KR20180004034A - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a heterocyclic compound represented by chemical formula 1 and an organic light emitting device comprising the same. A compound according to the present invention can be used as a material for an organic layer in an organic light emitting device, thereby being capable of improving efficiency, having low driving voltage and/or improving lifespan properties of an organic light emitting device.

Description

[0001] HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

This application claims the benefit of the filing date of Korean Patent Application No. 10-2016-0083734 filed on July 01, 2016, the entire contents of which are incorporated herein by reference.

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

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 an anode and a 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 this 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, an electron transport layer, and an electron injection layer.

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

Korean Patent Registration No. 10-1356941

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

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

[Chemical Formula 1]

In Formula 1,

R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted heterocyclic group,

L1 and L2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar 1 is a substituted or unsubstituted heterocyclic group,

R 1 to R 4 are the same or different from each other and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a and b each represent an integer of 0 to 4,

c is an integer of 0 to 3,

d is an integer from 0 to 5,

When a to d are each 2 or more, the substituents in the parentheses are the same or different from each other,

n1 and n2 are 0 or 1,

at least one of n1 and n2 is an integer of 1,

X1 and X2 are hydrogen or directly bonded to each other.

In addition, one embodiment of the present disclosure includes a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes the heterocyclic compound Emitting layer.

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. The compounds described herein can be used as hole injecting, hole transporting, hole injecting and hole transporting, electron suppressing, luminescence, hole blocking, electron transporting, or electron injecting materials.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 It is.

The present specification will be described in more detail below.

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

[Chemical Formula 1]

In Formula 1,

R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted heterocyclic group,

L1 and L2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar 1 is a substituted or unsubstituted heterocyclic group,

R 1 to R 4 are the same or different from each other and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a and b each represent an integer of 0 to 4,

c is an integer of 0 to 3,

d is an integer from 0 to 5,

When a to d are each 2 or more, the substituents in the parentheses are the same or different from each other,

n1 and n2 are 0 or 1,

at least one of n1 and n2 is an integer of 1,

X1 and X2 are hydrogen or directly bonded to each other.

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Boron 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 alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, the "substituent group to which at least two substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.

In this specification, "adjacent" The group may mean a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom of the substituent. 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 to each other.

"는 화학식 1 또는 코어구조에 결합되는 부위를 의미한다.In this specification, "*" and "

"Means a moiety bonded to the formula (1) or core structure.

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

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups. Do not.

In the present specification, the boron group may be represented by the formula of -BR _a R _b , wherein R _a and R _b are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 50, and according to one embodiment, has 1 to 30 carbon atoms. According to another embodiment, Lt; / RTI > Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, An n-pentyl group, a tert-butyl group, a tert-butyl group, a 3-methylbutyl group, a 3-methylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.

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

In the present specification, the 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 thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, a n-butoxy group, an isobutoxy group, a tert- , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n- , A benzyloxy group, a p-methylbenzyloxy group, and the like, but are not limited thereto.

In this specification, the amine group is -NH ₂ ; An alkylamine group; N-arylalkylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group and triphenylamine group, but are 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 a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.

In the present specification, the number of carbon atoms of the alkylamine group is not particularly limited, but may be 1 to 40, and according to one embodiment, the number of carbon atoms may be 1 to 30, and the number of carbon atoms may be 1 to 20 according to another embodiment. Specific examples of the alkylamine 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, Group, 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 containing two or more 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 a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, Group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, and a triphenylamine group.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroarylamine group containing two or more heteroaryl groups may simultaneously contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.

In the present specification, the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine 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.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but may be 6 to 60 carbon atoms. According to one embodiment, the number of carbon atoms may be 6 to 30, 20. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. The number of carbon atoms may be 10 to 60 according to one embodiment, and the number of carbon atoms may be 10 to 20 according to another embodiment. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

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

,

,

,

,

,

,

,

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 heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but may be 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms may be 2 to 30, and the number of carbon atoms may be 2 to 20 according to another embodiment. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl 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 pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzimidazole group, a benzoquinolinyl group, a benzopyridazinyl group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a thiazolyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazyl group and a dibenzofuranyl group, a benzoimidazonaphthylinin group, Benzoimidazophenanthridine group, and the like. It is not fixed.

The heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring.

In the present specification, the hydrocarbon ring may be an aliphatic, aromatic, or aliphatic and aromatic condensed ring, and examples of the cycloalkyl group or the aryl group may be selected, except that the hydrocarbon ring is not a monovalent group. The heterocyclic group may be an aliphatic, aromatic, or aliphatic and aromatic condensed ring, and examples of the heterocyclic group may be selected, except that the heterocyclic group is not a monovalent group.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, the alkylaryl group, the arylamine group and the arylheteroarylamine group, The description of one aryl group may be applied.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group and the alkylamine group can be applied to the alkyl group described above.

In the present specification, the heteroaryl group in the heteroaryl group, the heteroarylamine group and the arylheteroarylamine group can be applied to the description of the above-mentioned heterocyclic group.

In the present specification, the alkenyl group in the aralkenyl group and the arylalkenyl group can be applied to the description of the alkenyl group described above.

In the present specification, the alkyl group in the arylalkyl group and thioalkyl group can be applied to the alkyl group described above.

In the present specification, the description of the aryl group described above can be applied, except that the arylene group is a divalent group.

In this specification, the description of the above-mentioned heteroaryl group can be applied except that the heteroarylene group is a divalent group.

In one embodiment of the present specification, X1 and X2 are both hydrogen.

In another embodiment, X1 and X2 are directly bonded to each other to form a pentagonal ring.

In one embodiment of the present specification, n1 and n2 are 0 or 1, and at least one of n1 and n2 is an integer of 1.

According to another embodiment, n1 and n2 are integers of 1.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms. In one embodiment of the present specification, Ar1-L2-NR3R4 is one of the following structures.

