KR102903864B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light-emitting device comprising the same.

Description

Compound and organic light-emitting device comprising the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

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

In general, organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light emitting devices that utilize the organic light emitting phenomenon typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials 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 continuing need for the development of new materials for organic light-emitting devices such as the above.

Korean Patent Publication No. 2015-0073064 Korean Patent No. 10-1538534

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

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

[Chemical Formula 1]

In the above chemical formula 1,

R1 to R4 are the same or different and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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,

L1 and L2 are the same or different, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

Ar is represented by the following chemical formula A-1 or A-2,

[Chemical Formula A-1]

[Chemical Formula A-2]

In the above chemical formulas A-1 and A-2,

X1, Y1 and Y2 are equal to or different from each other, and are each independently O; S; or CR'R'',

Any one of R11 to R14 and Ra is bonded to L2,

Any one of R21 to R24 and Rb is bonded to L2,

Among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same or different, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 bond to adjacent groups to form a substituted or unsubstituted ring,

R' and R'' are the same or different, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 are combined with adjacent groups to form a substituted or unsubstituted ring,

m is an integer from 1 to 4, and when m is 2 or more, 2 or more Ar are equal to or different from each other,

n1 and n2 are integers from 0 to 4, and when n1 and n2 are each 2 or more, 2 or more R1 and R2 are each equal to or different from each other,

n3 is an integer from 0 to 3, and when n3 is 2 or greater, 2 or more R3s are equal to or different from each other,

n4 is an integer from 0 to 8, and if n4 is 2 or greater, 2 or more R4s are equal to or different from each other,

n2+n3 is 0 to 6,

a and b are integers from 0 to 6, and when a and b are each 2 or greater, Ra and Rb, which are 2 or greater, are each equal to or different from each other.

In addition, one embodiment of the present specification provides an organic light-emitting device including an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes a compound represented by the chemical formula 1.

The compounds described herein can be used as materials for an organic layer of an organic light-emitting device. The compounds according to at least one embodiment can improve efficiency, lower operating voltage, and/or improve lifespan characteristics in an organic light-emitting device. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, luminescence, hole blocking, electron transport, or electron injection materials. In addition, compared to existing organic light-emitting devices, they have the effects of lower operating voltage, higher efficiency, and/or longer lifespan.

Figure 1 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (6), and a cathode (10) are sequentially stacked.
Figure 2 illustrates an example of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron transport layer (8), an electron injection layer (9), a cathode (10), and a capping layer (11) are sequentially laminated.

The following describes this specification in more detail.

In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

In this specification, when it is said that a member is located “on” another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

In this specification, " " or dotted lines indicate positions where the chemical formula or compound is bonded.

In the present specification, the deuterium substitution rate of a compound can be determined by a method of calculating the substitution rate based on the max. value of the distribution of molecular weights at the end of the reaction using TLC-MS (Thin-Layer Chromatography/Mass Spectrometry), or by a quantitative analysis method using NMR, adding DMF as an internal standard, and calculating the D-substitution rate from the total peak integration amount using the integration ratio on 1H NMR.

In this specification, "energy level" refers to energy magnitude. Therefore, the term "energy level" is interpreted to refer to the absolute value of the corresponding energy value. For example, a low or deep energy level means that the absolute value increases in a negative direction from the vacuum level.

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

In this specification, bandgap means the difference in energy levels between HOMO and LUMO, i.e., HOMO-LUMO gap.

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).

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

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 substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, 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 nitrile group (-CN); a nitro group; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkoxy group; a phosphine oxide group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; an alkenyl group; a silyl group; a boron group; an amine group; an aryl group; or a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are connected, or having no substituents. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxy group; amino group; silyl group; boron group; alkoxy group; aryloxy group; alkyl group; cycloalkyl group; aryl group; and heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

The term "substituted or unsubstituted" in this specification means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; alkyl group; aryl group; and heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

In this specification, N% substitution with deuterium means that N% of the available hydrogens in the structure are replaced with deuterium. For example, if dibenzofuran is 25% substituted with deuterium, it means that two of the eight hydrogens in dibenzofuran are replaced with deuterium.

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

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

In the present specification, a silyl group may be represented by the chemical formula -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, the boron group may be represented by the chemical formula -BY _d Y _e , wherein Y _d and Y _e may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group.

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

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

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 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

Substituents comprising alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight-chain and branched forms.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. 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 the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkynyl group is 2 to 10.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and an adamantyl group.

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

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, or the like. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, or the like.

