (1) to (3) as a host material of a light emitting layer; And the compound represented by the general formula (4) or (5) at the same time, the organic EL device of the present invention can exhibit significantly improved driving efficiency, lifetime,

FIGS. 1 to 3 schematically show a stacked structure of organic light emitting devices according to one embodiment of the present application.

The present application will be described in detail below.

The heterocyclic compound according to one embodiment of the present application is characterized by being represented by any one of the above formulas (1) to (3). More specifically, the heterocyclic compound represented by any one of Chemical Formulas 1 to 3 may be used as an organic material layer material of an organic light emitting device according to the structural features of the core structure and the substituent.

In one embodiment of the present application, R 1 to R 9 in the above formulas (1) to (3) may each independently be hydrogen or deuterium.

In the present application, the substituents of the above formulas will be described in more detail as follows.

As used herein, the term "substituted or unsubstituted" A halogen group; -CN; A C ₁ to C ₆₀ alkyl group; A C ₂ to C ₆₀ alkenyl group; An alkynyl group of C ₂ to C ₆₀ ; A C ₃ to C ₆₀ cycloalkyl group; A C ₂ to C ₆₀ heterocycloalkyl group; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heteroaryl group; -SiR ' R "; -P (= O) RR '; C ₁ to C ₂₀ alkylamine groups; C ₆ to C ₆₀ arylamine groups; And a heteroarylamine group having from ₂ to ₆₀ carbon atoms, or substituted or unsubstituted with a substituent having two or more of the substituents bonded thereto, or two or more substituents selected from the above substituents are connected to each other Quot; means substituted or unsubstituted with a substituent. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected. The additional substituents may be further substituted. A substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, An alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group.

According to one embodiment of the present application, the "substituted or unsubstituted" refers to a group selected from the group consisting of deuterium, a halogen group, -CN, SiRR'R ", P (═O) RR ', a C ₁ to C ₂₀ linear or branched alkyl group , A C ₆ to C ₆₀ aryl group, and a C ₂ to C ₆₀ heteroaryl group,

A halogen atom, -CN, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₆₀ aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, and C ₂ to C ₆₀ substituted heteroaryl or unsubstituted alkyl group of C ₁ to C _60; an aryl group of deuterium, halogen, -CN, C ₁ to C ₂₀ alkyl group, C ₆ to C ₆₀ a, and C ₂ to a substituted or unsubstituted group of the C ₆₀ heteroaryl C ₃ to C ₆₀ cycloalkyl group; a deuterium, a halogen, -CN, an alkyl group of C ₁ to C _20, C ₆ to C ₆₀ aryl, and C ₂ to C ₆₀ substituted or unsubstituted group heteroaryl C ₆ to C ₆₀ aryl group; or an alkyl group of deuterium, halogen, -CN, C ₁ to C _20, C ₆ to C ₆₀ aryl, and C ₂ to C ₆₀ the heteroaryl group is a heteroaryl group, a substituted or unsubstituted C ₂ to C _60.

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

In the present specification, the halogen may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group includes a straight chain or a branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, An n-pentyl group, a tert-butyl group, a tert-butyl group, a 3-methylbutyl group, a 3-methylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but is not limited thereto.

In the present specification, the alkenyl group includes a straight chain or a branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.

In the present specification, the alkynyl group includes a straight chain or a branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, the cycloalkyl group includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted by other substituents. Herein, the term "polycyclic" means a group in which a cycloalkyl group is directly connected to another ring group or condensed therewith. Here, the other ring group may be a cycloalkyl group, but may be another ring group such as a heterocycloalkyl group, an aryl group, a heteroaryl group and the like. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more particularly 5 to 20. Specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, , 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but are not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which the heterocycloalkyl group is directly connected to another ring group or condensed. Here, the other ring group may be a heterocycloalkyl group, but may be another ring group such as a cycloalkyl group, an aryl group, a heteroaryl group and the like. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

In the present specification, the aryl group includes monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be further substituted by other substituents. Herein, a polycyclic ring means a group in which an aryl group is directly connected to another ring group or condensed with another ring group. Here, the other ring group may be an aryl group, but may be another kind of ring group such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group and the like. The aryl group includes a spiro group. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a klychenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, An acenaphthyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, a condensed ring group thereof, a thiophenecarbonyl group, , But are not limited thereto.

In the present specification, the spiro group is a group including a spiro structure and may have from 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro groups may include any of the groups of the following structural formulas.

In the present specification, the heteroaryl group includes S, O, Se, N or Si as a hetero atom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Herein, the polycyclic ring means a group in which the heteroaryl group is directly connected to another ring group or condensed therewith. Here, the other ring group may be a heteroaryl group, but may be another ring group such as a cycloalkyl group, a heterocycloalkyl group, an aryl group and the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 3 to 25 carbon atoms. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, A thiazolyl group, a thiazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a paranyl group, a thiopyranyl group, a diazinyl group, , A thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinolizolyl group, a naphthyridyl group, An imidazopyridinyl group, a diazanaphthalenyl group, a triazinediyl group, an indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophenyl group, a benzothiophenyl group , A dibenzothiophene group, a dibenzofuran group, a carbazolyl group, a benzocarbazolyl group, (Dibenzosilyl), dihydrophenazinyl, phenoxazinyl, phenanthridyl, imidazopyridinyl, thienyl, indolo [3,3-d] pyrimidinyl, 2,3-a] carbazolyl group, indolo [2,3-b] carbazolyl group, indolinyl group, 10,11-dihydrodibenzo [b, f] azepine group, 9,10-dihydro A phenanthrolinyl group, a phenanthrazinyl group, a phenothiatriazinyl group, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo [c] [1,2,5] thiadiazolyl group, 1,5-c] quinazolinyl group, pyrido [l, 2-b] indazolyl group, pyrido [l, 2- a] imidazo [1,2-e] indolinyl group, and 5,11-dihydroindeno [1,2-b] carbazolyl group.

In the present specification, the amine group is a monoalkylamine group; Monoarylamine groups; A monoheteroarylamine group; -NH ₂ ; A dialkylamine group; A diarylamine group; A diheteroarylamine group; Alkylarylamine groups; Alkylheteroarylamine groups; And an arylheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a diphenylamine group, an anthracenylamine group, A phenylphenylamine group, a diphenylamine group, a methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, Naphthylamine amine group, phenylnaphthylamine amine group, phenylnaphthylamine amine group, biphenyltriphenylenylamine group, and the like.

In the present specification, an arylene group means a group having two bonding positions in an aryl group, that is, a divalent group. The description of the aryl group described above can be applied except that each of these is 2 groups. Further, the heteroarylene group means that the heteroaryl group has two bonding positions, i.e., divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

According to one embodiment of the present application, the compound represented by any one of Chemical Formulas 1 to 3 may be represented by any one of the following compounds, but is not limited thereto.

In addition, by introducing various substituents into the structures of any one of formulas (1) to (3) above, it is possible to synthesize a compound having the intrinsic property of a substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Further, by introducing various substituents into the structure of any one of formulas (1) to (3), it is possible to finely control the energy band gap, while improving the characteristics at the interface between organic materials, can do.

On the other hand, the above-mentioned heterocyclic compound has a high glass transition temperature (Tg) and thus is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.

The heterocyclic compound according to one embodiment of the present application can be prepared by a multistage chemical reaction. Some intermediate compounds may be prepared first, and compounds of any of formulas 1-3 may be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application can be prepared on the basis of the following production example.

One embodiment of the present application provides an organic light emitting device comprising a compound represented by any one of Chemical Formulas 1 to 3 above.

