KR20240146581A - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising the same. The compound of chemical formula 1 is used in an organic light-emitting device, and can lower the driving voltage of the organic light-emitting device, improve the luminous efficiency, and improve the life characteristics of the device due to the thermal stability of the compound.

Description

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME

This application claims the benefit of Korean Patent Application No. 10-2023-0040584 filed with the Korean Intellectual Property Office on March 28, 2023, the entire contents of which are incorporated herein by reference.

The present specification relates to a compound and an organic light-emitting device comprising the same.

In general, the organic luminescence phenomenon refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices utilizing the organic luminescence phenomenon usually have a structure including an anode, a cathode, and an organic layer therebetween. Here, the organic layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

There is a continued need for the development of new materials for organic light-emitting devices such as the above.

Republic of Korea Patent Publication No. 2000-0051826

The present specification provides a compound and an organic light-emitting device comprising the same.

One embodiment of the present specification provides a compound of the following chemical formula 1.

[Chemical Formula 1]

In the above chemical formula 1,

One of R ₁ to R ₁₀ is a moiety bonded to L ₁ , and the rest are the same or different from each other, and each independently represents hydrogen; deuterium; 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 bonds with adjacent groups to form a substituted or unsubstituted ring,

L ₁ is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

Ar ₁ is a substituted or unsubstituted benzoxanthine group; a substituted or unsubstituted benzothioxanthine group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group,

x is 1 or 2,

m is 0 to 3, and when m is 2 or more, two or more L ₁ are equal to or different from each other,

y is 1 or 2, and when y is 2, the two Ar ₁ are equal or different.

In addition, other embodiments of the present specification are:

An anode; a cathode; a first light-emitting layer provided between the anode and the cathode; and a second light-emitting layer provided between the first light-emitting layer and the cathode and in contact with the first light-emitting layer,

The above first light-emitting layer comprises a compound of the above chemical formula 1,

The second light-emitting layer provides an organic light-emitting device including at least one compound of the following chemical formula 2 and chemical formula 3.

[Chemical formula 2]

In the above chemical formula 2,

At least one of R11 to R20 is bonded to the * moiety of the following chemical formula 2-1, and the rest are the same or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group,

[Chemical Formula 2-1]

L2 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

Ar2 is a substituted or unsubstituted aryl group,

p is an integer from 1 to 3,

[Chemical Formula 3]

In the above chemical formula 3,

At least one of Y1 to Y10 is bonded to the * moiety of the following chemical formula 3-1, and the rest are the same or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group,

[Chemical Formula 3-1]

A and B are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted aromatic heterocycle,

L3 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

q is an integer from 1 to 3.

A compound according to one embodiment of the present specification can be used in an organic light-emitting device, thereby lowering the driving voltage of the organic light-emitting device and improving the luminous efficiency. In addition, the life characteristics of the device can be improved due to the thermal stability of the compound.

Figure 1 illustrates an example of an organic light-emitting device according to one embodiment of the present specification.
FIG. 2 illustrates an example of an organic light-emitting device according to one embodiment of the present specification.
FIG. 3 illustrates an example of an organic light-emitting device according to one embodiment of the present specification.
Figure 4 is an MS graph of compound A.
Figure 5 is a diagram showing the results of HPLC analysis of a film deposited using the mixture of Manufacturing Example 3.
Figure 6 is a diagram showing the results of HPLC analysis of a film deposited using the mixture of Manufacturing Example 4.

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

One embodiment of the present specification provides a compound of chemical formula 1.

Chemical formula 1 according to one embodiment of the present specification is a structure in which a specific functional group, Ar ₁ , is bonded to a benzo [ghi] fluoranthene structure through an intermediate linking group, L _{1 ,} and has excellent electron transfer and hole transfer capabilities and high quantum efficiency. Therefore, by applying the compound of Chemical Formula 1 to an organic layer of an organic light-emitting device, the effects of reduced operating voltage, improved efficiency, and longer lifespan can be observed.

Throughout this specification, the term "combination of these" included in the expressions in the Makushi format means a mixture or combination of one or more selected from the group consisting of the components described in the Makushi format, and means including one or more selected from the group consisting of said components.

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

는 연결되는 부위를 의미한다.In this specification,

means the connecting part.

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

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkenyl group; a haloalkyl group; a haloalkoxy group; an arylalkyl group; a silyl group; a boron group; an amine group; an aryl group; a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; and a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

또는

의 치환기가 될 수 있다. 또한, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예컨대, 페닐기, 나프틸기 및 이소프로필기가 연결되어

,

, 또는

의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In this specification, the connection of two or more substituents means that the hydrogen of one substituent is connected to another substituent. For example, the connection of two substituents means that a phenyl group and a naphthyl group are connected.

or

can be a substituent of. In addition, the connection of three substituents includes not only the connection of (substituent 1)-(substituent 2)-(substituent 3) in sequence, but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group are connected.

,

, or

can be a substituent of. The above definition also applies equally to cases where four or more substituents are connected.

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

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 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, These include, but are not limited to, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably one having 3 to 30 carbon atoms, and specifically includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a norbornyl group, and the like.

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

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include, but are not limited to, 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, and styrenyl.

In this specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group among the definitions of the alkyl group.

In this specification, the haloalkoxy group means a group in which at least one halogen group is substituted for hydrogen in the alkoxy group as defined above.

In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the above aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc.

When the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. However, it is preferable that the number of carbon atoms is 10 to 30. Specifically, the polycyclic aryl group may include, but is not limited to, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, etc.

In the present specification, the fluorene group may be substituted, and adjacent groups may be combined with each other to form a ring.

등이 있으나, 이에 한정되지 않는다.When the above fluorene group is substituted or forms a ring,

However, it is not limited to these.

In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent stereostructurally closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

In this specification, an arylalkyl group means that the alkyl group is substituted with an aryl group, and the aryl group and alkyl group of the arylalkyl group may be applied with the examples of the aryl group and alkyl group described above.

In this specification, the aryloxy group means an alkoxy group in which an alkyl group is substituted with an aryl group in the definition of the alkoxy group, and examples of the aryloxy group include, but are not limited to, a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, and a 9-phenanthryloxy group.

In this specification, the alkyl group of the alkylthioxy group is the same as the examples of the alkyl group described above. Specifically, the alkylthioxy group includes, but is not limited to, a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, an octylthioxy group, etc.

In this specification, the aryl group in the arylthioxy group is the same as the examples of the aryl group described above. Specifically, the arylthioxy group includes, but is not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, etc.

In the present specification, a heterocyclic group includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and includes an aromatic heterocyclic group or an aliphatic heterocyclic group. The aromatic heterocyclic group may be represented by a heteroaryl group. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine, phenanthroline, isoxazole group, thiadiazole group, Examples thereof include, but are not limited to, a dibenzofuran group, a dibenzosilole group, a phenoxathiine group, a phenoxazine group, a phenothiazine group, a decahydrobenzocarbazole group, a hexahydrocarbazole group, a dihydrobenzoazacilline group, a dihydroindenocarbazole group, a spirofluorenxanthene group, a spirofluorentioxanthene group, a tetrahydronaphthothiophene group, a tetrahydronaphthofuran group, a tetrahydrobenzothiophene group, and a tetrahydrobenzofuran group.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, etc. The alkyl group among the alkylsilyl groups may be applied with the examples of the above-described alkyl group, the aryl group among the arylsilyl groups may be applied with the examples of the above-described aryl group, the alkyl group and aryl group among the alkylarylsilyl groups may be applied with the examples of the above-described alkyl group and aryl group, and the heteroaryl group among the heteroarylsilyl groups may be applied with the examples of the above-described heterocyclic group.

In the present specification, the boron group may be -BY ₁₀₀ Y ₁₀₁ , wherein Y ₁₀₀ and Y ₁₀₁ are the same or different, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. The boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, and the like.

In the present specification, the amine group can be selected from the group consisting of -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a ditolylamine group, an N-phenyltolylamine group, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group; Examples thereof include, but are not limited to, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, etc.

In this specification, an N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group. The alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and aryl group described above.

In this specification, the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted on N of the amine group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heterocyclic group described above.

In this specification, an N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for N of the amine group. The alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heterocyclic group described above.

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a linear or branched alkyl group. The alkylamine group including two or more alkyl groups may include a linear alkyl group, a branched alkyl group, or a linear alkyl group and a branched alkyl group at the same time. For example, the alkyl group in the alkylamine group may be selected from the examples of the above-mentioned alkyl groups.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heterocyclic group.

In the present specification, the alkyl group among the N-alkylarylamine group, the alkylthioxy group, and the N-alkylheteroarylamine group is the same as the examples of the alkyl group described above. Specifically, the alkylthioxy group includes, but is not limited to, a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, and an octylthioxy group.

In this specification, the aryl group among the aryloxy group, the arylthioxy group, the N-arylalkylamine group, and the N-arylheteroarylamine group is the same as the examples of the aryl group described above. Specifically, examples of the aryloxy group include, but are not limited to, a phenoxy group, a p-toryloxy group, a m-toryloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, and a 9-phenanthryloxy group, and examples of the arylthioxy group include, but are not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, and a 4-tert-butylphenylthioxy group.

In the present specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of a cycloalkyl group, an aryl group, and a combination thereof, and the hydrocarbon ring group may be, but is not limited to, a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a tetrahydronaphthalene group, a tetrahydroanthracene group, a 1,2,3,4-tetrahydro-1,4-methanonaphthalene group, a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group, a spirocyclopentanefluorene group, a spiroadamantanefluorene group, and a spirocyclohexanefluorene group. no.

