KR101773670B1 - Fused cyclic compound including nitrogen and organic light emitting device using the same - Google Patents

Abstract

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

Description

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

This application claims priority to Korean Patent Application No. 10-2014-0119113 filed on September 5, 2014, and Korean Patent Application No. 10-2015-0036949 filed on March 17, 2015 The 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 injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting 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 ₉ and R ₁₀ are bonded to each other to form a ring, or R ₁₀ and R ₁₁ and a bond to form a ring, or combination of R ₁₁ and R ₁₂ form a ring with each other, the formed ring is a substituent (R _{20) m} / RTI >

m is an integer of 1 to 4, and when m is 2 or more, R ₂₀ are the same or different from each other,

R ₉ to R ₁₂ of the group does not form a ring, R ₁ to R _8, R ₁₃ to R _18, R _20, Ar ₁ and Ar ₂ are the same as or different from each other, 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, or is bonded to adjacent substituents to form a ring,

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, and L ₁ may combine with R ₁ or R ₁₈ to form a ring.

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 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 is the same as that of the above-mentioned 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 above-mentioned 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 a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.

As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more of the N, O, 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, at least one of Ar ₁ and Ar ₂ in Formula 1 is represented by one of the following Formulas A to D, but is not limited thereto.

(A)

In formula (A)

Y ₁ to Y ₃ are the same or different and are each independently N or CRd,

R ₂₀₁ and R _d are the same or different from each other, 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 or is bonded to adjacent substituents to form a ring.

[Chemical Formula B]

In formula (B)

T ₁ and T ₂ are the same or different and are each independently N or CRe,

R ₃₀₀ to R ₃₀₅ and Re are the same or different from each other 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, or is bonded to adjacent substituents to form a ring, n is 1 or 2,

When n is 2, R ₃₀₅ are the same or different from each other.

≪ RTI ID = 0.0 &

In formula (C)

U ₁ to U ₈ are the same or different and each independently N or CRf,

L ₃ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Rf are the same or different from each other, 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 or is bonded to adjacent substituents to form a ring.

[Chemical Formula D]

In Formula D, one of U ₉ and U ₁₀ is N and the remainder is CRg,

L ₄ is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Rg, _R321 and _R322 are the same or different from each other, 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, or is bonded to adjacent substituents to form a ring, and q is an integer of 1 to 5.

According to another embodiment of the present invention, the formula (1) may be represented by one of the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In formulas (2) to (4), R ₁ to R ₁₈ , R ₂₀ , m, L ₁ , L ₂ , Ar ₁ and Ar ₂ are as defined in formula (1).

According to another embodiment of the present invention, the formula (1) may be represented by one of the following formulas (5) to (7).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In Formulas 5 to 7, R ₁ to R ₁₈ , R ₂₀ , m, 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, and when n is 2 or more, R ₁₉ is the same or different.

According to another embodiment of the present invention, the formula (1) may be represented by one of the following formulas (8) to (10).

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

Wherein R ₁ to R ₁₈ , R ₂₀ , m, 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, p is an integer of 1 to 3, and when p is 2 or more, R ₁₉ is the same or different.

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 a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

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 monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

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; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene 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; A phenylene group; Biphenylene group; Or a naphthylene group.

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

[Formula A-1] [Formula A-2]

[Chemical formula A-3] [Chemical formula A-4]

In the above Formulas A-1 to A-4,

R ₁₉₈ to R ₂₀₁ are the same or different from each other, 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present invention, the formula (A) may be represented by the following formula (A-5).

[A-5]

In formula (A-5), Y ₁ and Y ₂ are as defined in formula (A)

Z ₁ to Z ₄ are the same or different and are each independently N or CRc,

Rc are the same or different and are each independently selected from the group consisting of 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present invention, the formula (A-5) may be represented by one of the following formulas (A-6) to (A-9).

[A-6]

[A-7]

[A-8]

[A-9]

In Formulas A-6 to A-9,

Y ₁ and Y ₂ are as defined in formula (A)

Q is a direct bond, C (= O), or CRhRi,

R ₂₀₂ to R ₂₀₅ , R ₂₁₀ to R ₂₁₆ , Rh and R 1 are the same or different from each other, 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present invention, the formula (A-5) may be represented by the following formula (A-10) or (A-11).

[A-10]

[A-11]

In Formulas A-10 and A-11,

R ₂₀₂ to R ₂₀₇ are the same or different from each other, 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present invention, the formula (A-5) may be represented by the following formula (A-12) or (A-13).

[A-12]

[A-13]

In Formulas A-12 and A-13,

R ₂₀₂ to R ₂₀₅ , R ₂₀₈ and R ₂₀₉ are the same or different from each other, 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present invention, the formula (A-9) may be represented by one of the following formulas (A-14) to (A-16).

[Chemical formula A-14]

[A-15]

[A-16]

In Formulas A-14 to A-16,

R ₂₁₀ to R ₂₁₈ are the same or different from each other 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 or is bonded to adjacent substituents to form a ring.

