KR20160029721A

KR20160029721A - Multicyclic compound including nitrogen and organic electronic device using the same

Info

Publication number: KR20160029721A
Application number: KR1020150126295A
Authority: KR
Inventors: 차용범; 김진주
Original assignee: 주식회사 엘지화학
Priority date: 2014-09-05
Filing date: 2015-09-07
Publication date: 2016-03-15
Also published as: KR101804630B1

Abstract

The present invention relates to a nitrogen-containing polycyclic compound, and an organic electronic device comprising the same. One embodiment of the present invention provides a compound represented by chemical formula 1. Lifespan properties of the device are improved by thermal stability of the compound, when the compound is used in the organic electronic device.

Description

TECHNICAL FIELD [0001] The present invention relates to a nitrogen-containing polycyclic compound and an organic electronic device using the same. BACKGROUND ART < RTI ID = 0.0 >

This specification claims the benefit of the filing date of Korean Patent Application No. 10-2014-0118389 filed on September 05, 2014, the entire contents of which are incorporated herein by reference.

The present specification relates to nitrogen-containing polycyclic compounds and organic electronic devices using the same.

An organic electronic device means an element requiring charge exchange between an electrode and an organic material using holes and / or electrons. The organic electronic device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Type electric device. The second type is an electronic device that injects holes and / or electrons into an organic semiconductor that interfaces with an electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.

Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like. These devices may be used as a hole injecting or transporting material, an electron injecting or transporting material, need. Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, hole injecting or transporting materials, electron injecting or transporting materials, or light emitting materials act on a similar principle.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

Materials used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. In addition, the luminescent material can be classified into blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color. On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the efficiency of light emission through the light emitting layer.

In order for the organic luminescent device to sufficiently exhibit the above-described excellent characteristics, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently developed yet. Therefore, development of new materials is continuously required, and the necessity of developing such materials is the same in other organic electronic devices described above.

Korean Patent Publication No. 2011-0125637

It is an object of the present invention to provide a nitrogen-containing polycyclic compound and an organic electronic device including the same.

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

[Chemical Formula 1]

In Formula 1,

Cy1 is represented by any one of the following formulas (2) to (4)

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

* Is the connecting site,

t is an integer from 0 to 10,

u is an integer of 1 to 10,

When t is an integer of 2 or more, a plurality of L1s are the same or different from each other,

When u is an integer of 2 or more, plural Y < 1 > s are the same or different from each other,

L1 is a substituted or unsubstituted arylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted carbazolylene group; A heteroarylene group containing one or two N atoms; Or a substituted or unsubstituted heteroarylene group containing at least one of O and S atoms,

Y1 is hydrogen; heavy hydrogen; A halogen group; Cyano; -N (Z1) (Z2); A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted carbazole group; A heteroaryl group containing one or two N atoms; Or a substituted or unsubstituted heteroaryl group containing at least one of O and S atoms,

Z 1 and Z 2 are the same or different and are each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazolyl group; A heteroaryl group containing one or two N atoms; Or a substituted or unsubstituted heteroaryl group containing at least one of O and S atoms,

a and c are each independently an integer of 0 to 2,

b and d are each independently an integer of 0 to 3,

e is an integer of 0 to 1,

f is an integer of 0 to 4,

When a is an integer of 2 or more, a plurality of R 5 's are the same as or different from each other,

When b is an integer of 2 or more, a plurality of R 6 are the same or different from each other,

When c is an integer of 2 or more, plural R < 7 > are the same as or different from each other,

When d is an integer of 2 or more, the plural R < 8 > s are the same as or different from each other,

When f is an integer of 2 or more, a plurality of R 10 s are the same or different from each other,

R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroaryl group containing at least one of N, O and S atoms, or may be bonded to adjacent groups to form a ring,

X is - (A) _m - (B) _n ,

m is an integer of 0 to 10,

n is an integer of 1 to 10,

When m is an integer of 2 or more, plural A's are the same or different from each other,

When n is an integer of 2 or more, a plurality of B's are the same as or different from each other,

A is a substituted or unsubstituted arylene group; A substituted or unsubstituted alkenylene group; Or a substituted or unsubstituted heteroarylene group containing at least one of N, O and S atoms,

B is hydrogen; heavy hydrogen; A halogen group; Cyano; -N (Z3) (Z4); A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group containing at least one of N, O and S atoms,

Z3 and Z4 are the same or different and each independently represents a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted heteroaryl group containing at least one of N, O and S atoms.

Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of the formula (1) .

The compound of the present invention can be used in an organic electronic device as an organic layer material such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, Or as a hole transport material. When the compound of the present invention is used in an organic electronic device including an organic light emitting device, the driving voltage of the device is lowered, the light efficiency is improved, and the lifetime characteristics of the device can be improved by the thermal stability of the compound.

1 to 5 are cross-sectional views illustrating the structure of an organic electronic device according to the present invention.

Hereinafter, the present invention will be described in detail.

The present invention provides a compound represented by the above formula (1).

In the present specification,

Refers to the connected area.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

The term "substituted or unsubstituted" in the present specification refers to a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxy, alkyl, cycloalkyl, An alkyl group, an aryl group, a carbazole group, an arylalkyl group, an arylalkenyl group, a heteroaryl group, and an acetylene group, each of which is substituted with at least one substituent selected from the group consisting of a halogen atom, Means that at least two of the substituents exemplified above are substituted or unsubstituted with at least one substituent selected from the group consisting of the above-mentioned groups, or substituted or unsubstituted with a substituent connected thereto. 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.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

The length of the alkyl group contained in the compound only affects the application of the compound to the organic electronic device, for example, the application of the vacuum evaporation method or the solution application method, so the number of carbon atoms of the alkyl group is not particularly limited.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.

In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, , A fluorenyl group and the like, but are not limited thereto. The fluorenyl group may have a substituent, and the substituents may be bonded to each other to form a ring. For example, the fluorenyl group includes, but is not limited to, the following structures.

In the present specification, the heteroaryl group to be applied to R1 to R10, A, B, Z3 and Z4 is a ring group containing at least one of O, N and S as a heteroatom and the number of carbon atoms is not particularly limited, 60 < / RTI > Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group. Examples include, but are not limited to, compounds having the following structural formulas.

In the present specification, the heteroaryl group to be applied to L 1, Y 1, Z 1 and Z 2 may be a ring group containing O or S as a heteroatom, and may further include N as a heteroatom. The number of carbon atoms is not particularly limited, 60 < / RTI > Examples include a pyrrolyl group, an imidazole group, a pyridyl group, a pyrazinyl group, a thiophene group, a furan group, a thiazole group, an oxazole group, an oxadiazole group, a quinolinyl group, an isoquinoline group and an acridyl group. For example, there are compounds such as the following structural formulas, but are not limited thereto.

In the present specification, the number of carbon atoms of the heteroaryl group containing one or two N atoms to be applied to L1, Y1, Z1 and Z2 is not particularly limited, but preferably 3 to 60 carbon atoms. Examples of the heteroaryl group containing one or two N groups include, but are not limited to, the following structural formulas.

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

In the present specification, examples of the arylamine group include a substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted polycyclic diarylamine group, or a substituted or unsubstituted monocyclic and polycyclic diaryl Amine group.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group and the aralkylamine group is the same as the aforementioned aryl group.

In the present specification, the alkyl group in the alkylthio group, alkylsulfoxy group, alkylamine group, and aralkylamine group is the same as the alkyl group described above.

In the present specification, the term " forming a ring by bonding to adjacent groups " means forming a ring by bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Or a substituted or unsubstituted aromatic heterocycle.

As used herein, the term "adjacent group" means a group in which the substituent is substituted with an atom directly bonded to the atom to which the substituted atom is substituted, a substituent having the closest stereostructure to the substituent, It can mean. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent groups ".

In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.

In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.

As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more of the N, O, or S atoms as heteroatoms.

As used herein, an aromatic heterocycle refers to an aromatic ring containing one or more of N, O, or S atoms as heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

In one embodiment of the present invention, the compound represented by Formula 1 is represented by Formula 5 . &Lt; / RTI >

[Chemical Formula 5]

In Formula 5,

L1, Y1, X, R1 to R6, a, b, t and u are as defined in the above formula (1).

