KR102179709B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

A compound and an organic light-emitting device containing the same TECHNICAL FIELD

The present invention relates to a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0035658 filed with the Korean Intellectual Property Office on March 28, 2018, the entire contents of which are incorporated herein.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer has a multilayer structure made of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an 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 excitons are formed when the injected holes and electrons meet. It glows when it falls to the ground.

Development of a new material for the organic light emitting device as described above is continuously required.

Korean Patent Application Publication No. 10-2008-0096733

An object of the present specification is to provide an organic light-emitting device having a low driving voltage, high luminous efficiency, or good lifetime characteristics by including the compound represented by Formula 1.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

X is S or O,

X1 to X3 are each independently N or CH, and at least two of X1 to X3 are N,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

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

Y is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkenyl group,

n is an integer from 0 to 7, and when n is 2 or more, R is the same as or different from each other,

m is an integer from 0 to 7, and when m is 2 or more, Y is the same as or different from each other.

In addition, an exemplary embodiment of the present specification is an organic light-emitting device including a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer is represented by Formula 1 above. It provides an organic light-emitting device comprising the compound to be displayed.

The compounds described herein can be used as a material for an organic material layer of an organic light-emitting device. In one embodiment, the compound described in the present specification may be used as a hole injection, hole transport, hole injection and hole transport, light emission, electron transport or electron injection material.

In some exemplary embodiments, the efficiency of the organic light emitting device including the compound of the present invention may be improved.

In some embodiments, the driving voltage of the organic light-emitting device including the compound of the present invention may be lowered.

In some exemplary embodiments, the lifespan characteristics of the organic light-emitting device including the compound of the present invention may be improved.

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 device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 I did it.
3 shows a substrate 1, an anode 2, a hole injection layer 5, an electron blocking layer 9, a light emitting layer 7, an electron transport layer 8, an electron injection layer 10, and a cathode 4. It shows an example of the formed organic light emitting device.

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

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

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site bonded to another substituent or a bonding portion.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The position at which the substituent is substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position at which the substituent can be substituted. When there are two or more substituents, the two or more substituents may be the same as or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Hydroxy group; Alkyl group; Aralkyl group; Alkoxy group; Alkenyl group; Aryloxy group; Aryl group; And a heteroaryl group substituted or unsubstituted with at least one group selected from the group consisting of, or substituted or unsubstituted with a group to which at least two groups selected from the group are linked. For example, the arylalkenyl group may be an alkenyl group, or an aryl group may be interpreted as a substituted alkenyl group. Examples of the group to which three substituents are connected include an aryl group substituted with a heteroaryl group substituted with an aryl group, an aryl group substituted with an aryl group substituted with a heteroaryl group, and a heteroaryl group substituted with an aryl group substituted with a heteroaryl group.

As an example, in the present specification, the term "substituted or unsubstituted" refers to deuterium; Alkyl group; Aralkyl group; Alkenyl group; Aryl group; And a heteroaryl group substituted or unsubstituted with at least one group selected from the group consisting of, or substituted or unsubstituted with a group to which at least two groups selected from the group are linked.

As another example, in the present specification, the term "substituted or unsubstituted" refers to deuterium; Aryl group; And a heteroaryl group substituted or unsubstituted with at least one group selected from the group consisting of, or substituted or unsubstituted with a group to which at least two groups selected from the group are linked.

In the present specification, examples of the halogen group include a fluoro group, a chloro group, a bromo group, or an iodo group.

In the present specification, the alkoxy group refers to a group in which an alkyl group is bonded to an oxygen atom, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. According to an exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 6 carbon atoms. 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 iso-amyloxy group, and a hexyloxy group.

In the present specification, the aryloxy group refers to a group in which an aryl group is bonded to an oxygen atom, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. According to an exemplary embodiment, the aryloxy group has 6 to 25 carbon atoms. Specific examples of the aryloxy group include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethylphenoxy group, 2,4,6-trimethylphenoxy group, 3-biphenyloxy group, 1- Naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 2-anthracenyloxy group, 9-anthracenyloxy group, 1-phenanthrenyloxy group, 3-phenanthrenyloxy group, 9-phenanthrenyloxy group There are times and so on.

In the present specification, the alkyl group refers to a linear or branched hydrocarbon group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, n-pentyl, isopentyl, neopentyl , tert-pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, octyl, n-octyl, tert- Octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5- Methylhexyl, 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 alkenyl group represents a linear or ground unsaturated hydrocarbon group including a carbon-carbon double bond, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to an exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. Specific examples include ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl, and n-hexenyl, but are not limited thereto.

