KR101835203B1 - Fused cyclic compound including nitrogen and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to a nitrogen-containing condensed ring compound and an organic light emitting device comprising the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a nitrogen-containing condensed ring compound and an organic light-

This application claims the benefit of the filing date of Korean Patent Application No. 10-2015-0036179 filed on March 16, 2015 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The present invention relates to a nitrogen-containing condensed ring compound and an organic light emitting device using the same.

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

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

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

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

Korean Patent Publication No. 2000-0051826

The present invention provides a nitrogen-containing condensed ring compound and an organic light emitting device using the same.

One embodiment of the present disclosure provides compounds represented by Formula 1:

[Chemical Formula 1]

In formula (1)

R ₁ to R ₁₈ , Ar ₁ and Ar ₂ are the same or different and each independently hydrogen; heavy hydrogen; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aromatic or aliphatic heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group,

L ₁ and L ₂ are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group, L ₁ may be combined with R ₁ or R ₁₈ to form a ring,

Provided that Ar ₁ and Ar ₂ Is represented by any one of the following formulas (A) to (D).

(A)

In the above formula (A)

Y ₁ is N or R ₂₀₁ , Y ₂ is N or R ₂₀₂ , Y ₃ is N or R ₂₀₃ , Y ₄ is N or R ₂₀₄ , Y ₅ is N or R ₂₀₅ , Y ₆ is N or R ₂₀₆ , Y ₇ is N or R ₂₀₇ ,

Any one of R ₂₀₁ to R ₂₀₇ is a moiety bonded to Formula 1 through L ₁ or L ₂ of Formula 1, and the remaining moieties are the same or different, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

[Chemical Formula B]

In the above formula (B)

And Y ₈ is N or R _208, Y ₉ is N or R _209, Y ₁₀ is N or R _210, Y ₁₁ is N or R _211, Y ₁₂ is N or R _212, Y ₁₃ is N or R ₂₁₃ , Y ₁₄ is N or R ₂₁₄ ,

Wherein any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to Formula 1 through L ₁ or L ₂ of Formula 1, and the remaining moieties are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,

≪ RTI ID = 0.0 &

In the above formula (C)

T ₁ is N or R ₃₀₉ , T ₂ is N or R ₃₁₀ ,

At least one of T ₁ and T ₂ is N,

Any one of R ₃₀₁ to R ₃₀₈ is a moiety bonded to Formula 1 through L ₁ or L ₂ of Formula 1, and the remaining R ₃₀₉ and R ₃₁₀ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or R ₃₀₁ and R ₃₀₂ are bonded to each other to form a ring substituted with R _c ,

When R ₃₀₁ and R ₃₀₂ are bonded to each other to form a ring substituted with R _c , any one of R ₃₀₃ to R ₃₀₈ and Rc may be bonded to L ₁ or L ₂ of formula (1) Lt; / RTI >

R _c is hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

[Chemical Formula D]

In the above formula (D)

And U ₁ is N or R _402, U ₂ is N or R _403, U ₃ is N, or R _404, U ₄ is N or R _405, U ₅ is N or R _406, U ₆ is N or R ₄₀₇ , U ₇ is N or R ₄₀₈ , U ₈ is N or R ₄₀₉ ,

Any one of R ₄₀₁ to R ₄₀₉ is a moiety bonded to the formula (1) through L ₁ or L ₂ of the formula (1), and the remaining moieties are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

Another embodiment of the present disclosure relates to a liquid crystal display comprising a first electrode; A second electrode facing the first electrode; And at least one organic compound layer including a light-emitting layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 Device.

The condensed ring compound according to the embodiments of the present disclosure has an appropriate energy level, and is excellent in electrochemical stability and thermal stability. Thus, the organic light emitting device comprising the compound provides high efficiency and / or high driving stability.

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

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

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

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

는 다른 치환기에 연결되는 부위를 의미한다. In this specification

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

As used herein, the term " substituted or unsubstituted " A nitrile group; An alkyl group; An alkenyl group; A cycloalkyl group; An aryl group; A heterocyclic group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkenylaryl group; An alkoxy group; An aryloxy group; An alkylamine group; Aralkylamine groups; An arylamine group; Alkylarylamine groups; Or a heteroarylamine group, or that at least two of the substituents exemplified above are substituted or unsubstituted with a substituent to which they are linked. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 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 cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the 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 boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 60 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

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

,

,

, 및

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

,

,

, And

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

In the present specification, the heterocyclic group is an aromatic or aliphatic heterocyclic group containing at least one of O, N and S as a hetero atom. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, A pyridazinyl group, a pyrazin group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, , A carbazole group, a carbazole group, a benzooxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, , An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, an acridine, and a dibenzofuranyl group, but is not limited thereto.

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

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

In the present specification, the alkylamine group, the aralkylamine group, the arylamine group, the alkylarylamine group, and the heteroarylamine group are amine groups substituted with an alkyl group, an aralkyl group, an aryl group, an alkylaryl group and a heteroaryl group, Here, the description of the alkyl and aryl groups described above may be applied to the alkyl and aryl, and the description of the heteroaryl group in the aforementioned heterocyclic group may apply to the aromatic heterocyclic group. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, 3-methyl- Methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group and the like But are not limited to these.

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

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the aromatic heterocyclic group described above can be applied except that each of these is 2 groups.

