KR102172575B1 - Organic light emitting device - Google Patents

Abstract

The present specification relates to an organic light emitting device having a novel structure.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2014-0116489 filed with the Korean Intellectual Property Office on September 2, 2014, the entire contents of which are incorporated herein.

The present specification provides an organic light emitting device having a novel structure.

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 is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

In order to sufficiently exhibit the excellent characteristics of the organic light emitting device described above, the internal luminous efficiency supported by the material constituting the organic material layer in the device must be high, and the external luminous efficiency must also be good. Internal luminous efficiency is related to the efficiency of light conversion that occurs in the device's hole injection material, hole transport material, luminous material, electron transport material, electron injection material, etc., and the external luminous efficiency is when light generated inside the device comes out of the device. It is related to efficiency. Reducing the loss due to absorption or reflection during the process of extracting the light generated from the inside is as important as improving the internal luminous efficiency.

J. Mater. Chem., 2009, 19, 8907-8919

An object of the present specification is to provide an organic light-emitting device to which a material capable of increasing external light efficiency is applied.

According to an exemplary embodiment of the present specification,

Board;

An anode and a cathode provided on the substrate;

One or more organic layers provided between the anode and the cathode; And

At least one of the anode and the cathode, including a light efficiency improvement layer provided on a surface opposite to the surface facing the organic layer,

The light efficiency improvement layer provides an organic light emitting device comprising a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

In Formula 1,

X ₁ is O, S, NR _a or P(=O)R _b ,

R ₁ to R ₈ are the same as or different from each other, and each independently -L ₁ -NR'R"; a group represented by the following formula (2); hydrogen; deuterium; halogen; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; already A radical group; an amide group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted alkoxy group; substituted or unsubstituted A substituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; substituted or unsubstituted boron group; substituted or unsubstituted alkylamine group; substituted or unsubstituted aralkylamine group; substituted or unsubstituted arylamine group; substituted or unsubstituted hetero Arylamine group; substituted or unsubstituted arylphosphine group; substituted or unsubstituted phosphine oxide group; substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and substituted or unsubstituted carbon number 2 to 30 It is selected from the group consisting of a monocyclic or polycyclic heteroaryl group, or at least two of the R ₁ to R ₈ are connected to each other to form an aromatic ring having 6 to 30 carbon atoms,

R _a and R _b are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted linear or branched chain having 1 to 30 carbon atoms Alkyl group of; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or the above R'and R" May be bonded to each other to form a substituted or unsubstituted ring,

L ₁ is a direct bond; A substituted or unsubstituted C 1 to C 30 linear or branched alkylene group; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; And a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,

[Formula 2]

In Formula 2,

X ₂ is O, S or NR _c ,

R ₉ to R at least one of the ₁₆ directly or is connected to structure (I) via a linking group (L _2), R ₉ to R directly or through a linking group (L ₂₎ of the ₁₆ are each independently groups which are not connected to the formula (1) or different And each independently hydrogen; heavy hydrogen; halogen; Nitrile; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or at least two of the R ₉ to R ₁₆ are connected to each other to form an aromatic ring having 6 to 30 carbon atoms,

R _c is hydrogen; heavy hydrogen; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

L ₂ is a direct bond; A substituted or unsubstituted C 1 to C 30 linear or branched alkylene group; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; And a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

The organic light emitting device according to the exemplary embodiments of the present specification provides excellent light efficiency by providing a light efficiency improvement layer including the compound represented by Formula 1 described above.

The light efficiency improvement layer may be affected by the refractive index of the material. There are various factors that affect the refractive index of a material, and in the case of an organic material, a substituent including S or P can increase the refractive index of the compound. That is, the higher the content of S or P, the higher the refractive index. According to some exemplary embodiments of the present specification, the compound represented by Formula 1 is designed in consideration of the stacking of molecules and the birefringence of small molecules including S and P, as well as O and N, thereby improving light efficiency having a high refractive index. Layers can be provided.

1 is a cross-sectional view of an organic light-emitting device according to an exemplary embodiment of the present specification.
2 is a cross-sectional view of an organic light-emitting device according to an exemplary embodiment of the present specification.
3 is a cross-sectional view of an organic light-emitting device according to an exemplary embodiment of the present specification.

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

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

In the present specification, when a member is said to be positioned “on” another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

Examples of the substituent in the present specification are described below, but are not limited thereto.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or no substituent. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected. It means that two or more of the substituents exemplified above are substituted or unsubstituted with a connected substituent. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

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

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

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the nitrogen of the amide group may be substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. 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 carbonyl group is not particularly limited, but is preferably 1 to 30 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 a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples 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-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and 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. Does not.

In the present specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; Aralkylamine group; Arylamine group; And it may be selected from the group consisting of a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

In the present specification, the alkyl group in the alkylamine, aralkylamine, alkylthioxy group, and alkylsulfoxy group is the same as the example of the aforementioned alkyl group. Specifically, the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group, and the alkyl sulfoxy group is mesyl, ethyl sulfoxy group, propyl sulfoxy group, butyl sulfoxy group. And the like, but are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. 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, and the like, but are not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ R ₁₀₂ , wherein R ₁₀₀ , R ₁₀₁ and R ₁₀₂ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; Nitrile; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

및

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

,

,

And

Etc. However, it is not limited thereto.

In the present specification, the aryl group among the aryloxy group, arylthioxy group, arylsulfoxy group, and aralkylamine group is the same as the example of the aryl group described above. Specifically, the aryloxy group includes phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyl Oxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryl Oxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, and 9-phenanthryloxy, and the arylthioxy group includes a phenylthioxy group, a 2-methylphenylthioxy group and a 4-tert-butylphenyl There are thioxy groups, and the aryl sulfoxy group includes a benzene sulfoxy group and a p-toluene sulfoxy group, but is not limited thereto.

In the present specification, in the present specification, the heteroaryl group is an atom other than carbon and contains one or more heteroatoms, and specifically, the heteroatom is one or more atoms selected from the group consisting of O, N, Se and S Can include. Although the number of carbon atoms is not particularly limited, it is preferably 2 to 30 carbon atoms. Examples of heterocyclic groups include thiophene groups, furan groups, pyrrole groups, imidazole groups, thiazole groups, oxazole groups, oxadiazole groups, triazole groups, pyridyl groups, bipyridyl groups, pyrimidyl groups, triazine groups, triazole groups, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, Isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the heteroaryl group of the heteroarylamine group may be selected from the examples of the aforementioned heteroaryl group. In the present specification, the heterocyclic group may be monocyclic or polycyclic, and condensation of aromatic, aliphatic, or aromatic and aliphatic It may be a ring, and may be selected from examples of the heteroaryl group.

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.

In the present specification, the ring is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the aryl group, except for the non-monovalent one.

In the present specification, the anti-aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.

In the present specification, the heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except that it is not monovalent.

According to an exemplary embodiment of the present specification,

Board;

An anode and a cathode provided on the substrate;

At least one organic layer provided between the anode and the cathode; And

At least one of the anode and the cathode, including a light efficiency improvement layer provided on a surface opposite to the surface facing the organic layer,

The light efficiency improvement layer provides an organic light-emitting device comprising the compound represented by Formula 1 above.

According to another exemplary embodiment of the present specification, in Formula 1, R ₁ to R ₈ are the same as or different from each other, and each independently -L ₁ -NR'R"; the group of Formula 2; hydrogen; deuterium ; Halogen; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amide group; deuterium, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group A monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms substituted or unsubstituted with one or two or more selected substituents; deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocycle An alkoxy group substituted or unsubstituted with one or two or more substituents selected from the group consisting of groups; selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Aryloxy group substituted or unsubstituted with one or two or more substituents; 1 or 2 selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Alkyl thioxy group substituted or unsubstituted with more than one kind of substituent; With one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Substituted or unsubstituted arylthioxy group; substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups Alkyl sulfoxy group; deuterium, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group and substituted or unsubstituted aryl sulfoxy group with one or two or more substituents selected from the group consisting of substituted or unsubstituted heterocyclic groups ; Deuterium, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted An alkenyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a heterocyclic group; A silyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; A boron group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An alkylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An aralkylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Arylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; A heteroarylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An arylphosphine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; A phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Straight-chain or branched having 1 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Chain alkyl group; Deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group Ring aryl group; And deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 2 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group It is selected from the group consisting of polycyclic heteroaryl groups.

According to another exemplary embodiment of the present specification, R ₁ to R ₈ are the same as or different from each other, and each independently -L ₁ -NR'R"; the group of Formula 2; hydrogen; deuterium; halogen; nitrile group ; A nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amide group; a monocyclic ring having 3 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, alkyl groups, aryl groups and heterocyclic groups Or a polycyclic cycloalkyl group; an alkoxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group An aryloxy group unsubstituted or substituted with one or two or more substituents; deuterium, an alkylthioxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an alkyl group, an aryl group, and a heterocyclic group; deuterium, An arylthioxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an alkyl group, an aryl group and a heterocyclic group; 1 or 2 or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group Alkylsulfoxy group unsubstituted or substituted with; Arylsulfoxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, alkyl groups, aryl groups, and heterocyclic groups; deuterium, alkyl groups, aryl groups and heterocycles Alkenyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of groups; Silyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, alkyl groups, aryl groups and heterocyclic groups ; A boron group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; 1 or 2 types selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group Unsubstituted or substituted with more than one substituent Alkylamine group; An aralkylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; An arylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A heteroarylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; An arylphosphine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; A phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A straight or branched alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; And it is selected from the group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group.

According to another exemplary embodiment of the present specification, R ₁ to R ₈ are the same as or different from each other, and each independently -L ₁ -NR'R"; the group of Formula 2; hydrogen; deuterium; halogen; nitrile group ; Substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl group; substituted or unsubstituted naphthyl group; substituted or unsubstituted fluorenyl group; substituted or unsubstituted carbazolyl group; substituted or unsubstituted dibenzofura Nyl group; substituted or unsubstituted triazinyl group; substituted or unsubstituted dibenzothiophene group; substituted or unsubstituted terphenyl group; substituted or unsubstituted pyridyl group; substituted or unsubstituted quinolyl group; substituted or unsubstituted A substituted pyrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted benzoquinolinyl group; a substituted or unsubstituted triphenylenyl group; A substituted phenanthroline group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted tetracenyl group; a substituted or unsubstituted benzimidazolyl group; a substituted or unsubstituted benzoxazolyl group; and a substituted or unsubstituted fluoranthenyl group; It is selected from the group consisting of a cyclic benzothiazolyl group.