In the present specification, an aryl group means wholly or partially unsaturated substituted or unsubstituted monocyclic or polycyclic. Although the number of carbon atoms is not particularly limited, it is preferably 6 to 60 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 40 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto. The polycyclic aryl group is a naphthyl group, anthracenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenalenyl group, pyrenyl group, tetrasenyl group, chrysenyl group, pentacenyl group, It may be a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirofluorenyl group, and the like, but is not limited thereto.

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

,

,

,

,

,

,

및

등이 있으나, 이에 한정되지 않는다.The substituted fluorenyl group is

,

,

,

,

,

,

And

And the like, but are not limited thereto.

In the present specification, the heteroaryl group is a cyclic group including at least one of N, O and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 2 to 20 carbon atoms. Examples of the heteroaryl group include a thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, Triazinyl group, triazolyl group, acridinyl group, carbolinyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group , Pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl Group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, phenanthrolinyl group, thiazolyl group, isoxa There are a zolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenoxazinyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

The description of the aryl group described above may be applied to the aryl group in the aralkyl group and the aryloxy group.

An exemplary embodiment of the present invention provides a compound represented by Chemical Formula 1.

In the exemplary embodiment of the present specification, X1 and X2 are each N, and X3 is CH.

In the exemplary embodiment of the present specification, X1 and X3 are each N, and X2 is CH.

In the exemplary embodiment of the present specification, X2 and X3 are each N, and X1 is CH.

In the exemplary embodiment of the present specification, X1 to X3 are each N.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; Or a terphenyl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Or terphenyl group.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted C2-C24 heteroaryl group.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or a substituted or unsubstituted C 2 to C 18 heteroaryl group.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 13 carbon atoms; Or a substituted or unsubstituted C 2 to C 12 heteroaryl group.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.

In an exemplary embodiment of the present specification, Y is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted C2 to C10 alkenyl group.

In the exemplary embodiment of the present specification, Y is hydrogen or deuterium.

In the exemplary embodiment of the present specification, n is 0.

In the exemplary embodiment of the present specification, n is 1.

In the exemplary embodiment of the present specification, n is 2.

In the exemplary embodiment of the present specification, n is 3.

In the exemplary embodiment of the present specification, m is 0.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 2.

[Formula 2]

In Formula 2,

The definitions of X, X1 to X3, Ar1, Ar2, R, Y, m, and n are as defined in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 3.

[Formula 3]

In Chemical Formula 3,

The definitions of X, X1 to X3, Ar1, Ar2, R, Y, m, and n are as defined in Formula 1.

In an exemplary embodiment of the present specification, Formula 2 is represented by the following Formula 2-A.

[Formula 2-A]

In Formula 2-A,

The definitions of X, X1 to X3, Ar1, Ar2, Y and m are as defined in Formula 2,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted C2-C24 heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or a substituted or unsubstituted C 2 to C 18 heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 13 carbon atoms; Or a substituted or unsubstituted C 2 to C 12 heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.

In an exemplary embodiment of the present specification, R1 and R2 are hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.

In an exemplary embodiment of the present specification, Chemical Formula 3 is represented by Chemical Formula 3-A.

[Formula 3-A]

In Formula 3-A,

The definitions of X, X1 to X3, Ar1, Ar2, Y and m are as defined in Formula 3,

R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted C2-C24 heteroaryl group.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or a substituted or unsubstituted C 2 to C 18 heteroaryl group.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 13 carbon atoms; Or a substituted or unsubstituted C 2 to C 12 heteroaryl group.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.

In the exemplary embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following structures.

In the exemplary embodiment of the present specification, the compound represented by Formula 3 is any one selected from the following structures.

The compound of Formula 1 according to the present specification may be prepared as shown in the following General Formula 1.

[General Formula 1]

In the general formula 1, the definitions of X1 to X3, X, R, Y, Ar1, Ar2, m and n are as defined in Chemical Formula 1.

Formula 1 is an example of a method of forming the compound of Formula 1, and the synthesis method of Formula 1 is not limited to Formula 1, and may be performed by any method known in the art.

The present specification provides an organic light-emitting device including the compound represented by Chemical Formula 1.

An exemplary embodiment of the present specification is an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer is a compound represented by Formula 1 It provides an organic light emitting device comprising a.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention is a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes as an organic material layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron injection and transport at the same time. It may have a structure including a layer or the like.

