KR101698640B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

Description

HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

The present invention relates to heterocyclic compounds and organic light emitting devices containing them.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows.

When an organic layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

Therefore, there is a need in the art to develop new organic materials.

Tang, C. W .; VanSlyke, S. A .; Chen, C. H., Electroluminescence of doped organic thin films, Journal of Applied Physics (1989), 65 (9), 3610-16.

It is an object of the present invention to provide a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

In one embodiment of the present specification, there is provided a heterocyclic compound represented by the following general formula (1).

[Chemical Formula 1]

In formula (1)

a and d are each an integer of 1 to 4,

b is an integer of 1 to 7,

c is an integer of 1 to 6,

X is O, S, NR, or CRR '

R1 and R2 are each hydrogen or combine to form a 5-membered condensed ring,

when a is an integer of 2 to 4, a plurality of R 3 are the same as or different from each other,

When b is an integer of 2 to 7, a plurality of R4s may be the same or different from each other,

When c is an integer of 2 to 6, a plurality of R 5 s may be the same as or different from each other,

When d is an integer of 2 to 4, a plurality of R 6 are the same or different from each other,

R and R 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group,

R3 to R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group, or two or more groups adjacent to each other may be connected to each other to form a ring.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises the heterocyclic compound do.

Heterocyclic compounds according to embodiments of the present disclosure have suitable energy levels and are excellent in electrochemical stability and thermal stability. Thus, the organic light emitting device comprising the compound provides high efficiency and / or high driving stability.

1 to 5 are cross-sectional views illustrating the structure of an organic light emitting device according to an embodiment of the present invention.
6 is a graph showing a mass spectrum of the formula 1-a-1.
7 is a diagram showing a mass spectrum of the formula 1-a-2.
8 is a diagram showing the mass spectrum of the intermediate 2-5.

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

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is provided.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by Formula 2 or Formula 3 below.

(2)

(3)

In the general formulas (2) and (3)

X, a, b, c, d, R, R ', R 1, R 2 and R 3 to R 6 are as defined above.

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

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by Formula 4 or Formula 5 below.

[Chemical Formula 4]

[Chemical Formula 5]

In the general formulas (4) and (5)

X, a, b, d, R, R ', R1, R2 and R3 to R6 are the same as defined above.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 4 is represented by the following Formula 4-1.

[Formula 4-1]

In one embodiment of the present invention, the heterocyclic compound represented by Formula 5 is represented by the following Formula 5-1.

[Formula 5-1]

In the general formulas (4-1) and (5-1)

X, a, b, d, R, R ', R1, R2 and R3 to R6 are the same as defined above.

In one embodiment of the present disclosure, X is S or O.

In one embodiment of the present disclosure, X is S.

In one embodiment of the present disclosure, X is O.

In one embodiment of the present disclosure, R5 is selected from the group consisting of hydrogen; A nitrile group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aliphatic or aromatic heterocyclic group; A substituted or unsubstituted arylamine group.

In one embodiment of the present specification, R5 is a substituted or unsubstituted carbazole group.

In one embodiment of the present disclosure, R5 is selected from the group consisting of hydrogen; Or one of the following substituents.

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

및

And

In the substituent,

e is an integer of 1 to 4,

f and g are each an integer of 1 to 7,

h is an integer of 1 to 9,

i is an integer of 1 to 8,

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent aromatic or aliphatic heterocyclic group containing at least one of N, O and S atoms,

R10 to R25 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 heteroarylamine group; A substituted or unsubstituted imine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group.

In one embodiment of the present disclosure, L1 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted divalent carbazole group.

Examples of such substituents are described below, but are not limited thereto.

또는

는 다른 치환기에 연결되는 부위를 의미한다. In this specification

or

Quot; refers to a moiety that is connected to another substituent.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; A hydroxy group; Thiol group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryl group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; Arylalkyl groups; An arylalkenyl group; And an aromatic or aliphatic heterocyclic group, or that at least two of the substituents exemplified above are substituted or unsubstituted with a substituent to which they are linked. 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, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be mono- or di-substituted by nitrogen of the amide group with hydrogen, a straight-chain, branched-chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, N-octyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

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. 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 aryl group may be a monocyclic aryl group or a polycyclic aryl group, and includes a case where an alkyl group having 1 to 25 carbon atoms or an alkoxy group having 1 to 25 carbon atoms is substituted. In addition, an aryl group in the present specification may mean an aromatic ring.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and a stilbenyl group.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

In the present specification, a fluorenyl group is a structure in which two cyclic organic compounds are connected through one atom.

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

,

,

, 및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

, And

And the like. However, the present invention is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, the heterocyclic group is an aliphatic or aromatic heterocyclic group containing at least one of O, N and S as a hetero atom. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. 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, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl groups in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group are the same as the aforementioned aryl groups. Specific examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, Naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Phenanthryloxy, 9-phenanthryloxy and the like. Examples of the arylthioxy group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenyl And the like. Examples of the aryl sulfoxy group include a benzene sulfoxy group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present specification, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.

In the present specification, the alkyl group in the alkylthio group and the alkylsulfoxy group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyloxy group, an ethylsulfoxy group, a propylsulfoxy group, But the present invention is not limited thereto.

In the present specification, an arylene group means a group having two bonding positions in an aryl group, that is, a divalent group. The description of the aryl group described above can be applied except that each of these is 2 groups.

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 ring, aromatic ring, aliphatic heterocyclic ring and aromatic heterocyclic ring may be monocyclic or polycyclic.

In one embodiment of the present disclosure, R1 and R2 are each hydrogen.

In one embodiment of the present specification, R 1 and R 2 combine with each other to form a 5-membered condensed ring.

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

In one embodiment of the present disclosure, R4 is 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 invention, the heterocyclic compound represented by the general formula (1) is represented by the general formula (5).

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-a-1 to 1-a-6.

In the above formulas (1-a-5) and (1-a-6), the definition of R is the same as described above.

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

to be.

이고, R10 및 R11은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다. In one embodiment of the present disclosure, R5 is

, R10 and R11 are the same or different and are each independently a substituted or unsubstituted aryl group.

이고, R10 및 R11은 페닐기이다. In one embodiment of the present disclosure, R5 is

And R10 and R11 are phenyl groups.