In one embodiment of the present invention, the compound represented by Formula 1 may be represented by Formula 6 below.

[Chemical Formula 6]

In Formula 6,

R1, R4, R7, R8, c, d, t and u are as defined in the above formula (1).

In one embodiment of the present invention, the compound represented by Formula 1 may be represented by Formula 7 below.

(7)

In Formula 7,

R1, R4, R9, R10, e, f, t and u are as defined in the above formula (1).

In one embodiment of the present disclosure, m is an integer from 0 to 5.

In one embodiment of the present disclosure, m is an integer from 0 to 4.

In one embodiment of the present disclosure, m is an integer from 0 to 3.

In one embodiment of the present disclosure, m is an integer from 0 to 2.

In one embodiment of the present disclosure, m is 0 or 1.

In one embodiment of the present disclosure, m is one.

In one embodiment of the present disclosure, m is zero.

In one embodiment of the present disclosure, n is an integer from 1 to 5.

In another embodiment, n is an integer from 1 to 4.

In another embodiment, n is an integer from 1 to 3.

In one embodiment of the present disclosure, n is 1 or 2.

In one embodiment of the present disclosure, n is 2.

In one embodiment of the present disclosure, n is one.

In one embodiment of the present specification, A is a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C6 to C30 substituted or unsubstituted N, O and S atom Lt; / RTI > is a substituted heteroarylene group.

In one embodiment of the present specification, A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, A is a substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted divalent naphthalene group; A substituted or unsubstituted carbazolylene group; A substituted or unsubstituted divalent dibenzofurane group; A substituted or unsubstituted divalent dibenzothiophene group; A substituted or unsubstituted divalent pyridine group; A substituted or unsubstituted divalent pyrimidine group; Or a substituted or unsubstituted divalent triazine group. When these substituents are substituted, they may be substituted with at least one substituent selected from the group consisting of deuterium, an alkyl group, a hydroxyl group, a halogen group, a nitro group and a cyano group.

In one embodiment of the present specification, A is a substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenylene group; Or a substituted or unsubstituted divalent naphthalene group.

In one embodiment of the present specification, A represents a substituted or unsubstituted carbazolylene group; A substituted or unsubstituted divalent pyridine group; A substituted or unsubstituted divalent pyrimidine group; Or a substituted or unsubstituted divalent triazine group.

In another embodiment, A is a substituted or unsubstituted carbazolylene group; A substituted or unsubstituted divalent dibenzofurane group; Or a substituted or unsubstituted divalent dibenzothiophene group.

In one embodiment of the present specification, A is a substituted or unsubstituted phenylene group.

In one embodiment of the present disclosure, A is a phenylene group.

In one embodiment of the present specification, A is a substituted or unsubstituted fluorenylene group.

In one embodiment of the present disclosure, A is a fluorenylene group.

In one embodiment of the present specification, A is a substituted or unsubstituted divalent naphthalene group.

In one embodiment of the present disclosure, A is a bivalent naphthalene group.

In one embodiment of the present invention, A is a substituted or unsubstituted carbazolylene group.

In one embodiment of the present disclosure, A is a carbazolylene group.

In one embodiment of the present specification, A is a substituted or unsubstituted divalent pyridine group.

In one embodiment of the present disclosure, A is a divalent pyridine group.

In one embodiment of the present specification, A is a substituted or unsubstituted divalent pyrimidine group.

In another embodiment, A is a pyrimidine group.

In one embodiment of the present specification, A is a substituted or unsubstituted divalent triazine group.

In one embodiment of the present specification, A is a bivalent triazine group.

In one embodiment of the present specification, B is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C6-C30 heteroaryl group.

In one embodiment of the present specification, B is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, B is a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, B represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted silyl group. When these substituents are further substituted, they include deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 4 to 20 carbon atoms.

In one embodiment of the present specification, B represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, B is a substituted or unsubstituted phenyl group.

In one embodiment of the present disclosure, B is deuterium; A halogen group; A phenyl group substituted or unsubstituted with a substituted or unsubstituted alkyl group.

In one embodiment of the present disclosure, B is deuterium; A halogen group; A phenyl group substituted or unsubstituted with a methyl group.

In another embodiment, B is a phenyl group that is disubstituted with a carbazole group.

In one embodiment of the present specification, B is a phenyl group substituted or unsubstituted with cyano group.

In one embodiment of the present disclosure, B is a phenyl group.

In one embodiment of the present specification, B is a substituted or unsubstituted naphthalene group.

In one embodiment of the present disclosure, B is a naphthalene group.

In one embodiment of the present specification, B is a substituted or unsubstituted phenanthrene group.

In one embodiment of the present disclosure, B is a phenanthrene group.

In one embodiment of the present specification, B is a phenanthrene group substituted or unsubstituted with a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, B is a substituted or unsubstituted phenanthrene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, B is a phenanthrene group substituted or unsubstituted with a methyl group.

In one embodiment of the present specification, B is a substituted or unsubstituted triphenylene group.

In one embodiment of the present disclosure, B is a triphenylene group.

In another embodiment, B is a substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, B is a substituted or unsubstituted carbazole group; Or a substituted or unsubstituted benzocarbazole group.

In one embodiment of the present specification, B is a substituted or unsubstituted carbazole group.

In one embodiment of the present invention, B is a substituted or unsubstituted carbazol group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In another embodiment, B is a carbazolyl group substituted or unsubstituted with a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, B is a carbazol group substituted or unsubstituted with a substituted or unsubstituted biphenyl group.

In one embodiment of the present disclosure, B is a carbazole group.

In one embodiment of the present specification, B is a substituted or unsubstituted benzocarbazole group.

In one embodiment of the present specification, B is a substituted or unsubstituted benzocarbazole group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In another embodiment, B is a benzocarbazole group substituted or unsubstituted with a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, B is a benzocarbazole group.

In one embodiment of the present specification, B is a substituted or unsubstituted thiophene group.

In one embodiment of the present specification, B is a thiophene group.

In one embodiment of the present disclosure, B is a substituted or unsubstituted dibenzofurane group.

In one embodiment of the present specification, B is a dibenzofurane group substituted or unsubstituted with cyano group.

In one embodiment of the present specification, B is a dibenzofurane group.

In one embodiment of the present specification, B is a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, B is a dibenzothiophene group substituted or unsubstituted with cyano group.

In one embodiment of the present specification, B is a dibenzothiophene group.

In one embodiment of the present disclosure, B is a substituted or unsubstituted quinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted triazine group.

In another embodiment, B is a quinolinyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, B is a quinolinyl group substituted or unsubstituted with a phenyl group.

In one embodiment of the present disclosure, B is a quinoline group.

In one embodiment of the present invention, B is a quinazoline group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, B is a quinazoline group substituted or unsubstituted with a phenyl group.

In one embodiment of the present disclosure, B is a quinazoline group.

In one embodiment of the present disclosure, B is

And may be further substituted.

In one embodiment of the present disclosure, B is

And may be further substituted.

In one embodiment of the present disclosure, B is

And may be further substituted.

In another embodiment, B is

And may be further substituted.

In one embodiment of the present disclosure, B is

And may be further substituted.

In one embodiment of the present specification, B is a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, B is a pyridine group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, B is a pyridine group substituted or unsubstituted with a phenyl group.

In one embodiment of the present disclosure, B is a pyridine group.

In one embodiment of the present specification, B is a pyrimidine group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present invention, B is a pyrimidine group substituted or unsubstituted with a phenyl group.

In one embodiment of the present disclosure, B is a pyrimidine group.

In another embodiment, B is a triazine group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 4 to 20 carbon atoms.

In one embodiment of the present specification, B is a triazine group substituted or unsubstituted with a pyridine group.

In one embodiment of the present invention, B is a triazine group substituted or unsubstituted with a phenyl group.

In one embodiment of the present invention, B is a triazine group substituted or unsubstituted with a biphenyl group.

In one embodiment of the present specification, B is a triazine group substituted or unsubstituted with a fluorenyl group.

In one embodiment of the present invention, B is a triazine group substituted or unsubstituted with a phenanthrene group.

In another embodiment, B is a triazine group.

In one embodiment of the present specification, B is a substituted or unsubstituted silyl group.

In one embodiment of the present invention, B is a silyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present disclosure, B is a silyl group substituted with a phenyl group.

