KR20220166622A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same. The present invention provides a compound represented by chemical formula 1. The compound represented by chemical formula 1 can be used as a material for an organic layer of the organic light emitting device, and thus can improve efficiency, lower driving voltage, and/or improve lifespan characteristics of the organic light emitting device.

Description

Novel compound and organic light emitting device using the same {NOVEL COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present invention relates to a novel compound and an organic light emitting device including the same.

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to a novel compound and an organic light emitting device including the same.

The present invention provides a compound represented by Formula 1 below:

[Formula 1]

In Formula 1,

Two adjacent R ₁ bonds to each other to form a benzene ring, wherein the benzene ring is hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or it is substituted with a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,

the remaining R ₁ are hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,

R ₂ is hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,

R _a , R _b , and R _c are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,

n1 and n2 are each an integer from 0 to 3;

n3 is an integer from 0 to 4;

L ₁ and L ₂ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of N, O and S,

One of Ar ₁ and Ar ₂ is represented by Formula 2 below, and the other is a substituted or unsubstituted C _6-60 aryl;

[Formula 2]

In Formula 2,

X is O or S;

R _d are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,

n4 is an integer from 0 to 7;

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. to provide.

The compound represented by Chemical Formula 1 may be used as a material for an organic layer of an organic light emitting diode, and may improve efficiency, low driving voltage, and/or lifespan characteristics of an organic light emitting diode. In particular, the compound represented by Chemical Formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, electron blocking, light emission, hole blocking, electron transport, electron injection, or electron injection and transport.

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), an electron injection and transport layer (8) and a cathode (4). It shows an example of an organic light emitting device made of.

Hereinafter, in order to aid understanding of the present invention, it will be described in more detail.

또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

or

means a bond connected to another substituent.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy groups; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; Aralkenyl group; Alkyl aryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing at least one of N, O, and S atoms, or substituted or unsubstituted with two or more substituents linked to each other among the substituents exemplified above. . For example, "a substituent in 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 number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an aryl group having 6 to 25 carbon atoms or a straight-chain, branched-chain or cyclic chain alkyl group having 1 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group is specifically a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. but not limited to

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.

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

In the present specification, the alkyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

etc. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, and an acridyl group. , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group , carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), isoxazolyl group, thiadia A zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, an aralkyl group, an aralkenyl group, an alkylaryl group, and an aryl group among arylamine groups are the same as the examples of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the examples of the above-mentioned alkyl group. In the present specification, the description of the heterocyclic group described above may be applied to the heteroaryl of the heteroarylamine. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the heterocyclic group described above may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that the hydrocarbon ring is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.

The present invention provides a compound represented by Formula 1 above.

In the compound represented by Formula 1, a heterocycle containing O or S is bonded to a nitrogen atom in a parent nucleus structure in which a carbazole group is bonded to a specific position of a benzocarbazole group, thereby improving the characteristics of an organic light emitting device using the same. can

In particular, the compound represented by Formula 1 is advantageous in transporting and injecting holes by connecting a structure containing dibenzofuran or dibenzothiophene to a nitrogen atom of a carbazole or benzocarbazole structure, and is an electron pulling unit Without it, the movement of electrons can be blocked.

In addition, benzocarbazole formed by condensation with each other at a specific position of adjacent R ₁ of the substituents of Formula 1 has an appropriate HOMO energy level and triplet energy as a p-type host, and energy transfer to the red dopant through combination with other hosts has an advantageous structure.

Therefore, when applied as an electron blocking layer for injecting holes in contact with the light emitting layer or a host for transporting holes in the light emitting layer, better light emitting characteristics can be exhibited, thereby improving quantum efficiency and lifetime along with low voltage characteristics. .

In Formula 1, the compound represented by Formula 1 may be represented by Formula 1-1 or 1-2 according to the specific position at which the naphthalene ring is bonded in the benzocarbazole group:

[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,

R _a , R _b , R _c , L ₁ , L ₂ , Ar ₁ and Ar ₂ are as defined in claim 1,

R' are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,

n' is an integer from 0 to 6;

Specifically, the compound represented by Chemical Formula 1 may be represented by any one of Chemical Formulas 1-3 to 1-10:

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

In Formulas 1-3 to 1-10,

R _a , R _b , R _c , L ₁ , L ₂ , Ar ₁ , Ar ₂ , R', and n' are as defined in Chemical Formulas 1-1 and 1-2 above.

More specifically, the compound represented by Formula 1 may be represented by Formula 1-11 or 1-12:

[Formula 1-11]

[Formula 1-12]

In Formulas 1-11 and 1-12,

R _a , R _b , R _c , L ₁ , L ₂ , Ar ₁ , Ar ₂ , R', and n' are as defined in Chemical Formulas 1-1 and 1-2 above.