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

to be.

이고, R10 및 R11은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다. In one embodiment of the present disclosure, R5 is

, R10 and R11 are the same or different and are each independently a substituted or unsubstituted aryl group.

이고, R10 및 R11은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이며, R12는 수소이다. In one embodiment of the present disclosure, R5 is

, R10 and R11 are the same or different and are each independently a substituted or unsubstituted aryl group, and R12 is hydrogen.

이고, R10 및 R11은 페닐기이며, R12는 수소이다. In one embodiment of the present disclosure, R5 is

, R10 and R11 are phenyl groups, and R12 is hydrogen.

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

to be.

이고, R10 및 R12는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다. In one embodiment of the present disclosure, R5 is

, R10 and R12 are the same or different and are each independently a substituted or unsubstituted aryl group.

이고, R10 및 R12는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이고, R11 및 R13은 수소이다. In one embodiment of the present disclosure, R5 is

, R10 and R12 are the same or different and are each independently a substituted or unsubstituted aryl group, and R11 and R13 are hydrogen.

이고, R10 및 R12는 페닐기이고, R11 및 R13은 수소이다. In one embodiment of the present disclosure, R5 is

, R10 and R12 are phenyl groups, and R11 and R13 are hydrogen.

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

to be.

이고, R14는 치환 또는 비치환된 알킬기이다. In one embodiment of the present disclosure, R5 is

And R14 is a substituted or unsubstituted alkyl group.

이고, R14는 치환 또는 비치환된 알킬기이고, R15는 수소이다. In one embodiment of the present disclosure, R5 is

, R14 is a substituted or unsubstituted alkyl group, and R15 is hydrogen.

이고, R14는 메틸기이다. In one embodiment of the present disclosure, R5 is

And R14 is a methyl group.

이고, R14는 치환 또는 비치환된 아릴기이다. In one embodiment of the present disclosure, R5 is

And R14 is a substituted or unsubstituted aryl group.

이고, R14는 치환 또는 비치환된 아릴기이고, R15는 수소이다. In one embodiment of the present disclosure, R5 is

, R14 is a substituted or unsubstituted aryl group, and R15 is hydrogen.

이고, R14는 페닐기이다. In one embodiment of the present disclosure, R5 is

And R14 is a phenyl group.

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

to be.

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

to be.

이고, R16은 수소이다. In one embodiment of the present disclosure, R5 is

And R16 is hydrogen.

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

to be.

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

to be.

이고, R23은 수소이다. In one embodiment of the present disclosure, R5 is

And R23 is hydrogen.

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

to be.

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

to be.

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

to be.

이고, R24 및 R25는 수소이다. In one embodiment of the present disclosure, R5 is

And R24 and R25 are hydrogen.

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

to be.

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

to be.

In one embodiment of the present disclosure, L1 is a direct bond.

In one embodiment of the present specification, R6 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group.

In another embodiment, R6 is a substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, R6 is a substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted pyridine group, and when they are substituted, the substituent may be any one selected from the group consisting of a substituted or unsubstituted alkyl group and a substituted or unsubstituted aryl group. More specifically, the substituent may be selected from a methyl group or a phenyl group.

In one embodiment of the present specification, R6 may be a heterocyclic group containing at least one N atom as a hetero atom.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-b-1 to 1-b-44.

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

to be.

이고, R14는 치환 또는 비치환된 아릴기이다. In one embodiment of the present disclosure, R5 is

And R14 is a substituted or unsubstituted aryl group.

이고, R14는 치환 또는 비치환된 아릴기이며, R15는 수소이다. In one embodiment of the present disclosure, R5 is

, R14 is a substituted or unsubstituted aryl group, and R15 is hydrogen.

이고, R14는 페닐기이다. In one embodiment of the present disclosure, R5 is

And R14 is a phenyl group.

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

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

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

to be.

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

to be.

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

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

이다. In one embodiment of the present specification, L1 is a divalent carbazole group, and specifically

to be.

이다. In one embodiment of the present specification, L1 is a divalent carbazole group, and specifically

to be.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-c-1 to 1-c-48.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of Formulas 1-d-1 to 1-d-34.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-e-1 to 1-e-48.

이다, In one embodiment of the present disclosure, R5 is

to be,

In one embodiment of the present specification, R17 and R18 are the same or different and are each independently a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R17 and R18 are the same or different and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, Lt; / RTI >

In one embodiment of the present specification, R17 and R18 are biphenyl groups.

In one embodiment of the present specification, R17 and R18 are the same as or different from each other, and each independently is a phenyl group or a biphenyl group.

In one embodiment of the present specification, R17 and R18 are the same as or different from each other, and each independently is a phenyl group or a terphenyl group.

In one embodiment of the present specification, R17 and R18 are the same or different from each other and each independently a fluorenyl group substituted with a biphenyl group or an alkyl group.

이다. In one embodiment of the present specification, the biphenyl group is

to be.

이다. In one embodiment of the present specification, the biphenyl group is

to be.

이다. In one embodiment of the present specification, the biphenyl group is

to be.

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

to be.

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

to be.

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

to be.

In one embodiment of the present specification, R19 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R19 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R19 is a phenyl group.

In one embodiment of the present disclosure, R20 is hydrogen.

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

to be.

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

In one embodiment of the present specification, R22 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R22 is a phenyl group.

In one embodiment of the present specification, R22 is substituted at positions 3 and 6 of the carbazole group, respectively.

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

to be.

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

In one embodiment of the present invention, R21 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R21 is a methyl group.

In one embodiment of the present specification, R21 is substituted at position 9.

In one embodiment of the present disclosure, L1 is a direct bond.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-f-1 to 1-f-44.

In one embodiment of the present disclosure, X is NR.

In one embodiment of the present disclosure, X is NR and R is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. In one embodiment of the present specification, X is NR, R is a substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another embodiment, X is NR, R is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted triazine group; A substituted or unsubstituted pyrimidine group; Or a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, X is NR and R is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, X is NR and R is a phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group and a cyano group.

In one embodiment of the present specification, X is NR, R is a substituted or unsubstituted triazine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted pyridine group, and a substituted or unsubstituted cyano group.