According to another exemplary embodiment of the present specification, R ₁ to R ₈ are the same as or different from each other, and each independently -L ₁ -NR'R"; the group of Formula 2; hydrogen; deuterium; halogen; nitrile group ; A phenyl group unsubstituted or substituted with a halogen, nitrile group, an aryl group unsubstituted or substituted with an aryl group, or a phenyl group unsubstituted or substituted with an alkyl group or a heteroaryl group unsubstituted with an aryl group; biphenyl group unsubstituted or substituted with an aryl group; naphthyl group; alkyl group Fluorenyl group substituted with; carbazolyl group substituted with aryl group; dibenzofuranyl group; fluorenyl group substituted with aryl group; triazinyl group substituted with aryl group; dibenzothiophene group; terphenyl group; pyridyl group; quinolyl group Group; pyrenyl group; triphenylenyl group; phenanthrenyl group (phenanthrenyl); anthracenyl group unsubstituted or substituted with an aryl group; benzoquinolinyl group; phenanthroline group; fluoranthenyl group; tetrasenyl group; alkyl group or aryl group It is selected from the group consisting of a benzimidazolyl group substituted or unsubstituted with a group; a benzoxazolyl group; and a benzothiazolyl group.

According to another exemplary embodiment of the present specification, R ₁ to R ₈ are the same as or different from each other, and each independently -L ₁ -NR'R"; the group of Formula 2; hydrogen; deuterium; halogen; nitrile group ; Fluorine, nitrile group, phenyl group, pyridyl group, naphthyl group, quinolinyl group, pyrenyl group, triphenylenyl group, phenanthrenyl group, anthracenyl group substituted with biphenyl group, anthracenyl group substituted with phenyl group, anthracenyl Group, phenanthroline group, fluoranthenyl group, tetrasenyl group, benzimidazolyl group substituted with methyl group, benzimidazolyl group substituted with ethyl group, benzimidazolyl group substituted with phenyl group, biphenyl group substituted A phenyl group unsubstituted or substituted with a benzimidazolyl group, a benzoxazolyl group, or a benzothiazolyl group; a biphenyl group unsubstituted or substituted with a phenyl group; a naphthyl group; a fluorenyl group substituted with a methyl group; a carbazolyl group substituted with a phenyl group Zolyl group; carbazolyl group substituted with naphthyl group; carbazolyl group substituted with biphenyl group; dibenzofuranyl group; fluorenyl group substituted with phenyl group; triazinyl group substituted with phenyl group; dibenzothiophene group; terphenyl group ; Pyridyl group; quinolyl group; pyrenyl group; triphenylenyl group; phenanthrenyl group (phenanthrenyl); anthracenyl group unsubstituted or substituted with a phenyl group or biphenyl group; benzoquinolinyl group; phenanthroline group; fluorantetrenyl group It is selected from the group consisting of a yl group; a tetracenyl group; a benzimidazolyl group unsubstituted or substituted with a methyl group, an ethyl group, a phenyl group or a biphenyl group; a benzoxazolyl group; and a benzothiazolyl group.

According to an exemplary embodiment of the present specification, at least two of R ₁ to R ₈ are connected to each other to form an aromatic ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, two of R ₁ to R ₈ are connected to each other to form an aromatic ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, two of R ₁ to R ₈ are connected to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, three of R ₁ to R ₈ are connected to each other to form a phenalene ring.

According to another exemplary embodiment of the present specification, in Formula 1, R _a and R _b are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 3 to 30 carbon atoms with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group Ring cycloalkyl group; Straight-chain or branched having 1 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Chain alkyl group; Arylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group Ring aryl group; And deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 2 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group It is selected from the group consisting of polycyclic heteroaryl groups.

According to another exemplary embodiment of the present specification, R _a and R _b are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; A straight or branched alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; An arylamine group having 3 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; And it is selected from the group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group.

According to another exemplary embodiment of the present specification, R _a and R _b 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 naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted quinazolinyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted pyrimidyl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted isoquinolinyl group; A substituted or unsubstituted phenanthroline group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzoquinolinyl group; A substituted or unsubstituted spirobifluorenyl group; And it is selected from the group consisting of a substituted or unsubstituted quarterphenyl group.

According to another exemplary embodiment of the present specification, R _a and R _b are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a halogen, nitrile group, alkyl group, aryl group, or heteroaryl group; A biphenyl group unsubstituted or substituted with an aryl group or a heteroaryl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; A quinazolinyl group unsubstituted or substituted with an aryl group; Terphenyl group; A pyrimidyl group unsubstituted or substituted with an aryl group; Thiophene group; Phenanthrenyl group; A pyridyl group unsubstituted or substituted with an aryl group; Quinolinyl group; Isoquinolinyl group; Phenanthroline group; Dibenzofuran group; Dibenzothiophene group; Benzoquinolinyl group; Spirobifluorenyl group; And it is selected from the group consisting of a quarterphenyl group.

According to another exemplary embodiment of the present specification, R _a and R _b are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Phenyl group unsubstituted or substituted with fluorine, nitrile, methyl, t-butyl, phenyl or pyridyl group; A biphenyl group unsubstituted or substituted with a phenyl group or a pyridyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; A quinazolinyl group unsubstituted or substituted with a phenyl group or a naphthyl group; Terphenyl group; A pyrimidyl group unsubstituted or substituted with a phenyl group; Thiophene group; Phenanthrenyl group; A pyridyl group unsubstituted or substituted with a phenyl group; Quinolinyl group; Isoquinolinyl group; Phenanthroline group; Dibenzofuran group; Dibenzothiophene group; Benzoquinolinyl group; Spirobifluorenyl group; And it is selected from the group consisting of a quarterphenyl group.

According to another exemplary embodiment of the present specification, R ₁ to R ₈ are the same as or different from each other, and at least one of R ₁ to R ₈ is a substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 30 carbon atoms. Group, and the heteroaryl group includes at least one selected from N, O, and S as a heteroatom.

According to another exemplary embodiment of the present specification, R _a and R _b are the same as or different from each other, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and the heteroaryl group is a heteroatom It includes at least any one selected from N, O, and S.

이며, 상기 Cy₁ 및 Cy₂는 서로 같거나 상이하고, 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리이며, 상기

은 다른 치환기 또는 결합부에 결합되는 부위이다.According to another exemplary embodiment of the present specification, the R ₁ to R ₈ are the same as or different from each other, and at least one of the R ₁ to R ₈ is

And, the Cy ₁ and Cy ₂ are the same as or different from each other, and a substituted or unsubstituted monocyclic or polycyclic aromatic ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, wherein

Is a moiety bonded to another substituent or bonding portion.

이며, 상기 Cy₁ 및 Cy₂는 서로 같거나 상이하고, 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 고리; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리이며 상기

은 다른 치환기 또는 결합부에 결합되는 부위이다.The R _a and R _b are the same as or different from each other, and each independently

And, the Cy ₁ and Cy ₂ are the same as or different from each other, and a substituted or unsubstituted monocyclic or polycyclic aromatic ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, and the

Is a moiety bonded to another substituent or bonding moiety.

According to another exemplary embodiment of the present specification,

는 하기 하기 구조식들 중 어느 하나로 표시되나, 이에 한정되는 것은 아니다.remind

Is represented by any one of the following structural formulas, but is not limited thereto.

,

,

,

,

,

,

,

,

,

,

,

,

는 추가로 치환될 수 있으며, 중수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기 및 치환 또는 비치환된 헤테로고리기로 이루어진 군으로부터 선택되는 1 또는 2 종 이상의 치환기로 치환될 수 있다.According to another exemplary embodiment of the present specification, the

May be further substituted, and may be substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, in Formula 1, R _a is -L ₅ -Ar ₃ ; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluoranthenyl group; Or a substituted or unsubstituted triphenylenyl group,

L ₅ is a direct bond; Or a substituted or unsubstituted phenylene group,

Ar ₃ is a substituted or unsubstituted pyrimidyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted benzoxazolyl group; A substituted or unsubstituted benzothiazolyl group; A substituted or unsubstituted benzimidazolyl group; A substituted or unsubstituted pyridazinyl group; Or a substituted or unsubstituted quinolyl group.

According to an exemplary embodiment of the present specification, in Formula 1, R _a is -L ₅ -Ar ₃ ; Terphenyl group; Fluoranthenyl group; Or a triphenylenyl group,

L ₅ is a direct bond; Or a phenylene group,

Ar ₃ is a pyrimidyl group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Benzoxazolyl group; Benzothiazolyl group; A benzimidazolyl group unsubstituted or substituted with a methyl group; A pyridazinyl group unsubstituted or substituted with a phenyl group; Or a quinolyl group.

According to another exemplary embodiment of the present specification, in Formula 1, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted A linear or branched alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of an aryl group and a substituted or unsubstituted heterocyclic group; substituted or unsubstituted alkyl group, substituted or A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of an unsubstituted aryl group and a substituted or unsubstituted heterocyclic group; And a substituted or unsubstituted alkyl group , Selected from the group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group do.

According to another exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; 1 or 2 species selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group A linear or branched alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with the above substituents; 6 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of an alkyl group, an aryl group and a heterocyclic group Monocyclic or polycyclic aryl group; And selected from the group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of an alkyl group, an aryl group, and a heterocyclic group. .

According to another exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted Substituted terphenyl group; substituted or unsubstituted naphthyl group; substituted or unsubstituted fluorenyl group; substituted or unsubstituted pyridyl group; substituted or unsubstituted triphenylenyl group; substituted or unsubstituted fluoranthenyl group; substituted Or an unsubstituted quinolinyl group; a substituted or unsubstituted phenanthrenyl group; and a substituted or unsubstituted dibenzofuran group.

According to another exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; a phenyl group unsubstituted or substituted with a halogen, nitrile group, alkyl group, aryl group, or heteroaryl group ; Biphenyl group unsubstituted or substituted with halogen, alkyl group or aryl group; terphenyl group; naphthyl group; fluorenyl group substituted with alkyl or aryl group; pyridyl group; triphenylenyl group; fluoranthenyl group; quinolinyl group; phenanthreenyl group It is selected from the group consisting of a nil group and a dibenzofuran group.

According to another exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; fluorine, nitrile group, methyl group, t-butyl group, phenyl group, naphnyl group, phenanthri A phenyl group unsubstituted or substituted with a nel group, a pyridyl group, a dibenzofuran group, or a biphenyl group; a biphenyl group unsubstituted or substituted with a fluorine, methyl group or a phenyl group; a terphenyl group; a naphthyl group; a fluorenyl group substituted with a methyl group or a phenyl group; It is selected from the group consisting of a pyridyl group; a triphenylenyl group; a fluoranthenyl group; a quinolinyl group; a phenanthrenyl group; and a dibenzofuran group.

According to another exemplary embodiment of the present specification, R'and R" are bonded to form a substituted or unsubstituted heterocycle.

According to another exemplary embodiment of the present specification, R'and R" are bonded to each other to form a substituted or unsubstituted phenothiazine ring; a substituted or unsubstituted acridine ring; a substituted or unsubstituted phenoxazine ring; or It forms a substituted or unsubstituted carbazole ring.

According to another exemplary embodiment of the present specification, the R'and R" are bonded to each other and a phenothiazine ring unsubstituted or substituted with an aryl group; an acridine ring unsubstituted or substituted with an alkyl group or an aryl group; substituted with an aryl group or An unsubstituted phenoxazine ring; Or a carbazole ring unsubstituted or substituted with an alkyl group is formed.