In the present specification, the meaning of “adjacent” in “forming a ring by bonding with adjacent groups” is the same as described above, and the “ring” means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of a cycloalkyl group, an aryl group, and a combination thereof, except for the non-monovalent ones, and the hydrocarbon ring may be selected from benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2,3,4-tetrahydro-1,4-methanonaphthalene, 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, spirocyclopentanefluorene, spiroadamantanefluorene, and spirocyclohexanefluorene, but is not limited thereto.

In the present specification, a heterocycle includes one or more non-carbon atoms, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and the aromatic heterocycle may be selected from examples of heteroaryl groups among the heterocyclic groups, except that it is not monovalent.

In the present specification, an aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine, thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran.

In the present specification, examples of condensed heterocycles of aliphatic or aromatic and aliphatic include, but are not limited to, tetrahydrobenzonaphthothiophene and tetrahydrobenzonaphthofuran.

In this specification, an arylene group means a group having two bonding positions to an aryl group, i.e., a divalent group. The description of the aryl group described above can be applied to each of these groups, except that they are each divalent.

In this specification, a divalent heterocyclic group means a heterocyclic group having two bonding positions, i.e., a divalent group. The description of the heterocyclic group described above can be applied to each of these, except that they are each divalent.

Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned in this specification are incorporated herein by reference in their entirety, and in case of conflict, this specification, including definitions, will control unless a specific passage is cited. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

Hereinafter, the compound of chemical formula 1 will be described in detail.

According to one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-A.

[Chemical Formula 1-A]

In the above chemical formula 1-A,

The definitions of R ₁ to R ₁₀ , L ₁ , x, m, and y are the same as those defined in the chemical formula 1 above,

X ₁ is O or S,

Any one of R ₁₀₁ to R ₁₁₀ is a moiety bonded to L ₁ , and the rest are the same or different, and each independently represents hydrogen; deuterium; 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 bind to adjacent groups to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-B.

[Chemical Formula 1-B]

In the above chemical formula 1-B,

The definitions of R ₁ to R ₁₀ , L ₁ , x, m, and y are the same as those defined in the chemical formula 1 above,

X ₂ is O, S or NR,

One of R ₂₀₁ to R ₂₁₀ , and R is a moiety bonded to L ₁ , and the rest are the same or different, and each independently represents hydrogen; deuterium; 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 bonds with adjacent groups to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, the chemical formula 1 contains at least one deuterium.

According to one embodiment of the present specification, the meaning of "at least one comprises deuterium" means that at least one of the hydrogens at the substitutable positions is substituted with deuterium or is substituted with a substituent substituted with deuterium. The substituent includes a substituent defined in the "substituted or unsubstituted" above.

According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 0.01% to 100%.

According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 0.1% to 100%.

According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 1% to 100%.

According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 40% to 99%.

According to one embodiment of the present specification, when the chemical formula 1 contains deuterium, the following effects are provided. Specifically, the physicochemical properties, such as the chemical bond length related to deuterium, are different from those of hydrogen, and the elongation amplitude of the C-D bond is smaller than that of the C-H bond, so that the van der Waals radius of deuterium is smaller than that of hydrogen, and in general, the C-D bond can be shown to be shorter and stronger than the C-H bond. Therefore, when hydrogen at a substitutable position in the chemical formula 1 is substituted with deuterium, the energy of the ground state is lowered, and as the bond length of deuterium and carbon becomes shorter, the molecular hardcore volume decreases, and accordingly, the electrical polarizability can be reduced, and the intermolecular interaction can be weakened, thereby increasing the thin film volume. In addition, these characteristics can have the effect of lowering the crystallinity of the thin film, that is, creating an amorphous state, and can be generally effective in increasing the lifespan and operating characteristics of organic light-emitting devices, and heat resistance can be improved compared to conventional organic light-emitting devices.

As used herein, “containing deuterium,” “deuterated,” or “deuterated” means that a hydrogen at a substitutable position of a compound is replaced with deuterium.

As used herein, “perdeuterated” means a compound or group in which all hydrogens in the molecule are replaced with deuterium, and has the same meaning as “100% deuterated.”

In the present specification, "X% deuterated", "degree of deuteration X%", or "deuterium substitution rate X%" means that X% of hydrogens at substitutable positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" of the dibenzofuran, "degree of deuteration 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of 8 hydrogens at substitutable positions of the dibenzofuran are replaced with deuterium.

In this specification, the “degree of deuteration” or “deuterium substitution rate” can be determined by a known method such as nuclear magnetic resonance spectroscopy ( ¹ H NMR), thin-layer chromatography/mass spectrometry (TLC/MS), or gas chromatography/mass spectrometry (GC/MS).

Specifically, when analyzing the "degree of deuteration" or "deuterium substitution rate" by nuclear magnetic resonance spectroscopy ( ^1H NMR), by adding DMF (dimethylformamide) as an internal standard, the degree of deuteration or deuterium substitution rate can be calculated from the total peak integration amount through the integration ratio on ^1H NMR.

In addition, when analyzing the "deuteration degree" or "deuterium substitution rate" through TLC/MS (Thin-Layer Chromatography/Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution of molecular weights at the end of the reaction. For example, when analyzing the deuteration degree of Compound A below, when the molecular weight of the starting material below is 506 and the maximum molecular weight value (median value) of Compound A below is 527 in the MS graph of FIG. 4, since 21 of the hydrogens (26) at substitutable positions of the starting material below were substituted with deuterium, it can be calculated that approximately 81% of the hydrogens were deuterated.

In this specification, D means deuterium.

According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

According to one embodiment of the present specification, the band gap of the compound of chemical formula 1 is 2.9 eV or more.

According to one embodiment of the present specification, the band gap of the compound of chemical formula 1 is 2.9 eV to 4.0 eV.

Specifically, the organic compound used in the organic light-emitting device must have a band gap of 0.5 eV to 4.0 eV to function as an organic semiconductor, and a band gap energy of at least 2.9 eV or more is required to exhibit blue light. According to the principle of fluorescence blue emission of the host-dopant system, the band gap of the blue fluorescent host must be larger than the band gap of the blue fluorescent dopant so that energy transfer occurs smoothly. Therefore, it is preferable that the blue fluorescent host have an energy band gap of 2.9 eV to 4.0 eV.

In this specification, "energy level" means energy size. Therefore, the energy level is interpreted as meaning the absolute value of the corresponding energy value. For example, a low or deep energy level means that the absolute value increases in the minus direction from the vacuum level.

In this specification, HOMO (highest occupied molecular orbital) means a molecular orbital (highest occupied molecular orbital) in which electrons are in the highest energy region in which they can participate in bonding, LUMO (lowest unoccupied molecular orbital) means a molecular orbital (lowest unoccupied molecular orbital) in which electrons are in the lowest energy region among antibonding regions, and HOMO energy level means the distance from a vacuum level to HOMO. In addition, LUMO energy level means the distance from a vacuum level to LUMO.

In this specification, the HOMO energy level can be measured using an atmospheric photoelectron spectrometer (manufactured by RIKEN KEIKI Co., Ltd.: AC3), and the LUMO energy level can be calculated using a wavelength value measured through photoluminescence (PL).

In this specification, band gap means the difference between the HOMO energy level and the LUMO energy level.

The present specification provides an organic light-emitting device comprising the compound described above.

When it is said in this specification that an element is located "on" another element, this includes not only cases where an element is in contact with another element, but also cases where another element exists between the two elements.

When it is said in this specification that a part "includes" a certain component, this does not exclude other components, but rather may include other components, unless otherwise specifically stated.

In this specification, the 'layer' is a term interchangeable with 'film', which is mainly used in the present technical field, and means a coating covering a target area. The size of the 'layer' is not limited, and each 'layer' may have the same or different sizes. According to one embodiment, the size of the 'layer' may be the same as the entire element, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.

In this specification, the meaning that a specific A material is included in a B layer includes both i) one or more A materials being included in one B layer, and ii) the B layer being composed of one or more layers, and the A material being included in one or more of the multiple B layers.

In this specification, the meaning that a specific A material is included in a C layer or a D layer means that i) it is included in at least one layer among at least one C layer, ii) it is included in at least one layer among at least one D layer, or iii) it is included in at least one C layer and at least one D layer, respectively.

As used herein, the "evaporation temperature" of a material is measured within a sublimation crucible of a vacuum deposition tool, e.g., a VTE chamber, at a deposition rate of 2 Å/sec, on a surface spaced a set distance from an evaporation source of the material being evaporated, under a constant pressure of 1 x 10 ^-6 Torr to 1 x 10 ^-9 Torr. It is expected that the various measurements described herein (e.g., temperature, pressure, deposition rate, etc.) will have nominal variations due to expected tolerances in measurements that yield quantitative values, as will be appreciated by those skilled in the art.

One embodiment of the present specification provides an organic light-emitting device including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound of the chemical formula 1.

The organic layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may be formed as a multilayer structure in which two or more organic layers are laminated. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host of the light-emitting layer.

According to one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant includes a fluorescent dopant.

According to one embodiment of the present specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.

According to one embodiment of the present specification, the non-pyrene compound includes a boron compound.

According to one embodiment of the present specification, the light-emitting layer further includes at least one host different from the compound of chemical formula 1.

Any host different from the compound of the above chemical formula 1 may be used without limitation as long as it is an anthracene host used in the art, as long as it is different from the above chemical formula 1, and is not limited thereto.

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant.

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the host includes a compound represented by the chemical formula 1.

According to one embodiment of the present specification, the dopant is a blue dopant.