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

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

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

In the present specification, examples of the aromatic hydrocarbon ring include benzene ring, naphthalene ring, anthracene ring, and the like, but are not limited thereto.

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

As used herein, an aromatic heterocyclic ring means an aromatic ring containing at least one of N, O and S atoms as a hetero atom.

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

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

(2)

(3)

In Formulas (2) and (3), R ₁ to R ₁₈ , L ₂ , Ar ₁ and Ar ₂ are as defined in Formula (1)

R ₁₉ is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aromatic or aliphatic heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted alkylarylamine group; Or a substituted or unsubstituted heteroarylamine group or is bonded to adjacent substituents to form a ring, n is an integer of 1 to 4, p is an integer of 1 to 3, and when n or p is 2 or more, The groups are the same or different.

According to one embodiment of the present specification, R ₁₉ and Ar ₁ are bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present disclosure, R ₁₉ and Ar ₁ are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to one embodiment of the present disclosure, R ₁₉ and Ar ₁ are bonded to each other to form a substituted or unsubstituted benzene ring.

According to one embodiment of the present disclosure, R < ₁₉ > and Ar < ₁ > are bonded to each other to form a benzene ring.

According to one embodiment of the present invention, in Formula 1, L ₁ and L ₂ are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group.

According to one embodiment of the present invention, in Formula 1, L ₁ and L ₂ are the same or different and are each independently a direct bond; Or an arylene group.

According to one embodiment of the present invention, in Formula 1, L ₁ and L ₂ are the same or different and are each independently a direct bond; Or a phenylene group.

According to one embodiment of the present invention, at least one of Ar ₁ and Ar ₂ is represented by any one of formulas (A) to (D), and the remaining is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, at least one of Ar ₁ and Ar ₂ in Formula 1 is represented by any one of Formulas A to D, and the remainder is an aryl group substituted or unsubstituted with an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, at least one of Ar ₁ and Ar ₂ in Formula 1 is represented by any one of Formulas A to D, and the remaining is a phenyl group substituted or unsubstituted with an aryl group; A biphenyl group; Naphthyl group; A pyrimidyl group substituted or unsubstituted with an aryl group; Or a triazinyl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, at least one of Ar ₁ and Ar ₂ in Formula 1 is represented by any one of Formulas A to D, and the remainder is a phenyl group substituted or unsubstituted with a phenyl group; A biphenyl group; Naphthyl group; A pyrimidyl group substituted or unsubstituted with a phenyl group; Or a triazinyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present invention, the formula (A) is represented by any one of the following formulas (A-1) to (A-4).

[A-1]

[A-2]

[A-3]

[A-4]

In the above Formulas A-1 to A-4, the definitions of Y ₂ , Y ₃ , R ₂₀₁ and R ₂₀₄ to R ₂₀₇ are the same as in Formula A above.

According to one embodiment of the present invention, the formula (A) is represented by any one of the following formulas (A-5) to (A-12).

[A-5]

[A-6]

[A-7]

[A-8]

[A-9]

[A-10]

[A-11]

[A-12]

In Formulas A-5 to A-12, the definitions of R ₂₀₁ to R ₂₀₇ are the same as those of Formula A above.

According to one embodiment of the present invention, in formula (A), any one of R ₂₀₁ to R ₂₀₇ is a moiety bonded to formula (1) via L ₁ or L ₂ of formula (1) Each independently hydrogen; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, in formula (A), any one of R ₂₀₁ to R ₂₀₇ is a moiety bonded to formula (1) via L ₁ or L ₂ of formula (1) Each independently hydrogen; A nitrile group; An alkyl group; An aryl group substituted or unsubstituted with a phosphine oxide group substituted with an aryl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, in formula (A), any one of R ₂₀₁ to R ₂₀₇ is a moiety bonded to formula (1) via L ₁ or L ₂ of formula (1) Each independently hydrogen; A nitrile group; Methyl group; A phenyl group substituted or unsubstituted by a nitrile group, an aryl group, or a phosphine oxide group substituted with an aryl group; A biphenyl group substituted or unsubstituted with a nitrile group; Naphthyl group; A fluorenyl group substituted or unsubstituted with an alkyl group; A pyridyl group; A carbazolyl group substituted or unsubstituted with an aryl group; Benzocarbazolyl group; A dibenzofuranyl group; Or a dibenzothiophene group.

According to one embodiment of the present invention, in formula (A), any one of R ₂₀₁ to R ₂₀₇ is a moiety bonded to formula (1) via L ₁ or L ₂ of formula (1) Each independently hydrogen; A nitrile group; Methyl group; A phenyl group substituted or unsubstituted with a nitrile group, a phenyl group, a diphenylphosphine oxide group, or a phenylnaphthylphosphine oxide group; A biphenyl group substituted or unsubstituted with a nitrile group; Naphthyl group; A fluorenyl group substituted or unsubstituted with a methyl group; A pyridyl group; A carbazolyl group substituted or unsubstituted with a phenyl group; Benzocarbazolyl group; A dibenzofuranyl group; Or a dibenzothiophene group.

According to one embodiment of the present invention, the formula (A) is represented by any one of the following formulas (A-13) to (A-15).

