KR20170134132A - Fused cyclic and organic light emitting device using the same - Google Patents

Abstract

Provided are a compound represented by chemical formula 1 and an organic light emitting device comprising the compound in an organic layer. According to an embodiment of the present invention, the compound, when being used in an organic light emitting device, can lower driving voltage of the device, can improve light efficiency and can improve lifespan properties of the device by thermal stability of the compound.

Description

FIELD OF THE INVENTION [0001] The present invention relates to a condensed ring compound and an organic light emitting device using the condensed ring compound.

The present invention relates to an organic light emitting device in which a condensed ring compound is contained in an organic compound layer capable of greatly improving lifetime, efficiency, electrochemical stability, and thermal stability of the organic light emitting device.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows. When an organic layer is positioned between an anode and a cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using this principle may be generally composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

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

Korean Patent Publication No. 2000-0051826

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

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

[Chemical Formula 1]

In Formula 1,

Q is a condensed aromatic polycyclic group of C ₁₀ to C ₃₀ ,

L ₁ is a direct bond; A substituted or unsubstituted C ₆ to C ₄₀ arylene group; Or a substituted or unsubstituted C ₂ to C ₄₀ heteroarylene group,

R ₁ to R ₄ are the same or different and are each independently hydrogen; A halogen, an amino group, a nitrile group, a nitro group, a cycloalkyl group of C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl groups, C ₁ to C ₄₀ alkoxy groups, C ₃ to C ₄₀ of a, C ₂ to C ₄₀ A C ₃ to C ₄₀ cycloalkyl group which is unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₂ to C ₄₀ heteroaryl group; A halogen, an amino group, a nitrile group, a nitro group, a cycloalkyl group of C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl groups, C ₁ to C ₄₀ alkoxy groups, C ₃ to C ₄₀ of a, C ₂ to C ₄₀ a heterocycloalkyl group, an aryl group of C ₆ to C ₄₀ aryl group and a C ₂ to C ₄₀ by at least one group selected from the heteroaryl group consisting of a substituted or unsubstituted C ₆ to C ₄₀ of the; And a halogen, an amino group, a nitrile group, a nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl groups, C ₁ to C ₄₀ alkoxy groups, C ₃ to C ₄₀ cycloalkyl group, C ₂ to about C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and a C ₂ to C ₄₀ by at least one group selected from the heteroaryl group consisting of groups selected from the group consisting of a heteroaryl, a substituted or unsubstituted C ₂ to C ₄₀ of ,

Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₄₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₄₀ heteroaryl group,

m is an integer of 0 to 16,

n and p are each an integer of 0 to 4,

q is an integer of 0 to 5,

When m, n, p and q are each 2 or more, the substituents in the parentheses are the same or different from each other.

In addition, one embodiment of the present invention provides an organic light emitting device including a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes the compound of Formula 1 .

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can lower the driving voltage of the device, improve the light efficiency, and improve the lifetime characteristics of the device by the thermal stability of the compound when used in an organic light emitting device. In particular, the compounds described in this specification can be used as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material. In addition, the compounds described in this specification can preferably be used as a hole transporting layer.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

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

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

Illustrative examples of such substituents are set forth below, but are not intended to be limiting. Embodiments of the present invention are provided to more fully describe the present invention to those skilled in the art.

In the present specification, the term "substituted or unsubstituted" means a halogen, an amino group, a nitrile group, a nitro group, a germanium group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₁ to C ₄₀ alkoxy group , A C ₃ to C ₄₀ cycloalkyl group, a C ₂ to C ₄₀ heterocycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C ₂ to C ₄₀ heteroaryl group, it means.

In the present specification, the condensed aromatic polycyclic group preferably has 10 to 30 carbon atoms. According to one embodiment, the condensed aromatic polycyclic group has 10 to 20 carbon atoms. According to another embodiment, the condensed aromatic polycyclic group has 10 to 14 carbon atoms. Specific examples thereof include, but are not limited to, naphthalene, anthracene, benzanthracene, phenanthrene, tetracene, pyrene, and triphenylene.

In the present specification, the halogen includes F, Cl, Br and I.

In the present specification, the alkyl group may be linear or branched and preferably has 1 to 40 carbon atoms. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. Specific examples thereof include a methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, Butyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, pentyl group, pentyl group, isopentyl group, isopentyl group, neopentyl group, Butyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n- Propyl group, a 1-ethyl-propyl group, a 2-ethylhexyl group, a 1-methylpropyl group, An isohexyl group, a 4-methylhexyl group, a 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched and preferably has 2 to 40 carbon atoms. According to one embodiment, the alkenyl group has 2 to 30 carbon atoms. According to another embodiment, the alkenyl group has 2 to 20 carbon atoms. Specific examples thereof include, but are not limited to, an alkenyl group to which an aryl group such as a stilbenyl group or a styrenyl group is connected.

In the present specification, the alkoxy group preferably has 1 to 40 carbon atoms. According to one embodiment, the alkoxy group has 1 to 30 carbon atoms. According to one embodiment, the number of carbon atoms in the alcohol moiety is from 1 to 20. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an isoamyloxy group and a hexyloxy group.

In the present specification, the cycloalkyl group preferably has 3 to 40 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the cycloalkyl group may be 3 to 10. Specific examples thereof include cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 , 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but are not limited thereto.