In one embodiment of the present specification, B is a substituted or unsubstituted arylphosphine group.

In one embodiment of the present invention, B is a phosphine oxide group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, B is a phosphine oxide group substituted or unsubstituted with a phenyl group or a naphthalene group.

In one embodiment of the present disclosure, B is a phosphine oxide group.

In one embodiment of the present disclosure, B is -N (Z3) (Z4).

In one embodiment of the present specification, Z 3 and Z 4 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 6 -C 30 heteroaryl group containing at least one of N, O and S atoms.

In one embodiment of the present specification, Z3 and Z4 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quaterphenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted naphthalene group.

In one embodiment of the present invention, X is exemplified by any of the substituents described in [Table 1] below, but is not limited thereto.

[Example Chart 1]

In one embodiment of the present specification, L 1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted 6 to 30 carbon atom containing at least one of substituted or unsubstituted N, O and S atoms Lt; / RTI > is a substituted heteroarylene group.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted divalent naphthalene group; A substituted or unsubstituted carbazolylene group; A substituted or unsubstituted divalent dibenzofurane group; A substituted or unsubstituted divalent dibenzothiophene group; A substituted or unsubstituted divalent pyridine group; A substituted or unsubstituted divalent pyrimidine group; Or a substituted or unsubstituted divalent triazine group. When these substituents are substituted, they may be substituted with at least one substituent selected from the group consisting of deuterium, an alkyl group, a hydroxyl group, a halogen group, a nitro group and a cyano group.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenylene group; Or a substituted or unsubstituted divalent naphthalene group.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted carbazolylene group; A substituted or unsubstituted divalent pyridine group; Or a substituted or unsubstituted divalent pyrimidine group.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted carbazolylene group; A substituted or unsubstituted divalent dibenzofurane group; Or a substituted or unsubstituted divalent dibenzothiophene group.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted phenylene group.

In one embodiment of the present disclosure, L1 is a phenylene group.

In one embodiment of the present invention, L 1 is a substituted or unsubstituted fluorenylene group.

In one embodiment of the present disclosure, L1 is a fluorenylene group.

In one embodiment of the present specification, L1 is a substituted or unsubstituted divalent naphthalene group.

In one embodiment of the present disclosure, L1 is a divalent naphthalene group.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted carbazolylene group.

In one embodiment of the present disclosure, L1 is a carbazolylene group.

In one embodiment of the present specification, L < 1 > is a substituted or unsubstituted divalent pyridine group.

In one embodiment of the present specification, L < 1 > is a divalent pyridine group.

In one embodiment of the present invention, L 1 is a substituted or unsubstituted divalent pyrimidine group.

In another embodiment, L < 1 > is a pyrimidine group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C6-C30 heteroaryl group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted C6 to C30 aryl group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Y1 represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted silyl group. When these substituents are further substituted, they include deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 4 to 20 carbon atoms.

In one embodiment of the present specification, Y1 represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted phenyl group.

In one embodiment of the present disclosure, Y1 is deuterium; A halogen group; A phenyl group substituted or unsubstituted with a substituted or unsubstituted alkyl group.

In one embodiment of the present disclosure, Y1 is deuterium; A halogen group; A phenyl group substituted or unsubstituted with a methyl group.

In another embodiment, Y1 is a phenyl group that is disubstituted with a carbazole group.

In one embodiment of the present specification, Y1 is a phenyl group substituted or unsubstituted with cyano group.

In one embodiment of the present specification, Y1 is a phenyl group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted naphthalene group.

In one embodiment of the present specification, Y1 is a naphthalene group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted phenanthrene group.

In one embodiment of the present specification, Y1 is a phenanthrene group.

In one embodiment of the present specification, Y1 is a phenanthrene group substituted or unsubstituted with a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted phenanthrene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, Y1 is a phenanthrene group substituted or unsubstituted with a methyl group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted triphenylene group.

In one embodiment of the present disclosure, Y1 is a triphenylene group.

In another embodiment, Y1 is a substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted carbazole group; Or a substituted or unsubstituted benzocarbazole group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted carbazol group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In another embodiment, Y1 is a carbazolyl group substituted or unsubstituted with a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Y1 is a carbazol group substituted or unsubstituted with a substituted or unsubstituted biphenyl group.

In one embodiment of the present specification, Y1 is a carbazole group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted benzocarbazole group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted benzocarbazole group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In another embodiment, Y1 is a benzocarbazole group substituted or unsubstituted with a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Y1 is a benzocarbazole group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted thiophene group.

In one embodiment of the present specification, Y1 is a thiophene group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted dibenzofurane group.

In one embodiment of the present specification, Y1 is a dibenzofurane group substituted or unsubstituted with cyano group.

In one embodiment of the present specification, Y1 is a dibenzofurane group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, Y1 is a dibenzothiophene group substituted or unsubstituted with cyano group.

In one embodiment of the present specification, Y1 is a dibenzothiophene group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted quinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted pyridine group; Or a substituted or unsubstituted pyrimidine group.

In another embodiment, Y1 is a quinolinyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Y1 is a quinoline group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Y1 is a quinoline group.

In one embodiment of the present specification, Y1 is a quinazoline group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Y1 is a quinazoline group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Y1 is a quinazoline group.

In one embodiment of the present disclosure, Y1 is

And may be further substituted.

In one embodiment of the present disclosure, Y1 is

And may be further substituted.

In one embodiment of the present disclosure, Y1 is

And may be further substituted.

In another embodiment, Y1 is

And may be further substituted.

In one embodiment of the present disclosure, Y1 is

And may be further substituted.

In one embodiment of the present disclosure, Y1 is

And may be further substituted.

In another embodiment, Y1 is

And may be further substituted.

In one embodiment of the present disclosure, Y1 is

And may be further substituted.

In one embodiment of the present disclosure, Y1 is

And may be further substituted.

In one embodiment of the present disclosure, Y1 is

And may be further substituted.

In one embodiment of the present disclosure, Y1 is

to be.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, Y1 is a pyridine group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Y1 is a pyridine group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Y1 is a pyridine group.

In one embodiment of the present specification, Y1 is a pyrimidine group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Y1 is a pyrimidine group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Y1 is a pyrimidine group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted silyl group.

In one embodiment of the present specification, Y1 is a silyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present disclosure, Y1 is a silyl group substituted with a phenyl group.

In one embodiment of the present specification, Y1 is a substituted or unsubstituted arylphosphine group.

In one embodiment of the present specification, Y1 is a phosphine oxide group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Y1 is a phosphine oxide group substituted or unsubstituted with a phenyl group or a naphthalene group.

In one embodiment of the present disclosure, Y1 is a phosphine oxide group.

In one embodiment of the present disclosure, Y1 is -N (Z1) (Z2).

In one embodiment of the present invention, Z 1 and Z 2 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C 6 -C 30 heteroaryl group containing at least one of N, O and S atoms.

In one embodiment of the present specification, Z 1 and Z 2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quaterphenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted naphthalene group.

In the present specification, in one embodiment, - (L1) t- (Y1) u may be exemplified by any one of the substituents described in [Table 2] below, but is not limited thereto.

[Example Chart 2]

In one embodiment of the present disclosure, R1 is hydrogen.

In one embodiment of the present disclosure, R 2 is hydrogen.

In one embodiment of the present disclosure, R 3 is hydrogen.

In one embodiment of the present disclosure, R4 is hydrogen.

In another embodiment R1 to R4 are hydrogen.

In one embodiment of the present disclosure, R5 is hydrogen.

In one embodiment of the present disclosure, R6 is hydrogen.

In one embodiment of the present disclosure, R5 and R6 are hydrogen.

In one embodiment of the present disclosure, R7 is hydrogen.

In one embodiment of the present disclosure, R8 is hydrogen.

In one embodiment of the present disclosure, R7 and R8 are hydrogen.

In one embodiment of the present disclosure, R9 is hydrogen.

In one embodiment of the present disclosure, R10 is hydrogen.

In one embodiment of the present disclosure, R9 and R10 are hydrogen.

In another embodiment, R1 to R10 are hydrogen.