According to another exemplary embodiment of the present specification, R'and R" are bonded to each other to form a phenothiazine ring unsubstituted or substituted with a phenyl group; an acridine ring unsubstituted or substituted with a methyl group or a phenyl group; or substituted with a phenyl group An unsubstituted phenoxazine ring; Or a carbazole ring unsubstituted or substituted with a methyl group is formed.

According to another exemplary embodiment of the present specification, in Formula 1, wherein L ₁ is a direct bond; Straight-chain or branched having 1 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Chain alkylene group; Deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group Ring arylene group; And Heteroaryl having 2 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. It is selected from the group consisting of ren groups.

According to another exemplary embodiment of the present specification, L ₁ is a direct bond; A straight or branched alkylene group having 1 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; And a heteroarylene group having 2 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group.

According to another exemplary embodiment of the present specification, L ₁ is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted triazinylene group; A substituted or unsubstituted naphnylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted divalent dibenzofuran group; A substituted or unsubstituted divalent dibenzothiophene group; A substituted or unsubstituted pyridazinylene group; A substituted or unsubstituted divalent benzofuran group; A substituted or unsubstituted divalent benzothiophene group; A substituted or unsubstituted pyrenylene group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted quinolinylene group; A substituted or unsubstituted divalent triphenylene group; A substituted or unsubstituted furanylene group; A substituted or unsubstituted pyridylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted divalent thiophene group; A substituted or unsubstituted divalent phenanthroline group; A substituted or unsubstituted fluoranthenylene group; A substituted or unsubstituted phenylene group-naphthylene group; A substituted or unsubstituted anthracenylene group-phenylene group; Or a substituted or unsubstituted indolylene group.

According to another exemplary embodiment of the present specification, L ₁ is a direct bond; A phenylene group unsubstituted or substituted with a halogen, nitrile group, alkyl group, or aryl group; A triazinylene group unsubstituted or substituted with an aryl group; Naphnylene group; Biphenylylene group; A fluorenylene group unsubstituted or substituted with an alkyl group or an aryl group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Pyridazinylene group; Divalent benzofuran group; Divalent benzothiophene group; Pyrenylene group; Pyrimidine group; Quinolinylene group; Divalent triphenylene group; Furanylene group; Pyridylene group; An anthracenylene group unsubstituted or substituted with an aryl group; Divalent thiophene group; A divalent phenanthroline group; Fluoranthenylene group; Phenylene group-naphthylene group; Anthracenylene group-phenylene group; Or an indolylene group unsubstituted or substituted with an alkyl group.

According to another exemplary embodiment of the present specification, L ₁ is a direct bond; A phenylene group unsubstituted or substituted with fluorine, nitrile, methyl or phenyl; A triazinylene group unsubstituted or substituted with a phenyl group; Naphnylene group; Biphenylylene group; A fluorenylene group unsubstituted or substituted with a methyl group or a phenyl group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Pyridazinylene group; Divalent benzofuran group; Divalent benzothiophene group; Pyrenylene group; Pyrimidine group; Quinolinylene group; Divalent triphenylene group; Furanylene group; Pyridylene group; Anthracenylene group unsubstituted or substituted with a phenyl group; Divalent thiophene group; A divalent phenanthroline group; Fluoranthenylene group; Phenylene group-naphthylene group; Anthracenylene group-phenylene group; Or it is an indolylene group substituted or unsubstituted with a methyl group.

In the present specification, the phenylene group-naphthylene group refers to a divalent linking group and may be represented by the following structure, but is not limited thereto.

In the present specification, the anthracenylene group-phenylene group means a divalent linking group, and may be represented by the following structure, but is not limited thereto.

According to another exemplary embodiment of the present specification, in Formula 2, the groups not connected to Formula 1 either directly or through a linking group (L ₂ ) of R ₉ to R ₁₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; Deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 3 to 30 carbon atoms with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group Ring cycloalkyl group; An alkoxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An aryloxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An alkylthioxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An arylthioxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An alkyl sulfoxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Arylsulfoxy group substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An alkenyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; A silyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; A boron group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An alkylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An aralkylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Arylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; A heteroarylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; An arylphosphine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; A phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Straight-chain or branched having 1 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Chain alkyl group; Deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group Ring aryl group; And deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 2 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group It is selected from the group consisting of polycyclic heteroaryl groups.

According to another exemplary embodiment of the present specification, the groups not connected to Formula 1 either directly or through a linking group (L ₂ ) of R ₉ to R ₁₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; An alkoxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; An aryloxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; An alkylthioxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; An arylthioxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; An alkyl sulfoxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; Arylsulfoxy group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; An alkenyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A silyl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; A boron group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; An alkylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; An aralkylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; An arylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A heteroarylamine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; An arylphosphine group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; A phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A straight or branched alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; And it is selected from the group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group.

According to another exemplary embodiment of the present specification, the groups not connected to Formula 1 either directly or through a linking group (L ₂ ) of R ₉ to R ₁₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted triazinyl group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted benzoquinolinyl group; A substituted or unsubstituted phenanthroline group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted tetracenyl group; A substituted or unsubstituted benzimidazolyl group; A substituted or unsubstituted benzoxazolyl group; And it is selected from the group consisting of a substituted or unsubstituted benzothiazolyl group.

According to another exemplary embodiment of the present specification, the groups not connected to Formula 1 either directly or through a linking group (L ₂ ) of R ₉ to R ₁₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile; A phenyl group unsubstituted or substituted with a halogen, nitrile group, an aryl group unsubstituted or substituted with an aryl group, or a heteroaryl group unsubstituted or substituted with an alkyl group or an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; Naphthyl group; A fluorenyl group substituted with an alkyl group; A carbazolyl group substituted with an aryl group; Dibenzofuranyl group; A fluorenyl group substituted with an aryl group; a triazinyl group substituted with an aryl group; Dibenzothiophene group; Terphenyl group; Pyridyl group; Quinolyl group; Pyrenyl group; Triphenylenyl group; Phenanthrenyl group; An anthracenyl group unsubstituted or substituted with an aryl group; Benzoquinolinyl group; Phenanthroline group; Fluoranthenyl group; Tetracenyl group; A benzimidazolyl group unsubstituted or substituted with an alkyl group or an aryl group; Benzoxazolyl group; And it is selected from the group consisting of a benzothiazolyl group.

According to another exemplary embodiment of the present specification, the groups not connected to Formula 1 either directly or through a linking group (L ₂ ) of R ₉ to R ₁₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile; Fluorine, nitrile group, phenyl group, pyridyl group, naphthyl group, quinolinyl group, pyrenyl group, triphenylenyl group, phenanthrenyl group, anthracenyl group substituted with biphenyl group, anthracenyl group substituted with phenyl group, anthracenyl group , Phenanthroline group, fluoranthenyl group, tetracenyl group, benzimidazolyl group substituted with methyl group, benzimidazolyl group substituted with ethyl group, benzimidazolyl group substituted with phenyl group, biphenyl group A phenyl group unsubstituted or substituted with a benzimidazolyl group, a benzoxazolyl group, or a benzothiazolyl group; A biphenyl group unsubstituted or substituted with a phenyl group; Naphthyl group; A fluorenyl group substituted with a methyl group; A carbazolyl group substituted with a phenyl group; A carbazolyl group substituted with a naphthyl group; A carbazolyl group substituted with a biphenyl group; Dibenzofuranyl group; A fluorenyl group substituted with a phenyl group; A triazinyl group substituted with a phenyl group; Dibenzothiophene group; Terphenyl group; Pyridyl group; Quinolyl group; Pyrenyl group; Triphenylenyl group; Phenanthrenyl group; An anthracenyl group unsubstituted or substituted with a phenyl group or a biphenyl group; Benzoquinolinyl group; Phenanthroline group; Fluoranthenyl group; Tetracenyl group; A benzimidazolyl group unsubstituted or substituted with a methyl group, an ethyl group, a phenyl group or a biphenyl group; Benzoxazolyl group; And it is selected from the group consisting of a benzothiazolyl group.

According to an exemplary embodiment of the present specification, at least two of R ₉ to R ₁₆ are connected to each other to form an aromatic ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, two of R ₉ to R ₁₆ are connected to each other to form an aromatic ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, two of R ₉ to R ₁₆ are connected to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, three of R ₉ to R ₁₆ are connected to each other to form a phenalene ring.

According to another exemplary embodiment of the present specification, in Chemical Formula 2, R _c is hydrogen; heavy hydrogen; Deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 3 to 30 carbon atoms with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group Ring cycloalkyl group; Straight-chain or branched having 1 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Chain alkyl group; Arylamine group having 3 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group ; Deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group Ring aryl group; And deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 2 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group It is selected from the group consisting of polycyclic heteroaryl groups.

According to another exemplary embodiment of the present specification, R _c is hydrogen; heavy hydrogen; A monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; A straight or branched alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; An arylamine group having 3 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; And it is selected from the group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group.

According to another exemplary embodiment of the present specification, R _c is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted quinazolinyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted pyrimidyl group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted quinolinyl group; A substituted or unsubstituted isoquinolinyl group; A substituted or unsubstituted phenanthroline group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzoquinolinyl group; A substituted or unsubstituted spirobifluorenyl group; And it is selected from the group consisting of a substituted or unsubstituted quarterphenyl group.

According to another exemplary embodiment of the present specification, R _c is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a halogen, nitrile group, alkyl group, aryl group, or heteroaryl group; A biphenyl group unsubstituted or substituted with an aryl group or a heteroaryl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; A quinazolinyl group unsubstituted or substituted with an aryl group; Terphenyl group; A pyrimidyl group unsubstituted or substituted with an aryl group; Thiophene group; Phenanthrenyl group; A pyridyl group unsubstituted or substituted with an aryl group; Quinolinyl group; Isoquinolinyl group; Phenanthroline group; Dibenzofuran group; Dibenzothiophene group; Benzoquinolinyl group; Spirobifluorenyl group; And it is selected from the group consisting of a quarterphenyl group.

According to another exemplary embodiment of the present specification, R _c is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Phenyl group unsubstituted or substituted with fluorine, nitrile, methyl, t-butyl, phenyl or pyridyl group; A biphenyl group unsubstituted or substituted with a phenyl group or a pyridyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; A quinazolinyl group unsubstituted or substituted with a phenyl group or a naphthyl group; Terphenyl group; A pyrimidyl group unsubstituted or substituted with a phenyl group; Thiophene group; Phenanthrenyl group; A pyridyl group unsubstituted or substituted with a phenyl group; Quinolinyl group; Isoquinolinyl group; Phenanthroline group; Dibenzofuran group; Dibenzothiophene group; Benzoquinolinyl group; Spirobifluorenyl group; And it is selected from the group consisting of a quarterphenyl group.

