KR101941149B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a heterocyclic compound of formula (I) and an organic light emitting device including the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a heterocyclic compound and an organic light emitting device including the heterocyclic compound. [0002]

This application claims the benefit of Korean Patent Application No. 10-2016-0101360 filed on August 09, 2016, filed with the Korean Intellectual Property Office, 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.

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

Development of new materials for such organic light emitting devices has been continuously required.

U.S. Patent Application Publication No. 2004-0251816

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

According to one embodiment of the present disclosure, there is provided a heterocyclic compound represented by the following Formula 1:

[Chemical Formula 1]

In Formula 1,

R1 to R7 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; 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; Or a substituted or unsubstituted heteroaryl group, or R1 and R2 may be bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring , a is an integer of 0 to 3, b and c are each an integer of 0 to 4, d is an integer of 0 to 2, e is 0 or 1, and when a to d are each 2 or more, A + b + e? 7, c + d? 5,

Ar 1 to Ar 4 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl 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 heteroarylene group, and n and m are each an integer of 0 to 2, and when n is 2, L1 is the same or different and when m is 2, L2 is the same or different.

According to an embodiment of the present invention, there is also provided a plasma display panel 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 comprises a heterocyclic compound represented by Formula 1, to provide.

The heterocyclic compound according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device and by using it, it is possible to improve the efficiency, the driving voltage and / or the lifetime characteristics of the organic light emitting device.

1 shows an organic light emitting device 10 according to an embodiment of the present invention.
2 shows an organic light emitting element 11 according to another embodiment of the present invention.

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

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

In this specification, when a part is referred to as " including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

In this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; 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" means an aryl group substituted with an alkyl group, an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, an aryl group substituted with a silyl group, a heteroaryl group substituted with an alkyl group, A substituted heteroaryl group, a heteroaryl group substituted with a heteroaryl group, and the like.

In the present specification, the halogen group may be F, Cl, Br, I, or the like.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl group, N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 50 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but may have from 6 to 50 carbon atoms, and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, A naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group, a naphthyl group,

In the present specification, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom is an atom selected from the group consisting of N, P, O, S, Se, Ge and Si, Or more. The number of carbon atoms is not particularly limited, but is preferably 2 to 50 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 20 carbon atoms. The heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, A thiazolyl group, an acridyl group, an indoloacryidyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidyl group, A carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiophene group, a dibenzoyl group, a benzothiophene group, a benzothiophene group, A phenanthroline group, a phenothiazinyl group, an acenaphthoquinoxalyl group, an indenoquinazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, An indenoisoquinolyl group, an indenoquinolyl group, a pteridinyl group, a phenoxazinyl group, Quinazoline thiazolyl group, an indazolyl group, a quinolyl group MIDI benzo Perry, Perry benzo but include MIDI group, RY Loa acridine fluorenyl group, and the like.

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 50 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, But are not limited to, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, .

In this specification, the amine group is -NH ₂ ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 50. 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, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, Phenylnaphthylenediamine group, N-phenylphenylenediamine group, N-phenyltriphenylamine group, N-phenylphenanthrenylamine group, N-phenylphenanthrenylamine group, Group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group, but the present invention is not limited thereto.

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

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 heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group can be applied to the description of the above-mentioned heteroaryl group.

In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroaryl group.

In the present specification, the aryl group in the arylamine group, the aryloxy group, the aralkyl group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group and the alkylaryl group may be the description of the aryl group described above.

In the present specification, the alkyl group in the alkylamine group, alkylsilyl group, alkoxy group, aralkyl group, N-arylalkylamine group, alkylthio group, alkylsulfoxy group, N-alkylheteroarylamine group, The description of the alkyl group can be applied.

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

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 50. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

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

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

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등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group, the benzofluorenyl group, the spirobifluorenyl group, the spirobenzoanthracene fluorenyl group or the spiroacridine fluorenyl group is substituted,

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

In the present specification, examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethylphenoxy group, a 2,4,6- trimethylphenoxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1- Anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group and the like.

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 the present specification, the substituted or unsubstituted ring which can be formed in association with the adjacent group includes a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and the description of the above-mentioned cycloalkyl group or aryl group may be applied except that the hydrocarbon ring is not monovalent.

In this specification, the aromatic hydrocarbon ring may be monocyclic or polycyclic, and the description of the aryl group described above may be applied, except that it is not monovalent.

In the present specification, the hetero ring includes one or more atoms other than carbon, that is, a hetero atom. Specifically, the hetero atom includes an atom selected from the group consisting of N, P, O, S, Se, 1 or more. The heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and the description of the above-mentioned heteroaryl group may be applied except that it is not monovalent.

According to one embodiment of the present invention, the substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring which can be formed in combination with adjacent groups may be, for example, a substituted or unsubstituted fluorene ring and the like, no.

According to one embodiment of the present invention, the substituted or unsubstituted monocyclic or polycyclic aromatic heterocyclic ring which may be formed in combination with adjacent groups may be, for example, a substituted or unsubstituted indoloacridine ring or the like, But is not limited thereto.

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (2) or (3).

(2)

(3)

The substituents in the above formulas (2) and (3) are as defined in formula (1).

According to one embodiment of the present invention, the formula (2) or (3) may be represented by the following formula (4) or (5), respectively.

[Chemical Formula 4]

[Chemical Formula 5]

The substituents in the above formulas (4) and (5) are as defined in formula (1).

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (6).

[Chemical Formula 6]

In Formula 6,

R 8 and R 9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; 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; F and g are each an integer of 0 to 4, and when f and g are each 2 or more, the substituents in the parentheses are the same or different from each other,

X1 is a direct bond; NR; O; Or S, z is 0 or 1, z is 0, hydrogen is substituted for the carbon to which X1 is attached,

R is hydrogen; heavy hydrogen; A halogen group; Cyano; 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; Or a substituted or unsubstituted heteroaryl group,

And the remaining substituents are as defined in formula (1).

According to one embodiment of the present disclosure, R may be a phenyl group.

According to one embodiment of the present invention, the formula (6) may be represented by the following formula (7) or (8).

(7)

[Chemical Formula 8]

The substituents in the above formulas (7) and (8) are as defined in formula (6).

According to one embodiment of the present invention, the formula (7) or (8) may be represented by the following formula (9) or (10), respectively.

[Chemical Formula 9]

[Chemical formula 10]

The substituents in the above formulas (9) and (10) are as defined in formula (6).

According to one embodiment of the present disclosure, z is 0, and the carbon to which X1 is attached is substituted with hydrogen.

According to one embodiment of the present disclosure, R1 and R2 may be bonded to each other to form a substituted or unsubstituted fluorene ring.

According to one embodiment of the present disclosure, X1 is a direct bond and z is one.

According to one embodiment of the present invention, the formula (6) may be represented by any one of the following formulas (11) to (14).

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

The substituents of formulas (11) to (14) are as defined in formula (6).

According to one embodiment of the present disclosure, R1 and R2 may combine with each other to form a substituted or unsubstituted indoloacridine ring.