In addition, the compound represented by Chemical Formula 1 may be represented by any one of Chemical Formulas 1-11a to 1-11c and Chemical Formulas 1-12a to 1-12c:

[Formula 1-11a]

[Formula 1-11b]

[Formula 1-11c]

[Formula 1-12a]

[Formula 1-12b]

[Formula 1-12c]

In Formulas 1-11a to 1-11c and Formulas 1-12a to 1-12c,

L ₁ , L ₂ , Ar ₁ , and Ar ₂ are as defined in Chemical Formulas 1-1 and 1-2,

Re are each independently hydrogen; or deuterium;

Rf are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S.

Meanwhile, in Formula 1, specifically, two adjacent R ₁ are bonded to each other to form a benzene ring, wherein the benzene ring is hydrogen; heavy hydrogen; substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl; Or a substituted or unsubstituted C _5-30 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S, C _8-20 heteroaryl, or C _12-18 heteroaryl. may have been

In addition, among R ₁ , the other one not forming a benzene ring is hydrogen; heavy hydrogen; substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl; Or a substituted or unsubstituted C _5-30 heteroaryl, C _8-20 heteroaryl, or C _12-18 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. there is.

Preferably, in Formula 1, two adjacent R ₁ bonds to each other to form a benzene ring substituted with hydrogen or deuterium, and the remaining R ₁ may be hydrogen or deuterium.

Meanwhile, in Formula 1, specifically R ₂ is hydrogen; heavy hydrogen; substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl; Or a substituted or unsubstituted C _5-30 heteroaryl, C _8-20 heteroaryl, or C _12-18 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. there is.

Preferably, in Formula 1, R ₂ may be hydrogen, deuterium, phenyl, or deuterium-substituted phenyl.

Meanwhile, in Formula 1 and Formulas 1-1 to 1-12, specifically R _a , R _b , and R _c are each hydrogen; heavy hydrogen; substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl; Or a substituted or unsubstituted C _5-30 heteroaryl, C _8-20 heteroaryl, or C _12-18 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. there is.

Preferably, in Formula 1 and Formulas 1-1 to 1-12, R _a , R _b , and R _c may each be hydrogen, deuterium, phenyl, or deuterium-substituted phenyl.

In addition, n1 and n2 may each be an integer of 0 to 2, or 0 or 1.

Also, n3 may be an integer of 0 to 3, an integer of 0 to 2, or 0 or 1.

Meanwhile, in Chemical Formulas 1-1 to 1-12, each R' is hydrogen; heavy hydrogen; substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl; Or a substituted or unsubstituted C _5-30 heteroaryl, C _8-20 heteroaryl, or C _12-18 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. there is.

Preferably, in Chemical Formulas 1-1 to 1-12, each of R' may be hydrogen, deuterium, phenyl, or deuterium-substituted phenyl.

In Formulas 1-1 to 1-12, n' may be an integer of 0 to 5, an integer of 0 or 4, an integer of 0 to 3, an integer of 0 to 2, or 0 or 1.

Meanwhile, in Formula 1 and Formulas 1-1 to 1-12, Formulas 1-11a to 1-11c, and Formulas 1-12a to 1-12c, specifically, L ₁ and L ₂ are each a single bond; Alternatively, it may be a substituted or unsubstituted C _6-30 arylene, C _6-28 arylene, C _6-25 arylene, or C _6-12 arylene.

More specifically, L ₁ and L ₂ are each a single bond; or phenylene, biphenylylene, terphenylylene, quaterphenylylene, or naphthylene.

For example, L ₁ and L ₂ are each a single bond; Or it may be displayed as any one selected from the group consisting of.

.

.

Preferably, each of L ₁ and L ₂ may be a single bond, or may be phenylene or naphthylene.

Meanwhile, in Formula 1 and Formulas 1-1 to 1-12, Formulas 1-11a to 1-11c, and Formulas 1-12a to 1-12c, specifically, one of Ar ₁ and Ar ₂ is Formula 2, and Ar The remainder of ₁ and Ar ₂ may be substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl.

In addition, in Formula 2, each of R _d is hydrogen; heavy hydrogen; substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl; Or a substituted or unsubstituted C _5-30 heteroaryl, C _8-20 heteroaryl, or C _12-18 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. there is.

Preferably, in Chemical Formula 2, each of R _d may be hydrogen or deuterium.

Specifically, n4 may be an integer of 0 to 7, an integer of 0 to 4, an integer of 0 to 2, or 0 or 1.