In the present specification, the substituted aryl group may include a structure in which an aliphatic hydrocarbon ring is condensed with the aryl group. According to one embodiment, the substituted aryl group may include a tetrahydronaphthalene group, and more specifically, (1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene group), but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

When the above fluorenyl group is substituted, , , Spirofluorenyl group of etc. (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group), but is not limited thereto.

In this specification, the aryl group among the aryloxy groups may be applied to the description of the aryl group described above.

In this specification, the description regarding the alkyl group described above may be applied to the alkyl group among the alkylthioxy group and alkylsulfoxy group.

In this specification, the description regarding the aryl group described above can be applied to the aryl group among the arylthioxy group and arylsulfoxy group.

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

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

In this specification, the description of the alkyl group may be applied except that the alkylene group is divalent.

In this specification, the description of the aryl group may be applied except that the arylene group is divalent.

In this specification, the description of the above heterocyclic group may be applied to the divalent heterocyclic group except that the divalent heterocyclic group is divalent.

In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, “ring” means a hydrocarbon ring; or a heterocycle.

The above hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the above cycloalkyl group or aryl group.

In the present specification, forming a ring by bonding with adjacent groups means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof by bonding with adjacent groups. The hydrocarbon ring means a ring composed only of carbon and hydrogen atoms. The heterocycle means a ring containing one or more elements selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle, and the aromatic heterocycle may be monocyclic or polycyclic.

In this specification, an aliphatic hydrocarbon ring means a non-aromatic ring composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

In this specification, an aromatic hydrocarbon ring means an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring can be interpreted to have the same meaning as an aryl group.

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, azocane, and thiocane.

In this specification, an aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, dryazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, Examples include, but are not limited to, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

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

The compound represented by chemical formula 1 according to the present invention has excellent voltage, efficiency, and life characteristics by including an indolocarbazole structure and a four- or more-ring ring structure represented by chemical formula A in the anthracene structure.

Additionally, when the compound represented by Chemical Formula 1 of the present invention contains deuterium, the efficiency and lifespan of the device are improved. Specifically, when hydrogen is replaced with deuterium, the chemical properties of the compound remain largely unchanged, but the physical properties of the deuterated compound change, resulting in a lower vibrational energy level. The deuterium-substituted compound can prevent a decrease in quantum efficiency due to a decrease in intermolecular van der Waals forces or collisions caused by intermolecular vibration. In addition, the C-D bond can improve the stability of the compound.

Therefore, when the compound represented by the above-described chemical formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage, and/or long life characteristics can be obtained.

Hereinafter, chemical formula 1 is described in detail.

[Chemical Formula 1]

In the above chemical formula 1,

R1 to R4 are the same or different and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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,

L1 and L2 are the same or different, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

Ar is represented by the following chemical formula A-1 or A-2,

[Chemical Formula A-1]

[Chemical Formula A-2]

In the above chemical formulas A-1 and A-2,

X1, Y1 and Y2 are equal to or different from each other, and are each independently O; S; or CR'R'',

Any one of R11 to R14 and Ra is bonded to L2,

Any one of R21 to R24 and Rb is bonded to L2,

Among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same or different, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 bond to adjacent groups to form a substituted or unsubstituted ring,

R' and R'' are the same or different, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 are combined with adjacent groups to form a substituted or unsubstituted ring,

m is an integer from 1 to 4, and when m is 2 or more, 2 or more Ar are equal to or different from each other,

n1 and n2 are integers from 0 to 4, and when n1 and n2 are each 2 or more, 2 or more R1 and R2 are each equal to or different from each other,

n3 is an integer from 0 to 3, and when n3 is 2 or greater, 2 or more R3s are equal to or different from each other,

n4 is an integer from 0 to 8, and if n4 is 2 or greater, 2 or more R4s are equal to or different from each other,

n2+n3 is 0 to 6,

a and b are integers from 0 to 6, and when a and b are each 2 or greater, Ra and Rb, which are 2 or greater, are each equal to or different from each other.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted O, S, or N-containing heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; an alkylsilyl group having 1 to 20 carbon atoms; an alkyl group having 1 to 20 carbon atoms; a cycloalkyl group having 3 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms, wherein the groups are unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; an alkylsilyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkylsilyl group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted cyclopentyl group; a substituted or unsubstituted cyclohexyl group; 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 fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted thiophene group; a substituted or unsubstituted benzothiophene group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; a trimethylsilyl group; a methyl group; an ethyl group; a propyl group; a butyl group; a cyclopentyl group; a cyclohexyl group; a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a phenanthrenyl group; a triphenylenyl group; a furan group; a benzofuran group; a dibenzofuran group; a thiophene group; a benzothiophene group; or a dibenzothiophene group, and the groups are unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; i-propyl group; t-butyl group; cyclopentyl group; cyclohexyl group; phenyl group; biphenyl group; naphthyl group; or a thiophene group unsubstituted or substituted with a phenyl group, wherein the groups are unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; i-propyl group; t-butyl group; cyclopentyl group; cyclohexyl group; phenyl group; biphenyl group; naphthyl group; or a thiophene group unsubstituted or substituted with a phenyl group.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently represent hydrogen; deuterium; i-propyl group; t-butyl group; cyclopentyl group; cyclohexyl group; phenyl group; naphthyl group; or a thiophene group unsubstituted or substituted with a phenyl group.