In the exemplary embodiment of the present specification, the organic material layer includes an electron injection layer; Electron transport layer; Or a layer that simultaneously injects and transports electrons, the electron injection layer; Electron transport layer; Alternatively, the layer that simultaneously injects and transports electrons includes the compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 above. In this case, when the weight of the light emitting layer is 100 parts by weight, the content of the compound represented by Formula 1 is 30 parts by weight to 100 parts by weight; 50 to 100 parts by weight; Or 70 parts by weight to 100 parts by weight.

In the exemplary embodiment of the present specification, the thickness of the light emitting layer including the compound represented by Formula 1 is 20 nm to 60 nm, preferably 30 nm to 50 nm.

In the exemplary embodiment of the present specification, the light emitting layer including the compound of Formula 1 further includes a host. When the weight of the light emitting layer is 100 parts by weight, the sum of the weight parts of the compound of Formula 1 and the host is 50 to 100 parts by weight; Or 70 parts by weight to 100 parts by weight.

When the emission layer includes two or more types of hosts, the driving voltage, luminous efficiency, and/or life characteristics of the device may be further improved, and in particular, life characteristics may be greatly improved.

As the host, a condensed aromatic ring derivative or a heterocyclic-containing compound may be used. The condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladders. Type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

In the exemplary embodiment of the present specification, the host may be a carbazole derivative.

In the exemplary embodiment of the present specification, the host may be represented by Formula B below.

[Formula B]

In Formula B,

Ar11 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar12 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or heteroaryl group,

L11 is a direct bond; A substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent heteroaryl group,

m1 is an integer from 0 to 8,

When m1 is 2 or more, Ar12 is the same as or different from each other.

In an exemplary embodiment of the present specification, Formula B is represented by the following Formula B-1.

[Formula B-1]

In the formula B-1,

The definitions of Ar11, Ar12 and L11 are as defined in Formula B,

Ar13 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar14 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L12 is a direct bond; A substituted or unsubstituted divalent aryl group; Or a substituted or unsubstituted divalent heteroaryl group,

k and p are each independently an integer of 0 to 7,

When k is 2 or more, Ar12 is the same as or different from each other,

When p is 2 or more, Ar14 is the same as or different from each other.

In the exemplary embodiment of the present specification, Ar11 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In the exemplary embodiment of the present specification, Ar11 is an aryl group unsubstituted or substituted with an aryl group or a heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.

In the exemplary embodiment of the present specification, Ar11 is a phenyl group; Or a biphenyl group.

In the exemplary embodiment of the present specification, Ar13 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In the exemplary embodiment of the present specification, Ar13 is an aryl group unsubstituted or substituted with an aryl group or a heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.

In the exemplary embodiment of the present specification, Ar13 is a phenyl group; Or a biphenyl group.

In the exemplary embodiment of the present specification, Ar12 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In the exemplary embodiment of the present specification, Ar12 is hydrogen; heavy hydrogen; Alkyl group; An aryl group unsubstituted or substituted with an aryl group or a heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.

In the exemplary embodiment of the present specification, Ar12 is hydrogen; Methyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted carbazolyl group.

In the exemplary embodiment of the present specification, Ar12 is hydrogen; Methyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted carbazolyl group.

In the exemplary embodiment of the present specification, Ar12 is hydrogen; Or a carbazolyl group substituted with a phenyl group or a biphenyl group.

In the exemplary embodiment of the present specification, Ar14 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

In the exemplary embodiment of the present specification, Ar14 is hydrogen; heavy hydrogen; Alkyl group; An aryl group unsubstituted or substituted with an aryl group or a heteroaryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group or a heteroaryl group.

In the exemplary embodiment of the present specification, Ar14 is hydrogen; Methyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted carbazolyl group.

In the exemplary embodiment of the present specification, Ar14 is hydrogen.

In the exemplary embodiment of the present specification, L11 is a direct bond; A substituted or unsubstituted divalent aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 divalent heteroaryl group.

In the exemplary embodiment of the present specification, L11 is a direct bond; A divalent aryl group unsubstituted or substituted with an aryl group; Or a divalent heteroaryl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, L11 is a direct bond; Or a substituted or unsubstituted phenylene group.

In the exemplary embodiment of the present specification, L12 is a direct bond; A substituted or unsubstituted divalent aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 divalent heteroaryl group.