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

[Formula B-1]

In the formula (B-1)

T ₁ and T ₂ are as defined in formula (B)

R ₃₀₀ to R ₃₀₆ are the same or different from each other, 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present invention, the formula (B) may be represented by one of the following formulas (B-2) to (B-4).

[Formula B-2]

[Formula B-3]

[Formula B-4]

In Formulas B-2 to B-4,

R ₃₀₀ to R ₃₁₂ 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present disclosure, at least one of U ₁ to U ₈ of the above formula (C) is N.

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

[Chemical formula C-1]

In formula (C-1)

U ₁ to U ₄ and L ₃ are as defined in formula (C)

R ₃₁₂ to R ₃₁₅ are the same or different from each other 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 or is bonded to adjacent substituents to form a ring.

According to one embodiment of the present invention, at least one of U ₁ to U ₄ in the above formula (C) is N.

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

[Chemical formula C-2]

[Formula C-3]

In Formulas C-2 and C-3,

L ₃ is as defined in formula (C)

R ₃₁₂ to R ₃₁₉ 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 or is bonded to adjacent substituents to form a ring.

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

[Chemical formula C-4]

[Chemical formula C-5]

In Formulas C-4 and C-5,

U ₁ to U ₄ are as defined in formula (C)

R ₃₁₂ to R ₃₁₅ and R ₃₂₀ are the same or different from each other, 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, or is bonded to adjacent substituents to form a ring, and q is an integer of 1 to 4;

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

[Formula D-1]

[Formula D-2]

Substituents of formulas D-1 and D-2 are as defined in formula (D).

According to one embodiment of the present disclosure, R ₃₂₂ in formula (D) is a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, R ₃₂₂ in the above formula (D) is a phenyl group substituted or unsubstituted with a nitrile group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group; Or one of the above-mentioned formulas (A) to (D).

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; A substituted or unsubstituted arylamine group; Or one of the above-mentioned formulas (A) to (D).

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted phenanthrolinyl group; A substituted or unsubstituted benzoquinolyl group; A substituted or unsubstituted diphenylamine group; Or one of the above-mentioned formulas (A) to (D).

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a phenyl group; A biphenyl group; A terphenyl group; Naphthyl group; A phenanthrenyl group; A fluorenyl group; A carbazolyl group; A phenanthrolinyl group; Benzoquinolyl group; Diphenylamine group; Or one of the above-mentioned formulas (A) to (D)

Ar 1 and Ar 2 may be substituted or unsubstituted with at least one member selected from the group consisting of a nitrile group, an alkyl group and an aryl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a phenyl group; A biphenyl group; A terphenyl group; Naphthyl group; A phenanthrenyl group; A fluorenyl group; A carbazolyl group; A phenanthrolinyl group; Benzoquinolyl group; Diphenylamine group; Or one of the above-mentioned formulas (A) to (D)

Ar 1 and Ar 2 may be substituted or unsubstituted with at least one member selected from the group consisting of a nitrile group, a methyl group, a phenyl group, a biphenyl group and a naphthyl group.

According to one embodiment of the present invention, in the general formulas (1) to (10), Ar ₂ is represented by one of the above formulas (A) to (D).

According to one embodiment of the present invention, in the above Formulas 1 to 10, Ar ₁ is represented by one of the above formulas A to D.

According to one embodiment of the present invention, in the general formulas (1) to (10), Ar ₁ represents hydrogen; Or a substituted or unsubstituted aryl group, and Ar ₂ is represented by one of the above formulas (A) to (D).

According to one embodiment of the present invention, in the above Chemical Formulas 1 to 10, Ar ₁ is represented by one of the above Chemical Formulas A to D, Ar ₂ is hydrogen; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, in the general formulas (1) to (10), Ar ₁ and Ar ₂ are the same or different and each independently represents one of the above formulas (A) to (D).

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted phenanthrolinyl group; A substituted or unsubstituted benzoquinolyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted pyrimidyl; A substituted or unsubstituted thiazinyl group; Or a group represented by the following formula.

는 연결기 L₁ 또는 L₂를 통하여 화학식 1에 연결되는 부위이며, 상기 구조는 니트릴기, 알킬기 또는 아릴기로 치환 또는 비치환될 수 있다. In the above structure,

Is a moiety connected to the formula (1) via a linking group L ₁ or L ₂ , and the structure may be substituted or unsubstituted with a nitrile group, an alkyl group or an aryl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a phenyl group; A biphenyl group; A substituted or unsubstituted terphenyl group; Naphthyl group; A phenanthrenyl group; A fluorenyl group; A carbazolyl group; A phenanthrolinyl group; Benzoquinolyl group; Diphenylamine group; A pyridyl group; Pyrimidyl; Triazinyl groups; Or a group represented by the formula:

Ar 1 and Ar 2 may be substituted or unsubstituted with at least one member selected from the group consisting of a nitrile group, a methyl group, a phenyl group, a biphenyl group and a naphthyl group.