Another embodiment of the present application is an organic light emitting device comprising a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein the organic layer includes a light emitting layer, A heterocyclic compound represented by one; And a compound represented by the formula (4) or (5).

In the above formulas (6) and (7), * represents the position connected to L2 in the above formula (4).

According to one embodiment of the present application, the formula (6) may be represented by any one of the following formulas.

In the above structural formulas, X 1 to X 6 are the same or different and each independently NR, S, O or CR'R "

R8 to R14 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group of; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R "; and -P (= O) RR ', and substituted or unsubstituted C ₁ to C ₂₀ alkyl groups, substituted or unsubstituted C ₆ to C ₆₀ aryl groups, or C ₂ to C ₆₀ heteroaryl groups. Or an unsubstituted amine group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

Substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, A substituted or unsubstituted C ₆ to C ₆₀ aryl group or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

m, n, o, p, q, r and s are each independently an integer of 0 to 6;

According to one embodiment of the present application, the formula (7) can be represented by any one of the following formulas.

X7 and X8 are the same or different and are each independently NR, S, O or CR'R "

R15 to R18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C ₁ to C ₆₀ alkyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkenyl group; A substituted or unsubstituted C ₂ to C ₆₀ alkynyl group; A substituted or unsubstituted C ₁ to C ₆₀ alkoxy group; A substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group; Substituted or unsubstituted C ₂ to C ₆₀ heterocycloalkyl group of; A substituted or unsubstituted C ₆ to C ₆₀ aryl group; A substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group; -SiRR'R "; and -P (= O) RR ', and substituted or unsubstituted C ₁ to C ₂₀ alkyl groups, substituted or unsubstituted C ₆ to C ₆₀ aryl groups, or C ₂ to C ₆₀ heteroaryl groups. Or an unsubstituted amine group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

Substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ cycloalkyl group, A substituted or unsubstituted C ₆ to C ₆₀ aryl group or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

and t is an integer of 0 to 7.

In one embodiment of the present application, R10 to R15 in Formula 4 may each independently be hydrogen or deuterium.

According to one embodiment of the present application, the compound represented by Formula 4 may be represented by any one of the following compounds, but is not limited thereto.

In one embodiment of the present application, any one of X1 to X3 in Chemical Formula 5 may be N, any two of X1 to X3 may be N, and all of X1 to X3 may be N. [

In one embodiment of the present application, R 17 and R 18 in Formula 5 are each independently a substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group.

In one embodiment of the present application, R19 to R21 in Formula 5 may each independently be hydrogen or deuterium.

In one embodiment of the present application, any one of R22 to R26 in Formula 5 may be -CN, and the remainder may be independently hydrogen or deuterium.

According to one embodiment of the present application, the compound represented by Formula 5 may be represented by any one of the following compounds, but is not limited thereto.

The organic light emitting device according to one embodiment of the present application includes a heterocyclic compound represented by any one of formulas 1 to 3 described above; And a compound represented by the general formula (4) or (5) as a host material in the light emitting layer. At this time, the dopant material of the light emitting layer may be a material known in the art.

The heterocyclic compound represented by any one of formulas 1 to 3 in the host material may be 1:10 to 10: 1, preferably 1: 8 to 8: 1, of the compound represented by formula 4 or 5, 1: 5 to 5: 1, 1: 2 to 2: 1, and 1: 1, but is not limited thereto.

The host material may be a mixture in which two or more compounds are simply mixed. The powder material may be mixed before the organic material layer of the organic light emitting device is formed, or the compound in a liquid state at an appropriate temperature or higher may be mixed. The host material is in a solid state below the melting point of each material and can be maintained in a liquid state by adjusting the temperature.

The organic light emitting device according to one embodiment of the present application includes a heterocyclic compound represented by any one of formulas (1) to (3) described above; And the compound represented by the general formula (4) or (5) is used to form one or more organic layer (s).

The heterocyclic compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The compounds represented by the above general formulas (1) to (3) can be used as an electron transport layer, a hole blocking layer and a material for a light emitting layer in an organic light emitting device. For example, the compounds represented by Chemical Formulas 1 to 3 may be used as an electron transport layer, a hole transport layer, or a material for a light emitting layer of an organic light emitting device.

In addition, the compounds represented by the above general formulas (1) to (3) can be used as a material of a light emitting layer in an organic light emitting device. As an example, the compounds represented by the above general formulas (1) to (3) can be used as a material of the phosphorescent host of the light emitting layer in the organic light emitting device.

In addition, the organic material layer containing the compound represented by any one of formulas (1) to (3) may further include other materials as needed.

The compounds represented by the above formulas (1) to (3) can be used as the material of the charge generation layer in the organic light emitting device.

The compounds represented by the above general formulas (1) to (3) can be used as an electron transport layer, a hole blocking layer and a material for a light emitting layer in an organic light emitting device. For example, the compounds represented by Chemical Formulas 1 to 3 may be used as an electron transport layer, a hole transport layer, or a material for a light emitting layer of an organic light emitting device.

In addition, the compounds represented by the above general formulas (1) to (3) can be used as a material of a light emitting layer in an organic light emitting device. As an example, the compound represented by Formula 1 may be used as a material of a phosphorescent host of a light emitting layer in an organic light emitting device.

FIGS. 1 to 3 illustrate the stacking process of the electrode and the organic layer of the organic light emitting diode according to one embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and the structure of the organic light emitting device known in the art can be applied to the present application.

1, an organic light emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown. However, the present invention is not limited to such a structure, and an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented as shown in FIG.

FIG. 3 illustrates the case where the organic material layer is a multilayer. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except the light emitting layer may be omitted, and other necessary functional layers may be further added.

In the organic light emitting device according to one embodiment of the present application, materials other than the compounds of the above Chemical Formulas 1 to 5 are illustrated below, but these are for illustrative purposes only and are not intended to limit the scope of the present application, , ≪ / RTI >

As the cathode material, materials having a relatively large work function can be used, and a transparent conductive oxide, a metal, or a conductive polymer can be used. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline.

As the cathode material, materials having relatively low work functions can be used, and metals, metal oxides, conductive polymers, and the like can be used. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, a known hole injecting material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a compound described in Advanced Material, 6, p. 677 (1994) Star burst type amine derivatives such as tris (4-carbamoyl-9-phenyl) amine (TCTA), 4,4 ', 4 "-tri [phenyl (m- tolyl) amino] triphenylamine MTDAPA), polyaniline / dodecylbenzenesulfonic acid (poly (vinylidene fluoride)) or poly (vinylidene fluoride), which is a soluble conductive polymer, such as 1,3,5-tris [4- (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate), polyaniline / camphor sulfonic acid or polyaniline / Poly (4-styrene-sulfonate) and the like can be used.

As the hole transporting material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or a high molecular weight material may be used.

Examples of the electron transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, Derivatives thereof, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used as well as low molecular weight materials and high molecular weight materials.

As the electron injecting material, for example, LiF is typically used in the art, but the present application is not limited thereto.

The organic light emitting device according to one embodiment of the present application may be a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

The heterocyclic compound according to one embodiment of the present application may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.

Hereinafter, the present invention will be described in more detail by way of examples, but these are for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

< Example >

[ Synthetic example  1] Preparation of compound H

Preparation of Compound H

After adding 30 g (121.41 mmol) of 2-bromodibenzofuran and 300 ml of tetrahydrofuran, the solution was cooled to -78 ° C., and 88 ml of 1.8 M LDA solution was slowly added dropwise. -78 ℃ 1 hour after maintenance, was added solid iodine (I ₂₎ 33.9g (133.55mmol) and stirred for 4 hours at room temperature. Extraction was carried out using distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel and prolysyl, and the solvent was removed, followed by filtration with methanol to obtain 23.1 g (51%) of the desired compound H.