As used herein, a heterocycloalkyl group is a heteroatom and includes at least one of S, O, N, Si, and Se, and has from 2 to 40 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocycloalkyl group is from 2 to 30. According to one embodiment, the number of carbon atoms of the heterocycloalkyl group is from 2 to 20. According to one embodiment, the number of carbon atoms of the heterocycloalkyl group is 2 to 10. Specific examples thereof include tetrahydropyranyl group, tetrahydrofuranyl group, and the like, but are not limited thereto.

In the present specification, the aryl group may be straight-chain or branched and preferably has 6 to 40 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Examples of the unsubstituted aryl group may be phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, klycenyl, fluorenyl, And examples of the substituted aryl group include a 9,9-dimethylfluorenyl group, a phenyl group substituted with naphthalene, a phenyl group substituted with dibenzopyrrole, a phenyl group substituted with a 9,9-dimethylfluorenyl group, a dibenzofuran , A phenyl group substituted with dibenzothiophene, a phenyl group substituted with triphenylamine, and the like, but the present invention is not limited thereto.

In the present specification, the heteroaryl group includes at least one of S, O, N, Si and Se as a heteroatom and preferably has 2 to 40 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 20 carbon atoms. According to another embodiment, the heteroaryl group may have 2 to 10 carbon atoms. Examples of the unsubstituted heteroaryl group include carbazole group, thiophene group, furan group, pyrrolyl group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, A thiazolyl group, a triazyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofurane group, a dibenzofurane group, a phenanthroline group, a benzothiophene group, a benzothiophene group, , A thiazole group, an isoxazole group, an oxadiazole group, a thiadiazole group, a benzothiazole group and a dibenzofurane group, but not limited thereto, and examples of the substituted heteroaryl group include 9-phenylcarbazole group and the like However, the present invention is not limited thereto.

In the present specification, the germanium group can be represented by the formula _: -GeR _a R _b R _c wherein R _a , R _b and R _c are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The germanium group specifically includes, but is not limited to, a trimethyl germanium group, a triethyl germanium group, and a t-butyldimethyl germanium group.

In the present specification, the aryl group of the aralkyl group can be applied to the description of the aryl group described above. The aralkyl group preferably has 7 to 30 carbon atoms. According to one embodiment, the aralkyl group has 7 to 20 carbon atoms. According to another embodiment, the aralkyl group has 7 to 15 carbon atoms.

In the present specification, the aromatic hydrocarbon group and the aromatic group can be applied to the description of the aryl group described above.

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

In the present specification, the aromatic hetero ring group can be applied to the description of the above-mentioned heteroaryl group.

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

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

In the present specification, the arylthio group and the aryl group in the aryloxy group can be applied to the description of the aryl group described above.

In the present specification, the alkoxy group in the alkoxycarbonyl group can be applied to the description of the alkoxy group described above.

는 상기 화학식 1에 결합되는 부위이다.In the present specification,

Is a moiety bonded to the formula (1).

According to one embodiment of the present invention, in the general formula (1), Q is a condensed aromatic polycyclic group having 10 to 30 carbon atoms. Specifically, the number of carbon atoms in the condensed aromatic polycyclic group may be 10 to 20, more specifically, 10 to 14. Specific examples of Q include naphthalene, anthracene, phenanthrene, tetracene, triphenylene, pyrene, and the like.

In the embodiment of the present invention, Q in Formula 1 may be naphthalene, phenanthrene, triphenylene, or pyrene.

In another embodiment, Q in Formula 1 may be bonded in the endo or exo direction.

The general definition of the endo or exo isomer is the isomer of a bridge ring compound having a substituent and the endo is an isomer located closest to the bridge where the substituent of the compound is the most carbon number, (exo) is an isomer located farthest from the bridge in which the substituent of the compound has the greatest number of carbon atoms, and can be applied to the compounds of the present invention.

According to one embodiment of the present invention, L ₁ in Formula ₁ is a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

According to another embodiment, the arylene group of L < ₁ > may have 6 to 40 carbon atoms, specifically 6 to 30, more particularly 6 to 20 carbon atoms.

In another embodiment, the heteroarylene group of L < ₁ > may have 2 to 40 carbon atoms, specifically 2 to 30, more particularly 2 to 20 carbon atoms.

According to one embodiment of the present disclosure, L ₁ in formula (1) may be bonded to an ortho, meta or para position with respect to the bonded core structure.

According to one embodiment of the present invention, L ₁ in Formula 1 may be a phenyl group.

According to another embodiment, L < ₁ > may be a direct bond.

According to one embodiment of the present invention, R ₁ to R ₄ are the same or different and each independently represents hydrogen, a substituted or unsubstituted cycloalkyl group having 3 to 40 carbon atoms, a substituted or unsubstituted 6 to 40 carbon atom An aryl group and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

According to the compound according to the present invention, the substituents of the above formula (1) will be described more specifically.

According to one embodiment of the present disclosure, the halogen of R ₁ to R ₄ includes F, Cl, Br and I.

According to one embodiment of the present invention, the alkyl group of R ₁ to R ₄ may have 1 to 40 carbon atoms, specifically 1 to 30 carbon atoms, more particularly 1 to 20 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl group, But are not limited to, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl and heptyl groups.

According to one embodiment of the present invention, the alkenyl group of R ₁ to R ₄ may have 2 to 40 carbon atoms, specifically 2 to 30 carbon atoms, more particularly 2 to 20 carbon atoms. Specific examples of the alkenyl group include, but are not limited to, an alkenyl group to which an aryl group such as a stilbenyl group or a styrenyl group is connected.