In one embodiment of the present specification, X is NR and R is a substituted or unsubstituted heterocyclic group containing at least one N atom as a hetero atom.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-g-1 to 1-g-39.

In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulas 1-h-1 to 1-h-54.

Among the compounds represented by the above formula (1), when X is O or S and R 1 and R 2 are bonded to form a 5-membered condensed ring, the compound can be prepared on the basis of the following production example. For example, it can be prepared as shown in Reaction Scheme 1 below.

[Reaction Scheme 1]

In the compounds represented by the above formula (1), when X is O or S, and R 1 and R 2 are each hydrogen, the compound can be produced based on the following production example. For example, it can be prepared as shown in Reaction Scheme 2 below.

[Reaction Scheme 2]

In the above Reaction Scheme 1 and Reaction Scheme 2, R3 to R6, R17, R18 and X are the same as described above.

The heterocyclic compound represented by the formula (1) can be prepared by condensing a brominated carbazole group or a brominated triphenylamine group after producing A as in the above-mentioned production method.

1-a-4, 1-b-1 to 1-b-42, 1-c-1 to 1-b-1, the heterocyclic compound represented by the formula (1) as well as c-48, 1-d-1 to 1-d-34, 1-e-1 to 1-e-48 and 1-f- Can be prepared.

Among the compounds represented by the above formula (1), when X is NR and R 1 and R 2 are bonded to form a 5-membered condensed ring, the compound can be produced based on the following production example. For example, it can be prepared as shown in Reaction Scheme 3 below.

[Reaction Scheme 3]

In the compounds represented by the above formula (1), when X is NR and R 1 and R 2 are each hydrogen, the compound can be prepared on the basis of the following production example. For example, it can be prepared as shown in Reaction Scheme 4 below.

[Reaction Scheme 4]

The present invention also provides an organic light emitting device comprising the heterocyclic compound represented by Formula 1.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting 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, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, And the above heterocyclic compound.

In one embodiment of the present invention, the light emitting layer includes the heterocyclic compound.

In one embodiment of the present invention, the light emitting layer includes the heterocyclic compound as a host.

In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously transporting holes and injecting holes, wherein the hole injecting layer, the hole transporting layer, And the above heterocyclic compound.

In the present specification, R 3 to R 6 may be selected and used as a hole transport material, a host material in an emission layer, or an electron transport material depending on the nature of the substituent represented by the general formula (1).

In one embodiment of the present invention, the organic material layer may further include a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group or a benzocarbazole group, in addition to the organic compound layer containing the heterocyclic compound.

In one embodiment of the present invention, the organic compound layer containing the heterocyclic compound includes the heterocyclic compound as a host, and may include another organic compound, metal or metal compound as a dopant.

In one embodiment of the present invention, the organic compound layer containing the heterocyclic compound includes the heterocyclic compound as a host of the green light emitting layer, and may include another organic compound, metal or metal compound as a dopant.

In one embodiment of the present invention, the organic light emitting device may further include an organic material layer including a compound that is not a heterocyclic compound represented by Formula 1. In this case, the kind of the organic material layer is the same as described above.

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

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

For example, the structure of the organic light emitting device according to the present invention is illustrated in FIGS.

1 shows an organic light emitting device in which 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 on a substrate 1 Structure is illustrated. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, the light emitting layer 5, or the electron transporting layer 6.

2 illustrates a structure of an organic light emitting device in which an anode 2, a hole injecting layer 3, a hole transporting layer 4, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole injecting layer 3, the hole transporting layer 4, or the electron transporting layer 6.

3 illustrates a structure of an organic light emitting device in which an anode 2, a hole transporting layer 4, a light emitting layer 5, an electron transporting layer 6, and a cathode 7 are sequentially laminated on a substrate 1. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 4, the light emitting layer 5, or the electron transport layer 6.

4 shows a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, an electron transport layer 6 and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light-emitting layer 5 or the electron-transporting layer 6.

5 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, and a cathode 7 are sequentially laminated on a substrate 1. [ In such a structure, the compound represented by Formula 1 may be included in the light emitting layer 5.

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

The organic light-emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the heterocyclic compound.

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a 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 light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode 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 light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic light emitting 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 heterocyclic compound may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The heterocyclic compound represented by Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

Manufacturing example

Reaction Example 1) Preparation of intermediate 1-5

Preparation of compounds 1-3

(0.17 mol) of dibenzo [b, d] thiophen-4-ylboronic acid, 1-1) and methyl 2-bromobenzoate (methyl 2 (0.16 mol) was dissolved in 450 mL of tetrahydrofuran (THF), and 110 mL of an aqueous solution obtained by dissolving 70 g (0.51 mol) of potassium carbonate (K ₂ CO ₃ ) was added and warmed. 1.9 g (1.6 mmol) of tetrakis (triphenylphosphine) palladium (0) was added thereto under reflux, followed by stirring under reflux for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, washed with water and extracted with ethyl acetate. The combined organic extracts were washed with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. 50 g of the objective compound 1-3 in the form of oil were obtained.

Preparation of compounds 1-4

50 g (0.16 mol) of Compound 1-3 was diluted in a mixed solvent of 150 mL of methanol and 40 mL of tetrahydrofuran (THF), and then 70 mL (0.32 mol) of 4N sodium hydroxide (NaOH) aqueous solution was added. The mixture was heated and refluxed for about 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature to remove the organic layer, and the remaining aqueous layer was washed with a methyl tertiary butyl ether (MTBE) solvent to remove the organic layer and acidified by addition of 1N hydrochloric acid (HCl) aqueous solution. Ethyl acetate was added to the acidified aqueous solution to extract the compound. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated. Hexane was added to the solid obtained by concentration, and the mixture was stirred to obtain 35 g (67%) of the target compound 1-4 as a white solid.

Preparation of compounds 1-5

14.3 g (4.7 mmol) of Compound 1-4 was diluted in 150 mL of acetic acid, followed by addition of 30 mL of concentrated sulfuric acid, and the mixture was stirred under reflux for about 12 hours. After completion of the reaction, the mixture was cooled to room temperature, and the resulting solid was filtered. The filtered solid was dissolved in chloroform and neutralized with 1N aqueous sodium hydroxide solution. The organic layer was separated, washed again with water, treated with anhydrous magnesium sulfate, Lt; / RTI > Hexane and ethanol were added to the concentrated compound, which was then heated to 50 DEG C, stirred for 1 hour, cooled to room temperature and filtered. Yellow solid compound 1-5 (6.4 g, 48%) was obtained.

