KR20220007271A - Composition, depositing source, organic electroluminescent device comprising same and method of manufacturung same - Google Patents

Abstract

The present specification provides a composition including a first compound and a second compound, a depositing source, an organic electroluminescent device comprising the same, and a method of manufacturing the same. According to at least one embodiment, the composition can improve color purity, efficiency, and lifespan characteristics in an organic electroluminescent device.

Description

Composition, deposition source, organic electroluminescent device comprising same, and method for manufacturing the same

The present specification relates to a composition, a deposition source, an organic electroluminescent device including the same, and a method for manufacturing the same.

The organic electroluminescent device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic electroluminescent device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

As materials used in organic electroluminescent devices, pure organic materials or complex compounds in which an organic material and a metal are complexed account for most, and depending on the use, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material It can be divided into Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used. As the light emitting layer material, a material having both p-type and n-type properties, that is, a material having a stable form in both oxidation and reduction states, is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed. A material with high luminous efficiency that converts it into light when it is formed is preferable.

In order to improve the performance, lifespan or efficiency of an organic electroluminescent device, the development of a material for an organic thin film is continuously required.

Korean Publication No. 10-2016-0119683

The present specification provides a composition, a deposition source, an organic electroluminescent device including the same, and a method for manufacturing the same.

An exemplary embodiment of the present specification provides a composition comprising a first compound represented by the following formula (1) and a second compound represented by the following formula (2).

[Formula 1]

In Formula 1,

A1 is a substituted or unsubstituted aromatic heterocycle including S; A substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted, condensed ring of an aromatic heterocyclic ring and an aliphatic hydrocarbon ring containing S; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

A2 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

r1 is an integer from 1 to 3,

When r1 is 2 or more, the 2 or more R1 are the same as or different from each other,

[Formula 2]

In Formula 2,

Y is B; N; P=O; or P=S,

X1 and X2 are the same as or different from each other, and each independently O; S; Se; CR11R12; And selected from the group consisting of NR13,

R2 to R4 and R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; nitro group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

r2 and r3 are each an integer of 1 to 4,

r4 is an integer from 1 to 3,

When r2 to r4 are 2 or more, the substituents in the parentheses are the same as or different from each other.

In addition, an exemplary embodiment of the present specification provides a deposition source manufactured using the composition.

In addition, one embodiment of the present specification is an anode; cathode; And an organic electroluminescent device comprising one or more organic material layers provided between the anode and the cathode, wherein at least one of the organic material layers provides an organic electroluminescent device comprising the composition.

Finally, one embodiment of the present specification comprises the steps of preparing a substrate; forming an anode on the substrate; forming one or more organic material layers on the anode; and forming a cathode on the organic material layer, wherein the forming of the one or more organic material layers comprises the step of forming one or more organic material layers using the composition A method of manufacturing an organic electroluminescent device to provide.

The composition described herein may be used as a material for an organic layer of an organic electroluminescent device. The composition according to at least one embodiment may improve color purity, efficiency, and lifespan characteristics in an organic electroluminescent device. In particular, the composition described herein can be used as a material for hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material.

1 shows an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked.
2 is a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a first electron transport layer (7), a second electron transport layer (8) shows an example of an organic electroluminescent device in which the electron injection layer 9 and the cathode 10 are sequentially stacked.

Hereinafter, the present specification will be described in detail.

The composition according to an exemplary embodiment of the present specification is a composition including the first compound represented by Formula 1 and the second compound represented by Formula 2, and excellent efficiency when manufacturing an organic electroluminescent device including the composition It is possible to obtain a device with improved lifespan and color purity while maintaining

When the difference between the maximum emission wavelength of the first compound and the maximum emission wavelength (λmax) of the second compound exceeds 15 nm, quantum efficiency and/or lifetime characteristics increase.

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

In this specification, when a member is said to be located "on" another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

In the present specification, the maximum emission wavelength of the compound may be measured using a JASCO FP-8600 fluorescence spectrophotometer as a measuring device. The specific measurement method is as follows. A sample solution for measurement is prepared by dissolving the compound in the solvent toluene at a concentration of 1 M. A sample solution is placed in a quartz cell, and _{oxygen in the solution is removed by degassing using nitrogen gas (N 2} ), and then the absorption spectrum is measured at room temperature (300 K) using a measuring device. At this time, in the measured absorption spectrum, the x-axis is the wavelength (λ, unit: nm) and the y-axis is the absorbance. The band width of the spectrum at the point at which the y value is half of the maximum emission peak of the absorption spectrum is called full width at half maximum (FWHM).

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group (-CN); nitro group; hydroxyl group; amine group; silyl group; boron group; alkoxy group; aryloxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group (-CN); amine group; silyl group; alkoxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

As used herein, the term "substituted or unsubstituted" refers to an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

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

In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

In the present specification, the silyl group may be represented by the formula of _{-SiY a} Y _b Y _{c , wherein Y a} , Y _b and Y _c are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. does not

In the present specification, the boron group may be represented by the formula of _{-BY d} Y _{e , wherein Y d} and Y _e are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but are not limited thereto.

In the present specification, the description of the above-described alkyl group may be applied, except that the arylalkyl group is substituted with an aryl group.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto. .

The substituents containing an alkyl group, an alkoxy group, and other alkyl group moieties described herein include both straight-chain or pulverized forms.

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

In the present specification, the alkynyl group is a substituent including a triple bond between a carbon atom and a carbon atom, and may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ , and the amine group may be substituted with the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the carbon number of the amine group is 1 to 20. According to an exemplary embodiment, the carbon number of the amine group is 1 to 10. Specific examples of the substituted amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, and a diphenylamine group. group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, There is a ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, or a quaterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto no.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

spirofluorenyl groups such as

(9,9-dimethyl fluorenyl group), and

a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the description of the above-described aryl group may be applied to the aryl group in the aryloxy group.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group , a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like, but are not limited thereto.

In the present specification, the description of the above-described heterocyclic group may be applied, except that the heteroaryl group is aromatic.

In the present specification, in a substituted or unsubstituted ring formed by bonding with an adjacent group, "ring" is a hydrocarbon ring; or a heterocyclic ring.

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 divalent group.

In the present specification, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring thereof. The hydrocarbon ring means a ring consisting of only carbon and hydrogen atoms. The heterocycle means a ring including at least one selected from N, O, P, S, Si and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle and the aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, the aliphatic hydrocarbon ring is a non-aromatic ring and refers to a ring consisting only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. However, the present invention is not limited thereto.

In the present specification, the aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.

In the present specification, the aromatic heterocycle including S means an aromatic ring including at least one heteroatom S.

In the present specification, the aromatic heterocycle refers to an aromatic ring including one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, paraazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiazole. Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazaindene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but is not limited thereto.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiment of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

A1 is a substituted or unsubstituted aromatic heterocycle including S; A substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted, condensed ring of an aromatic heterocyclic ring and an aliphatic hydrocarbon ring containing S; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

A2 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

r1 is an integer from 1 to 3,

When r1 is 2 or more, the 2 or more R1s are the same as or different from each other.

According to an exemplary embodiment of the present specification, "adjacent group" in the definition of Ar1 means at least one of A1 and R1, and "adjacent group" in the definition of Ar2 means at least one of A2 and R1 do.

According to an exemplary embodiment of the present specification, "adjacent group" in the definition of R1 means two or more R1 bonded at an ortho position when r1 is two or more.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

Ar1, Ar2, R1, r1 and A2 are the same as defined in Formula 1 above,

A'1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

A3 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-1-1 or 1-1-2.

[Formula 1-1-1]

[Formula 1-1-2]

In Formulas 1-1-1 and 1-1-2,

The definitions of A2, Ar1, Ar2, R1 and r1 are the same as defined in Formula 1 above,

A "1 is a substituted or unsubstituted aliphatic hydrocarbon ring,

R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

r101 is an integer of 1 to 4, and when r101 is 2 or more, R101 of 2 or more are the same as or different from each other,

r102 is 1 or 2, and when r102 is 2, the two R102 are the same as or different from each other.

According to an exemplary embodiment of the present specification, A1 is a substituted or unsubstituted, monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms including S; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a substituted or unsubstituted, condensed ring of a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms including S; or a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms. A1 may include deuterium.