According to one embodiment of the present invention, the alkoxy group of R ₁ to R ₄ may have 1 to 40 carbon atoms, specifically 1 to 30 carbon atoms, more particularly 1 to 20 carbon atoms. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, and a pentyloxy group.

According to one embodiment of the present invention, the cycloalkyl group of R ₁ to R ₄ may have 3 to 40 carbon atoms, specifically 3 to 30 carbon atoms, more particularly 3 to 20 carbon atoms. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopentyl group, a cyclohexyl group, and the like.

According to one embodiment of the present invention, the heterocycloalkyl group of R ₁ to R ₄ is at least one of S, O, N, Si and Se as a heteroatom, the number of carbon atoms of the heterocycloalkyl group is 2 to 40, 2 to 30, more particularly 2 to 20 carbon atoms. Specific examples thereof include, but are not limited to, a tetrahydropyran group, a tetrahydrofuran group, and the like.

In another embodiment, the heterocycloalkyl group comprises one or more of O, N, and S. In another embodiment,

According to one embodiment of the present invention, the aryl group of R ₁ to R ₄ may be linear or branched and has 6 to 40 carbon atoms, specifically 6 to 30, more particularly 6 to 20 carbon atoms. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a klycenyl group and a phenanthrenyl group.

According to one embodiment of the present invention, the heteroaryl group of R ₁ to R ₄ may be straight-chain or branched and is a cyclic group comprising at least one of S, O, N, Si and S as a hetero atom, May have 2 to 40 carbon atoms, specifically 2 to 30 carbon atoms, more particularly 2 to 20 carbon atoms. Specific examples of the heteroaryl group include a carbazole group, a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a quinolyl group, an isoquinoline group, But is not limited thereto.

In another embodiment, the heteroaryl group of R &_lt; ₁ > to R &_lt; ₄ > comprises at least one of O, N and S.

According to one embodiment of the present disclosure, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₄₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₄₀ heteroaryl group.

In one embodiment of the present disclosure, the Ar < _{1 >} And Ar ₂ The aryl group may be straight-chain or branched and has 6 to 40 carbon atoms, specifically 6 to 30, more specifically 6 to 20 carbon atoms.

The Ar ₁ And Ar ₂ The substituted or unsubstituted C ₆ to C ₄₀ aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or a 9,9-dimethylfluorenyl group.

The Ar ₁ And Ar ₂ The substituted or unsubstituted C ₆ to C ₄₀ aryl group is preferably a phenyl group substituted with naphthalene, a phenyl group substituted with dibenzopyrrole, a phenyl group substituted with a 9,9-dimethylfluorenyl group, a phenyl group substituted with dibenzofuran, A thiophene-substituted phenyl group, or a triphenylamine-substituted phenyl group.

In one embodiment of the present invention, the substituted or unsubstituted C ₂ to C ₄₀ heteroaryl group of Ar ₁ and Ar ₂ may be straight-chain or branched and has 2 to 40 carbon atoms, specifically 6 to 30, More specifically from 6 to 20 carbon atoms. The heteroaryl group may be a heteroaryl group substituted or unsubstituted with an aryl group.

The substituted or unsubstituted C ₂ to C ₄₀ heteroaryl group of Ar ₁ and Ar ₂ may be a dibenzofurane group, a dibenzothiophene group or a 9-phenylcarbazole group.

According to one embodiment of the present invention, m, n, p and q in the above formula (1) are as follows.

m is an integer of 0 to 16,

n and p are each an integer of 0 to 4,

q is an integer of 0 to 5,

When m, n, p and q are each 2 or more, the substituents in the parentheses are the same or different from each other.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (7).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the general formulas (2) to (7), the substituent is as defined in the general formula (1).

According to one embodiment of the present disclosure, L < ₂ > is a direct bond; A substituted or unsubstituted C ₆ to C ₃₄ arylene group; Or a substituted or unsubstituted C ₂ to C ₃₄ heteroarylene group.

In the L ₂ , the arylene group may have 6 to 34 carbon atoms, specifically 6 to 30, more specifically 6 to 20 carbon atoms.

In L ₂ , the heteroarylene group may have 2 to 34 carbon atoms, specifically 2 to 30 carbon atoms, more specifically 2 to 20 carbon atoms.

The L < _{2 >} may be bonded to an ortho, meta or para position with respect to the bonded core structure.

L < ₂ > may be a direct bond.

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

The compound according to one embodiment of the present specification can be produced by a production method described below.

For example, the compound of Formula 1 can be prepared as a core structure as shown in Reaction Scheme 1 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

The condensed ring compound according to the present specification can be prepared by a multistage chemical reaction. For example, the following reaction formula can be performed.

[Reaction Scheme]

One embodiment of the present invention is an organic light emitting device comprising an anode, a cathode, and at least one organic layer disposed between the anode and the cathode, wherein at least one of the organic layers includes a compound represented by Formula 1 Emitting layer.

In one embodiment of the present invention, the organic material layer containing the compound represented by Formula 1 is an organic light emitting device that is a hole transporting layer or an electron blocking layer.

In one embodiment of the present invention, at least one of the organic layers includes the compound represented by Formula 1, and the compound represented by Formula 8 is included in the light emitting layer of the organic layer.