In the present specification, preferable compounds as the hole injection layer are materials having a substituent that can lower the HOMO value than that used as the hole transport layer. That is, a carrier is easily transferred from ITO (indium tin oxide) to a hole transport layer. As such a substituent, materials including an arylamino group, an arylaminoaryl group, or a thiophenyl group are preferable. And R < 1 > to R < 10 >

In one embodiment of the present invention, the formula (1) may be represented by the following structures, but is not limited thereto.

The following structural formulas can be substituted with the substituents described in [Example 1] and [Example 2] above.

The compound of Formula 1 is characterized in that the carbazole structure has a core structure in which at least one benzene ring is condensed.

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap. As described above, since the core of the compound of Formula 1 contains limited conjugation, the energy band gap has a large property.

In this specification, it is possible to synthesize a compound having various energy bandgaps by introducing various substituents at L1, L2, X, Y1 or Y2 positions of the core structure having a large energy bandgap. Usually, it is easy to control the energy band gap by introducing a substituent to a core structure having a large energy band gap. However, when the core structure has a small energy band gap, it is difficult to control the energy band gap by introducing a substituent. In this specification, the HOMO and LUMO energy levels of a compound can be controlled by introducing various substituents at L, X or Y positions of the core structure having the above structure.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent used in a hole injecting layer material, a hole transporting layer material, a light emitting layer material, and an electron transporting layer material used in the production of an organic electronic device including the organic light emitting device into the core structure, Can be synthesized. For example, an arylamino group, a thiophenyl group, or an aryl group substituted with them may be introduced. Formula 1, in which an arylamino group or a thiophenyl group is introduced, exhibits HOMO of 5.6 to 5.1 eV and is very useful as a hole injecting and hole transporting layer.

Further, by introducing various substituents to the core structure, it is possible to finely control the energy band gap, improve the interfacial characteristics between the organic layers, and diversify the use of the materials.

Also, by controlling the number of amines contained in the substituent B, the HOMO, LUMO energy level and energy band gap can be finely controlled, while the interfacial characteristics between the organic materials can be improved and the use of the materials can be diversified.

In addition, the structure of the formula (1) can secure energy band gap and stability in a triplet state by introducing an appropriate substituent. From these results, various phosphorescent dopants ranging from red to blue can be used to apply not only fluorescence but also light emitting layers of phosphorescent devices.

In addition, the compound of Formula 1 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.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of the formula (1).

The organic electronic device may be selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), and a glass transistor.

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

In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound of the general formula (1).

In one embodiment of the present invention, the organic layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound of the above formula (1).

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound of the above formula (1).

In another embodiment, the organic material layer includes a light emitting layer and an electron transporting layer, and the electron transporting layer includes the compound of the above formula (1).

In another embodiment, the organic electronic device may be a normal type organic electronic device in which an anode, at least one organic material layer, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic electronic device may be an inverted type organic electronic device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

The organic electronic device according to the present invention may have a structure as shown in Figs. 1 to 5, but the present invention is not limited thereto.

1 shows an organic electronic device in which a substrate 1, an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6 and a cathode 7 are sequentially stacked Structure is illustrated.

2 illustrates the structure of an organic electronic device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, and a cathode 7 are sequentially stacked.

3 illustrates the structure of an organic electronic device in which a substrate 1, an anode 2, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked.

4 shows a structure of an organic electronic device in which a substrate 1, an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially laminated.

5 illustrates a structure of an organic electronic device in which a substrate 1, an anode 2, a light emitting layer 5, and a cathode 7 are sequentially laminated.

When the organic electronic device includes a plurality of organic layers, the organic layers may be formed of the same material or another material.

The organic electronic device of the present invention can be manufactured by materials and methods known in the art except that at least one layer of the organic material layer contains the compound of the above formula (1), that is, the compound represented by the above formula (1).

For example, the organic electronic device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic electronic device can be formed by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.

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

In addition to such a method, an organic electronic device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

In another embodiment, the first electrode is a cathode and the second electrode is a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention 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] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. 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.

The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

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

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

[ Example ]

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present application is not construed as being limited to the embodiments described later. The embodiments of the present application are provided to enable those skilled in the art to more fully understand the present invention.

The compound of formula (I) according to the present invention can be prepared by a multistage chemical reaction. The preparation of these compounds is described by the following Synthesis Examples and Preparation Examples. As shown in the following Synthesis Examples, some of the intermediate compounds are first prepared, and the intermediate compounds are converted to the core structure as shown in the Production Example to prepare the compounds of Formula (1).

Compounds of formula (1) can be prepared according to the same procedures and in the same manner as Reaction Scheme 1-1, Reaction Scheme 1-2, and Reaction Scheme 1-3 to prepare compounds corresponding to Formulas 5, 6 and 7, respectively. Although not intended to be limiting, reaction schemes are briefly described to aid understanding. Reaction Schemes 1-1 and 1-2 illustrate that various tetralone compounds transform the Formula 1 into the core structure of the formula of the present invention to produce the compounds of Formula 1 and Scheme 1-3 depicts the nitrobenzene group After the substitution, triphenylphosphine is used to prepare benzocarbazole-type compounds corresponding to Formula 1.

[ Synthetic example ]

<Reaction Scheme 1-1> 2- Bromo -11H- Benzo [a] carbazole Produce

1) 2- Bromo -11H- Benzo [a] carbazole Compound synthesis

<Reaction Scheme 1-2> 2- Bromo -7H- Benzo [c] carbazole Produce

1) 2- Bromo -7H- Benzo [c] carbazole Compound synthesis

<Reaction 1-3> 5- Bromo -7H- Benzo [c] carbazole Produce

1) Synthesis of 5- bromo- 7H- benzo [c] carbazole Compound synthesis

The central cores prepared in the reaction schemes 1-1 to 1-3 may introduce various substituents through a Suzuki coupling as shown in the following Production Examples, and may be produced by reacting an aryl group, a heteroaryl group, an arylamino group or the like A substituent can be introduced.

< Manufacturing example 1> Preparation of the following compound 2-1

1) Synthesis of the following compound 1-A

(15.5 g, 0.52 mol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (18.03 g, 0.63 mol) were added to a solution of the compound 2-bromo-11H- (200 ml) was added to the solution, and tetrakis- (triphenylphosphine) palladium (1.81 g, 1.57 mmol) was added thereto, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethanol (300 ml) to obtain Compound 1-A (19.8 g, yield: 83%).

MS [M + H] < ⁺ > = 459

2) Synthesis of the following compound 2-1

The compound 1-A (19.8 g, 0.43 mol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (12.67 g, 0.47 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere. After dissolving, sodium tert-butoxide (4.98 g, 0.52 mol) was added, and bis (tri-tert-butylphosphine) palladium (0.44 g, 0.08 mol) was added and the mixture was heated with stirring for 7 hours. The mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to give the above compound 2-1 (24.88 g, yield: 84%).

MS [M + H] < ⁺ > = 690

< Manufacturing example 2> Preparation of the following compound 2-2

1) Synthesis of the following compound 1-B

Benzo [a] carbazole (17.4 g, 0.59 mol) and (4- (9H-carbazol-90yl) phenyl) boronic acid (19.07 g, 0.27 mol) in a nitrogen atmosphere. (210 ml) was added to the solution, and tetrakis- (triphenylphosphine) palladium (1.92 g, 1.62 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethanol (300 ml) to give Compound 1-B (20.5 g, yield 80%).

MS [M + H] < ⁺ > = 344

2) Synthesis of the following compound 2-2

The compound 1-B (20.5 g, 0.46 mol) and 2-chloro-4,6-diphenylpyrimidine (12.98 g, 0.50 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere, (5.12 g, 0.53 mol) was added and bis (tri-tert-butylphosphine) palladium (0.47 g, 0.09 mmol) was added thereto, followed by heating with stirring for 5 hours. The mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was subjected to column chromatography using tetrahydrofuran: hexane = 1: 7 to prepare the above compound 2-2 (25.12 g, yield: 83%).

MS [M + H] < ⁺ > = 689

< Manufacturing example 3> Preparation of Compound 2-3

1) Synthesis of the following compound 1-C

Benzo [a] carbazole (17.8 g, 0.60 mol) and (9-phenyl-9H-carbazol-2-yl) boronic acid (19.77 g, 0.28 mol) were added to a solution of the compound 2-bromo- (2.21 g, 1.78 mmol) of tetrakis- (triphenylphosphine) palladium was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, and the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to give Compound 1-C (22.5 g, yield: 88%).