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (15).

[Chemical Formula 15]

In Formula 15,

R10 is hydrogen; heavy hydrogen; A halogen group; Cyano; 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; Or a substituted or unsubstituted heteroaryl group, h is an integer of 0 to 4, and when h is 2 or more, R10 is the same or different,

And the remaining substituents are the same as defined in formula (6).

According to one embodiment of the present invention, the formula (15) may be represented by the following formula (16) or (17).

[Chemical Formula 16]

[Chemical Formula 17]

The substituents in the above formulas (16) and (17) are as defined in formula (15).

According to one embodiment of the present invention, the formula (16) or (17) may be represented by the following formula (18) or (19), respectively.

[Chemical Formula 18]

[Chemical Formula 19]

The substituents in the above formulas (18) and (19) are as defined in formula (15).

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (20).

[Chemical Formula 20]

In Formula 20,

R11 is hydrogen; heavy hydrogen; A halogen group; Cyano; 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; Or a substituted or unsubstituted heteroaryl group, i is an integer of 0 to 5, and when i is 2 or more, R11 is the same or different,

And the remaining substituents are the same as defined in formula (6).

According to one embodiment of the present invention, the formula (20) may be represented by the following formula (21) or (22).

[Chemical Formula 21]

[Chemical Formula 22]

The substituents in the above formulas (21) and (22) are as defined in formula (20).

According to one embodiment of the present invention, the formula (21) or (22) may be represented by the following formula (23) or (24), respectively.

(23)

≪ EMI ID =

The substituents in the above formulas (23) and (24) are as defined in formula (20).

According to one embodiment of the present disclosure, L1 and L2 are the same or different and are each independently a direct bond; An arylene group substituted or unsubstituted with an alkyl group, a cycloalkyl group or an aryl group; Or a heteroarylene group substituted or unsubstituted with an alkyl group, a cycloalkyl group or an aryl group.

According to one embodiment of the present disclosure, L1 and L2 are the same or different and are each independently a direct bond; An arylene group having 6 to 50 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, or an aryl group having 6 to 50 carbon atoms; Or a heteroarylene group having 2 to 50 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, or an aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present disclosure, L1 and L2 are the same or different and are each independently a direct bond; A phenylene group; Naphthylene group; Biphenylene group; A terphenylrenylene group; A fluorenylene group substituted or unsubstituted with an alkyl group or an aryl group; Phenanthrylene group; Anthracenylene group; Thiophene group; A furanylene group; A pyrrolene group substituted or unsubstituted with an alkyl group or an aryl group; Dibenzofuranyl group; A dibenzothiophene group; Or a carbazolylene group substituted or unsubstituted with an alkyl group or an aryl group.

According to one embodiment of the present disclosure, L1 and L2 are the same or different and are each independently a direct bond; A phenylene group; Naphthylene group; Biphenylene group; A terphenylrenylene group; A fluorenylene group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms; Phenanthrylene group; Anthracenylene group; Thiophene group; A furanylene group; A pyrrolene group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms; Dibenzofuranyl group; A dibenzothiophene group; Or a carbazolylene group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present disclosure, L1 and L2 are the same or different and are each independently a direct bond; Or from the structural formulas in Table 1 below.

<Table 1>

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

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted pyrazine group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted pyridazine group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluoranthene group; A substituted or unsubstituted chrysene group; A substituted or unsubstituted pyrene group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinoxan group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted benzonaphthothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted fluorenobenzofurane group; A substituted or unsubstituted spirobifluorene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted isoquinol group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzoxathiol group; A substituted or unsubstituted pyrene group; Or a substituted or unsubstituted quinoxaline group.

According to one embodiment of the present invention, Ar1 to Ar4 may be the same or different and each independently represent one selected from the following structural formulas.

In the above formula,

R201 to R299 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl 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,

b3, b3, b3, b3, b3, b3, b3, b3, b3 and b3 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,

a3, a5, b5, b5, b5, b5, b6, a3, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9, b11 to b13, a22, a4, a7, a12, a15. When a19, a26, a27, a11, a13, a20 and a24 are each 2 or more, the substituents in the parentheses are different from each other.

In one embodiment of the present specification, R201 to R299 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl 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.

In another embodiment, R201 to R299 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted C1 to C30 alkoxy group; A substituted or unsubstituted silyl group; 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-C30 heteroaryl group.

In another embodiment, R201 to R299 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted 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 R299 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile 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 R299 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A methyloxy 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 naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted pyrrol group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted indole group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted cyclopentyl group; Or a substituted or unsubstituted cyclohexyl group.

According to another embodiment, R201 to R299 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A methyloxy group; A trimethylsilyl group; Methyl group; An ethyl group; Propyl group; Isopropyl group; t-butyl group; A phenyl group; Naphthyl group; A biphenyl group; A fluorene group substituted or unsubstituted with a methyl group or a phenyl group; A dibenzofurane group; A dibenzothiophene group; A substituted or unsubstituted phenyl group, a naphthyl group, a fluorene group substituted or unsubstituted with a methyl group, a methyl group, an ethyl group, or a carbazolyl group substituted or unsubstituted with a phenyl group, a dibenzofurane group, or a dibenzothiophene group Or an unsubstituted furan group; A substituted or unsubstituted phenyl group, a naphthyl group, a fluorene group substituted or unsubstituted with a methyl group, a methyl group, an ethyl group, or a carbazolyl group substituted or unsubstituted with a phenyl group, a dibenzofurane group, or a dibenzothiophene group Or an unsubstituted thiophene group; A substituted or unsubstituted phenyl group, a naphthyl group, a fluorene group substituted or unsubstituted with a methyl group, a methyl group, an ethyl group, or a carbazolyl group substituted or unsubstituted with a phenyl group, a dibenzofurane group, or a dibenzothiophene group Or an unsubstituted pyrrol group; A carbazole group substituted or unsubstituted with a phenyl group; Indole group; Benzofuran group; Benzothiophene group; A cyclopentyl group; Or a cyclohexyl group.