In the above structures,

L2, R3 and R4 have the same definitions as in the above formula (1)

R ' and R "are the same or different from each other and each independently represents hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, aryloxy, alkylthio, arylthio, alkylsulfoxy, arylsulfoxy, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, Substituted or unsubstituted aralkylamine groups, substituted or unsubstituted heteroarylamine groups, substituted or unsubstituted arylamine groups, substituted or unsubstituted arylheteroarylamine groups, substituted or unsubstituted aryl A phosphine group, or a substituted or unsubstituted heterocyclic group,

The structures may be further substituted.

In one embodiment of the present invention, R 'and R "are the same or different from each other and each independently represents hydrogen, deuterium, halogen, silyl, boron, substituted or unsubstituted alkyl, substituted or unsubstituted A substituted or unsubstituted arylamine group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted arylamine group, Or an unsubstituted arylheteroarylamine group or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present invention, R 'and R "are the same or different from each other and each independently represents hydrogen, deuterium, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R 'and R "are the same or different and each independently represents hydrogen, deuterium, substituted or unsubstituted C1 to C50 alkyl, substituted or unsubstituted C3 to C60 A substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present specification, R 'and R "are the same or different from each other and each independently represents hydrogen, deuterium, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

In another embodiment, R 'and R "are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to another embodiment, R 'and R "are the same or different and each independently represents a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, or a substituted or unsubstituted tert-butyl group .

In another embodiment, R 'and R "are the same or different from each other, and each independently is a methyl group, an ethyl group or a tert-butyl group.

According to one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may be any one selected from the following Formulas 1-A to 1-D.

[Chemical Formula 1-A]

[Chemical Formula 1-B]

[Chemical Formula 1-C]

[Chemical Formula 1-D]

In the general formulas (1-A) to (1-D)

X1, X2, R1 to R8, L1, L2, n1 and n2 have the same definitions as in the above formula (1)

W1 to W4 are the same or different from each other and each independently O, S or SiT1T2,

T1, T2, R101 to R104 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

s1 and s3 are each an integer of 0 to 5,

s2 and s4 are each an integer of 0 to 7,

When s1 to s4 are each an integer of 2 or more, the substituents in parentheses are the same as or different from each other.

According to one embodiment of the present disclosure, s1 is 0 or 1.

According to one embodiment of the present disclosure, s2 is 0 or 1.

According to one embodiment of the present disclosure, s3 is 0 or 1.

According to one embodiment of the present disclosure, s4 is 0 or 1.

In another embodiment, T1 and T2 are the same or different and independently selected from the group consisting of hydrogen; Or a substituted or unsubstituted alkyl group.

According to another embodiment, T1 and T2 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.

In another embodiment, T1 and T2 are the same or different and independently selected from the group consisting of hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to another embodiment, T1 and T2 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted t-butyl group.

In another embodiment, T1 and T2 are methyl groups.

In one embodiment of the present specification, R101 to R104 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another embodiment, R101 to R104 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, R101 to R104 are the same or different from each other and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, R101 to R104 are hydrogen.

In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present specification, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C25 heterocyclic group.

In another embodiment, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C25 heterocyclic group.

According to another embodiment, R5 to R8 may be the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthylene group; Or a substituted or unsubstituted dibenzofurane group.

In another embodiment, R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; An ethyl group; tert-butyl group; A phenyl group; A biphenyl group; Naphthylene group; Or a dibenzofurane group.

According to another embodiment, R5 and R8 are hydrogen.

In one embodiment of the present invention, L 1 and L 2 are the same or different from each other and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

In another embodiment, L 1 and L 2 are the same or different and are each independently a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanyl group; A substituted or unsubstituted pyrrolene group; A substituted or unsubstituted dibenzofuranylene group; A substituted or unsubstituted dibenzothiophenylene group; Or a substituted or unsubstituted carbazolylene group.

According to another embodiment, L1 and L2 are the same or different from each other, and each independently represents a phenylene group; Biphenyllylene groups; A terphenylene group; A naphthalene group; A 9,9-diphenylfluorenyl group; A 9,9-dimethylfluorenyl group; Phenanthrenylene group; Anthracenylene group; A triphenylrenyl group; Thiophenylene group; A furanylene group; A pyrrolene group substituted or unsubstituted with a methyl group or a phenyl group; Dibenzofuranyl group; Dibenzothiophenylene groups; Or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

In one embodiment of the present invention, L 1 and L 2 are the same or different from each other and are each independently a direct bond; Or one of the following structures.

In one embodiment of the present disclosure, L1 and L2 are direct bonds.

In one embodiment of the present invention, R 1 to R 4 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, R 1 to R 4 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another embodiment, R 1 to R 4 are the same or the same and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another embodiment, R 1 to R 4 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another embodiment, R 1 to R 4 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted crecenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted indenofluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrazinyl group; A substituted or unsubstituted pyridazinyl group; A substituted or unsubstituted pyrimidinyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted quinoxalinyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted naphthobenzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzoimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted fluorenobenzofurane group; Or a substituted or unsubstituted benzofuranodibenzofurane group.

In one embodiment of the present invention, R 1 to R 4 may be the same or different from each other and each independently selected from the structures described below.

In the above structures,

R201 to R297 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Silyl group; Boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a1, a6, a10, a23 and a25 are each an integer of 0 to 5,

a5, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17 to b32 are each an integer of 0 to 4,

a3 and a22 are each an integer of 0 to 7,

a4, a7, a12, a15. a19, a26 and a27 are each an integer of 0 to 3,

a11 is an integer of 0 to 9,

a13, a20 and a24 are each an integer of 0 to 6,

a18, b5, b10, b14 and b16 are each an integer of 0 to 2,

When a18, b5, b10, b14 and b16 are 2, the substituents in parentheses are different from each other,

b3, b3, b3, b3, b3, b3, b3, b3, a3, a22, a4, a7, a12, a15. a19, a26, a27, a11, a13, a20 and a24 are each 2 or more, the substituents in the parentheses are the same or different from each other.