In one embodiment of the present specification, R1 to R3 are the same as or different from each other, and are each independently hydrogen; t-butyl group; cyclohexyl group; phenyl group; or thiophene group.

In one embodiment of the present specification, R4 is hydrogen; deuterium; a phenyl group; a biphenyl group; or a naphthyl group.

In one embodiment of the present specification, R4 is hydrogen; or a phenyl group.

In one embodiment of the present specification, R1 to R4 are each independently substituted or unsubstituted with deuterium.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms, wherein the groups are substituted or unsubstituted with deuterium; a cyano group; an alkyl group having 1 to 20 carbon atoms; a cycloalkyl group having 3 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent O, S or N-containing heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or a divalent O, S or N-containing heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; a substituted or unsubstituted divalent furan group; a substituted or unsubstituted divalent benzofuran group; a substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent thiophene group; a substituted or unsubstituted divalent benzothiophene group; a substituted or unsubstituted divalent dibenzothiophene group; a substituted or unsubstituted divalent carbazole group; or a substituted or unsubstituted divalent pyridyl group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represent a direct bond; a phenylene group; a biphenylene group; a terphenylene group; a naphthylene group; a phenanthrenylene group; a triphenylenylene group; a divalent furan group; a divalent benzofuran group; a divalent dibenzofuran group; a divalent thiophene group; a divalent benzothiophene group; a divalent dibenzothiophene group; or a divalent pyridyl group, wherein the groups are unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a phenylene group; a biphenylene group; a naphthylene group; a divalent thiophene group; or a divalent pyridyl group, wherein the groups are substituted or unsubstituted with deuterium.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a phenylene group; a biphenylene group; a naphthylene group; a divalent thiophene group; or a divalent pyridyl group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a phenylene group; a biphenylene group; or a naphthylene group.

In one embodiment of the present specification, L1 is a direct bond; a phenylene group; a biphenylene group; or a naphthylene group.

In one embodiment of the present specification, L1 is a direct bond; a phenylene group; or a naphthylene group.

In one embodiment of the present specification, L2 is a direct bond; a phenylene group; a biphenylene group; a naphthylene group; a divalent thiophene group; or a divalent pyridyl group.

In one embodiment of the present specification, L2 is a direct bond; a biphenylene group; or a naphthylene group.

In one embodiment of the present specification, L1 and L2 are each independently substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar is represented by the following chemical formula A-1 or A-2.

[Chemical Formula A-1]

[Chemical Formula A-2]

In the above chemical formulas A-1 and A-2,

X1, Y1 and Y2 are equal to or different from each other, and are each independently O; S; or CR'R'',

Any one of R11 to R14 and Ra is bonded to L2,

Any one of R21 to R24 and Rb is bonded to L2,

Among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same or different, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 bond to adjacent groups to form a substituted or unsubstituted ring,

R' and R'' are the same or different, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 are combined with adjacent groups to form a substituted or unsubstituted ring,

a and b are integers from 0 to 6, and when a and b are each 2 or greater, Ra and Rb, which are 2 or greater, are each equal to or different from each other.

In one embodiment of the present specification, X1 is O.

In one embodiment of the present specification, X1 is S.

In one embodiment of the present specification, X1 is CR'R''.

In one embodiment of the present specification, Y1 and Y2 are O.

In one embodiment of the present specification, Y1 and Y2 are S.

In one embodiment of the present specification, Y1 and Y2 are CR'R''.

In one embodiment of the present specification, Y1 is O and Y2 is S.

In one embodiment of the present specification, Y1 is O and Y2 is CR'R''.

In one embodiment of the present specification, Y1 is S and Y2 is O.

In one embodiment of the present specification, Y1 is S and Y2 is CR'R''.

In one embodiment of the present specification, Y1 is CR'R'' and Y2 is O.

In one embodiment of the present specification, Y1 is CR'R'' and Y2 is S.

In one embodiment of the present specification, R11 is bonded to L2.

In one embodiment of the present specification, R12 is bonded to L2.