[A-13]

[Chemical formula A-14]

[A-15]

In the above formulas A-13 to A-15, the definitions of R ₂₀₁ to R ₂₀₇ are the same as those of the above formula A,

Q ₁ is a direct bond; C (-O); Or CR _a R _b ,

R ₂₂₀ to R ₂₂₂ , R _a and R _b are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r220 and r221 are each an integer of 1 to 4,

r222 is an integer of 1 to 3,

When r220 to r222 are respectively 2 or more, the structures in parentheses of 2 or more are equal to or different from each other.

According to one embodiment of the present invention, the formula (A-13) is represented by any one of the following formulas (A-16) to (A-18).

[A-16]

[A-17]

[A-18]

In the above formulas A-16 to A-18, the definitions of R ₂₀₁ , R ₂₀₅ to R ₂₀₇ , R ₂₂₀ , r ₂₂₀ , R _a and R _b are the same as those of the above formula A-12.

And R ₂₂₀ to R ₂₂₂ are hydrogen.

R _a and R _b are methyl groups.

According to one embodiment of the present invention, the formula (B) is represented by any one of the following formulas (B-1) to (B-4).

[Formula B-1]

[Formula B-2]

[Formula B-3]

[Formula B-4]

In the above Formulas B-1 to B-4, the definitions of Y ₈ and R ₂₀₉ to R ₂₁₄ are the same as those of Formula B above.

According to one embodiment of the present invention, the formula (B) is represented by any one of the following formulas (B-5) to (B-7).

[Formula B-5]

[Formula B-6]

[Formula B-7]

In Formulas B-5 to B-7, the definitions of R ₂₀₉ to R ₂₁₄ are the same as those of Formula B above.

According to one embodiment of the present invention, in Formula B, any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to Formula 1 through L ₁ or L ₂ in Formula 1, and the remaining moieties are the same or different from each other Each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, in Formula B, any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to Formula 1 through L ₁ or L ₂ in Formula 1, and the remaining moieties are the same or different from each other Each independently hydrogen; An aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, in Formula B, any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to Formula 1 through L ₁ or L ₂ in Formula 1, and the remaining moieties are the same or different from each other Each independently hydrogen; A phenyl group substituted or unsubstituted with an aryl group; A biphenyl group; Naphthyl group; A fluorenyl group substituted or unsubstituted with an alkyl group; A carbazolyl group substituted or unsubstituted with an aryl group; A dibenzofuranyl group; Or a dibenzothiophene group.

According to one embodiment of the present invention, in Formula B, any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to Formula 1 through L ₁ or L ₂ in Formula 1, and the remaining moieties are the same or different from each other Each independently hydrogen; A phenyl group substituted or unsubstituted with a phenyl group; A biphenyl group; Naphthyl group; A fluorenyl group substituted or unsubstituted with a methyl group; A carbazolyl group substituted or unsubstituted with a phenyl group; A dibenzofuranyl group; Or a dibenzothiophene group.

According to one embodiment of the present invention, the formula (C) is represented by the following formula (C-1).

[Chemical formula C-1]

In the above formula (C-1)

Any one of R ₃₀₁ to R ₃₀₈ is a moiety bonded to the formula (1) via L ₁ or L ₂ of the formula (1), and the remaining moieties are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, the formula (C) is represented by the following formula (C-2).

[Chemical formula C-2]

In the above formula (C-2)

Any one of R ₃₀₁ to R ₃₀₈ and R ₃₁₁ to R ₃₁₄ is a moiety bonded to the formula (1) via L ₁ or L ₂ in the formula (1), and the others are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, in any one of formulas C-1 and C-2, any one of R ₃₀₁ to R ₃₁₄ is a moiety bonded to Formula 1 through L ₁ or L ₂ of Formula 1 , And the remainder is hydrogen.

According to one embodiment of the present invention, the formula (D) is represented by the following formula (D-1).

[Formula D-1]

In formula (D-1), the definitions of U ₁ to U ₄ , R ₄₀₁ and R ₄₀₆ to R ₄₀₉ are the same as those of formula (D).

According to one embodiment of the present invention, the formula (D) is represented by any one of the following formulas (D-2) to (D-6).

[Formula D-2]

[Formula D-3]

[Formula D-4]

[Formula D-5]

[Formula D-6]

In Formulas D-2 to D-6, the definitions of R ₄₀₁ to R ₄₀₉ are the same as those of Formula D above.

According to one embodiment of the present invention, in Formula D, any one of R ₄₀₁ to R ₄₀₉ is a moiety bonded to Formula 1 through L ₁ or L ₂ of Formula 1, and the remaining moieties are the same or different from each other Each independently hydrogen; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, in Formula D, any one of R ₄₀₁ to R ₄₀₉ is a moiety bonded to Formula 1 through L ₁ or L ₂ of Formula 1, and the remaining moieties are the same or different from each other Each independently hydrogen; Or an aryl group substituted or unsubstituted with a nitrile group.

According to one embodiment of the present invention, in Formula D, any one of R ₄₀₁ to R ₄₀₉ is a moiety bonded to Formula 1 through L ₁ or L ₂ of Formula 1, and the remaining moieties are the same or different from each other Each independently hydrogen; Or a phenyl group substituted or unsubstituted with a nitrile group.

According to one embodiment of the present invention, the above formula (1) can be represented by the following structural formulas.

Another embodiment of the present invention provides an organic light emitting device comprising a compound represented by Formula 1 above.

An organic light emitting device according to an embodiment of the present invention includes a first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of the above formula (1).