According to one embodiment of the present specification, the organic light-emitting device is a blue organic light-emitting device.

According to one embodiment of the present specification, the light-emitting layer includes two or more mixed hosts, and at least one of the two or more mixed hosts includes a compound represented by the chemical formula 1.

According to one embodiment of the present specification, the light-emitting layer comprises two or more mixed hosts, at least one of the two or more mixed hosts comprises a compound represented by the chemical formula 1, and the remainder comprises anthracene compounds different from the chemical formula 1.

Among the above two or more mixed hosts, at least one of which includes a compound represented by the above chemical formula 1, and the rest are different from the above chemical formula 1, and any anthracene host used in the art may be used without limitation, but is not limited thereto.

An organic light-emitting device using two or more mixed hosts according to one embodiment of the present specification is intended to improve the performance of the device by mixing the advantages of each host. For example, when two hosts are mixed, an organic light-emitting device having the effects of high efficiency, low voltage, and long life can be manufactured by mixing one host having the effects of high efficiency and low voltage and one host having the effects of long life.

According to one embodiment of the present specification, the light-emitting layer has two or more layers, and at least one layer among the two or more light-emitting layers includes the compound of the chemical formula 1.

According to one embodiment of the present specification, the light-emitting layer has two or more layers, at least one layer of the two or more light-emitting layers includes two or more kinds of mixed hosts, and at least one of the two or more kinds of mixed hosts includes the compound of the chemical formula 1.

According to one embodiment of the present specification, the light-emitting layer is two-layered, and one of the two light-emitting layers includes the compound of chemical formula 1.

According to one embodiment of the present specification, the light-emitting layer is two-layered, and one of the two light-emitting layers includes two or more kinds of mixed hosts, and at least one of the two or more kinds of mixed hosts includes a compound of the chemical formula 1.

The above two or more mixed hosts are the same as described above.

According to one embodiment of the present specification, the organic light-emitting device has a maximum emission wavelength (λ _max ) of an emission spectrum of 400 nm to 470 nm.

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant is a fluorescent dopant.

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.

The above pyrene-based compounds and non-pyrene-based compounds can be used without limitation as long as they are compounds used in the art, and are not limited thereto.

According to one embodiment of the present specification, the non-pyrene compound includes a boron compound.

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes a compound represented by the chemical formula 1, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the light-emitting layer includes the host:dopant in a weight ratio of 0.1:99.9 to 20:80.

According to another embodiment of the present specification, the invention further includes a capping layer provided on an opposite surface of at least one of the first electrode and the second electrode, the surface facing the organic layer.

The above capping layer is formed to prevent a significant amount of light from being lost through total reflection in the organic light-emitting element, and the capping layer has the performance to sufficiently protect the lower cathode and light-emitting layer from external moisture penetration or contamination, and has a high refractive index to prevent light loss due to total reflection.

According to another embodiment of the present specification, the capping layer may be provided on each of a surface opposite to a surface of the first electrode facing the organic layer and a surface opposite to a surface of the second electrode facing the organic layer.

According to another embodiment of the present specification, the capping layer may be provided on an opposite surface of the surface of the first electrode facing the organic layer.

According to another embodiment of the present specification, the capping layer may be provided on each of the opposite surfaces of the surface of the second electrode facing the organic layer.

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

According to one embodiment of the present specification, the organic light-emitting element includes a first electrode; a second electrode provided opposite the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

According to one embodiment of the present specification, two or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, may include at least two selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

According to one embodiment of the present specification, two or more hole transport layers are included between the light-emitting layer and the first electrode. The two or more hole transport layers may include materials that are the same or different from each other.

According to one embodiment of the present specification, the first electrode is an anode or a cathode.

According to one embodiment of the present specification, the second electrode is a cathode or an anode.

According to one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate.

According to one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate.

For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 and 2. The above FIGS. 1 and 2 illustrate an organic light-emitting device and are not limited thereto.

Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), a light-emitting layer (4), and a second electrode (3) are sequentially laminated on a substrate (1). The compound is included in the light-emitting layer.

FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a hole transport layer (6), a hole control layer (7), an emission layer (4), an electron control layer (8), an electron transport layer (9), an electron injection layer (10), a second electrode (3), and a capping layer (11) are sequentially laminated on a substrate (1). The compound is included in the emission layer.

The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that the light-emitting layer includes the compound, i.e., the compound of the chemical formula 1.

When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode, and an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, the organic light-emitting device can be manufactured by sequentially depositing a second electrode material, an organic layer, and a first electrode material on the substrate.

In addition, the compound represented by the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

In addition to this method, an organic light-emitting element can also be manufactured by sequentially depositing an organic layer, a first electrode material, and a second electrode material on a substrate. However, the manufacturing method is not limited thereto.

As the first electrode material, a material having a high work function is usually preferable so that hole injection into the organic layer can be smooth. For example, the present invention includes, but is not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ : Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

As the second electrode material, it is preferable to have a low work function so as to facilitate electron injection into the organic layer. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structures such as LiF/Al or LiO ₂ /Al.

The above-described light-emitting layer may include a host material and a dopant material. In addition to the light-emitting layer including the compound of the chemical formula 1 according to one embodiment of the present specification, when an additional light-emitting layer is included, the host material may be a condensed and/or non-condensed aromatic ring derivative or a heterocycle-containing compound. Specifically, the condensed aromatic ring derivatives may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocycle-containing compounds may include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like.

The above dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the present invention includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

According to one embodiment of the present specification, the dopant material includes, but is not limited to, a compound of the following chemical formula D-1 or D-2.

[Chemical Formula D-1]

In the above chemical formula D-1,

L101 and L102 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

Ar101 to Ar104 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[Chemical Formula D-2]

In the above chemical formula D-2,

T1 to T5 are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group,

t3 and t4 are integers from 1 to 4, respectively.

t5 is an integer from 1 to 3,

If the above t3 is 2 or more, the above 2 or more T3 are the same or different from each other,

If the above t4 is 2 or more, the above 2 or more T4 are equal to or different from each other,

When the above t5 is 2 or more, the two or more T5 are equal to or different from each other.

According to one embodiment of the present specification, L101 and L102 are direct bonds.

According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are 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 one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a phenyl group substituted with a methyl group; or a dibenzofuran group.

According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and each independently represents hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are each independently hydrogen; a methyl group; a tert-butyl group; a diphenylamine group; or a phenyl group substituted or unsubstituted with a methyl group or a tert-butyl group.

According to one embodiment of the present specification, the chemical formula D-2 is represented by the following compound.

The above hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes, so that it has a hole receiving effect from the anode and an excellent hole injection effect into the light-emitting layer or the light-emitting material. In addition, it is preferable that it is a material that has an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material. In addition, it is preferable that it is a material that has an excellent thin film forming ability. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include organic compounds of the metal porphyrin, oligothiophene, and arylamine series; organic compounds of the hexanitrilehexaazatriphenylene series; organic compounds of the quinacridone series; organic compounds of the perylene series; Examples include, but are not limited to, conductive polymers of the polythiophene series, such as anthraquinone and polyaniline.

According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound of the following chemical formula HI-1.

[chemical formula HI-1]

In the above chemical formula HI-1,

At least one of X'1 to X'6 is N, and the rest are CH,

R309 to R314 are the same or different, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, X'1 to X'6 are N.

According to one embodiment of the present specification, R309 to R314 are cyano groups.

According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

The above hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. As the hole transport material, a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer and has high hole mobility is preferable. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

The above-mentioned hole control layer is a layer that can improve the lifespan and efficiency of the device by controlling the holes transported from the hole transport layer to be smoothly injected into the light-emitting layer and preventing the electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer. Known materials can be used without limitation, and can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

According to one embodiment of the present specification, the hole transport layer or hole control layer includes, but is not limited to, a compound of the following chemical formula HT-1.

[chemical formula HT-1]

In the above chemical formula HT-1,

R315 to R317 are the same as or different from each other, and each independently represents one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof, or combine with an adjacent group to form a substituted or unsubstituted ring,

r315 is an integer from 1 to 5, and when r315 is 2 or more, two or more R315 are equal to or different from each other,

r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.

According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or combine with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a phenyl group or a phenanthrene group, or combine with an adjacent group to form an indene substituted with a methyl group.

According to one embodiment of the present specification, the chemical formula HT-1 is represented by any one of the following compounds.

The above electron control layer is a layer that controls the smooth injection of electrons transferred from the electron transport layer into the light-emitting layer, and any known material can be used without limitation.

According to one embodiment of the present specification, the electronic control layer includes, but is not limited to, a compound of the following chemical formula EG-1.

[Chemical formula EG-1]

In the above chemical formula EG-1,

At least one of G'1 to G'18 is -L5-Ar5 and the others are hydrogen, or G'1 and G'18 are connected by -L51- to form a substituted or unsubstituted ring,

L5 is a direct bond; or a substituted or unsubstituted arylene group,

Ar5 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

L51 is O; or S.

According to one embodiment of the present specification, the L51 is O.

According to one embodiment of the present specification, the L51 is S.

According to one embodiment of the present specification, G'1 and G'18 are linked by -L51- to form a substituted or unsubstituted heterocycle.

According to one embodiment of the present specification, G'1 and G'18 are linked by -L51- to form a substituted or unsubstituted xanthene ring; or a substituted or unsubstituted thioxanthene ring.

According to one embodiment of the present specification, G'1 and G'18 are linked by -O- to form a substituted or unsubstituted xanthene ring.

According to one embodiment of the present specification, G'1 and G'18 are linked by -S- to form a substituted or unsubstituted thioxanthene ring.