According to an exemplary embodiment of the present specification, A1 is a substituted or unsubstituted, monocyclic or polycyclic aromatic heterocycle having 2 to 20 carbon atoms including S; a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; a substituted or unsubstituted, condensed ring of a monocyclic or polycyclic aromatic heterocycle having 2 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms including S; or a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A1 is a monocyclic ring having 2 to 30 carbon atoms including S and unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 30 carbon atoms. or a polycyclic aromatic heterocyclic ring; Deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a straight or branched chain alkoxy group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a cycloalkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic aryl having 6 to 30 carbon atoms, unsubstituted or substituted with a straight or branched alkylsilyl group, a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, or a straight or branched chain alkyl group having 1 to 30 carbon atoms a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a group and a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; A condensed ring of a monocyclic or polycyclic aromatic heterocycle having 2 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms and includes S ; Or a condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A1 is a monocyclic ring having 2 to 20 carbon atoms including S and unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 20 carbon atoms. or a polycyclic aromatic heterocyclic ring; Deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a straight or branched chain alkoxy group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms A monocyclic or polycyclic aryl having 6 to 20 carbon atoms unsubstituted or substituted with a straight or branched alkylsilyl group, a monocyclic or polycyclic diarylamine group having 6 to 20 carbon atoms, or a straight or branched chain alkyl group having 1 to 20 carbon atoms a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, unsubstituted or substituted with one or more substituents selected from the group consisting of a group and a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms; A condensed ring of a monocyclic or polycyclic aromatic heterocycle having 2 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms, which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 20 carbon atoms and includes S ; Or a condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms, which are unsubstituted or substituted with a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A1 is deuterium, F, cyano group, methyl group, t-butyl group, methoxy group, cyclohexyl group, trimethylsilyl group, phenyl group, diphenylamine group, carbazole group, dibenzofuran benzene unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a dibenzothiophene group and a dimethyl fluorenyl group; naphthalene; tetrahydronaphthalene substituted with a methyl group; dihydroindene substituted with a methyl group; benzothiophene unsubstituted or substituted with a methyl group or a t-butyl group; tetrahydronaphthothiophene substituted with a methyl group; or dihydroindenothiophene substituted with a methyl group.

According to an exemplary embodiment of the present specification, A1 is F, a cyano group, a methyl group, a t-butyl group, a methoxy group, a cyclohexyl group, a trimethylsilyl group, a phenyl group, a diphenylamine group, a carbazole group, a dibenzofuran group, benzene unsubstituted or substituted with one or more substituents selected from the group consisting of a dibenzothiophene group and a dimethyl fluorenyl group; naphthalene; tetrahydronaphthalene substituted with a methyl group; dihydroindene substituted with a methyl group; benzothiophene unsubstituted or substituted with a methyl group or a t-butyl group; tetrahydronaphthothiophene substituted with a methyl group; or dihydroindenothiophene substituted with a methyl group.

According to an exemplary embodiment of the present specification, A1 is benzene substituted with a methyl group; or tetrahydronaphthalene substituted with a methyl group.

이다. 상기 구조에서, *는 상기 화학식 1에 축합되는 위치를 의미한다.According to an exemplary embodiment of the present specification, A1 is benzene substituted with a methyl group; or

to be. In the above structure, * means a position condensed in Formula 1 above.

According to an exemplary embodiment of the present specification, A'1 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, A'1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A'1 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; or a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A'1 is deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a straight or branched chain alkoxy group having 1 to 30 carbon atoms, 3 to carbon atoms Substituted with a monocyclic or polycyclic cycloalkyl group having 30 carbon atoms, a linear or branched alkylsilyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms, or a straight or branched chain alkyl group having 1 to 30 carbon atoms Or an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, monocyclic or unsubstituted or unsubstituted with one or more substituents selected from the group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms or polycyclic aromatic hydrocarbon ring; Or a condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms, unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A'1 is deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a straight or branched chain alkoxy group having 1 to 20 carbon atoms, 3 to carbon atoms Substituted with a monocyclic or polycyclic cycloalkyl group having 20 carbon atoms, a linear or branched alkylsilyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic diarylamine group having 6 to 20 carbon atoms, or a linear or branched chain alkyl group having 1 to 20 carbon atoms Or an unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, monocyclic or unsubstituted or substituted with one or more substituents selected from the group consisting of 6 to 20 carbon atoms or polycyclic aromatic hydrocarbon ring; Or a condensed ring of a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms, which are unsubstituted or substituted with a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A'1 is deuterium, F, cyano group, methyl group, t-butyl group, methoxy group, cyclohexyl group, trimethylsilyl group, phenyl group, diphenylamine group, carbazole group, di benzene unsubstituted or substituted with one or more substituents selected from the group consisting of a benzofuran group, a dibenzothiophene group, and a dimethylfluorenyl group; naphthalene; tetrahydronaphthalene substituted with a methyl group; or dihydroindene substituted with a methyl group.

According to an exemplary embodiment of the present specification, A'1 is F, cyano group, methyl group, t-butyl group, methoxy group, cyclohexyl group, trimethylsilyl group, phenyl group, diphenylamine group, carbazole group, dibenzofuran benzene unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a dibenzothiophene group and a dimethyl fluorenyl group; naphthalene; tetrahydronaphthalene substituted with a methyl group; or dihydroindene substituted with a methyl group.

According to an exemplary embodiment of the present specification, A'1 is benzene substituted with a methyl group; or tetrahydronaphthalene substituted with a methyl group.

이다. 상기 구조에서, *는 상기 화학식 1-1에 축합되는 위치를 의미한다.According to an exemplary embodiment of the present specification, A'1 is benzene substituted with a methyl group; or

to be. In the above structure, * means a position condensed in Formula 1-1.

According to an exemplary embodiment of the present specification, A2 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms. A2 may include deuterium.

According to an exemplary embodiment of the present specification, A2 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; or a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A2 is a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms; or a fused ring of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A2 is a monocyclic or polycyclic aromatic hydrocarbon having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 30 carbon atoms. ring; a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic ring having 3 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 30 carbon atoms It is a condensed ring of an aliphatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, A2 is a monocyclic or polycyclic aromatic hydrocarbon having 6 to 20 carbon atoms that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 20 carbon atoms. ring; a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 20 carbon atoms; Or a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic ring having 3 to 20 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 20 carbon atoms It is a condensed ring of an aliphatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, A2 is benzene unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a methyl group and a t-butyl group; tetrahydronaphthalene substituted with one or more substituents selected from the group consisting of deuterium and a methyl group; dihydroindene substituted with one or more substituents selected from the group consisting of deuterium and a methyl group; cyclohexane unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a methyl group; phenanthrene unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a methyl group; or bicyclooctane unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a methyl group.

According to an exemplary embodiment of the present specification, A2 is benzene unsubstituted or substituted with deuterium, a methyl group, or a t-butyl group; tetrahydronaphthalene substituted with a methyl group; or dihydroindene substituted with a methyl group.

According to an exemplary embodiment of the present specification, A2 is benzene unsubstituted or substituted with a t-butyl group.

According to an exemplary embodiment of the present specification, the above-described definition of A2 may be applied to A3.

According to an exemplary embodiment of the present specification, A”1 is a substituted or unsubstituted aliphatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, A″1 is a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, A″1 is a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A″ 1 is a C 3 to C 30 monocyclic or polycyclic aliphatic hydrocarbon ring unsubstituted or substituted with a C 1 to C 30 linear or branched alkyl group.

According to an exemplary embodiment of the present specification, A″ 1 is a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, A”1 is a cyclohexane ring substituted with a methyl group; or a cyclopentane ring substituted with a methyl group.

According to an exemplary embodiment of the present specification, A”1 is a cyclohexane ring substituted with a methyl group.

According to an exemplary embodiment of the present specification, A”1 is a tetramethylcyclohexane ring.