[ Manufacturing example  1-1] Preparation of Compound 1-1

Preparation of Compound 1-1-1

Compound H 20g (53.62mmol), (9- phenyl -9H-carbazol-2-yl) Boro Nick Acid 15.4g (53.62mmol), Pd (PPh 3) 4 3.1g (2.68mmol), K 2 CO 3 14.82g (107.24 mmol), 1,4-dioxane (300 ml) and water (60 ml), and the mixture was reacted at 120 ° C for 12 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, the solvent was removed, and 7.5 g (40%) of the desired compound 1-1-1 was obtained by column chromatography.

Preparation of Compound 1-1

Compound 1-1-1 5g (10.24mmol), (9- phenyl -9H-carbazol-2-yl) Boro Nick Acid 5.88g (20.48mmol), Pd (PPh 3) 4 0.59g (0.51mmol), K 2 4.25 g (30.72 mmol) of CO ₃ and 3.1 g (20.48 mmol) of CsF were added to toluene / EtOH / H ₂ O 60/10/10 ml and reacted at 100 ° C for 12 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, the solvent was removed, and 4.1 g (65%) of the desired compound 1-1 was obtained by column chromatography.

Except that the intermediate of the following Table 1 was used instead of (9-phenyl-9H-carbazol-2-yl) boronic acid in the preparation of the compound 1-1-1 in Production Example 1-1. , To thereby synthesize the desired compound A.

[Table 1]

[ Manufacturing example  2-1] Production of Compound 2-1

Preparation of Compound 2-1-1

Compound H 30g (61.40mmol), (9- phenyl -9H-carbazol-3-yl) Boro Nick Acid 17.63g (61.40mmol), Pd (PPh 3) 4 3.1g (3.55mmol), K 2 CO 3 25.46g (184.2 mmol), 300 ml of 1,4-dioxane and 60 ml of water, and the mixture was reacted at 120 DEG C for 12 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed. 17.9 g (60%) of the desired compound 2-1-1 was obtained by column chromatography.

Preparation of Compound 2-1

Compound 2-1-1 7g (14.33mmol), (9- phenyl -9H-carbazol-2-yl) Boro Nick Acid 8.23g (28.66mmol), Pd (PPh 3) 4 0.83g (0.72mmol), K 2 5.94 g (42.99 mmol) of CO ₃ and 3.1 g (20.48 mmol) of CsF were placed in toluene / EtOH / H ₂ O 80/16/16 ml and reacted at 100 ° C for 12 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, the solvent was removed, and 6.5 g (70%) of the desired compound 2-1 was obtained by column chromatography.

In the same manner as in the preparation of the compound 2-1 except that the intermediate A in the following Table 2 was used instead of the (9-phenyl-9H carbazol-3-yl) boronic acid in the preparation of the compound 2-1-1 in Production Example 2-1 Phenyl-9H-carbazol-2-yl) boronic acid was used in place of Intermediate B in Table 2, the desired compound A was synthesized.

[Table 2]

[ Manufacturing example  3-1] Preparation of Compound 3-1

Preparation of compound 3-1-1

Compound H 20g (53.62mmol), (9- phenyl -9H-carbazol-2-yl) Boro Nick Acid 15.4g (53.62mmol), Pd (PPh 3) 4 3.1g (2.68mmol), K 2 CO 3 14.82g (107.24 mmol), 1,4-dioxane (300 ml) and water (60 ml), and the mixture was reacted at 120 ° C for 12 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, the solvent was removed, and 7.5 g (40%) of the target compound 3-1-1 was obtained by column chromatography.

Preparation of Compound 3-1

Compound 3-1-1 8g (16.38mmol), (9- phenyl -9H-carbazol-3-yl) Boro Nick Acid 9.4g (32.76mmol), Pd (PPh 3) 4 0.94g (0.82mmol), K 2 6.79 g (49.14 mmol) of CO ₃ and 4.9 g (32.76 mmol) of CsF were placed in toluene / EtOH / H ₂ O 60/10/10 ml and reacted at 100 ° C for 12 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed. 6.9 g (65%) of the desired compound 3-1 was obtained by column chromatography.

In the same manner as in the preparation of the compound 3-1 except that the intermediate A in the following Table 3 was used instead of the (9-phenyl-9H carbazol-2-yl) boronic acid in the preparation of the compound 3-1-1 in Production Example 3-1 Phenyl-9H-carbazol-3-yl) boronic acid was used in place of Intermediate B in the following Table 2, the target compound A was synthesized.

[Table 3]

[ Manufacturing example  4-1] Production of compound 4-11

Preparation of compound 4-11-2

(19.0 mmol) of 2-bromodibenzo [b, d] thiophene, 2.6 g (15.8 mmol) of 9H-carbazole, 3.0 g (15.8 mmol) of CuI, 1.9 mL of trans-1,2-diaminocyclohexane (15.8 mmmol) of K ₃ PO _{4 and} 3.3 g (31.6 mmol) of K ₃ PO ₄ were dissolved in 100 ml of 1,4-oxalic acid and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 4.7 g (85%) of the desired compound 4-11-2.

Preparation of compound 4-11-1

To a mixed solution of 5 g (14.3 mmol) of the compound 4-11-2 and 100 mL of THF was added dropwise 7.4 mL (18.6 mmol) of 2.5M n-BuLi at -78 ° C and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 4.8 mL (42.9 mmol) of trimethyl borate (B (OMe) ₃ ) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: MeOH = 100: 3) and recrystallized with DCM to obtain 3.9 g (70%) of the desired compound 4-11-1.

Preparation of compounds 4-11

Compound 4-11-1 7.5g (19.0mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 5.1g (19.0mmol), Pd (PPh 3) 4 1.1g (0.95mmol ) And 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 7.7 g (70%) of the desired compound 4-11.

[ Manufacturing example  4-2] Preparation of compound 4-12

6.5 g (19.0 mmol) of 4-11-1 and 6.5 g (19.0 mmol) of 2 - ([1,1'-biphenyl] 1.1 g (0.95 mmol) of Pd (PPh ₃ ) ₄ and 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain the desired compound 4-12 8.7 g (70%) was obtained.

[ Manufacturing example  4-3] Preparation of compound 4-28

Compound 4-11-1 7.5g (19.0mmol), 2- ( 3- bromophenyl) -4,6-diphenyl-1,3,5-triazine 7.4g (19.0mmol), Pd (PPh 3) _{4 1.1g (0.95mmol), K 2} CO 3 5.2g were dissolved (38.0mmol) in toluene _{/ EtOH / H 2 O 100/} 20 / 20mL mixture was refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain the desired compound 4-28 8.7 g (70%) was obtained.

[ Manufacturing example  4-4] Preparation of compound 4-36

Compound 4-11-1 7.5g (19.0mmol), 2- ( 4- bromophenyl) -4,6-diphenyl-1,3,5-triazine 7.4g (19.0mmol), Pd (PPh 3) ₄ 1.1g (0.95mmol) and K ₂ CO ₃ 5.2g after (38.0mmol) dissolved in toluene _{/ EtOH / H 2 O 100/} 20 / 20mL mixture was refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain the desired compound 4-36 8.7 g (70%) was obtained.

[ Manufacturing example  4-5] Preparation of compound 4-39

Preparation of compound 4-39-2

(19.0 mmol) of 2-bromodibenzo [b, d] thiophene, 3.8 g (15.8 mmol) of 2-phenyl-9H- carbazole, 3.0 g (15.8 mmol) of CuI, 1.9 mL (15.8 mmol) of cyclohexane and 3.3 g (31.6 mmol) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-oxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 5.7 g (85%) of the desired compound 4-39-2.