More specifically, one of Ar ₁ and Ar ₂ is dibenzofuranyl, dibenzothiophenyl, deuterium-substituted dibenzofuranyl, or deuterium-substituted dibenzothiophenyl represented by Formula 2 above, and Ar ₁ and Ar The remainder of ₂ may be substituted or unsubstituted C _6-30 aryl.

Preferably, one of Ar ₁ and Ar ₂ is dibenzofuranyl, dibenzothiophenyl, deuterium substituted dibenzofuranyl, or deuterium substituted dibenzothiophenyl, and the other is phenyl, naphthyl substituted phenyl, biphenyl, naphthyl, phenyl substituted naphthyl, deuterium substituted phenyl.

Meanwhile, in Chemical Formulas 1-11a to 1-11c and Chemical Formulas 1-12a to 1-12c, each of R _e is hydrogen; or deuterium.

In addition, in Chemical Formulas 1-11a to 1-11c and Chemical Formulas 1-12a to 1-12c, each of R _f is hydrogen; heavy hydrogen; substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl; Or a substituted or unsubstituted C _5-30 heteroaryl, C _8-20 heteroaryl, or C _12-18 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. there is.

Preferably, each R _f can be hydrogen, deuterium, phenyl, or deuterium substituted phenyl.

Meanwhile, the compound represented by Chemical Formula 1 may be one in which deuterium is not substituted or 1 to 44 deuterium atoms are substituted. For example, in the compound represented by Formula 1, deuterium is not substituted, or 2 to 42, or 2 to 40, or 2 to 36, or 3 to 32, or 3 to 25 , or 3 to 20, or 3 to 10 deuterium may be substituted.

Representative examples of the compound represented by Formula 1 are as follows.

.

.

Meanwhile, when the compound represented by Chemical Formula 1 is used in an organic light emitting device, it may be used together with a compound represented by Chemical Formula 3 below.

[Formula 3]

In Formula 3,

R ₃ and R ₄ are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,

p is an integer from 0 to 10;

q is an integer from 0 to 7;

L ₁ and L ₂ are each independently a single bond; or a substituted or unsubstituted C _6-60 arylene;

One of Ar ₁ and Ar ₂ is represented by Formula 4 or Formula 5, and the other is a substituted or unsubstituted C _6-60 aryl;

[Formula 4]

[Formula 5]

In Formulas 4 and 5,

R ₅ and R ₆ are each independently a substituted or unsubstituted C _6-60 aryl.

In particular, when the compound represented by Chemical Formula 3 is used in an organic light emitting device together with the compound represented by Chemical Formula 1, it is advantageous even in the case of forming an exciplex, and the characteristic effects of low voltage, high efficiency, and long life are more may appear large.

Specifically, in Formula 3, R ₃ and R ₄ are hydrogen each independently; heavy hydrogen; substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl; Or a substituted or unsubstituted C _5-30 heteroaryl, C _8-20 heteroaryl, or C _12-18 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S. there is.

Preferably, in Formula 1, R ₃ and R ₄ are Each may be hydrogen, deuterium, phenyl, or deuterium substituted phenyl.

Also, p may be an integer of 0 to 8, or an integer of 0 to 5, or an integer of 0 to 4, or an integer of 0 to 3, or an integer of 0 to 2, or 0 or 1.

Also, q may be an integer of 0 to 6, or an integer of 0 to 5, or an integer of 0 to 4, or an integer of 0 to 3, or an integer of 0 to 2, or 0 or 1.

Specifically, in Formula 3, one of Ar ₃ and Ar ₄ is Formula 4 or 5, and the other of Ar ₃ and Ar ₄ is substituted or unsubstituted C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or C _6-12 aryl.

More specifically, one of Ar ₃ and Ar ₄ may be quinazolinyl or deuterium-substituted quinazolinyl, and the other of Ar ₃ and Ar ₄ may be substituted or unsubstituted C _6-30 aryl.

Preferably, one of Ar ₃ and Ar ₄ is quinazolinyl or deuterium substituted quinazolinyl, and the other is phenyl, naphthyl substituted phenyl, biphenyl, naphthyl, phenyl substituted naphthyl, deuterium substituted phenyl can be

Representative examples of the compound represented by Formula 3 are as follows.

.

.

In addition, when the compound represented by Chemical Formula 2 together with the compound represented by Chemical Formula 1 is used in one or more organic material layers of an organic light emitting device, the weight ratio of the compound represented by Chemical Formula 1 to the compound represented by Chemical Formula 2 may be 20:80 to 80:20, or 30:70 to 70:30, or 35:65 to 65:35, or 40:60 to 60:40, preferably 45:55 to 55:45 or It could be 50:50.

Meanwhile, the compound represented by Chemical Formula 1 can be prepared by the same method as in Reaction Scheme 1 or Reaction Scheme 2 below. The preparation method may be more specific in a synthesis example to be described later.