In one embodiment of the present specification, R201 to R297 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

In another embodiment, R201 to R297 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; Silyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, R201 to R297 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; Silyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

In another embodiment, R201 to R297 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A silyl group substituted or unsubstituted with an alkyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

According to another embodiment, R201 to R297 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A silyl group substituted with a methyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted t-butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted cyclopentyl group; Or a substituted or unsubstituted cyclohexyl group.

In another embodiment, R201 to R297 are the same or different from each other and each independently hydrogen; heavy hydrogen; Fluorine (F); A trimethylsilyl group; Methyl group; t-butyl group; A phenyl group; Or a biphenyl group.

In one embodiment of the present invention, a1 to a35 and b1 to b32 are integers of 0 to 2, respectively.

In one embodiment of the present invention, R 1 to R 4 are the same or different and are each independently a phenyl group substituted or unsubstituted with a fluorine (-F), a methyl group, a t-butyl group or a trimethylsilyl group; A 9,9-dimethylfluorenyl group; Naphthyl group; Or a dibenzofuranyl group.

According to an embodiment of the present invention, the heterocyclic compound of Formula 1 may be any one selected from the following heterocyclic compounds.

The compound according to one embodiment of the present specification can be produced by a production method described below. For example, the compound of formula (1) can be prepared in the following manner. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

According to one embodiment of the present disclosure, there is provided a liquid crystal display comprising: a 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 above-described heterocyclic compound.

According to one embodiment of the present disclosure, the organic material layer of the organic light emitting device 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, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.

The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially stacked on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3, or the electron transporting layer 7.

According to one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or an electron blocking layer, and the hole injecting layer, the hole transporting layer, or the electron blocking layer includes the heterocyclic compound represented by Formula 1 .

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the general formula (1).

According to an embodiment of the present invention, the organic layer includes a light emitting layer, the light emitting layer includes a heterocyclic compound represented by Formula 1, and the light emitting layer further includes a compound represented by Formula 2 below.

(2)

In Formula 2,

R9 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted heterocyclic group,

p is an integer of 0 to 6,

When p is 2 or more, the substituents in the parentheses are the same or different from each other,

L3 to L6 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group,

Ar 2 to Ar 5 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R9 is hydrogen; heavy hydrogen; A halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R9 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R9 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present specification, R9 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C25 heterocyclic group.

According to another embodiment, R9 is hydrogen.

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

In one embodiment of the present invention, L3 to L6 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present invention, L3 to L6 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

According to another embodiment, L3 to L6 are the same or different and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanyl group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another embodiment, L3 to L6 are the same or different and are each independently a direct bond; A phenylene group; Biphenyllylene groups; A terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group; Thiophenylene group; A furanylene group; Dibenzothiophenylene groups; Dibenzofuranyl group; Or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

According to another embodiment, L3 to L6 are the same or different and are each independently a direct bond; Or one of the following structures.

According to one embodiment of the present disclosure, L3 is a direct bond.

According to one embodiment of the present disclosure, L4 is a phenylene group.

According to one embodiment of the present disclosure, L5 and L6 are direct bonds.

In one embodiment of the present specification, Ar2 to Ar5 are the same or different from each other and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another embodiment, Ar2 to Ar5 are the same or different from each other, and each independently hydrogen; An aryl group having 6 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with a heteroaryl group having 2 to 60 carbon atoms; Or a heteroaryl group having 2 to 60 carbon atoms, which is substituted or unsubstituted with an aryl group having 60 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.

In another embodiment, Ar2 to Ar5 are the same or different from each other and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilyl group.

According to another embodiment, Ar2 to Ar5 are the same or different from each other, and each independently hydrogen; A phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with an aryl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with an aryl group; A carbazole group substituted or unsubstituted with an alkyl group or an aryl group; An alkyl group, or a fluorene group substituted or unsubstituted with an aryl group; A thiophene group substituted or unsubstituted with an aryl group; A furan group substituted or unsubstituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group substituted or unsubstituted with an alkyl group or an aryl group; A benzofluorene group substituted or unsubstituted with an alkyl group or an aryl group; Indolecarbazole group; A pyridyl group; An isoquinolyl group substituted or unsubstituted with an aryl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with an aryl group; A triazine group substituted or unsubstituted with an aryl group; A benzimidazole group substituted or unsubstituted with an aryl group; A benzoxazole group substituted or unsubstituted with an aryl group; A benzothiazole group substituted or unsubstituted with an aryl group; An alkyl group, or a dihydroacridine group substituted or unsubstituted with an aryl group; A xanthene group substituted or unsubstituted with an alkyl group or an aryl group; Or a dibenzosilyl group substituted or unsubstituted with an alkyl group or an aryl group.

In another embodiment, Ar2 to Ar5 are the same or different from each other and each independently hydrogen; A phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with a phenyl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with a phenyl group; A carbazole group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A methyl group, or a fluorene group substituted or unsubstituted with a phenyl group; A thiophene group substituted or unsubstituted with a phenyl group; A furan group substituted or unsubstituted with a phenyl group; Benzothiophene group; Benzofuran group; A methyl group, or a benzocarbazole group substituted or unsubstituted with a phenyl group; A methyl group, or a benzofluorene group substituted or unsubstituted with a phenyl group; Indolecarbazole group; A pyridyl group substituted or unsubstituted with a phenyl group or a naphthyl group; An isoquinolyl group substituted or unsubstituted with a phenyl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group; A benzimidazole group substituted or unsubstituted with a phenyl group; A benzoxazole group substituted or unsubstituted with a phenyl group; A benzothiazole group substituted or unsubstituted with a phenyl group; A methyl group, or a dihydroacridine group substituted or unsubstituted with a phenyl group; A methyl group, or a xanthylene group substituted or unsubstituted with a phenyl group; Or a dibenzosilyl group substituted or unsubstituted with a methyl group or a phenyl group.