이다. 상기 구조에서, *는 상기 화학식 1-1-2에 축합되는 위치를 의미한다.According to an exemplary embodiment of the present specification, A”1 is

to be. In the above structure, * means a position condensed in Formula 1-1-2.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group. Ar1 and Ar2 may each independently include deuterium.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a fused ring group of a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently has 1 to unsubstituted or unsubstituted deuterium, a halogen group, a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. A linear or branched alkyl group of 30, a linear or branched alkoxy group of 1 to 30 carbons, a linear or branched alkenyl group of 2 to 30 carbons, a monocyclic or polycyclic cycloalkyl group of 3 to 30 carbons, a cycloalkyl group of 1 to 30 carbons Substituted with one or more substituents selected from the group consisting of a 30 linear or branched alkylsilyl group, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms and monocyclic or polycyclic aliphatic ring having 6 to 30 carbon atoms and unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aliphatic ring having 3 to 30 carbon atoms Condensed ring group of hydrocarbon ring; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently has 1 to unsubstituted or unsubstituted deuterium, a halogen group, a cyano group, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. A linear or branched alkyl group of 20, a linear or branched alkoxy group of 1 to 20 carbons, a linear or branched alkenyl group of 2 to 20 carbons, a monocyclic or polycyclic cycloalkyl group of 3 to 20 carbons, a cycloalkyl group of 1 to 20 carbons Substituted with one or more substituents selected from the group consisting of a linear or branched alkylsilyl group of 20, and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 20 carbon atoms or an unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms and monocyclic or polycyclic aliphatic having 6 to 20 carbon atoms and unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a linear or branched alkyl group having 1 to 20 carbon atoms Condensed ring group of hydrocarbon ring; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms that is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently deuterium, F, cyano group, methyl group, t-butyl group, phenyl group, dimethylfluorene group, biphenyl group, methoxy group, a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a vinyl group, a trimethylsilyl group, a t-butyl group substituted with a phenyl group, an isopropyl group substituted with a phenyl group, and a phenoxy group; a biphenyl group unsubstituted or substituted with deuterium, a t-butyl group, or a phenyl group; terphenyl group; naphthyl group; benzofuran group; dibenzofuran group; a carbazole group unsubstituted or substituted with a phenyl group; dibenzothiophene group; tetrahydronaphthyl group unsubstituted or substituted with a methyl group; Or a dihydroindene group substituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a t-butyl group and a phenyl group; a biphenyl group unsubstituted or substituted with a t-butyl group; Or a tetrahydronaphthyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, when r1 is 2 or more, two or more R1s combine with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, when r1 is 2 or more, two or more R1s combine with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, when r1 is 2 or more, two or more R1s combine with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, when r1 is 2 or more, two or more R1s combine with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, when r1 is 2 or more, two or more R1s combine with an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, when r1 is 2 or more, two or more R1s combine with an adjacent group to form a benzene ring.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted C1-C30 linear or branched alkoxy group; a substituted or unsubstituted C6-C30 linear or branched arylalkyl group; a substituted or unsubstituted monocyclic or polycyclic aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C1-C30 linear or branched alkylsilyl group; a substituted or unsubstituted monocyclic or polycyclic amine group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. R1 may include deuterium.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted C1-C20 linear or branched alkoxy group; A substituted or unsubstituted C6-C20 linear or branched arylalkyl group; a substituted or unsubstituted monocyclic or polycyclic aryloxy group having 6 to 20 carbon atoms; A substituted or unsubstituted C1-C20 linear or branched alkylsilyl group; a substituted or unsubstituted monocyclic or polycyclic amine group having 6 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a linear or branched alkoxy group having 1 to 30 carbon atoms; a linear or branched arylalkyl group having 6 to 30 carbon atoms; a monocyclic or polycyclic aryloxy group having 6 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic amine group having 6 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms. The substituents are unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a linear or branched alkyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a linear or branched alkoxy group having 1 to 20 carbon atoms; a linear or branched arylalkyl group having 6 to 20 carbon atoms; a monocyclic or polycyclic aryloxy group having 6 to 20 carbon atoms; a linear or branched alkylsilyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic amine group having 6 to 20 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; F; cyano group; methyl group; a t-butyl group substituted with a phenyl group; t-butyl group; cyclohexyl group; phenyl group; trimethylsilyl group; methoxy group; phenoxy group; diphenylamine group; a carbazole group; or a hexahydrocarbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a methyl group and a t-butyl group. The substituents are unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; or a methyl group.

According to an exemplary embodiment of the present specification, R1 is hydrogen; or a methyl group.

According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a linear or branched alkyl group having 1 to 30 carbon atoms; a linear or branched alkoxy group having 1 to 30 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a linear or branched alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic diarylamine group having 6 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a linear or branched alkyl group having 1 to 20 carbon atoms; a linear or branched alkoxy group having 1 to 20 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a linear or branched alkylsilyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic diarylamine group having 6 to 20 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with a linear or branched alkyl group having 1 to 20 carbon atoms; Or it is a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; F; cyano group; methyl group; t-butyl group; methoxy group; cyclohexyl group; trimethylsilyl group; phenyl group; diphenylamine group; a carbazole group; dibenzofuran group; dibenzothiophene group; or a dimethylfluorenyl group, or adjacent groups combine with each other to form a benzene ring.

According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently hydrogen; F; cyano group; methyl group; t-butyl group; methoxy group; cyclohexyl group; trimethylsilyl group; phenyl group; diphenylamine group; a carbazole group; dibenzofuran group; dibenzothiophene group; or a dimethylfluorenyl group, or adjacent groups combine with each other to form a benzene ring.

According to an exemplary embodiment of the present specification, R101 is a methyl group.

According to an exemplary embodiment of the present specification, R102 is hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, R102 is hydrogen.

According to an exemplary embodiment of the present specification, r1 is 1.

According to an exemplary embodiment of the present specification, r1 is 2.

According to an exemplary embodiment of the present specification, r1 is 3.

According to an exemplary embodiment of the present specification, r101 is 1.

According to an exemplary embodiment of the present specification, r101 is 2.

According to an exemplary embodiment of the present specification, r101 is 3.

According to an exemplary embodiment of the present specification, r101 is 4.

According to an exemplary embodiment of the present specification, r102 is 1.

According to an exemplary embodiment of the present specification, r102 is 2.

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

Hereinafter, Chemical Formula 2 will be described in detail.

[Formula 2]

In Formula 2,

Y is B; N; P=O; or P=S,

X1 and X2 are the same as or different from each other, and each independently O; S; Se; CR11R12; And selected from the group consisting of NR13,

R2 to R4 and R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; nitro group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

r2 and r3 are each an integer of 1 to 4,

r4 is an integer from 1 to 3,

When r2 to r4 are 2 or more, the substituents in the parentheses are the same as or different from each other.

In the exemplary embodiment of the present specification, Y is B.

In an exemplary embodiment of the present specification, X1 and X2 are O.

In the exemplary embodiment of the present specification, X1 and X2 are S.

In the exemplary embodiment of the present specification, X1 and X2 are Se.

In an exemplary embodiment of the present specification, X1 and X2 are CR11R12.

In an exemplary embodiment of the present specification, X1 and X2 are NR13.

In an exemplary embodiment of the present specification, R2 to R4 and R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; nitro group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted heteroarylalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted alkylamine group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted arylalkylamine group; a substituted or unsubstituted heteroarylamine group; a substituted or unsubstituted alkylsilyl group; a substituted or unsubstituted arylsilyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, R2 to R4 and R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, R2 to R4 and R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or unsubstituted C2 to C30 ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, R2 to R4 and R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C6-C20 arylalkyl group; a substituted or unsubstituted C 3 to C 20 cycloalkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2 to C20 heterocyclic group, or a substituted or unsubstituted C2 to C20 ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 20 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2 to C20 heterocyclic group, or a substituted or unsubstituted C2 to C20 ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; an alkyl group unsubstituted or substituted with an aryl group; cycloalkyl group; a silyl group unsubstituted or substituted with an alkyl group; an amine group unsubstituted or substituted with an aryl group or an amine group; aryl group; or a heterocyclic group, or an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring unsubstituted or substituted with an alkyl group by combining with an adjacent group.

In an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; t-butyl group; a propyl group unsubstituted or substituted with a phenyl group; cyclohexyl group; trimethylsilyl group; an amine group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group and an amine group or two or more connected substituents; phenyl group; or a dibenzothiophene group, or a cyclohexane ring substituted with a benzene ring or a methyl group by combining with an adjacent group.

In an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; or a t-butyl group, or a cyclohexane ring substituted with a methyl group by combining with an adjacent group.

In an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently hydrogen; or a t-butyl group, or a cyclohexane ring substituted with a methyl group by combining with an adjacent group.

In an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group, or a substituted or unsubstituted ring is formed by bonding with an adjacent group.