In another embodiment, R201 to R299 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A fluorine group; A trimethylsilyl group; Methyl group; An ethyl group; t-butyl group; A phenyl group; Or a biphenyl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and each independently represent a substituted or unsubstituted C 6 to C 8 alkyl group substituted with a halogen group, a cyano group, an alkoxy group, an alkyl group, a silyl group, An aryl group of 50; Or a heteroaryl group having 2 to 50 carbon atoms substituted or unsubstituted with a halogen group, a cyano group, an alkyl group, a cycloalkyl group, a silyl group, an aryl group or a heteroaryl group.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different and each independently represents a halogen group, a cyano group, an alkoxy group having 1 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, a silyl group, An aryl group having 6 to 50 carbon atoms which is unsubstituted or substituted with a heteroaryl group having 2 to 50 carbon atoms; Or a substituted or unsubstituted alkyl group having 2 to 50 carbon atoms which is substituted or unsubstituted with a halogen group, a cyano group, an alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, a silyl group, an aryl group having 6 to 50 carbon atoms or a heteroaryl group having 2 to 50 carbon atoms Lt; / RTI &gt;

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different from each other and each independently represents F, a cyano group, a methoxy group, a trifluoromethyl group, an alkyl group having 1 to 50 carbon atoms, a trimethylsilyl group, An aryl group having 6 to 50 carbon atoms which is unsubstituted or substituted with a heteroaryl group having 2 to 50 carbon atoms; Or a substituted or unsubstituted alkyl group having 2 to 50 carbon atoms which is unsubstituted or substituted with F, cyano, an alkyl group having 1 to 50 carbon atoms, a cyclopentyl group, a cyclohexyl group, a trimethylsilyl group, an aryl group having 6 to 50 carbon atoms or a heteroaryl group having 2 to 50 carbon atoms Lt; / RTI &gt;

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and each independently represents an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, a halogen group, a cyano group, a silyl group, a heteroaryl group, An aryl group having 6 to 50 carbon atoms which is unsubstituted or substituted with a substituent group; Or a heteroaryl group having 2 to 50 carbon atoms which is substituted or unsubstituted with a substituent consisting of an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, a halogen group, a cyano group, a silyl group, a heteroaryl group or a combination of two or more thereof.

According to one embodiment of the present invention, Ar 1 to Ar 4 are the same or different from each other and each independently represent an alkyl group, an aryl group, an alkoxy group, a halogen group, a cyano group, a silyl group, a heteroaryl group, A phenyl group substituted or unsubstituted with a substituent; A biphenyl group substituted or unsubstituted with an alkyl group, a halogen group, a cyano group or an alkylsilyl group; A terphenyl group substituted or unsubstituted with an alkyl group, a halogen group, a cyano group or an alkylsilyl group; A naphthyl group substituted or unsubstituted with an alkyl group, a halogen group, a cyano group or an alkylsilyl group; A fluorenyl group substituted or unsubstituted with an alkyl group, a halogen group, a cyano group, an alkylsilyl group or an aryl group; A benzofluorenyl group substituted or unsubstituted with an alkyl group; A phenanthrenyl group; Anthracenyl group; A dibenzofuranyl group substituted or unsubstituted with an alkyl group or a cycloalkyl group; A naphthobenzofuranyl group; A dibenzothiophene group substituted or unsubstituted with an alkyl group or a cycloalkyl group; A carbazolyl group substituted or unsubstituted with an alkyl group or an aryl group; An alkyl group, an aryl group, a heteroaryl group or a thiophene group substituted or unsubstituted with a substituent consisting of at least two of them; Quinolyl group; An isoquinolyl group; A pyridazinyl group; Triazinyl groups; A pyrimidinyl group; A pyridinyl group; Benzoxazolyl group; Benzothiazolyl group; Benzooxathiol groups; Pyrenyl; A fluoranthenyl group; A spirobifluorenyl group; A benzimidazolyl group substituted or unsubstituted with an alkyl group or an aryl group; A quinoxalinyl group; A dibenzofuranyl group condensed with a benzofuranyl group; Or a triphenylenyl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different and each independently represents an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, an alkoxy group having 1 to 50 carbon atoms, a halogen group, , An alkylsilyl group having 1 to 50 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms, or a phenyl group substituted or unsubstituted with a substituent consisting of 2 or more of these; A biphenyl group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms, a halogen group, a cyano group or an alkylsilyl group having 1 to 50 carbon atoms; A terphenyl group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms, a halogen group, a cyano group, or an alkylsilyl group having 1 to 50 carbon atoms; A naphthyl group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms, a halogen group, a cyano group or an alkylsilyl group having 1 to 50 carbon atoms; A fluorenyl group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms, a halogen group, a cyano group, an alkylsilyl group having 1 to 50 carbon atoms, or an aryl group having 6 to 50 carbon atoms; A benzofluorenyl group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms; A phenanthrenyl group; Anthracenyl group; A dibenzofuranyl group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or a cycloalkyl group having 3 to 50 carbon atoms; A naphthobenzofuranyl group; A dibenzothiophene group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or a cycloalkyl group having 3 to 50 carbon atoms; A carbazolyl group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms; A thiophene group substituted or unsubstituted with a substituent consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, a heteroaryl group having 2 to 50 carbon atoms, or a combination of two or more thereof; Quinolyl group; An isoquinolyl group; A pyridazinyl group; Triazinyl groups; A pyrimidinyl group; A pyridinyl group; Benzoxazolyl group; Benzothiazolyl group; Benzooxathiol groups; Pyrenyl; A fluoranthenyl group; A spirobifluorenyl group; A benzimidazolyl group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms; A quinoxalinyl group; A dibenzofuranyl group condensed with a benzofuranyl group; Or a triphenylenyl group.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other and each independently represents a methyl group, an isopropyl group, a tert-butyl group, an F, a nitrile group, a trimethylsilyl group, a phenyl group, a naphthyl group, A phenyl group substituted or unsubstituted with a substituent consisting of a thiophene group, a dimethylfluorene group, a dibenzofurane group, a dibenzothiophene group, a carbazole group, a benzofuran group, a benzothiophene group, or a combination of two or more of them; A biphenyl group substituted or unsubstituted with a substituent consisting of a methyl group, an isopropyl group, a tert-butyl group, an F, a nitrile group, a trimethylsilyl group, a phenyl group, a naphthyl group or a combination of two or more thereof; A terphenyl group substituted or unsubstituted with a substituent consisting of a methyl group, an isopropyl group, a tert-butyl group, an F, a nitrile group, a trimethylsilyl group, a phenyl group, a naphthyl group or a combination of two or more thereof; A naphthyl group substituted or unsubstituted with a substituent consisting of a methyl group, an isopropyl group, a tert-butyl group, an F, a nitrile group, a trimethylsilyl group, a phenyl group, a naphthyl group or a combination of two or more thereof; A substituted or unsubstituted benzoyl group, a substituted or unsubstituted benzoyl group, a substituted or unsubstituted benzoyl group, a substituted or unsubstituted benzoyl group, a substituted or unsubstituted benzyl group, a substituted or unsubstituted benzyl group, A thiophene group, or a fluorenyl group substituted or unsubstituted with a substituent consisting of at least two of them; A methyl group, an ethyl group, a phenyl group, or a benzofluorenyl group substituted or unsubstituted with a substituent consisting of at least two of them; A phenanthrenyl group; Anthracenyl group; A methyl group, an isopropyl group, a tert-butyl group, F, a nitrile group, a cyclohexyl group; A dibenzofuranyl group substituted or unsubstituted with a phenyl group; A naphthobenzofuranyl group; A methyl group, an isopropyl group, a tert-butyl group, F, a nitrile group, a cyclohexyl group; A dibenzothiophene group substituted or unsubstituted with a phenyl group; A methyl group, an ethyl group, a phenyl group, or a carbazolyl group substituted or unsubstituted with a substituent consisting of at least two of them; And examples thereof include a methyl group, ethyl group, isopropyl group, tert-butyl group, phenyl group, naphthyl group, furan group, thiophene group, dimethylfluorene group, dibenzofurane group, dibenzothiophene group, carbazole group, A thiophene group, or a thiophene group substituted or unsubstituted with a substituent consisting of at least two of them; Quinolyl group; An isoquinolyl group; A pyridazinyl group; Triazinyl groups; A pyrimidinyl group; A pyridinyl group; Benzoxazolyl group; Benzothiazolyl group; Benzooxathiol groups; Pyrenyl; A fluoranthenyl group; A spirobifluorenyl group; A methyl group, an ethyl group, a phenyl group, or a benzimidazolyl group substituted or unsubstituted with a substituent consisting of at least two of them; A quinoxalinyl group; Or a triphenylenyl group.