In one embodiment of the present specification, R13 is bonded to L2.

In one embodiment of the present specification, R14 is bonded to L2.

In one embodiment of the present specification, Ra is bonded to L2.

In one embodiment of the present specification, R21 is bonded to L2.

In one embodiment of the present specification, R22 is bonded to L2.

In one embodiment of the present specification, R23 is bonded to L2.

In one embodiment of the present specification, R24 is bonded to L2.

In one embodiment of the present specification, Rb is bonded to L2.

In one embodiment of the present specification, among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same as or different from each other, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 bond to adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same as or different from each other, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or bonds to adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.

In one embodiment of the present specification, among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same as or different from each other, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonds to adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

In one embodiment of the present specification, among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same as or different from each other, and each independently represents hydrogen; deuterium; a cyano group; an alkylsilyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or bonds to adjacent groups to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

In one embodiment of the present specification, among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkylsilyl group; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted cyclopentyl group; a substituted or unsubstituted cyclohexyl group; 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 fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted thiophene group; A substituted or unsubstituted benzothiophene group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group, or bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same as or different from each other, and are each independently hydrogen; deuterium; trimethylsilyl group; methyl group; ethyl group; propyl group; butyl group; cyclopentyl group; cyclohexyl group; phenyl group; biphenyl group; terphenyl group; naphthyl group; dimethylfluorenyl group; diphenylfluorenyl group; phenanthrenyl group; triphenylenyl group; furan group; benzofuran group; dibenzofuran group; thiophene group; benzothiophene group; or dibenzothiophene group, and the groups are unsubstituted or substituted with deuterium.

In one embodiment of the present specification, among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same or different, and are each independently hydrogen; deuterium; i-propyl group; t-butyl group; trimethylsilyl group; cyclopentyl group; cyclohexyl group; or phenyl group, and the groups are substituted or unsubstituted with deuterium.

In one embodiment of the present specification, among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same or different, and are each independently hydrogen; deuterium; i-propyl group; t-butyl group; trimethylsilyl group; cyclopentyl group; cyclohexyl group; or phenyl group.

In one embodiment of the present specification, the groups not bonded to L2 among R11 to R14, R21 to R24, Ra and Rb are the same as or different from each other, and are each independently hydrogen; i-propyl group; t-butyl group; trimethylsilyl group; or phenyl group.

In one embodiment of the present specification, the groups not bonded to L2 among R11 to R14, R21 to R24, Ra and Rb are each independently substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or are bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.

In one embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or are bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

In one embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

In one embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently represents an alkyl group having 1 to 20 carbon atoms, which is unsubstituted or substituted with deuterium; or an aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with deuterium; or are bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, which is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently represents a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group, or combine with an adjacent group to form a substituted or unsubstituted fluorene ring.

In one embodiment of the present specification, R' and R'' are the same as or different from each other, and each independently represents a methyl group substituted or unsubstituted with deuterium; or a phenyl group substituted or unsubstituted with deuterium; or are bonded to an adjacent group to form a fluorene ring substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R' and R'' are the same or different, and each independently represents a methyl group; or a phenyl group, or are bonded to an adjacent group to form a fluorene ring.

In one embodiment of the present specification, R' and R'' are each independently substituted or unsubstituted with deuterium.

In one embodiment of the present specification, m is 1 or 2.

In one embodiment of the present specification, m is 1.

In one embodiment of the present specification, n1 and n2 are integers from 0 to 2.

In one embodiment of the present specification, n3 is an integer from 0 to 2.

In one embodiment of the present specification, n4 is an integer from 0 to 8.

In one embodiment of the present specification, n4 is 0 or 1.

In one embodiment of the present specification, n4 is 8.

In one embodiment of the present specification, a and b are integers from 0 to 2.

In one embodiment of the present specification, the chemical formula A-1 is represented by any one of the following chemical formulas A-1-1 to A-1-4.

[Chemical Formula A-1-1]

[Chemical Formula A-1-2]

[Chemical Formula A-1-3]

[Chemical Formula A-1-4]

In the above chemical formulas A-1-1 to A-1-4, the definitions of X1 and R11 to R14 are the same as those in the above chemical formula A-1,

One of R11 to R14, Ra1 to Ra4, Ra11 to Ra14, Ra21 to Ra24 and Ra31 to Ra34 is bonded to L2, and the others not bonded to L2 are the same or different, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 are bonded to adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, the definitions of Ra1 to Ra4, Ra11 to Ra14, Ra21 to Ra24 and Ra31 to Ra34 are the same as the definition of Ra described above.