[Scheme 1]

[Scheme 2]

In Schemes 1 and 2, R ₁ , R ₂ , R _a , R _b , R _c , L ₁ , L ₂ , Ar ₁ , Ar ₂ , n1, n2, and n3 are as defined in Formula 1 above, Q ₁ and Q ₂ are each a halogen group, preferably Cl, Br or I, more preferably Cl or Br.

Specifically, the reactions of Schemes 1 and 2 utilize the Buchwald-Hartwig reaction and bis(tri-(tert-butyl)phosphine)palladium(0) (bis(tri-(tert-butyl)phosphine)palladium(0 ), Pd(P-tBu ₃ ) ₂ ), or tetrakis(triphenylphosphine)palladium (0) (tetrakis(triphenylphosphine)palladium (0), Pd(PPh ₃ ) ₄ ), etc. ) in the presence of the compound.

In addition, the reaction is dichloromethane, ethyl acetate, diethyl ether, acetonitrile, isopropyl alcohol, acetone, tetrahydrofuran (THF), N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), toluene Or in the presence of one or more organic solvents such as xylene, sodium tert-butoxide (NaOtBu), potassium carbonate (K ₂ CO ₃ cesium carbonate (Cesium carbonate, Cs ₂ CO ₃ ) and the like.

Meanwhile, the present invention provides an organic light emitting device including the compound represented by Formula 1 above. In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1. do.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include fewer organic layers.

Meanwhile, the organic light emitting device according to the present invention may further include the compound represented by Chemical Formula 3 together with the compound represented by Chemical Formula 1. For example, an organic light emitting device according to the present invention includes a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers further includes the compound represented by Formula 1 and the compound represented by Formula 3 can do.

In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 above. Contains the indicated compounds.

Also, the organic material layer may include an electron blocking layer, and the electron blocking layer includes the compound represented by Chemical Formula 1.

Also, the organic layer may include a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1. Meanwhile, the light emitting layer may further include the compound represented by Chemical Formula 3 together with the compound represented by Chemical Formula 1.

In addition, the light emitting layer further includes a dopant compound.

In addition, the light emitting layer includes the compound of Formula 1 and a dopant.

For example, the light emitting layer includes the compound of Formula 1 and a dopant, and includes the compound of Formula 1 and the dopant in a content ratio of 100:1 to 1:1.

In addition, the light emitting layer includes the compound of Formula 1 and the dopant, and includes the compound of Formula 1 and the dopant in a content ratio of 100:1 to 2:1.

In addition, the light emitting layer includes the compound of Formula 1 and the dopant, and includes the compound of Formula 1 and the dopant in a content ratio of 100:1 to 5:1.

For example, the dopant is a metal complex.

Specifically, the dopant is an iridium-based metal complex.

In addition, the organic material layer includes a light emitting layer, the light emitting layer includes a dopant, and the dopant material is selected from the following structural formulas.

.

.

The structures specified above are not limited to dopant compounds.

In addition, the organic material layer may include a hole blocking layer, and the hole blocking layer includes the compound represented by Chemical Formula 1.

In addition, the organic material layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously injects and transports electrons, and the electron transport layer, electron injection layer, or layer that simultaneously injects and transports electrons is represented by Formula 1 above. Contains the indicated compounds.

In addition, the organic layer may include a light emitting layer and an electron blocking layer, and the light emitting layer or electron blocking layer may include the compound represented by Chemical Formula 1.

Also, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In this structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (3), an electron injection and transport layer (8) and a cathode (4). It shows an example of an organic light emitting device made of. In this structure, the compound represented by Chemical Formula 1 may be included in at least one layer of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, and the electron injection and transport layer. Specifically, the compound represented by Chemical Formula 1 may be included in the light emitting layer or electron blocking layer, for example, may be included as a host material or electron blocking layer material of the light emitting layer.

The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Chemical Formula 1. Also, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, depositing a metal or a metal oxide having conductivity or an alloy thereof on the substrate to form an anode After forming an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer thereon, depositing a material that can be used as a cathode thereon can be manufactured In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. In particular, the compound represented by Chemical Formula 1 has excellent solubility in the solvent used in the solution application method, and thus the solution application method is easy to apply. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

Accordingly, the present invention provides a coating composition comprising the compound represented by Formula 1 and a solvent.

The solvent is not particularly limited as long as it can dissolve or disperse the compound according to the present invention, and examples thereof include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o -Chlorinated solvents such as dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents, such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents, such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. alcohol and its derivatives; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butyl benzoate and methyl-2-methoxy benzoate; tetralin; and solvents such as 3-phenoxy-toluene. In addition, the above-mentioned solvent may be used alone or in combination of two or more solvents.