According to one embodiment of the present specification, G'1 and G'18 are linked with -O- to form a xanthene ring.

According to one embodiment of the present specification, G'1 and G'18 are linked with -S- to form a thioxanthene ring.

According to one embodiment of the present specification, L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, L5 is a direct bond; or a phenylene group.

According to one embodiment of the present specification, Ar5 is a substituted or unsubstituted triazine group.

According to one embodiment of the present specification, Ar5 is a triazine group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, Ar5 is a triazine group substituted with a phenyl group.

According to one embodiment of the present specification, the EG-1 is represented by the following compound.

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

According to one embodiment of the present specification, the electron transport layer includes, but is not limited to, a compound represented by the following chemical formula ET-1.

[chemical formula ET-1]

In the above chemical formula ET-1,

At least one of Z11 to Z13 is N, and the others are CH,

L601 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

Ar601 and Ar602 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

l601 is an integer from 1 to 5, and when l601 is 2 or more, 2 or more L601 are equal to or different from each other.

According to one embodiment of the present specification, the L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, the L601 is a phenylene group; a biphenylylene group; or a naphthylene group.

According to one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

The above electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injecting material has excellent electron transport ability, an electron receiving effect from the second electrode, and an excellent electron injection effect for the light-emitting layer or light-emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferable. Specifically, the material includes, but is not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

The above metal complex compounds 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-cresolato)gallium, Examples include, but are not limited to, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc.

The above electron blocking layer is a layer that can improve the life and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the emitting layer and entering the hole injection layer. Known materials can be used without limitation, and can be formed between the emitting layer and the hole injection layer, between the emitting layer and the hole transport layer, or between the emitting layer and a layer that simultaneously injects and transports holes.

The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

The above capping layer is formed to prevent a significant amount of light from being lost through total reflection in the organic light-emitting element, and the capping layer has the performance to sufficiently protect the lower cathode and light-emitting layer from external moisture penetration or contamination, has a high refractive index, can prevent light loss due to total reflection, and can use conventional materials without limitation.

According to one embodiment of the present specification, the capping layer includes, but is not limited to, a compound represented by the following chemical formula CP-1.

[Chemical formula CP-1]

In the above chemical formula CP-1,

L501 and L502 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

R501 and Ar501 to Ar504 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, L501 and L502 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, L501 and L502 are phenylene groups.

According to one embodiment of the present specification, R501 and Ar501 to Ar504 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or combines with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

According to one embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups, or are bonded to adjacent groups to form carbazole substituted or unsubstituted with a phenyl group.

According to one embodiment of the present specification, Ar501 combines with L501 to form a carbazole substituted with a phenyl group.

According to one embodiment of the present specification, Ar503 combines with L503 to form a carbazole substituted with a phenyl group.

According to one embodiment of the present specification, the chemical formula CP-1 is represented by the following compound.

One embodiment of the present invention provides an organic light-emitting device comprising: an anode; a cathode; a first light-emitting layer provided between the anode and the cathode; and a second light-emitting layer provided between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer includes a compound of the chemical formula 1, and the second light-emitting layer includes at least one compound among the compounds of the chemical formula 2 and the compounds of the chemical formula 3.

[Chemical formula 2]

In the above chemical formula 2,

At least one of R11 to R20 is bonded to the * moiety of the following chemical formula 2-1, and the rest are the same or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group,

[Chemical Formula 2-1]

L2 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

Ar2 is a substituted or unsubstituted aryl group,

p is an integer from 1 to 3,

[Chemical Formula 3]

In the above chemical formula 3,

At least one of Y1 to Y10 is bonded to the * moiety of the following chemical formula 3-1, and the rest are the same or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group,

[Chemical Formula 3-1]

A and B are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted aromatic heterocycle,

L3 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

q is an integer from 1 to 3.

In one embodiment of the present specification, the first light-emitting layer and the second light-emitting layer may be provided in contact with each other.

FIG. 3 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a hole transport layer (6), a hole control layer (7), a first light-emitting layer (4-1), a second light-emitting layer (4-2), an electron control layer (8), an electron transport layer (9), an electron injection layer (10), a second electrode (3), and a capping layer (11) are sequentially laminated on a substrate (1).

In one embodiment of the present specification, the first light-emitting layer may include the compound as a host for the first light-emitting layer, and the second light-emitting layer may include at least one compound among the compound of Chemical Formula 2 and the compound of Chemical Formula 3 as a host for the second light-emitting layer. At this time, the first light-emitting layer and the second light-emitting layer may each additionally include a dopant, and the dopant may include a fluorescent dopant. The description of the dopant described above may be applied equally to the dopant included in the first light-emitting layer and the second light-emitting layer.

In one embodiment of the present specification, the second light-emitting layer may include a compound of chemical formula 2 or a compound of chemical formula 3, and the second light-emitting layer may include a compound of chemical formula 2 and a compound of chemical formula 3.

According to one embodiment of the present specification, the deuterium substitution rates of the chemical formulae 2 and 3 are each 0.1% to 100%.

According to one embodiment of the present specification, the deuterium substitution rates of the chemical formulae 2 and 3 are each 1% to 100%.

According to one embodiment of the present specification, the deuterium substitution rates of the chemical formulae 2 and 3 are 40% to 99%, respectively.

According to one embodiment of the present specification, when the chemical formula 2 or 3 contains deuterium, the following effects are provided. Specifically, the physicochemical properties such as the chemical bond length related to deuterium are different from those of hydrogen, and the elongation amplitude of the C-D bond is smaller than that of the C-H bond, so that the van der Waals radius of deuterium is smaller than that of hydrogen, and in general, the C-D bond can be shown to be shorter and stronger than the C-H bond. Therefore, when hydrogen at a substitutable position in the chemical formula 1 is substituted with deuterium, the energy of the ground state is lowered, and as the bond length of deuterium and carbon becomes shorter, the molecular hardcore volume decreases, and accordingly, the electrical polarizability can be reduced, and the intermolecular interaction can be weakened, thereby increasing the thin film volume. In addition, these characteristics can have the effect of lowering the crystallinity of the thin film, that is, creating an amorphous state, and can be generally effective in increasing the lifespan and operating characteristics of organic light-emitting devices, and heat resistance can be improved compared to conventional organic light-emitting devices.

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

The present inventors have found suitable conditions applicable to a benzo[ghi]fluoranthene type host (hereinafter, a compound of chemical formula 1) and an anthracene type host (hereinafter, a compound of chemical formula 2 or 3) which are useful as blue fluorescent host materials and at the same time can provide a stable co-evaporation mixture after premixing.

The emitting layer of an organic light emitting device showing excellent lifetime and efficiency requires more than two components (e.g., three or four components). For this purpose, three or four raw materials are required to manufacture such an emitting layer, which is very complex and expensive compared to a standard two-component emitting layer having a single host and dopant that requires only two raw materials. Premixing two or more materials and evaporating them from a single raw material can reduce the complexity of the manufacturing process. A selected hole transporting host and another type of host, e.g., an electron transporting host, can be mixed and co-evaporated from a single crucible to achieve stable evaporation.

However, the co-evaporation must be stable, i.e. the composition of the evaporated film must remain constant during the fabrication process. Any compositional changes can adversely affect the device performance. In order to obtain a stable co-evaporation from a mixture of compounds under vacuum, it can be assumed that the substances must have the same vaporization temperature under the same conditions. However, this may not be the only parameter to consider. When two compounds are mixed together, they can interact with each other and their vaporization properties can differ from their individual properties. On the other hand, substances with slightly different vaporization temperatures can form a stable co-evaporation mixture. Therefore, it is extremely difficult to achieve a stable co-evaporation mixture. To date, there are tens of thousands of possible host materials in the literature, but examples of stable co-evaporation mixtures are very few. The "evaporation temperature" of a material is measured in a vacuum deposition tool, e.g., a sublimation crucible of a VTE tool, under a constant pressure of 1 x 10 ^-6 Torr to 1 x 10 ^-9 Torr, at a deposition rate of 2 Å/sec, on a surface located a set distance from the evaporation source of the material being evaporated. It is expected that the various measurements disclosed herein, such as temperature, pressure, deposition rate, and the like, will have nominal variations due to expected tolerances in the measurements that yield such quantitative values, as will be understood by those skilled in the art.

The present disclosure describes a novel class of two different types of anthracene hosts (formulas 2 and 3) that can be premixed to provide a stable co-evaporating mixture useful as a blue fluorescent host material. A number of factors other than temperature can contribute to evaporation, such as miscibility of the different materials, different phase transitions. The inventors have discovered that when two materials have similar evaporation temperatures, and similar mass loss rates or similar vapor pressures, the two materials can co-evaporate continuously. The mass loss rate is defined as the percentage of mass loss over time (minutes) and is determined by measuring the time it takes for the composition to reach a steady state evaporation state, as measured by thermogravimetric analysis (TGA) under the same experimental conditions at the same given constant temperature for each compound, after which the composition reaches a steady state evaporation state. The given constant temperature is a temperature point selected such that the mass loss rate value is between about 0.05%/minute and 0.50%/minute. Those skilled in the art will appreciate that the experimental conditions must be constant in order to compare the two parameters. Methods for measuring mass loss rate and vapor pressure are well known in the art and can be found, for example, in the literature (Bull. et al. Mater. Sci. 2011, 34, 7).

In the current state of the art, a prior art document of the present invention, a two-component mixture of a blue fluorescent host, is disclosed in the presented JP 6328890 B2. In order to produce a blue fluorescent emitting layer with such a mixed host material, three evaporation sources are required: two hosts and a blue fluorescent dopant. The concentrations of the cohost and the dopant are important for the device performance, and typically, the deposition rate of each component is measured individually during the deposition. This complicates the manufacturing process and is costly. Therefore, it is desirable to reduce the number of raw materials by mixing two or more components.