In an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 20 cycloalkyl group; a substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted ring having 2 to 20 carbon atoms by combining with an adjacent group.

In an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; an alkyl group; cycloalkyl group; an amine group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a methyl group and a phenyl group; Or an aryl group unsubstituted or substituted with a heterocyclic group, or an aromatic hydrocarbon ring by bonding with an adjacent group.

In an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; methyl group; t-butyl group; cyclohexyl group; an amine group substituted with deuterium, a phenyl group, or a methylphenyl group; Or a phenyl group unsubstituted or substituted with a carbazole group or a dibenzofuran group, or a benzene ring by bonding with adjacent groups.

In an exemplary embodiment of the present specification, R4 is hydrogen; heavy hydrogen; or a methyl group.

In an exemplary embodiment of the present specification, R4 is hydrogen; or a methyl group.

In an exemplary embodiment of the present specification, R11 and R12 are substituted or unsubstituted alkyl groups.

In an exemplary embodiment of the present specification, R11 and R12 are a substituted or unsubstituted C1-C10 alkyl group.

In an exemplary embodiment of the present specification, R11 and R12 are methyl groups.

In an exemplary embodiment of the present specification, R13 is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or an aromatic hydrocarbon ring group in which a substituted or unsubstituted aliphatic hydrocarbon ring is condensed.

In an exemplary embodiment of the present specification, R13 is a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or an aromatic hydrocarbon ring group having 6 to 20 carbon atoms in which a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms is condensed.

In an exemplary embodiment of the present specification, R13 is an alkyl group; an aryl group unsubstituted or substituted with deuterium, an alkyl group, an aryl group, or a heterocyclic group; or an aromatic hydrocarbon ring group in which an aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group is condensed.

In an exemplary embodiment of the present specification, R13 is a methyl group; a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a methyl group, a t-butyl group, a phenyl group and a dibenzofuran group; a biphenyl group unsubstituted or substituted with a t-butyl group; Or a tetrahydronaphthyl group substituted with a methyl group.

로 표시되는 기이다.In an exemplary embodiment of the present specification, R13 is a methyl group; a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a methyl group, a t-butyl group, a phenyl group and a dibenzofuran group; or a biphenyl group unsubstituted or substituted with a t-butyl group,

is a group represented by

로 표시되는 기이다.In an exemplary embodiment of the present specification, R13 is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a t-butyl group and a phenyl group; or a biphenyl group unsubstituted or substituted with a t-butyl group,

is a group represented by

In an exemplary embodiment of the present specification, R13 is a phenyl group unsubstituted or substituted with a t-butyl group, or a group represented by any one of the following structural formulas.

로 표시되는 기이다.In an exemplary embodiment of the present specification, R13 is a phenyl group unsubstituted or substituted with a t-butyl group,

is a group represented by

In the exemplary embodiment of the present specification, r2 and r3 are each 1.

In one embodiment of the present specification, r2 and r3 are each 2.

In the exemplary embodiment of the present specification, r2 and r3 are each 3.

In the exemplary embodiment of the present specification, r2 and r3 are each 4.

In the exemplary embodiment of the present specification, r4 is 1.

In an exemplary embodiment of the present specification, r4 is 2.

In the exemplary embodiment of the present specification, r4 is 3.

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

[Formula 2-1]

In Formula 2-1,

The definitions of R2 to R4 and r2 to r4 are the same as those in Formula 2 above,

G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; nitro group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

g1 and g2 are each an integer from 0 to 5,

When g1 is 2 or more, two or more G1s are the same as or different from each other,

When g2 is 2 or more, two or more G2s are the same as or different from each other.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or unsubstituted C2 to C30 ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted C 3 to C 20 cycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2 to C20 heterocyclic group, or a substituted or unsubstituted C2 to C20 ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; an alkyl group; aryl group; Or a heterocyclic group, or an aromatic hydrocarbon ring bonded to each other with adjacent groups; or an aliphatic hydrocarbon ring.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; an alkyl group; aryl group; or a heterocyclic group, or an aliphatic hydrocarbon ring by combining with an adjacent group.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; t-butyl group; phenyl group; Or a dibenzofuran group, or a cyclohexane ring substituted with a methyl group by combining with an adjacent group.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; t-butyl group; or a phenyl group, or a cyclohexane ring substituted with a methyl group by combining with an adjacent group.

In an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently hydrogen; t-butyl group; or a phenyl group.

In the exemplary embodiment of the present specification, g1 and g2 are each 1.

In one embodiment of the present specification, g1 and g2 are each 2.

In one embodiment of the present specification, g1 and g2 are each 5.

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following compounds.

In the present specification, compounds having various energy band gaps may be synthesized by introducing various substituents into the core structure of the first compound represented by Formula 1 or the second compound represented by Formula 2 above. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the structure as described above.

In the exemplary embodiment of the present specification, the composition including the first compound and the second compound means a mixture of the first compound and the second compound.

In one embodiment of the present specification, the composition refers to a composition in which the first compound and the second compound are physically mixed, or the material in which the first compound and the second compound are physically mixed in a sublimer boat It may refer to a sublimation mixed composition put in a boat and sublimated at high temperature and high pressure.

According to an exemplary embodiment of the present specification, there is provided a deposition source manufactured using the composition. The deposition source includes a composition in which the first compound and the second compound are physically mixed, or a material in which the first compound and the second compound are physically mixed is put in a boat of a sublimer and heated and and a sublimation mixture composition sublimed under high pressure. In the sublimation mixture composition prepared through the sublimator as described above, since the compounds are more uniformly mixed, the lifetime or efficiency of the device is improved when applied to the device.

In an exemplary embodiment of the present specification, the mass ratio of the first compound and the second compound (first compound: second compound) is 1:9 to 9:1.

In an exemplary embodiment of the present specification, the difference between the maximum emission wavelength of the first compound and the maximum emission wavelength (λmax) of the second compound exceeds 15 nm.

In an exemplary embodiment of the present specification, the difference between the maximum emission wavelength of the first compound and the maximum emission wavelength (λmax) of the second compound is 30 nm or less.

In one embodiment of the present specification, the difference between the maximum emission wavelength of the first compound and the maximum emission wavelength (λmax) of the second compound is greater than 15 nm and less than or equal to 30 nm.

In an exemplary embodiment of the present specification, the difference between the maximum emission wavelength of the first compound and the maximum emission wavelength (λmax) of the second compound is greater than 15 nm and less than or equal to 25 nm.

In one embodiment of the present specification, the difference between the maximum emission wavelength of the first compound and the maximum emission wavelength (λmax) of the second compound is 17 nm or more and 23 nm or less.

In an exemplary embodiment of the present specification, the difference between the maximum emission wavelength of the first compound and the maximum emission wavelength (λmax) of the second compound is 19 nm or more and 21 nm or less.

When the difference between the maximum emission wavelength of the first compound and the maximum emission wavelength (λmax) of the second compound satisfies the above range, quantum efficiency or lifetime characteristics are improved.

In an exemplary embodiment of the present specification, the first compound and the second compound satisfy Formula 1 below.

[Equation 1]

| T _sub1 - T _sub2 | < 20 ℃

In the above formula 1,

T _sub1 is the evaporation temperature of the first compound,

T _sub2 is the evaporation temperature of the second compound.

In the present specification, the evaporation temperature means the lowest point of the temperature at which the compound starts to evaporate.

When the first compound and the second compound are mixed in advance to form an organic material layer through a single deposition source, a mixture having excellent uniformity can be obtained by satisfying Equation 1, and a uniform film can be obtained even in the step of manufacturing a device. can be obtained

In an exemplary embodiment of the present specification, the evaporation temperature (T _sub1 ) of the first compound and the evaporation temperature (T _sub2 ) of the second compound are each less than 400 °C.

In an exemplary embodiment of the present specification, the evaporation temperature (T _sub1 ) of the first compound and the evaporation temperature (T _sub2 ) of the second compound are 100 °C or more and less than 400 °C, respectively.

In another exemplary embodiment, the evaporation temperature (T _sub1 ) of the first compound is 100 ℃ or more and less than 400 ℃.

In another exemplary embodiment, the evaporation temperature (T _sub2 ) of the second compound is 100 ℃ or more and less than 400 ℃.

In another exemplary embodiment, the evaporation temperature (T _sub1 ) of the first compound is 150 ℃ or more and less than 400 ℃.