 [Chemical Formula 8]

In Formula 8,

Ar ₃ is a benzofluorene skeleton, a fluoranthene skeleton, a pyrene skeleton or a chrysene skeleton,

L ₃ is a single bond, a C ₆ to C ₃₀ aromatic hydrocarbon group or a C ₅ to C ₃₀ heterocyclic group,

R ₅ and R ₆ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₃₀ aromatic hydrocarbon group, a substituted or unsubstituted C ₅ to C ₃₀ heterocyclic group, a substituted or unsubstituted A C ₁ to C ₃₀ alkyl group and a substituted or unsubstituted C ₇ to C ₃₀ aralkyl group, R ₅ and R ₆ may be bonded to each other to form a saturated or unsaturated ring,

r is an integer of 1 or more,

When r is 2 or more, R ₅ are the same as or different from each other, and R ₆ is the same as or different from each other.

In one embodiment of the present specification, R ₅ and R ₆ are the same or different and are each independently a substituted or unsubstituted C ₆ to C ₃₀ aromatic hydrocarbon group.

In one embodiment of the present disclosure, L- ₃ is a single bond.

In one embodiment of the present specification, Ar ₃ is a pyrene skeleton.

In one embodiment of the present specification, Ar ₃ is a pyrene skeleton, L- ₃ is a single bond, R ₅ and R ₆ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₃₀ An aromatic hydrocarbon group, and r is 2.

In one embodiment of the present invention, Ar ₃ is a pyrene skeleton, L- ₃ is a single bond, R ₅ and R ₆ are aryl groups substituted with -GeRaRbRc, and r is 2.

In one embodiment of the present invention, Ar ₃ is a pyrene skeleton, L- ₃ is a single bond, R ₅ and R ₆ are phenyl groups substituted with -GeRaRbRc, and r is 2.

In another embodiment, Ra, Rb and Rc are methyl groups.

One embodiment of the present invention is an organic light emitting device in which at least one of the organic layers includes the compound represented by Formula 1 and the structure of Formula 9 is included in the light emitting layer of the organic layer.

[Chemical Formula 9]

In Formula 9,

이고,R ₉ represents a substituted or unsubstituted 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Phenanthryl group, 9-phenanthryl group, 1-naphthacene group, 2-naphthacene group, 9-naphthacene group, 1-pyrenyl group, Methyl-1-naphthyl group or a 4-methyl-1-

ego,

R ₁₀ represents a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Naphthacenylene group, 1-naphthacenylene group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenyl group, P-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3- Methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenyl group, 4 " And a 3-fluorantheny group,

R ₇ to R ₈ are the same or different and each independently represents a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, Or an arylthio group having 5 to 50 unsubstituted nuclear atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group,

s1 and s2 are integers of 0 to 4, respectively.

In one embodiment of the present specification, _R9- is a 1-naphthyl group or a 2-naphthyl group.

In one embodiment of the present specification, R ₁₀ is a 1-naphthyl group or a 2-naphthyl group.

In one embodiment of the present disclosure, s1 and s2 are zero.

In another embodiment, R ₉ and R ₁₀ are the same or different and each independently an 1-naphthyl group or a 2-naphthyl group, and s 1 and s 2 are 0.

In another embodiment, R- ₉ is an 1-naphthyl group, R _10- is a 2-naphthyl group, and s 1 and s 2 are 0.

In one embodiment of the present invention, at least one of the organic layers includes a compound represented by Formula 1 and includes a structure represented by Chemical Formulas 8 and 9 in the light emitting layer of the organic material layer, and Ar ₃ Is a pyrene skeleton, L- ₃ is a single bond, R ₅ and R ₆ are aryl groups substituted with -GeRaRbRc, r is 2, R ₉ and R ₁₀ are the same or different from each other Is independently an 1-naphthyl group or a 2-naphthyl group, and s1 and s2 are each 0.

One embodiment of the present invention is an organic light-emitting device comprising the structure of Formula 9 as a material of a host of the light-emitting layer in the organic material layer.

Another embodiment is an organic light emitting device comprising the structure of Formula 9 as a host of the light emitting layer in the organic material layer and the structure of Formula 9 as a dopant.

1 and 2 show an example of an organic light emitting device according to the present invention. FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 FIG.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.

For example, the organic light emitting device in this specification may have a structure including a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and an electron blocking layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

In another embodiment, the organic material layer includes a hole transporting layer or an electron blocking layer.

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

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 includes the compound of the present invention, that is, the compound represented by the above formula (1).

The organic light emitting element of the present specification can be produced, for example, by sequentially laminating an anode, an organic layer and a cathode on a substrate. In this case, a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation may be used, but the present invention is not limited to these methods.

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] (PEDT), 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.

As the hole injecting material, 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 porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility to holes 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 combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; 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.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, 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 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.