According to another exemplary embodiment of the present specification, in Chemical Formula 2, L ₂ is a direct bond; Straight-chain or branched having 1 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Chain alkylene group; Deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group Ring arylene group; And Heteroaryl having 2 to 30 carbon atoms substituted or unsubstituted with one or two or more substituents selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. It is selected from the group consisting of ren groups.

According to another exemplary embodiment of the present specification, L ₂ is a direct bond; A straight or branched alkylene group having 1 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group and a heterocyclic group; And a heteroarylene group having 2 to 30 carbon atoms unsubstituted or substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group.

According to another exemplary embodiment of the present specification, L ₂ is a direct bond; Or a substituted or unsubstituted phenylene group.

According to another exemplary embodiment of the present specification, L ₂ is a direct bond; Or a phenylene group.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 3 to 6.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 3 to 6,

X and X ₁ to X ₃ are the same as or different from each other, and each independently O, S, NR _a or P(=O)R _b ,

R ₂₀ to R ₃₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

R _a and R _b are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

L ₁ is a direct bond; A substituted or unsubstituted C 1 to C 30 linear or branched alkylene group; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; And a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,

L ₂ , L ₃ and L ₄ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C 1 to C 30 linear or branched alkylene group; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; And a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,

R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic group having 6 to 30 carbon atoms An aryl group; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

R'" is hydrogen; deuterium; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and substituted or unsubstituted carbon number 2 It is selected from the group consisting of monocyclic or polycyclic heteroaryl groups of to 30,

e, f, i, j, k, m, q and s are the same as or different from each other, and each independently an integer of 1 to 3,

d, g, h, n, p and r are the same as or different from each other, and each independently, is an integer of 1 to 4,

When d, e, f, g, h, i, j, k, m, n, p, q, r or s are 2 or more, the substituents in the parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 3 is represented by Chemical Formula 3-1 below.

[Formula 3-1]

In Formula 3-1,

The definitions of X ₂ , R ₂₀ to R ₂₃ , d, e, f, g and L ₂ are the same as in Formula 3,

Ra is -L ₅ -Ar ₃ ; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluoranthene group; Or a substituted or unsubstituted triphenylenyl group,

L ₅ is a direct bond; Or a substituted or unsubstituted phenylene group,

Ar ₃ is a substituted or unsubstituted pyrimidyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted benzoxazolyl group; A substituted or unsubstituted benzothiazolyl group; A substituted or unsubstituted benzimidazolyl group; A substituted or unsubstituted pyridazinyl group; Or a substituted or unsubstituted quinolyl group.

According to another exemplary embodiment of the present specification, Formula 3 is represented by any one of the following Formulas 3-2 to 3-12.

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

[Chemical Formula 3-9]

[Chemical Formula 3-10]

[Chemical Formula 3-11]

[Formula 3-12]

In Formulas 3-2 to 3-12,

The definitions of X ₂ , R ₂₀ to R ₂₃ , d, e, f, g and L ₁ are the same as in Formula 3,

The definition of L ₅ is the same as in Chemical Formula 3-1,

G ₁ to G ₁₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

g1, g2, g7 and g11 are each an integer of 1 to 4,

g3 is an integer from 1 to 5,

g4 and g13 are each an integer of 1 to 3,

g5 and g14 are each an integer of 1 to 6,

g6 and g10 are each an integer of 1 to 7,

When g1, g2, g3, g4, g5, g6, g7, g10, g11, g13, and g14 are each 2 or more, the structures in the two or more parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, in Formula 3, L ₂ is a direct bond.

According to an exemplary embodiment of the present specification, in Formulas 3-1 to 3-12, G ₁ to G ₁₄ are the same as or different from each other, and each independently hydrogen; Alkyl group; Or an aryl group.

According to an exemplary embodiment of the present specification, in Formulas 3-1 to 3-12, G ₁ to G ₁₄ are the same as or different from each other, and each independently hydrogen; Methyl group; Or a phenyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 4 is represented by any one of Chemical Formulas 4-1 to 4-7 below.

[Formula 4-1]

[Formula 4-2]

[Chemical Formula 4-3]

[Formula 4-4]

[Formula 4-5]

[Formula 4-6]

[Formula 4-7]

[Formula 4-8]

[Formula 4-9]

[Formula 4-10]

[Formula 4-11]

[Formula 4-12]

[Formula 4-13]

[Formula 4-14]

[Formula 4-15]

[Formula 4-16]

In Formulas 4-1 to 4-16,

R ₂₄ to R ₂₉ , R _a , L ₃ , L ₄ , h, i, j, k, m and n are the same as in Formula 4,

R _a1 and R _a2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 4, L ₃ and L ₄ are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; Quinolinylene group; Or a pyridylene group.

According to an exemplary embodiment of the present specification, Chemical Formula 5 is represented by any one of Chemical Formulas 5-1 to 5-4 below.

[Chemical Formula 5-1]

[Formula 5-2]

[Chemical Formula 5-3]

[Chemical Formula 5-4]

In Formulas 5-1 to 5-5,

R ₃₀ , R ₃₁ , L ₁ , R', R", p, q and R _b are the same as in Formula 5,

R _a is a substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluoranthene group; Or a substituted or unsubstituted triphenylenyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 6 is represented by Chemical Formula 6-1 below.

[Formula 6-1]

In Formula 6-1,

R ₃₂ , R ₃₃ , R _a , r, s and L ₁ are the same as in Chemical Formula 6,

R"' is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group.

According to an exemplary embodiment of the present specification, in Formula 6-1, R"' is a substituted or unsubstituted aryl group; a substituted or unsubstituted monocyclic or bicyclic heteroaryl group; or a substituted or unsubstituted 6 membered It is a heteroaryl group of 3 or more rings.

According to another exemplary embodiment of the present specification, in Formula 6-1, R"' is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; substituted or unsubstituted Fluorenyl group; substituted or unsubstituted carbazolyl group; substituted or unsubstituted dibenzofuranyl group; substituted or unsubstituted triazinyl group; substituted or unsubstituted dibenzothiophene group; substituted or unsubstituted tertiary Phenyl group; substituted or unsubstituted pyridyl group; substituted or unsubstituted quinolyl group; substituted or unsubstituted pyrenyl group; substituted or unsubstituted triphenylenyl group; substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted anthracenyl group; substituted or unsubstituted benzoquinolinyl group; substituted or unsubstituted phenanthroline group; substituted or unsubstituted fluoranthenyl group; substituted or unsubstituted tetrasenyl group; substituted or unsubstituted benzoquinolinyl group It is selected from the group consisting of a substituted benzimidazolyl group; a substituted or unsubstituted benzoxazolyl group; and a substituted or unsubstituted benzothiazolyl group.

According to another exemplary embodiment of the present specification, in Formula 6-1, R"' is a halogen, a nitrile group, an aryl group unsubstituted or substituted with an aryl group, or a heteroaryl unsubstituted or substituted with an alkyl group or an aryl group. A phenyl group substituted or unsubstituted with a group; a biphenyl group substituted or unsubstituted with an aryl group; a naphthyl group; a fluorenyl group substituted with an alkyl group; a carbazolyl group substituted with an aryl group; a dibenzofuranyl group; a fluorenyl group substituted with an aryl group; Triazinyl group substituted with an aryl group; dibenzothiophene group; terphenyl group; pyridyl group; quinolyl group; pyrenyl group; triphenylenyl group; phenanthrenyl group; anthracenyl group unsubstituted or substituted with an aryl group ; Benzoquinolinyl group; phenanthroline group; fluoranthenyl group; tetrasenyl group; benzimidazolyl group unsubstituted or substituted with an alkyl or aryl group; benzoxazolyl group; and a benzothiazolyl group.

According to another exemplary embodiment of the present specification, in Formula 6-1, R"' is fluorine, nitrile group, phenyl group, pyridyl group, naphthyl group, quinolinyl group, pyrenyl group, triphenylenyl group, phenane Trenyl group, anthracenyl group substituted with biphenyl group, anthracenyl group substituted with phenyl group, anthracenyl group, phenanthroline group, fluoranthenyl group, tetrasenyl group, benzimidazolyl group substituted with methyl group, ethyl group A substituted benzimidazolyl group, a benzimidazolyl group substituted with a phenyl group, a benzimidazolyl group substituted with a biphenyl group, a benzoxazolyl group, or a phenyl group unsubstituted or substituted with a benzothiazolyl group; substituted with a phenyl group or Unsubstituted biphenyl group; naphthyl group; fluorenyl group substituted with methyl group; carbazolyl group substituted with phenyl group; carbazolyl group substituted with naphthyl group; carbazolyl group substituted with biphenyl group; dibenzofuranyl group; phenyl group Substituted fluorenyl group; triazinyl group substituted with phenyl group; dibenzothiophene group; terphenyl group; pyridyl group; quinolyl group; pyrenyl group; triphenylenyl group; phenanthrenyl group; phenyl group or biphenyl group Anthracenyl group unsubstituted or substituted with; benzoquinolinyl group; phenanthroline group; fluoranthenyl group; tetrasenyl group; benzimidazolyl group unsubstituted or substituted with methyl, ethyl, phenyl or biphenyl group; benzoxaxa It is selected from the group consisting of a zolyl group and a benzothiazolyl group.

According to an exemplary embodiment of the present specification, the compound of Formula 1 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following compounds.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following compounds.

Since the light efficiency improving layer including the compound represented by Formula 1 has a high refractive index, it may contribute to improving the light efficiency of the organic light emitting device, in particular, the external efficiency. For example, the light efficiency improvement layer may have a refractive index of 1.8 or more, preferably 1.9, at a wavelength of 630 nm.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except for including a light efficiency improvement layer.

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, by using a physical vapor deposition (PVD) method 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 manufactured by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In this case, the light efficiency improvement layer according to the present invention may be formed under the anode or on the cathode. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing an anode material, an organic material layer, and a cathode material on a substrate.

The organic material layer of the organic light emitting device of the present specification may have a multilayer structure in which one or more organic material layers are stacked.

In the exemplary embodiment of the present specification, the organic light-emitting device further includes one layer or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. can do.

For example, the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.

1 and 2 illustrate an example in which a light efficiency improvement layer is formed on an upper portion of a cathode and a lower portion of the anode, respectively, as shown in FIG. 3, a light efficiency improvement layer may be formed not only on the upper portion of the cathode but also on the lower portion of the anode.

The organic light-emitting device 10 of FIG. 1 includes an anode 30, an organic layer 40, a cathode 50, and a light efficiency improvement layer 60 on a substrate 20 in order. 1 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

The cathode 50 of FIG. 1 is a transmissive electrode, and light generated in the organic layer 40 may pass through the cathode 50, pass through the light efficiency improvement layer 60, and be extracted to the outside of the organic light-emitting device 10. .

The organic light emitting device 11 of FIG. 2 includes a light efficiency improvement layer 60, an anode 30, an organic layer 40, and a cathode 50 on a substrate 20 in order. 2 is an exemplary structure according to the exemplary embodiment of the present specification, and may further include another organic material layer.