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

In another embodiment, the organic material layer includes an electron transporting layer, an electron injecting layer, a layer which simultaneously transports electrons and electrons, a light emitting layer, a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes, The electron transporting layer, the electron injecting layer, the layer that simultaneously transports electrons and injects electrons, the light emitting layer, the hole transporting layer, the hole injecting layer, or the layer that simultaneously transports holes and injects holes includes the compound of Formula 1.

According to one embodiment of the present invention, the organic material layer includes an electron transporting layer, an electron injecting layer, or a layer simultaneously performing electron transporting and electron injection, and the electron transporting layer, the electron injecting layer, The compound of formula (1).

In one embodiment of the present invention, the light emitting layer comprises the compound of Formula 1.

In one embodiment of the present invention, the light emitting layer includes the compound of Formula 1 as a host.

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

In one embodiment of the present invention, the organic material layer may further include a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group or a benzocarbazole group in addition to the organic material layer containing the compound of Formula 1 .

In one embodiment of the present invention, the organic compound layer containing the compound of Formula 1 includes the compound of Formula 1 as a host, and may include other organic compounds, metals, or metal compounds as a dopant.

The dopant may be at least one selected from the following compounds, but is not limited thereto.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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

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

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

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

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

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

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

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

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

Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.

The compound represented by the formula (1) according to the present specification can be prepared by a multistage chemical reaction. The preparation of these compounds is described by the following preparations.

The compound represented by the formula (1) can be prepared according to the following reaction scheme 1-1, scheme 1-2, and scheme 1-3, respectively, and compounds corresponding to the formula 1, formula 2 and formula 3 can be prepared. Although it is not limited to the same reaction, the reaction scheme is briefly described for the sake of understanding.

<General Production Example>

Scheme 1-1. Preparation of Formula (1)

1) Preparation of Formula b

2) Preparation of core structure of formula (1)

Scheme 1-2. Preparation of core structure of formula (2)

Scheme 1-3. Preparation of core structure of formula (3)

In the above Reaction Schemes 1-1 to 1-3, L ₁ , L ₂ , Ar ₁ and Ar ₂ have the same definitions as in Formula 1, and X, X 1 and X 2 each independently represent a halogen group. L ₁ , L ₂ , Ar ₁ and Ar ₂ are modified using Suzuki couling, Buckwald-Hartwig couling, Heck couling, Ullmann reaction or the like in Schemes 1-1 to 1-3, Can be prepared in various ways.

Synthesis Example 1. Synthesis of Compound b

1) Synthesis of compound a

141.7 g (849.1 mmol, 1.1 eq) of 2- (nitrophenyl) boronic acid and 200.0 g (771.9 mmol, 1.0 eq) of 4-bromo-9H- fluoren- It is dissolved in 1.9 L of THF and stirred. Next, 213.4 g (1543.8 mmol, 2.0 eq) of K ₂ CO ₃ was dissolved in 600 ml of water and 21.97 g (3.9 mmol, 0.005 eq) of Pd (t-Bu ₃ P) _{2 was} added thereto and the mixture was refluxed and stirred. After 2 hours, when the reaction was completed, the organic layer was separated, and the solvent was removed by decompression. The residue was completely dissolved in chloroform and washed with water. The solvent was removed under reduced pressure, and 195.4 g (648.4 mmol, yield 84%) of Compound (a) was obtained by column chromatography.

2) Synthesis of compound b

195.4 g (466.8 mmol, 1.0 eq) of the compound a was dissolved in 600 ml of triethylphosphite (P (OEt) ₃ ), and the mixture was refluxed and stirred. After 3 hours, the reaction was cooled, and the solvent was removed by vacuum decompression. This was completely dissolved in chloroform and washed with water. The solvent was then removed under reduced pressure, and 125.7 g (466.8 mmol, yield 72%) of Compound b was obtained by column chromatography.

Synthesis Example 2. Synthesis of Compound 2-b

1) Synthesis of Compound 2-a

60.0.0 g (185.1 mmol, 1.0 eq) of 2-bromo-N, N-diphenylaniline was dissolved in 500 mL of anhydrous tetrahydrofuran and then cooled to -78 ° C. 123.3 mL (308.4 mmol, 1.0 eq) of n-butyllithium (2.5 M) was slowly added to the cooled solution and stirred at the same temperature for 30 minutes. Compound (b) (49.8 g, 185.1 mmol, 1.0 eq) was added to the cooled mixture. When the reaction was completed, the mixture was warmed to room temperature, and a saturated aqueous ammonium chloride solution was added and stirred. The mixture was extracted with ethyl acetate, which was treated with anhydrous magnesium sulfate, filtered and concentrated. An excessive amount of hexane and a small amount of ethyl acetate were added to the concentrated compound, followed by stirring and filtration to obtain 80.9 g (157.3 mmol, yield 85%) of the compound 2-a.

2) Synthesis of compound 2-b

80.9 g (157.3 mmol, 1.0 eq) of the compound 2-a was diluted with 500 mL of acetic acid, followed by addition of 2 mL of concentrated sulfuric acid, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, the solid was filtered, washed with ethanol and water in turn. The filtered solid was dissolved in chloroform and neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was separated, washed with water and separated, treated with anhydrous magnesium sulfate, filtered, and purified by recrystallization with addition of ethyl acetate. The purified solid was filtered to obtain 68.7 g (yield: 88%) of a white compound 2-b.