In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within the above range. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt / v% to 20 wt / v%.

In addition, the present invention provides a method for forming a functional layer using the coating composition described above. Specifically, coating the coating composition according to the present invention described above by a solution process; and heat-treating the coated coating composition.

In the heat treatment step, the heat treatment temperature is preferably 150 ℃ to 230 ℃. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.

In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the cathode material 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); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function so as to easily inject electrons into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and generated in the light emitting layer A compound that prevents migration of excitons to the electron injecting layer or electron injecting material and has excellent thin film formation ability is preferred. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. As a hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is a material having high hole mobility. this is suitable Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. 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, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto. Preferably, the compound according to the present invention is used as the host material. In addition, as the host material, the compound represented by Chemical Formula 3 may be further included together with the compound represented by Chemical Formula 1 according to the present invention.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, periplanthene, etc. having an arylamino group, and styrylamine compounds include substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, wherein one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but is not limited thereto. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes. Preferably, an iridium-based metal complex is used as the dopant material.

The light emitting layer may be a red light emitting layer, and when the compound according to the present invention is used as a host material, stability for electrons and holes is increased, and energy transfer from the host to the red dopant is well performed, driving voltage of the organic light emitting device, Luminous efficiency and lifetime characteristics can be improved.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by a layer of aluminum or silver.

The electron injection layer is a layer for injecting electrons from an electrode, has the ability to transport electrons, has an excellent electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes of excitons generated in the light emitting layer. A compound that prevents migration to a layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. and their derivatives, metals complex compounds and nitrogen-containing 5-membered ring derivatives, 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-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.

The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.

In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

Preparation of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[Synthesis Example]

Synthesis Example 1. Synthesis of Compound 1

Step 1) Synthesis of Compound 1-1

(11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid (15.0 g, 44.5 mmol) and 3-bromo-9H-carbazole (12.0 g, 48.9 mmol) were mixed in tetrahydrofuran (THF) in a nitrogen atmosphere. ) into 300 mL and stirred and refluxed. After that, potassium carbonate (K ₂ CO ₃ , 24.6 g, 177.9 mmol) was dissolved in 74 mL of water, added, stirred sufficiently, and tetrakis(triphenylphosphine)palladium(0) (Pd(PPh ₃ ) ₄ , 1.5 g, 1.3 mmol) was put in. After reacting for 8 hours, the mixture was cooled to room temperature, and the organic layer and the water layer were separated and the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 14.9 g of compound 1-1. (Yield 73%, MS: [M+H] ⁺ = 460)

Step 2) Synthesis of Compound 1

In a nitrogen atmosphere, compound 1-1 (15.0 g, 31.0 mmol) and 2-bromodibenzo[b,d]furan (8.4 g, 34.1 mmol) were added to 300 mL of toluene, stirred and refluxed. After that, sodium tert-butoxide (NaOBu, 4.5 g, 46.5 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, and the organic layer was separated using chloroform and water, and then the organic layer was distilled. This was dissolved in chloroform again, and after washing twice with water, the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. After the concentrated compound was purified by silica gel column chromatography, 7.6 g of Compound 1 was prepared through sublimation purification. (Yield 39%, MS: [M+H] ⁺ = 626)

Synthesis Example 2. Synthesis of Compound 2

In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid was converted to (11-([1,1'-biphenyl]-4-yl)-11H-benzo[a]carbazol Compound 2 was prepared in the same manner as in Synthesis Example 1, except that 2-bromodibenzo[b,d]furan was changed to 1-chlorodibenzo[b,d]furan as -8-yl)boronic acid. . (MS: [M+H] ⁺ = 702)

Synthesis Example 3. Synthesis of Compound 3

In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid was converted to (5-(naphthalen-2-yl)-5H-benzo[b]carbazol-2-yl)boronic acid , Compound 3 was prepared in the same manner as in Synthesis Example 1, except that 2-bromodibenzo[b,d]furan was changed to 3-bromodibenzo[b,d]furan. (MS: [M+H] ⁺ = 676)

Synthesis Example 4. Synthesis of Compound 4

In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid was converted to (5-([1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazol -2-yl) boronic acid, Compound 4 was prepared in the same manner as in Synthesis Example 1, except that 2-bromodibenzo [b, d] furan was changed to 4-chlorodibenzo [b, d] thiophene. . (MS: [M+H] ⁺ = 718)

Synthesis Example 5. Synthesis of Compound 5

In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid was converted to (6-phenyl-11-(phenyl-d5)-11H-benzo[a]carbazol-8-yl) Compound 5 was prepared in the same manner as in Synthesis Example 1, except that boronic acid was used. (MS: [M+H] ⁺ = 707)