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

<Production Example>

Scheme 1. Preparation of Compound A

(1) Preparation of compound a

(2) Preparation of Compound A

Scheme 2. Preparation of compound B

(1) Production of compound b

(2) Preparation of Compound (B)

Reaction 3. Preparation of Compound C

(1) Production of compound c

(2) Preparation of Compound C

Scheme 4. Preparation of compound D

(1) Preparation of compound d

(2) Preparation of Compound (D)

Scheme 5. Preparation of Compound E

(1) Preparation of Compound e

(2) Preparation of Compound E

Scheme 6. Preparation of Compound F

(1) Preparation of Compound (f)

(2) Preparation of Compound F

Scheme 7. Preparation of Compound G

(1) Production of compound g

(2) Preparation of Compound G

Scheme 8. Preparation of Compound H

(1) Production of compound h

(2) Preparation of Compound H

Scheme 9. Preparation of compound I

(1) Preparation of compound i

(2) Preparation of Compound (I)

Synthesis Example 1. Synthesis of Compound 1

(8.0 g, 19.60 mmol), di ([1,1'-biphenyl] -4-yl) amine (7.03 g, 21.89 mmol) and NaOt-Bu (2.49 g, 25.87 mmol) are added to 260 ml of toluene, and the temperature is raised while stirring. After the temperature has risen and refluxing begins, slowly drop the bis (tri-tert-butylphosphine) palladium (0.10 g, 0.20 mmol). After 3 hours, the reaction was terminated. The temperature was lowered to room temperature, and the mixture was concentrated under reduced pressure. The residue was subjected to column purification with tetrahydrofuran: hexane = 20: 1 to obtain 10.96 g (80%) of Compound 1. (MS [M + H] &lt; + &gt; = 688)

Synthesis Example 2. Synthesis of Compound 2

Compound A (9.0 g, 22.39 mmol) and N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluoren- (8.89 g, 24.63 mmol) and NaOt-Bu (2.80 g, 29.10 mmol) were dissolved in 200 ml of toluene, and the temperature was elevated with stirring. After the temperature has risen and refluxing begins, slowly drop the bis (tri-tert-butylphosphine) palladium (0.11 g, 0.22 mmol). After 1 hour, the reaction was terminated, the temperature was lowered to room temperature, and the mixture was concentrated under reduced pressure, followed by column purification with tetrahydrofuran: hexane = 12: 1 to obtain 8.84 g (65%) of Compound 2. (MS [M + H] &lt; + &gt; = 728)

Synthesis Example 3. Synthesis of Compound 3

Compound A (7.5 g, 18.66 mmol) and N - ([1,1'-biphenyl] -4-yl) - [1,1'- biphenyl] -2- amine 6.59g, 20.52mmol) and NaOt-Bu (2.33g, 24.25mmol) in 200ml of toluene, and then elevate the temperature with stirring. After the temperature has risen, begin to reflux, slowly drop the bis (tri-tert-butylphosphine) palladium (0.10 g, 0.19 mmol). After 6 hours, the reaction was terminated, the temperature was lowered to room temperature, and the mixture was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate (240 ml) to obtain 7.41 g (58%) of compound 3. (MS [M + H] &lt; + &gt; = 688)

Synthesis Example 4. Synthesis of Compound 4

To a 500 ml round-bottomed flask in a nitrogen atmosphere was added compound A (11.5 g, 28.61 mmol) and N- (4- (dibenzo [b, d] furan-4- yl) phenyl) -9,9- -2-amine (14.19 g, 31.47 mmol) and NaOt-Bu (3.57 g, 37.19 mmol) were added to 240 ml of toluene and the temperature was raised with stirring. After the temperature has risen and refluxing begins, slowly drop the bis (tri-tert-butylphosphine) palladium (0.15 g, 0.29 mmol). After 9 hours, the reaction was terminated, the temperature was lowered to room temperature, and the mixture was concentrated under reduced pressure. The residue was recrystallized from ethyl acetate (280 ml) to obtain 17.77 g (76%) of Compound (4). (MS [M + H] &lt; + &gt; = 818)

Synthesis Example 5. Synthesis of Compound 5

(9.76 g, 21.79 mmol), (4- (di ([1,1'-biphenyl] -yl) amino) phenyl) boronic acid (9.40 g, 22.88 mol) in a 500 ml round- Was dissolved in 240 ml of tetrahydrofuran. To the mixture was added 2M potassium carbonate aqueous solution (120 ml), tetrakis- (triphenylphosphine) palladium (0.76 g, 0.65 mmol) was added and the mixture was heated with stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to obtain Compound 5 (14.44 g, yield: 87%). (MS [M + H] &lt; + &gt; = 728)

Synthesis Example 6. Synthesis of Compound 6

(9.54 g, 23.73 mmol) and N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluoren- (9.00 g, 24.92 mmol) and NaOt-Bu (2.96 g, 30.85 mmol) were added to 240 ml of toluene and the temperature was raised while stirring. After the temperature has risen and refluxing begins, slowly drop the bis (tri-tert-butylphosphine) palladium (0.12 g, 0.24 mmol) into the flask. After 3 hours, the reaction was terminated, the temperature was lowered to room temperature, and the mixture was concentrated under reduced pressure, followed by column purification with tetrahydrofuran: hexane = 25: 1 to prepare 12.27 g (67%) of Compound 6. (MS [M + H] &lt; + &gt; = 776)

Synthesis Example 7: Synthesis of Compound 7

To a 500 ml round-bottomed flask in a nitrogen atmosphere was added compound D (7.16 g, 15.84 mmol) and N - ([1,1'-biphenyl] -4-yl) - [1,1 ': 4', 1 " Phenyl] -4-amine (6.60 g, 16.63 mmol) and NaOt-Bu (1.98 g, 20.59 mmol) were added to 200 ml of toluene and the temperature was raised with stirring. After the temperature has risen and refluxing begins, slowly drop down bis (tri-tert-butylphosphine) palladium (0.08 g, 0.16 mmol). After 4 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction mixture was concentrated under reduced pressure and then purified by column chromatography to obtain 6.94 g (59%) of Compound 7. (MS [M + H] &lt; + &gt; = 738)