The anode 30 of FIG. 2 is a transmissive electrode, and light generated from the organic layer 40 may pass through the anode 30 and be extracted into the air through the light efficiency improvement layer 60. Since the light efficiency improvement layer 60 including the compound represented by Formula 1 above has a high refractive index, light generated from the organic layer 40 can be effectively extracted into the air according to the principle of constructive interference, and thus improved light efficiency characteristics Can have

The organic light-emitting device 12 of FIG. 3 has a first light-efficiency improvement layer 61, an anode 30, an organic layer 40, a cathode 50, and a second light-efficiency improvement layer 62 on a substrate 20 in order. do. Among the organic light emitting diodes 12, the anode 30 and the cathode 50 are transmissive electrodes, and the light generated from the organic layer 40 passes through the anode 30 and the cathode 50 and passes through the first light efficiency improvement layer 61, respectively. ) And the second light efficiency improvement layer 62 may be taken out into the air. Since the first light efficiency improvement layer 61 and the second light efficiency improvement layer 62 including the compound represented by Chemical Formula 1 have a high refractive index, the light generated from the organic layer 40 is effectively reduced according to the principle of constructive interference. Since it can be blown out into the air, it can have improved light efficiency characteristics.

Of course, the light efficiency improvement layer may not be formed only at these locations.

For example, an additional layer may be provided between the light efficiency improving layer and the anode or cathode as necessary, and the number of organic layers between the anode and the cathode may be stacked less or more as necessary.

The organic material layer and the light efficiency improvement layer are made of various polymer materials and are used in a solution process or a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. Thus, it can be manufactured with fewer layers.

As the substrate 20, a material known in the art may be used. For example, a glass substrate, silicon wafer, or transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and water resistance may be used. I can.

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.

As the material of the anode 30, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer 40. Specific examples of the anode 30 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); A combination of a metal and an oxide 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.

The cathode 50 material is generally preferably a material having a small work function to facilitate electron injection into the organic material layer 40. Specific examples of the material of the cathode 50 include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; A transmissive electrode can be obtained by forming a LiF/Al or LiO ₂ /Al thin film. Meanwhile, in order to obtain a top light emitting device, various modifications are possible, such as being able to form a transmissive electrode using indium tin oxide (ITO) or indium zinc oxide (IZO).

The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, 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 is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. 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 highest occupied molecular orbital (HOMO) of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and 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 receives holes from the hole injection layer and transports holes to the emission layer.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material of the light-emitting layer, a material capable of emitting light in the visible region by transporting 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-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The dopant material may be an organic compound, a metal or a metal compound.

Organic compounds as dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, and fluoranthene compounds. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted A compound in which at least one arylvinyl group is substituted on the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, a general metal or metal compound may be used as the metal or metal compound, and specifically, a metal complex may be used. Examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, and injects holes of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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 electron transport layer material has a function of stably transporting electrons injected from the electron injection electrode (cathode), and a known electron transport material may be used. Examples thereof include quinoline derivatives, in particular tris(8-quinolinolate)aluminum (Alq ₃ ); TAZ; Balq and the like, but are not limited thereto.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP:2,9-Dimethyl-4,7-diphenyl -1,10-phenanthroline), aluminum complex, and the like, but are not limited thereto.

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.

In addition, the organic light emitting device according to the present specification may have a normal type in which a lower electrode is an anode and an upper electrode is a cathode, and may have an inverted type in which the lower electrode is a cathode and the upper electrode is an anode.

According to the exemplary embodiment of the present specification, the anode is a transmissive electrode, and the light efficiency improvement layer may be provided on a surface opposite to a surface of the anode facing the organic layer.

According to another exemplary embodiment of the present specification, the cathode is a transmissive electrode, and the light efficiency improvement layer may be provided on a surface of the cathode opposite to a surface facing the organic layer.

According to another exemplary embodiment of the present specification, the anode and the cathode are transmissive electrodes, and the light efficiency improving layer is a surface opposite to a surface of the anode facing the organic layer and a surface opposite to a surface of the cathode facing the organic layer. May be provided in each of the.

The transmissive electrode may have a visible light transmittance of 60% or more. Specifically, the electrode may have a visible light transmittance of 80% or more.

The transmissive electrode may be formed of a transparent material such as a transparent conductive oxide, or a thin film of an opaque material such as a metal.

According to an exemplary embodiment of the present invention, the organic layer of the organic light emitting device may be patterned for each of R, G, and B pixels.

Accordingly, the organic layer may include a red light-emitting organic layer, a green light-emitting organic layer, and a blue light-emitting organic layer.

In this case, the light efficiency improvement layer including the compound represented by Chemical Formula 1 may be formed as a common layer for R, G, and B pixels. The common layer means provided in all of the R, G, and B pixels. When the light efficiency improvement layer is formed as a common layer for R, G, and B pixels, the thickness may be 500 Å to 800 Å. When the above range is satisfied, an excellent light efficiency improvement effect can be achieved.

According to another exemplary embodiment of the present specification, the light efficiency improvement layer is an R-light efficiency improvement layer formed in a region corresponding to the R pixel, for the R, G, and B pixels, and is formed in a region corresponding to the G pixel. It may include at least one of a G-light efficiency improvement layer and a B-light efficiency improvement layer formed in a region corresponding to the B pixel. That is, the image efficiency improvement layer may be patterned for each of R, G, and B pixels.

According to another exemplary embodiment of the present specification, the thicknesses of the R-light efficiency improvement layer, the G-light efficiency improvement layer, and the B-light efficiency improvement layer may be the same or different from each other.

According to another exemplary embodiment of the present specification, the light efficiency improvement layer may include an R-light efficiency improvement layer, a G-light efficiency improvement layer, and a B-light efficiency improvement layer.

According to another exemplary embodiment of the present specification, the light efficiency improvement layer-R, the light efficiency improvement layer-G, and the light efficiency improvement layer-B of the light efficiency improvement layer are opposite to the surface opposite to the organic layer and the cathode of the anode. It may be provided on each of the opposite surface of the surface facing the organic layer.

Hereinafter, the present invention will be described in more detail based on synthesis examples and examples. These examples are intended to aid understanding of the present invention, and the scope of the present invention is not limited thereto.

Synthesis example

[Scheme 1]

P1 (1.0 eq.), P2 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.02 eq.), K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) was added to Tetrahydrofuran and refluxed. Compound A was obtained. Examples of the compound synthesized by Scheme 1 are as follows.

In Reaction Scheme 1, the definitions of R _a , R ₂₀ , R ₂₃ , d and g are the same as in Chemical Formula 3, and the definition of R _c is the same as in Chemical Formula 2.

<Synthesis Example 1-1> Synthesis of Compound 1-1

Compound 1-1-A (22.1 g, 46.6 mmol), Compound 1-1-B (14.7 g, 51.3 mmol), Potassium carbonate (19.3 g, 139.8 mmol) and Tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added to Tetrahydrofuran and refluxed for 12 hours. After the reaction was completed, the water layer was removed, the organic layer was dried with Magnesium sulfate, and the filtered liquid was distilled under reduced pressure. The obtained solid was dissolved in Chloroform (500 ml), Ethyl acetae (100 ml) was added, recrystallized, and dried to obtain compound 1-1 (25.5 g, yield 86%; MS:[M+H] ⁺ =637).

<Synthesis Example 1-2> Synthesis of Compound 1-2

In Synthesis Example 1-1, compound 1-2-A (22.1 g, 46.6 mmol) instead of compound 1-1-A, and compound 1-2-B (14.7 g, 51.36 mmol) instead of compound 1-1-B were used. Except that, compound 1-2 (24.0 g, yield 81%; MS:[M+H] ⁺ =637) was obtained in the same manner as in Synthesis Example 1-1.

<Synthesis Example 1-3> Synthesis of Compound 1-3

Compound 1-3 (24.6 g, yield 83) in the same manner as in Synthesis Example 1-1, except that compound 1-2-B (14.7 g, 51.36 mmol) was used instead of compound 1-1-B in Synthesis Example 1-1. %; MS:[M+H] ⁺ =637) was obtained.

<Synthesis Example 1-4> Synthesis of Compound 1-4

Compound 1-4 (22.8 g, yield 77) in the same manner as in Synthesis Example 1-1 except that compound 1-2-A (22.1 g, 46.6 mmol) was used instead of compound 1-1-A in Synthesis Example 1-1. %; MS:[M+H] ⁺ =637) was obtained.

<Synthesis Examples 1-5 to 1-30> Synthesis of compounds 1-5 to 1-30

By changing Ra and Rc in Scheme 1, compounds 1-5 to 1-30 were synthesized in the same manner as in Scheme 1.

[Scheme 2]

P3 (1.0 eq.), P4 (1.1 eq.), and sodium tert-butoxide (1.5 eq.) were added to xylene and refluxed to obtain compound B. Examples of the compound synthesized by Scheme 2 are as follows.

In Reaction Scheme 2, the definitions of R _a , R ₂₀ , R ₂₃ , d and g are the same as in Chemical Formula 3, and the definition of R _c is the same as in Chemical Formula 2.

<Synthesis Example 2-1> Synthesis of Compound 2-1

Compound 2-1-A (10.0 g, 24.5 mmol), 2-Bromonaphtrhalene (5.58 g, 26.9 mmol), and sodium tert-butoxide (3.53 g, 36.7 mmol) were added to Xylene (200 ml) and refluxed. When reflux started, Bis(tri-tert-butylphosphine)palladium(0) (0.13 g, 0.2 mmol) dissolved in 5 ml of Xylene was slowly added dropwise. After refluxing for 1 hour, when the reaction was completed, it was cooled to room temperature and filtered. The liquid obtained by filtration was distilled under reduced pressure, recrystallized using Tetrahydrofuran (100 ml) and Ethyl acetate (300 ml), filtered and dried, and compound 2-1 (4.9 g, yield 37.4%; MS:[M+H] ⁺ =535).

<Synthesis Example 2-2> Synthesis of Compound 2-2

Compound 2-2 (5.8 g, yield) in the same manner as in Synthesis Example 2-1, except that 4-bromo-1,1'-biphenyl (6.27 g, 26.9 mmol) was used instead of 2-Bromonaphtrhalene in Synthesis Example 2-1. 42.0%; MS:[M+H] ⁺ =561) was obtained.

[Scheme 3]

P5-1 (1.0 eq.), P5 (1.05 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.02 eq.), and K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) were added to Tetrahydrofuran. Compound C was obtained by refluxing. Examples of the compound synthesized by Scheme 3 are as follows.

In Scheme 3, the definitions of R _a , R ₃₀ , p, L ₁ , R'and R" are the same as in Formula 5.