According to one embodiment of the present disclosure, Ar1 to Ar4 may be the same or different and each independently represent any one of the structural formulas shown in Table 2 below.

<Table 2>

과

가 서로 동일하다.According to one embodiment of the present disclosure,

and

Are the same.

과

가 서로 상이하다.According to one embodiment of the present disclosure,

and

Are different from each other.

According to one embodiment of the present disclosure, R 3 to R 10 are the same or different from each other, and each independently hydrogen; Or deuterium.

According to one embodiment of the present disclosure, R3 to R10 are hydrogen.

According to one embodiment of the present disclosure, R3 to R6 and R8 to R10 are hydrogen.

According to one embodiment of the present invention, the heterocyclic compound of Formula 1 may be represented by one of the following compounds.

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 an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or larger numbers of organic layers.

For example, 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 a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer.

2 shows a structure in which a first electrode 30, a hole injection layer 60, a hole transport layer 70, a light emitting layer 40, an electron transport layer 80, an electron injection layer 90 and a second electrode 50 are stacked in this order on a transparent substrate. 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

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, 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 layer includes a light emitting layer, and the light emitting layer includes a dopant and a host.

According to an embodiment of the present invention, the organic material layer includes a light emitting layer, the light emitting layer includes the heterocyclic compound, and the light emitting layer further comprises a host compound represented by the following Chemical Formula 20 or 21: In this case, the heterocyclic compound may be contained in an amount of 0.1 to 15% by weight, more preferably 1 to 10% by weight, more preferably 2 to 10% by weight, based on the total weight of the host and the dopant included in the light- By weight to 10% by weight, and more preferably from 2% by weight to 6% by weight.

According to one embodiment of the present invention, in the light emitting layer of the organic material layer, the heterocyclic compound may include 4% by weight based on the total weight of the host and the dopant in the light emitting layer.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer further includes a compound represented by the following formula (25).

(25)

In Formula 25,

R100 is hydrogen; heavy hydrogen; A halogen group; Cyano; 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; Or a substituted or unsubstituted heteroaryl group, x is an integer of 0 to 6, and when x is 2 or more, R100 is the same or different,

L11 to L14 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; O, p, q and r are each an integer of 1 or 2, and when o is 2, L11 is the same or different, and when p is 2, L12 is equal to or different from each other And when q is 2, L13 are the same or different from each other, and when r is 2, L14 are the same or different from each other,

Ar11 to Ar14 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R100 is selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

According to one embodiment of the present disclosure, R100 is hydrogen.

According to one embodiment of the present disclosure, L11 to L14 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms.

According to one embodiment of the present disclosure, L11 to L14 are the same or different and are each independently a direct bond; An alkyl group, or an arylene group substituted or unsubstituted with an aryl group; Or a heteroarylene group substituted or unsubstituted with an alkyl group or an aryl group.

According to one embodiment of the present disclosure, L11 to L14 are the same or different and are each independently a direct bond; An arylene group having 6 to 50 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms; Or an alkyl group having 1 to 50 carbon atoms or a heteroarylene group having 2 to 50 carbon atoms substituted or unsubstituted with an aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present invention, L11 to L14 are the same or different and each independently and independently of the other is a direct bond; A phenylene group; Naphthylene group; Biphenylene group; A terphenylrenylene group; An alkyl group, or a fluorenylene group substituted or unsubstituted with an aryl group; Phenanthrylene group; Anthracenylene group; Triphenylenylene group; A divalent thiophene group; A furanylene group; Dibenzofuranyl group; A divalent dibenzothiophene group; Or a carbazolylene group substituted or unsubstituted with an alkyl group or an aryl group.

According to one embodiment of the present disclosure, L11 to L14 are the same or different and are each independently a direct bond; A phenylene group; Naphthylene group; Biphenylene group; A terphenylrenylene group; A fluorenylene group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms; Phenanthrylene group; Anthracenylene group; Triphenylenylene group; A divalent thiophene group; A furanylene group; Dibenzofuranyl group; A divalent dibenzothiophene group; Or a carbazolylene group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present disclosure, L11 to L14 are the same or different and are each independently a direct bond; A phenylene group; Naphthylene group; Biphenylene group; A terphenylrenylene group; A fluorenylene group substituted or unsubstituted with a methyl group or a phenyl group; Phenanthrylene group; Anthracenylene group; Triphenylenylene group; A divalent thiophene group; A furanylene group; Dibenzofuranyl group; A divalent dibenzothiophene group; Or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

According to one embodiment of the present disclosure, L11 to L14 are the same or different and are each independently a direct bond; Or from the structural formulas in Table 3 below.

<Table 3>

According to one embodiment of the present disclosure, L11 is a direct bond.

According to one embodiment of the present disclosure, L13 is a phenylene group.

According to one embodiment of the present disclosure, L12 and L14 are direct bonds.

According to one embodiment of the present invention, Ar11 to Ar14 are the same or different and each independently represent a substituted or unsubstituted C6 to C50 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

According to one embodiment of the present invention, Ar11 to Ar14 are the same or different and each independently represents an aryl group having 6 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms substituted or unsubstituted with a heteroaryl group having 2 to 50 carbon atoms ; Or a heteroaryl group having 2 to 50 carbon atoms substituted or unsubstituted with an aryl group having 6 to 50 carbon atoms or a heteroaryl group having 2 to 50 carbon atoms.

According to one embodiment of the present invention, Ar11 to Ar14 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 one embodiment of the present invention, Ar11 to Ar14 are the same or different from each other and are each independently a phenyl group; 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 substituted or unsubstituted with an aryl 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.

According to one embodiment of the present invention, Ar11 to Ar14 are the same or different from each other and are each independently a phenyl group; 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 phenyl group, or a pyridyl group substituted or unsubstituted with 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.

According to one embodiment of the present invention, Ar11 to Ar14 may be the same or different and each independently represented by any one of the structural formulas shown in Table 4 below.

<Table 4>

According to one embodiment of the present invention, Ar11 and Ar13 are the same or different and are each independently a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted dibenzofurane group.