In another exemplary embodiment, the evaporation temperature (T _sub2 ) of the first compound is 150 ℃ or more and less than 400 ℃.

According to an exemplary embodiment of the present invention, when the first compound and the second compound are mixed in advance before deposition, they are simultaneously evaporated by a single deposition source, so that it must be stable during the evaporation process. That is, the composition of the film must be kept constant during the manufacturing process, and for this purpose, the change in composition of the mixed material must be within a certain range. If the composition change is high, the performance of the manufactured device may be adversely affected. Therefore, the difference in the evaporation temperature values of the materials to be mixed should be small. The evaporation temperature is a location of a point at which an evaporation source of a material is evaporated in a high vacuum deposition apparatus having a chamber base pressure ^{of 1 X 10 -6} Torr to 1 X 10 ^{-9 Torr, for example, a predetermined distance from a sublimation crucible in a VTE apparatus.} Measured at a deposition rate of 2 Å/s on a spaced apart surface. Various measured values such as temperature, pressure, deposition rate, etc. disclosed herein are expected to have nominal variations due to expected errors in the measurements that produce such quantitative values, as will be understood by those skilled in the art. do.

In the present specification, the composition includes the first compound represented by Formula 1 and the second compound represented by Formula 2, and the mixture form, mixing ratio, etc. of the compound of Formula 1 and the compound of Formula 2 is not limited

In an exemplary embodiment of the present specification, the first compound and the second compound included in the composition satisfy Formula 2 below.

[Equation 2]

| (C1-C2)/C1 | < 10%

In the above formula 2,

C1 is the initial concentration of the first compound,

C2 is a high vacuum deposition apparatus having a chamber base pressure of 1 X 10 ^-9 Torr to 1 X 10 ^{-4 Torr, and 1 Å/s to} Concentration of the first compound as measured in a film formed by deposition at a deposition rate of 10 Å/s.

The "determined distance" means a distance between an evaporation source in a deposition apparatus and a surface to be deposited, which is determined according to the size of the chamber.

In an exemplary embodiment of the present specification, the first compound and the second compound included in the composition satisfy the following formula 2-1.

[Equation 2-1]

|(C1-C2)/C1| < 7%

In Formula 2-1,

C1 is the initial concentration of the first compound,

C2 is a high vacuum deposition apparatus having a chamber base pressure of 1 X 10 ^-9 Torr to 1 X 10 ^{-4 Torr, and 1 Å/s to} Concentration of the first compound as measured in a film formed by deposition at a deposition rate of 10 Å/s.

In the present specification, the initial concentration means the concentration of the compound in the composition before deposition.

In an exemplary embodiment of the present specification, the concentrations C1 and C2 are relative concentrations of the first compound represented by Formula 1 above. Thus, the conventional requirement for the two compounds forming the compositions described above is that the relative concentration of the first compound in the as-deposited film (C2) is as high as possible with the original relative concentration of the first compound in the evaporation source composition (C1). It means you have to be close. One of ordinary skill in the art will understand that the concentration of each component is expressed as a relative percentage. The concentration of each component in the composition may be measured by a suitable analytical method such as high pressure liquid chromatography (HPLC) and nuclear magnetic resonance spectroscopy (NMR). We used HPLC and calculated the percentage by dividing the integral area under the HPLC trace of each component by the total integral area. HPLC can use different detectors, such as UV-vis, photo diode array detector, refractive index detector, fluorescence detector, and light scattering detector. Due to different material properties, each component in the composition may react differently. Thus, while the measured concentration may differ from its actual concentration in the composition, the value of the relative ratio of (C1-C2)/C1 is, e.g., HPLC where all concentrations are exactly the same for each component, as long as the experimental conditions are calculated to be constant. independent of the above variables, provided that it remains under the parameter. It is sometimes desirable to select the measurement conditions so that the calculated concentration is close to the actual concentration. However, this is not essential. It is important to select detection conditions that accurately detect each component. For example, a fluorescence detector should not be used if one of the components is not fluorescent.

An exemplary embodiment of the present specification provides a deposition source manufactured using the composition.

The organic electroluminescent device according to the present specification includes an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer comprises the above-described composition.

The organic electroluminescent device according to the present specification includes an anode; cathode; and a light emitting layer provided between the anode and the cathode, wherein the light emitting layer comprises the composition described above.

In the organic electroluminescent device according to the present specification, the fact that at least one layer of the organic material layer includes the above-described composition means that the first compound represented by Formula 1 and the second compound represented by Formula 2 are included at the same time. can

The organic electroluminescent device of the present specification may be manufactured by a conventional organic electroluminescent device manufacturing method and material, except for forming an organic material layer using the above-described first and second compounds.

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic electroluminescent device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic electroluminescent device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic electroluminescent device of the present invention is an organic material layer, a hole transport layer, a hole injection layer, an electron blocking layer, a layer that transports and injects holes at the same time, an electron transport layer, an electron injection layer, a hole blocking layer, and electron transport and injection. It may have a structure including one or more layers among the layers to be performed at the same time. However, the structure of the organic electroluminescent device of the present specification is not limited thereto and may include a smaller number or a larger number of organic material layers.

In the organic electroluminescent device of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer is the first compound and the second compounds may be included.

In the organic electroluminescent device of the present specification, the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include the first compound and the second compound described above.

In one embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, an electron injection and transport layer or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron injection and transport layer or the hole blocking layer is the above-mentioned It may include a first compound and a second compound.

In the organic electroluminescent device of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, the electron injection layer, or the electron transport and injection layer is the first compound and A second compound may be included.

In an exemplary embodiment of the present specification, the organic material layer may include an electron control layer, and the electron control layer may include the first compound and the second compound described above.

In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the first compound and the second compound described above.

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the first compound and the second compound as a host.

In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the above-described first compound and the second compound as a dopant.

In an exemplary embodiment of the present specification, the organic electroluminescent device is a green organic electroluminescent device in which the light emitting layer includes the first compound and the second compound as a host.

According to an exemplary embodiment of the present specification, the organic electroluminescent device is a red organic electroluminescent device in which the light emitting layer includes the first compound and the second compound as a host.

In another exemplary embodiment, the organic electroluminescent device is a blue organic electroluminescent device in which the light emitting layer includes the first compound and the second compound as a host.

In the exemplary embodiment of the present specification, the light emitting layer includes the first compound and the second compound as a dopant. In this case, the content of the first compound and the second compound is 3:7 to 7:3 by weight, preferably 4:6 to 6:4, and more preferably 1:1. When the content of the first compound and the second compound satisfy the above range, the efficiency and lifespan characteristics of the organic electroluminescent device are improved.

In one embodiment of the present specification, the light emitting layer further includes a host.

According to an exemplary embodiment of the present specification, the light emitting layer further includes two or more types of hosts.

According to an exemplary embodiment of the present specification, the light emitting layer further includes a fluorescent host.

In the exemplary embodiment of the present specification, the light emitting layer includes the first compound and the second compound as a dopant, and includes an additional host. At this time, the total content of the dopant may be included in an amount of 0.01 parts by weight to 60 parts by weight based on 100 parts by weight of the host, preferably 0.01 parts by weight to 10 parts by weight, more preferably 1 part by weight to 5 parts by weight. may be included. When the content of the host and the dopant satisfy the above range, the efficiency and lifespan characteristics of the organic electroluminescent device are improved.

The additional host includes a compound represented by the following formula (H).

[Formula H]

In the formula (H),

L21 to L23 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar21 to Ar23 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

l21 is an integer of 1 to 3, and when l21 is 2 or more, L21 of 2 or more are the same as or different from each other,

122 is an integer of 1 to 3, and when 122 is 2 or more, L22 of 2 or more are the same as or different from each other,

l23 is an integer of 1 to 3, and when l23 is 2 or more, L23 of 2 or more are the same as or different from each other,

a is 0 or 1.

According to an exemplary embodiment of the present specification, when a is 0, the position of -L23-Ar23 is hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, a is 0.

According to an exemplary embodiment of the present specification, a is 1.

According to an exemplary embodiment of the present specification, Chemical Formula H is represented by the following Chemical Formula H-1 or H-2.

[Formula H-1]

[Formula H-2]

In Formulas H-1 and H-2,

The definitions of L21 to L23, 121 to 123, and Ar21 to Ar23 are the same as defined in Formula H above,

D is deuterium,

n1 is an integer from 0 to 8,

n2 is an integer from 0 to 7.