<Synthesis Example 3-1> Synthesis of Compound 3-1

Compound 3-1-A (15.0 g, 46.6 mmol), Compound 3-1-B (22.6 g, 51.3 mmol), Potassium carbonate (19.3 g, 139.8 mmol) and Tetrakis(triphenylphosphine)palladium(0) (1.1 g, 0.9 mmol) was added to Tetrahydrofuran and refluxed for 18 hours. After the reaction was completed, the water layer was removed, the organic layer was dried with Magnesium sulfate, and the filtered liquid was distilled under reduced pressure. The obtained solid was dissolved in chloroform (100 ml), Ethyl acetae (100 ml) was added, recrystallized, and dried to obtain compound 3-1 (22.3 g, yield 75%; MS:[M+H] ⁺ =639).

<Synthesis Example 3-2> Synthesis of Compound 3-2

Compound 3-2 (23.5 g, yield 79) in the same manner as in Synthesis Example 3-1, except that compound 3-2-A (15.0 g, 46.6 mmol) was used instead of compound 3-1-A in Synthesis Example 3-1. %; MS:[M+H] ⁺ =639) was obtained.

<Synthesis Examples 3-3 to 3-12> Synthesis of compounds 3-3 to 3-12

By changing R _a , R ₃₀ , p, L ₁ , R'and R" in Scheme 3, compounds 3-3 to 3-12 were synthesized in the same manner as in Scheme 3.

[Scheme 4]

P6 (1.0 eq.), P5 (1.05 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.02 eq.), K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) was added to Tetrahydrofuran and refluxed. Compound D was obtained. Examples of the compound synthesized by Scheme 4 are as follows.

In Scheme 4, the definitions of R ₃₀ , p, L ₁ , R'and R" are the same as in Formula 5.

<Synthesis Example 4-1> Synthesis of Compound 4-1

In Synthesis Example 3-1, compound 4-1-A (11.5 g, 46.6 mmol) instead of compound 3-1-A, and compound 4-1-B (22.6 g, 51.3 mmol) instead of compound 3-1-B Except for that, compound 4-1 (17.6 g, yield 67%; MS:[M+H] ⁺ = 564) was obtained in the same manner as in Synthesis Example 3-1.

<Synthesis Examples 4-2 to 4-21> Synthesis of Compounds 4-2 to 4-21

By changing R ₃₀ , p, L ₁ , R'and R" in Scheme 4, compounds 4-2 to 4-21 were synthesized in the same manner as in Scheme 4.

[Scheme 5]

P7 (1.0 eq.), P5 (1.05 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.02 eq.), K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) was added to Tetrahydrofuran and refluxed. Compound E was obtained. Examples of the compound synthesized by Scheme 5 are as follows.

In Scheme 5, the definitions of R ₃₀ , p, L ₁ , R'and R" are the same as in Formula 5.

<Synthesis Example 5-1> Synthesis of Compound 5-1

In Synthesis Example 3-1, compound 5-1-A (12.3 g, 46.6 mmol) instead of compound 3-1-A, and compound 5-1-B (22.6 g, 51.3 mmol) instead of compound 3-1-B were used. Except for that, compound 5-1 (16.5 g, yield 61%; MS:[M+H] ⁺ =580) was obtained in the same manner as in Synthesis Example 3-1.

<Synthesis Examples 5-2 to 5-21> Synthesis of Compounds 5-2 to 5-21

By changing R ₃₀ , p, L ₁ , R'and R" in Scheme 5, compounds 5-2 to 5-21 were synthesized in the same manner as in Scheme 5.

[Scheme 6]

P8-1 (2.1 eq.), P8 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.03 eq.), and K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) were added to dioxane. Refluxed to obtain compound F. Examples of the compound synthesized by Scheme 6 are as follows.

In Scheme 6, the definitions of R ₂₄ , h and R _a are the same as in Chemical Formula 4, and the definition of R _a1 is the same as in Chemical Formula 4-1.

<Synthesis Example 6-1> Synthesis of Compound 6-1

Compound 6-1-A (20.0 g, 48.8 mmol), Compound 6-1-B (29.4 g, 102.4 mmol), Potassium carbonate (41.4 g, 195.1 mmol) and Tetrakis(triphenylphosphine)palladium(0) (1.69 g, 1.5 mmol) was added to dioxane and refluxed for 4 hours. After the reaction was completed, the resulting solid was filtered, dissolved in chloroform, dried over Magnesium sulfate, and partially distilled under reduced pressure. Ethanol was added to the solution and recrystallized to obtain compound 6-1 (23.0 g, yield 65%; MS:[M+H] ⁺ =726).

<Synthesis Example 6-2> Synthesis of Compound 6-2

Compound 6-2 (25.4 g, yield 67.0) in the same manner as in Synthesis Example 6-1, except that compound 6-2-A (22.0 g, 48.8 mmol) was used instead of compound 6-1-A in Synthesis Example 6-1. %; MS:[M+H] ⁺ =776) was obtained.

<Synthesis Examples 6-3 to 6-8> Synthesis of compounds 6-3 to 6-8

By changing R ₂₄ , h, R _a and R _a1 in Scheme 6, compounds 6-3 to 6-8 were synthesized in the same manner as in Scheme 6.

[Scheme 7]

P8-2 (2.1 eq.), P8 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.03 eq.), and K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) were added to dioxane. Compound G was obtained by refluxing. Examples of the compound synthesized by Scheme 7 are as follows.

The definition of R ₂₄ , h and R _a in Scheme 7 is the same as in Formula 4.

<Synthesis Example 7-1> Synthesis of Compound 7-1

In Synthesis Example 6-1, compound 7-1-A (19.6 g, 48.8 mmol) instead of compound 6-1-A, and compound 7-1-B (21.7 g, 102.4 mmol) instead of compound 6-1-B were used. Except that, compound 7-1 (14.6 g, yield 52%; MS:[M+H] ⁺ =576) was obtained in the same manner as in Synthesis Example 6-1.

[Scheme 8]

P8-3 (2.1 eq.), P8 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.03 eq.), and K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) were added to dioxane. Refluxed to obtain compound H. Examples of the compound synthesized by Scheme 8 are as follows.

In Scheme 8, the definitions of R ₂₄ , h and R _a are the same as in Formula 4.

<Synthesis Example 8-1> Synthesis of Compound 8-1

In Synthesis Example 6-1, compound 7-1-A (19.6 g, 48.8 mmol) instead of compound 6-1-A, and compound 8-1-B (23.3 g, 102.4 mmol) instead of compound 6-1-B Except that, in the same manner as in Synthesis Example 6-1, compound 8-1 (16.3 g, yield 55%; MS:[M+H] ⁺ =608) was obtained.

[Scheme 9]

P8-2 (2.1 eq.), P9 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.03 eq.), and K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) were added to dioxane. Refluxed to obtain compound I. Examples of the compound synthesized by Scheme 9 are as follows.

The definition of R ₂₄ and h in Scheme 9 is the same as in Formula 4.

<Synthesis Example 9-1> Synthesis of Compound 9-1

In Synthesis Example 6-1, compound 9-1-A (15.9 g, 48.8 mmol) instead of compound 6-1-A, and compound 7-1-B (21.7 g, 102.4 mmol) instead of compound 6-1-B Except that, in the same manner as in Synthesis Example 6-1, compound 9-1 (14.2 g, yield 58%; MS:[M+H] ⁺ =501) was obtained.

[Scheme 10]

P8-3 (2.1 eq.), P10 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.03 eq.), and K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) were added to dioxane. It was refluxed to obtain compound J. Examples of the compound synthesized by Scheme 10 are as follows.

The definition of R ₂₄ and h in Scheme 10 is the same as in Formula 4.

<Synthesis Example 10-1> Synthesis of Compound 10-1

In Synthesis Example 6-1, compound 10-1-A (16.7 g, 48.8 mmol) instead of compound 6-1-A, and compound 8-1-B (23.3 g, 102.4 mmol) instead of compound 6-1-B were used. Except for that, compound 10-1 (13.2 g, yield 49%; MS:[M+H] ⁺ =549) was obtained in the same manner as in Synthesis Example 6-1.

[Scheme 11]

P8-2 (2.1 eq.), P10 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.03 eq.), and K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) were added to dioxane. It was refluxed to obtain compound K. Examples of the compound synthesized by Scheme 11 are as follows.

The definition of R ₂₄ and h in Scheme 11 is the same as in Formula 4.

<Synthesis Example 11-1> Synthesis of Compound 11-1

In Synthesis Example 6-1, compound 10-1-A (16.7 g, 48.8 mmol) instead of compound 6-1-A, and compound 7-1-B (21.7 g, 102.4 mmol) instead of compound 6-1-B were used. Except for that, compound 11-1 (13.4 g, yield 53%; MS:[M+H] ⁺ =517) was obtained in the same manner as in Synthesis Example 6-1.

[Scheme 12]

P8-3 (2.1 eq.), P9 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.03 eq.), and K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) were added to dioxane. It was refluxed to obtain compound L. Examples of the compound synthesized by Scheme 12 are as follows.

The definition of R ₂₄ and h in Scheme 12 is the same as in Formula 4.

<Synthesis Example 12-1> Synthesis of Compound 12-1

In Synthesis Example 6-1, compound 9-1-A (15.9 g, 48.8 mmol) instead of compound 6-1-A, and compound 8-1-B (23.3 g, 102.4 mmol) instead of compound 6-1-B were used. Except for that, compound 12-1 (12.6 g, yield 50%; MS:[M+H] ⁺ =517) was obtained in the same manner as in Synthesis Example 6-1.

[Scheme 13]

P11 (1.0 eq.), P12 (1.05 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.02 eq.), K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) were added to Dioxane and refluxed. Compound M was obtained. Examples of the compound synthesized by Scheme 13 are as follows.

In Reaction Scheme 13, the definitions of X ₁ , X ₂ , X ₃ , R ₂₄ , h, R ₂₉ and n are the same as in Chemical Formula 4.

<Synthesis Example 13-1> Synthesis of Compound 13-1

In Synthesis Example 6-1, compound 13-1-A (23.8 g, 48.8 mmol) instead of compound 6-1-A, and compound 8-1-B (23.3 g, 102.4 mmol) instead of compound 6-1-B were used. Except for that, compound 13-1 (16.0 g, yield 57%; MS:[M+H] ⁺ =576) was obtained in the same manner as in Synthesis Example 6-1.

<Synthesis Examples 13-2 to 13-16> Synthesis of compounds 13-2 to 13-16

By changing X ₁ , X ₂ , X ₃ , R ₂₄ , h, R ₂₉ and n in Scheme 13, compounds 13-2 to 13-16 were synthesized in the same manner as in Scheme 13.

[Scheme 14]

P13-1 (1.05 eq.), P13 (1.05 eq.), P14 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.03 eq.), K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) was added to dioxane and refluxed to obtain compound N. Examples of the compound synthesized by Scheme 14 are as follows.

In Scheme 14, R"', L ₁ , R ₃₂ , r and R _a have the same definitions as in Formula 6.