MS: [M + H] &lt; ⁺ &gt; = 497

Synthesis Example 3. Synthesis of Compound 3-b

1) Synthesis of Compound 3-a

60.0 g (186.2 mmol, 1.0 eq) of 9- (2-bromophenyl) -9H-carbazole was dissolved in 500 mL of THF and cooled to -78. 123.3 mL (308.4 mmol, 1.0 eq) of n-butyllithium (2.5 M) was slowly added to the cooled solution and stirred at the same temperature for 30 minutes. 50.1 g (186.2 mmol, 1.0 eq) of compound b was added to the cooled mixture. When the reaction was completed, the mixture was warmed to room temperature, and a saturated aqueous ammonium chloride solution was added and stirred. The mixture was extracted with ethyl acetate, which was treated with anhydrous magnesium sulfate, filtered and concentrated. An excessive amount of hexane and a small amount of ethyl acetate were added to the concentrated compound, followed by stirring and filtration to obtain 83.4 g (162.0 mmol, yield 87%) of the compound 3-a.

2) Synthesis of compound 3-b

83.4 g (162.0 mmol, 1.0 eq) of Compound 3-a was diluted in 500 mL of acetic acid, followed by addition of 2 mL of concentrated sulfuric acid, and the mixture was stirred under reflux for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, the solid was filtered, washed with ethanol and water in turn. The filtered solid was dissolved in chloroform and neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was separated, washed with water and separated, treated with anhydrous magnesium sulfate, filtered, and purified by recrystallization with addition of ethyl acetate. The purified solid was filtered to obtain 70.0 g (yield: 87%) of a white compound 3-b.

MS: [M + H] &lt; ⁺ &gt; = 495

Synthesis Example 4. Synthesis of Compound 4

Compound 2-b 10.0 g (20.1 mmol , 1.0 eq), 4-chloro-2-phenylquinazoline 5.33 g (22.2 mmol, 1.1 eq), K 3 PO 4 8.6 g (40.27 mmol, 2.0 eq), Pd (t-Bu ₃ P) ₂ of 0.05 g (0.10 mmol, 0.005 eq ) and stirred under reflux and dissolved in 50 ml of xylene (xylene). When the reaction was completed, the solvent was removed by decompression. Then, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 11.9 g (17.1 mmol, yield 85%) of Compound 4.

MS: [M + H] &lt; ⁺ &gt; = 701

Synthesis Example 5. Synthesis of Compound 5

5.88 g (22.15 mmol, 1.1 eq) of K ₂ PO _4, 8.6 g (40.27 mmol, 2.0 eq) of K ₃ PO ₄ , 10.0 g (20.1 mmol, 1.0 eq) of compound 2-b, 4- (2-chloroquinazolin- 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ was dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Then, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 11.9 g (16.5 mmol, yield 82%) of Compound 5.

MS: [M + H] &lt; ⁺ &gt; = 726

Synthesis Example 6. Synthesis of Compound 6

Compound 2-b 10.0 g (20.1 mmol , 1.0 eq), 2-chloro-3-phenylquinoxaline 5.3 g (22.2 mmol, 1.1 eq), K 3 PO 4 8.6 g (40.27 mmol, 2.0 eq), Pd (t-Bu ₃ P) ₂ of 0.05 g (0.10 mmol, 0.005 eq ) and stirred under reflux and dissolved in 50 ml of xylene (xylene). When the reaction was completed, the solvent was removed by decompression. After that, it was completely dissolved in chloroform and washed with water. The solvent was then removed under reduced pressure to obtain 10.7 g (15.3 mmol, yield 76%) of Compound 6.

MS: [M + H] &lt; ⁺ &gt; = 701

Synthesis Example 7: Synthesis of Compound 7

Compound 2-b 10.0 g (20.1 mmol , 1.0 eq), 2-chloro-4- (naphthalen-2-yl) quinazoline 6.4 g (22.2 mmol, 1.1 eq), K 3 PO 4 8.6 g (40.27 mmol, 2.0 eq ) And 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 13.2 g (17.5 mmol, yield 87%) of Compound 7.

MS: [M + H] &lt; ⁺ &gt; = 751

Synthesis Example 8. Synthesis of Compound 8

8.9 g (22.2 mmol, 1.1 eq.) Of K ₂ PO _4, 8.6 g (2.9 mmol) of K ₂ PO ₄ , and 10.0 g (20.1 mmol, 1.0 eq) of 2- 40.27 mmol, 2.0 eq) and 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Then, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The product was subjected to column chromatography to obtain 14.8 g (17.1 mmol, yield 85%) of Compound 8.

MS: [M + H] &lt; ⁺ &gt; = 866

Synthesis Example 9 Synthesis of Compound 9

Compound 2-b 10.0 g (20.1 mmol , 1.0 eq), 4- (4-chloroquinazolin-2-yl) benzonitrile 5.9 g (22.2 mmol, 1.1 eq), K 3 PO 4 8.6 g (40.27 mmol, 2.0 eq), 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ was dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The product was subjected to column chromatography to obtain 11.8 g (16.3 mmol, yield 81%) of Compound 9.