는 연결기 L₁ 또는 L₂를 통하여 화학식 1에 연결되는 부위이며, 상기 구조는 니트릴기, 알킬기 또는 아릴기로 치환 또는 비치환될 수 있다.In the above structure,

Is a moiety connected to the formula (1) via a linking group L ₁ or L ₂ , and the structure may be substituted or unsubstituted with a nitrile group, an alkyl group or an aryl group.

According to one embodiment of the present invention, at least one of Ar ₁ and Ar ₂ is a substituted or unsubstituted pyridyl group selected from the group consisting of a nitrile group, an alkyl group and an aryl group; A pyrimidyl group substituted or unsubstituted with at least one member selected from the group consisting of a nitrile group, an alkyl group and an aryl group; A triazinyl group substituted or unsubstituted with at least one member selected from the group consisting of a nitrile group, an alkyl group and an aryl group; Or a group represented by the following formula.

는 연결기 L₁ 또는 L₂를 통하여 화학식 1에 연결되는 부위이며, 상기 구조는 니트릴기, 알킬기 또는 아릴기로 치환 또는 비치환될 수 있다.In the above structure,

Is a moiety connected to the formula (1) via a linking group L ₁ or L ₂ , and the structure may be substituted or unsubstituted with a nitrile group, an alkyl group or an aryl group.

According to one embodiment of the present invention, at least one of Ar ₁ and Ar ₂ is a pyridyl group; A pyrimidyl group substituted or unsubstituted with at least one member selected from the group consisting of a nitrile group, a phenyl group and a biphenyl group; A triazinyl group substituted or unsubstituted with at least one member selected from the group consisting of a nitrile group, a phenyl group, a biphenyl group and a naphthyl group; Or a group represented by the following formula.

는 연결기 L₁ 또는 L₂를 통하여 화학식 1에 연결되는 부위이며, 상기 구조는 니트릴기, 알킬기 또는 아릴기로 치환 또는 비치환될 수 있다.In the above structure,

Is a moiety connected to the formula (1) via a linking group L ₁ or L ₂ , and the structure may be substituted or unsubstituted with a nitrile group, an alkyl group or an aryl group.

According to one embodiment of the present invention, the formula (1) may be represented by the following structural formulas, but is not limited thereto.

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.

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

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.

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 material 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 having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

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

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

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

Hereinafter, the present invention will be described in 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 produced by a multistage chemical reaction. The preparation of these compounds is described by the following preparations.

The compound represented by the formula (1) may be prepared by a method and a procedure similar to the following reaction schemes 1-1 to 1-9, respectively. The reaction scheme is briefly described for the sake of understanding.

<Production Example>

Scheme 1-1. Preparation of Formula 2

1) Preparation of formula a

2) Preparation of formula 2

Scheme 1-2. Preparation of Formula 3

Scheme 1-3. Preparation of 4

Scheme 1-4. Preparation of Formula 5

1) Preparation of Formula b

2) Preparation of compound of formula 5

Scheme 1-5. Preparation of 6

Scheme 1-6. Preparation of Formula 7

Scheme 1-7. Preparation of 8

1) Preparation of formula c

2) Preparation of compound of formula 8

Scheme 1-8. Preparation of 9

Scheme 1-9. Preparation of Formula 10

In the above Reaction Schemes 1-1 to 1-9, L ₁ , L ₂ , Ar ₁ and Ar ₂ have the same definitions as in Formula 1, and L ₁ , L ₂ , Ar ₁ and Ar ₂ are modified, 10 can be prepared in various ways.

Synthesis Example 1 Synthesis of Compound X-4

1) Synthesis of Compound X-1

120.0 g (370 mmol, 1.0 eq) of 2-bromo-N, N-diphenylaniline was dissolved in 900 mL of anhydrous tetrahydrofuran and cooled to -78 ° C. 148.0 mL (370 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. 95.9 g (370 mmol, 1.0 eq) of 4-bromo-9H-fluoren-9-one 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. To the concentrated compound was added an excess amount of hexane and a small amount of ethyl acetate, followed by stirring and filtration to obtain 156.8 g (yield: 84%) of the formula X-1.

2) Synthesis of compound X-2

156.8 g (310.8 mmol, 1.0 eq) of Compound X-1 was diluted in 700 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 131.5 g (yield: 87%) of a white compound X-2.

3) Synthesis of Compound X-3

A solution of 131.5 g (270.3 mmol, 1.0 eq) of compound X-2, 48.0 g (270.3 mmol, 1.0 eq) of 1-chloronaphthalen-2-amine and 77.9 g (811.0 mmol, 3 eq) of sodium tert-butoxide ) And 0.69 g (1.3 mmol, 0.005 eq) of Pd ( t- Bu ₃ P) ₂ were dissolved in 650 ml of xylene and refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the solution was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 127.7 g (yield: 81%) of compound X-3.