In one embodiment of the present specification, Ar2 to Ar5 are the same or different from each other, and each independently hydrogen; Or one of the following structures.

According to an embodiment of the present invention, the organic layer includes a light emitting layer, the light emitting layer includes a heterocyclic compound represented by Formula 1, and the light emitting layer further includes a compound represented by Formula 3 below.

(3)

In Formula 3,

R10 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted heterocyclic group,

q is an integer of 0 to 7,

When q is 2 or more, the substituents in the parentheses are the same or different from each other,

L7 to L9, which may be the same or different, are each independently a direct bond; Or a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar6 to Ar8 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present disclosure, R10 is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R10 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R10 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present specification, R10 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C25 heterocyclic group.

In another embodiment, R10 is hydrogen.

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

In one embodiment of the present invention, L7 to L9 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present invention, L7 to L9 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

According to another embodiment, L7 to L9 are the same or different from each other, and each independently is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanyl group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another embodiment, L7 to L9 are the same or different and are each independently a direct bond; A phenylene group; Biphenyllylene groups; A terphenylene group; Naphthylene group; Anthracenylene group; Phenanthrenylene group; Triphenylene group; A fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group; Thiophenylene group; A furanylene group; Dibenzothiophenylene groups; Dibenzofuranyl group; Or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

According to another embodiment, L7 to L9 are the same or different from each other, and each independently is a direct bond; Or one of the following structures.

In one embodiment of the present invention, L7 to L9 are direct bonds.

In one embodiment of the present specification, Ar6 to Ar8 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another embodiment, Ar 6 to Ar 8 are the same or different and each independently represents an aryl group having 6 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with a heteroaryl group having 2 to 60 carbon atoms group; Or a heteroaryl group having 2 to 60 carbon atoms, which is substituted or unsubstituted with an aryl group having 60 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.

In another embodiment, Ar6 to Ar8 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilyl group.

According to another embodiment, Ar6 to Ar8 are the same or different from each other, and each independently represents a phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with an aryl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with an aryl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with an aryl group; A carbazole group substituted or unsubstituted with an alkyl group or an aryl group; An alkyl group, or a fluorene group substituted or unsubstituted with an aryl group; A thiophene group substituted or unsubstituted with an aryl group; A furan group substituted or unsubstituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group substituted or unsubstituted with an alkyl group or an aryl group; A benzofluorene group substituted or unsubstituted with an alkyl group or an aryl group; Indolecarbazole group; A pyridyl group; An isoquinolyl group substituted or unsubstituted with an aryl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with an aryl group; A triazine group substituted or unsubstituted with an aryl group; A benzimidazole group substituted or unsubstituted with an aryl group; A benzoxazole group substituted or unsubstituted with an aryl group; A benzothiazole group substituted or unsubstituted with an aryl group; An alkyl group, or a dihydroacridine group substituted or unsubstituted with an aryl group; A xanthene group substituted or unsubstituted with an alkyl group or an aryl group; Or a dibenzosilyl group substituted or unsubstituted with an alkyl group or an aryl group.

In another embodiment, Ar6 to Ar8 are the same or different from each other and are each independently a phenyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Phenanthrene; Anthracene group; Triphenylene group; A dibenzofurane group substituted or unsubstituted with a phenyl group; A naphthobenzofuran group; A dibenzothiophene group substituted or unsubstituted with a phenyl group; A carbazole group substituted or unsubstituted with a methyl group, an ethyl group, or a phenyl group; A methyl group, or a fluorene group substituted or unsubstituted with a phenyl group; A thiophene group substituted or unsubstituted with a phenyl group; A furan group substituted or unsubstituted with a phenyl group; Benzothiophene group; Benzofuran group; A methyl group, or a benzocarbazole group substituted or unsubstituted with a phenyl group; A methyl group, or a benzofluorene group substituted or unsubstituted with a phenyl group; Indolecarbazole group; A pyridyl group substituted or unsubstituted with a phenyl group or a naphthyl group; An isoquinolyl group substituted or unsubstituted with a phenyl group; Quinolyl group; A quinazolyl group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group; A benzimidazole group substituted or unsubstituted with a phenyl group; A benzoxazole group substituted or unsubstituted with a phenyl group; A benzothiazole group substituted or unsubstituted with a phenyl group; A methyl group, or a dihydroacridine group substituted or unsubstituted with a phenyl group; A methyl group, or a xanthylene group substituted or unsubstituted with a phenyl group; Or a dibenzosilyl group substituted or unsubstituted with a methyl group or a phenyl group.

In one embodiment of the present invention, Ar6 to Ar8 may be the same or different from each other, and each independently selected from the following structures.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the general formula (1) as a host of the light emitting layer.

According to an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound represented by the formula (1) as a dopant in the light emitting layer.

According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer contains the heterocyclic compound represented by Formula 1 as a dopant of the light emitting layer, As a host.

According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer contains the heterocyclic compound represented by Formula 1 as a dopant of the light emitting layer, Host, and the heterocyclic compound represented by Formula 1 may be doped with 2 to 10 wt%.

According to an embodiment of the present invention, the organic compound layer includes a hole blocking layer, an electron transporting layer, or an electron injecting layer, and the hole blocking layer, the electron transporting layer, or the electron injecting layer includes the heterocyclic compound represented by Formula 1 .

According to an embodiment of the present invention, the organic material layer may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

An organic light emitting device according to an embodiment of the present invention includes a first electrode; A second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer comprises the heterocyclic compound represented by Formula 1.