According to one embodiment of the present invention, Ar11 and Ar13 are the same or different and are each independently a naphthyl group; Or a dibenzofurane group.

According to one embodiment of the present disclosure, Ar11 is a 1-naphthyl group.

According to one embodiment of the present disclosure, Ar13 is a 2-naphthyl group.

According to one embodiment of the present disclosure, Ar11 is a 2-dibenzofurane group.

According to one embodiment of the present disclosure, Ar12 and Ar14 are hydrogen.

According to an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer further includes a compound represented by the following Chemical Formula 26:

(26)

In Formula 26,

R101 is hydrogen; heavy hydrogen; A halogen group; Cyano; 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; Or a substituted or unsubstituted heteroaryl group, y is an integer of 0 to 7, and when y is 2 or more, R 101 is the same or different,

L21 to L23 are the same or different, and are each independently a direct bond; A substituted or unsubstituted arylene group; And s, t and u are each an integer of 1 or 2, and when s is 2, L21 is the same or different, and when t is 2, L22 is the same or different from each other , and L23 when u is 2 are the same or different from each other,

Ar21 to Ar23 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R101 is hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

According to one embodiment of the present disclosure, R101 is hydrogen.

According to one embodiment of the present invention, L21 to L23 are the same or different from each other, and each independently is a direct bond; A substituted or unsubstituted arylene group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms.

According to one embodiment of the present invention, L21 to L23 are the same or different from each other, and each independently is a direct bond; An alkyl group, or an arylene group substituted or unsubstituted with an aryl group; Or a heteroarylene group substituted or unsubstituted with an alkyl group or an aryl group.

According to one embodiment of the present invention, L21 to L23 are the same or different from each other, and each independently is a direct bond; An arylene group having 6 to 50 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms; Or an alkyl group having 1 to 50 carbon atoms or a heteroarylene group having 2 to 50 carbon atoms substituted or unsubstituted with an aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present invention, L21 to L23 are the same or different from each other, and each independently and independently of the other is a direct bond; A phenylene group; Naphthylene group; Biphenylene group; A terphenylrenylene group; An alkyl group, or a fluorenylene group substituted or unsubstituted with an aryl group; Phenanthrylene group; Anthracenylene group; Triphenylenylene group; A divalent thiophene group; A furanylene group; Dibenzofuranyl group; A divalent dibenzothiophene group; Or a carbazolylene group substituted or unsubstituted with an alkyl group or an aryl group.

According to one embodiment of the present invention, L21 to L23 are the same or different from each other, and each independently is a direct bond; A phenylene group; Naphthylene group; Biphenylene group; A terphenylrenylene group; A fluorenylene group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms; Phenanthrylene group; Anthracenylene group; Triphenylenylene group; A divalent thiophene group; A furanylene group; Dibenzofuranyl group; A divalent dibenzothiophene group; Or a carbazolylene group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms or an aryl group having 6 to 50 carbon atoms.

According to one embodiment of the present invention, L21 to L23 are the same or different from each other, and each independently is a direct bond; A phenylene group; Naphthylene group; Biphenylene group; A terphenylrenylene group; A fluorenylene group substituted or unsubstituted with a methyl group or a phenyl group; Phenanthrylene group; Anthracenylene group; Triphenylenylene group; A divalent thiophene group; A furanylene group; Dibenzofuranyl group; A divalent dibenzothiophene group; Or a carbazolylene group substituted or unsubstituted with an ethyl group or a phenyl group.

According to one embodiment of the present invention, L21 to L23 are the same or different from each other, and each independently is a direct bond; Or from the structural formulas in Table 5 below.

<Table 5>

According to one embodiment of the present disclosure, L21 to L23 are direct bonds.

According to one embodiment of the present invention, Ar 21 to Ar 23 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

According to one embodiment of the present invention, Ar 21 to Ar 23 are the same or different and each independently represents an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms An aryl group having 6 to 50 carbon atoms; Or a heteroaryl group having 2 to 50 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms, or a heteroaryl group having 2 to 50 carbon atoms.

According to one embodiment of the present invention, Ar21 to Ar23 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 one embodiment of the present invention, Ar21 to Ar23 are the same or different from each other, and are each independently a phenyl group; 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 substituted or unsubstituted with an aryl 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.

According to one embodiment of the present invention, Ar21 to Ar23 are the same or different from each other, and are each independently a phenyl group; 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 phenyl group, or a pyridyl group substituted or unsubstituted with 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.

According to one embodiment of the present invention, Ar21 to Ar23 may be the same or different and each independently represented by any one of the structural formulas shown in Table 6 below.

<Table 6>

According to one embodiment of the present invention, Ar21 and Ar22 are the same or different and each independently a substituted or unsubstituted dibenzofurane group.

According to one embodiment of the present disclosure, Ar23 is a phenyl group.

According to one embodiment of the present disclosure, Ar21 and Ar22 are dibenzofurane groups.

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. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or larger numbers of organic layers.

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 disposed 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 includes a compound represented by Formula 25 or 26 as a host do. In addition, it may further include one or more organic layers selected from a hole transporting layer, a hole injecting layer, an electron transporting layer, and an electron injecting layer. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or larger numbers of organic layers.

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 may include a hole injecting layer or a hole transporting layer between the first electrode and the light emitting layer, And a layer simultaneously conducting electron injection. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or larger numbers of organic layers.

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 includes a compound represented by Formula 1 as a dopant, and a hole injecting layer or a hole transporting layer between the first electrode and the light emitting layer, And may include a layer that simultaneously performs electron transport and electron injection between the second electrode and the light emitting layer. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or larger numbers of organic layers.

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 includes a compound represented by Formula 1 as a dopant and a compound represented by Formula 25 or 26 as a host, A hole injecting layer or a hole transporting layer may be formed between the first electrode and the light emitting layer and a layer capable of electron transporting and electron injecting between the second electrode and the light emitting layer may be included, The layer at the same time may further include an n-type dopant. In this case, the n-type dopant material may be LiQ, but is not limited thereto.

According to one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer that simultaneously performs electron transport and electron injection may further include an n-type dopant in addition to the electron transporting material or electron injecting material, The weight ratio of the transport material or electron injecting material to the n-type dopant may be from 1: 100 to 100: 1. Specifically 1:10 to 10: 1. More specifically, it may be 1: 1.

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

As the negative electrode material, a material having a small work function is preferably used to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material usable in the present invention include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, ; 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 migration of an exciton to an electron injecting layer or an electron injecting material and is also excellent in a 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-hydroxyquinoline 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 compound represented by the above formula (25) or (26), 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 a heterocyclic compound, an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex represented by the formula (1). 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 or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an 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 Compound 1

1-1) Synthesis of intermediate 1-a

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

<Reaction Scheme 1>

2,3-b] benzofuran (30.0 g, 101 mmol), (3-formyldibenzo [b, d] furan-4- (29.0 g, 121 mmol) was completely dissolved in 1000 mL of tetrahydrofuran, and an aqueous solution of potassium carbonate (42 g, 303 mmol) , And tetrakis- (triphenylphosphine) palladium (5.8 g, 5.05 mmol) was added thereto. 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 and a nucleic acid to obtain intermediate 1-a (33.3 g, yield: 80%).