In one embodiment of the present specification, the chemical formula A-2 is represented by any one of the following chemical formulas A-2-1 to A-2-6.

In the above chemical formulas A-2-1 to A-2-6, the definitions of Y1, Y2 and R11 to R14 are the same as those in the above chemical formula A-2,

One of R11 to R14, Rb1 to Rb4, Rb11 to Rb14, Rb21 to Rb24 and Rb31 to Rb34 is bonded to L2, and the others not bonded to L2 are the same or different, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 are bonded to adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, the definitions of Rb1 to Rb4, Rb11 to Rb14, Rb21 to Rb24 and Rb31 to Rb34 are the same as the definition of Rb described above.

In one embodiment of the present specification, the chemical formula A-2 is represented by any one of the following chemical formulas B1 to B5.

In the above chemical formulas B1 to B5, the definitions of Y1, R11 to R14, Rb and b are the same as those in the above chemical formula A-2.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-6.

[Chemical Formula 1-1]

[Chemical Formula 1-2]

[Chemical Formula 1-3]

[Chemical Formula 1-4]

[Chemical Formula 1-5]

[Chemical Formula 1-6]

In the above chemical formulas 1-1 to 1-6, the definitions of R1 to R4, L1, L2, Ar, m and n1 to n4 are the same as those in the above chemical formula 1,

n2' is an integer from 0 to 3, and when n2' is 2 or greater, 2 or more R2 are equal to or different from each other,

n3' is an integer from 0 to 2, and when n3' is 2, two R3s are equal to or different from each other.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-3.

[Chemical Formula 2-1]

[Chemical Formula 2-2]

[Chemical Formula 2-3]

In the above chemical formulas 2-1 to 2-3, the definitions of R1 to R3, L1, L2, Ar, m and n1 to n3 are the same as those in the above chemical formula 1,

G1 to G8 are the same or different from each other, and are each independently hydrogen; or deuterium,

Ar11 and Ar12 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents a phenyl group; a biphenyl group; or a naphthyl group.

In one embodiment of the present specification, Ar11 and Ar12 are each independently substituted or unsubstituted with deuterium.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 is substituted at least 40% with deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted at least 50% with deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted at least 60% with deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted at least 70% with deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted at least 80% with deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted at least 90% with deuterium. In another embodiment, the compound represented by Chemical Formula 1 is substituted at least 100% with deuterium.

In one embodiment of the present specification, the compound represented by the chemical formula 1 contains 40% to 60% of deuterium. In another embodiment, the compound represented by the chemical formula 1 contains 40% to 80% of deuterium. In another embodiment, the compound represented by the chemical formula 1 contains 60% to 80% of deuterium. In another embodiment, the compound represented by the chemical formula 1 contains 80% to 100% of deuterium.

In one embodiment of the present specification, R1 to R4 are the same as or different from each other, and each can be independently substituted with deuterium.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each can be independently substituted with deuterium.

In one embodiment of the present specification, Ar may be substituted with deuterium.

In one embodiment of the present specification, R11 to R14, R21 to R24, Ra and Rb are the same as or different from each other, and can each be independently substituted with deuterium.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following compounds.

The above compounds are substituted or unsubstituted with deuterium.

The compound represented by Chemical Formula 1 according to one embodiment of the present specification can have a core structure manufactured as in the manufacturing example described below. The substituents can be bonded by a method known in the art, and the type, position, or number of the substituents can be changed according to a technique known in the art.

In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can also be controlled by introducing various substituents into the core structure of the above structure.

In addition, the present specification provides an organic light-emitting device comprising the compound described above.

An organic light-emitting device according to the present specification is an organic light-emitting device comprising an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers comprises a compound represented by the above-described chemical formula 1.

The organic light-emitting device of the present specification can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that an organic layer is formed using the compound of the above-described chemical formula 1.

The above compound 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 refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

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 multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including at least one layer of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as the organic layer. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller or larger number of organic layers.

In the organic light-emitting device of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include a compound represented by the chemical formula 1 described above.

In the organic light-emitting device of the present specification, the organic layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include a compound represented by the chemical formula 1 described above.

In one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer may include a compound represented by the chemical formula 1 described above.

In the organic light-emitting device of the present specification, the organic layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, electron injection layer, or electron transport and injection layer may include a compound represented by the above-described chemical formula 1.

In one embodiment of the present specification, the organic layer includes an electron control layer, and the electron control layer may include a compound represented by the chemical formula 1 described above.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 described above.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the above-described chemical formula 1 as a host.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the above-described chemical formula 1 as a blue host.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the above-described chemical formula 1 as a dopant.