MS: [M + H] &lt; ⁺ &gt; = 726

Synthesis Example 10. Synthesis of Compound 10

5.4 g (22.2 mmol, 1.1 eq) of K ₃ PO _4, 8.6 g (40.27 mmol, 2.0 eq) of 3-chloro-2-phenylpyrido [ eq) and 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Then, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting product was subjected to column chromatography to obtain 10.3 g (14.7 mmol, yield 73%) of Compound 10.

MS: [M + H] &lt; ⁺ &gt; = 702

Synthesis Example 11. Synthesis of Compound 11

8.6 g (40.27 mmol, 2.0 eq) of K ₃ PO ₄ , 7.4 g (22.2 mmol, 1.1 eq) of 9-bromoacenaphtho [1,2- b] quinoxaline, 10.0 g (20.1 mmol, 1.0 eq) 0.05 g (0.10 mmol, 0.005 eq) of (t-Bu ₃ P) ₂ was dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Then, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 13.3 g (17.7 mmol, yield 88%) of Compound 11.

MS: [M + H] &lt; ⁺ &gt; = 749

Synthesis Example 12. Synthesis of Compound 12

8.6 g (40.27 mmol, 2.0 eq) of K ₃ PO ₄ , 7.4 g (22.2 mmol, 1.1 eq) of 3-bromoacenaphtho [1,2-b] quinoxaline, 10.0 g (20.1 mmol, 1.0 eq) 0.05 g (0.10 mmol, 0.005 eq) of (t-Bu ₃ P) ₂ was dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. After that, it was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting product was subjected to column chromatography to obtain 12.8 g (17.1 mmol, yield 85%) of Compound 12.

MS: [M + H] &lt; ⁺ &gt; = 749

Synthesis Example 13. Synthesis of Compound 13

6.5 g (22.2 mmol, 1.1 eq) of 1-chloro-4- (naphthalen-2-yl) phthalazine and 8.6 g (40.27 mmol, 2.0 eq) of K ₃ PO _{4 were added to} 10.0 g (20.1 mmol, 1.0 eq) ) And 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 12.3 g (16.3 mmol, yield 81%) of Compound 13.

MS: [M + H] &lt; ⁺ &gt; = 749

Synthesis Example 14. Synthesis of Compound 14

Compound 3-b 10.0 g (20.1 mmol , 1.0 eq), 9- (2-chloroquinazolin-4-yl) -9Hcarbazole 7.3 g (22.2 mmol, 1.1 eq), K 3 PO 4 8.6 g (40.27 mmol, 2.0 eq) And 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Then, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain Compound 14 (10.9 g, 13.9 mmol, yield 69%).

MS: [M + H] &lt; ⁺ &gt; = 788

Synthesis Example 15. Synthesis of Compound 15

Compound 3-b 10.0 g (20.1 mmol , 1.0 eq), 2-chloro-4-phenylquinazoline 7.3 g (22.2 mmol, 1.1 eq), K 3 PO 4 8.6 g (40.27 mmol, 2.0 eq), Pd (t-Bu ₃ P) ₂ of 0.05 g (0.10 mmol, 0.005 eq ) and stirred under reflux and dissolved in 50 ml of xylene (xylene). When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting product was subjected to column chromatography to obtain 12.3 g (17.5 mmol, yield 87%) of Compound 15.

MS: [M + H] &lt; ⁺ &gt; = 699

Synthesis Example 16. Synthesis of Compound 16

A solution of 7.0 g (22.2 mmol, 1.1 eq) of K ₂ PO _4, 8.6 g (10 mmol) of compound 3-b (10.1 g, 20.1 mmol, 1.0 eq) (40.27 mmol, 2.0 eq) and 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 13.6 g (17.5 mmol, yield 87%) of Compound 16.

MS: [M + H] &lt; ⁺ &gt; = 775

Synthesis Example 17. Synthesis of Compound 17

A solution of 9.0 g (22.2 mmol, 1.1 eq) of K ₃ PO _4, 8.6 g (1.9 mmol) of 3- (2-chloroquinazolin-4-yl) -9- 40.27 mmol, 2.0 eq) and 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 15.2 g (17.6 mmol, yield 87%) of Compound 17.

MS: [M + H] &lt; ⁺ &gt; = 864

Synthesis Example 18. Synthesis of Compound 18

Compound 3-b 10.0 g (20.1 mmol , 1.0 eq), 6-bromo-9-phenyl-9H-pyrido [2,3-b] indole 7.2 g (22.2 mmol, 1.1 eq), K 3 PO 4 8.6 g ( 40.27 mmol, 2.0 eq) and 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. After that, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The product was subjected to column chromatography to obtain 13.3 g (17.9 mmol, yield 89%) of Compound 18.

MS: [M + H] &lt; ⁺ &gt; = 737

Synthesis Example 19. Synthesis of Compound 19

7.2 g (22.2 mmol, 1.1 eq.) Of K ₃ PO _4, 8.6 g (1.9 mmol) of compound 3-b, 10.0 g (20.1 mmol, 1.0 eq.) Of 6-bromo-9- 40.27 mmol, 2.0 eq) and 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 12.9 g (17.6 mmol, yield 87%) of Compound 19.