Synthesis Example 6. Synthesis of Compound 6

In Synthesis Example 1, 3-bromo-9H-carbazole was changed to 3-bromo-5-phenyl-9H-carbazole and 2-bromodibenzo[b,d]furan was changed to 3-bromodibenzo[b,d]thiophene. Except, Compound 6 was prepared in the same manner as in Synthesis Example 1. (MS: [M+H] ⁺ = 718)

Synthesis Example 7. Synthesis of Compound 7

In Synthesis Example 1, (11-phenyl-11H-benzo [a] carbazol-8-yl) boronic acid to (9-phenyl-9H-carbazol-3-yl) boronic acid, 3-bromo-9H-carbazole The compound was prepared in the same manner as in Synthesis Example 1, except that 8-bromo-11H-benzo[a]carbazole and 2-bromodibenzo[b,d]furan were changed to 4-chlorodibenzo[b,d]furan. 7 was prepared. (MS: [M+H] ⁺ = 626)

Synthesis Example 8. Synthesis of Compound 8

In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid was converted to (9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid, 3- The synthesis example above, except that bromo-9H-carbazole was changed to 2-bromo-5H-benzo[b]carbazole and 2-bromodibenzo[b,d]furan was changed to 2-bromodibenzo[b,d]thiophene. Compound 8 was prepared in the same manner as in 1. (MS: [M+H] ⁺ = 692)

Synthesis Example 9. Synthesis of Compound 9

In Synthesis Example 1, (11-phenyl-11H-benzo [a] carbazol-8-yl) boronic acid to (7,9-diphenyl-9H-carbazol-3-yl) boronic, 3-bromo-9H-carbazole In the same manner as in Synthesis Example 1, except that 2-bromo-5H-benzo[b]carbazole and 2-bromodibenzo[b,d]furan were changed to 1-chlorodibenzo[b,d]thiophene. Compound 9 was prepared. (MS: [M+H] ⁺ = 718)

Synthesis Example 10. Synthesis of Compound 10

In Synthesis Example 1, (11-phenyl-11H-benzo [a] carbazol-8-yl) boronic acid to (9-phenyl-9H-carbazol-3-yl) boronic acid, 3-bromo-9H-carbazole Synthesis Example 1, except that 2-bromo-5H-benzo [b] carbazole and 2-bromodibenzo [b, d] furan were changed to 1- (3-chlorophenyl) dibenzo [b, d] furan. Compound 10 was prepared in the same manner as above. (MS: [M+H] ⁺ = 702)

[Example]

Example 1-1

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400 Angstrom (Å, angstrom) was placed in distilled water dissolved in detergent and washed with ultrasonic waves. At this time, Fischer Co.'s Decon ^TM CON705 product was used as a detergent, and distilled water filtered through a 0.22 μm sterilizing filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed in isopropyl alcohol, acetone, and methanol solvents for 10 minutes each, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator.

The following compound HI-A and compound LG-101 were sequentially thermally vacuum deposited to a thickness of 800 Å and 50 Å, respectively, on the prepared ITO transparent electrode to form a hole injection layer. The following compound HT-A was vacuum-deposited to a thickness of 800 Å as a hole transport layer thereon, and then the compound EB-A was thermally vacuum-deposited to a thickness of 600 Å as an electron blocking layer. Then, on the EB-A deposited film, a mixture of compound RH-A and compound 1 at a weight ratio of 1:1 as a host for the light emitting layer, and compound RD-A as a dopant were applied, and the host and dopant were mixed in a ratio of 98:2. A red light emitting layer was formed by vacuum deposition to a thickness of 400 Å by weight. Subsequently, as an electron injection and transport layer, the following compound ET-A and compound Liq were thermally vacuum deposited at a ratio of 1:1 to a thickness of 360 Å, followed by vacuum deposition of the following compound Liq to a thickness of 5 Å. A negative electrode was formed by sequentially depositing magnesium and silver to a thickness of 220 Å and aluminum to a thickness of 1000 Å at a ratio of 10:1 on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition rate of lithium fluoride on the anode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec. Maintaining 2x10 ^-7 to 5x10 ^-6 torr, an organic light emitting device was manufactured.

Examples 1-2 to 1-10

Examples 1-2 to 1- were prepared in the same manner as in Example 1-1, except that Compounds 2 to 10 listed in Table 1 were used instead of Compound 1 in the organic light emitting device of Example 1-1. An organic light emitting device of 10 was manufactured. At this time, as the light emitting layer host, a mixture of any one of the compounds 2 to 10 and the compound RH-A at a weight ratio of 1: 1 was used, and the parentheses in Table 1 refer to the weight ratio between the host compounds.

.

.