MS: [M + H] < ⁺ > = 287

Reaction Example 2) Preparation of intermediate 2-5

Preparation of Compound 2-3

(0.22 mol) of dibenzo [b, d] thiophen-4-ylboronic acid, 1-1) and methyl 2-bromo-5-chlorobenzo 125 mL of an aqueous solution obtained by dissolving 50 g (0.20 mol) of methyl 2-bromo-5-chlorobenzoate, 2-2 in 500 mL of tetrahydrofuran (THF) and then dissolving 83 g (0.60 mol) of potassium carbonate (K ₂ CO ₃ ) Respectively. 2.3 g (0.002 mol) of tetrakis (triphenylphosphine) palladium (0) was added thereto under reflux, followed by stirring under reflux for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, washed with water and extracted with ethyl acetate. The combined organic extracts were washed with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. 100 mL of ethanol was added to the concentrated material and solidified by stirring at room temperature, followed by filtration to obtain 57 g (80%) of the object compound 2-3 as a light brown compound.

Preparation of compound 2-4

57 g (0.16 mol) of Compound 2-3 was diluted in a mixed solvent of 180 mL of methanol and 50 mL of tetrahydrofuran (THF), and then 70 mL (0.32 mol) of 4N sodium hydroxide (NaOH) solution was added. The mixture was heated and refluxed for about 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature to remove the organic layer, and the remaining aqueous layer was washed with diethyl ether to remove the organic layer and acidified by addition of 1N hydrochloric acid (HCl) aqueous solution. Ethyl acetate was added to the acidified aqueous solution to extract the compound. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated. Hexane was added to the solid obtained by concentration, and the mixture was stirred to obtain 47 g (86%) of the target compound 2-4 as a white solid.

Preparation of Compound 2-5

45 g (0.13 mol) of the compound 2-4 was diluted in 45 mL of chloroform, 24 mL (0.26 mol) of trifluoromethanesulfonic acid was added, and the mixture was heated to 80 DEG C and stirred. After confirming the completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting solid was filtered and washed with water. The residue was dissolved in chloroform and neutralized with an aqueous solution of sodium hydrogencarbonate, and then the organic layer was treated with anhydrous magnesium sulfate, followed by filtration and concentration. Hexane was added to the concentrated material and stirred, followed by filtration to obtain 36 g (86%) of the objective compound 2-5.

MS: [M + H] < ⁺ > = 321

Reaction Example 3) Preparation of intermediate 3-4

Preparation of Compound 3-2

(0.23 mol) of dibenzo [b, d] furan-4-ylboronic acid, 3-1) and methyl 2-bromo-5-chlorobenzoate 150 mL of an aqueous solution obtained by dissolving 93 g (0.66 mol) of potassium carbonate (K ₂ CO ₃ ) in 600 mL of tetrahydrofuran (THF) was dissolved in 50 g (0.20 mol) of methyl 2-bromo-5-chlorobenzoate Respectively. 2.6 g (0.002 mol) of tetrakis (triphenylphosphine) palladium (0) was added thereto under reflux, followed by stirring under reflux for 12 hours. After completion of the reaction, the reaction was conducted in the same manner as in the synthesis of Compound 2-3 of Reaction Example 2 to obtain 53.2 g (78%) of a brown solid compound 3-2.

Preparation of compound 3-3

43 g (84%) of a white solid compound 3-3 was obtained from 53 g (0.16 mol) of the compound 3-2 as a starting material in the same manner as the compound 2-4 of the reaction example 2.

Preparation of compound 3-4

In the same manner as in the preparation of the compound 2-5 of Reaction Example 2, 43 g (0.13 mol) of the compound 3-3 was used as a starting material instead of the compound 2-4 to obtain 35 g (86%) of the objective compound 3-4 as yellow.

MS: [M + H] < ⁺ > = 305

Reaction Example 4) Preparation of intermediate 4-4

Preparation of Compound 4-2

Dibenzo [b, d] thiophen-4-ylboronic acid, 1-1) in the same manner as in the preparation of the compound 2-3 of the Reaction Example 2, (70%) of the object compound 4-2 as a starting material was obtained as a starting material, and 50 g (0.20 mol) of methyl 2-bromo-4-chlorobenzoate, ).

Preparation of compound 4-3

In the same manner as in the preparation of the compound 2-4 of the Reaction Example 2, 55 g (0.16 mol) of the compound 4-2 was used as a starting material instead of the compound 2-3 to obtain 49 g (93%) of the objective compound 4-3 as white.

Preparation of compound 4-4

In the same manner as in the preparation of the compound 2-5 of Reaction Example 2, 49 g (0.14 mol) of the compound 4-3 was used as a starting material instead of the compound 2-4, and then a small amount of chloroform and excess amount of hexane And the mixture is stirred under heating. The resulting compound was cooled to room temperature and filtered to obtain 36 g (79%) of the objective compound 4-4 as yellow.

MS: [M + H] < ⁺ > = 321

Reaction Example 5) Preparation of Compound 1-a-1

Preparation of Compound 1-7

7.4 g (21 mmol) of 2-bromo-N, N-diphenylaniline, 1-6 was dissolved in 50 mL of anhydrous tetrahydrofuran and then cooled to -78 ° C. 9.2 mL (21 mmol) of n-butyllithium (2.5 M) was slowly added to the cooled solution and stirred at the same temperature for 30 minutes. 5 g (19 mmol) of the compound of Intermediate 1-5 was added to the cooled mixture. When the reaction was completed, the mixture was warmed to room temperature, and a saturated aqueous ammonium chloride solution was added and stirred. The mixture was extracted with ethyl acetate, which was treated with anhydrous magnesium sulfate, filtered and concentrated. An excess amount of hexane and a small amount of ethyl acetate were added to the concentrated compound, followed by stirring and filtration to obtain 8.1 g (71%) of the desired compound as a pale yellow.