Synthesis Example 8. Synthesis of Compound 8

To a 500 ml round bottom flask in a nitrogen atmosphere was added a solution of compound G (5.75 g, 11.45 mmol) and N- (4- (dibenzo [b, d] furan- 4-amine (4.94 g, 12.03 mmol) and NaOt-Bu (1.43 g, 14.89 mmol) were added to 200 ml of toluene, and the temperature was raised with stirring. After the temperature has risen and reflux begins, slowly drop the bis (tri-tert-butylphosphine) palladium (0.06 g, 0.11 mmol). After 5 hours, the reaction was terminated, the temperature was lowered to room temperature, the reaction solution was concentrated under reduced pressure, and then purified by column chromatography to obtain 4.78 g (48%) of Compound 8. (MS [M + H] &lt; + &gt; = 878)

Synthesis Example 9 Synthesis of Compound 9

To a 500 ml round-bottomed flask under nitrogen was added compound D (7.29 g, 16.13 mmol), (4 - ([1,1'-biphenyl] -4-yl (9,9- ) (8.15 g, 16.93 mol) was dissolved in 280 ml of tetrahydrofuran, followed by addition of 2M aqueous potassium carbonate solution (140 ml) and tetrakis- (triphenylphosphine) palladium mmol) were added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 220 ml of tetrahydrofuran to obtain Compound 9 (8.74 g, yield: 67%). (MS [M + H] &lt; + &gt; = 854)

Generally, the final compounds can be analyzed by nuclear magnetic resonance (NMR), mass spectrometry (Mass) and the like. Compounds 1 to 9, however, have many aromatic structures, and ¹ H NMR analysis in nuclear magnetic resonance (NMR) reveals that they overlap many times between δ = 7.0 and 7.5. Therefore, the structure of the compound was analyzed by further measuring the mass analysis (Mass).

FD-MS means a mass spectrometer. When mass spectrometry is used, the final compounds are broken and several peaks appear. M / z means the peak. In other words, m / z means the mass analysis main peck of compounds 1-9. This confirms the presence of the compounds.

Table 1 shows values measured by a nuclear magnetic resonance (NMR) and a mass spectrometer (Mass) of the compounds 1 to 9.

compound &Lt; ¹ &gt; H NMR (CDCl3, 400MHz) FD-MS One (d, IH), 7.61-7.45 (m, 26H), 6.86 (d, IH) d, 2H) m / z = 687.29
(C ₅₃ H ₃₇ N = 687.89) 2 (d, 3H), 7.57-7.09 (m, 24H), 6.86 (d, IH) d, 2 H), 1.69 (s, 6 H) m / z = 727.32
(C ₅₆ H ₄₁ N = 727.95) 3 2H), 7.88 (d, 1H), 7.75-7.74 (d, 3H), 7.57-7.08 (m, 27H) 6.86 (d, 2H) m / z = 687.29
(C ₅₃ H ₃₇ N = 687.89) 4 (d, 3H), 7.57-7.09 (m, 24H), 6.86 (d, IH) d, 2 H), 1.69 (s, 6 H) m / z = 817.33
(C ₆₂ H ₄₃ N = 818.03) 5 2H), 7.90-7.86 (d, 3H), 7.74 (d, IH), 8.04 (d, 7.57-7.09 (m, 25H), 6.86 (d, 2H), 1.69 (s, 6H) m / z = 763.32
(C ₅₉ H ₄₁ NO = 763.98) 6 (d, 1H), 8.04 (d, 1H), 7.90-7.86 (d, 3H), 7.75-7.74 6.98 (d, 1 H), 6.76 (d, 1 H), 1.69 (s, 6 H) m / z = 727.32
(C ₅₆ H ₄₁ N = 727.95) 7 8.27 (d, 1H), 8.17 (d, 1H), 8.11 (d, 1H), 7.75-7.37 (m, 25H), 7.26-7.10 m, 7H), 6.86 (d, 2H) m / z = 737.31
(C ₅₇ H ₃₉ N = 737.95) 8 1H), 8.02 (d, IH), 8.02 (d, IH), 8.24 (d, , 7.98 (d, IH), 7.75-7.37 (m, 33H), 6.86 (d, 2H) m / z = 877.33
(C ₆₇ H ₄₃ NO = 878.09) 9 8.17 (d, 1H), 8.11 (d, 1H), 7.90-7.86 (d, 2H), 7.75-7.37 (m, , 34H) m / z = 853.37
(C ₆₆ H ₄₇ N = 854. 11)

<Experimental Example 1>

Experimental Example 1-1.

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

([1,1'-biphenyl] -4-yl) -N4, N4'-di (naphthalen-1-yl) - [ 1,1'-biphenyl] -4,4'-diamine (NPB) (300 ANGSTROM) was vacuum-deposited to form a hole transport layer.

Subsequently, the following compound 1 was vacuum deposited on the hole transport layer to a thickness of 100 ANGSTROM to form an electron blocking layer.

Subsequently, BH and BD were vacuum deposited on the electron suppression layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of the lithium fluoride of the cathode was 0.3 Å / sec and the deposition rate of the aluminum was 2 Å / sec. To 5 x 10 &lt; -6 &gt; torr. Thus, an organic light emitting device was fabricated.

Experimental Example 1-2

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 2 was used instead of Compound 1 in Experimental Example 1-1.