This means that two blue fluorescent hosts can be codeposited from a single source when their compositional differences are within a certain range during the premixing and fabrication of the mixture through thermal sublimation. Uniform co-evaporation of the two hosts is important for the sustainability of the performance of devices fabricated from this mixture.

Below, the compound represented by chemical formula 2 is described in detail.

According to one embodiment of the present specification, 1 to 3 of R11 to R20 are bonded to the * moiety of the chemical formula 2-1, and the remainder are hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

According to another embodiment, 1 to 3 of R11 to R20 are bonded to the * moiety of the chemical formula 2-1, and the remainder are hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted silyl group.

In another embodiment, R19 and R20 are bonded to the * moiety of the chemical formula 2-1, and the remainder is hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

According to another embodiment, R19, R20 and R18 are bonded to the * moiety of the chemical formula 2-1, and the remainder is hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

In another embodiment, R19, R20 and R17 are bonded to the * moiety of the chemical formula 2-1, and the remainder is hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

According to one embodiment of the present specification, the substituents among R11 to R20 that are not bonded to the chemical formula 2-1 are the same as or different from each other, and are each independently hydrogen, deuterium or dibenzofuranyl groups.

According to one embodiment of the present specification, p is an integer of 3, and three L2s are equal to or different from each other.

In another embodiment, p is an integer of 2, and two L2 are equal to or different from each other.

According to one embodiment of the present specification, L2 is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

In another embodiment, L2 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

According to another embodiment, the L2 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthreneylene group; or a substituted or unsubstituted triphenylenylene group.

In another embodiment, L2 is a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a phenanthrenylene group substituted or unsubstituted with deuterium; or a triphenylenylene group substituted or unsubstituted with deuterium.

According to one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Ar2 may be substituted with deuterium.

In another embodiment, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, Ar2 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted triphenylenyl group.

In another embodiment, Ar2 is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; or a triphenylenyl group substituted or unsubstituted with deuterium.

The compound of the above chemical formula 2 can utilize compounds described in JP 4070676 B2, KR 1477844 B1, US 6465115 B2, JP 3148176 B2, JP 4025136 B2, JP 4188082 B2, JP 5015459 B2, KR 1979037 B1, KR 1550351 B1, KR 1503766 B1, KR 0826364 B1, KR 0749631 B1, KR 1115255 B1, KR 1538534 B1, etc.

Below, the compound represented by chemical formula 3 is described in detail.

According to one embodiment of the present specification, at least one of Y1 to Y10 is bonded to the * moiety of the chemical formula 3-1, and the remainder is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to one embodiment of the present specification, one to three of Y1 to Y10 are bonded to the * moiety of the chemical formula 3-1, and the remainder are hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

In one embodiment of the present specification, 1 to 3 of Y1 to Y10 are bonded to the * moiety of the chemical formula 3-1, and the remainder are hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted silyl group.

In another embodiment, Y7, Y8 or Y9 is bonded to the * moiety of the chemical formula 3-1, and the remainder is hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

According to another embodiment, the Y7 and Y9 are bonded to the * moiety of the chemical formula 3-1, and the remainder is hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

According to another embodiment, the Y9 and Y10 are bonded to the * moiety of the chemical formula 3-1, and the remainder is hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group.

According to one embodiment of the present specification, among Y1 to Y10, the substituents not bonded to the chemical formula 3-1 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Among Y1 to Y10, the substituents not bonded to the chemical formula 2-1 may be substituted with deuterium.

According to another embodiment, among Y1 to Y10, the substituents which are not bonded to the chemical formula 3-1 are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted triphenylenyl group, and the substituents may be further substituted with deuterium; a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; or a triphenylenyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, q is an integer from 1 to 3, and when q is 2 or more, 2 or more L3s are the same as or different from each other.

According to one embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

In another embodiment, L3 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

According to another embodiment, the L3 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; or a substituted or unsubstituted triphenylenylene group.

In another embodiment, L3 is a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a phenanthrenylene group substituted or unsubstituted with deuterium; or a triphenylenylene group substituted or unsubstituted with deuterium.

According to one embodiment of the present specification, A and B are the same as or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.

In one embodiment of the present specification, A and B are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and aryl groups substituted or unsubstituted with deuterium; or an aromatic heterocycle having 2 to 60 carbon atoms, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and aryl groups substituted or unsubstituted with deuterium.

According to another embodiment, A and B are the same as or different from each other, and each independently represent an aromatic hydrocarbon ring having 6 to 60 carbon atoms, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted with deuterium; or an aromatic heterocycle having 2 to 60 carbon atoms, unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted with deuterium.

In another embodiment, A and B are the same as or different from each other, and are each independently a substituted or unsubstituted benzene; a substituted or unsubstituted naphthalene; a substituted or unsubstituted phenanthrene; a substituted or unsubstituted triphenylene; or a substituted or unsubstituted dibenzofuran.

According to another embodiment, A and B are the same as or different from each other, and are each independently benzene substituted or unsubstituted with at least one substituent selected from the group consisting of deuterium and an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; naphthalene substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium; phenanthrene substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium; triphenylene substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium; or dibenzofuran substituted or unsubstituted with at least one substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium and deuterium.

The compound of the above chemical formula 3 can utilize compounds described in KR 1964435 B1, KR 1899728 B1, KR 1975945 B1, KR 2018-0098122 A, KR 2018-0102937 A, KR 2018-0103352 A, KR 1538534 B1, etc.

The organic light-emitting device according to the present specification can be included and used in various electronic devices. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

Hereinafter, in order to specifically explain the present application, examples will be given and described in detail. However, the examples according to the present application may be modified in various different forms, and the scope of the present application is not construed as being limited to the examples described below. The examples of the present application are provided to more completely explain the present application to a person having average knowledge in the art.

<Manufacturing Example 1> Synthesis of Chemical Formula 1

Synthesis of chemical formulas A1 and B1

After adding SM1 (1 eq) and SM2 ((1.1 eq) to tetrahydrofuran (excess), 2 M potassium carbonate aqueous solution (30 volume ratio with respect to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, and the mixture was heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed, the layers were separated, and column chromatography was performed with hexane and ethyl acetate to prepare the chemical formulas A1 and B1.

Except for changing SM1 and SM2 as shown in Table 1 below in the synthesis method of the chemical formulas A1 and B1 above, A1-1 to A1-3 and B1-1 to B1-3 in Table 1 below were synthesized in the same manner.

[Table 1]

Synthesis of chemical formulas A2 and B2

After dissolving SM1 (either A1 or B1, 1 eq) in dichloromethane (DCM), triethylamine (1.2 eq) was added dropwise and stirred for 1 hour. Then, trifluoroacetic acid (1.1 eq) was slowly added and stirred for 3 hours. After confirming the completion of the reaction, water was extracted and the mixture was subjected to column chromatography with hexane and ethyl acetate to produce the chemical formulas A2 and B2.

Except for changing SM1 and SM2 as shown in Table 2 below in the synthesis method of the chemical formulas A2 and B2 above, A2-1 to A2-3 and B2-1 to B2-3 in Table 2 below were synthesized in the same manner.

[Table 2]

Synthesis of chemical formulas A3 and B3

SM 1 (one of A2 and B2, 1 eq), trimethylsilylacetylene (5 eq), tetrakistriphenyl-phosphinopalladium (0.1 eq), copper iodide (CuI, 1 eq) and triethylamine (excess) were added and heated and stirred at 95°C for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, passed through a filter filled with Celite/silica gel, washed with chloroform, removed the solvent, and subjected to column chromatography with hexane and ethyl acetate to produce the above chemical formulas A3 and B3.

Except for changing SM1 and SM2 as shown in Table 3 below in the synthesis method of the chemical formulas A3 and B3 above, A3-1 to A3-3 and B3-1 to B3-3 in Table 3 below were synthesized in the same manner.

[Table 3]

Synthesis of chemical formulas A4 and B4

SM1 (one of A3 and B3, 1 eq), platinum chloride (0.05 eq) and toluene (excess) were added, stirred at 95°C for 3 hours, and cooled to room temperature after confirming the completion of the reaction. After filtration through a Celite/silica gel pad, the solvent was removed by distillation under reduced pressure, and then column chromatography was performed with hexane and ethyl acetate to prepare the above chemical formulas A4 and B4.

Except for changing SM1 and SM2 as shown in Table 4 below in the synthesis method of the chemical formulas A4 and B4 above, A4-1 to A4-3 and B4-1 to B4-3 in Table 4 below were synthesized in the same manner.

[Table 4]

Synthesis of chemical formula A5

After dissolving SM1 (either A4 or B4, 1 eq) in dichloromethane (DCM, excess), tribromoboron (3 eq) was slowly added and stirred for 5 hours. After confirming the completion of the reaction, water saturated with sodium bicarbonate was used to neutralize and extract, and the solvent was removed by distillation under reduced pressure, and then column chromatography was performed with hexane and ethyl acetate to produce the chemical formula A5.

Except for changing SM1 and SM2 as shown in Table 5 below in the synthesis method of the chemical formula A5 above, A5-1 to A5-6 in Table 5 below were synthesized in the same manner.