Preparation of compound 1-a-1

8.1 g (15 mmol) of the compound 1-7 was diluted with 50 mL of acetic acid, 0.1 mL of concentrated sulfuric acid was added, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, the solid was filtered, washed with ethanol and water in turn. The filtered solid was dissolved in chloroform and neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was separated, washed with water and separated, treated with anhydrous magnesium sulfate, filtered, and purified by recrystallization with addition of ethyl acetate. The purified solid was filtered to obtain 6.2 g (80%) of the target compound 1-a-1 as white.

MS: [M + H] < ⁺ > = 514

Reaction Example 6) Preparation of compound 1-a-2

Preparation of Compound 1-9

9.4 g (29 mmol) of 9- (2-bromophenyl) -9H-carbazole (9- (2-bromophenyl) -9H-carbazole, 1-8) was dissolved in 80 mL of anhydrous tetrahydrofuran, . 13 mL (32 mmol) of n-butyllithium (2.5 M) was slowly added to the cooled solution, followed by stirring at the same temperature for 30 minutes. 6.7 g (23 mmol) of the compound of Intermediate 1-5 was added to the cooled mixture. When the reaction was completed, the mixture was warmed to room temperature, and a saturated aqueous ammonium chloride solution was added thereto and stirred. The mixture was extracted with ethyl acetate, treated with anhydrous magnesium sulfate, filtered and concentrated. Excess hexane and a small amount of ethyl acetate were added to the concentrated compound, which was stirred and filtered to obtain 10.6 g (69%) of the desired yellow compound.

Preparation of compound 1-a-2

10.6 g (20 mmol) of the compound 1-9 was diluted in 200 mL of acetic acid, 0.1 mL of concentrated sulfuric acid was added, and the mixture was stirred under reflux for about 3 hours. After completion of the reaction, the mixture was cooled to room temperature, the solid was filtered, washed with ethanol and water in turn. The filtered solid was dissolved in 900 mL of chloroform and neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was separated, washed with water and separated, treated with anhydrous magnesium sulfate, filtered, and purified by recrystallization with addition of ethyl acetate. The purified solid was filtered to obtain 6.3 g (61%) of the desired compound 1-a-2 as white.

MS: [M + H] < ⁺ > = 512

Reaction Example 7) Synthesis of Compound 2-7

Preparation of Compound 2-6

9.4 g (0.03 mol) of 9- (2-bromophenyl) 9H-carbazole (1-8) was dissolved in 80 mL of anhydrous tetrahydrofuran, Respectively. To the cooled solution was slowly added 13 mL (13.2 mmol) of normal-butyllithium (2.5 M) solution and stirred at the same temperature for 30 minutes. 7.5 g (23.4 mmol) of the intermediate 2-5 compound was added to the cooled mixture. When the reaction was completed, a saturated ammonium chloride aqueous solution was added to the mixture and the temperature was raised to room temperature while stirring. The mixture was extracted with ethyl acetate, treated with anhydrous magnesium sulfate, filtered and concentrated. Hexane and ethyl acetate were added to the concentrated compound, which was then warmed, stirred, and filtered to obtain 10.6 g (62%) of the desired compound 2-6 as yellow.

Preparation of compound 2-7

Intermediate 2-6 The compound (10.6 g, 18.8 mmol) was diluted in 190 mL of acetic acid, followed by the addition of 0.1 mL of concentrated sulfuric acid, and the mixture was heated to 80 DEG C and stirred. After completion of the reaction, the reaction mixture was cooled to room temperature and the solid was filtered. The precipitated solid was dissolved in 900 mL of chloroform and neutralized with an aqueous solution of sodium hydrogencarbonate. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered and then purified by recrystallization. This was filtered to obtain 6.3 g (61%) of a white solid compound 2-7.

MS: [M + H] < ⁺ > = 546

The following compounds were synthesized as shown in Table 1 according to the production method of Compound 2-7 of Reaction Example 7.

Example Starting material 1 Starting material 2 product yield Reaction Example 8 Compound 2-5 Compound 1-6

75% Reaction Example 9 Compound 3-4 Compound 1-6

72% Reaction Example 10 Compound 3-4 Compound 1-8

70% Reaction Example 11 Compound 4-4 Compound 1-6

75% Reaction Example 12 Compound 4-4 Compound 1-8

73%

Reaction Example 13) Synthesis of Compound 1-b-1

Synthesis of Compound 2-9

delete

12 g (22 mmol) of intermediate 2-7 and 4,4,4 ', 4', 5,5,5 ' -octamethyl-2,2' -bis (1,3,2-dioxaborolane) 6.7 g (26.4 mmol) of 4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) After diluting with 75 ml of dioxane (1,4-dioxane), 6.5 g (66 mmol) of potassium acetate was added, and the mixture was warmed and refluxed and stirred. 370 mg (1.32 mmol) of tricyclohexylphosphine and 380 mg (0.66 mmol) of bis (dibenzylideneacetone) palladium (0) dioxane), and the mixture was added to the refluxed mixture. When the reaction was completed, the reaction mixture was cooled to room temperature, washed with water and extracted with ethyl acetate. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered and concentrated. Ethyl acetate and ethanol were added to the concentrated compound, stirred at room temperature, and filtered to obtain 11.2 g (81%) of a white solid compound 2-9.

Synthesis of Compound 1-b-1

11.2 g (18 mmol) of the compound 2-9 and the compound 2-10 2-bromo-4,6-diphenyl-1,3, 7- (15 mmol) of potassium carbonate (K ₂ CO ₃ ) was dissolved in 60 mL of tetrahydrofuran (THF), and the mixture was heated to reflux. Tetrakis After the completion of the reaction, the reaction mixture was cooled to room temperature, washed with water, and extracted with ethyl acetate. The combined organic extracts were washed with anhydrous magnesium sulfate (100 ml) and dried over anhydrous magnesium sulfate The residue was purified by recrystallization from tetrahydrofuran and ethanol and filtered to obtain 8.9 g (74%) of the target compound 1-b-1 as a white substance.

MS: [M + H] < ⁺ > = 743

The following compounds were synthesized as shown in Table 2 according to the production method of Compound 1-b-1 of Reaction Example 13.