Experimental Example 1-3

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

Experimental Examples 1-4

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 6 was used instead of Compound 1 in Experimental Example 1-1.

Experimental Examples 1-5

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

Experimental Example 1-6

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 9 was used instead of Compound 1 in Experimental Example 1-1.

Experimental Example 1-7

The same experiment was conducted except that the following compound TCTA was used as an electron blocking layer in Experimental Example 1-1 and Compound 1 was used instead of NPB as a hole transporting layer.

Experimental Examples 1-8

In the same manner as in Example 1-1 except that TCTA was used as an electron blocking layer and Compound 2 was used instead of NPB as a hole transport layer,

Experimental Examples 1-9

The same experiment was conducted except that TCTA was used as the electron blocking layer in Experimental Example 1-1 and Compound 3 was used instead of NPB as the hole transporting layer.

Experimental Example 1-10

The same experiment was conducted except that TCTA was used as an electron blocking layer in Experimental Example 1-1 and Compound 5 was used instead of NPB as a hole transporting layer.

Experimental Example 1-11

The same experiment was performed except that TCTA was used as an electron blocking layer in Experimental Example 1-1 and Compound 7 was used instead of NPB as a hole transporting layer.

Experimental Example 1-12

The same experiment was performed except that TCTA was used as the electron blocking layer in Experimental Example 1-1 and Compound 8 was used instead of NPB as the hole transporting layer.

<Comparative Example>

Comparative Example 1-1

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound EB 1 was used instead of Compound 1 in Experimental Example 1-1.

Comparative Example 1-2

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound EB 2 was used instead of Compound 1 in Experimental Example 1-1.

Comparative Example 1-3

The same experiment was conducted except that HT 1 was used as the hole transporting layer in Experimental Example 1-7.

The results shown in Table 2 were obtained when a current was applied to the organic light-emitting device manufactured by Experimental Examples 1-1 to 1-6 and Comparative Examples 1-1 and 1-2.

compound
(Electron blocking layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1-1 Compound 1 3.65 5.55 (0.139, 0.051) Experimental Example 1-2 Compound 2 3.72 5.48 (0.138, 0.052) Experimental Example 1-3 Compound 4 3.77 5.41 (0.138, 0.051) Experimental Examples 1-4 Compound 6 3.78 5.42 (0.137, 0.051) Experimental Examples 1-5 Compound 7 3.89 5.33 (0.136, 0.051) Experimental Example 1-6 Compound 9 3.84 5.37 (0.136, 0.051) Comparative Example 1-1 EB 1 4.36 4.98 (0.138, 0.066) Comparative Example 1-2 EB 2 4.42 4.84 (0.138, 0.067)

As shown in Table 2, the organic light emitting devices comprising the compounds of Experimental Examples 1-1 to 1-6 exhibited lower voltage and higher efficiency than Comparative Examples 1-1 and 1-2.

The compound represented by the formula (1) according to the present invention has excellent electron suppression ability, exhibits low voltage and high efficiency, and can be applied to organic light emitting devices.

The results shown in Table 3 were obtained when current was applied to the organic light-emitting devices fabricated according to Experimental Examples 1-7 to 1-12 and Comparative Examples 1-3.

compound
(Hole transport layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1-7 Compound 1 4.53 5.88 (0.138, 0.051) Experimental Examples 1-8 Compound 2 4.66 5.61 (0.137, 0.051) Experimental Examples 1-9 Compound 3 4.67 5.68 (0.138, 0.051) Experimental Example 1-10 Compound 5 4.68 5.62 (0.137, 0.051) Experimental Example 1-11 Compound 7 4.61 5.75 (0.136, 0.051) Experimental Example 1-12 Compound 8 4.75 5.45 (0.136, 0.051) Comparative Example 1-3 HT 1 5.02 5.12 (0.138, 0.057)

As shown in Table 3, the organic light emitting device made of the compound of Experimental Examples 1-7 to 1-12 exhibits lower voltage and higher efficiency than the organic light emitting device used in Comparative Example 1-3.

Accordingly, it has been confirmed that the compound represented by the formula according to the present invention exhibits low voltage and high efficiency due to its excellent electron transporting ability as well as electron suppressing ability, and is applicable to organic light emitting devices.

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

Claims (14)