According to an exemplary embodiment of the present specification, in Formula H, 121 is 1.

According to an exemplary embodiment of the present specification, in Formula H, 122 is 1.

According to an exemplary embodiment of the present specification, in Formula H, 123 is 1.

According to an exemplary embodiment of the present specification, in Formula H, 121 is 2, and two L21s are the same as or different from each other.

According to an exemplary embodiment of the present specification, in Formula H, the 122 is 2, and the two L22s are the same as or different from each other.

According to an exemplary embodiment of the present specification, in Formula H, 123 is 2, and two L23s are the same as or different from each other.

According to an exemplary embodiment of the present specification, R21 to R27 are the same as or different from each other, and each independently hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, R21 to R27 are hydrogen.

According to an exemplary embodiment of the present specification, R21 to R27 are deuterium.

According to an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms that is unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms that is unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; or a divalent dibenzofuran group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms that is unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms that is unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; or a divalent dibenzofuran group unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, L23 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L23 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L23 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L23 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L23 is a direct bond; or a phenylene group.

According to an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms that is unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; biphenyl group; a naphthyl group unsubstituted or substituted with deuterium; phenanthrene group; a dibenzofuran group unsubstituted or substituted with deuterium; dibenzothiophene group; or a benzonaphthofuran group.

According to an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms that is unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; biphenyl group; a naphthyl group unsubstituted or substituted with deuterium; phenanthrene group; a dibenzofuran group unsubstituted or substituted with deuterium; dibenzothiophene group; or a benzonaphthofuran group.

According to an exemplary embodiment of the present specification, Ar23 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar23 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar23 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar23 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar23 is a phenyl group; naphthyl group; or a dibenzofuran group.

According to an exemplary embodiment of the present specification, the deuterated rate of Formula H is 40% or more.

According to an exemplary embodiment of the present specification, the deuterated rate of Formula H is 60% or more.

According to an exemplary embodiment of the present specification, the deuterated rate of Formula H is 40% to 100%.

According to an exemplary embodiment of the present specification, the deuterated rate of Formula H is 60% to 100%.

According to an exemplary embodiment of the present specification, Formula H is any one selected from the following compounds.

In order to form a light emitting layer including the composition, a co-deposition of depositing the first compound and the second compound through different deposition sources may be used, and the first compound and the second compound are mixed in advance (line mixing) and depositing by one deposition source can be used.

According to an exemplary embodiment of the present invention, the light emitting layer may include the first compound and the second compound as a blue fluorescent dopant, and may include an additional host material. In general, three deposition sources are required to manufacture a blue fluorescent light emitting layer having such a mixed dopant material, which makes the process very complicated and expensive. Accordingly, by pre-mixing two or more kinds of materials among three or more kinds of compounds and evaporating them from one deposition source to form an organic layer, it is possible to reduce the complexity of the manufacturing process and achieve stable deposition due to co-evaporation.

The two kinds of dopants (the first compound and the second compound) exhibit stable miscibility, and since the change in composition after mixing is within a certain range, they can be simultaneously deposited from one source. The uniform co-evaporation of the two dopants is important for the sustainability of the performance of the fabricated organic electroluminescent device.

According to an exemplary embodiment of the present specification, the light-emitting layer further includes two or more types of hosts, and in order to form the light-emitting layer, co-deposition of depositing the two or more types of hosts through different deposition sources may be used, A method of pre-mixing (pre-mixing) the two or more types of hosts and depositing them by one deposition source may be used.

According to an exemplary embodiment of the present specification, the light-emitting layer further includes a host, and in order to form the light-emitting layer, the host, the first compound, and the second compound are deposited through different deposition sources using co-deposition. In addition, a method of pre-mixing (pre-mixing) the host, the first compound, and the second compound and depositing by a single deposition source may be used.

According to an exemplary embodiment of the present specification, the organic electroluminescent device is a multi-stack type, and one or two stacks of them include the composition.

According to an exemplary embodiment of the present specification, the emission spectrum of the emission layer including the composition has a maximum emission wavelength (λmax) within 400 nm to 470 nm.

One embodiment of the present specification comprises the steps of preparing a substrate; forming an anode on the substrate; forming one or more organic material layers on the anode; and forming a cathode on the organic material layer, wherein the forming of the one or more organic material layers comprises the step of forming one or more organic material layers using the above-described composition. Method of manufacturing an organic electroluminescent device provides

In an exemplary embodiment of the present specification, the step of forming one or more organic material layers using the composition includes forming one or more organic material layers using the composition using the composition 1 X 10 ^-9 Torr to 1 X 10 ^{in a high vacuum deposition apparatus having a chamber base pressure of −4} Torr, depositing the composition at a deposition rate of 1 Å/s to 10 Å/s on a surface located a predetermined distance from the location of the point at which the composition is evaporated.

In an exemplary embodiment of the present specification, the step of forming one or more organic material layers using the composition includes forming one or more organic material layers using the composition using the composition 1 X 10 ^-9 Torr to 1 X 10 ^In a high vacuum deposition apparatus having a chamber base pressure of -4 Torr, depositing the composition at a deposition rate of 2 Å/s on a surface located a predetermined distance from the location of the point at which the composition is evaporated.

According to an exemplary embodiment of the present specification, the step of forming one or more organic material layers using the composition includes depositing a mixture including the first compound and the second compound through one deposition source.

According to an exemplary embodiment of the present specification, the step of forming one or more organic material layers using the composition includes depositing a mixture including the first compound and the second compound through another deposition source.

An exemplary embodiment of the present specification comprises the steps of manufacturing a deposition source using the composition; preparing a substrate; forming an anode on the substrate; forming one or more organic material layers on the anode; and forming a cathode on the organic material layer, wherein the forming of the one or more organic material layers includes the step of forming one or more organic material layers using the deposition source. Method of manufacturing an organic electroluminescent device provides

In one embodiment of the present specification, the step of forming one or more organic material layers using the deposition source means depositing a mixture including the first compound and the second compound through one deposition source. .

The organic electroluminescent device of the present specification further comprises at least one organic material layer of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. can do.

In an exemplary embodiment of the present specification, the organic electroluminescent device includes an anode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein at least one of the two or more organic material layers includes the first compound and the second compound.

In an exemplary embodiment of the present specification, the two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and an electron blocking layer.

In one embodiment of the present specification, the two or more organic material layers are selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, an electron control layer, and a hole blocking layer. can

In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazolyl group or a benzocarbazolyl group in addition to the organic material layer including the first compound and the second compound. may include more.

In one embodiment of the present specification, the organic electroluminescent device may be an organic electroluminescent device of a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present specification, the organic electroluminescent device may be an organic electroluminescent device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

In the organic electroluminescent device of the present invention, the organic material layer may include an electron blocking layer, the electron blocking layer may be a material known in the art may be used.

The organic electroluminescent device may have, for example, a stacked structure as follows, but is not limited thereto.

(1) anode/hole transport layer/light emitting layer/cathode

(2) anode / hole injection layer / hole transport layer / light emitting layer / cathode

(3) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / cathode

(4) anode / hole transport layer / light emitting layer / electron transport layer / cathode

(5) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

(7) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(8) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

(9) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(10) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(11) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(12) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(13) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(15) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

The structure of the organic electroluminescent device of the present specification may have a structure as shown in FIGS. 1 and 2 , but is not limited thereto.

1 illustrates a structure of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer 6 .

2 is a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a first electron transport layer (7), a second electron transport layer (8), the structure of the organic electroluminescent device in which the electron injection layer 9 and the cathode 10 are sequentially stacked is illustrated. In this structure, the compound is the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the light emitting layer (6), the first electron transport layer (7), the second electron transport layer (8) Alternatively, it may be included in the electron injection layer 9 .

For example, the organic electroluminescent device according to the present specification uses a PVD (physical vapor deposition) method, such as sputtering or e-beam evaporation, to form a metal or a conductive metal oxide on a substrate or a metal oxide or these By depositing an alloy to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. can be manufactured. In addition to this method, an organic electroluminescent device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The at least one organic material layer may be formed by a method known in the art, such as a deposition process or a solvent process. In the deposition process, when the organic material layer includes two or more materials, a method of depositing two or more materials by using a different deposition source is used, or by mixing two or more materials in advance and depositing by one deposition source. Available. Examples of the solvent process include spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method.