MS: [M + H] &lt; ⁺ &gt; = 737

Synthesis Example 20: Synthesis of Compound 20

Compound 3-b 10.0 g (20.1 mmol , 1.0 eq), 1-chloro-4-phenylphthalazine 4.9 g (22.2 mmol, 1.1 eq), K 3 PO 4 8.6 g (40.27 mmol, 2.0 eq), Pd (t-Bu ₃ P) ₂ of 0.05 g (0.10 mmol, 0.005 eq ) and stirred under reflux and dissolved in 50 ml of xylene (xylene). When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The product was subjected to column chromatography to obtain 12.0 g (17.2 mmol, yield 85%) of Compound 20.

MS: [M + H] &lt; ⁺ &gt; = 699

Synthesis Example 21. Synthesis of Compound 21

Compound 3-b 10.0 g (20.1 mmol , 1.0 eq), 2- (4-bromophenyl) -4-phenylpyrido [2,3-d] pyrimidine 7.3 g (22.2 mmol, 1.1 eq), K 3 PO 4 8.6 g ( 40.27 mmol, 2.0 eq) and 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 50 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. After that, it was completely dissolved in chloroform and washed with water. The solvent was then removed under reduced pressure, and the resulting product was subjected to column chromatography to obtain 13.3 g (17.1 mmol, yield 83%) of Compound 21.

MS: [M + H] &lt; ⁺ &gt; = 776

Synthesis Example 22. Synthesis of Compound 22

1) Synthesis of Compound 22-a

2-bromo-N-phenylaniline 20.0 g (20.1 mmol, 1.0 eq), 4-bromo-1,1'-biphenyl 20.7 g (22.2 mmol, 1.1 eq), K 3 PO 4 34.2 g (161.2 mmol, 2.0 eq) And 0.21 g (0.40 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 200 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and then decompressed to remove the solvent. The resulting product was subjected to column chromatography to obtain 27.4 g (68.5 mmol, yield 85%) of the compound 22-a.

2) Synthesis of compound 22-b

Except for using Compound 22-a instead of 2-bromo-N, N-diphenylaniline in Synthesis Example 2, the following Compound 22-b was synthesized.

3) Synthesis of Compound 22

Compound 22-b 20.00 g (20.1 mmol , 1.0 eq), 2-chloro-4-phenylquinazoline 5.16 g (22.2 mmol, 1.1 eq), K 3 PO 4 7.4 g (34.9 mmol, 2.0 eq), Pd (t-Bu ₃ P) ₂ (0.04 mmol, 0.005 eq) were dissolved in 50 ml of xylene and refluxed with stirring. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in chloroform, washed with water, and again reduced in pressure to remove the solvent. The resulting product was subjected to column chromatography to obtain 10.71 g (13.7 mmol, yield 79%) of Compound 22.

MS: [M + H] &lt; ⁺ &gt; = 777

&Lt; Experimental Examples 1 to 9 &

Compounds prepared in Synthesis Examples were subjected to high purity sublimation purification by a conventionally known method, and red organic light emitting devices were prepared in the following manner. 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.

After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 ^-6 torr, and then an organic material was coated on the ITO using DNTPD (700), α-NPB (300 Å), Compound 4 , Dp-6 (5 wt%) as a dopant was co-deposited (300 Å), and Alq ₃ (6 wt%) was used as a host 350 Å), LiF (5 Å), and Al (1,000 Å). 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 to 7 Å / sec.

&Lt; Comparative Example 1 &

The organic luminescent device of Comparative Example 1 was the same as the host of the luminescent layer in the organic luminescent device structures of Experimental Examples 1 to 9 except that CBP which is widely used as a general phosphorescent host material was used instead of the compound prepared by the synthesis example of the present specification Respectively.

The driving voltage, the current efficiency, the lifetime and the color coordinates were measured for the organic light emitting devices manufactured according to Experimental Examples 1 to 9 and Comparative Example 1, and the results are shown in Table 1 below.

compound Driving voltage
(V) Current efficiency
(cd / A) life span
(T95 @ 10mA) x coordinate y coordinate Experimental Example 1 4 4.27 21.96 153 0.664 0.327 Experimental Example 2 6 4.21 24.04 168 0.670 0.329 Experimental Example 3 7 4.01 24.83 227 0.672 0.331 Experimental Example 4 11 4.39 20.50 136 0.660 0.335 Experimental Example 5 14 4.21 23.45 192 0.668 0.330 Experimental Example 6 15 4.17 24.02 210 0.673 0.327 Experimental Example 7 16 4.41 21.04 168 0.663 0.327 Experimental Example 8 17 4.23 23.21 196 0.664 0.329 Experimental Example 9 20 4.21 24.41 146 0.663 0.330 Comparative Example 1 CBP 7.51 13.05 57 0.657 0.325

Experimental Examples 1 to 9 according to one embodiment of the present invention were confirmed to emit red light. The organic electroluminescent device of the comparative example using CBP showed lower driving voltage, higher current efficiency, superior lifetime Performance. &Lt; / RTI &gt; 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 embodiments, but many variations and modifications may be made to the electron blocking layer, This also falls within the scope of the invention.