According to another embodiment, the organic light emitting device of the present invention includes a first electrode; A second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by Formula 1 as a dopant, and may further include a host.

In another embodiment, the organic light emitting device of the present invention includes a first electrode; A second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer includes a heterocyclic compound represented by Formula 1 as a dopant and may further include a host, 2 or 3. < / RTI > The organic light emitting device may further include at least one organic material layer selected from a hole transporting layer, a hole injecting layer, an electron transporting layer, and an electron injecting layer in addition to the light emitting layer. However, the structure of the organic light emitting device is not limited thereto.

According to another embodiment, the organic light emitting device of the present invention includes a first electrode; A second electrode; And a light emitting layer provided between the first electrode and the second electrode, and at least one organic material layer selected from a hole injecting layer and a hole transporting layer may be disposed between the first electrode and the light emitting layer, And at least one organic material layer selected from an electron transporting layer and an electron injecting layer. However, the structure of the organic light emitting device of the present invention is not limited thereto.

In another embodiment, the organic light emitting device of the present invention includes a first electrode; A second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer comprises a heterocyclic compound represented by Formula 1 as a host, and between the first electrode and the light emitting layer, a hole injecting layer and a hole transporting layer And one or more organic layers selected from an electron transport layer and an electron injection layer may be disposed between the second electrode and the light emitting layer. However, the structure of the organic light emitting device of the present invention is not limited thereto.

According to another embodiment, the organic light emitting device of the present invention includes a first electrode; A second electrode; And a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer contains the heterocyclic compound represented by Formula 1 as a dopant and the compound represented by Formula 2 or 3 as a host of the light emitting layer And at least one organic material layer selected from a hole injecting layer and a hole transporting layer may be disposed between the first electrode and the light emitting layer, and at least one organic material layer selected from an electron transporting layer and an electron injecting layer may be disposed between the second electrode and the light emitting layer . However, the structure of the organic light emitting device of the present invention is not limited thereto.

The organic light emitting device of the present invention is manufactured by materials and methods known in the art except that one or more of the organic layers include the heterocyclic compound of the present specification, that is, the heterocyclic compound represented by the above formula (1) .

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.

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 metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. The heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

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

According to another embodiment of the present invention, 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, LiO ₂ / Al, and Mg / Ag, but are not limited thereto.

The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting 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 of the light emitting layer 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 high 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; Benzoxazole, benzothiazole and benzimidazole compounds; 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 may be 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 heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. 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.

A layer that receives electrons from the electron injecting layer of the electron transporting 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. Do. 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, perylenetetracarboxylic 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.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

< Synthetic example >

Synthetic example  1. Synthesis of intermediate 1-a

Intermediate 1-a was synthesized according to Reaction Scheme 1 below.

<Reaction Scheme 1>

(20.0 g, 74 mmol) and 4-dibenzofuranylboronic acid (17.3 g, 82 mmol) were completely dissolved in 300 mL of tetrahydrofuran, and potassium carbonate (30.7 g, 222 mmol ) Aqueous solution was added, tetrakis- (triphenylphosphine) palladium (0.86 g, 0.74 mmol) was added, and the mixture was refluxed for 24 hours and stirred. After completion of the reaction, the temperature was lowered to room temperature, and the mixture was extracted with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate to obtain <Intermediate 1-a> (21.7 g, 82%).

MS [M &lt; + &gt;] = 356.06

Synthetic example  2. Synthesis of intermediate 1-b

Intermediate 1-b was synthesized according to Reaction Scheme 2 below.

<Reaction Scheme 2>

(25.0 g, 56 mmol) was dissolved in 300 mL of tetrahydrofuran, and sodium chlorite (5.6 g, 62 mmol) and sulfamic acid (8.2 g, 84 mmol) And the mixture was heated and stirred for 4 hours. After completion of the reaction, the temperature was lowered to room temperature, and the mixture was extracted with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain <Intermediate 1-b> (18.8 g, 90%).

MS [M &lt; + &gt;] = 372.80

Synthetic example  3. Synthesis of intermediate 1-c

Intermediate 1-c was synthesized according to Reaction Scheme 3 below.

<Reaction Scheme 3>

<Intermediate 1-b> (18.0 g, 48 mmol) and 250 mL of methanesulfonic acid were placed and the mixture was heated and stirred at 80 ° C for 9 hours. After completion of the reaction, the temperature was lowered to room temperature, and then slowly added dropwise to water to form a solid. The resulting solid was washed with water and ethanol to obtain <Intermediate 1-c> (16.2 g, 95%).

MS [M &lt; + &gt;] = 354.79

Synthetic example  4. Synthesis of intermediate 1-d

Intermediate 1-d was synthesized according to Reaction Scheme 4 below.

<Reaction Scheme 4>

<Intermediate 1-c> (10.0 g, 28.1 mmol) was added to 300 mL of dichloromethane and stirred. Then bromine (6.76 g, 42.3 mmol) diluted in 50 mL of dichloromethane was slowly added dropwise and stirred at room temperature for 48 hours Respectively. The resulting replacement was then filtered and washed with dichloromethane and hexane. The solid was recrystallized from toluene and hexane to obtain <Intermediate 1-d> (7.92 g, 65%).

MS [M &lt; + &gt;] = 433.69

Synthesis Example 5. Synthesis of Intermediate 1-e

Intermediate 1-e was synthesized according to Reaction Scheme 5 below.

<Reaction Scheme 5>

9- (2-bromophenyl) -9H-carbazole (6.13 g, 19.0 mmol) and 150 mL of tetrahydrofuran were placed in a nitrogen atmosphere and cooled to -78 deg. N-butyl lithium (7.60 mL, 19.0 mmol) was added dropwise to the cooled reaction solution and stirred for 1 hour. <Intermediate 1-d> (7.50 g, 17.3 mmol) was added thereto, followed by stirring at room temperature. After completion of the reaction, saturated sodium hydrogencarbonate was added thereto to terminate the reaction, followed by extraction with ethyl acetate and water. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain <Intermediate 1-e> (8.31 g, 71%).