[Table 5]

Synthesis of chemical formula A6

Compound A5 (1 eq) was dissolved in chloroform (excess), perfluorobutanesulfonic fluoride (1.5 eq) and potassium carbonate (3 eq) were added, and the mixture was stirred at room temperature for 6 hours. After confirming the completion of the reaction, the mixture was extracted three times with water, and then column chromatography was performed with hexane and ethyl acetate to produce the chemical formula A6.

Except for changing SM1 and SM2 as shown in Table 6 below in the synthesis method of the chemical formula A6 above, A6-1 to A6-6 in Table 6 below were synthesized in the same manner.

[Table 6]

Synthesis of chemical formula A7

Compound A6 (1 eq) and 1,8-diazabicyclo[5,4,0]undec-7-ene (1.5 eq) and lithium chloride (1 eq) were added to DMF (excess), stirred and heated, and bis(triphenylphosphine)palladium dichloride (0.1 eq) was added dropwise at 120°C, stirred and refluxed for 12 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, ethanol and water were added, filtered, and purified by column chromatography with ethyl acetate and hexane to produce the above chemical formula A7.

Except for changing SM1 and SM2 as shown in Table 7 below in the synthesis method of the chemical formula A7 above, A7-1 to A7-6 in Table 7 below were synthesized in the same manner.

[Table 7]

Synthesis of chemical formula A8

Compound A7 (1 eq) and SM2 (1.3 eq) were added to 1,4-dioxane (12 times the mass ratio compared to SM1), potassium acetate (3 eq) was added, stirred, and refluxed. Bis(diphenylpispino)ferrocene dichloropalladium (0.05 eq) was added after stirring in 1,4-dioxane for 5 minutes, and after 2 hours, the reaction was confirmed to be complete and cooled to room temperature. After adding ethanol and water, filtering was performed, and recrystallization with ethyl acetate and ethanol was purified to produce the above chemical formula A8.

Except for changing SM1 and SM2 as shown in Table 8 below in the synthesis method of the chemical formula A8 above, A8-1 to A8-6 in Table 8 below were synthesized in the same manner.

[Table 8]

Composition of Int

After adding SM1 (1 eq) and SM2 (1.1 eq or 2.1 eq) to tetrahydrofuran (excess), 2 M potassium carbonate aqueous solution (30 volume ratio with respect to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, and the mixture was heated and stirred at 85 ° C. for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed, the layers were separated, and the mixture was purified by column chromatography with hexane and ethyl acetate to produce the chemical formula int.

In the synthesis method of the chemical formula int. above, int 1. to int 12. of Table 9 below were synthesized in the same manner, except that SM1 and SM2 were changed as shown in Table 9 below.

[Table 9]

Synthesis of chemical formula 1

After adding SM1 (1 eq) and SM2 (1.1 eq or 1.1 eq per halogen number) to tetrahydrofuran (excess), 2 M potassium carbonate aqueous solution (30 volume ratio with respect to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, and the mixture was heated and stirred at 85 ° C. for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed, the layers were separated, and the mixture was purified by column chromatography with hexane and ethyl acetate to produce the above chemical formula 1.

Compounds 1 to 13 of Table 10 below were synthesized using the same method as in the synthetic method of Chemical Formula 1 above, except that SM1 and SM2 were changed as shown in Table 10 below.

[Table 10]

Synthesis of chemical formula 1D

The reactant (1 eq), Trifluoromethanesulfonic acid (cat.) was added to C ₆ D ₆ (mass ratio 10 to 50 times that of the reactant) and stirred at 70°C for 10 to 100 minutes. After completion of the reaction, D ₂ O (excess) was added and stirred for 30 minutes, and then trimethylamine (excess) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO ₄ and recrystallized by heating with toluene to obtain compounds 1-14 to 1-17 in Table 11 below.

[Table 11]

Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate can be determined based on the maximum m/z (M+) value.

<Manufacturing Example 2-1> Synthesis of Chemical Formula 2

The reactant (1 eq), Trifluoromethanesulfonic acid (cat.) was added to C ₆ D ₆ (mass ratio 10 to 50 times that of the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction was completed, D ₂ O (excess) was added and stirred for 30 minutes, and then trimethylamine (excess) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO ₄ and recrystallized by heating with toluene to obtain the product in Table 12 below.

[Table 12]

Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate can be determined based on the maximum m/z (M+) value.

The above reactants, Compound A to Compound W, were synthesized with reference to prior literature such as JP 4070676 B2, KR 1477844 B1, US 6465115 B2, JP 3148176 B2, JP 4025136 B2, JP 4188082 B2, JP 5015459 B2, KR 1979037 B1, KR 1550351 B1, KR 1503766 B1, KR 0826364 B1, KR 0749631 B1, and KR 1115255 B1. In addition, the compounds 1-A to 1-W, which are deuterium-substituted products, were synthesized with reference to the prior literature of KR 1538534 B1.

<Manufacturing Example 2-2> Synthesis of Chemical Formula 3

The reactant (1 eq), Trifluoromethanesulfonic acid (cat.) was added to C ₆ D ₆ (mass ratio 10 to 50 times that of the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction was completed, D ₂ O (excess) was added and stirred for 30 minutes, and then trimethylamine (excess) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO ₄ and recrystallized by heating with toluene to obtain the products in Tables 13 and 14 below.

[Table 13]

Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate can be determined based on the maximum m/z (M+) value.

The above reactants, Compound 1# to Compound 27#, were synthesized by referring to our prior literatures such as KR 1964435 B1, KR 1899728 B1, KR 1975945 B1, KR 2018-0098122 A, KR 2018-0102937 A, and KR 2018-0103352 A. In addition, the deuterium-substituted products, Compound 2-1 to 2-27, were synthesized by referring to the prior literature of KR 1538534 B1.

[Table 14]

Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate can be determined based on the maximum m/z (M+) value.

The above reactants, Compound 28# to Compound 47#, were synthesized by referring to our prior literatures such as KR 1994238 B1, KR 1670193 B1, KR 1754445 B1, and KR 1368164 B1. In addition, the products substituted with deuterium, Compound 2-28 to 2-47, were synthesized by referring to the prior literature of KR 1538534 B1.

Dipole moment (DM) and sublimation temperature of manufacturing example 2

[Table 15]

The properties of the compounds synthesized in the above manufacturing examples are shown in Table 15. Compounds A to W and compounds 1-A to 1-W have chemical structural differences in the carbon-hydrogen skeleton and carbon-deuterium skeleton, but have the same basic chemical skeleton and almost the same differences in dipole moments, so the numerical values thereof are collectively referred to as compounds A to W. In addition, compounds 1# to 47# are also the same as compounds 2-1 to 2-47, and the numerical values thereof are collectively referred to as compounds 2-1 to 2-47.

Among the compounds synthesized in the above manufacturing examples, the compounds corresponding to Chemical Formula 1 and the compounds corresponding to Chemical Formula 2 have chemical structural differences in dipole moments. Compounds A to W have a skeleton based only on carbon and hydrogen by having an aryl series substituent, and the compartmentalization of electrons within the chemical structure is limited, and accordingly, the dipole moment (DM) shows a result that does not exceed a maximum of 0.3 debye. On the other hand, compounds 1# to 47# have the potential to deepen the compartmentalization of electrons in a chemical structure having a carbon-hydrogen skeleton by substituting a furan containing an aryl or heteroaryl containing relatively electron-rich oxygen on the anthracene skeleton, and thus it can be confirmed that they have a relatively higher dipole moment (DM) than compounds A to W. Therefore, the combination of the two structures presented in the present application has a range in which the DM difference between the two hosts exceeds a minimum of 0.2.

l DM _host1 - DM _host2 l > 0.2

In addition, it can be confirmed that the sublimation temperature of the compound synthesized in the above manufacturing example is less than 400°C, and if it has a sublimation temperature higher than that, it has many limitations in using it as a material for an organic electroluminescent device.

And, in order to pre-sublimate a mixture of one of the compounds corresponding to chemical formula 2 and one of the hosts corresponding to chemical formula 3, it is desirable to satisfy the following formula.

[Formula 1]

|T _sub1 - T _sub2 | ≤ 20℃

In the above formula 1, T _sub1 is the sublimation temperature of the compound represented by the above formula 2, and T _sub2 is the sublimation temperature of the compound represented by the above formula 3.

When the above-described configuration is satisfied, the low voltage and high efficiency provided by the compound represented by the chemical formula 2 are reproduced, and electron injection into the triplet energy level of the dopant provided by the compound represented by the chemical formula 3 becomes easy, thereby increasing the formation ratio of excitons, so that there is an advantage of increased luminescence efficiency.

<Manufacturing Example 3> Manufacturing Example of a Mixture

The preliminary miscibility of two compounds (one each of formulae 2 and 3) corresponding to two hosts to be mixed was tested by high pressure liquid chromatography (HPLC) analysis of the evaporated membrane. In the preparation example of this mixture, compound J (formula 2) and compound 6# (formula 3) were used.

For this purpose, 0.15 g of compound J (or compound 1-J) and 0.15 g of compound 6# (or compound 2-6) were mixed 1:1 and ground. 0.3 g of the mixture was loaded into the evaporation source of a VTE vacuum chamber. The chamber was pumped and depressurized to a pressure of 10 ^-7 Torr. The premixed components were deposited on a glass substrate at a rate of 2 Å/sec. After depositing a 600 Å film, the substrate was replaced twice more consecutively without stopping the deposition process to avoid cooling the raw materials and to maintain the raw materials at a suitable temperature. The deposited films were analyzed by HPLC and the results are shown in Fig. 5 below. Three such substrate samples were taken and labeled as Film 1 to Film 3 below. The compositions of compound J (formula 2) and compound 6# (formula 3) did not change significantly from Film 1 to Film 3. A change in concentration before and after deposition of less than 10%, preferably less than 5% throughout the process is considered to be excellent and useful for commercial OLED applications, and it is believed that the difference in sublimation temperatures of the two mixed compounds can maintain the above concentration change at a temperature difference of less than 20°C. The difference in sublimation temperatures of the compound J and the compound 6# was 10°C.