Preparation of compound 4-39-1

To a mixed solution of 6.1 g (14.3 mmol) of the compound 4-39-2 and 100 mL of THF was added dropwise 7.4 mL (18.6 mmol) of 2.5M n-BuLi at -78 ° C and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 4.8 mL (42.9 mmol) of trimethyl borate (B (OMe) ₃ ) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: MeOH = 100: 3) and recrystallized with DCM to obtain 4.7 g (70%) of the desired compound 4-39-1.

Preparation of compound 4-39

Compound 4-39-1 8.9g (19.0mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 5.1g (19.0mmol), Pd (PPh 3) 4 1.1g (0.95mmol ) And 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 8.7 g (70%) of the desired compound 4-39.

[ Manufacturing example  4-6] Preparation of compound 4-40

8.9 g (19.0 mmol) of the compound 4-39-1 and 7.4 g (20 mmol) of 2 - ([1,1'-biphenyl] -3- 1.1 g (0.95 mmol) of Pd (PPh ₃ ) ₄ and 5.2 g (38.0 mM) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.7 g (70%) of the target compound 4-40.

[ Manufacturing example  4-7] Preparation of compound 4-41

8.9 g (19.0 mmol) of the compound 4-39-1 and 7.4 g (20 mmol) of 2 - ([1,1'-biphenyl] -4- 1.1 g (0.95 mM) of Pd (PPh ₃ ) _{4 and} 5.2 g (38.0 mM) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9 g (65%) of the desired compound 4-41.

[ Manufacturing example  4-8] Preparation of compound 4-42

Compound 4-39-1 8.9g (19.0mmol), 2- ( 3- bromophenyl) -4,6-diphenyl-1,3,5-triazine 7.4g (19.0mmol), Pd (PPh 3) ₄ 1.1g (0.95mmol) and K ₂ CO ₃ 5.2g after (38.0mmol) dissolved in toluene / EtOH / H ₂ O 100/20/20 mL was refluxed 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.7 g (70%) of the desired compound 4-42.

[ Manufacturing example  4-9] Preparation of compound 4-43

Compound 4-39-1 8.9g (19.0mmol), 2- ( 4- bromophenyl) -4,6-diphenyl-1,3,5-triazine 7.4g (19.0mmol), Pd (PPh 3) _{4 1.1g (0.95mmol), K 2} CO 3 5.2g were dissolved (38.0mmol) in toluene _{/ EtOH / H 2 O 100/} 20 / 20mL mixture was refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.7 g (70%) of the target compound 4-43.

[ Manufacturing example  4-10] Preparation of compound 4-47

Preparation of compound 4-47-2

5.0 g (19.0 mmol) of 2-bromodibenzo [b, d] thiophene, 5.0 g (15.8 mmol) of 2,7-diphenyl-9H- carbazole, 3.0 g (15.8 mmol) (15.8 mmol) of diaminocyclohexane and 3.3 g (31.6 mmol) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-oxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 6.7 g (85%) of the desired compound 4-47-2.

Preparation of compound 4-47-1

7.2 mL (14.3 mmol) of the compound 4-47-2 and 100 mL of THF was added dropwise at -78 째 C to 7.4 mL (18.6 mmol) of 2.5M n-BuLi, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 4.8 mL (42.9 mmol) of trimethyl borate (B (OMe) ₃ ) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: MeOH = 100: 3) and recrystallized with DCM to obtain the desired compound 4-47-1 (60%).

Preparation of compound 4-47

4-47-1 compound 10.4g (19.0mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 5.1g (19.0mM), Pd (PPh 3) 4 1.1g (0.95mmol ) And 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.7 g (70%) of the desired compound 4-47.

[ Manufacturing example  4-11] Preparation of compound 4-66

Preparation of compound 4-66-2

5.0 g (19.0 mmol) of 2-bromodibenzo [b, d] thiophene, 4.5 g (15.8 mmol) of 7,7-dimethyl-5,7-dihydroindeno [2,1- 1.9 mL (15.8 mmol) of trans-1,2-diaminocyclohexane and 3.3 g (31.6 mmol) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-oxalic acid and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 7.3 g (85%) of the target compound 4-66-2.

Preparation of compound 4-66-1

To a mixed solution of 6.7 g (14.3 mmol) of the compound 4-66-2 and 100 mL of THF was added dropwise 7.4 mL (18.6 mmol) of 2.5M n-BuLi at -78 ° C and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 4.8 mL (42.9 mmol) of trimethyl borate (B (OMe) ₃ ) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: MeOH = 100: 3) and recrystallized with DCM to obtain 5.1 g (70%) of the target compound 4-66-1.

Preparation of compound 4-66

Compound 4-66-1 9.7g (19.0mmol), 2- bromo-4, 6-diphenyl-pyrimidine 5.9g (19.0mmol), Pd (PPh 3) 4 1.1g (0.95mmol), K 2 CO 3 5.2 g (38.0 mmol) was dissolved in toluene / EtOH / H ₂ O 100/20 / mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.3 g (70%) of the desired compound 4-66.

[ Manufacturing example  4-12] Preparation of compound 4-68

Compound 4-66-1 9.7g (19.0mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 5.1g (19.0mmol), Pd (PPh 3) 4 1.1g (0.95mmol ) And 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.3 g (70%) of the target compound 4-68.

[ Manufacturing example  4-13] Preparation of compound 4-71

Compound 4-66-1 9.7g (19.0mmol), 2- ( 3- bromophenyl) -4,6-diphenyl-1,3,5-triazine 7.4g (19.0mmol), Pd (PPh 3) _{4 1.1g (0.95mmol), K 2} CO 3 5.2g were dissolved (38.0mmol) in toluene _{/ EtOH / H 2 O 100/} 20 / 20mL mixture was refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 10.3 g (70%) of the desired compound 4-71.

[ Manufacturing example  4-14] Preparation of compound 4-74

Compound 4-66-1 9.7g (19.0mmol), 2- ( 4- bromophenyl) -4,6-diphenyl-1,3,5-triazine 7.4g (19.0mmol), Pd (PPh 3) _{4 1.1g (0.95mmol), K 2} CO 3 5.2g were dissolved (38.0mmol) in toluene _{/ EtOH / H 2 O 100/} 20 / 20mL mixture was refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 10.3 g (70%) of the target compound 4-74.

[ Manufacturing example  4-15] Preparation of compound 4-79

Preparation of compound 4-79-2

4.5 g (15.8 mmol) of 11,11-dimethyl-5,11-dihydroindeno [l, 2-b] carbazole, 5.0 g (19.0 mmol) of 2-bromodibenzo [b, 1.9 mL (15.8 mmol) of trans-1,2-diaminocyclohexane and 3.3 g (31.6 mmol) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-oxalic acid and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 5.9 g (80%) of the desired compound 4-79-2.

Preparation of compound 4-79-1

To a mixed solution of 6.7 g (14.3 mmol) of the compound 4-79-2 and 100 mL of THF was added dropwise 7.4 mL (18.6 mmol) of 2.5M n-BuLi at -78 ° C and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 4.8 mL (42.9 mmol) of trimethyl borate (B (OMe) ₃ ) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: MeOH = 100: 3) and recrystallized with DCM to obtain 5.1 g (70%) of the desired compound 4-79-1.

Preparation of compound 4-79

Compound 4-79-1 9.7g (19.0mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 5.1g (19.0mmol), Pd (PPh 3) 4 1.1g (0.95mmol ) And 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.3 g (70%) of the desired compound 4-79.