Synthetic example  6. Synthesis of intermediate 1-f

Intermediate 1-f was synthesized according to Scheme 6 below.

<Reaction Scheme 6>

<Intermediate 1-e> (8.00 g, 11.8 mmol), acetic acid (100 mL) and 2 drops of sulfuric acid were added and the mixture was heated and stirred for 3 hours. After completion of the reaction, the solid was filtered out, washed with water and ethanol, and then recrystallized from ethyl acetate and hexane to obtain Intermediate 1-f (7.40 g, 95%).

MS [M &lt; + &gt;] = 658.98

Synthetic example  7. Synthesis of Compound 1

Compound 1 was synthesized according to Reaction Scheme 7 below.

<Reaction Scheme 7>

(6.0 g, 9.10 mmol), bis (4-tertbutylphenyl) amine (5.63 g, 20.0 mmol) and sodium tert-butoxide (4.37 g, 45.5 mmol) were added to a round bottom flask in a nitrogen atmosphere. Bis (tri-tert-butylphosphine) palladium (0) (0.23 g, 0.46 mmol) was added to 80 mL of toluene, and the mixture was refluxed and stirred. After the reaction was completed, the mixture was cooled to room temperature, extracted with toluene and water, and the water layer was removed. The mixture was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The product was purified by column chromatography, and then recrystallized from toluene and hexane to obtain Compound 1 (6.03 g, 60%).

MS [M &lt; + &gt;] = 1104.5

Synthetic example  8. Synthesis of Compounds 2, 10 and 11

Compounds 2, 10 and 11 were synthesized according to Synthesis Example 7 using <Intermediate 1-f>, 4-tertbutylphenyl-4-trimethylsilylphenylamine and di-ols-tolyl amine, 2-fluoro- Respectively.

Compound 2; MS [M &lt; + &gt;] = 1136.6, Compound 10; MS [M &lt; + &gt;] = 936.1, Compound 11; MS [M &lt; + &gt;] = 944.1

Synthetic example  9. Synthesis of intermediate 3-a

<Intermediate 3-a> was synthesized according to Synthesis Example 1 using 1-dibenzofuranylboronic acid.

MS [M &lt; + &gt;] = 356.06

Synthetic example  10. Synthesis of intermediate 3-f

<Intermediate 3-f> was synthesized according to Synthesis Examples 2 to 6 using <Intermediate 3-a>.

MS [M &lt; + &gt;] = 658.98

Synthetic example  11. Synthesis of compounds 3, 4, 6 and 7

The reaction of intermediate 3-f with 4-tert-butylphenyl-9-dimethylfluoreneamine, 4-tert-butylphenyl-4-dibenzofurylamine, 4- -1-naphthalenamine was used to synthesize Compounds 3, 4, 6 and 7 respectively according to Synthesis Example 7.

Compound 3; MS [M &lt; + &gt;] = 1224.6, Compound 4; MS [M &lt; + &gt;] = 1172.4, Compound 6; MS [M &lt; + &gt;] = 1092.4, Compound 7; MS [M &lt; + &gt;] = 1092.4

Synthetic example  12. Synthesis of intermediate 5-a

<Intermediate 5-a> was synthesized according to Synthesis Example 1 using 1-dimethylfluoreneboronic acid.

MS [M &lt; + &gt;] = 398.96

Synthetic example  13. Synthesis of intermediate 5-f

<Intermediate 5-a> was synthesized according to Synthesis Examples 2 to 6 using <Intermediate 5-a>. .

MS [M &lt; + &gt;] = 701.14

Synthetic example  14. Synthesis of Compound 5

Compound 5 was synthesized according to Synthesis Example 7 using <Intermediate 5-f> and bis-4-tert-butylamine.

Compound 5; MS [M &lt; + &gt;] = 1146.6

Synthetic example  15. Synthesis of intermediate 8-a

Intermediate 8-a &gt; was synthesized according to Synthesis Example 1 using 4-naphthobenzofuranboronic acid.

MS [M &lt; + &gt;] = 406.87

Synthetic example  16. Synthesis of intermediate 8-f

<Intermediate 8-f> was synthesized according to Synthesis Examples 2 to 6 using <Intermediate 8-a>.

MS [M &lt; + &gt;] = 709.04

Synthetic example  17. Synthesis of Compound 8

Compound 8 was synthesized according to Synthesis Example 8 using <Intermediate 8-f> and bis-4-tert-butylphenylamine.

Compound 8; MS [M &lt; + &gt;] = 1154.5

Synthetic example  18. Synthesis of intermediate 9-a

Intermediate 9-a &gt; was synthesized according to Synthesis Example 1 using 4-dibenzothiopheneboronic acid.

MS [M &lt; + &gt;] = 372.87

Synthetic example  19. Synthesis of intermediate 9-f

<Intermediate 9-f> was synthesized according to Synthesis Examples 2 to 6 using <Intermediate 9-a>.

MS [M &lt; + &gt;] = 675.04

Synthetic example  20. Synthesis of Compound 9

Compound 9 was synthesized according to Synthesis Example 7 using <Intermediate 9-f> and 4-tert-butylphenyl-1-phenylamine.

Compound 9; MS [M &lt; + &gt;] = 1008.3

< Example >

Example  One.