Comparative Examples 1-1 to 1-5

Comparative Examples 1-1 to 1- were prepared in the same manner as in Example 1-1, except that Compounds A to E listed in Table 1 were used instead of Compound 1 in the organic light emitting device of Example 1-1. The organic light emitting device of 5 was manufactured. At this time, as the light emitting layer host, a mixture of any one of the compounds A to E and the compound RH-A at a weight ratio of 1: 1 was used, and the parentheses in Table 1 refer to the weight ratio between the host compounds. In addition, the compounds A, B, C, D, and E used in Table 1 below are as follows.

.

.

Examples 2-1 to 2-10

In the organic light emitting device of Example 1-1, the compounds 1 to 10 described in Table 2 were used instead of the compound EB-A as an electron blocking layer, and only the compound RH-A was used as a host for the light emitting layer without mixing Compound 1. The organic light emitting diodes of Examples 2-1 to 2-10 were prepared in the same manner as in Example 1-1, except for the use.

Comparative Examples 2-1 to 2-5

In the organic light emitting device of Example 1-1, compounds A to E described in Table 2 were used instead of the compound EB-A as an electron blocking layer, and only the compound RH-A was used as a host for the light emitting layer without mixing Compound 1. The organic light emitting devices of Comparative Examples 2-1 to 2-5 were prepared in the same manner as in Example 1-1, except for the use.

[Experimental example]

Experimental Example 1

Current was applied to the organic light emitting devices manufactured in Examples 1-1 to 1-10 and Comparative Examples 1-1 to 1-5 to measure voltage, efficiency, and lifetime, and the results are shown in Table 1 below. shown in At this time, the voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and the LT97 measured the time (hr) until the initial luminance (6000 nit) decreased to 97% at a current density of 20 mA/cm ² it means.

emissive layer host
compound
(weight ratio) Voltage
(V, @10mA/cm ² ) efficiency
(cd/A, @10mA/cm ² ) Lifetime LT97 (hr, @20mA/cm ² ) Example 1-1 Compound 1: RH-A
(50:50) 4.44 22.7 110 Example 1-2 Compound 2:RH-A (50:50) 4.41 21.2 108 Examples 1-3 Compound 3:RH-A (50:50) 4.43 22.1 106 Example 1-4 Compound 4:RH-A (50:50) 4.42 21.5 112 Example 1-5 Compound 5:RH-A (50:50) 4.39 20.8 109 Example 1-6 Compound 6:RH-A (50:50) 4.34 21.8 116 Examples 1-7 Compound 7:RH-A (50:50) 4.35 20.5 108 Examples 1-8 Compound 8:RH-A (50:50) 4.36 20.8 110 Examples 1-9 Compound 9:RH-A (50:50) 4.44 21.7 106 Examples 1-10 Compound 10:RH-A (50:50) 4.32 22.4 106 Comparative Example 1-1 Compound A:RH-A (50:50) 5.43 13.1 42 Comparative Example 1-2 Compound B:RH-A (50:50) 5.12 17.1 51 Comparative Example 1-3 Compound C:RH-A (50:50) 5.38 12.6 67 Comparative Example 1-4 Compound D:RH-A (50:50) 5.23 10.7 48 Comparative Example 1-5 Compound E:RH-A (50:50) 5.14 17.3 70

As shown in Table 1, the organic light emitting device manufactured using the compound of the present invention as a material of the light emitting layer exhibits excellent characteristics in terms of efficiency, driving voltage and/or stability (lifetime) of the organic light emitting device.

In the organic light emitting device according to an embodiment of the present invention, a heterocycle including O or S is bonded to a nitrogen atom of a parent structure to which a carbazole group is bonded at a specific position corresponding to a benzene ring in a benzocarbazole group, thereby forming a benzocarbazole ring. Compound A in which a carbazole group is linked to a position corresponding to a naphthalene ring among sol groups, Compound B in which a heterocyclic ring is not bonded, or a carbazole ring containing N instead of a heterocyclic ring containing O or S is further bonded. Compound C, compound D in which the benzofuran ring is included in the linker between the benzocarbazole group and the carbazole group, or compound E in which the position of the naphthalene ring in the parent nucleus structure of the benzocarbazole group is different is used as a material for the light emitting layer. It exhibited characteristics of low voltage, high efficiency, and long lifespan compared to the manufactured organic light emitting device.