<Synthesis Example 14-1> Synthesis of Compound 14-1

In Synthesis Example 6-1, compound 14-1-A (27.0 g, 48.8 mmol) instead of compound 6-1-A and compound 14-1-B (21.8 g, 102.4 mmol) instead of compound 6-1-B Except that, compound 14-1 (18.4 g, yield 69%; MS:[M+H] ⁺ =548) was obtained in the same manner as in Synthesis Example 6-1.

<Synthesis Examples 14-2 to 14-5> Synthesis of compounds 14-2 to 14-5

By changing R"', L ₁ , R ₃₂ , r and R _a in Scheme 14, compounds 14-2 to 14-5 were synthesized in the same manner as in Scheme 14.

[Scheme 15]

P13 (1.05 eq.), P15 (1.0 eq.), Tetrakis(triphenylphosphine) palladium(0) (0.03 eq.), K ₂ CO ₃ (aq.) (3.0 eq., 0.2M) was added to dioxane and refluxed. Compound P was obtained. Examples of the compound synthesized by Scheme 15 are as follows.

In Scheme 15, R"', L ₁ , R ₃₂ , r and R _a have the same definitions as in Formula 6.

<Synthesis Example 15-1> Synthesis of Compound 15-1

In Synthesis Example 6-1, compound 15-1-A (19.4 g, 48.8 mmol) instead of compound 6-1-A, and compound 15-1-B (33.0 g, 102.4 mmol) instead of compound 6-1-B were used. Except that, compound 15-1 (23.5 g, yield 81%; MS:[M+H] ⁺ =560) was obtained in the same manner as in Synthesis Example 6-1.

<Synthesis Examples 15-2 to 15-15> Synthesis of compounds 15-2 to 15-15

By changing R"', L ₁ , R ₃₂ , r and R _a in Scheme 15, compounds 15-2 to 15-15 were synthesized in the same manner as in Scheme 14.

Experimental example

<Experimental Example 1-1>

Compound 1-1 obtained in Synthesis Example 1-1 was vacuum deposited on a substrate to form a light efficiency improvement layer of 600 Å. The electrode used thereon was formed using a glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 500 Å. The indium tin oxide (ITO) substrate was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and the distilled water was manufactured by Millipore Co. Distilled water filtered secondarily with a filter was used. After washing indium tin oxide (ITO) for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then used. On the electrode thus formed, hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 100 Å to form a hole injection layer.

A hole transport layer was formed by vacuum depositing 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (1,000 Å) of the above formula on the hole injection layer. Subsequently, on the hole transport layer, a light emitting layer was formed by vacuum depositing the following BH and BD at a weight ratio of 25:1 with a thickness of 200 Å.

On the emission layer, the ET-A and lithium quinolate (LiQ: Lithium Quinolate) of the following formula were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 300 Å.

Lithium fluoride (LiF) to a thickness of 15 Å and aluminum were sequentially deposited on the electron injection and transport layer to a thickness of 2,000 Å to form a negative electrode. In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2 × 10. Maintaining ^-7 ~ 5 × 10 ^-8 torr, an organic light emitting device was manufactured.

<Experimental Examples 1-2 to 1-136>

In Experimental Example 1-1, an organic light emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of compound 1-1.

Comparative Example 1-1

In Experimental Example 1-1, an organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the light efficiency improving material was not used.

Comparative Example 1-2

In Experimental Example 1-1, an organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Alq ₃ was used instead of Compound 1-1.

Evaluation example

When a current (10 mA/cm ² ) was applied to the organic light emitting devices manufactured according to Experimental Examples 1-1 to 1-136, Comparative Example 1-1, and Comparative Example 1-2, the results of Table 1 were obtained.

compound efficiency
(cd/A) Color coordinates
(x, y) Experimental Example 1-1 1-1 5.20 (0.140, 0.129) Experimental Example 1-2 1-2 5.19 (0.139, 0.130) Experimental Example 1-3 1-3 5.10 (0.138, 0.130) Experimental Example 1-4 1-4 5.11 (0.140, 0.129) Experimental Example 1-5 1-5 5.10 (0.140, 0.130) Experimental Example 1-6 1-6 5.21 (0.140, 0.131) Experimental Example 1-7 1-7 5.19 (0.139, 0.130) Experimental Example 1-8 1-8 5.18 (0.141, 0.129) Experimental Example 1-9 1-9 5.18 (0.140, 0.129) Experimental Example 1-10 1-10 5.20 (0.139, 0.129) Experimental Example 1-11 1-11 5.21 (0.138, 0.130) Experimental Example 1-12 1-12 5.22 (0.140, 0.130) Experimental Example 1-13 1-13 5.20 (0.141, 0.130) Experimental Example 1-14 1-14 5.19 (0.140, 0.131) Experimental Example 1-15 1-15 5.18 (0.141, 0.129) Experimental Example 1-16 1-16 5.17 (0.139, 0.129) Experimental Example 1-17 1-17 5.18 (0.138, 0.128) Experimental Example 1-18 1-18 5.20 (0.140, 0.128) Experimental Example 1-19 1-19 5.20 (0.140, 0.130) Experimental Example 1-20 1-20 5.22 (0.139, 0.131) Experimental Example 1-21 1-21 5.20 (0.138, 0.131) Experimental Example 1-22 1-22 5.19 (0.141, 0.129) Experimental Example 1-23 1-23 5.19 (0.140, 0.130) Experimental Example 1-24 1-24 5.21 (0.140, 0.128) Experimental Example 1-25 1-25 5.21 (0.139, 0.130) Experimental Example 1-26 1-26 5.22 (0.138, 0.131) Experimental Example 1-27 1-27 5.21 (0.139, 0.130) Experimental Example 1-28 1-28 5.20 (0.140, 0.129) Experimental Example 1-29 1-29 5.18 (0.141, 0.128) Experimental Example 1-30 1-30 5.23 (0.139, 0.130) Experimental Example 1-31 2-1 4.99 (0.141, 0.129) Experimental Example 1-32 2-2 5.00 (0.140, 0.130) Experimental Example 1-33 3-1 5.23 (0.140, 0.129) Experimental Example 1-34 3-2 5.19 (0.141, 0.130) Experimental Example 1-35 3-3 5.21 (0.141, 0.128) Experimental Example 1-36 3-4 5.24 (0.141, 0.129) Experimental Example 1-37 3-5 5.22 (0.140, 0.128) Experimental Example 1-38 3-6 5.18 (0.139, 0.130) Experimental Example 1-39 3-7 5.16 (0.140, 0.128) Experimental Example 1-40 3-8 5.20 (0.141, 0.128) Experimental Example 1-41 3-9 5.19 (0.139, 0.130) Experimental Example 1-42 3-10 5.12 (0.139, 0.129) Experimental Example 1-43 3-11 5.21 (0.141, 0.128) Experimental Example 1-44 3-12 5.18 (0.139, 0.129) Experimental Example 1-45 4-1 5.21 (0.140, 0.129) Experimental Example 1-46 4-2 5.20 (0.139, 0.130) Experimental Example 1-47 4-3 5.19 (0.140, 0.129) Experimental Example 1-48 4-4 5.23 (0.139, 0.130) Experimental Example 1-49 4-5 5.20 (0.140, 0.129) Experimental Example 1-50 4-6 5.19 (0.141, 0.128) Experimental Example 1-51 4-7 4.92 (0.140, 0.130) Experimental Example 1-52 4-8 5.24 (0.139, 0.130) Experimental Example 1-53 4-9 5.20 (0.141, 0.128) Experimental Example 1-54 4-10 5.18 (0.141, 0.129) Experimental Example 1-55 4-11 5.19 (0.140, 0.128) Experimental Example 1-56 4-12 5.15 (0.139, 0.130) Experimental Example 1-57 4-13 5.17 (0.141, 0.128) Experimental Example 1-58 4-14 5.19 (0.140, 0.130) Experimental Example 1-59 4-15 5.20 (0.140, 0.129) Experimental Example 1-60 4-16 4-99 (0.139, 0.130) Experimental Example 1-61 4-17 5.19 (0.139, 0.130) Experimental Example 1-62 4-18 5.24 (0.139, 0.130) Experimental Example 1-63 4-19 5.20 (0.140, 0.130) Experimental Example 1-64 4-20 4.99 (0.139, 0.130) Experimental Example 1-65 4-21 5.19 (0.140, 0.129) Experimental Example 1-66 5-1 5.18 (0.141, 0.129) Experimental Example 1-67 5-2 5.22 (0.141, 0.128) Experimental Example 1-68 5-3 5.20 (0.141, 0.129) Experimental Example 1-69 5-4 5.12 (0.140, 0.128) Experimental Example 1-70 5-5 5.20 (0.139, 0.130) Experimental Example 1-71 5-6 5.23 (0.141, 0.129) Experimental Example 1-72 5-7 5.19 (0.139, 0.130) Experimental Example 1-73 5-8 5.18 (0.140, 0.128) Experimental Example 1-74 5-9 5.20 (0.141, 0.128) Experimental Example 1-75 5-10 5.20 (0.141, 0.129) Experimental Example 1-76 5-11 5.21 (0.140, 0.128) Experimental Example 1-77 5-12 5.18 (0.139, 0.130) Experimental Example 1-78 5-13 5.20 (0.139, 0.130) Experimental Example 1-79 5-14 5.21 (0.139, 0.130) Experimental Example 1-80 5-15 5.19 (0.140, 0.130) Experimental Example 1-81 5-16 5.19 (0.139, 0.130) Experimental Example 1-82 5-17 5.21 (0.141, 0.129) Experimental Example 1-83 5-18 5.23 (0.139, 0.130) Experimental Example 1-84 5-19 5.24 (0.139, 0.130) Experimental Example 1-85 5-20 5.19 (0.140, 0.130) Experimental Example 1-86 5-21 5.22 (0.139, 0.130) Experimental Example 1-87 6-1 5.19 (0.141, 0.128) Experimental Example 1-88 6-2 5.21 (0.141, 0.129) Experimental Example 1-89 6-3 5.21 (0.140, 0.128) Experimental Example 1-90 6-4 5.20 (0.139, 0.130) Experimental Example 1-91 6-5 5.19 (0.139, 0.130) Experimental Example 1-92 6-6 5.22 (0.139, 0.130) Experimental Example 1-93 6-7 5.23 (0.141, 0.128) Experimental Example 1-94 6-8 5.19 (0.141, 0.129) Experimental Example 1-95 7-1 5.19 (0.140, 0.128) Experimental Example 1-96 8-1 5.18 (0.139, 0.130) Experimental Example 1-97 9-1 5.23 (0.139, 0.130) Experimental Example 1-98 10-1 5.22 (0.139, 0.130) Experimental Example 1-99 11-1 5.21 (0.141, 0.128) Experimental Example 1-100 12-1 5.23 (0.141, 0.129) Experimental Example 1-101 13-1 5.23 (0.140, 0.128) Experimental Example 1-102 13-2 5.25 (0.139, 0.130) Experimental Example 1-103 13-3 5.19 (0.139, 0.130) Experimental Example 1-104 13-4 5.22 (0.139, 0.130) Experimental Example 1-105 13-5 5.19 (0.141, 0.128) Experimental Example 1-106 13-6 5.24 (0.141, 0.129) Experimental Example 1-107 13-7 5.19 (0.140, 0.128) Experimental Example 1-108 13-8 5.18 (0.139, 0.130) Experimental Example 1-109 13-9 5.21 (0.139, 0.130) Experimental Example 1-110 13-10 5.23 (0.139, 0.130) Experimental Example 1-111 13-11 5.21 (0.139, 0.130) Experimental Example 1-112 13-12 5.20 (0.141, 0.128) Experimental Example 1-113 13-13 5.18 (0.140, 0.129) Experimental Example 1-114 13-14 5.22 (0.139, 0.130) Experimental Example 1-115 13-15 5.24 (0.138, 0.130) Experimental Example 1-116 13-16 5.19 (0.140, 0.129) Experimental Example 1-117 14-1 5.19 (0.140, 0.130) Experimental Example 1-118 14-2 5.21 (0.140, 0.129) Experimental Example 1-119 14-3 5.20 (0.141, 0.130) Experimental Example 1-120 14-4 5.20 (0.140, 0.130) Experimental Example 1-121 14-5 5.21 (0.139, 0.130) Experimental Example 1-122 15-1 5.18 (0.141, 0.130) Experimental Example 1-123 15-2 5.26 (0.140, 0.131) Experimental Example 1-124 15-3 5.19 (0.141, 0.129) Experimental Example 1-125 15-4 5.22 (0.139, 0.129) Experimental Example 1-126 15-5 5.24 (0.140, 0.128) Experimental Example 1-127 15-6 5.28 (0.139, 0.130) Experimental Example 1-128 15-7 5.25 (0.139, 0.130) Experimental Example 1-129 15-8 5.22 (0.141, 0.129) Experimental Example 1-130 15-9 5.24 (0.139, 0.130) Experimental Example 1-131 15-10 5.27 (0.140, 0.129) Experimental Example 1-132 15-11 5.22 (0.139, 0.130) Experimental Example 1-133 15-12 5.28 (0.138, 0.130) Experimental Example 1-134 15-13 5.26 (0.140, 0.129) Experimental Example 1-135 15-14 5.23 (0.140, 0.130) Experimental Example 1-136 15-15 5.28 (0.139, 0.129) Comparative Example 1-1 - 3.91 (0.152, 0.146) Comparative Example 1-2 Alq ₃ 4.61 (0.140, 0.129)