MS [M + H] < ⁺ > = 459

2) Synthesis of the compound of the following compound 2-3

After completely dissolving the compound 1-C (22.5 g, 0.54 mol) and 2-chloro-4,6-diphenylpyridine (14.3 g, 0.55 mol) in 240 ml of xylene, sodium-tert-butoxide , 0.59 mol) was added, and bis (tri-tert-butylphosphine) palladium (0.52 g, 0.1 mol) was added thereto, followed by heating and stirring for 7 hours. The reaction mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was subjected to column chromatography using tetrahydrofuran: hexane = 1: 7 to prepare the compound 2-3 (23.15 g, yield 79%).

MS [M + H] < ⁺ > = 687

< Manufacturing example 4> Preparation of compound 2-4

1) Synthesis of the following compound 1-D

(20.9 g, 0.30 mol) was added to 320 ml of tetrahydrofuran in a nitrogen atmosphere, to the solution of the compound 2-bromo- 11H-benzo [a] carbazole (19.1 g, 0.50 mol) After completely dissolved, a 2M aqueous potassium carbonate solution (160 ml) was added, tetrakis- (triphenylphosphine) palladium (1.6 g, 1.3 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to obtain the compound 1-D (18.1 g, yield 70%).

MS [M + H] < ⁺ > = 461

2) Synthesis of the following compound 2-4

After completely dissolving the compound 1-D (18.1 g, 0.39 mol) and 4-bromo-1,1'-biphenyl (10.04 g, 0.43 mol) in 240 ml of xylene in a nitrogen atmosphere, sodium tert- (4.54 g, 0.43 mol) was added, and bis (tri-tert-butylphosphine) palladium (0.48 g, 0.9 mol) was added thereto, followed by heating with stirring for 7 hours. The temperature was lowered to room temperature, the salt was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 3 to obtain the compound 2-4 (51 g, yield: 72%).

MS [M + H] < ⁺ > = 613

< Manufacturing example 5> Preparation of the following compound 2-5

1) Synthesis of the following compound 1-E

(19.1 g, 0.50 mol) and (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) (20.9 g, 0.30 mol) was completely dissolved in 320 ml of tetrahydrofuran. To the mixture was added 2M potassium carbonate aqueous solution (160 ml), tetrakis- (triphenylphosphine) palladium (1.6 g, 1.3 mmol) Lt; / RTI > The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to give Compound 1-E.

2) Synthesis of the following compound 2-5

After completely dissolving the compound 1-E (18.1 g, 0.39 mol) and 4-bromo-1,1'-biphenyl (10.04 g, 0.43 mol) in 240 ml of xylene in a nitrogen atmosphere, sodium tert- (4.54 g, 0.43 mol) was added, and bis (tri-tert-butylphosphine) palladium (0.48 g, 0.9 mol) was added thereto, followed by heating with stirring for 7 hours. The temperature was lowered to room temperature, the salt was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 3 to prepare Compound 2-5.

MS [M + H] < ⁺ > = 765

< Production Example 6 > Preparation of the following compounds 2-6

1) Synthesis of the following compound 1-F

(9.1 g, 0.50 mol) and (9-phenyl-9H-carbazol-3-yl) boronic acid (20.9 g, 0.30 mol) were added to a solution of the compound 2-bromo-11H- (1.6 ml, 1.3 mmol) was added to the solution, and the mixture was stirred under heating for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to give Compound 1-F.

2) Synthesis of the following compound 2-6

After completely dissolving the compound 1-F (18.1 g, 0.39 mol) and 4-bromo-1,1'-biphenyl (10.04 g, 0.43 mol) in 240 ml of xylene in a nitrogen atmosphere, sodium tert- (4.54 g, 0.43 mol) was added, and bis (tri-tert-butylphosphine) palladium (0.48 g, 0.9 mol) was added thereto, followed by heating with stirring for 7 hours. The mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 3 to prepare Compound 2-6.

MS [M + H] < ⁺ > = 611

< Production Example 7 > Preparation of the following compounds 2-7

1) Synthesis of the following chemical 1-G

(19.9 g, 0.50 mol), (4- (9H-carbazol-9-yl) phenyl) boronic acid (20.9 g, 0.30 mol) (1.6 g, 1.3 mmol) was added to the solution, and the mixture was heated with stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to give Compound 1-G.

2) Synthesis of the following compound 2-7

The compound 1-G (18.1 g, 0.39 mol) and 4-bromo-1,1'-biphenyl (10.04 g, 0.43 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere, sodium tert- (4.54 g, 0.43 mol) was added, and bis (tri-tert-butylphosphine) palladium (0.48 g, 0.9 mol) was added thereto, followed by heating with stirring for 7 hours. The temperature was lowered to room temperature, the salt was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 3 to prepare Compound 2-7.

MS [M + H] < ⁺ > = 611

< Production Example 8 > Preparation of the following compounds 2-8

1) Synthesis of the following compound 2-8

The compound 1-A (19.8 g, 0.43 mol) and 2-chloro-4-phenylquinazoline (12.67 g, 0.47 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere, sodium tert- g, 0.52 mol), and bis (tri-tert-butylphosphine) palladium (0.44 g, 0.08 mol) was added thereto, followed by heating and stirring for 7 hours. The mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare Compound 2-8.

MS [M + H] < ⁺ > = 663

< Production Example 9 > Preparation of the following compounds 2-9

1) Synthesis of Compound 2-9

The compound 1-A (19.8 g, 0.43 mol) and 2-chloro-4- (naphthalen-2-yl) quinazoline (12.67 g, 0.47 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere, (tert-butylphosphine) palladium (0.44 g, 0.08 mol) was added thereto, followed by heating and stirring for 7 hours. The mixture was cooled to room temperature, filtered to remove the salt, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the above compound 2-19.

MS [M + H] < ⁺ > = 713

< Production Example 10 > Preparation of the following compounds 2-10

1) Synthesis of compound 2-10 below

The compound 1-A (19.8 g, 0.43 mol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (12.67 g, 0.47 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere. After dissolving, sodium tert-butoxide (4.98 g, 0.52 mol) was added, and bis (tri-tert-butylphosphine) palladium (0.44 g, 0.08 mol) was added and the mixture was heated with stirring for 7 hours. After the temperature was lowered to room temperature, the salt was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare Compound 2-10.

MS [M + H] < ⁺ > = 739

< Production Example 11 > Preparation of the following compounds 2-11

1) Synthesis of the following compound 1-H

(15.5 g, 0.52 mol) and (dibenzo [b, d] furan-2-yl) boronic acid (18.03 g, 0.63 mol) were added to a solution of the compound 2-bromo-11H- (200 ml) was added to the solution, and tetrakis- (triphenylphosphine) palladium (1.81 g, 1.57 mmol) was added thereto, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethanol (300 ml) to give Compound 1-H.

2) Synthesis of Compound 2-11 below

The compound 1-H (19.8 g, 0.43 mol) and 2-chloro-4-phenylquinazoline (12.67 g, 0.47 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere, sodium tert- g, 0.52 mol), and bis (tri-tert-butylphosphine) palladium (0.44 g, 0.08 mol) was added thereto, followed by heating and stirring for 7 hours. The mixture was cooled to room temperature, filtered to remove the salt, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the above compound 2-11.

MS [M + H] < ⁺ > = 588

< Production Example 12 > Preparation of the following compounds 2-12

1) Synthesis of the following compound 2-12

The compound 1-H (19.8 g, 0.43 mol) and 2-chloro-4- (naphthalene-2-yl) quinazoline (12.67 g, 0.47 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere, (Tert-butylphosphine) palladium (0.44 g, 0.08 mol) was added thereto, followed by heating and stirring for 7 hours. The temperature was lowered to room temperature, the salt was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the above compound 2-12.

MS [M + H] < ⁺ > = 638

< Production Example 13 > Preparation of the following compounds 2-13

1) Synthesis of Compound 1-I below

(15.5 g, 0.52 mol) and (dibenzo [b, d] thiophen-2-yl) boronic acid (18.03 g, 0.63 mol) were added to a solution of the compound 2-bromo-11H- (200 ml) was added to the solution, and tetrakis- (triphenylphosphine) palladium (1.81 g, 1.57 mmol) was added thereto, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 300 ml of ethanol to prepare Compound 1-I.