MS [M &lt; + &gt;] = 412.4

1-2) Synthesis of intermediate 1-b

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

<Reaction Scheme 2>

Sodium chlorite (7.3 g, 80 mmol) and sulfamic acid (9.9 g, 109.5 mmol) were diluted in water (80 mL each) after dissolving intermediate 1-a (30 g, 73 mmol) in 1000 mL of tetrahydrofuran 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 give intermediate 1-b (28.7 g, 92%).

MS [M &lt; + &gt;] = 428.4

1-3) Synthesis of intermediate 1-c

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

<Reaction Scheme 3>

Intermediate 1-b (28.7 g, 67.2 mmol) and methanesulfonic acid (500 mL) were added and the mixture was heated and stirred at 80 占 폚 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 give intermediate 1-c (26 g, 94%).

MS [M &lt; + &gt;] = 410.4

1-4) Synthesis of intermediate 1-d

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

<Reaction Scheme 4>

Intermediate 1-d (26 g, 63.2 mmol) was added to 500 mL of DMF and stirred. Bromine (21 g, 133 mmol) diluted in 50 mL of DMF was slowly added dropwise and stirred at room temperature for 24 hours. The resulting solid was filtered and washed with dichloromethane and hexane. The solid was recrystallized from toluene and hexane to give intermediate 1-d (27 g, 75%).

MS [M &lt; + &gt;] = 568.2

1-5) Synthesis of intermediate 1-e

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

<Reaction Scheme 5>

2-bromo-1,1'-biphenyl (10.2 g, 44 mmol) and 300 mL of tetrahydrofuran were placed in a nitrogen atmosphere and cooled to -78 ° C. N-butyl lithium (21 mL, 44 mmol) was added dropwise to the cooled reaction solution, which was then stirred for 1 hour. Then, Intermediate 1-d (25 g, 44 mmol) was added thereto and stirred 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 filter the solid. Acetic acid (300 mL) and 2 drops of sulfuric acid were added to the solid, followed by heating and stirring for 3 hours. After completion of the reaction, the solid was filtered, washed with water and ethanol, and recrystallized from ethyl acetate and toluene to obtain intermediate 1-e (23.2 g, 75%).

MS [M &lt; + &gt;] = 704.4

1-6) Synthesis of Compound 1

Compound 1 was synthesized according to Scheme 6 below.

<Reaction Scheme 6>

To a round bottom flask under nitrogen was added intermediate 1-e (6.0 g, 8.5 mmol), N - ([1,1'-biphenyl] -4-yl) dibenzo [b, d] furan- 4-yl) dibenzo [b, d] furan-4-amine (7.1 g, 21.3 mmol), sodium tert.butoxide (4.08 g, 42.5 mmol), bis (Tert-butylphosphine) palladium (0) (0.22 g, 0.4 mmol) were added to 120 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 separated and purified by column chromatography, and recrystallized from toluene and hexane to obtain Compound 1 (6.40 g, 62%).

MS [M &lt; + &gt;] = 1213.4

< Synthetic example  2> Synthesis of Compound 2

B] dibenzo [b, d] furan-2-amine (N - ([1,1'-biphenyl] -4-yl ) dibenzo [b, d] furan-2-amine) was used to synthesize Compound 2 according to 1-6 of Synthesis Example 1.

MS [M &lt; + &gt;] = 1213.4

< Synthetic example  3> Synthesis of Compound 3

Compound 3 was synthesized according to 1-6 of Synthesis Example 1 using Intermediate 1-e and 4- (tert-butyl) -N-phenylaniline.

MS [M &lt; + &gt;] = 993.2

< Synthetic example  4> Synthesis of Compound 4

Compound 4 was synthesized according to 1-6 of Synthesis Example 1 using Intermediate 1-e and bis (4- (tert-butyl) phenyl) amine.

MS [M &lt; + &gt;] = 1105.4

< Synthetic example  5> Synthesis of Compound 5

5-1) Synthesis of intermediate 5-a

Intermediate 5-a was synthesized according to Scheme 7 below.

<Reaction Scheme 7>

2,3-b] benzofuran (30.0 g, 101 mmol), (3-formyldibenzo [b, d] furan- (29.0 g, 121 mmol) was dissolved in 1000 mL of tetrahydrofuran. To the solution was added a solution of potassium carbonate (42 g, 303 mmol) in anhydrous tetrahydrofuran , And tetrakis- (triphenylphosphine) palladium (5.8 g, 5.05 mmol) was added thereto. 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 and hexane to obtain intermediate 5-a (30.8 g, yield: 74%).

MS [M &lt; + &gt;] = 412.4

5-2) Synthesis of intermediate 5-b

Intermediate 5-b was synthesized according to 1-2) 1-5) of Synthesis Example 1 using Intermediate 5-a.

MS [M &lt; + &gt;] = 704.2

5-3) Synthesis of Compound 5

1-6 of Synthesis Example 1 was obtained by using Intermediate 5-b and N- (4- (tert-butyl) phenyl) naphthalen-1 -amine (N- (4- (tert- ) Was synthesized.

MS [M &lt; + &gt;] = 1093.3

< Synthetic example  6> Synthesis of Compound 6

Dibenzo [b, d] furan-4-amine (N- (4- (tert-butyl) phenyl) dibenzo [ 4-amine) was used to synthesize Compound 6 according to 1-6 of Synthesis Example 1.

MS [M &lt; + &gt;] = 1173.4

< Synthetic example  7> Synthesis of Compound 7

Intermediate 5-b and N- (4- (tert-butyl) phenyl) -9,9-dimethyl-9H- dimethyl-9H-fluoren-1-amine) was used to synthesize Compound 7 according to 1-6 of Synthesis Example 1.

MS [M &lt; + &gt;] = 1225.5

< Synthetic example  8> Synthesis of Compound 8

Compound 8 was synthesized according to 1-6 of Synthesis Example 1 using intermediate 5-b and di-o-tolylamine.

MS [M &lt; + &gt;] = 937.1

< Synthetic example  9> Synthesis of Compound 9

9-1) Synthesis of intermediate 9-a

Intermediate 9-a was synthesized according to Reaction Scheme 8 below.

<Reaction Scheme 8>

9- (2-bromophenyl) -9H-carbazole (12.5 g, 38.7 mmol) and 300 mL of tetrahydrofuran were placed in a nitrogen atmosphere and cooled to -78 ° C. Respectively. N-butyl lithium (17 mL, 42.6 mmol) was added dropwise to the cooled reaction solution and stirred for 1 hour. Intermediate 5-c (20 g, 35 mmol) was then added and stirred 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 filter the solid. Acetic acid (300 mL) and 2 drops of sulfuric acid were added to the solid, followed by heating and stirring for 3 hours. After completion of the reaction, the solid was filtered off, washed with water and ethanol, and recrystallized from ethyl acetate and toluene to obtain intermediate 9-a (20 g, 72%).