In the exemplary embodiment of the present specification, L12 is a direct bond; A divalent aryl group unsubstituted or substituted with an aryl group; Or a divalent heteroaryl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, L12 is a direct bond; Or a substituted or unsubstituted phenylene group.

In the exemplary embodiment of the present specification, m1 is 1.

In the exemplary embodiment of the present specification, k is 0.

In the exemplary embodiment of the present specification, p is 0.

In the exemplary embodiment of the present specification, Formula B is any one selected from the following structures.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes a compound represented by Formula 1, and the emission layer further includes a dopant. In one embodiment, when the weight of the light emitting layer is 100 parts by weight, the content of the dopant is 1 to 30 parts by weight.

In the exemplary embodiment of the present specification, the emission wavelength of the dopant may be green, red, blue, etc., but is not limited thereto. The dopant may be a phosphorescent dopant or a fluorescent dopant.

In the exemplary embodiment of the present specification, the dopant may be an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, etc., but is not limited thereto. As the aromatic amine derivative, as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group may be used. As the styrylamine compound, a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used. Examples of the styrylamine compound include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. The metal complex may be an iridium complex or a platinum complex, but is not limited thereto.

In an exemplary embodiment of the present specification, the dopant is an iridium complex.

In the exemplary embodiment of the present specification, the organic material layer includes a hole injection layer; Hole transport layer; Or a layer for simultaneously injecting and transporting holes, the hole injection layer; Hole transport layer; Alternatively, the layer for simultaneously injecting and transporting holes includes the compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the organic light emitting device 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 the exemplary embodiment of the present specification, the organic light emitting device 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.

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

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

The structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3.

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. In this structure, the compound of Formula 1 is included in the light-emitting layer (3).

FIG. 2 shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 I did it. In this structure, the compound of Formula 1 is included in the light-emitting layer 7.

3 shows a substrate 1, an anode 2, a hole injection layer 5, an electron blocking layer 9, a light emitting layer 7, an electron transport layer 8, an electron injection layer 10, and a cathode 4. It shows an example of the formed organic light emitting device. In this structure, the compound of Formula 1 is included in the light-emitting layer 7.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound of Formula 1 above.

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition method (PVD, physical vapor deposition) such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate. It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. 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 of 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. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.

In the exemplary embodiment of the present specification, when the compound of Formula 1 is included in the one or more organic material layers, materials other than the compound of Formula 1 may be the same or different from each other. When the organic light emitting device includes a plurality of organic material layers, the plurality of organic material layers may be formed of the same material or different materials.

As the anode material, it is preferable to use a material having a large work function so that holes can be smoothly injected 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); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable to use a material having a small work function to facilitate electron injection into the organic material layer as the cathode material. 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; 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 received from an electrode into an adjacent layer. The hole injection material has the ability to transport holes, and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and transfer of excitons generated in the light emitting layer to the electron injection layer or electron injection material. It is preferable to use a compound that prevents and has excellent thin film formation ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, but are not limited thereto.

The hole transport layer is a layer that transports holes injected from the hole injection layer to the emission layer. The hole transport material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion.

The electron blocking layer is a layer that prevents excess electrons passing through the emission layer from moving in the direction of the hole transport layer. The electron blocking material is preferably a material having a lower LUMO (Lowest Unoccupied Molecular Orbital) level than the hole transport layer, and may be selected as an appropriate material in consideration of the energy level of the surrounding layer. In one embodiment, an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto.

The light emitting layer is a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, and may include a light emitting material having good quantum efficiency for fluorescence or phosphorescence. Specific examples of the light-emitting material include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

In the exemplary embodiment of the present specification, the organic material layer may include two or more emission layers, and materials included in the two or more emission layers are the same or different from each other.

The hole blocking layer serves to prevent holes from entering the cathode through the emission layer in the driving process of the organic light emitting device. It is preferable to use a material having a very low level of Highest Occupied Molecular Orbital (HOMO) as the hole blocking material. The hole blocking material may be specifically TPBi, BCP, CBP, PBD, PTCBI, BPhen, etc., but is not limited thereto.

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 well from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Examples of the electron transport material include naphthalene derivatives; Triazine derivatives; Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired negative electrode material as used according to the prior art.