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water containing a dispersing agent and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

The HAT was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 50 Å to form a hole injection layer. The HT-A was vacuum deposited on the HT-A as a hole transport layer, and HT-B was deposited thereon to a thickness of 100 Å. The light emitting layer was doped with 2 to 10 wt% of H-A and Compound 1 as a host and vacuum-deposited to a thickness of 200 ANGSTROM. Then, ET-A and Liq were deposited at a ratio of 1: 1 to 300 ANGSTROM, followed by sequentially depositing 150 ANGSTROM-doped magnesium (Mg) doped with 10 wt% of Mg and aluminum having a thickness of 1,000 ANGSTROM to form a cathode To prepare an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of LiF was 0.2 Å / sec, and the deposition rate of aluminum was 3 Å / sec to 7 Å / sec.

Example  2.

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in Example 1.

Example  3.

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in Example 1 above.

Example  4.

An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 7 was used instead of Compound 1 in Example 1.

Example  5.

An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 10 was used instead of Compound 1 in Example 1.

Example  6.

An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 11 was used instead of Compound 1 in Example 1.

Example  7.

An organic light emitting device was prepared in the same manner as in Example 1 except that H-B was used instead of the host H-A.

Example  8.

An organic light emitting device was prepared in the same manner as in Example 7, except that Compound 3 was used instead of Compound 1 in Example 7.

Example  9.

An organic light emitting device was prepared in the same manner as in Example 7, except that Compound 4 was used instead of Compound 1 in Example 7.

Example  10.

An organic light emitting device was prepared in the same manner as in Example 7, except that Compound 7 was used instead of Compound 1 in Example 7.

Example  11.

An organic light emitting device was prepared in the same manner as in Example 7, except that Compound 10 was used instead of Compound 1 in Example 7.

Example  12.

An organic light emitting device was prepared in the same manner as in Example 7, except that Compound 11 was used instead of Compound 1 in Example 7.

Example  13.

An organic light emitting device was prepared in the same manner as in Example 13, except that H-C was used instead of the host H-A.

Example  14.

An organic light emitting device was prepared in the same manner as in Example 13 except that Compound 3 was used instead of Compound 1 in Example 13.

Example  15.

An organic light emitting device was prepared in the same manner as in Example 13 except that Compound 4 was used instead of Compound 1 in Example 13.

Example  16.

An organic light emitting device was prepared in the same manner as in Example 13, except that Compound 7 was used instead of Compound 1 in Example 13.

Example  17.

An organic light emitting device was prepared in the same manner as in Example 13, except that Compound 10 was used instead of Compound 1 in Example 13.

Example  18.

An organic luminescent device was prepared in the same manner as in Example 13, except that Compound 11 was used instead of Compound 1 in Example 13.

< Comparative Example >

Comparative Example  One.

An organic luminescent device was prepared in the same manner as in Example 1, except that D-1 was used instead of the compound 1 in Example 1.

Comparative Example  2.

An organic luminescent device was prepared in the same manner as in Example 1 except that D-2 was used instead of the compound 1 in Example 1.

Comparative Example  3.

An organic luminescent device was fabricated in the same manner as in Example 1, except that D-3 was used instead of the compound 1 in Example 1.

Comparative Example  4.

An organic light emitting device was prepared in the same manner as in Example 7 except that D-1 was used instead of the compound 1 in Example 7.

Comparative Example  5.

An organic luminescent device was fabricated in the same manner as in Example 7 except that D-2 was used instead of the compound 1 in Example 7.

Comparative Example  6.

An organic luminescent device was prepared in the same manner as in Example 7, except that D-3 was used instead of the compound 1 in Example 7.

Comparative Example  7.

An organic luminescent device was prepared in the same manner as in Example 13 except that D-1 was used instead of the compound 1 in Example 13.

Comparative Example  8.

An organic luminescent device was prepared in the same manner as in Example 13 except that D-2 was used instead of the compound 1 in Example 13.

Comparative Example  9.

An organic luminescent device was prepared in the same manner as in Example 13 except that D-3 was used instead of the compound 1 in Example 13.

The organic light emitting devices of Examples 1 to 18 and Comparative Examples 1 to 9 were measured for the driving voltage and the luminous efficiency at a current density of 10 mA / cm 2, and at a current density of 20 mA / cm 2, (LT95). The results are shown in Table 1 below.

Example Host Dopant @ 10mA / cm ² @ 20mA / cm ² Voltage (V) Efficiency (cd / A) CIE (x, y) Life (hr) Example 1 H-A Compound 1 4.2 6.28 (0.143, 0.042) 120 Example 2 H-A Compound 3 4.2 6.54 (0.141, 0.045) 120 Example 3 H-A Compound 4 4.3 6.66 (0.142, 0.044) 115 Example 4 H-A Compound 7 4.3 6.31 (0.143, 0.042) 125 Example 5 H-A Compound 10 4.3 6.11 (0.142, 0.044) 120 Example 6 H-A Compound 11 4.2 6.06 (0.142,0.045) 115 Example 7 H-B Compound 1 4.1 6.09 (0.142, 0.042) 120 Example 8 H-B Compound 3 4.2 6.42 (0.141, 0.043) 130 Example 9 H-B Compound 4 4.1 6.41 (0.141, 0.045) 115 Example 10 H-B Compound 7 4.0 6.22 (0.143, 0.044) 125 Example 11 H-B Compound 10 4.1 6.17 (0.141, 0.043) 115 Example 12 H-B Compound 11 4.1 6.22 (0.142, 0.044) 125 Example 13 H-C Compound 1 4.0 6.06 (0.143, 0.045) 120 Example 14 H-C Compound 3 3.9 6.31 (0.142,0.046) 130 Example 15 H-C Compound 4 4.0 6.30 (0.142,0.046) 135 Example 16 H-C Compound 7 3.9 6.03 (0.144, 0.045) 135 Example 17 H-C Compound 10 4.0 5.83 (0.142,0.045) 125 Example 18 H-C Compound 11 4.0 5.94 (0.142,0.046) 130 Comparative Example 1 H-A D-1 4.4 5.13 (0.143, 0.042) 75 Comparative Example 2 H-A D-2 4.4 3.50 (0.141, 0.045) 50 Comparative Example 3 H-A D-3 4.3 5.12 (0.142, 0.044) 85 Comparative Example 4 H-B D-1 4.3 5.03 (0.143, 0.042) 80 Comparative Example 5 H-B D-2 4.2 3.61 (0.142, 0.044) 50 Comparative Example 6 H-B D-3 4.3 5.22 (0.142,0.045) 70 Comparative Example 7 H-C D-1 4.1 4.98 (0.144, 0.045) 80 Comparative Example 8 H-C D-2 4.2 3.66 (0.141, 0.044) 60 Comparative Example 9 H-C D-3 4.2 5.12 (0.142,0.046) 90