Experimental Example 2

Current was applied to the organic light emitting devices manufactured in Examples 2-1 to 2-10 and Comparative Examples 2-1 to 2-5 to measure voltage, efficiency, and lifetime, and the results are shown in Table 2 below. shown in At this time, the voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and the LT97 measured the time (hr) until the initial luminance (6000 nit) decreased to 97% at a current density of 20 mA/cm ² it means.

electronic blocking layer
compound Voltage
(V, @10mA/cm ² ) efficiency
(cd/A, @10mA/cm ² ) Lifetime LT97 (hr, @20mA/cm ² ) Example 2-1 compound 1 4.62 20.3 94 Example 2-2 compound 2 4.61 19.4 96 Example 2-3 compound 3 4.66 20.0 92 Example 2-4 compound 4 4.60 19.6 101 Example 2-5 compound 5 4.51 19.2 99 Example 2-6 compound 6 4.56 20.6 103 Examples 2-7 compound 7 4.53 18.7 99 Example 2-8 compound 8 4.52 18.1 104 Example 2-9 compound 9 4.61 19.7 93 Examples 2-10 compound 10 4.50 20.3 99 Comparative Example 2-1 compound A 5.69 11.0 33 Comparative Example 2-2 compound B 5.34 15.3 44 Comparative Example 2-3 compound C 5.50 10.2 56 Comparative Example 2-4 compound D 5.43 9.9 37 Comparative Example 2-5 compound E 5.36 14.0 61

As shown in Table 2, the organic light emitting device manufactured using the compound of the present invention as a material for the electron blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage, and/or stability (lifetime) of the organic light emitting device.

In the organic light emitting device according to an embodiment of the present invention, a heterocycle containing O or S is bonded to a nitrogen atom of a parent structure to which a carbazole group is bonded to a specific position corresponding to a benzene ring in a benzocarbazole group, thereby forming a benzocarbazole ring. Compound A in which a carbazole group is linked to a position corresponding to a naphthalene ring among sol groups, Compound B in which a heterocyclic ring is not bonded, or a carbazole ring containing N instead of a heterocyclic ring containing O or S is further bonded. Compound C, compound D in which the benzofuran ring is included in the linker between the benzocarbazole group and the carbazole group, or compound E in which the position of the naphthalene ring in the parent nucleus structure of the benzocarbazole group is different is used as the material for the electron blocking layer It exhibited characteristics of low voltage, high efficiency, and long lifespan compared to the organic light emitting device manufactured using the organic light emitting device.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: electron injection and transport layer

Claims (12)

A compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
Two adjacent R ₁ bonds to each other to form a benzene ring, wherein the benzene ring is hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or it is substituted with a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,
the remaining R ₁ are hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,
R ₂ is hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,
R _a , R _b , and R _c are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,
n1 and n2 are each an integer from 0 to 3;
n3 is an integer from 0 to 4;
L ₁ and L ₂ are each independently a single bond; or a substituted or unsubstituted C _6-60 arylene;
One of Ar ₁ and Ar ₂ is represented by Formula 2 below, and the other is a substituted or unsubstituted C _6-60 aryl;
[Formula 2]

In Formula 2,
X is O or S;
R _d are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,
n4 is an integer from 0 to 7;
According to claim 1,
The compound represented by Formula 1 is represented by Formula 1-1 or 1-2 below,
compound.
[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,
R _a , R _b , R _c , L ₁ , L ₂ , Ar ₁ and Ar ₂ are as defined in claim 1,
R' are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heteroaryl containing at least one heteroatom selected from the group consisting of N, O and S,
n' is an integer from 0 to 6;
According to claim 1,
The compound represented by Formula 1 is represented by any one of the following Formulas 1-3 to 1-10,
compound.
[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

In Formulas 1-3 to 1-10,
R _a , R _b , R _c , L ₁ , L ₂ , Ar ₁ , Ar ₂ , R', and n' are as defined in claim 2.
According to claim 1,
Two adjacent R ₁ are bonded to each other to form a benzene ring substituted with hydrogen or deuterium, and the remaining R ₁ is hydrogen or deuterium,
compound.
According to claim 1,
R ₂ is hydrogen, deuterium, or substituted or unsubstituted C _6-30 aryl;
compound.
According to claim 1,
R _a , R _b , and R _c are each hydrogen, deuterium, or substituted or unsubstituted C _6-30 aryl;
compound.
According to claim 1,
L ₁ and L ₂ are each a single bond or a substituted or unsubstituted C _6-30 arylene;
compound.
According to claim 1,
R _d are each hydrogen or deuterium;
compound.
According to claim 1,
One of Ar ₁ and Ar ₂ is dibenzofuranyl, dibenzothiophenyl, deuterium-substituted dibenzofuranyl, or deuterium-substituted dibenzothiophenyl, and the other is a substituted or unsubstituted C _6-30 aryl;
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
compound:

.
a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 10. That is, an organic light emitting element.
According to claim 11,
The organic material layer containing the compound is a light emitting layer or an electron blocking layer,
organic light emitting device.

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