2) Synthesis of the following compound 2-13

The compound 1-I (19.8 g, 0.43 mol) and 2-chloro-4-phenylquinazoline (12.67 g, 0.47 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere and sodium tert-butoxide g, 0.52 mol), and bis (tri-tert-butylphosphine) palladium (0.44 g, 0.08 mol) was added thereto, followed by heating and stirring for 7 hours. The reaction mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the above compound 2-13.

MS [M + H] < ⁺ > = 604

< Production Example 14 > Preparation of the following compounds 2-14

1) Synthesis of the following compound 2-14

(19.8 g, 0.43 mol) and 2-chloro-4- (naphthalen-2-yl) quinazoline (12.67 g, 0.47 mol) were completely dissolved in 240 ml of xylene in a nitrogen atmosphere, (tert-butylphosphine) palladium (0.44 g, 0.08 mol) was added thereto, followed by heating and stirring for 7 hours. The mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the above compound 2-14.

MS [M + H] < ⁺ > = 654

< Production Example 15 > Preparation of the following compounds 2-15

1) Synthesis of the following compound 2-15

(19.8 g, 0.43 mol) and 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (12.67 g, 0.47 mol) were dissolved in xylene (0.44 g, 0.08 mol) of bis (tri-tert-butylphosphine) palladium was added thereto, and the mixture was heated with stirring for 7 hours. Respectively. The reaction mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the above compound 2-15.

MS [M + H] < ⁺ > = 766

< Production Example 16 > Preparation of the following compounds 2-16

1) Synthesis of the following compound 1-J

Benzo [a] carbazole (15.5 g, 0.52 mol) and phenylboronic acid (18.03 g, 0.63 mol) were dissolved in 400 ml of tetrahydrofuran in a nitrogen atmosphere, and a 2M aqueous potassium carbonate solution 200 ml) was added, tetrakis- (triphenylphosphine) palladium (1.81 g, 1.57 mmol) was added, and the mixture was heated with stirring for 2 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethanol (300 ml) to give Compound 1-J.

2) Synthesis of Compound 2-16 below

The compound 1-J (19.8 g, 0.43 mol) and 4'-bromo-N, N-diphenyl- [1,1'- biphenyl] -4- amine (12.67 g, 0.47 mol) (0.44 g, 0.08 mol) of bis (tri-tert-butylphosphine) palladium was added thereto, and the mixture was stirred for 7 hours Followed by heating and stirring. The mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the above compound 2-16.

MS [M + H] < ⁺ > = 613

< Production Example 17 > Preparation of the following compounds 2-17

1) Synthesis of the following compound 2-17

The compound 1-J (19.8 g, 0.43 mol) and N, N-di ([1,1'-biphenyl] -4-yl) Phenyl) -4-amine (12.67 g, 0.47 mol) was dissolved in 240 ml of xylene and sodium tert-butoxide (4.98 g, 0.52 mol) Palladium (0.44 g, 0.08 mol) was added thereto, followed by heating and stirring for 7 hours. The mixture was cooled to room temperature, filtered to remove the salt, and then concentrated under reduced pressure. The residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 5 to prepare the above compound 2-17.

MS [M + H] < ⁺ > = 765

< Production Example 18 > Preparation of the following compounds 2-18 to 2-34

1) Synthesis of the following compounds 2-18 to 2-34

Preparation of the above compounds 2-1 to 2-17 except that 2-bromo-7H-benzo [c] carbazole was used instead of 2-bromo-11H-benzo [a] , The compounds 2-18 to 2-34 were prepared.

< Production Example 19 > Preparation of the following compounds 2-35 to 2-51

1) Synthesis of the following compounds 2-35 to 2-51

Preparation of the above-mentioned compounds 2-1 to 2-17 except that 5-bromo-7H-benzo [c] carbazole was used instead of 2-bromo-11H-benzo [a] , The above compounds 2-35 to 2-51 were prepared.

< Experimental Example 1>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

[NPB]

Subsequently, the following compound N - ([1,1'-bisphenyl] -4-yl) -N- (4- (11 - ([1,1'-biphenyl] -4 -yl) -11H-benzo [a] carbazole-5-yl) phenyl) - [1,1'-biphenyl] -4-amine (100A) was vacuum deposited to form an electron blocking layer.

[EB1]

Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

[BH]

[BD]

[ET1]

[LiQ]

The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 < ^-6 > torr, thereby fabricating an organic light emitting device.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-4 was used instead of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-5 was used in place of Compound EB1 in Experimental Example 1.

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-6 was used in place of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-7 was used instead of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-16 was used in place of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-17 was used instead of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-21 was used instead of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-22 was used instead of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-23 was used instead of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-24 was used in place of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-33 was used instead of Compound EB1 in Experimental Example 1.

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-34 was used in place of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-38 was used in place of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-39 was used instead of Compound EB1 in Experimental Example 1.

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-40 was used in place of Compound EB1 in Experimental Example 1.

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 2-41 was used in place of Compound EB1 in Experimental Example 1.

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-50 was used in place of Compound EB1 in Experimental Example 1.

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 2-51 was used in place of Compound EB1 in Experimental Example 1.

&Lt; Comparative Example 1-1 >

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound HT1 was used in place of Compound EB1 in Experimental Example 1.

[HT1]

&Lt; Comparative Example 1-2 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT2 was used in place of Compound EB1 in Experimental Example 1.

[HT2]

&Lt; Comparative Example 1-3 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT3 was used in place of Compound EB1 in Experimental Example 1.

[HT3]

&Lt; Comparative Example 1-4 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound HT4 was used in place of Compound EB1 in Experimental Example 1.

[HT4]

When current was applied to the organic light-emitting devices fabricated by Experimental Examples 1-1 to 1-18 and Comparative Examples 1-1 to 1-4, the results shown in Table 1 below were obtained.

division compound
(Electron inhibiting layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1 Compound EB1 4.11 5.33 (0.138, 0.127) Experimental Example 1-1 Compound 2-4 3.94 5.35 (0.139, 0.122) Experimental Example 1-2 Compound 2-5 3.86 5.36 (0.138, 0.126) Experimental Example 1-3 Compound 2-6 3.85 5.51 (0.138, 0.127) Experimental Examples 1-4 Compound 2-7 4.03 5.42 (0.137, 0.125) Experimental Examples 1-5 Compound 2-16 3.83 5.56 (0.136, 0.125) Experimental Example 1-6 Compound 2-17 4.03 5.54 (0.136, 0.127) Experimental Example 1-7 Compound 2-21 3.94 5.35 (0.136, 0.125) Experimental Examples 1-8 Compound 2-22 3.86 5.36 (0.137, 0.125) Experimental Examples 1-9 Compound 2-23 3.85 5.51 (0.138, 0.125) Experimental Example 1-10 Compound 2-24 4.00 5.42 (0.136, 0.125) Experimental Example 1-11 Compound 2-33 3.84 5.46 (0.137, 0.125) Experimental Example 1-12 Compound 2-34 3.88 5.42 (0.136, 0.125) Experimental Example 1-13 Compound 2-38 3.89 5.36 (0.138, 0.126) Experimental Example 1-14 Compound 2-39 3.81 5.34 (0.137, 0.125) Experimental Example 1-15 Compound 2-40 3.80 5.50 (0.136, 0.127) Experimental Example 1-16 Compound 2-41 4.01 5.42 (0.135, 0.127) Experimental Example 1-17 Compound 2-50 3.84 5.52 (0.138, 0.127) Experimental Example 1-18 Compound 2-51 4.05 5.58 (0.137, 0.125) Comparative Example 1-1 HT1 4.23 4.68 (0.136, 0.127) Comparative Example 1-2 HT2 4.53 4.72 (0.136, 0.127) Comparative Example 1-3 HT3 4.25 4.65 (0.135, 0.125) Comparative Example 1-4 HT4 4.47 4.89 (0.135, 0.130)

As shown in Table 1, in Experimental Examples 1-1 to 1-6 using a compound having the structure of Formula 5 as a core, Experimental Examples 1-7 to 1-6 using a compound having the structure of Formula 6 as a core, 12, and Experimental Examples 1-13 to 1-18 using a compound having the structure of Formula 7 as a core, the voltage was lower than that of the device using the compound EB1 as an electron blocking layer in Experimental Example 1, .