From the results of Table 1, the compound according to the exemplary embodiment of the present specification can be used as a material for an organic material layer of an organic light-emitting device. In particular, when used for a light efficiency improvement layer among organic material layers, the organic light-emitting device has excellent properties It can be seen that it represents.

10, 11, 12: organic light emitting device
20: substrate
30: anode
40: organic layer
50: cathode
60, 61, 62: light efficiency improvement layer

Claims (31)

Board;
An anode and a cathode provided on the substrate;
One or more organic layers provided between the anode and the cathode; And
At least one of the anode and the cathode, including a light efficiency improvement layer provided on a surface opposite to the surface facing the organic layer,
The light efficiency improvement layer is an organic light-emitting device comprising a compound represented by any one of the following Chemical Formulas 3 to 6:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Chemical Formula 3,
X ₁ is O or S, X ₂ is O or S,
R ₂₀ to R ₂₃ are hydrogen, d and q are 4, e and f are 3,
L ₂ is bivalent

Is,
In Formula 4,
X ₁ to X ₃ are the same as or different from each other, and each independently O or S,
L ₃ and L ₄ are the same as or different from each other, and each independently a direct bond; Arylene group; Divalent quinoline group; Or a divalent pyridine group,
R ₂₄ to R ₂₉ are the same as or different from each other, and each independently hydrogen; Or an aryl group, or adjacent groups are bonded to each other to form a benzene ring,
In Formulas 5 and 6, X is O or S,
L ₁ is a direct bond; F, an arylene group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A heteroarylene group including O or S; Divalent quinoline group; A divalent pyridine group; Divalent pyrimidine group; Divalent pyridazine group; A divalent phenanthroline group; Or a divalent indole group substituted with an alkyl group,
R ₃₀ to R ₃₂ are the same as or different from each other, and each independently F; Cyano group; F, a cyano group, an aryl group unsubstituted or substituted with an alkyl group or an aryl group; Or phenyl-benzophosphinedol-oxide, or adjacent groups are bonded to each other to form an aromatic ring,
R'and R" are the same as or different from each other, and each independently F, a cyano group, an alkyl group, an aryl group, a heteroaryl group including O or S, a quinoline group, a pyridine group, a pyrimidine group, a pyridazine group, a p Nanthrolene group, an indole group substituted with an alkyl group, or an aryl group unsubstituted or substituted with a phenyl-benzophospindol-oxide; a heteroaryl group including O or S; a quinoline group; a pyridine group; a pyrimidine group; a pyridazine group ; Phenanthroline group; an indole group substituted with an alkyl group; or phenyl-benzophospindol-oxide,
R"' is a tetrahydroacridine group substituted with an alkyl group or an aryl group; a dihydrophenoxazine group substituted with an alkyl group or an aryl group; or a dihydrophenothiazine group substituted with an alkyl group or an aryl group,
i, j, k, m, and s are the same as or different from each other, and each independently an integer of 1 to 3,
h, n, p and r are the same as or different from each other, and each independently an integer of 1 to 4,
When the h, i, j, k, m, n, p, q, r or s are 2 or more, the substituents in the parentheses are the same or different from each other. delete delete delete delete delete delete delete The method according to claim 1,
The R'and R" are the same as or different from each other, and each independently F, a cyano group, an alkyl group, an aryl group, a heteroaryl group including O or S, a quinoline group, a pyridine group, a pyrimidine group, a pyridazine group, A phenanthrolene group, an indole group substituted with an alkyl group, or a phenyl group unsubstituted or substituted with phenyl-benzophosphindol-oxide; F, a cyano group, an alkyl group, an aryl group, a heteroaryl group including O or S, a quinoline group, A pyridine group, a pyrimidine group, a pyridazine group, a phenanthrolene group, an indole group substituted with an alkyl group, or a biphenyl group unsubstituted or substituted with a phenyl-benzophospindol-oxide; F, a cyano group, an alkyl group, an aryl group, O Or a heteroaryl group containing S, a quinoline group, a pyridine group, a pyrimidine group, a pyridazine group, a phenanthrolene group, an indole group substituted with an alkyl group, or a terphenyl group unsubstituted or substituted with a phenyl-benzophosphindol-oxide ; F, cyano group, alkyl group, aryl group, heteroaryl group including O or S, quinoline group, pyridine group, pyrimidine group, pyridazine group, phenanthrolene group, indole group or phenyl-benzo substituted with an alkyl group Naphthyl group unsubstituted or substituted with phosphindol-oxide; substituted or unsubstituted fluorenyl group; pyridyl group; triphenylenyl group; fluoranthenyl group; quinolinyl group; phenanthrenyl group; and dibenzofuran group The organic light emitting device is selected from. The method according to claim 1,
L ₁ is a direct bond; F, a cyano group, an alkyl group, or a phenylene group unsubstituted or substituted with an aryl group; Naphthylene group; Biphenylylene group; A fluorenylene group unsubstituted or substituted with an alkyl group or an aryl group; Divalent dibenzofuran group; Divalent dibenzothiophene group; Pyridazinylene group; Benzofuran group; Divalent benzothiophene group; Pyrenylene group; Pyrimidine group; Quinolinylene group; Divalent triphenylene group; Furanylene group; Pyridylene group; Anthracenylene group; Divalent thiophene group; A divalent phenanthroline group; Phenylene group-naphthylene group; Anthracenylene group-phenylene group; Or an organic light emitting device that is an indolylene group unsubstituted or substituted with an alkyl group. delete delete delete delete delete The method according to claim 1,
Formula 4 is an organic light-emitting device represented by any one of the following Formulas 4-4 to 4-7, 4-14, and 4-16:
[Formula 4-4]

[Formula 4-5]

[Formula 4-6]

[Formula 4-7]

[Formula 4-14]

[Formula 4-16]

In Formulas 4-4 to 4-7, 4-14 and 4-16,
R ₂₄ to R ₂₉ , L ₃ , L ₄ , h, i, j, k, m and n are the same as in Chemical Formula 4. The method according to claim 1,
Formula 5 is an organic light emitting device represented by any one of the following Formulas 5-2 and 5-3:
[Formula 5-2]

[Chemical Formula 5-3]

In Formulas 5-2 and 5-3,
R ₃₀ , R ₃₁ , L ₁ , R', R", p and q are the same as in Chemical Formula 5. delete delete The organic light-emitting device of claim 1, wherein the compound represented by Formula 3 is represented by the following compound:

The organic light-emitting device of claim 1, wherein the compound represented by Formula 4 is selected from the following compounds:

The organic light-emitting device of claim 1, wherein the compound represented by Formula 5 or 6 is selected from the following compounds:

delete The organic light-emitting device of claim 1, wherein the anode is a transmissive electrode, and the light efficiency improvement layer is provided on a surface opposite to a surface of the anode facing the organic layer. The organic light-emitting device as set forth in claim 1, wherein the cathode is a transmissive electrode, and the light efficiency improvement layer is provided on a surface of the cathode opposite to a surface facing the organic layer. The method according to claim 1, wherein the anode and the cathode are transmissive electrodes, and the light efficiency improvement layer is provided on each of a surface opposite to a surface of the anode facing the organic layer and a surface opposite to a surface of the cathode facing the organic layer. An organic light-emitting device characterized by. The organic light-emitting device of claim 1, wherein the organic layer is patterned for each of R, G, and B pixels, and the light efficiency improvement layer is formed as a common layer for the R, G, and B pixels. The method according to claim 1, wherein the organic layer is patterned for each R, G, and B pixel, and the light efficiency improvement layer is for the R, G, and B pixels,
A light efficiency improvement layer-R formed in a region corresponding to the R pixel,
A light efficiency improvement layer-G formed in a region corresponding to the G pixel, and
An organic light-emitting device comprising at least one of the light efficiency improvement layer-B formed in a region corresponding to the pixel B. The organic light-emitting device of claim 28, wherein the light efficiency improvement layer-R, the light efficiency improvement layer-G, and the light efficiency improvement layer-B have the same or different thickness. The organic light-emitting device of claim 28, wherein the light efficiency improvement layer comprises a light efficiency improvement layer-R, a light efficiency improvement layer-G, and a light efficiency improvement layer-B. The method according to claim 28, wherein the light efficiency improvement layer-R, the light efficiency improvement layer-G, and the light efficiency improvement layer-B of the light efficiency improvement layer are formed with the organic layer of the anode in regions corresponding to R, G, and B pixels, respectively. An organic light-emitting device, characterized in that it is provided on each of a surface opposite to an opposite surface and a surface opposite to the organic layer of the cathode.

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