[ Manufacturing example  4-16] Preparation of compound 4-83

Preparation of compound 4-83-2

5.0 g (19.0 mmol) of 2-bromodibenzo [b, d] thiophene, 5.3 g (15.8 mmol) of 5-phenyl-5,7-dihydroindolo [2,3- 1.9 mL (15.8 mmol) of trans-1,2-diaminocyclohexane and 3.3 g (31.6 mmol) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-dioxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 6.9 g (85%) of the target compound 4-83-2.

Preparation of compound 4-83-1

7.4 ml (14.3 mmol) of the compound 4-83-2 and 100 ml of THF were added dropwise at -78 째 C to 7.4 ml (18.6 mmol) of 2.5M n-BuLi, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 4.8 mL (42.9 mmol) of trimethyl borate (B (OMe) ₃ ) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: MeOH = 100: 3) and recrystallized with DCM to obtain 5.63 g (70%) of the desired compound 4-83-1.

Preparation of compound 4-83

4-83-1 compound 10.6g (19.0mmol), 2- bromo-4, 6-diphenyl-pyrimidine 5.9g (19.0mmol), Pd (PPh 3) 4 1.1g (0.95mmol), K 2 CO 3 5.2 g (38.0 mmol) was dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.3 g (70%) of the desired compound 4-83.

[ Manufacturing example  4-17] Preparation of compound 4-85

4-83-1 compound 10.6g (19.0mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 5.1g (19.0mM), Pd (PPh 3) 4 1.1g (0.95mmol ) And 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.3 g (70%) of the target compound 4-85.

[ Manufacturing example  4-18] Preparation of compound 4-99

Preparation of compound 4-99-2

Benzo [4,5] thieno [3,2-c] carbazole, 3.0 g (15.8 mmol) of CuI, 5.0 g (19.0 mmol) of 2-bromodibenzo [b, 1.9 mL (15.8 mmol) of trans-1,2-diaminocyclohexane and 3.3 g (31.6 mmol) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-dioxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 7.2 g (85%) of the target compound 4-99-2.

Preparation of compound 4-99-1

6.5 mL (14.3 mmol) of the compound 4-99-2 and 100 mL of THF was added dropwise at -78 째 C to 7.4 mL (18.6 mmol) of 2.5 M n-BuLi and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 4.8 mL (42.9 mmol) of trimethyl borate (B (OMe) ₃ ) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: MeOH = 100: 3) and recrystallized with DCM to obtain 5.0 g (70%) of the target compound 4-99-1.

Preparation of Compound 4-99

Compound 4-99-1 9.5g (19.0mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 5.1g (19.0mmol), Pd (PPh 3) 4 1.1g (0.95mmol ) And 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 8.9 g (70%) of the desired compound 4-99.

[ Manufacturing example  4-19] Preparation of compound 4-164

Preparation of compound 4-164-2

2-Bromo-modify-benzo [b, d] thiophene 5g (19.0mmol), (4- ( 9H- carbazol-9-yl) phenyl) boronic acid 5.5g (19.0mmol), Pd (PPh 3) 4 1.1g (0.95 mmol) of K ₂ CO _{3 and} 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 8.9 g (70%) of the target compound 4-164-2.

Preparation of compound 4-164-1

To a mixed solution of 6.09 g (14.3 mmol) of the compound 4-164-2 and 100 mL of THF was added dropwise 7.4 mL (18.6 mmol) of 2.5M n-BuLi at -78 ° C and the mixture was stirred at room temperature for 1 hour. To the reaction mixture, 4.8 mL (42.9 mmol) of trimethyl borate (B (OMe) ₃ ) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: MeOH = 100: 3) and recrystallized with DCM to obtain 4.7 g (70%) of the target compound 4-164-1.

Preparation of compound 4-164

Compound 4-164-1 8.9g (19.0mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 6.1g (22.8mmol), Pd (PPh 3) 4 1.1g (0.95mmol ) And 5.2 g (38.0 mmol) of K ₂ CO ₃ were dissolved in toluene / EtOH / H ₂ O 100/20 / 20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain 9.0 g (72%) of the target compound 4-164.

 [ Manufacturing example  5-1] Production of compound 5-87

Preparation of compound 5-87-3

(52.93 mmol) of compound 9H-carbazole, 22.1 g (105.8 mmol) of 1-bromo-3-chloro-5-fluorobenzene, 1.9 g (79.40 mmol) of sodium hydride and 200 mL of DMF, And reacted for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel and prolysyl, and the solvent was removed to obtain 13.2 g (70%) of the desired compound 5-87-3.

Preparation of compound 5-87-2

13.26 g (52.24 mmol) of bis (pinacolato) diboron, 0.8 g (1.205 mmol) of PdCl ₂ (dppf), 11.8 g (120.5 mmol) of KOAc, 150 mL of 4-dioxane was added, and the mixture was reacted at 120 DEG C for 5 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed to obtain 12.7 g (78%) of the desired compound 5-87-2.

Preparation of compound 5-87-1

Compound 5-87-2 14g (34.6mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 11.2g (41.5mmol), Pd (PPh 3) 4 2g (1.7mmol), 14.3 g (103.8 mmol) of K ₂ CO ₃ , 120 mL of toluene, 20 mL of ethanol and 20 mL of water were placed and reacted at 120 ° C. for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. Then, it was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and recrystallized from dichloromethane and methanol to obtain the desired compound 5-87-1 14.1 g (80%) was obtained.

Preparation of compound 5-87

2.1 g (14.37 mmol) of Pd ₂ (dba) ₃ and 6.1 g (0.67 mmol) of K ₃ PO _{4 were} added to a solution of 4.9 g (9.582 mmol) of compound 5-87-1, 0.91 g (1.91 mmol) of Xphos, 60 mL of toluene and 10 mL of water, and the atmosphere was replaced with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator, and dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain the desired compound 5-87 4.0 g (73%) of the title compound was obtained.

[ Manufacturing example  5-2] Preparation of Compound 5-99

Preparation of compound 5-99-1

Compound 5-203-2 18g (34.6mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 11.2g (41.5mmol), Pd (PPh 3) 4 2g (1.7mmol), 14.3 g (103.8 mmol) of K ₂ CO ₃ , 120 mL of toluene, 20 mL of ethanol and 20 mL of water were placed and reacted at 120 ° C. for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and recrystallized from dichloromethane and methanol to obtain 16 g (77%) of the desired compound 5-99-1.

Preparation of Compound 5-99

Compound 5-99-1 6g (9.58mmol), (between 2-cyano-phenyl) Boro Nick Acid _{2.1g (14.37mmol), Pd 2 (} dba) 3 0.61g (67mmol), K 3 PO 4 6.1g (28.7mmol ), Xphos (0.91 g, 1.91 mmol), toluene (60 mL) and water (10 mL) were purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 4.1 g (73%) of the target compound 5-99.

[ Manufacturing example  5-3] Preparation of Compound 5-203

Preparation of compound 5-203-3

(52.93 mmol) of 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole and 22.1 g (105.8 mmol) of 1-bromo-3- , 1.9 g (79.4 mmol) of sodium hydride, and 200 mL of DMF were placed and reacted at 120 DEG C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel and prolysyl, and the solvent was removed to obtain 19 g (76%) of the desired compound 5-203-3.

Preparation of compound 5-203-2

(40.18 mmol) of the compound 5-203-3, 13.26 g (52.24 mmol) of bis (pinacolato) diboron, 0.8 g (1.21 mmol) of PdCl ₂ (dppf), 11.8 g (120.5 mmol) - dioxane (150 mL), and the mixture was reacted at 120 ° C for 5 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed to obtain 18 g (76%) of the desired compound 5-203-2.