In one embodiment of the present specification, the organic light-emitting device is a green organic light-emitting device in which the light-emitting layer includes a compound represented by the chemical formula 1 as a host.

According to one embodiment of the present specification, the organic light-emitting device is a red organic light-emitting device in which the light-emitting layer includes a compound represented by the chemical formula 1 as a host.

In another embodiment, the organic light-emitting device is a blue organic light-emitting device in which the light-emitting layer includes a compound represented by the chemical formula 1 as a host.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 as a host and may further include a dopant. At this time, the content of the dopant may be included in an amount of 1 to 60 parts by weight based on 100 parts by weight of the host, and is preferably included in an amount of 1 to 10 parts by weight.

At this time, as the dopant, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, PPV polymer, anthracene compound, pyrene compound, boron compound, etc. may be used, but is not limited thereto.

In another embodiment, the organic layer may further include another organic compound, metal, or metal compound in addition to the compound represented by the above-described chemical formula 1.

In an organic light-emitting device according to one embodiment of the present specification, the light-emitting layer further includes a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the light-emitting layer is included in an amount of 1 to 50 parts by weight relative to 100 parts by weight of the host.

In one embodiment of the present specification, the thickness of the organic layer including the compound represented by the chemical formula 1 is 10 Å to 500 Å, in one example, 50 Å to 400 Å, and in another example, 100 Å to 400 Å.

In an organic light-emitting device according to one embodiment of the present specification, the maximum emission peak of the organic layer is 400 nm to 500 nm. In another embodiment, the maximum emission peak of the organic layer is 400 nm to 470 nm.

As another example, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the chemical formula 1 as a host, and may further include an additional host.

In one embodiment of the present specification, the dopant includes an arylamine compound, a heterocyclic compound containing boron and nitrogen, or an Ir complex.

In one embodiment of the present specification, the fluorescent dopant may be selected from the following structures, but is not limited thereto.

In one embodiment of the present specification, an Ir complex may be used as the phosphorescent dopant, and any one of the following structures may be used as an example, but is not limited thereto.

In one embodiment of the present specification, the light-emitting layer including the compound represented by the chemical formula 1 is blue.

According to one example, the content of the compound represented by the above chemical formula 1 is 70 parts by weight to 99.99 parts by weight based on 100 parts by weight of the total of the host and dopant of the light-emitting layer; preferably, 80 parts by weight to 99.9 parts by weight; more preferably, 90 parts by weight to 99.5 parts by weight.

In one embodiment of the present specification, the organic layer includes the compound, and the band gap energy of the compound is 2.9 eV or more.

The organic light-emitting device of the present specification may further include at least one organic layer among a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

In one embodiment of the present specification, the organic light-emitting device includes an anode; a cathode; and two or more organic layers provided between the anode and the cathode, and at least one of the two or more organic layers includes a compound represented by the chemical formula 1.

In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.

In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.

In one embodiment of the present specification, the organic layer includes two or more light-emitting layers, and at least one of the two or more light-emitting layers includes a compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be included in one layer of the two or more light-emitting layers, and may be included in each of the two or more light-emitting layers.

In one embodiment of the present specification, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

In addition, in one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, other materials except for the compound represented by the chemical formula 1 may be the same or different from each other.

When the organic layer containing the compound represented by the above chemical formula 1 is an electron transport layer, the electron transport layer may further contain an n-type dopant. The n-type dopant may be one known in the art, and may be, for example, a metal or a metal complex. For example, the electron transport layer containing the compound represented by the above chemical formula 1 may further contain LiQ (Lithium Quinolate).

In one embodiment of the present specification, the organic layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes a compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be included in one layer of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.

In addition, in one embodiment of the present specification, when the compound represented by the chemical formula 1 is included in each of the two or more hole transport layers, other materials except the compound represented by the chemical formula 1 may be the same or different from each other.

In one embodiment of the present specification, the organic layer may further include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the compound represented by the chemical formula 1.

In 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 layers, and a cathode are sequentially stacked on a substrate.

In 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 layers, and an anode are sequentially stacked on a substrate.

In the organic light-emitting device of the present invention, the organic layer may include an electron blocking layer, and a material known in the art may be used for the electron blocking layer.

The above organic light-emitting device may have a laminated structure, for example, as follows, but is not limited thereto.

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

(2) Anode/hole injection layer/hole transport layer/light-emitting layer/cathode

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

(4) Anode/hole transport layer/light-emitting layer/electron transport layer/cathode

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

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

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

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

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

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

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

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

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

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

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

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

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

(18) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode/capping layer

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

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

FIG. 2 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light-emitting layer (6), a hole blocking layer (7), an electron transport layer (8), an electron injection layer (9), a cathode (10), and a capping layer (11) are sequentially laminated. In this structure, the compound may be included in the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the light-emitting layer (6), the hole blocking layer (7), the electron transport layer (8), or the electron injection layer (9).