As shown below, a slight variation in concentration did not reveal any trend in the element, and the sample collection and HPLC analysis could be explained by the following Equation 2. More specifically, the first compound (Compound J) or the second compound (Compound 6#) has a concentration C1 in the mixture, and a film formed by evaporating the mixture at a deposition rate of 1 Å ^/ s to 10 Å/s on a surface located a set distance away from a place where the mixture is evaporated in a high vacuum deposition apparatus having a chamber base pressure of 1 × 10 ^{-4 Torr to 1 × 10 -9} Torr has a concentration C2, and satisfies the following Equation 2.

[Formula 2]

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

The compound represented by compound 6# has a concentration of C1: 48.85% in the above composition, and therefore the concentration of Film 1 is 47.69%, so the concentration change is 2.3%, the concentration of Film 2 is 47.69%, so the concentration change is 3.9%, and the concentration of Film 3 is 47.69%, so the concentration change is 2.3%.

It was observed that the concentration change did not significantly change in the produced Films 1 to 3 and that the deviation between the films was small. Therefore, the above conditions are desirable.

<Manufacturing Example 4> Comparative Manufacturing Example of a Mixture

The following is an example of a mixture result that deviates from the conditions presented in this specification. In the comparative preparation example of the mixture below, compound B (chemical formula 2) and compound 24# (chemical formula 3) were used.

For mixing, 0.21 g of compound B (or compound 1-B) and 0.09 g of compound 24# (or compound 2-24) were mixed in a ratio of 7:3 and ground. The conditions for production were the same as those for the mixture of Manufacturing Example 3 above, and the results are shown in Figure 6 below.

According to the above formula 2; when the concentration of the compound represented by compound B in the above composition is C1: 69.30%, the concentration of Film 1 is 65.42%, so the concentration change is 5.5%, the concentration of Film 2 is 61.22%, so the concentration change is 11.6%, and the concentration of Film 3 is 62.82%, so the concentration change is 9.3%.

It was observed that the concentration change significantly changed in the produced Film 1 to Film 3, and in particular, a change of more than 10% was observed, and a large deviation between the films was observed. Therefore, the above conditions are not desirable.

<Example 1> Manufacturing of OLED

The substrate on which ITO/Ag/ITO was deposited as an anode at 70Å/1,000Å/70Å was cut into 50 mm × 50 mm × 0.5 mm sizes, placed in distilled water containing a dispersant, and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered twice through a filter of Millipore Co. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol solvents, and then dried.

On the anode thus prepared, HI-1 was vacuum-deposited with a thickness of 50Å to form a hole injection layer, and HT1, a material that transports holes, was vacuum-deposited with a thickness of 1,150Å thereon to form a hole transport layer. Next, a hole control layer was formed using EB1 (150Å). Next, the host compound 1-11 synthesized in Manufacturing Example 1 and the dopant BD1 (2 wt%) were vacuum-deposited with a thickness of 60Å to form a first emitting layer, and then the host compound A synthesized in Manufacturing Example 2 and the dopant BD1 (2 wt%) were vacuum-deposited with a thickness of 300Å to form a second emitting layer. Thereafter, HB1 was deposited with a thickness of 50Å to form an electron control layer, and the compound ET1 and Liq were mixed at a mass ratio of 5:5 to form an electron transport layer with a thickness of 250Å. After sequentially depositing 50Å thick magnesium and lithium fluoride (LiF) as electron injection layers, 200Å thick magnesium and silver (1:4) were formed as a cathode, and then 600Å thick CP1 was deposited to complete the device. During the above process, the deposition rate of the organic material was maintained at 1 Å/sec.

<Comparative Examples 1 to 8 and Examples 1 to 86>

Devices were manufactured in the same manner as in Example 1, except that in Comparative Examples 1 to 8 and Examples 1 to 86, the materials of the light-emitting layer were used as those described in Table 16 below.

The driving voltage, luminous efficiency, and time to reach 95% of the initial luminance (LT95) of the devices manufactured in Comparative Examples 1 to 8 and Examples 1 to 86 were measured at a current density of 20 mA/cm ² . The results are shown in Table 16 below.

[Table 16]

The results in Table 16 above are for a device structure in which the light-emitting layer is formed in two layers, and the host of the first light-emitting layer and the host of the second light-emitting layer are single hosts, and a compound according to one embodiment of the present application is configured as the host of the first light-emitting layer.

The above Comparative Examples 1 to 4 were not applied with a compound according to one embodiment of the present application, and a general aryl series anthracene host was used as the host for the second light-emitting layer, and showed lower efficiency and lifespan, and particularly, significantly higher voltage, compared to Examples 1 to 86. Among these, Comparative Examples 2 and 3 showed that even though the host for the second light-emitting layer had a structure containing deuterium and thus had a lifespan improvement effect to some extent, the effect of the overall device performance being significantly lower than that of the Examples was not significant. In Comparative Example 4, where BD2, a blue dopant of the boron series, was applied, the tendency was maintained compared to Comparative Example 2.

The above Comparative Examples 5 to 8 were not applied with a compound according to one embodiment of the present application, and a general heteroaryl series anthracene host was used as the host for the second light-emitting layer. Although these also showed a low voltage compared to Comparative Examples 1 to 4, they also showed low efficiency and lifespan and high voltage compared to Examples 1 to 86. Among these, Comparative Example 7 showed that, although there was a certain degree of lifespan improvement effect due to the structure in which the host for the second light-emitting layer contained deuterium like Comparative Examples 2 and 3, the effect of the overall device performance, which was significantly lower than that of the Examples, was not significant. In addition, in Comparative Example 8 where BD2, a blue dopant of the boron series, was applied, this tendency was also maintained compared to Comparative Example 7.

In Examples 1 to 86 of the present application, by applying a compound corresponding to Chemical Formula 1 as a host for the first light-emitting layer, the role of hole injection and electron barrier is enhanced and the light-emitting region within the light-emitting layer is changed, and by using an anthracene host substituted with the existing aryl and heteroaryl series as a host for the second light-emitting layer, it can be seen that the performance of the device is secured while maintaining the low-voltage characteristics and efficiency that are currently considered important in blue light-emitting devices.

Examples 1 to 23 were conducted in which a compound according to one embodiment of the present application was used as a host for a first light-emitting layer, and an aryl anthracene host was used as a host for a second light-emitting layer. The evaluations were conducted in cases where an H compound without deuterium was introduced as a host for the second light-emitting layer (Examples 1, 5, 8, 12, 16, 19, and 21) and a D compound with deuterium was introduced (the remaining cases), and the effect of the two-layer light-emitting layer was confirmed in each case. Data showing that additional improvement in lifespan through deuterium substitution of the second light-emitting layer host was possible were observed, and in addition, improvement in device performance was clearly confirmed when a compound according to one embodiment of the present application was used as a host for the first light-emitting layer.

In Examples 24 to 27, the compounds of the claimed invention were substituted with deuterium in comparison with Examples 23, 18, 17, and 14, and applied as hosts for the first light-emitting layer to compare the device results. In the case of the first light-emitting layer formed adjacent to the hole control layer, it was observed that the lifespan was additionally improved through deuterium substitution.

In Examples 28 to 31, only the blue dopant BD1 -> BD2 was applied to each light-emitting layer in the devices of Examples 24 to 27 to confirm the tendency and performance of the devices, and it was confirmed that when BD2, a boron series dopant, was used, additional efficiency was improved while maintaining the tendency for lifespan improvement.

Examples 32 to 58, unlike Examples 1 to 23, introduced anthracene derivatives bonded with various heteroaryls such as dibenzofuran, naphthobenzofuran, and triphenyldifuran as the host of the second light-emitting layer, and exhibited characteristics of relatively low voltage and low lifespan compared to Examples 1 to 23. However, in a device structure manufactured by applying a compound according to one embodiment of the present application as a host of the first light-emitting layer, it was confirmed that the device was improved while maintaining the characteristics as in Examples 1 to 23.

In Examples 79 to 86, changes were introduced similar to the results in Examples 24 to 31, and the results were verified as excellent device performance.

<Example 87> Manufacturing of OLED

The substrate on which ITO/Ag/ITO was deposited as an anode at 70Å/1,000Å/70Å was cut into 50 mm × 50 mm × 0.5 mm sizes, placed in distilled water containing a dispersant, and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered a second time through a filter of Millipore Co. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol solvents, and then dried.

On the anode thus prepared, HI-1 was vacuum-deposited with a thickness of 50Å to form a hole injection layer, and HT1, a material that transports holes, was vacuum-deposited with a thickness of 1,150Å to form a hole transport layer. Next, a hole control layer was formed using EB1 (150Å). Next, the host compound 1-2 synthesized in Manufacturing Example 1 and the dopant BD1 (2 wt%) were vacuum-deposited with a thickness of 60Å to form a first emitting layer, and then the host compound B synthesized in Manufacturing Example 2, the compound 2-3 synthesized in Manufacturing Example 2, and the dopant BD1 (2 wt%) were vacuum-co-deposited with a thickness of 300Å to form a emitting layer. Thereafter, HB1 was deposited with a thickness of 50Å to form an electron control layer, and the compound ET1 and Liq were mixed in a mass ratio of 5:5 to form an electron transport layer with a thickness of 250Å. After sequentially depositing 50Å thick magnesium and lithium fluoride (LiF) as electron injection layers, 200Å thick magnesium and silver (1:4) were formed as a cathode, and then 600Å thick CP1 was deposited to complete the device. During the above process, the deposition rate of the organic material was maintained at 1 Å/sec.