Example Starting material 1 Starting material 2 product yield Reaction Example 14 Compound 2-9

1-b-5 75% Reaction Example 15 Compound 2-9

1-b-9 73% Reaction Example 16 Compound 2-9

1-b-13 73% Reaction Example 17 Compound 2-9

1-b-17 69% Reaction Example 18 Compound 2-9

1-b-21 72% Reaction Example 19 Compound 2-9

1-b-29 79% Reaction Example 20 Compound 2-9

1-f-25 82% Reaction Example 21 Compound 2-9

1-b-44 80%

The starting material 2 of Reaction Examples 13 to 21 may be introduced into the product synthesized in Reaction Examples 8 to 12 described above in the same manner as in Reaction Example 13 to prepare a compound.

Reaction Example 22 Synthesis of Compound 1-f-1

Preparation of compound 1-f-1

(14.6 mmol) of the compound 2-7 prepared in Reaction Example 7 and di ([1,1'-biphenyl] -4-yl) amine ) Was dissolved in 50 mL of xylene, 4.2 g (43.8 mmol) of tert -butoxide was added, and the mixture was heated to reflux and stirred. Bis (tritiated-butylphosphine) palladium (0.1 g, 0.2 mmol) was added to the mixture under reflux and stirred for 4 hours. When the reaction was completed, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The residue was dissolved in chloroform, washed with water, and then dried over anhydrous magnesium sulfate. This was recrystallized from a mixture of chloroform and ethyl acetate to obtain 8.7 g (72%) of pale yellow compound 1-f-1.

MS: [M + H] < ⁺ > = 831

The following compounds were synthesized as shown in Table 3 according to the production method of Compound 1-f-1 of Reaction Example 22.

Example Starting material 1 Starting material 2 product yield Reaction Example 23 Compound 2-8

1-f-13 73% Reaction Example 24 Compound 2-8

1-f-42 75%

The starting material 2 of Reaction Examples 22 to 24 can be introduced into the product synthesized in Reaction Examples 8 to 12 described above in the same manner as in Reaction Example 22 to prepare a compound.

6 is a graph showing a mass spectrum of the formula 1-a-1.

7 is a diagram showing a mass spectrum of the formula 1-a-2.

8 is a diagram showing the mass spectrum of the intermediate 2-5.

Reaction Example 25) Preparation of intermediate 3-4

Method for producing compound 3-3

9.4 g (29 mmol) of 9- (2-bromophenyl) -9H-carbazole (3-1) was dissolved in 80 mL of anhydrous tetrahydrofuran, Respectively. 13 mL (32 mmol) of n-butyllithium (2.5 M) was slowly added to the cooled solution, followed by stirring at the same temperature for 30 minutes. To the cooled mixture was added 7.5 g (29 mmol, 3-2) of 4-bromo-9H-fluoren-9-one. When the reaction was completed, the mixture was warmed to room temperature, and a saturated aqueous ammonium chloride solution was added thereto and stirred. The mixture was extracted with ethyl acetate, treated with anhydrous magnesium sulfate, filtered and concentrated. Excess hexane and a small amount of ethyl acetate were added to the concentrated compound, which was stirred and filtered to obtain 10.6 g (72%) of the target compound 3-3 as white.

Preparation method of intermediate 3-4

10.6 g (21 mmol) of the compound 3-3 was diluted with 200 mL of acetic acid, 0.1 mL of concentrated sulfuric acid was added, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, the solid was filtered, washed with ethanol and water in turn. The filtered solid was dissolved in 900 mL of chloroform and neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was separated, washed with water and separated, treated with anhydrous magnesium sulfate, filtered, and then purified by recrystallization. The purified solid was filtered to obtain 7.5 g (74%) of the target compound 3-4 as white.

MS: [M + H] < ⁺ > = 484

Reaction Example 26) Synthesis of Compound 1-g-34

Method for producing compound 3-5

10 g (20 mmol) of the compound of Intermediate 3-4 and 2.8 g (22 mmol) of 2-chloroaniline are added to 100 ml of toluene, and then 5.8 g (60 mmol) of NaOt-Bu is added and warmed. To the mixture at reflux was added bis (tritiated-butylphosphine) palladium (0.1 g, 0.2 mmol) and stirred for 4 hours. When the reaction was completed, the mixture was cooled to room temperature and washed twice with 100 mL of water. The mixture was extracted with ethyl acetate (100 mL), and the organic layer was separated. Anhydrous magnesium sulfate was added thereto, followed by stirring and filtration. The filtered filtrate was concentrated under reduced pressure and recrystallized with a small amount of ethyl acetate and an excess of hexane to obtain 8.8 g (83%) of a brown compound 3-5.

Method for producing compound 3-6

15 g (28 mmol) of the compound 3-5 and 1.0 g (2 mmol) of tricyclohexylphosphine tetrafluoroborate were added to 150 ml of dimethylacetamide, and while stirring, 15.4 g (112 mmol) of potassium carbonate and 310 mg 1 mmol) was added and refluxed for 6 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, washed twice with 300 mL of water, extracted with 150 mL of dichloromethane, and the organic layer was separated. The separated organic layer was treated with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and recrystallized by adding ethyl acetate while a small amount of toluene remained. This was filtered to give 11 g (80%) of light yellow compound 3-6.

Synthesis of Compound 1-g-34

10 g (20 mmol) of the compound 3-6 and 5.4 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (21 mmol) were added to 100 mL of toluene, 5.8 g (60 mmol) of NaOt-Bu was added, and the mixture was warmed. Bis (tritiated-butylphosphine) palladium (0.1 g, 0.2 mmol) was added to the mixture under reflux and stirred for 4 hours. When the reaction was completed, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The residue was dissolved in 500 ml of chloroform, washed with 200 ml of water, and then dried over anhydrous magnesium sulfate, followed by filtration. This was recrystallized from a mixture of chloroform and ethyl acetate to obtain 10.8 g (75%) of a white compound 1-g-34.

MS: [M + H] < ⁺ > = 726

Reaction Example 27) Preparation of intermediate 3-4a

Bromo-9H-fluoren-9-one, compound 3-2) instead of the compound 4-bromo-9H-fluoren-9-one in the same manner as in the preparation of Intermediate 3-4 in Reaction Example 25 9-one (3-bromo-9H-fluoren-9-one, compound 3-2a) as starting materials, 8.0 g of white objective compound intermediate 3-4a was obtained.