The organic material layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer for injecting and transporting electrons at the same time, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc. and may have a single-layer structure. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a vapor deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

The anode is an electrode for injecting holes, and the anode material is usually preferably a material having a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that smoothly injects holes from the anode into the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.

The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of receiving holes from the anode or hole injection layer and transferring them to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The above-described compound or a material known in the art may be used for the electron blocking layer.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include the aforementioned compound of Formula 1; 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the light-emitting layer emits red light, the light-emitting dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a _{fluorescent material such as Alq 3} (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a _{phosphor such as Ir(ppy) 3} (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, the present invention is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant includes a _{phosphorescent material such as (4,6-F2ppy) 2} Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include the above-mentioned compound or Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport properties can be prevented from being deteriorated, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being raised to improve the movement of electrons. There are advantages that can be

The electron injection layer may serve to facilitate electron injection. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and also , a compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

The organic electroluminescent device according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.

Hereinafter, examples will be given to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described below. The embodiments of the present application are provided to more completely explain the present specification to those of ordinary skill in the art.

<Production Example>

Preparation Example 1: Synthesis of Intermediate 1-1.

1,3-dibromo-5-methylbenzene (15 g, 60.0 mmol), bis(4-(tert-butyl)phenyl)amine (33.78 g, 120 mmol), Pd(Pt-Bu ₃ ) ₂ (0.31 g, 0.6 mmol) and NaOt-Bu (11.54 g, 120 mmol) were dissolved in toluene (200 ml) and stirred under reflux. After completion of the reaction, after cooling to room temperature, the reaction product was transferred to a separatory funnel and extracted. It _{was dried over MgSO 4} , filtered, concentrated, and purified by column chromatography to obtain Intermediate 1-1 (29.3 g, yield 75%).

MS: [M+H] ⁺ = 652

Preparation Example 2: Synthesis of Compound 1.

Intermediate 1-1 (29.3 g, 45.0 mmol) is dissolved in DCB (450 ml). Add BI ₃ (26.43 g, 67.5 mmol) and stir at 130°C. After the reaction was completed, N,N-Diisopropylethylamine (DIPEA) (23.27 g, 180.0 mmol) was added at 0 °C. After that, the reaction was transferred to a separatory funnel and extracted. It _{was dried over MgSO 4} , filtered, concentrated, and purified by column chromatography to obtain compound 1 (12.45 g, yield 42%).

MS: [M+H] ⁺ =659

Preparation Example 3: Synthesis of Intermediate 2-1.

Intermediate 2-1 was obtained in the same manner as in Preparation Example 1, except that 1-bromo-3-chloro-5-methylbenzene was used instead of 1,3-dibromo-5-methylbenzene. .

MS:[M+H] ⁺ = 407

Preparation Example 4: Synthesis of Intermediate 2-2.

Intermediate 2-1 instead of bis(4-(tert-butyl)phenyl)amine and 5-(tert-butyl)-N-(4-(tert-butyl)phenyl instead of 1,3-dibromo-5-methylbenzene )-[1,1'-biphenyl]-2-amine was obtained in the same manner as in the preparation method of Intermediate 1-1 of Preparation Example 1, except that Intermediate 2-2 was obtained.

MS:[M+H] ⁺ = 728

Preparation 5: Synthesis of compound 2.

Compound 2 was obtained in the same manner as in the preparation method of Compound 1 of Preparation Example 2, except that Intermediate 2-2 was used instead of Intermediate 1-1.

MS:[M+H] ⁺ = 735

Preparation Example 6: Synthesis of Intermediate 3-1.

Intermediate 2-1 instead of bis(4-(tert-butyl)phenyl)amine and N-(5-(tert-butyl)-[1,1'-biphenyl] instead of 1,3-dibromo-5-methylbenzene -2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine The same method as the preparation method of Intermediate 1-1 of Preparation Example 1, except that to obtain Intermediate 3-1.

Preparation Example 7: Synthesis of compound 3.

Compound 3 was obtained in the same manner as in the preparation method of Compound 1 of Preparation Example 2, except that Intermediate 3-1 was used instead of Intermediate 1-1.

MS:[M+H] ⁺ = 789

Preparation 8: Synthesis of Intermediate 4-1.

Except for using 3-methyl-N-phenylaniline instead of bis(4-(tert-butyl)phenyl)amine and 1-bromo-3-chloro-5-methylbenzene instead of 1,3-dibromo-5-methylbenzene obtained Intermediate 4-1 in the same manner as in the preparation method of Intermediate 1-1 of Preparation Example 1.

MS:[M+H] ⁺ = 308

Preparation Example 9: Synthesis of Intermediate 4-2.

Intermediate 4-1 instead of bis(4-(tert-butyl)phenyl)amine and 5-(tert-butyl)-N-(5,5,8,8- instead of 1,3-dibromo-5-methylbenzene In the same manner as for the preparation of Intermediate 1-1 of Preparation Example 1, Intermediate 4- got 2

MS:[M+H] ⁺ = 663

Preparation 10: Synthesis of compound 4.

Compound 4 was obtained in the same manner as in the preparation method of Compound 1 of Preparation Example 2, except that Intermediate 4-2 was used instead of Intermediate 1-1.

MS:[M+H] ⁺ = 671

Preparation 11: Synthesis of Intermediate 5-1.

Replace bis(4-(tert-butyl)phenyl)amine with 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)benzo[b]thiophen-3-amine, 1,3-dibromo Intermediate 5-1 was obtained in the same manner as in Preparation Example 1 of Intermediate 1-1, except that 1-bromo-3-chloro-5-methylbenzene was used instead of 5-methylbenzene.

MS:[M+H] ⁺ = 463

Preparation 12: Synthesis of Intermediate 5-2.

Intermediate 4-1 instead of bis(4-(tert-butyl)phenyl)amine and N-(5-(tert-butyl)-[1,1'-biphenyl] instead of 1,3-dibromo-5-methylbenzene -2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine The same method as the preparation method of Intermediate 1-1 of Preparation Example 1, except that to obtain Intermediate 5-2.

MS:[M+H] ⁺ = 838

Preparation 13: Synthesis of compound 5.

Compound 5 was obtained in the same manner as in the preparation of Compound 1 of Preparation Example 2, except that Intermediate 5-2 was used instead of Intermediate 1-1.

MS:[M+H] ⁺ = 846

<Example 1-1>

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,400 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing 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, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of the following HI-A and LG-101 to a thickness of 650 Å and 50 Å, respectively, on the ITO transparent electrode prepared as described above. On the hole injection layer, the following HT-A was vacuum-deposited to a thickness of 600 Å to form a hole transport layer. On the hole transport layer, the following HT-B was vacuum deposited to a thickness of 50 Å to form an electron blocking layer. Then, on the electron blocking layer, the host BH-A, the first dopant compound 1, and the second dopant compound 4 (weight ratio 1:1) were simultaneously vacuum deposited to a thickness of 200 Å to form a light emitting layer. As the deposition method, a pre-mixing method in which Compound 1 and Compound 4 were mixed in advance and deposited through a single deposition source was used. At this time, the deposition rate was controlled so that the weight ratio of the host BH-A and the total dopant compound was 96 to 4.

Then, on the light emitting layer, 50 Å of the following compound ET-A was vacuum deposited as a first electron transport layer, followed by vacuum deposition of the following ET-B and LiQ in a 1:1 weight ratio to form a second electron transport layer to a thickness of 360 Å did On the second electron transport layer, LiQ was vacuum-deposited to a thickness of 5 Å to form an electron injection layer. On the electron injection layer, aluminum and silver were deposited to a thickness of 220 Å in a weight ratio of 10:1, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.9 Å/sec, the deposition rate of the aluminum of the cathode was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 Х 10 ^-7 ~ 5 Х 10 ^-8 torr to manufacture an organic light emitting device.

The compound used in Example 1-1 is as follows.

<Examples 1-2 to 1-6>

Examples 1-2 to Examples using the same method as in Example 1-1, except that dopant compounds shown in Table 2 below were used instead of Compound 1 and Compound 4 as dopant materials for the emission layer in Example 1-1. Each of the organic light emitting devices 1-6 was fabricated.