Comparing with the devices of Comparative Examples 1-1 to 1-4, it was found that (a) a substance having no substituent group on benzocarbazole, (c) a substance having no substituent on benzocarbazole, Was improved in terms of voltage and efficiency than other materials.

As shown in Table 1, it was confirmed that the compound of the present invention is excellent in electron blocking ability and applicable to organic light emitting devices.

< Experimental Example 2>

In the same manner as in Experimental Example 1, except that the compounds of Experimental Examples 1-1 to 1-18 were used instead of NBP as the hole transport layer, the results of the following Table 2 were obtained.

division compound
(Hole transport layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1 Compound NBP 4.41 5.03 (0.138, 0.127) Experimental Example 2-1 Compound 2-4 4.24 5.25 (0.139, 0.122) EXPERIMENTAL EXAMPLE 2-2 Compound 2-5 4.16 5.26 (0.138, 0.126) Experimental Example 2-3 Compound 2-6 4.15 5.41 (0.138, 0.127) Experimental Example 2-4 Compound 2-7 4.30 5.32 (0.137, 0.125) Experimental Example 2-5 Compound 2-16 4.13 5.46 (0.136, 0.125) Experimental Examples 2-6 Compound 2-17 4.23 5.44 (0.136, 0.127) Experimental Example 2-7 Compound 2-21 4.24 5.25 (0.136, 0.125) Experimental Examples 2-8 Compound 2-22 4.16 5.26 (0.137, 0.125) Experimental Examples 2-9 Compound 2-23 4.25 5.41 (0.138, 0.125) Experimental Example 2-10 Compound 2-24 4.00 5.32 (0.136, 0.125) Experimental Example 2-11 Compound 2-33 4.24 5.36 (0.137, 0.125) Experimental Examples 2-12 Compound 2-34 4.38 5.32 (0.136, 0.125) Experimental Example 2-13 Compound 2-38 4.29 5.26 (0.138, 0.126) Experimental Example 2-14 Compound 2-39 4.11 5.24 (0.137, 0.125) Experimental Example 2-15 Compound 2-40 4.10 5.40 (0.136, 0.127) Experimental Example 2-16 Compound 2-41 4.11 5.32 (0.135, 0.127) Experimental Example 2-17 Compound 2-50 4.14 5.42 (0.138, 0.127) Experimental Example 2-18 Compound 2-51 4.25 5.48 (0.137, 0.125) Comparative Example 2-1 HT1 4.63 4.58 (0.136, 0.127) Comparative Example 2-2 HT2 4.65 4.52 (0.136, 0.127) Comparative Example 2-3 HT3 4.55 4.45 (0.135, 0.125) Comparative Example 2-4 HT4 4.77 4.69 (0.135, 0.130)

As shown in Table 2, in Experimental Examples 2-1 to 2-6 using a compound having a structure of the formula 5 as a core, Experimental Examples 2-7 to 2-6 using a compound having the structure of the formula 6 as a core, 12, and the devices of Experimental Examples 2-13 to 2-18 in which the compound having the structure of Formula 7 was used as the core were lower in voltage and higher in efficiency than the device using the compound NBP as the hole transporting layer in Experimental Example 1 .

In comparison with the devices of Comparative Examples 2-1 to 2-4, it was found that (a) a substance having no substituent group on benzocarbazole, (c) a substance having no substituent on benzocarbazole, Was improved in terms of voltage and efficiency than other materials.

As shown in Table 2, it was confirmed that the compounds of the present invention are excellent in hole transporting ability and applicable to organic light emitting devices.

< Experimental Example 3>

The compounds 2-1, 2-2, 2-3, 2-15, 2-18, 2-19, 2-20, 2-32, 2-35, 2-36, 2-37 , 2-49 were subjected to high-purity sublimation purification by a commonly known method, and then a green organic light-emitting device was prepared in the following manner.

(60 nm) / TCTA (80 nm) / CBP + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) using CBP as a host on the prepared ITO transparent electrode. ) / LiF (1 nm) / Al (200 nm) were fabricated in this order to produce an organic EL device.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP are as follows.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that the compound 2-1 was used instead of the compound CBP in Experimental Example 3.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 2-2 was used in place of Compound CBP in Experimental Example 3.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 2-3 was used in place of Compound CBP in Experimental Example 3.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 2-15 was used in place of Compound CBP in Experimental Example 3.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that the compound 2-18 was used instead of the compound CBP in Experimental Example 3.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 2-19 was used in place of Compound CBP in Experimental Example 3.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 2-20 was used in place of Compound CBP in Experimental Example 3.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 2-32 was used in place of Compound CBP in Experimental Example 3.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 2-35 was used in place of Compound CBP in Experimental Example 3.

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that Compound 2-36 was used in place of Compound CBP in Experimental Example 3.

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that Compound 2-37 was used in place of Compound CBP in Experimental Example 3.

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that Compound 2-49 was used in place of Compound CBP in Experimental Example 3.

&Lt; Comparative Example 3-1 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 3, except that the following compound GH1 was used instead of the compound CBP in Experimental Example 3.

[GH1]

&Lt; Comparative Example 3-2 &

An organic light emitting device was prepared in the same manner as in Experimental Example 3, except that the following compound GH2 was used in place of the compound CBP in Experimental Example 3.

[GH2]

The results shown in Table 3 were obtained when current was applied to the organic light-emitting devices manufactured in Experimental Examples 3-1 to 3-12 and Comparative Examples 3-1 to 3-2.

division compound
(Host) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) EL peak
(nm) Experimental Example 3 CBP 6.75 45.18 516 Experimental Example 3-1 Compound 2-1 6.88 44.93 517 Experimental Example 3-2 Compound 2-2 6.86 45.24 516 Experimental Example 3-3 Compound 2-3 6.85 44.72 518 Experimental Example 3-4 Compound 2-15 6.89 44.65 517 Experimental Example 3-5 Compound 2-18 6.88 44.31 515 Experimental Example 3-6 Compound 2-19 6.83 44.63 516 Experimental Example 3-7 Compound 2-20 6.89 44.62 516 Experimental Examples 3-8 Compound 2-32 6.87 44.64 517 Experimental Examples 3-9 Compound 2-35 6.74 45.08 518 Experimental Example 3-10 Compound 2-36 6.96 44.72 517 Experimental Example 3-11 Compound 2-37 6.82 44.70 517 Experimental Examples 3-12 Compound 2-49 6.83 44.76 516 Comparative Example 3-1 GH1 7.28 43.69 517 Comparative Example 3-2 GH2 7.35 43.70 518

As a result of the experiment, it was confirmed that the compounds of formulas 2-1, 2-2, 2-3, 2-15, 2-18, 2-19, 2-20, 2-32, 2-35, 2-36, 2- 37 and 2-49 were used as the host material of the light emitting layer, the green organic EL devices of Experimental Examples 3-1 to 3-12 were prepared in the same manner as Experimental Example 3, Comparative Example 3-1, and Comparative Example 3 using conventional CBP -2 in terms of current efficiency and driving voltage.

< Experimental Example 4>

&Lt; Examples 1 to 21 &

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 -6 torr. Then, an organic material was injected onto the ITO using DNTPD (700 Å), α-NPB (300 Å) , 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-25, 2-26, 2-27, 2-28, 2-29, 2-30, 2 (90 wt%) was used as a host, and the following (piq) 2Ir ( Alq3 (350 Å), LiF (5 Å) and Al (1,000 Å) were deposited in this order and measured at 0.4 mA.

The DNTPD, α-NPB, (piq ) 2 Ir (acac), The structure of Alq ₃ is as follows.

&Lt; Comparative Example 4 &

The organic electroluminescent device of Comparative Example 4 was fabricated in the same manner except that CBP which is widely used as a general phosphorescent host material instead of the compound prepared by the present invention as a host of the light emitting layer in the device structure of the above example was used.

The voltage, the luminance, the current density, the color coordinates and the lifetime of the organic light-emitting device manufactured according to Examples 1 to 21 and Comparative Example 4 were measured, and the results are shown in Table 4.