4) Synthesis of Compound X-4

Formula X-3 127.7 g (218.9 mmol , 1.0 eq) Pd (t -Bu 3 P) in _{2 0.56 g (1.09 mmol, 0.005} eq), K 2 CO 3 90.8 g (656.9 mmol, 3.0 eq) with 550 mL DMF And the reaction was carried out. The reaction solution was stirred at 150 ° C for 12 hours, and then the solvent was concentrated under reduced pressure. The concentrate was completely dissolved in CHCl ₃ and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. 92.2 g (yield: 77%) of the compound X-4 was obtained.

Synthesis Example 2. Synthesis of Compound X-5

The following compound X-5 was synthesized in the same manner as in Synthesis Example 1, except that 3-chloronaphthalen-2-amine was used instead of 1-chloronaphthalen-2-amine.

X-5

Synthesis Example 3. Synthesis of Compound X-6

The following compound X-6 was synthesized in the same manner as in Synthesis Example 1, except that 2-chloronaphthalen-1-amine was used instead of 1-chloronaphthalen-2-amine.

X-6

Synthesis Example 4. Synthesis of Compound X-7

The following compound X-7 was synthesized in the same manner as in Synthesis Example 1, except that 9- (2-bromophenyl) -9H-carbazole was used instead of 2-bromo-N, N-diphenylaniline.

X-7

Synthesis Example 5. Synthesis of Compound X-8

Except that 9- (2-bromophenyl) -9H-carbazole was used in place of 2-bromo-N, N-diphenylaniline in Synthesis Example 2, the following compound X-8 was synthesized.

X-8

Synthesis Example 6. Synthesis of Compound X-9

9- (2-bromophenyl) -9H-carbazol was used instead of 2-bromo-N, N-diphenylaniline in Synthesis Example 3, the following compound X-9 was synthesized in the same manner.

X-9

SYNTHESIS EXAMPLE 7 Synthesis of Compound Y-3

1) Synthesis of Compound Y-1

Aniline 50.0 g (536.8 mmol, 1.0 eq), 2-chloro-4-phenylquinazoline 129.2. the g (536.8 mmol, 1.0 eq) , K 3 PO 4 341.8 g (1610.6 mmol, 3 eq), Pd (t -Bu 3 P) 2 1.37 g (2.7 mmol, 0.005 eq) and xylene (Xylene) to 1300 ml And the mixture was refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, and again decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 134.1 g (yield 84%) of compound Y-1

2) Synthesis of Compound Y-2

Y-1 135.7 g (456.3 mmol, 1.0 eq), 1,2-dibromobenzene 118.4. 1.13 g (2.3 mmol, 0.005 eq) of Pd ( t- Bu ₃ P) ₂ and 131.5 g (1369.0 mmol, 3 eq) of sodium tert-butoxide The mixture was dissolved in 1100 ml of xylene, refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 150.6 g (yield: 73%) of compound Y-2.

3) Synthesis of Compound Y-3

Compound Y-3 was synthesized in the same manner as in Synthesis Example 1, except that Y-2 was used instead of 2-bromo-N, N-diphenylaniline.

Synthesis Example 8. Synthesis of Compound X-10

2-bromo-N- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -N-phenylaniline was used instead of 2-bromo-N, N-diphenylaniline in Synthesis Example 3 The following compound X-10 was synthesized in the same manner except for using.

X-10

Synthesis Example 9 Synthesis of Compound X-11

Except that 4-biphenyl-4-yl) -N- (2-bromophenyl) -N, 6-diphenylpyrimidin-2-amine was used instead of 2-bromo-N, N-diphenylaniline in Synthesis Example 3 The following compound X-11 was synthesized.

X-11

Production Example 1. Preparation of Compound 1

[X-4] [Compound 1]

6.5 g (20.1 mmol, 1.1 eq) of 5-bromo-9-phenyl-9H-pyrido [2,3-b] indole and 10.0 g (18.3 mmol, 1.0 eq) of compound X- 0.05 g (0.1 mmol, 0.005 eq) of Pd ( t- Bu ₃ P) ₂ was 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 CHCl ₃ , washed with water, and further decompressed to remove the solvent. The resulting product was subjected to column chromatography to obtain 10.5 g (yield 73%) of Compound 1.

Production Example 2. Preparation of Compound 2

[X-4] [Compound 2]

Compound X-4 10.0 g (18.3 mmol , 1.0 eq), 2-chloro-4-phenylquinazoline 4.8 g (20.1 mmol, 1.1 eq), K 3 PO 4 11.6 g (54.8 mmol, 3 eq), Pd (t -Bu 0.05 g (0.1 mmol, 0.005 eq) of ₃ P) ₂ was dissolved in 50 ml of xylene, refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove the solvent. The resulting product was subjected to column chromatography to obtain 11.5 g (yield 85%) of Compound 2.