Reaction Example 28 Synthesis of Compound 1-h-20

Method for producing compound 4-1

12 g (22 mmol) of the compound of Intermediate 3-4a and 4,4,4 ', 4', 5,5,5'5'-octamethyl-2,2' -bis (1,3,2-dioxaborolane 6.7 g (26.4 mmol) of 4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) After diluting with 75 ml of 1,4-dioxane, 6.5 g (66 mmol) of potassium acetate was added, and the mixture was warmed and refluxed with stirring. 370 mg (1.32 mmol) of tricyclohexylphosphine and 1.25 mmol of bis (dibenzylideneacetone) palladium 380 mg (0.66 mmol) of Bis (dibenzylideneacetone) palladium (0) was dissolved in 5 mL of 1,4-dioxane, and the mixture was added to the refluxed mixture. The organic layer was separated, treated with anhydrous magnesium sulfate, and then concentrated by filtration. To the concentrated compound was added a mixture of ethyl acetate and ethanol, followed by stirring at room temperature, followed by filtration to obtain a white 8.1 g (75%) of a solid compound 4-1 was obtained.

Method for producing compound 4-2

After dissolving 10 g (22 mmol) of the compound 4-1 and 1-bromo-2-nitrobenzene (4.5 g, 22 mmol) in 60 mL of THF, 9.0 g (66 mmol) of potassium carbonate was dissolved in 20 mL of water . This was heated to reflux and 180 mg (0.02 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. When the reaction is complete, it is cooled to room temperature, extracted with CHCl ₃ and washed with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and recrystallized from ethyl acetate and ethanol to obtain 8.9 g (77%) of a white solid compound 4-2.

Method for producing compound 4-3

30 g (57 mmol) of the compound 4-2 and triethylphosphite (28.4 g, 171 mmol) were mixed and refluxed for 24 hours. When the reaction is completed, 400 mL of ethanol is added to the reaction product to precipitate a solid, which is then filtered. The filtered solid was added to a mixed solution of ethanol and ethyl acetate, stirred, and filtered to obtain 15 g (53%) of the objective compound 4-3 as white.

Preparation of Compound 1-h-20

15 g (30 mmol) of the compound 4-3 and iodobenzene (12.2 g, 60 mmol) were diluted in toluene, and 5.8 g (60 mmol) of NaOt-Bu was added thereto. Bis (tritiated-butylphosphine) palladium (0.1 g, 0.2 mmol) was added to the mixture under reflux and stirred for 4 hours. When the reaction was completed, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The residue was dissolved in 500 ml of chloroform, washed with 200 ml of water, and then dried over anhydrous magnesium sulfate, followed by filtration. The residue was recrystallized from a mixture of chloroform and ethyl acetate to obtain 11.6 g (68%) of the objective compound 1-h-20 as a white solid.

MS: [M + H] < ⁺ > = 571

Reaction Example 29) Synthesis of Compound 1-h-42

Method for producing compound 5-1

Bromo-2-nitrobenzene was used in the same manner as in the preparation of Intermediate 4-2 of Reaction Example 27, except that 2,4-dibromo-1-nitrobenzene (2,4 -dibromo-1-nitrobenzene) as a starting material, to obtain the title compound intermediate 5-1 as white.

Production method of Compound 5-2

20 g (33 mmol) of the compound 5-1 and 16.4 g (99 mmol) of triphenylphosphite were mixed and refluxed for 24 hours. When the reaction is completed, 300 mL of ethanol is added to the reaction product to precipitate a solid, which is then filtered. The filtered solid was added to a mixed solution of ethanol and ethyl acetate, stirred under heating, and filtered to obtain 12 g (57%) of the desired compound 5-2 as white.

Method for producing compound 5-3

12 g (18 mmol) of the compound 5-2 and 7.4 g (36 mmol) of iodobenzene are added to toluene, and then 5.1 g (54 mmol) of NaOt-Bu is added thereto. Bis (tritiated-butylphosphine) palladium (0.1 g, 0.2 mmol) was added to the mixture under reflux and stirred for 4 hours. When the reaction was completed, the reaction mixture was cooled to room temperature and the resulting solid was filtered. The residue was dissolved in 700 ml of chloroform, washed with 300 ml of water, and dried over anhydrous magnesium sulfate. This was recrystallized from a mixture of chloroform and ethyl acetate to obtain 10.8 g (74%) of the target compound 5-3 as a white solid.

Method for producing compound 1-h-42

7.0 g of 9-phenyl-9H-carbazol-3-yl) boronic acid and 15 g (23 mmol) of compound 5-3 were dissolved in tetrahydrofuran THF), and then 9.0 g (66 mmol) of potassium carbonate was dissolved in 20 mL of water and the mixture was added. This was heated to reflux and 180 mg (0.02 mmol) of tetrakis (triphenylphosphine) palladium (O) was added. When the reaction is complete, it is cooled to room temperature, extracted with CHCl ₃ and washed with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and recrystallized to obtain 12.1 g (65%) of a white solid compound 1-h-42.

MS: [M + H] < ⁺ > = 812

<Experimental Example 1>

The glass substrate coated with ITO (indium tin oxide) film with a thickness of 1,500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with 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.

Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the ITO transparent electrode prepared above to form a hole injection layer.

[LINE]

N, N-bis- (1,1-biphenyl) -4,4-diamine (NPB, (N, N-bis- (1-naphthalenyl) -N, N-bis-phenyl- (1,1-biphenyl) -4,4-diamine) was formed in a thickness of 400 Å by thermal vacuum deposition to form a hole transport layer.

Subsequently, the compound of the formula 1-a-1 prepared in the reaction example 1 was vacuum deposited on the hole transport layer to a film thickness of 300 angstroms with a dopant of Ir (ppy) ₃ and a concentration of 10% by weight (dopant / compound) to form a light emitting layer .

The following electron transport material was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer.

[Electron transport material]

Lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 Å on the electron injection and transport layer sequentially to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr.

<Experimental Example 2>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-a-2 was used instead of the compound of Formula 1-a-1.