Preparation of compound 5-203-1

Compound 5-203-2 18g (34.6mmol), 2- chloro-4,6-diphenyl-pyrimidine 11.0g (41.5mmol), Pd (PPh 3) 4 2g (1.7mmol) and K ₂ CO ₃ 14.3g ( 120 mL of toluene, 20 mL of ethanol and 20 mL of water were placed and reacted at 120 ° C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and recrystallized from dichloromethane and methanol to obtain 15 g (78%) of the desired compound 5-203-1.

Preparation of Compound 5-203

Compound 5-203-1 5g (7.98mmol), (3-cyano-phenyl between) Boro Nick Acid _{1.5g (10.38mmol), Pd 2 (} dba) 3 0.36g (39mmol), K 3 PO 4 5.2g (23.9mmol ), Sphos (0.33 g, 79 mmol), toluene (60 mL) and water (10 mL) were purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The solvent was removed by column chromatography using dichloromethane and hexane 1: 1 to obtain 3.4 g (61%) of the target compound 5-203.

[ Manufacturing example  5-4] Preparation of compound 5-260

Compound 5-99-1 5g (7.98mmol), (3-cyano-phenyl between) Boro Nick Acid _{1.5g (10.38mmol), Pd 2 (} dba) 3 0.36g (39mmol), K 3 PO 4 5.2g (23.9mmol ), Sphos (0.33 g, 79 mmol), toluene (60 mL) and water (10 mL) were purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 3.5 g (64%) of the target compound 5-260.

[ Manufacturing example  5-5] Preparation of compound 5-262

Preparation of Compound 5-262-3

(53 mmol) of the compound 11,11-dimethyl-5,11-dihydroindeno [1,2-b] carbazole, 24.3 g (106.01 mmol) of 1-bromo-3- 3.1 g (79.54 mmol) of sodium hydride and 200 mL of DMF were placed and reacted at 120 DEG C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel and prolysyl, and the solvent was removed to obtain 17 g (71%) of the target compound 5-262-3.

Preparation of compound 5-262-2

17.0 g (40.25 mmol) of the compound 5-262-3, 15.2 g (60.81 mmol) of bis (pinacolato) diboron, 1.4 g (2.01 mmol) of PdCl ₂ (dppf) and 11.8 g - dioxane (150 mL), and the mixture was reacted at 120 ° C for 5 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed to obtain 16 g (72%) of the target compound 5-262-2.

Preparation of compound 5-262-1

Compound 5-262-2 16g (34.68mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 19.4g (52.02mmol), Pd (PPh 3) 4 2.6g (1.7mmol) 14.3 g (109.8 mmol) of K ₂ CO ₃ , 120 mL of toluene, 20 mL of ethanol and 20 mL of water were placed and reacted at 120 ° C. for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and recrystallized from dichloromethane and methanol to obtain 16 g (75%) of the desired compound 5-262-1.

Preparation of compound 5-262

Compound 5-262-1 6g (9.64mmol), (3-cyano-phenyl between) Boro Nick Acid _{2.1g (14.42mmol), Pd 2 (} dba) 3 0.44g (48mmol), K 3 PO 4 6.1g (28.9mmol ), Sphos (0.39 g, 94 mmol), toluene (60 mL) and water (10 mL) were purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 4.6 g (77%) of the target compound 5-262.

 [ Manufacturing example  5-6] Preparation of Compound 5-264

Preparation of compound 5-264-3

(53 mmol) of the compound 11,11-dimethyl-5,11-dihydroindeno [1,2-b] carbazole, 24.3 g (106.01 mmol) of 1-bromo-3- 3.1 g (79.54 mmol) of sodium hydride and 200 mL of DMF were placed and reacted at 120 DEG C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel and prolysyl, and the solvent was removed to obtain 19 g (78%) of the target compound 5-264-3.

Preparation of compound 5-264-2

(40.15 mmol) of compound 5-264-3, 15.2 g (60.81 mmol) of bis (pinacolato) diboron, 1.4 g (2.01 mmol) of PdCl ₂ (dppf), 11.8 g - dioxane (150 mL), and the mixture was reacted at 120 ° C for 5 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed to obtain 18 g (73%) of the target compound 5-264-2.

Preparation of compound 5-264-1

Compound 5-264-2 18g (34.68mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 19.4g (52.02mmol), Pd (PPh 3) 4 2.6g (1.7mmol) 14.3 g (109.8 mmol) of K ₂ CO ₃ , 120 mL of toluene, 20 mL of ethanol and 20 mL of water were placed and reacted at 120 ° C. for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and recrystallized from dichloromethane and methanol to obtain the desired compound 5-264-1 (16 g, 74%).

Preparation of compound 5-264

Compound 5-264-1 6g (9.64mmol), (3-cyano-phenyl between) Boro Nick Acid _{2.1g (14.42mmol), Pd 2 (} dba) 3 0.44g (48mmol), K 3 PO 4 6.1g (28.9mmol ), Sphos (0.39 g, 94 mmol), toluene (60 mL) and water (10 mL) were purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ and the solvent was removed using a rotary evaporator. The dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 4.6 g (75%) of the target compound 5-264.

[ Manufacturing example  5-7] Preparation of compound 5-267

Preparation of compound 5-267-3

Bromo-3-chloro-5-fluorobenzene (22.9 g, 109.89 mmol) and sodium hydride (82.41 mmol) of DMF, and 200 mL of DMF, and the mixture was reacted at 120 DEG C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel and prolysyl, and the solvent was removed to obtain 17 g (76%) of the desired compound 5-267-3.

Preparation of compound 5-267-2

17.6 g (41.12 mmol) of the compound 5-267-3, 15.6 g (61.68 mmol) of bis (pinacolato) diboron, 1.5 g (2.056 mmol) of PdCl ₂ (dppf), 12.08 g (123.3 mmol) - dioxane (150 mL), and the mixture was reacted at 120 ° C for 5 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed to obtain 19 g (76%) of the desired compound 5-267-2.

Preparation of Compound 5-267-1

Compound 5-267-2 17.7g (34.68mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 19.4g (52.02mmol), Pd (PPh 3) 4 2.6g (1.7mmol ), 14.3 g (109.8 mmol) of K ₂ CO ₃ , 120 mL of toluene, 20 mL of ethanol and 20 mL of water were placed and reacted at 120 ° C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and recrystallized from dichloromethane and methanol to obtain 15.8 g (74%) of the desired compound 5-267-1.

Preparation of Compound 5-267

Compound 5-267-1 5.9g (9.64mmol), (3-cyano-phenyl between) Boro Nick Acid _{2.1g (14.42mmol), Pd 2 (} dba) 3 0.44g (48mmol), K 3 PO 4 6.1g (28.9 mmol), Sphos (0.39 g, 94 mmol), toluene (60 mL) and water (10 mL) were purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Then, dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 4.9 g (75%) of the target compound 5-267.

[ Manufacturing example  5-8] Preparation of compound 5-271

Preparation of compound 5-271-3

(58.36 mmol) of compound 5H-benzofuro [3,2-c] carbazole, 24.3 g (116.73 mmol) of 1-bromo-3-chloro-5-fluorobenzene, 3.5 g ), 200 mL of DMF was added, and the mixture was reacted at 120 DEG C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel and prolysyl, and the solvent was removed to obtain 18 g (73%) of the target compound 5-271-3.

Preparation of compound 5-271-2

18.6 g (42.6 mmol) of the compound 5-271-2, 15.6 g (63.90 mmol) of bis (pinacolato) diboron, 1.5 g (2.130 mmol) of PdCl ₂ - dioxane (150 mL), and the mixture was reacted at 120 ° C for 5 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed to obtain 17 g (78%) of the target compound 5-271-2.