MS [M &lt; + &gt;] = 793.5

9-2) Synthesis of Compound 9

Compound 9 was synthesized according to 1-6 of Synthesis Example 1 using intermediate 9-a and diphenylamine.

MS [M &lt; + &gt;] = 970.1

< Synthetic example  10> Synthesis of Compound 10

10-1) Synthesis of intermediate 10-a

Intermediate 10-a was synthesized following Synthesis Example 9-1) using Intermediate 1-d.

MS [M &lt; + &gt;] = 793.5

10-2) Synthesis of Compound 10

1-6 of Synthesis Example 1 was obtained by using the intermediate 10-a and N- (4- (tert-butyl) phenyl) naphthalene-2-amine (N- (4- (tert- butylphenyl) naphthalen- ) To synthesize Compound 10.

MS [M &lt; + &gt;] = 1182.4

< Synthetic example  11> Synthesis of Compound 11

11-1) Synthesis of intermediate 11-a

Intermediate 11-a was synthesized following Synthesis Example 9-1) using Intermediate 5-c and 2-bromo-N, N-diphenylaniline.

[Intermediate 11-a]

MS [M &lt; + &gt;] = 793.5

11-2) Synthesis of Compound 11

Compound 11 was synthesized according to 1-6 of Synthesis Example 1 using Intermediate 11-a and 2-fluoro-N- (o-tolyl) aniline.

MS [M &lt; + &gt;] = 1036.1

< Synthetic example  12> Synthesis of Compound 12

12-1) Synthesis of intermediate 12-a

Intermediate 12-a was synthesized following Synthesis Example 9-1) using Intermediate 1-d and 2-bromo-N, N-diphenylaniline.

MS [M &lt; + &gt;] = 795.5

12-2) Synthesis of Compound 12

Compound 12 was synthesized according to 1-6 of Synthesis Example 1 using intermediate 12-a and bis (4- (tert-butyl) phenyl) amine.

MS [M &lt; + &gt;] = 1196.5

< Example  1 > Preparation of organic light emitting device

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.

On the thus prepared ITO transparent electrode, the following compound HAT was thermally vacuum-deposited to a thickness of 50 Å to form a hole injection layer. Compound HT-A 1000 Å shown below was vacuum-deposited as a hole transporting layer, and 100 Å of the following compound HT-B was deposited thereon. The following compound H-A as a host and the following compound 1 of the present invention as a dopant were vacuum-deposited to a thickness of 200 Å in a thickness of 4% by weight as a host in the light emitting layer.

Then, 300 Å of the following compound ET-A and the following compound Liq were deposited in a ratio of 1: 1, followed by sequentially depositing magnesium (Mg) doped with 10 weight% of silver (Ag) To form a cathode, thereby preparing 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 the following compound 4 was used instead of the compound 1 in Example 1.

< Example  3>

An organic luminescent device was prepared in the same manner as in Example 1, except that the following compound 5 was used instead of the compound 1 in Example 1.

< Example  4>

An organic luminescent device was prepared in the same manner as in Example 1 except that Compound 8 was used instead of Compound 1 in Example 1.

< Example  5>

An organic luminescent device was prepared in the same manner as in Example 1, except that the following compound 10 was used instead of the compound 1 in Example 1.

< Example  6>

An organic luminescent device was produced in the same manner as in Example 1, except that the following compound 12 was used instead of the compound 1 in Example 1.

< Example  7>

An organic luminescent device was produced in the same manner as in Example 1, except that the following compound H-B was used instead of the compound H-A.

< Example  8>

An organic luminescent device was prepared in the same manner as in Example 2, except that the following compound H-B was used instead of the compound H-A.

< Example  9>

An organic luminescent device was prepared in the same manner as in Example 3, except that the following compound H-B was used instead of the compound H-A.

< Example  10>

An organic luminescent device was prepared in the same manner as in Example 4, except that the following compound H-B was used in place of the compound H-A in Example 4 above.

< Example  11>

An organic luminescent device was prepared in the same manner as in Example 5, except that the following compound H-B was used in place of the compound H-A in Example 5.

< Example  12>

An organic luminescent device was prepared in the same manner as in Example 6, except that the following compound H-B was used instead of the compound H-A.

< Example  13>

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

< Example  14>

An organic luminescent device was prepared in the same manner as in Example 2, except that the following compound H-C was used instead of the compound H-A.

< Example  15>

An organic luminescent device was produced in the same manner as in Example 3, except that the following compound H-C was used in place of the compound H-A in Example 3 above.

< Example  16>

An organic luminescent device was prepared in the same manner as in Example 4, except that the following compound H-C was used instead of the compound H-A.

< Example  17>

An organic luminescent device was prepared in the same manner as in Example 5, except that the following compound H-C was used instead of the compound H-A.

< Example  18>

An organic luminescent device was prepared in the same manner as in Example 6, except that the following compound H-C was used instead of the compound H-A in Example 6.

< Comparative Example  1>

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

< Comparative Example  3>

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

< Comparative Example  4>

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

< Comparative Example  5>

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

< Comparative Example  6>

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

The organic luminescent devices of Examples 1 to 18 and Comparative Examples 1 to 6 were measured for driving voltage, luminous efficiency and color coordinates at a current density of 10 mA / cm ² , and initial luminance at a current density of 20 mA / cm ² And the time (LT95) at which the contrast was 95% was measured. The results are shown in Table 7 below.

division Host Dopant @ 10mA / cm ² @ 20mA / cm ² Voltage (V) Efficiency (cd / A) CIE (x, y) Life (hr) Example 1 H-A Compound 1 4.5 5.02 (0.143, 0.042) 120 Example 2 H-A Compound 4 4.5 5.23 (0.141, 0.045) 130 Example 3 H-A Compound 5 4.4 5.33 (0.142, 0.042) 120 Example 4 H-A Compound 8 4.4 5.05 (0.142, 0.042) 135 Example 5 H-A Compound 10 4.4 4.89 (0.142, 0.054) 120 Example 6 H-A Compound 12 4.5 4.85 (0.142,0.055) 115 Example 7 H-B Compound 1 4.3 4.87 (0.142, 0.042) 130 Example 8 H-B Compound 4 4.2 5.14 (0.141, 0.043) 125 Example 9 H-B Compound 5 4.2 5.13 (0.141, 0.043) 115 Example 10 H-B Compound 8 4.4 4.98 (0.143, 0.042) 105 Example 11 H-B Compound 10 4.2 4.94 (0.141, 0.053) 110 Example 12 H-B Compound 12 4.2 4.98 (0.142, 0.054) 125 Example 13 H-C Compound 1 4.2 4.85 (0.143, 0.045) 125 Example 14 H-C Compound 4 4.2 5.05 (0.143, 0.042) 105 Example 15 H-C Compound 5 4.2 5.04 (0.141, 0.042) 120 Example 16 H-C Compound 8 4.0 4.82 (0.142,0.043) 125 Example 17 H-C Compound 10 4.1 4.66 (0.143, 0.052) 120 Example 18 H-C Compound 12 4.0 4.75 (0.142, 0.054) 125 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-B D-1 4.3 5.03 (0.143, 0.042) 80 Comparative Example 4 H-B D-2 4.2 3.61 (0.142, 0.044) 50 Comparative Example 5 H-C D-1 4.1 4.98 (0.144, 0.045) 80 Comparative Example 6 H-C D-2 4.2 3.66 (0.141, 0.044) 60

Comparing Examples 1 to 18 and Comparative Examples 1 to 6 of Table 7, the organic light emitting device including the heterocyclic compound represented by Formula 1 has a three-dimensional structure, Intermolecular fluorescence attenuation is prevented and excellent light emitting performance is exhibited. In addition, since dopant molecular core introduces Heteroaromatic substituted with oxygen which is higher in electronegativity than carbon, stable anion state is formed when one electron is obtained (anion condition), which leads to improvement of device life.