The voltage, the current density, the luminance, the color coordinate, and the life span of the organic electroluminescent device manufactured according to Examples 1 to 9 and Comparative Example 1 were measured, and the results are shown in Table 4 below. T95 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.

division Host Dopant Voltage
(V) Luminance
(cd / m < 2 & CIEx
CIEy T95
(hr) Example 1 2-8 [(piq) 2Ir (acac)] 4.3 1860 0.670 0.329 465 Example 2 2-9 [(piq) 2Ir (acac)] 4.2 1850 0.674 0.325 415 Example 3 2-10 [(piq) 2Ir (acac)] 4.1 1900 0.672 0.327 440 Example 4 2-11 [(piq) 2Ir (acac)] 4.3 1840 0.673 0.335 435 Example 5 2-12 [(piq) 2Ir (acac)] 4.0 1790 0.675 0.333 405 Example 6 2-13 [(piq) 2Ir (acac)] 4.2 1810 0.670 0.339 420 Example 7 2-14 [(piq) 2Ir (acac)] 4.3 1970 0.671 0.338 445 Example 8 2-25 [(piq) 2Ir (acac)] 4.3 1860 0.668 0.329 465 Example 9 2-26 [(piq) 2Ir (acac)] 4.2 1850 0.673 0.325 415 Example 10 2-27 [(piq) 2Ir (acac)] 4.1 1900 0.670 0.327 440 Example 11 2-28 [(piq) 2Ir (acac)] 4.3 1840 0.671 0.335 435 Example 12 2-29 [(piq) 2Ir (acac)] 4.0 1790 0.674 0.333 405 Example 13 2-30 [(piq) 2Ir (acac)] 4.2 1810 0.675 0.339 420 Example 14 2-31 [(piq) 2Ir (acac)] 4.3 1970 0.671 0.338 445 Example 15 2-42 [(piq) 2Ir (acac)] 4.3 1860 0.668 0.329 465 Example 16 2-43 [(piq) 2Ir (acac)] 4.2 1850 0.674 0.325 415 Example 17 2-44 [(piq) 2Ir (acac)] 4.1 1900 0.672 0.327 440 Example 18 2-45 [(piq) 2Ir (acac)] 4.3 1840 0.669 0.335 435 Example 19 2-46 [(piq) 2Ir (acac)] 4.0 1790 0.668 0.333 405 Example 20 2-47 [(piq) 2Ir (acac)] 4.2 1810 0.669 0.339 420 Example 21 2-48 [(piq) 2Ir (acac)] 4.3 1970 0.668 0.338 445 Comparative Example 4 CBP [(piq) 2Ir (acac)] 6.9 320 0.679 0.339 60

As a result of the experiment, it was confirmed that 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-14, 2-25, 2-26, 2-27, 2-28 , 2-29, 2-30, 2-31, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48 as the host material of the light emitting layer It was confirmed that the red organic EL devices of Examples 1 to 21 used in Experimental Example 4 had better performance in terms of current efficiency, driving voltage and lifetime than the red organic EL device of Comparative Example 4 using conventional CBP.

While the present invention has been described with reference to the preferred embodiments (the electron suppression layer, the hole transport layer, the green emission layer, and the red emission layer), the present invention is not limited thereto. And it is also within the scope of the invention.

1: substrate
2: anode
3: Hole injection layer
4: hole transport layer
5: light emitting layer
6: electron transport layer
7: cathode

Claims

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
Cy1 is represented by any one of the following formulas (2) to (4)
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
* Is the connecting site,
t is an integer from 0 to 10,
u is an integer of 1 to 10,
When t is an integer of 2 or more, a plurality of L1s are the same or different from each other,
When u is an integer of 2 or more, plural Y < 1 > s are the same or different from each other,
L1 is a substituted or unsubstituted arylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted carbazolylene group; A heteroarylene group containing one or two N atoms; Or a substituted or unsubstituted heteroarylene group containing at least one of O and S atoms,
Y1 is hydrogen; heavy hydrogen; A halogen group; Cyano; -N (Z1) (Z2); A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; A substituted or unsubstituted carbazole group; A heteroaryl group containing one or two N atoms; Or a substituted or unsubstituted heteroaryl group containing at least one of O and S atoms,
Z 1 and Z 2 are the same or different and are each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazolyl group; A heteroaryl group containing one or two N atoms; Or a substituted or unsubstituted heteroaryl group containing at least one of O and S atoms,
a and c are integers of 0 to 2,
b and d are integers of 0 to 3,
e is an integer of 0 to 1,
f is an integer of 0 to 4,
When a is an integer of 2 or more, a plurality of R 5 's are the same as or different from each other,
When b is an integer of 2 or more, a plurality of R 6 are the same or different from each other,
When c is an integer of 2 or more, plural R < 7 > are the same as or different from each other,
When d is an integer of 2 or more, the plural R < 8 > s are the same as or different from each other,
When f is an integer of 2 or more, a plurality of R 10 s are the same or different from each other,
R1 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroaryl group containing at least one of N, O and S atoms, or is bonded to adjacent groups to form a ring,
X is - (A) _m - (B) _n ,
m is an integer of 0 to 10,
n is an integer of 1 to 10,
When m is an integer of 2 or more, plural A's are the same or different from each other,
When n is an integer of 2 or more, a plurality of B's are the same as or different from each other,
A is a substituted or unsubstituted arylene group; A substituted or unsubstituted alkenylene group; Or a substituted or unsubstituted heteroarylene group containing at least one of N, O and S atoms,
B is hydrogen; heavy hydrogen; A halogen group; Cyano; -N (Z3) (Z4); A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heteroaryl group containing at least one of N, O and S atoms,
Z3 and Z4 are the same or different and each independently represents a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group; A substituted or unsubstituted dinifluorenyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted carbazolyl group; Or a substituted or unsubstituted heteroaryl group containing at least one of N, O and S atoms.

The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 5:
[Chemical Formula 5]

In Formula 5,
L1, Y1, X, R1 to R6, a, b, t and u are as defined in the above formula (1).

The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 6:
[Chemical Formula 6]

In Formula 6,
R1, R4, R7, R8, c, d, t and u are as defined in the above formula (1).

The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 7:
(7)

In Formula 7,
R1, R4, R9, R10, e, f, t and u are as defined in the above formula (1).

[3] The compound according to claim 1, wherein A in Formula 1 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted divalent naphthalene group; A substituted or unsubstituted carbazolylene group; A substituted or unsubstituted divalent dibenzofurane group; A substituted or unsubstituted divalent dibenzothiophene group; A substituted or unsubstituted divalent pyridine group; A substituted or unsubstituted divalent pyrimidine group; Or a substituted or unsubstituted divalent triazine group.

The compound according to claim 1, wherein B in Formula 1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted silyl group.

The compound according to claim 1, wherein X in the formula (1) is selected from the substituents described in the following [Table 1]
[Example Chart 1]

[4] The compound according to claim 1, wherein L1 in Formula 1 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted divalent naphthalene group; A substituted or unsubstituted carbazolylene group; A substituted or unsubstituted divalent dibenzofurane group; A substituted or unsubstituted divalent dibenzothiophene group; A substituted or unsubstituted divalent pyridine group; Or a substituted or unsubstituted divalent pyrimidine group.

[4] The compound according to claim 1, wherein Y < 1 > in formula 1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted quinazoline group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted silyl group.

The compound according to claim 1, wherein - (L1) t- (Y1) u of the formula (1) is selected from the substituents described in the following [Table 2]
[Example Table 2]

The compound according to claim 1, wherein the compound of formula (1) is selected from the following formulas.

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 13, device.

The organic electronic device according to claim 14, wherein the organic compound layer including the compound is a light emitting layer.

The organic electronic device according to claim 14, wherein the organic compound layer containing the compound is an electron injecting layer, an electron transporting layer, or an electron injecting and transporting layer.

15. The organic electronic device according to claim 14, wherein the organic compound layer containing the compound is a hole injection layer, a hole transport layer, or a hole injection and transport layer.

15. The organic electronic device according to claim 14, wherein the compound is a phosphorescent host material or a fluorescent host material.

15. The organic electronic device according to claim 14, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC) and an organic transistor.