Production Example 3. Preparation of Compound 3

[X-4] [Compound 3]

Compound X-4 10.0 g (18.3 mmol , 1.0 eq), 2-chloro-3-phenylquinoxaline 4.8 g (20.1 mmol, 1.1 eq), K 3 PO 4 11.6 g (54.8 mmol, 3 eq), Pd (t -Bu 0.05 g (0.1 mmol, 0.005 eq) of ₃ P) ₂ was dissolved in 50 ml of xylene, refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. The resulting product was subjected to column chromatography to obtain 11.1 g (yield 81%) of Compound 3.

Production Example 4. Preparation of Compound 4

[X-4] [Compound 4]

5.69 g (20.1 mmol, 1.1 eq) of 3-bromoacenaphtho [1,2-b] pyrazine and 5.3 g (54.8 mmol) of sodium tert-butoxide were added to 10.0 g (18.3 mmol, 1.0 eq) 0.05 g (0.1 mmol, 0.005 eq) of Pd ( t- Bu ₃ P) ₂ 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 CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. The resulting product was subjected to column chromatography to obtain 10.8 g (yield 79%) of Compound 4.

Production Example 5. Preparation of Compound 5

[X-4] [Compound 5]

A mixture of 10.0 g (18.3 mmol, 1.0 eq) of compound X-4, 20.1 mmol, 1.1 eq of 5'-bromo-1,1 ': 3', 1 &quot; -terphenyl, Sodium tert- 0.05 g (0.1 mmol, 0.005 eq) of Pd ( t- Bu ₃ P) ₂ was 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 CHCl ₃ , washed with water, and further decompressed to remove the solvent. The resulting product was subjected to column chromatography to obtain 12.4 g (yield: 88%) of Compound 5.

Production Example 6. Preparation of Compound 6

[X-5] [Compound 6]

5.2 g (20.1 mmol, 1.1 eq) of 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine and 10.0 g (18.3 mmol, 1.0 eq) of compound X- 0.05 g (0.1 mmol, 0.005 eq) of sodium tert-butoxide (5.3 g, 54.8 mmol, 3 eq) and 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 CHCl ₃ , washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 12.9 g (yield 83%) of Compound 6.

Preparation 7. Preparation of Compound 7

[X-5] [Compound 7]

6.5 g (20.1 mmol, 1.1 eq) of 3-bromo-9-phenyl-9H-carbazole and 5.3 g (54.8 mmol) of sodium tert-butoxide were added to 10.0 g (18.3 mmol, 1.0 eq) 0.05 g (0.1 mmol, 0.005 eq) of Pd ( t- Bu ₃ P) ₂ 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 CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. The resulting residue was subjected to column chromatography to obtain 12.8 g (yield 89%) of Compound 7.

Production Example 8. Preparation of Compound 8

[X-6] [Compound 8]

5.5 g (20.1 mmol, 1.1 eq) of 2-bromo-9,9-dimethyl-9H-fluorene and 5.3 g of sodium tert-butoxide (10.0 g, 18.3 mmol, 1.0 eq) (54.8 mmol, 3 eq) and 0.05 g (0.1 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 CHCl ₃ , washed with water, and further decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 11.7 g (yield 87%) of Compound 8.

Production Example 9. Preparation of Compound 9

[X-6] [Compound 9]

Compound X-6 10.0 g (18.3 mmol , 1.0 eq), 2-chloroquinazoline-4-carbonitrile 3.8 g (20.1 mmol, 1.1 eq), K 3 PO 4 11.6 g (54.8 mmol, 3 eq), Pd (t -Bu 0.05 g (0.1 mmol, 0.005 eq) of ₃ P) ₂ was dissolved in 50 ml of xylene, refluxed and stirred. When the reaction was completed, the solvent was removed by decompression. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 9.9 g (yield 78%) of Compound 9.

Preparation 10. Preparation of Compound 10

[X-6] [Compound 10]

10.0 g (18.3 mmol, 1.0 eq) of compound X-6, 7.4 g (20.1 mmol, 1.1 eq) of 2- (4-chlorophenyl) -4,6- diphenylpyrimidine- butoxide 5.3 g (54.8 mmol, 3 eq) and 0.05 g (0.1 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 CHCl ₃ , washed with water, and further decompressed to remove the solvent. The resulting product was subjected to column chromatography to obtain 13.3 g (yield 83%) of Compound 10.

Production Example 11. Preparation of Compound 11

[X-7] [Compound 11]

6.9 g (20.1 mmol, 1.1 eq) of 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6- phenylpyrimidine, K ₃ the _{PO 4 11.6 g (55.1 mmol,} 3 eq), Pd (t -Bu 3 P) 2 0.05 g (0.1 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 CHCl ₃ , washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 12.6 g (yield 81%) of Compound 11.

Preparation 12. Preparation of Compound 12

[X-7] [Compound 12]

4.8 g (20.1 mmol, 1.1 eq) of 2-chloroindeno [1,2,3-de] quinazoline, 11.6 g (55.1 mmol, 3 eq) of K ₃ PO ₄ , 10.0 g (18.3 mmol, 1.0 eq) And 0.05 g (0.1 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 CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. The resulting product was subjected to column chromatography to obtain 10.5 g (yield 69%) of Compound 12.