<Example 1-7>

Example 1 except that the dopant compounds listed in Table 2 below were used instead of the dopant compounds for the light emitting layer in Example 1-1, and the light emitting layer was formed by a co-deposition method in which the dopant compounds were deposited by different deposition sources. The organic light-emitting device of Examples 1-7 was manufactured using the same method as in -1.

<Comparative Example 1-1>

An organic light emitting diode of Comparative Example was manufactured in the same manner as in Example, except that only Compound 1 was used as a dopant material for the emission layer in Example 1-1.

<Comparative Examples 1-2 to 1-6>

Organic light emission of Comparative Examples 1-2 to 1-6 using the same method as in Example 1-1, except that the dopant compounds shown in Table 2 below were used as the dopant material for the emission layer in Example 1-1. Each device was fabricated.

The maximum emission wavelength (EL max) values of the compounds 1 to 5 are as shown in Table 1 below.

compound EL max (nm) compound 1 464 compound 2 465 compound 3 464 compound 4 444 compound 5 445

^{Voltage when applying a current density of 10 mA/cm 2} to the organic light-emitting devices of the Examples and Comparative Examples, efficiency, color coordinates, and _{lifetime (T 95} ) when applying a current density of ^{20 mA/cm 2} are measured and , the results are shown in Table 2 below. At this time, T ₉₅ means the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm ^{2 is 100%, based on the result of Comparative Example 1-1 of Compound 1 (} 100%) as a percentage.

first dopant second dopant Voltage
(V) quantum efficiency
(QE) color coordinates
CIEy LT95 (%) Example 1-1 compound 1 compound 4 3.83 7.43 0.096 131 Example 1-2 compound 1 compound 5 3.83 7.31 0.098 115 Examples 1-3 compound 2 compound 4 3.84 7.34 0.101 120 Examples 1-4 compound 2 compound 5 3.81 7.33 0.098 111 Examples 1-5 compound 3 compound 4 3.82 7.24 0.096 115 Examples 1-6 compound 3 compound 5 3.86 7.22 0.099 116 Examples 1-7 compound 1 compound 4 3.83 7.23 0.094 109 Comparative Example 1-1 compound 1 - 3.85 7.21 0.107 100 Comparative Example 1-2 compound 2 - 3.82 7.10 0.100 90 Comparative Example 1-3 compound 3 - 3.84 7.12 0.105 82 Comparative Example 1-4 compound 4 - 3.83 6.42 0.090 91 Comparative Example 1-5 compound 5 - 3.83 6.31 0.092 81 Comparative Example 1-6 compound 1 compound 2 3.83 7.01 0.111 91

As shown in Table 2, the organic light emitting device of the embodiment in which the compound of Formula 1 is used as the second dopant material and the compound of Formula 2 is simultaneously used as the first dopant material, the compound of Formula 1 and the Formula Compared to the organic light emitting device of Comparative Example employing only one kind of compound 2 as the first dopant material and the second dopant material or using only one dopant (first dopant), particularly in terms of quantum efficiency and lifespan, excellent properties are exhibited. it was

Specifically, Examples 1-1 (premixed) and Examples 1-7 (co-mixed) using Compound 1 and Compound 4 together rather than the devices of Comparative Example 1-1 using only Compound 1 and Comparative Example 1-4 using only Compound 4 It can be seen that the quantum efficiency and lifetime characteristics of the device of deposition) are improved. Among them, it can be seen that the quantum efficiency and lifespan characteristics of the device of Example 1-1 in which the compound was deposited by the premixing method were all improved compared to the device of Examples 1-7 in which the compound was deposited by the co-deposition method.

In addition, in the devices of Examples 1-1 to 1-7, the maximum emission wavelength difference between the first dopant material and the second dopant material is about 19 nm to 21 nm, whereas the difference in the maximum emission wavelength in the devices of Comparative Examples 1-6 is about 1 nm. Therefore, when the difference in the maximum emission wavelength of each compound exceeds 15 nm, it can be confirmed that the performance is improved in terms of quantum efficiency and lifetime compared to the case where it is not.

Through this, in the case of a blue organic light emitting device made by using the compound represented by Formula 1 of the present invention and the compound represented by Formula 2 of the present invention together as a dopant, it can be confirmed that quantum efficiency and lifespan characteristics are improved.

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

Claims (15)

A composition comprising a first compound represented by the following formula (1) and a second compound represented by the following formula (2):
[Formula 1]

In Formula 1,
A1 is a substituted or unsubstituted aromatic heterocycle including S; A substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted, condensed ring of an aromatic heterocyclic ring and an aliphatic hydrocarbon ring containing S; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,
A2 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; Or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Condensed ring group of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,
R1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
r1 is an integer from 1 to 3,
When r1 is 2 or more, the 2 or more R1 are the same as or different from each other,
[Formula 2]

In Formula 2,
Y is B; N; P=O; or P=S,
X1 and X2 are the same as or different from each other, and each independently O; S; Se; CR11R12; And selected from the group consisting of NR13,
R2 to R4 and R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; nitro group; halogen group; hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkynyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,
r2 and r3 are each an integer of 1 to 4,
r4 is an integer from 1 to 3,
When r2 to r4 are 2 or more, the substituents in the parentheses are the same as or different from each other. The method according to claim 1,
The difference between the maximum emission wavelength (λmax) of the first compound and the maximum emission wavelength (λmax) of the second compound is greater than 15 nm. The method according to claim 1,
The first compound and the second compound are a composition that satisfies the following formula 1:
[Equation 1]
| T _sub1 - T _sub2 | < 20 ℃
In the above formula 1,
T _sub1 is the evaporation temperature of the first compound,
T _sub2 is the evaporation temperature of the second compound. 4. The method according to claim 3,
The evaporation temperature of the first compound (T _sub1 ) and the evaporation temperature of the second compound (T _sub2 ) are each less than 400 ℃ composition. The composition of claim 1, wherein the first compound and the second compound satisfy the following formula 2:
[Equation 2]
| (C1-C2)/C1 | < 10%
In the above formula 2,
C1 is the initial concentration of the first compound,
C2 is a high vacuum deposition apparatus having a chamber base pressure of 1 X 10 ^-9 Torr to 1 X 10 ^{-4 Torr, wherein C2 is 1 Å/s to} Concentration of the first compound as measured in a film formed by deposition at a deposition rate of 10 Å/s. The method according to claim 1,
The first compound and the second compound are a composition that satisfies the following formula 2-1:
[Equation 2-1]
| (C1-C2)/C1 | < 7%
In Formula 2-1,
C1 is the initial concentration of the first compound,
C2 is a high vacuum deposition apparatus having a chamber base pressure of 1 X 10 ^-9 Torr to 1 X 10 ^{-4 Torr, wherein C2 is 1 Å/s to} Concentration of the first compound as measured in a film formed by deposition at a deposition rate of 10 Å/s. The method according to claim 1,
Wherein A1 is a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; Or a composition that is a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. A deposition source manufactured using the composition of any one of claims 1 to 7. anode; cathode; And an organic electroluminescent device comprising one or more organic material layers provided between the anode and the cathode, wherein at least one of the organic material layers comprises the composition of claim 1. 10. The method of claim 9,
The organic material layer is a light emitting layer, the light emitting layer is an organic electroluminescent device comprising the composition as a dopant. 11. The method of claim 10,
The light emitting layer is an organic electroluminescent device further comprising a host. 11. The method of claim 10,
The organic electroluminescent device is a multi-stack type, wherein one or two stacks of the organic electroluminescent device include the light-emitting layer. 11. The method of claim 10,
The emission spectrum of the emission layer is an organic electroluminescent device having a maximum emission wavelength (λmax) within 400 nm to 470 nm. preparing a substrate;
forming an anode on the substrate;
forming one or more organic material layers on the anode; and
Comprising the step of forming a cathode on the organic material layer,
The method of manufacturing an organic electroluminescent device, wherein the forming of the one or more organic material layers comprises the step of forming one or more organic material layers using the composition of any one of claims 1 to 7. 15. The method of claim 14,
The step of forming one or more organic material layers using the composition is determined from the position of the point at which the composition is evaporated in a high vacuum deposition apparatus having a chamber base pressure of ^{1 X 10 -9} Torr to 1 X 10 ^{-4 Torr.} Method of manufacturing an organic electroluminescent device comprising the step of depositing on a surface located at a distance at a deposition rate of 1 Å / s to 10 Å / s.

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