Preparation of compound 5-271-1

Compound 5-271-2 17g (36.51mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 19.4g (73.02mmol), Pd (PPh 3) 4 2.6g (1.7mmol) , 14.3 g (106.0 mmol) of K ₂ CO ₃ , 120 mL of toluene, 20 mL of ethanol and 20 mL of water were placed and reacted at 120 ° C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and recrystallized from dichloromethane and methanol to obtain 18 g (71%) of the target compound 5-271-1.

Preparation of Compound 5-271

Compound 5-271-1 6g (8.34mmol), (3- cyanophenyl) Boro Nick Acid _{1.8g (12.52mmol), Pd 2 (} dba) 3 0.38g (0.41mmol), K 3 PO 4 5.3g (25.1 mmol), Sphos (0.34 g, 0.83 mmol), toluene (60 mL) and water (10 mL). The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 4.6 g (72%) of the target compound 5-271.

[ Manufacturing example  5-9] Preparation of compound 5-416

Compound 5-99-1 5g (7.98mmol), (4-cyano-phenyl between) Boro Nick Acid _{1.5g (10.38mmol), Pd 2 (} dba) 3 0.36g (39mmol), K 3 PO 4 5.2g (23.9mmol ), Sphos (0.33 g, 79 mmol), toluene (60 mL) and water (10 mL) were purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 4.1 g (73%) of the target compound 5-416.

[ Manufacturing example  5-10] Production of compound 5-421

Preparation of compound 5-421-3

Bromo-3-chloro-5-fluorobenzene 22.9 g (109.89 mmol) and sodium hydride (82.41 mmol) of DMF, and 200 mL of DMF, and the mixture was reacted at 120 DEG C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel and prolysyl, and the solvent was removed to obtain 17 g (76%) of the desired compound 5-421-3.

Preparation of compound 5-421-2

17.6 g (41.12 mmol) of the compound 5-421-3, 15.6 g (61.68 mmol) of bis (pinacolato) diboron, 1.5 g (2.056 mmol) of PdCl ₂ (dppf), 12.08 g (123.3 mmol) - dioxane (150 mL), and the mixture was reacted at 120 ° C for 5 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed to obtain 19 g (76%) of the desired compound 5-421-2.

Preparation of compound 5-421-1

Compound 5-421-2 19g (35.36mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 14.1g (53.04mmol), Pd (PPh 3) 4 2g (1.7mmol), 14.3 g (106.0 mmol) of K ₂ CO ₃ , 120 mL of toluene, 20 mL of ethanol and 20 mL of water were placed and reacted at 120 ° C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and recrystallized from dichloromethane and methanol to obtain 15 g (77%) of the desired compound 5-421-1.

Preparation of Compound 5-421

Compound 5-421-1 5g (8.13mmol), (4- cyanophenyl) Boro Nick Acid _{1.7g (12.19m mol), Pd 2} (dba) 3 0.36g (0.40mmol), K 3 PO 4 5.8g ( And 0.33 g (0.79 mmol) of Sphos, 60 mL of toluene and 10 mL of water, and the mixture was purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 4.5 g (78%) of the target compound 5-421.

[ Manufacturing example  5-11] Preparation of compound 5-422

Preparation of compound 5-422

Compound 5-267-1 5g (8.13mmol), (4-cyano-phenyl between) Boro Nick Acid _{1.7g (12.19mmol), Pd 2 (} dba) 3 0.36g (0.40mmol), K 3 PO 4 5.8g (24.39 mmol), Sphos (0.33 g, 0.79 mmol), toluene (60 mL) and water (10 mL) were purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 4.3 g (72%) of the target compound 5-422.

[ Manufacturing example  5-12] Preparation of compound 5-450

Preparation of compound 5-450-3

(52.89 mmol) of the compound 2-phenyl-9H-carbazole, 22.1 g (105.8 mmol) of 1-bromo-3-chloro-5-fluorobenzene, 1.9 g (79.40 mmol) of sodium hydride, And the mixture was reacted at 120 ° C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel and prolysyl, and the solvent was removed to obtain 17.2 g (74%) of the desired compound 5-450-3.

Preparation of compound 5-450-2

17.0 g (40.09 mmol) of the compound 5-450-3, 13.26 g (52.24 mmol) of bis (pinacolato) diboron, 0.8 g (1.205 mmol) of PdCl ₂ (dppf), 11.8 g (120.5 mmol) 150 mL of 4-dioxane was added, and the mixture was reacted at 120 DEG C for 5 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and the solvent was removed to obtain the desired compound 5-450-2 14.8 (74%).

Preparation of compound 5-450-1

Compound 5-450-2 11.7g (24.53mmol), 2- chloro-4,6-diphenyl-1,3,5-triazine 7.9g (29.48mmol), Pd (PPh 3) 4 1.4g (1.2mmol ), 10.1 g (73.7 mmol) of K ₂ CO ₃ , 120 mL of toluene, 20 mL of ethanol and 20 mL of water were placed and reacted at 120 ° C for 8 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, and recrystallized from dichloromethane and methanol to obtain 10 g (70%) of the desired compound 5-450-1.

Preparation of compound 5-450

Compound 5-450-1 5.6g (9.582mmol), 3,5- dicyano-phenyl boronic acid pinacol ester _{3.7g (14.37mmol), Pd 2 (} dba) 3 0.61g (0.67mmol), K 3 PO 4 6.1 g, 0.91 g (1.91 mmol) of Xphos, 60 mL of toluene and 10 mL of water, and the mixture was purged with nitrogen. The reaction was refluxed for 12 hours and extracted with distilled water and dichloromethane. The organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. The dichloromethane and hexane were subjected to column purification at a ratio of 1: 1 to obtain 3.8 g (58%) of the target compound 5-450.

[compare Manufacturing example  1] Manufacture of Ref 5

Preparation of compound Ref-5-1

Compound H 30g (61.40mmol), (9- phenyl -9H-carbazol-3-yl) Boro Nick Acid 17.63g (61.40mmol), Pd (PPh 3) 4 3.1g (3.55mmol), K 2 CO 3 25.46g (184.2 mmol), 1,4-dioxane (300 ml) and water (60 ml), and the mixture was reacted at 120 ° C for 12 hours. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, the solvent was removed, and 17.9 g (60%) of the target compound Ref-5-1 was obtained by column chromatography.

Preparation of compound Ref 5

Compound Ref-5-1 6g (12.28mmol), (9- phenyl -9H-carbazol-3-yl) Boro Nick Acid 7.08g (24.57mmol), Pd (PPh 3) 4 0.71g (0.61mmol), K 2 _{CO 3 5.09g (36.84mmol) CsF 3.7g} (24.57mmol) and toluene 60ml, 10ml of ethanol, 10ml of water was put into the reaction for 12 hours at 100 ℃. After cooling to room temperature, it was extracted with distilled water and dichloromethane. The residue was dissolved in dichloromethane, filtered using silica gel, celite and prolysyl, the solvent was removed, and 1 g (63%) of Comparative Example Ref 5 was obtained by column chromatography.

The compounds were prepared in the same manner as in the above Preparation Examples, and the results of confirmation of the synthesis are shown in Tables 4 to 7 below. Table 4 shows NMR values, and Table 5 shows measured values of FD-MS (field desorption mass spectrometry).

[Table 4]

[Table 5]

[Table 6]

[Table 7]

< Experimental Example >

1) Fabrication of organic light emitting device

The glass substrate coated with ITO thin film with a thickness of 1500Å was washed with distilled water ultrasonic waves. After the distilled water was washed, it was ultrasonically cleaned with a solvent such as acetone, methanol, isopropyl alcohol, dried, and UV-treated for 5 minutes using UV in a UV scrubber. Subsequently, the substrate was transferred to a plasma cleaner (PT), subjected to a plasma treatment for removing ITO work function and residual film in a vacuum state, and transferred to a thermal evaporation apparatus for organic vapor deposition.