Production Example 13. Preparation of Compound 13

[X-7] [Compound 13]

4.9 g (20.2 mmol, 1.1 eq) of K ₂ PO _4, 11.6 g (55.1 mmol, 3 eq) of 3-chloro-4- eq) and 0.05 g (0.1 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 CHCl ₃ , washed with water, and further decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 11.9 g (yield 87%) of Compound 13.

Production Example 14. Preparation of Compound 14

[X-7] [Compound 14]

Compound X-7 10.0 g (18.3 mmol , 1.0 eq), 2-chloropyrido [3,2-d] pyrimidine 3.3 g (20.2 mmol, 1.1 eq), K 3 PO 4 11.6 g (55.1 mmol, 3 eq), Pd 0.05 g (0.1 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. Thereafter, the reaction mixture was completely dissolved in CHCl ₃ , washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 10.0 g (yield: 81%) of Compound 14.

Production Example 15. Preparation of Compound 15

[X-8] [Compound 15]

Compound X-8 10.0 g (18.3 mmol , 1.0 eq), 4,6-di ([1,1'-biphenyl] -4-yl) -2-chloropyrimidine 8.4 g (20.2 mmol, 1.1 eq), K 3 PO the _{4 11.6 g (55.1 mmol, 3} eq), Pd (t -Bu 3 P) 2 0.05 g (0.1 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 CHCl ₃ , washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 14.8 g (yield 87%) of Compound 15.

Preparation 16. Preparation of Compound 16

[X-9] [Compound 16]

(10.0 g, 18.3 mmol, 1.0 eq) of compound X-9, 6.5 g (20.1 mmol, 1.1 eq) of 4-bromo-N, N-diphenylaniline, 5.3 g (54.8 mmol, 3 eq) and 0.05 g (0.1 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 CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. The resulting product was subjected to column chromatography to obtain 12.8 g (yield 89%) of Compound 16.

Preparation 17. Preparation of Compound 17

[X-9] [Compound 17]

6.9 g (20.1 mmol, 1.1 eq) of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 0.05 g (0.1 mmol, 0.005 eq) of sodium tert-butoxide (5.3 g, 54.8 mmol, 3 eq) and 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 CHCl ₃ , washed with water, and then decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 13.6 g (yield 87%) of Compound 17.

Preparation 18. Preparation of Compound 18

[X-9] [Compound 18]

4.8 g (20.2 mmol, 1.1 eq) of K ₂ PO _4, 11.6 g (55.1 mmol, 3 eq) of 2-chloro-4-phenylpyrido [ eq) and 0.05 g (0.1 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 CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. The resulting product was subjected to column chromatography to obtain 11.5 g (yield 84%) of Compound 18.

Preparation 19. Preparation of Compound 19

[Y-3] [Compound 19]

Compound Y-3 10.0 g (14.8 mmol , 1.0 eq), bromobenzene 2.6 g (16.3 mmol, 1.1 eq), sodium tert-butoxide (Sodium tert-butoxide) 4.3 g (44.5 mmol, 3 eq), Pd (t - Bu ₃ P) ₂ 0.04 g (0.07 mmol, 0.005 eq) was dissolved in 40 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 CHCl ₃ , washed with water, and again decompressed to remove the solvent. The resulting residue was subjected to column chromatography to obtain 10.2 g (yield 92%) of Compound 19.

Preparation 20. Preparation of 20

[X-10] [Compound 20]

3.3 g (12.8 mmol, 1.1 eq) of 3-bromo-1,1'-biphenyl and 3.7 g (38.6 mmol) of sodium tert-butoxide were added to 10.0 g (14.8 mmol, 1.0 eq) , 3 eq) and 0.03 g (0.06 mmol, 0.005 eq) of Pd ( t- Bu ₃ P) ₂ were dissolved in 30 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 CHCl ₃ , washed with water, and further decompressed to remove the solvent. The resulting product was subjected to column chromatography to obtain 10.5 g (yield: 88%) of Compound 20.

Preparation 21. Preparation of Compound 21

     [X-11] [Compound 21]

3.3 g (14.1 mmol, 1.1 eq) of 3-bromo-1,1'-biphenyl and 3.7 g (38.6 mmol) of sodium tert-butoxide were added to 10.0 g (12.8 mmol, 1.0 eq) , 3 eq) and 0.03 g (0.06 mmol, 0.005 eq) of Pd ( t- Bu ₃ P) ₂ were dissolved in 30 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 CHCl ₃ , washed with water, and again reduced in pressure to remove the solvent. The resulting residue was subjected to column chromatography to obtain 9.4 g (yield 81%) of Compound 21.

<Experimental Examples 1 to 17>

The compounds prepared in Preparation Examples were subjected to high purity sublimation purification by a conventionally known method, and red organic light emitting devices were prepared as follows.