<Experimental Example 3>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-a-1 was used instead of the compound of Formula 1-a-1.

<Experimental Example 4>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-f-1 was used instead of the compound of Formula 1-a-1.

<Experimental Example 5>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-g-34 was used instead of the compound of Formula 1-a-1.

&Lt; Comparative Example 1 &

In the same manner as in Experimental Example 1, except that the following H1 was used in place of the compound of Formula 1-a-1.

Table 4 shows the device results obtained by using the compounds in Experimental Examples 1 to 5 and Comparative Example 1 as the light emitting layer.

No. Host Dopant
(Dopant) Doping concentration
(%) The driving voltage (V)
@ 5,000 cd / m ² Luminous efficiency
(Cd / A) Comparative Example 1 H1 Ir (ppy) 3 10 5.2 36 Experimental Example 1 1-a-1 Ir (ppy) 3 10 5.2 20 Experimental Example 2 1-a-2 Ir (ppy) 3 10 5.7 44 Experimental Example 3 1-b-1 Ir (ppy) 3 10 4.7 39 Experimental Example 4 1-f-1 Ir (ppy) 3 10 4.2 40 Experimental Example 5 1-g-34 Ir (ppy) 3 10 4.1 42

As can be seen from the above Table 1, Examples 1 to 5 show that the compound of the present invention can be used as a host of a green light emitting layer and can exhibit lower voltage characteristics and improved efficiency than Comparative Example 1.

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

Claims (23)

A heterocyclic compound represented by the following formula (2) or (3):
(2)

(3)

In Formula 2,
a and d are each an integer of 1 to 4,
b is an integer of 1 to 7,
c is an integer of 1 to 6,
X is O, S, or NR,
R1 and R2 are each hydrogen or combine to form a 5-membered condensed ring,
when a is an integer of 2 to 4, a plurality of R 3 are the same as or different from each other,
When b is an integer of 2 to 7, a plurality of R4s may be the same or different from each other,
When c is an integer of 2 to 6, a plurality of R 5 s may be the same as or different from each other,
When d is an integer of 2 to 4, a plurality of R 6 are the same or different from each other,
R is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; Or an aryl group substituted or unsubstituted with a nitrile group,
When X is O or S,
R3 to R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group, or two or more groups adjacent to each other may be connected to each other to form a ring,
When X is NR,
R3 is hydrogen,
R4 to R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group, or two or more groups adjacent to each other may be connected to each other to form a ring,
In Formula 3,
X, a, b, c, d, R1 and R2 are the same as defined in Formula 2,
R is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group,
R3 to R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group, or two or more groups adjacent to each other may be connected to each other to form a ring. delete The method according to claim 1,
The heterocyclic compound represented by the above formula (2) or (3) is a heterocyclic compound represented by the following formula (4-1) or (5-1)
[Formula 4-1]

[Formula 5-1]

In Formula 4-1,
X, a, b, d, R and R1 to R6 are the same as defined in Formula 2,
In Formula 5-1,
X, a, b, d, R and R1 to R6 are the same as defined in the above formula (3). The method according to claim 1,
And X is S or O. The method according to claim 1,
And X is NR. The method according to claim 1,
In the case of Formula 3, X is NR and R is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The method according to claim 1,
R5 is hydrogen; A nitrile group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted aromatic heterocyclic group; Or a substituted or unsubstituted arylamine group. The method according to claim 1,
R5 is hydrogen; Or a heterocyclic compound which is any one of the following substituents:

,

,

,

,

,

,

,

,

,

And

In the substituent,
e is an integer of 1 to 4,
f and g are each an integer of 1 to 7,
h is an integer of 1 to 9,
i is an integer of 1 to 8,
L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent aromatic or aliphatic heterocyclic group,
R10 to R25 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide 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 heteroarylamine group; A substituted or unsubstituted imine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aromatic or aliphatic heterocyclic group. The method of claim 8,
L1 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted divalent carbazole group. The method according to claim 1,
R6 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The method according to claim 1,
Wherein the heterocyclic compound represented by Formula 2 or 3 is represented by any one of the following Formulas 1-a-1 to 1-a-4:

In the above formulas (1-a-5) and (1-a-6), R is the same as defined in claim 1. The method according to claim 1,
Wherein the heterocyclic compound represented by Formula 2 or 3 is represented by any one of the following Formulas 1-b-1 to 1-b-44:

The method according to claim 1,
The heterocyclic compound represented by Formula 2 or 3 is represented by any one of the following Formulas 1-c-1 to 1-c-48:

The method according to claim 1,
Wherein the heterocyclic compound represented by Formula 2 or 3 is represented by any one of the following Formulas 1-d-1 to 1-d-34:

The method according to claim 1,
Wherein the heterocyclic compound represented by Formula 2 or 3 is represented by any one of the following Formulas 1-e-1 to 1-e-48:

The method according to claim 1,
The heterocyclic compound represented by Formula 2 or 3 is represented by any one of the following Formulas 1-f-1 to 1-f-44:

The method according to claim 1,
Wherein the heterocyclic compound represented by Formula 2 or 3 is represented by any of Formula 1-g-1 to 1-g-39:

The method according to claim 1,
The heterocyclic compound represented by the above general formula (2) or (3) is a compound represented by the following general formulas (1-h-1 to 1-h-9, 1-h-18 to 1-h-30 and 1-h-40 to 1-h- Heterocyclic compounds represented by any one of the following:

A first electrode; A second electrode facing the first electrode; And at least one organic layer including a light emitting layer provided between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises the heterocyclic compound according to any one of claims 1 and 3 to 18. The method of claim 19,
Wherein the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously performing electron transport and electron injection,
Wherein the electron transporting layer, the electron injecting layer, or the layer that simultaneously transports electrons and injects electrons comprises the heterocyclic compound. The method of claim 19,
Wherein the light emitting layer comprises the heterocyclic compound. The method of claim 19,
Wherein the light emitting layer comprises the heterocyclic compound as a host. The method of claim 19,
Wherein the organic material layer includes a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes,
Wherein the hole transporting layer, the hole injecting layer, or the layer simultaneously transporting holes and injecting holes includes the heterocyclic compound.

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