Comparing Examples 1 to 18 and Comparative Examples 1 to 9 in Table 1, the organic light emitting device including the heterocyclic compound represented by Formula 1 has a three-dimensional structure, Suppresses intermolecular fluorescence attenuation and shows excellent performance. In addition, in the cation condition, the electron density distribution of HOMO is distributed in the indoleacridine part with the nitrogen which is known to have a stable cation state, resulting in improvement of device life. Therefore, it was confirmed that the organic light emitting device of Comparative Examples 1 to 9 including the pyrene-based or fluorene-based compound had better efficiency and lifetime characteristics than the organic light emitting device.

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

Claims (17)

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

In Formula 1,
R5 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted heterocyclic group,
L1 and L2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar 1 is a substituted or unsubstituted heterocyclic group,
R 1 to R 4 are the same or different from each other and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a and b each represent an integer of 0 to 4,
c is an integer of 0 to 3,
d is an integer from 0 to 5,
When a to d are each 2 or more, the substituents in the parentheses are the same or different from each other,
n1 and n2 are 0 or 1,
at least one of n1 and n2 is an integer of 1,
X1 and X2 are hydrogen or directly bonded to each other. The method according to claim 1,
Arl-L2-NR3R4 is one of the following structures:

L2, R3 and R4 have the same definitions as in the above formula (1)
R ' and R "are the same or different from each other and each independently represents hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, aryloxy, alkylthio, arylthio, alkylsulfoxy, arylsulfoxy, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, Substituted or unsubstituted aralkylamine groups, substituted or unsubstituted heteroarylamine groups, substituted or unsubstituted arylamine groups, substituted or unsubstituted arylheteroarylamine groups, substituted or unsubstituted aryl A phosphine group, or a substituted or unsubstituted heterocyclic group,
The structures may be further substituted. The method according to claim 1,
L1 and L2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms. The method according to claim 1,
L1 and L2 are the same or different from each other, and are each independently a direct bond; Or a heterocyclic compound which is one of the following structures:

. The method according to claim 1,
R 1 to R 4 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. The method according to claim 1,
Wherein R1 to R4 are the same or different and are each independently one of the following structures:

In the above structures,
R201 to R297 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Silyl group; Boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a1, a6, a10, a23 and a25 are each an integer of 0 to 5,
a5, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17 to b32 are each an integer of 0 to 4,
a3 and a22 are each an integer of 0 to 7,
a4, a7, a12, a15. a19, a26 and a27 are each an integer of 0 to 3,
a11 is an integer of 0 to 9,
a13, a20 and a24 are each an integer of 0 to 6,
a18, b5, b10, b14 and b16 are each an integer of 0 to 2,
When a18, b5, b10, b14 and b16 are 2, the substituents in parentheses are different from each other,
b3, b3, b3, b3, b3, b3, b3, b3, a3, a22, a4, a7, a12, a15. a19, a26, a27, a11, a13, a20 and a24 are each 2 or more, the substituents in the parentheses are the same or different from each other. The method according to claim 1,
Wherein said formula 1 is selected from the following compounds:

. A first electrode; A second 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 comprises a heterocyclic compound according to any one of claims 1 to 7. Light emitting element. The method of claim 8,
Wherein the organic material layer includes a hole injection layer or a hole transport layer,
Wherein the hole injection layer or the hole transport layer comprises the heterocyclic compound of Formula 1. The method of claim 8,
Wherein the organic material layer includes an electron transport layer or an electron injection layer,
Wherein the electron transport layer or the electron injection layer comprises the heterocyclic compound of Formula 1. The method of claim 8,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the heterocyclic compound of Formula 1. The method of claim 11,
Wherein the light emitting layer further comprises a compound represented by Formula 2 below.
(2)

In Formula 2,
R9 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted heterocyclic group,
p is an integer of 0 to 6,
When p is 2 or more, the substituents in the parentheses are the same or different from each other,
L3 to L6, which may be the same or different, are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar 2 to Ar 5 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. [12] The compound according to claim 12, wherein L3 to L6 are the same or different from each other and each independently is a direct bond; Or an organic electroluminescent element selected from the following structures:

. The method of claim 12,
Ar 2 to Ar 5 are the same or different from each other and each independently hydrogen; Or an organic electroluminescent element selected from the following structures:

. The method of claim 11,
Wherein the light emitting layer further comprises a compound represented by the following formula (3).
(3)

In Formula 3,
R10 is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylheteroarylamine group; A substituted or unsubstituted arylphosphine group; Or a substituted or unsubstituted heterocyclic group,
q is an integer of 0 to 7,
When q is 2 or more, the substituents in the parentheses are the same or different from each other,
L7 to L9, which may be the same or different, are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar6 to Ar8 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. 16. The method of claim 15,
L7 to L9 are the same or different from each other and each independently represents a direct bond; Or an organic electroluminescent element selected from the following structures:

. 16. The method of claim 15,
Wherein Ar6 to Ar8 are the same or different from each other and each independently selected from among the following structures:

.

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