The electron injection layer is a layer for injecting electrons received from an electrode into the light emitting layer. The electron injection material has an ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and prevents movement of excitons generated in the light emitting layer to the hole injection layer, In addition, it is preferable to use a compound excellent in thin film forming ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

In one embodiment, the electron injection layer further includes an n-type dopant. The n-type dopant may be an organic material or an inorganic material. When the n-type dopant is an inorganic material, the inorganic material may be an alkali metal such as Li, Na, K, Rb or Cs; Alkaline earth metals such as Be, Mg, Ca, Sr and Ba; It may be a rare earth metal such as La, Ce, Pr, Nd, Sm, Eu, Tb, Th, Gd or Mn. When the n-type dopant is an organic material, the organic material may be an aliphatic hydrocarbon ring, a hetero ring, or a condensed ring thereof. When the weight of the electron injection layer is 100 parts by weight, the content of the n-type dopant may be 0.01 parts by weight to 10 parts by weight.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

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

< Preparation of compound 1>

Preparation of compound 1A

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (2-(4,4,5,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)-9H-carbazole) (10 g, 34 mmol) and 2-([1,1'-biphenyl]-2-yl)-4-([1,1'-bi Phenyl]-4-yl)-6-chloro-1,3,5-triazine (14.3 g, 34 mmol) was added to 150 mL of tetrahydrofuran (THF). 2M potassium carbonate (K ₂ CO ₃ ) 75 mL and tetrakis (triphenylphosphine) palladium (0) (Pd (PPh ₃ ) ₄ ) 0.4 g were added, followed by stirring and refluxing for 6 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized with chloroform and ethanol to prepare compound 1A (15.2 g, yield 81%, MS:[M+H] ⁺ = 551).

Preparation of compound 1

Compound 1A (15.2 g, 27.6 mmol) and 2-chlorodibenzo[b,d]thiophene (6 g, 27.6 mmol) were added to 150 mL of xylene. Sodium tert-butoxide (NaOC (CH ₃ ) ₃ ) (8 g, 82.8 mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.14 g, 1 mmol) were added, and then for 8 hours. It was stirred and refluxed. After cooling to room temperature, the resulting solid was filtered and recrystallized with chloroform and ethanol to prepare compound 1 (14.5 g, yield 72%, MS:[M+H] ⁺ = 733).

<Preparation of Compounds 2 to 14>

In the preparation of compound 1, the following compounds 2 to 14 were prepared by synthesizing in the same manner except for different types of reactants.

MS:[M+H] ⁺ (Compound 2) = 733 / MS: [M+H] ⁺ (Compound 3) = 733

MS:[M+H] ⁺ (Compound 4) = 763 / MS: [M+H] ⁺ (Compound 5) = 747

MS:[M+H] ⁺ (Compound 6) = 763 / MS:[M+H] ⁺ (Compound 7) = 717

MS:[M+H] ⁺ (Compound 8) = 717 / MS: [M+H] ⁺ (Compound 9) = 746

MS:[M+H] ⁺ (Compound 10) = 762 / MS: [M+H] ⁺ (Compound 11) = 733

MS:[M+H] ⁺ (Compound 12) = 717 / MS:[M+H] ⁺ (Compound 13) = 732

MS:[M+H] ⁺ (Compound 14) = 717

<Example 1>

A glass substrate coated with a thin film of 130 nm indium tin oxide (ITO) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

The following compound HAT-CN was thermally vacuum deposited to a thickness of 5 nm on the ITO transparent electrode prepared as described above to form a hole injection layer. The following compound HT-1 was thermally vacuum deposited to a thickness of 25 nm on the hole injection layer to form a hole transport layer. The following compound HT-2 was vacuum deposited on the hole transport layer to a thickness of 5 nm to form an electron blocking layer. Compound 1, the following compound YGH-1, and the following compound YGD-1 were vacuum-deposited to a thickness of 40 nm at a weight ratio of 44:44:12 on the electron blocking layer to form a light emitting layer. The following compound ET-1 was vacuum-deposited on the emission layer to a thickness of 25 nm to form an electron transport layer, and the following compound ET-2 and Li (lithium) were vacuum-deposited on the electron transport layer at a weight ratio of 98:2 to obtain 10 nm. A thick electron injection layer was formed. A cathode was formed by depositing aluminum to a thickness of 100 nm on the electron injection layer.

The deposition rate of the organic material in the above process was maintained at 0.04 nm / sec to 0.07 nm / sec, aluminum were deposited at speeds of 0.2 nm / sec, During the deposition, a vacuum 1 × 10 ^-7 torr to 5 × 10 ^- Maintained ⁶ torr.