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 base pressure was adjusted to 1 x 10 &lt; ^-6 &gt; torr. Then, an organic material was deposited on the ITO using DNTPD (700 ANGSTROM), alpha -NPB (300 ANGSTROM), the compound prepared by the preparation example (10 wt%) was co-deposited (300 Å) as a dopant, Alq3 (350 Å), and Alq3 (300 Å) were used as a host (1 to 4, 6, 9 to 15 and 17 to 21) 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 light emitting device of Comparative Example 1 was the same as the host of the light emitting layer in the organic light emitting device structure of Experimental Examples 1 to 17 except that CBP which is widely used as a general phosphorescent host material was used instead of the compound prepared by the preparation example of this specification Respectively.

The driving voltage, the current efficiency, the power efficiency, and the lifetime of the organic light emitting device manufactured according to Experimental Examples 1 to 17 and Comparative Example 1 were measured, and the results are shown in Table 1 below.

compound Driving voltage
(V) Current efficiency
(cd / A) Power efficiency
(lm / w) life span
(T95 @ 10mA) x coordinate y coordinate Experimental Example 1 One 4.99 22.96 14.89 180 0.660 0.330 Experimental Example 2 2 4.61 25.34 15.74 233 0.663 0.335 Experimental Example 3 3 4.91 22.04 13.77 205 0.660 0.331 Experimental Example 4 4 4.88 23.65 13.90 165 0.657 0.333 Experimental Example 5 6 4.92 23.59 13.85 164 0.653 0.334 Experimental Example 6 9 4.95 22.87 14.87 189 0.662 0.331 Experimental Example 7 10 4.81 23.89 14.57 225 0.662 0.332 Experimental Example 8 11 4.86 23.62 14.22 180 0.662 0.332 Experimental Example 9 12 5.10 21.50 15.31 156 0.660 0.332 Experimental Example 10 13 5.22 20.21 13.56 178 0.651 0.331 Experimental Example 11 14 4.81 22.45 13.72 202 0.661 0.334 Experimental Example 12 15 5.01 24.02 13.45 113 0.662 0.330 Experimental Example 13 17 4.90 22.37 14.32 135 0.660 0.332 Experimental Example 14 18 4.75 23.92 13.77 194 0.661 0.333 Experimental Example 15 19 4.70 25.01 15.31 210 0.663 0.333 Experimental Example 16 20 5.20 24.01 14.47 131 0.658 0.330 Experimental Example 17 21 5.01 23.41 14.17 146 0.658 0.330 Comparative Example 1 CBP 5.51 17.05 11.06 57 0.651 0.330

As a result, it was confirmed that all of the compounds 1 to 4, 6 and 9 to 15 and 17 to 21 according to one embodiment of the present invention had red emission and the driving voltage was lowered than that of the organic light emitting device of Comparative Example using CBP High current efficiency, and excellent performance in terms of life.

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 (16)

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

In formula (1)
R ₉ and R ₁₀ may bond to each other to form a benzene ring, or R ₁₀ and R ₁₁ may bond to each other to form a benzene ring, or R ₁₁ and R ₁₂ may combine to form a benzene ring, R &lt; _{20 &gt;} ) _m ,
m is an integer of 1 to 4,
A group of R ₉ to R ₁₂ which does not form a ring, R ₁ to R ₈ , R ₁₃ to R ₁₈ and R ₂₀ are hydrogen,
Ar ₁ and Ar ₂ are the same or different and each independently represents an aryl group substituted or unsubstituted with a nitrile group, an alkyl group, or an aryl group; An aromatic or aliphatic heterocyclic group which is unsubstituted or substituted with at least one group selected from the group consisting of a nitrile group, an alkyl group, an aryl group, and an aryl group substituted with a nitrile group,
L ₁ and L ₂ are the same or different and are each independently a direct bond; Or an arylene group, and L ₁ may combine with R ₁ or R ₁₈ to form a ring. The compound according to claim 1, wherein at least one of Ar ₁ and Ar ₂ is represented by one of the following formulas A to D:
(A)

In formula (A)
Y ₁ to Y ₃ are the same or different and are each independently N or CRd,
R ₂₀₁ and R _d are the same or different from each other, and each independently hydrogen; A nitrile group; An alkyl group; Or an aryl group substituted with a nitrile group, an alkyl group, a nitrile group, or an aryl group substituted or unsubstituted with an aryl group, or is bonded to adjacent substituents to form a ring,
[Chemical Formula B]

In formula (B)
T ₁ and T ₂ are the same or different and are each independently N or CRe,
R ₃₀₀ to R ₃₀₅ and R e are the same or different and each independently hydrogen or combine with adjacent substituents to form a ring, n is 1 or 2,
&Lt; RTI ID = 0.0 &

In formula (C)
U ₁ to U ₈ are the same or different and each independently N or CRf,
L ₃ is a direct bond; Or an arylene group,
Rf is hydrogen,
[Chemical Formula D]