2-TNATA (4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine) was formed as a hole injection layer on the prepared ITO layer and NPB (N, N'-Di (1,1'-biphenyl) -4,4'-diamine) was formed on the hole transport layer. The light emitting layer was formed by thermal vacuum deposition on the hole transport layer to have a thickness of 400 ANGSTROM. Host In the following table, Ir (ppy) ₃ (tris (2-phenylpyridine) iridium) was doped with 7% as a phosphorescent dopant and then BCP was deposited as a hole blocking layer to a thickness of 60 Å. ₃ was deposited to a thickness of 200 A. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer. Then, an aluminum (Al) To form an anode, thereby fabricating an organic electroluminescent device.

On the other hand, all the organic compounds required for OLED device fabrication were vacuum sublimated and refined under 10 ^-6 ~ 10 ^-8 torr for each material, and used for OLED fabrication.

2) Organic Field  The driving voltage and luminous efficiency of the light-

Electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured with a M7000 of Mitsubishi Electric Corporation, and the reference luminance was 6,000 through a life span measuring instrument (M6000) manufactured by Mac Science Co., When cd / m ² , T ₉₀ was measured. The characteristics of the organic electroluminescent device of the present invention are shown in Tables 8 and 9 below.

[Table 8]

When the results of the evaluation of the organic light emitting device of the present invention and Comparative Examples 1 to 6 are compared, in the case of Ref 1, 2 and 3, when the carbazole-N is substituted for the dibenzofuran 2 position, the oxygen of the dibenzofuran in the para position is activated to weaken the resonance and the stability of the molecule is lowered. In the case of Ref 4, when the heteroaryl group pulling electrons is substituted at the 4-position of dibenzofuran, it is considered that the oxygen atom of the dibenzofurane group giving electrons destabilizes the electron injected along the LUMO . Ref 5 has a molecular structure similar to that of the present invention. However, when carbazole is substituted at the 3-position of dibenzofuran at position 2 and 4, the life characteristics are degraded due to the same reasons as Ref 1, .

[Table 9]

As described above, in particular, the organic light emitting device according to one embodiment of the present application is a compound represented by any one of the general formulas (1) to (3) as a host material of the light emitting layer; And the compound represented by the general formula (4) or (5) at the same time, the organic EL device of the present invention can exhibit significantly improved driving efficiency, lifetime, However, in the case of Comparative Examples 7 to 16, even when the light emitting layer is composed of two hosts, the holes and electrons are not balanced with each other, and the lifetime characteristics are particularly lower than those of the examples.

The organic light emitting device of the present invention includes a host and a light emitting layer using a phosphorescent dopant, and the host is composed of a host compound (pn type) in which two or more compounds are mixed, There is an effect that the lifetime characteristics are superior to those of the organic light emitting element.

Particularly, the pn type host of the present invention has an advantage of increasing the luminescence characteristics by controlling the ratio of the host, which is a result of a proper combination of P host having good hole mobility and n host having good electron mobility to be.

100: substrate
200: anode
300: organic layer
301: Hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (11)

A heterocyclic compound represented by any one of formulas (1) to (3)
[Chemical Formula 1]

(2)

(3)

In the above Formulas 1 to 3,
Ar 1 to Ar 6 are the same or different and are each independently substituted with a C ₁ to C ₆₀ alkyl group, a C ₆ to C ₆₀ aryl group, a C ₂ to C ₆₀ heteroaryl group, -CN or -SiRR'R " and the, or C ₁ to C ₆₀ alkyl or C ₆ to C ₆₀ aryl group substituted or unsubstituted in the C ₂ to C ₆₀ unsubstituted heteroaryl group; or unsubstituted C ₆ to C ₆₀ aryl group
R1 to R9 are hydrogen,
R, R 'and R "are the same or different and are each independently a C ₆ to C ₆₀ aryl group,
m, n, o, p, q, r, s, t and u are each independently an integer of 0 to 4; delete The heterocyclic compound according to claim 1, wherein the compounds represented by formulas (1) to (3) are represented by any one of the following compounds:

1. An organic light emitting device comprising an anode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes a heterocyclic compound according to any one of claims 1 and 3. 5. The organic electroluminescent device according to claim 4, wherein the organic material layer includes at least one of a hole blocking layer, an electron injection layer and an electron transporting layer, and at least one of the hole blocking layer, the electron injection layer and the electron transporting layer includes the heterocyclic compound Wherein the organic light-emitting device comprises: 5. The organic light emitting device according to claim 4, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the heterocyclic compound. [Claim 4] The organic electroluminescent device according to claim 4, wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, wherein one of the layers includes the heterocyclic compound . [4] The organic light emitting device of claim 4, wherein the organic compound layer containing the heterocyclic compound further comprises a compound represented by the following formula (4) or (5)
[Chemical Formula 4]

In Formula 4,
L1 and L2 are the same or different and are each independently a direct bond or a C ₆ to C ₆₀ arylene group,
Ar7 is an aryl group of -NO _2, -CN, or C ₁ to C ₆₀ alkyl group substituted or unsubstituted C ₆ to C ₆₀ ring to the; And C ₂ to be unsubstituted or substituted by one or more substituents selected from the group consisting of a heteroaryl group of C _60, and at least a heteroaryl group of C ₂ to C ₆₀ comprising one of N,
Ar8 is represented by the following formula (6) or (7)
[Chemical Formula 6]

(7)

Y1 to Y4 are the same or different and are each independently a C ₆ to C ₆₀ aryl group, a C ₂ to C ₆₀ heteroaryl group substituted or unsubstituted with a C ₆ to C ₆₀ aryl group or a C ₁ to C ₆₀ A C ₆ to C ₆₀ aromatic hydrocarbon ring substituted or unsubstituted with an alkyl group of ₁ to ₂₀ carbon atoms; Or a C ₂ to C ₆₀ aromatic heterocycle which is substituted or unsubstituted with an aryl group of C ₆ to C ₆₀ ,
R10 to R16 are the same or different from each other, and each independently hydrogen; Or a C ₆ to C ₆₀ aryl group,
[Chemical Formula 5]

In Formula 5,
At least one of X1 to X3 is N, and the others are each independently N or CR35,
R17, R18 and R35 are the same or different from each other, and each independently hydrogen; And an aryl group of C ₆ to C ₆₀ , or two or more groups adjacent to each other are bonded to each other to form a C ₆ to C ₆₀ aromatic hydrocarbon ring,
R19 to R21 are hydrogen,
R27 to R34 are the same or different from each other, and each independently hydrogen; A C ₆ to C ₆₀ aryl group; A C ₂ to C ₆₀ heteroaryl group; And amine groups substituted or unsubstituted with C ₆ to C ₆₀ aryl groups, or two or more groups adjacent to each other may be bonded to each other to form a C ₆ to C ₆₀ aryl group or a C ₁ to C ₆₀ alkyl group, An unsubstituted C ₆ to C ₆₀ hydrocarbon ring or a C ₂ to C ₆₀ hetero ring,
At least one of R22 to R26 is -CN and the others are each independently hydrogen; Or an aryl group of C ₆ to C ₆₀ . The organic electroluminescent device according to claim 8, wherein the compound represented by Formula 4 is represented by any one of the following compounds:

The organic electroluminescent device according to claim 8, wherein the compound represented by Formula 5 is represented by any one of the following compounds:

9. The compound according to claim 8, wherein the heterocyclic compound; And a compound represented by the formula (4) or (5) as a host material in a light emitting layer.

Images