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

The above organic layer may further include at least one layer of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers by using various polymer materials and a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

The anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are 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.

The above cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material 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; multilayered materials such as LiF/Al or LiO ₂ /Al.

The above hole injection layer is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage, and 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, but are not limited to, metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene. The thickness of the hole injection layer may be 1 nm to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of being able to prevent the hole injection characteristics from being deteriorated, and if it is 150 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of holes due to the thickness of the hole injection layer being too thick.

In one embodiment of the present specification, the hole injection layer may include at least one N-containing polycyclic compound containing a cyano group or an amine compound containing a carbazole group. At this time, the N-containing polycyclic compound may be 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile (HATCN). According to one example, the hole transport layer may include the compound alone or may include two or more types. According to another example, the HATCN may be deposited and used as a first hole transport layer, and the amine compound containing the carbazole group may be deposited thereon and used as a second hole transport layer.

The above-mentioned hole transport layer can play a role in facilitating hole transport. A hole transport material capable of transporting holes from the anode or hole injection layer and transferring them to the light-emitting layer, and a material with high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.

In one embodiment of the present specification, the hole transport layer may include an arylamine compound. For example, the compound may be an amine compound containing a fluorene group.

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

The electron blocking layer is a layer that prevents electrons from flowing into the anode from the light-emitting layer and controls the flow of holes flowing into the light-emitting layer, thereby controlling the performance of the entire device. The electron blocking material is preferably a compound that has the ability to prevent electrons from flowing into the anode from the light-emitting layer and control the flow of holes injected into the light-emitting layer or light-emitting material. In one embodiment, an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto.

In one embodiment of the present specification, the electron blocking layer may include an arylamine compound. In one example, the compound may be an amine compound including a dispiro[fluorene-9,9'-anthracene-10',9''-fluorene] group.

The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, a compound of the above-mentioned chemical formula 1; an 8-hydroxy-quinoline aluminum complex (Alq ₃ ); a carbazole series compound; a dimerized styryl compound; BAlq; a 10-hydroxybenzo quinoline-metal compound; compounds of the benzoxazole, benzthiazole, and benzimidazole series; a polymer of the poly(p-phenylenevinylene) (PPV) series; a spiro compound; polyfluorene, rubrene, etc.

Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compound-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compound-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

When the light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits green light, phosphorescent materials such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium), or fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as the light-emitting dopant, but is not limited thereto.

In one embodiment of the present specification, the light-emitting layer may include a compound according to the present invention as a host, and an amine-substituted pyrene compound or a polycyclic compound containing boron as a dopant. The host and the dopant may be included in an appropriate weight ratio, and in one example, the host and the dopant may be included in a weight ratio of 100:1 to 100:10, respectively.

The above hole blocking layer is a layer that blocks holes from the light-emitting layer from flowing into the cathode and controls electrons flowing into the light-emitting layer to control the performance of the entire device. The hole blocking material is preferably a compound that has the ability to prevent holes from flowing into the cathode from the light-emitting layer and control electrons injected into the light-emitting layer or light-emitting material. An appropriate material can be used as the hole blocking material depending on the composition of the organic layer used in the device. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

In one embodiment of the present specification, the hole blocking layer may include a compound having a structure in which an N-containing ring is directly connected to a spiro[fluorene-9,9'-xanthene] structure or through a linker.

The above electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, the above-mentioned compound or an Al complex of 8-hydroxyquinoline; a complex containing Alq ₃ ; an organic radical compound; and a hydroxyflavone-metal complex. The thickness of the electron transport layer may be 1 nm to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and when the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from being increased to improve electron movement due to the electron transport layer being too thick.

In one embodiment of the present specification, the electron transport layer may include a compound including an N-containing monocyclic ring, and may further include an n-type dopant or an organometallic compound. According to one example, the n-type dopant or organometallic compound may be LiQ, and the compound represented by the chemical formula 1 of the present invention and the n-type dopant (or organometallic compound) may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or light-emitting material, a compound that prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and an excellent thin film forming ability is preferable. Specific examples thereof include, but are 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.

In one embodiment of the present specification, the electron injection layer may include lithium fluoride (LiF).

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, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

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

The organic light-emitting device according to the present specification can be incorporated into and used in various electronic devices. For example, the electronic devices may be, but are not limited to, display panels, touch panels, solar modules, lighting devices, etc.