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

In Formula 1,
Q is a condensed aromatic polycyclic group of C ₁₀ to C ₃₀ ,
L ₁ is a direct bond; A substituted or unsubstituted C ₆ to C ₄₀ arylene group; Or a substituted or unsubstituted C ₂ to C ₄₀ heteroarylene group,
R ₁ to R ₄ are the same or different and are each independently hydrogen; A halogen, an amino group, a nitrile group, a nitro group, a cycloalkyl group of C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl groups, C ₁ to C ₄₀ alkoxy groups, C ₃ to C ₄₀ of a, C ₂ to C ₄₀ A C ₃ to C ₄₀ cycloalkyl group which is unsubstituted or substituted with at least one group selected from the group consisting of a heterocycloalkyl group, a C ₆ to C ₄₀ aryl group and a C ₂ to C ₄₀ heteroaryl group; A halogen, an amino group, a nitrile group, a nitro group, a cycloalkyl group of C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl groups, C ₁ to C ₄₀ alkoxy groups, C ₃ to C ₄₀ of a, C ₂ to C ₄₀ a heterocycloalkyl group, an aryl group of C ₆ to C ₄₀ aryl group and a C ₂ to C ₄₀ by at least one group selected from the heteroaryl group consisting of a substituted or unsubstituted C ₆ to C ₄₀ of the; And a halogen, an amino group, a nitrile group, a nitro group, C ₁ to C ₄₀ alkyl group, C ₂ to C ₄₀ alkenyl groups, C ₁ to C ₄₀ alkoxy groups, C ₃ to C ₄₀ cycloalkyl group, C ₂ to about C ₄₀ heterocycloalkyl group, C ₆ to C ₄₀ aryl group and a C ₂ to C ₄₀ by at least one group selected from the heteroaryl group consisting of groups selected from the group consisting of a heteroaryl, a substituted or unsubstituted C ₂ to C ₄₀ of ,
Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₄₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₄₀ heteroaryl group,
m is an integer of 0 to 16,
n and p are each an integer of 0 to 4,
q is an integer of 0 to 5,
When m, n, p and q are each 2 or more, the substituents in the parentheses are the same as or different from each other. The method according to claim 1,
Wherein Q is any one of naphthalene, phenanthrene, triphenylene and pyrene. The method according to claim 1,
And Q is an endo or exo bond direction. The method according to claim 1,
Wherein L &lt; _{1 &gt;} is a direct bond or a phenyl group. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of Formulas 2 to 7:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above Chemical Formulas 2 to 7, the substituent is as defined in Chemical Formula 1,
L ₂ is a direct bond; A substituted or unsubstituted C ₆ to C ₃₄ arylene group; Or a substituted or unsubstituted C ₂ to C ₃₄ heteroarylene group. The method according to claim 1,
Wherein the compound of formula (I) is selected from the following compounds:

1. An organic light-emitting device comprising a cathode, an anode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes a compound of Formula 1 according to any one of claims 1 to 6. The method of claim 7,
Wherein the organic compound layer comprising the compound of Formula 1 is a hole transport layer or an electron blocking layer. The method of claim 7,
Wherein the organic material layer comprises a light emitting layer comprising a compound represented by the following formula (8): &lt; EMI ID =
[Chemical Formula 8]

In Formula 8,
Ar ₃ is a benzofluorene skeleton, a fluoranthene skeleton, a pyrene skeleton or a chrysene skeleton,
L ₃ is a single bond, a C ₆ to C ₃₀ aromatic hydrocarbon group or a C ₅ to C ₃₀ heterocyclic group,
R ₅ and R ₆ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₃₀ aromatic hydrocarbon group, a substituted or unsubstituted C ₅ to C ₃₀ heterocyclic group, a substituted or unsubstituted A C ₁ to C ₃₀ alkyl group and a substituted or unsubstituted C ₇ to C ₃₀ aralkyl group, R ₅ and R ₆ may be bonded to each other to form a saturated or unsaturated ring,
r is an integer of 1 or more,
When r is 2 or more, R ₅ are the same as or different from each other, and R ₆ is the same as or different from each other. The method of claim 9,
Wherein Ar ₃ is a pyrene skeleton, L- ₃ is a single bond, R ₅ and R ₆ are aryl groups substituted with -GeRaRbRc, and r is 2. The method of claim 7,
Wherein the organic material layer comprises a compound represented by the following formula (9)
[Chemical Formula 9]

In Formula 9,
R ₉ represents a substituted or unsubstituted 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Phenanthryl group, 9-phenanthryl group, 1-naphthacene group, 2-naphthacene group, 9-naphthacene group, 1-pyrenyl group, Methyl-1-naphthyl group or a 4-methyl-1-

ego,
R ₁₀ represents a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Naphthacenylene group, 1-naphthacenylene group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenyl group, P-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3- Methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenyl group, 4 " And a 3-fluorantheny group,
R ₇ to R ₈ are the same or different and each independently represents a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, Or an arylthio group having 5 to 50 unsubstituted nuclear atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group,
s1 and s2 are integers of 0 to 4, respectively. The method of claim 11,
Wherein R ₉ and R ₁₀ are the same or different from each other, and each independently is a 1-naphthyl group or a 2-naphthyl group, and s 1 and s 2 are 0. The method of claim 9,
Wherein the light emitting layer comprises a compound represented by the following formula (9): &lt; EMI ID =
[Chemical Formula 9]

In Formula 9,
R ₉ represents a substituted or unsubstituted 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Phenanthryl group, 9-phenanthryl group, 1-naphthacene group, 2-naphthacene group, 9-naphthacene group, 1-pyrenyl group, Methyl-1-naphthyl group or a 4-methyl-1-

ego,
R ₁₀ represents a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, a 1-phenanthryl group, a 2-phenanthryl group, Naphthacenylene group, 1-naphthacenylene group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenyl group, P-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3- Methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenyl group, 4 " And a 3-fluorantheny group,
R ₇ to R ₈ are the same or different and each independently represents a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, Or an arylthio group having 5 to 50 unsubstituted nuclear atoms, a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group,
s1 and s2 are integers of 0 to 4, respectively. 14. The method of claim 13,
Wherein Ar ₃ is a pyrene skeleton, L ₃ is a single bond, R ₅ and R ₆ are aryl groups substituted with -GeRaRbRc, r is 2,
R ₉ and R ₁₀ in Formula 9 are the same as or different from each other, and each independently is a 1-naphthyl group or a 2-naphthyl group, and s 1 and s 2 are 0.

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