In Formula D, one of U ₉ and U ₁₀ is N and the remainder is CRg,
L ₄ is a direct bond; Or an arylene group,
Rg, _R321 and _R322 are the same or different from each other, and each independently hydrogen; Or an aryl group, q is an integer of 1 to 5,
When q is 2 or more, two or more R ₃₂₁ are the same or different from each other. The compound according to claim 1, wherein the compound represented by formula (1) is represented by one of the following formulas (2) to (4):
(2)

(3)

[Chemical Formula 4]

In formulas (2) to (4), R ₁ to R ₁₈ , R ₂₀ , m, L ₁ , L ₂ , Ar ₁ and Ar ₂ are as defined in formula (1). The compound according to claim 1, wherein the formula (1) is represented by one of the following formulas (5) to (7):
[Chemical Formula 5]

[Chemical Formula 6]

(7)

In Formulas 5 to 7, R ₁ to R ₁₈ , R ₂₀ , m, L ₂ , Ar ₁ and Ar ₂ are as defined in Formula (1)
R ₁₉ is hydrogen, and n is an integer of 1 to 4. The compound according to claim 1, wherein the compound represented by formula (1) is represented by one of the following formulas (8) to (10):
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

Wherein R ₁ to R ₁₈ , R ₂₀ , m, L ₂ , Ar ₁ and Ar ₂ are as defined in Formula (1)
R ₁₉ is hydrogen, and p is an integer of 1 to 3. The compound according to claim 2, wherein the formula (A) is represented by the following formula (A-5):
[A-5]

In formula (A-5), Y ₁ and Y ₂ are as defined in formula (A)
Z ₁ to Z ₄ are the same or different and are each independently N or CRc,
Rc are the same or different and are each independently selected from the group consisting of hydrogen; A nitrile group; An alkyl group; Or an aryl group substituted with a nitrile group, an alkyl group, a nitrile group, or an aryl group substituted or unsubstituted with an aryl group. The compound according to claim 6, wherein the formula (A-5) is represented by one of the following formulas (A-6) to (A-9).
[A-6]

[A-7]

[A-8]

[A-9]

In Formulas A-6 to A-9,
Y ₁ and Y ₂ are as defined in formula (A)
Q is a direct bond, C (= O), or CRhRi,
R ₂₀₂ to R ₂₀₅ , R ₂₁₀ to R ₂₁₆ , Rh and R 1 are the same or different from each other, and each independently hydrogen; A nitrile group; An alkyl group; Or an aryl group substituted with a nitrile group, an alkyl group, a nitrile group, or an aryl group substituted or unsubstituted with an aryl group. The compound according to claim 6, wherein the formula (A-5) is represented by one of the following formulas A-10 to A-13:
[A-10]

[A-11]

[A-12]

[A-13]

In Formulas A-10 to A-13,
R ₂₀₂ to R ₂₀₉ are the same or different from each other, and each independently hydrogen; A nitrile group; An alkyl group; Or an aryl group substituted with a nitrile group, an alkyl group, a nitrile group, or an aryl group substituted or unsubstituted with an aryl group. The compound according to claim 7, wherein the formula (A-9) is represented by one of the following formulas (A-14) to
[Chemical formula A-14]

[A-15]

[A-16]

In Formulas A-14 to A-16,
R ₂₁₀ to R ₂₁₈ are the same or different from each other and each independently hydrogen; A nitrile group; An alkyl group; Or an aryl group substituted with a nitrile group, an alkyl group, a nitrile group, or an aryl group substituted or unsubstituted with an aryl group. The compound according to claim 2, wherein the formula (B) is represented by one of the following formulas (B-2) to (B-4)
[Formula B-2]

[Formula B-3]

[Formula B-4]

In Formulas B-2 to B-4,
R ₃₀₀ to R ₃₁₂ are hydrogen. The compound according to claim 2, wherein the formula (C) is represented by the following formula (C-2) or (C-3)
[Chemical formula C-2]

[Formula C-3]

In Formulas C-2 and C-3,
L ₃ is as defined in formula (C)
R ₃₁₂ to R ₃₁₉ are hydrogen. The compound according to claim 2, wherein the formula (D) is represented by the following formula (D-1) or (D-2)
[Formula D-1]

[Formula D-2]

Substituents of formulas D-1 and D-2 are as defined in 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 includes a compound according to any one of claims 1 to 13 Lt; / RTI &gt; The organic electroluminescent device according to claim 14, wherein the organic material layer includes an electron transporting layer, an electron injecting layer, a layer which simultaneously transports electrons and injects electrons, a light emitting layer, a hole transporting layer, a hole injecting layer or a layer simultaneously transporting holes and injecting holes, , The electron injecting layer, the layer which simultaneously transports electrons and the electron injecting layer, the light emitting layer, the hole transporting layer, the hole injecting layer, or the layer which simultaneously transports the holes and injects the holes contains the above compound. 15. The organic light emitting device according to claim 14, wherein the light emitting layer comprises the compound.

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