<Examples 2 to 14 and Comparative Examples 1 to 6>

Devices of Examples 2 to 14 and Comparative Examples 1 to 6 were manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Example 1.

The organic light emitting device of the above Examples and Comparative Examples of 10 mA / cm ² Voltage, efficiency, luminescence color (CIE color coordinate) and lifetime were measured when the current density was applied, and the results are shown in Table 1 below. At this time, T ₉₅ refers to the time required for the luminance to decrease to 95% when the initial luminance at the current density of 20 mA/cm ² is 100%.

division compound Voltage(V) Efficiency (cd/A) CIE color coordinates T ₉₅ (h) Example 1 One 3.01 66.89 (0.459, 0.532) 156 Example 2 2 3.10 65.12 (0.460, 0.531) 172 Example 3 3 3.15 64.33 (0.461, 0.530) 168 Example 4 4 3.05 67.12 (0.458, 0.533) 165 Example 5 5 3.12 66.22 (0.459, 0.532) 159 Example 6 6 3.01 65.11 (0.459, 0.532) 172 Example 7 7 3.20 68.22 (0.458, 0.533) 152 Example 8 8 3.02 64.82 (0.459, 0.532) 145 Example 9 9 2.95 67.27 (0.460, 0.531) 153 Example 10 10 3.21 67.90 (0.459, 0.532) 157 Example 11 11 3.16 63.25 (0.460, 0.531) 192 Example 12 12 3.11 66.77 (0.459, 0.532) 176 Example 13 13 3.20 68.11 (0.461, 0.530) 166 Example 14 14 3.08 66.75 (0.460, 0.531) 176 Comparative Example 1 C1 3.81 51.11 (0.459, 0.532) 66 Comparative Example 2 C2 3.37 59.22 (0.460, 0.531) 96 Comparative Example 3 C3 3.66 40.77 (0.460, 0.531) 53 Comparative Example 4 C4 3.88 46.85 (0.459, 0.532) 42 Comparative Example 5 C5 4.21 36.55 (0.458, 0.533) 32 Comparative Example 6 C6 3.25 40.76 (0.459, 0.532) 51

From Table 1, it was confirmed that the devices of Examples 1 to 14 have lower voltage, higher efficiency, and particularly excellent lifespan characteristics compared to the devices of Comparative Examples 1 to 6. The compound according to an exemplary embodiment of the present invention has excellent characteristics of receiving electrons from the electron transport layer, so that exciton formation in the emission layer can be optimized, and as a result, when included in the emission layer, low voltage, high efficiency and long life characteristics of the device can be realized have.

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

Claims (11)

Compound represented by the following formula 2 or 3:
[Formula 2]

[Formula 3]

In Formulas 2 and 3,
X is S or O,
X1 to X3 are each independently N or CH, and at least two of X1 to X3 are N,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,
R is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Y is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkenyl group,
n is an integer of 0 to 7, and when n is 2 or more, R is the same as or different from each other,
m is an integer from 0 to 7, and when m is 2 or more, Y is the same as or different from each other. delete delete The compound of claim 1, wherein the formula 2 is represented by the following formula 2-A:
[Formula 2-A]

In Formula 2-A,
The definitions of X, X1 to X3, Ar1, Ar2, Y and m are as defined in Formula 2,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The compound of claim 1, wherein the formula 3 is represented by the following formula 3-A:
[Formula 3-A]

In Formula 3-A,
The definitions of X, X1 to X3, Ar1, Ar2, Y and m are as defined in Formula 3,
R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The compound of claim 1, wherein the compound represented by Formula 2 is any one selected from the following structures:

. The compound of claim 1, wherein the compound represented by Formula 3 is any one selected from the following structures:

. An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer is defined in any one of claims 1 and 4 to 7. An organic light-emitting device comprising the described compound. The method according to claim 8, wherein the organic material layer is an electron injection layer; Electron transport layer; Or a layer that simultaneously injects and transports electrons, the electron injection layer; Electron transport layer; Alternatively, the layer for simultaneously injecting and transporting electrons includes the compound represented by Formula 1 above. The organic light-emitting device of claim 8, wherein the organic material layer includes an emission layer, and the emission layer includes a compound represented by Chemical Formula 1. The method according to claim 8, wherein the organic material layer is a hole injection layer; Hole transport layer; Or a layer for simultaneously injecting and transporting holes, the hole injection layer; Hole transport layer; Alternatively, the layer for simultaneously injecting and transporting holes includes the compound represented by Formula 1 above.

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