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

Claims (11)

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

In formula (1)
R ₁ to R ₁₈ are hydrogen,
L ₁ and L ₂ are the same or different and are each independently a direct bond; Or an arylene group, L &lt; ₁ &gt; may combine with R &lt; _{1 &gt;} or R &lt; ₁₈ &gt;
At least one of Ar ₁ and Ar ₂ is represented by any one of the following formulas A to D and the remaining is an aryl group substituted or unsubstituted with an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group,
(A)

In the above formula (A)
Y ₁ is N or R ₂₀₁ , Y ₂ is N or R ₂₀₂ , Y ₃ is N or R ₂₀₃ , Y ₄ is N or R ₂₀₄ , Y ₅ is N or R ₂₀₅ , Y ₆ is N or R ₂₀₆ , Y ₇ is N or R ₂₀₇ ,
Wherein any one of R ₂₀₁ to R ₂₀₇ is bonded to L ₁ or L ₂ of Formula 1, and the other is hydrogen; A nitrile group; An alkyl group; An aryl group substituted or unsubstituted with a phosphine oxide group substituted with an aryl group or an aryl group; Or a heteroaryl group which is substituted or unsubstituted with an aryl group or is bonded to an adjacent group to form a ring substituted or unsubstituted with a methyl group or C (= O)
[Chemical Formula B]

In the above formula (B)
And Y ₈ is N or R _208, Y ₉ is N or R _209, Y ₁₀ is N or R _210, Y ₁₁ is N or R _211, Y ₁₂ is N or R _212, Y ₁₃ is N or R ₂₁₃ , Y ₁₄ is N or R ₂₁₄ ,
Wherein any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to Formula 1 via L ₁ or L ₂ in Formula 1, and the remaining is hydrogen; An aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group,
&Lt; RTI ID = 0.0 &

In the above formula (C)
T ₁ is N or R ₃₀₉ , T ₂ is N or R ₃₁₀ ,
At least one of T ₁ and T ₂ is N,
Any one of R ₃₀₁ to R ₃₀₈ is a moiety bonded to Formula 1 through L ₁ or L ₂ of Formula 1, and the remaining R ₃₀₉ and R ₃₁₀ are hydrogen, or R ₃₀₁ and R ₃₀₂ are bonded to each other To form a benzene ring substituted with R &lt; _c &
When said R ₃₀₁ and R ₃₀₂ form a benzene ring substituted by R _c combine with each other, any one of R ₃₀₃ to R _308, and R _c is through the L ₁ or L ₂ in the formula (1), the formula (1) May be the site to be joined,
R &lt; _c &gt; is hydrogen,
[Chemical Formula D]

In the above formula (D)
And U ₁ is N or R _402, U ₂ is N or R _403, U ₃ is N, or R _404, U ₄ is N or R _405, U ₅ is N or R _406, U ₆ is N or R ₄₀₇ , U ₇ is N or R ₄₀₈ , U ₈ is N or R ₄₀₉ ,
Any one of R ₄₀₁ to R ₄₀₉ is a moiety bonded to the formula (1) through L ₁ or L ₂ of the formula (1), and the remaining moieties are the same or different and each independently hydrogen; Or an aryl group substituted or unsubstituted with a nitrile group. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or 3:
(2)

(3)

In Formulas (2) and (3), R ₁ to R ₁₈ , L ₂ , Ar ₁ and Ar ₂ are as defined in Formula (1)
R ₁₉ is hydrogen, n is an integer of 1 to 4, p is an integer of 1 to 3, and when n or p is 2 or more, the groups in the parentheses are the same or different. The compound according to claim 1, wherein the formula (A) is represented by any one of the following formulas (A-1) to (A-4)
[A-1]

[A-2]

[A-3]

[A-4]

In the above Formulas A-1 to A-4, the definitions of Y ₂ , Y ₃ , R ₂₀₁ and R ₂₀₄ to R ₂₀₇ are the same as in Formula A above. The compound according to claim 1, wherein the formula (B) is represented by any one of the following formulas (B-2) to (B-4)
[Formula B-1]

[Formula B-2]

[Formula B-3]

[Formula B-4]

In the above Formulas B-1 to B-4, the definitions of Y ₈ and R ₂₀₉ to R ₂₁₄ are the same as those of Formula B above. The compound according to claim 1, wherein the formula (C) is represented by the following formula (C-1):
[Chemical formula C-1]

In the above formula (C-1)
Any one of R ₃₀₁ to R ₃₀₈ is a moiety bonded to the general formula (1) via L ₁ or L ₂ in the general formula (1), and the other is hydrogen. The compound according to claim 1, wherein the formula (C) is represented by the following formula (C-2):
[Chemical formula C-2]

In the above formula (C-2)
Any one of R ₃₀₁ to R ₃₀₈ and R ₃₁₁ to R ₃₁₄ is a moiety bonded to Formula 1 via L ₁ or L ₂ in Formula 1 and the remaining is hydrogen. The compound according to claim 1, wherein the formula (D) is represented by the following formula (D-1):
[Formula D-1]

In formula (D-1), the definitions of U ₁ to U ₄ , R ₄₀₁ and R ₄₀₆ to R ₄₀₉ are the same as those of formula (D). The compound according to claim 1, wherein the compound of formula (1) is represented by the following structural formula:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer including a light-emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 8 Lt; / RTI &gt; The organic electroluminescent device according to claim 9, wherein the organic material layer includes an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, a light emitting layer, a hole transport layer, a hole injection layer, , The electron injection layer, the layer that simultaneously performs electron transport and electron injection, the light emitting layer, the hole transport layer, the hole injection layer, or the layer that simultaneously transports holes and injects holes. The organic light emitting device according to claim 9, wherein the light emitting layer comprises the compound.

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