<Comparative Examples 9 to 18 and Examples 87 to 122>

Devices were manufactured in the same manner as in Example 87, except that in Comparative Examples 9 to 18 and Examples 87 to 122, the materials of the light-emitting layer were the materials described in Table 17 below.

However, the host of the second light-emitting layer showed both an example in which the light-emitting layer was formed by co-depositing two hosts through different evaporation sources during device fabrication, as shown in Table 17 below, and an example in which a pre-mixture of two host compounds was used.

In particular, the conditions for producing a pre-mixture of the host of the second light-emitting layer are as mentioned above, and both types of hosts of the second light-emitting layer applied to Comparative Examples 9 to 18 and Examples 87 to 122 of Table 17 can produce a pre-mixture, as shown in Table 18.

The driving voltage, luminous efficiency, and time to reach 95% of the initial luminance (LT95) of the devices manufactured in Comparative Examples 9 to 18 and Examples 87 to 122 were measured at a current density of 20 mA/cm ² . The results are shown in Table 17 below.

[Table 17]

The results in Table 17 above are when the light-emitting layer is formed of two layers, and the host of the first light-emitting layer is a compound according to one embodiment of the present application as a single host, and the host of the second light-emitting layer is composed of a mixed host-co-deposition or pre-mixture of two types of anthracene.

Comparative Examples 9 and 10 are examples in which a host for a second light-emitting layer was formed by co-deposition or preparing a pre-mixture using an H compound (skeleton with only hydrogen substituted) and a D compound (compound with some or all deuterium substituted), which are widely used, and depositing the mixture. Additionally, Comparative Examples 11, 12, and 13 are examples in which a host for a second light-emitting layer was formed by co-deposition or preparing a pre-mixture using an aryl anthracene compound and two kinds of heteroaryl anthracene compounds (at least one of the two kinds is a D compound). Comparative Examples 14, 15, and 16 are examples in which a host for a second light-emitting layer was formed by co-deposition or preparing a pre-mixture using two kinds of heteroaryl anthracene compounds (at least one of the two kinds is a D compound).

Compared to the case of a single host in Comparative Examples 1 to 8 of Table 16, it can be seen that forming a light-emitting layer using a mixed host improves the device performance. This can also be confirmed in prior literatures KR 2021-0148951 A and KR 2021-0092513 A. In addition, Comparative Examples 17 and 18 applied a boron-based blue dopant like Comparative Example 4 of Table 16, and it can be confirmed that even in the case of a mixed host (co-deposition or pre-mixture preparation), the characteristics were maintained and the device performance was improved.

Examples 87 to 102 are examples including the features of the present application described above, in which a compound according to one embodiment of the present application is used as a host for the first light-emitting layer, and a host for the second light-emitting layer is formed by co-deposition (1:1 mass ratio) of a combination of various anthracene compounds (aryl or heteroaryl series, one of which is a deuterium-substituted D compound), thereby showing excellent voltage and efficiency characteristics compared to Comparative Examples 9 to 18, and it can be observed that the lifespan can also be increased.

Examples 103 to 106, unlike the host of the second light-emitting layer of Examples 87 to 102, were co-deposited with a D compound in which both hosts were substituted with deuterium to fabricate the devices, and showed an average of 15% additional lifetime increase compared to Examples 92, 87, 95, and 93. In addition, Examples 107 to 110, unlike Examples 103 to 106, were formed by applying Compounds 1-14 to 1-17, which are deuterated versions of Compounds 1-1, 1-2, 1-5, and 1-12 among the compounds of the first light-emitting layer, to fabricate the devices. As mentioned in the results of Table 16, it was observed that the lifespan was additionally improved through deuterium substitution in the first light-emitting layer formed adjacent to the hole control layer.

Examples 111 to 114 are devices manufactured by changing the host co-deposition method of the second light-emitting layer of Examples 107 to 110 to a method in which two types of hosts are formed as a pre-mixture and then evaporated from a single deposition source. The conditions for forming the pre-mixture were implemented with reference to the text, and the device performance of the co-deposition device is maintained or stably improved due to the even mixing effect at the molecular level.

Examples 115 to 118 show that one or both of the dual light-emitting layers are applied with BD2 (a boron-based blue dopant) and a pre-mixed host, and that the advantages of the pre-mixed host are maintained while maintaining high efficiency compared to the pyrene dopant.

Examples 119 to 122 are cases where the host was formed by depositing the two compounds of the pre-mixture of the second light-emitting layer in Examples 115 to 118 by changing the ratio, thereby showing that the advantages and disadvantages of the two compounds can be reflected in the device by applying them through the ratio.

1: Substrate
2: First electrode
3: Second electrode
4: Emitting layer
4-1: First light-emitting layer
4-2: Second light-emitting layer
5: Hole injection layer
6: Hole transport layer
7: Hole control layer
8: Electronic control layer
9: Electron transport layer
10: Electron injection layer
11: Capping layer

Claims (19)

A compound of the following chemical formula 1:
[Chemical Formula 1]

In the above chemical formula 1,
One of R ₁ to R ₁₀ is a moiety bonded to L ₁ , and the rest are the same or different from each other, and each independently represents hydrogen; deuterium; 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 bonds with adjacent groups to form a substituted or unsubstituted ring,
L ₁ is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,
Ar ₁ is a substituted or unsubstituted benzoxanthine group; a substituted or unsubstituted benzothioxanthine group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group,
x is 1 or 2,
m is 0 to 3, and when m is 2 or more, two or more L ₁ are equal to or different from each other,
y is 1 or 2, and when y is 2, the two Ar ₁ are equal or different. In claim 1, the chemical formula 1 is a compound having the following chemical formula 1-A:
[Chemical Formula 1-A]

In the above chemical formula 1-A,
The definitions of R ₁ to R ₁₀ , L ₁ , x, m, and y are the same as those defined in the chemical formula 1 above,
X ₁ is O or S,
Any one of R ₁₀₁ to R ₁₁₀ is a moiety bonded to L ₁ , and the rest are the same or different, and each independently represents hydrogen; deuterium; 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 bonds with adjacent groups to form a substituted or unsubstituted ring. In claim 1, the chemical formula 1 is a compound having the following chemical formula 1-B:
[Chemical Formula 1-B]

In the above chemical formula 1-B,
The definitions of R ₁ to R ₁₀ , L ₁ , x, m, and y are the same as those defined in the chemical formula 1 above,
X ₂ is O, S or NR,
One of R ₂₀₁ to R ₂₁₀ , and R is a moiety bonded to L ₁ , and the rest are the same or different, and each independently represents hydrogen; deuterium; 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 bonds with adjacent groups to form a substituted or unsubstituted ring. A compound according to claim 1, wherein the chemical formula 1 contains at least one deuterium. A compound according to claim 1, wherein the deuterium substitution rate of the chemical formula 1 is 40% to 99%. In claim 1, the chemical formula 1 is a compound selected from the following compounds:






In claim 1, the chemical formula 1 is a compound selected from the following compounds:





In claim 1, the chemical formula 1 is a compound selected from the following compounds:




In claim 1, the chemical formula 1 is a compound selected from the following compounds:






In claim 1, the chemical formula 1 is a compound selected from the following compounds:




In claim 1, the chemical formula 1 is a compound selected from the following compounds:




An anode; a cathode; a first light-emitting layer provided between the anode and the cathode; and a second light-emitting layer provided between the first light-emitting layer and the cathode and in contact with the first light-emitting layer,
The first light-emitting layer comprises a compound according to any one of claims 1 to 11,
An organic light-emitting device wherein the second light-emitting layer comprises at least one compound of the following chemical formula 2 and chemical formula 3:
[Chemical formula 2]

In the above chemical formula 2,
At least one of R11 to R20 is bonded to the * moiety of the following chemical formula 2-1, and the rest are the same or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group,
[Chemical Formula 2-1]

L2 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar2 is a substituted or unsubstituted aryl group,
p is an integer from 1 to 3,
[Chemical Formula 3]

In the above chemical formula 3,
At least one of Y1 to Y10 is bonded to the * moiety of the following chemical formula 3-1, and the rest are the same or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted silyl group,
[Chemical Formula 3-1]

A and B are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted aromatic heterocycle,
L3 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
q is an integer from 1 to 3. In claim 12, the first light-emitting layer comprises the compound as a host of the first light-emitting layer,
An organic light-emitting device wherein the second light-emitting layer comprises at least one compound of the chemical formula 2 and the chemical formula 3 as a host for the second light-emitting layer. An organic light-emitting device according to claim 13, wherein each of the first light-emitting layer and the second light-emitting layer additionally includes a dopant, and the dopant includes a fluorescent dopant. An organic light-emitting device according to claim 14, wherein the fluorescent dopant comprises at least one selected from a pyrene-based compound and a non-pyrene-based compound. An organic light-emitting device according to claim 15, wherein the non-pyrene-based compound includes a boron-based compound. An organic light-emitting device according to claim 12, wherein the second light-emitting layer comprises a compound of chemical formula 2 or a compound of chemical formula 3. An organic light-emitting device according to claim 12, wherein the second light-emitting layer comprises a compound of chemical formula 2 and a compound of chemical formula 3. An organic light-emitting device according to claim 12, wherein the deuterium substitution rates of chemical formulas 2 and 3 are each 40% to 99%.