Therefore, it was confirmed that the compound of the present invention had excellent efficiency and lifetime characteristics as compared with the organic light emitting devices prepared in Comparative Examples 1 to 6 including a pyrene-based compound or a spirobifluorene-based compound.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

10, 11: Organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: Hole injection layer
70: hole transport layer
80: electron transport layer
90: electron injection layer

Claims (25)

A heterocyclic compound represented by the following formula 4 or 5:
[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas (4) and (5)
R3 to R6 are hydrogen,
R1 and R2 are bonded to each other to form a dihydroacridine ring substituted with a fluorene ring, an indoloacridine ring, or an aryl group,
a is 3, b and c are each 4,
Ar 1 to Ar 4 are the same or different and each independently represents a halogen group or an aryl group which is substituted or unsubstituted with an alkyl group; Or a heteroaryl group containing O,
L1 and L2 are direct bonds,
n and m are each 1. delete delete delete delete delete delete The heterocyclic compound according to claim 1, wherein the formula 4 or 5 is represented by the following formula 13 or 14:
[Chemical Formula 13]

[Chemical Formula 14]

The substituents in the above formulas (13) and (14) are as defined in the formula (4) or (5), R8 and R9 are hydrogen, and f and g are each 4. delete The heterocyclic compound according to claim 1, wherein the formula 4 or 5 is represented by the following formula 18 or 19:
[Chemical Formula 18]

[Chemical Formula 19]

The substituents in the above formulas (18) and (19) are as defined in the formula (4) or (5), R8 to R10 are hydrogen, f and h are respectively 4 and g is 3. delete The heterocyclic compound according to claim 1, wherein the formula 4 or 5 is represented by the following formula 23 or 24:
(23)

&Lt; EMI ID =

The substituents in the above formulas (23) and (24) are as defined in the formula (4) or (5), R8 to R11 are hydrogen, f and g are each 4 and i is 5. delete [2] The compound according to claim 1, wherein Ar1 to Ar4 are the same or different from each other and each independently represents an alkyl group having 1 to 50 carbon atoms, or a phenyl group substituted or unsubstituted with a halogen group; An alkyl group having 1 to 50 carbon atoms, or a biphenyl group substituted or unsubstituted with a halogen group; An alkyl group having 1 to 50 carbon atoms, or a terphenyl group substituted or unsubstituted with a halogen group; An alkyl group having 1 to 50 carbon atoms, or a naphthyl group substituted or unsubstituted with a halogen group; An alkyl group having 1 to 50 carbon atoms, or a fluorenyl group substituted or unsubstituted with a halogen group; A benzofluorenyl group substituted or unsubstituted with an alkyl group having 1 to 50 carbon atoms; A phenanthrenyl group; Anthracenyl group; A dibenzofuranyl group; A naphthobenzofuranyl group; Pyrenyl; A fluoranthenyl group; A spirobifluorenyl group; A dibenzofuranyl group condensed with a benzofuranyl group; Or a triphenylenyl group. The method according to claim 1,

and

Are the same as each other. The heterocyclic compound according to claim 1, wherein Ar1 to Ar4 are the same or different and each independently represents one selected from the following structural formulas:

In the above formula,
R201, R203 to R219, R258 to R267, R270 to R280 and R293 are hydrogen, an alkyl group, or a halogen group,
R226, R222, R230, R232, R234, R236, R268, R269, R281 to R292 and R294 to R295 are hydrogen,
a1, a6, and a10 are each an integer of 0 to 5,
a5, a8, a9, a14, a16, a17, a28, a30. a32, a34, b1, and b18 to b32 are each an integer of 0 to 4,
a3 is an integer of 0 to 7,
a4, a7, a12, a15. a19, a26 and an integer of 0 to 3,
a11 is an integer of 0 to 9,
a13 is an integer of 0 to 6,
a18 is an integer of 0 to 2,
When a18 is 2, the substituents in parentheses are different from each other,
a1, a5, a8, a9, a14, a16, a17, a28, a30, a32, a34, b1 and b18 to b32, a3, a4, a7, a12, a15. When a19, a26, a11, a13, and a24 are each 2 or more, the substituents in the parentheses are different from each other. The heterocyclic compound according to claim 1, wherein the compound represented by Formula 4 or 5 is represented by one of the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers is formed of any one of claims 1, 8, 10, 12, and 14 to 17 And a heterocyclic compound of one term. 19. The organic light emitting device according to claim 18, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the heterocyclic compound. 19. The organic light emitting device according to claim 18, wherein the organic material layer includes a hole injection layer, a hole transporting layer, or an electron blocking layer, and the hole injection layer, the hole transporting layer, or the electron blocking layer includes the heterocyclic compound. 19. The organic light emitting device according to claim 18, wherein the organic compound layer comprises 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. The organic electroluminescent device according to claim 19, wherein the light emitting layer further comprises a compound represented by the following general formula (25):
(25)

In Formula 25,
R &lt; 100 &gt; is hydrogen,
L11 is a direct bond,
L13 is an arylene group,
L12 and L14 are direct bonds,
o, p, q and r are each 1, x is 6,
Ar11 and Ar13 are the same or different and are each independently an aryl group; Or a heterocyclic group containing O,
Ar12 and Ar14 are hydrogen. 23. The method of claim 22, wherein L13 is selected from the structural formulas in Table 3 below,
Wherein Ar11 and Ar13 are the same or different and independently selected from the structural formulas shown in Table 4 below:
<Table 3>

<Table 4>

The organic electroluminescent device according to claim 19, wherein the light emitting layer further comprises a compound represented by Formula 26:
(26)

In Formula 26,
R101 is hydrogen,
L21 to L23 are direct bonds,
s, t and u are each 1,
Ar21 to Ar23 are the same or different and are each independently an aryl group; Or a heteroaryl group containing O. 27. The method of claim 24,
Wherein Ar 21 to Ar 23 are the same or different and independently selected from the structural formulas shown in Table 6 below:
<Table 6>

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