Hereinafter, examples will be provided to specifically explain the present specification. However, the embodiments described herein may be modified in various ways, and the scope of the present application is not limited to the embodiments described below. The embodiments of the present application are provided to more fully explain the present specification to those of ordinary skill in the art.

Manufacturing Example 1 (Synthesis of A1-1 to A1-6 and A2-1 to A2-4)

SM1 (1 eq) and SM2 (2 eq) were dissolved in dimethylacetamide (excess), potassium carbonate (1 eq) and copper (0.1 eq) were added, and the mixture was stirred under reflux for 12 hours.

After confirming the completion of the reaction, the mixture was cooled to room temperature, saturated sodium chloride aqueous solution (brine) was added to the reaction mixture, extracted with chloroform and water, and the solvent was removed by distillation under reduced pressure. Afterwards, the mixture was purified by column chromatography with ethyl acetate and hexane to produce the chemical formulas A1 and A2 (A1-1 to A1-6 and A2-1 to A2-4 in Table A).

A1-1 to A1-6 and A2-1 to A2-4 were synthesized in the same manner as in the synthesis method of the above chemical formulas A1 and A2, except that SM1 and SM2 were changed as follows.

Manufacturing Example 2 (Synthesis of B1 to B10)

Chemical formula A1 or A2 (1 eq) (SM1), palladium acetate (0.3 eq), and tricyclohexylphosphine (0.6 eq) synthesized in the above Preparation Example 1 were added to dimethylacetamide (excess) and stirred under reflux for 5 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, water was added, the resulting solid was filtered, the solid was dissolved in toluene and extracted, and then column chromatography was performed with ethyl acetate and hexane to prepare the chemical formula B (B1 to B10 in Table B).

B1 to B10 were synthesized using the same method as in the above chemical formula B, except that SM1 and SM2 were changed as follows.

Manufacturing Example 3 (Synthesis of Compound C1)

In the above Preparation Example 2, the chemical formula B (1 eq) (SM1) and SM2 ((1.05 eq) synthesized were added to tetrahydrofuran (excess), and then a 2 M potassium carbonate aqueous solution (30 volume ratio with respect to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, followed by heating and stirring for 10 hours. After lowering the temperature to room temperature and completing the reaction, the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the completion of the reaction, the temperature was lowered to room temperature, the solvent was removed, and the mixture was purified by recrystallization using chloroform and ethanol to prepare the chemical formula C (C1 in Table C).

The synthesis of chemical formula C (C1) in [Table C] below was carried out in the same manner except that SM1 and SM2 were changed as follows.

Manufacturing Example 4 (Synthesis of Compounds D1 to D11)

SM 1 (1 eq) and SM2 (1.3 eq), corresponding to chemical formula B and C synthesized in the above Preparation Example 2 or 3, are added to 1,4-dioxane (12 times <mass ratio> compared to SM1), potassium acetate (3 eq) is added, and stirring and reflux are performed. Palladium acetate (0.02 eq) and tricyclohexylphosphine (0.04 eq) are added after stirring in 1,4-dioxane for 5 minutes, and after confirming the completion of the reaction after 2 hours, the mixture is cooled to room temperature. After adding ethanol and water, the mixture is filtered and purified by recrystallization with ethyl acetate and ethanol to prepare the chemical formula D (D1 to D11 in Table D).

D1 to D11 were synthesized using the same method as in the above chemical formula D, except that SM1 and SM2 were changed as follows.

Manufacturing Example 5 (Synthesis of Compounds 1 to 20)

In the above Preparation Example 4, the synthesized chemical formula D (1 eq) (SM1) and SM2 (1.05 eq) were added to tetrahydrofuran (excess), and then a 2 M potassium carbonate aqueous solution (30 volume ratio with respect to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, followed by heating and stirring for 10 hours. After lowering the temperature to room temperature and completing the reaction, the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the completion of the reaction, the temperature was lowered to room temperature, the solvent was removed, and the product was purified by recrystallization using toluene to prepare compounds 1 to 20 in Table 1 below.

Compounds 1 to 20 in [Table 1] below were synthesized using the same method except that SM1 and SM2 were changed as follows.

Manufacturing Example 6 (Synthesis of Compounds 21 to 23)

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 compounds 21 to 23 of the following [Table 2].

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

Deuterium substitution for the above product was referred to Korean Patent No. 10-1538534.

<Example 1> Manufacturing of OLED

The substrate on which ITO/Ag/ITO was deposited at 70/1000/70Å as the anode was cut into 50 mm x 50 mm x 0.5 mm sizes and placed in distilled water containing a dispersant and ultrasonically cleaned. The detergent was a product of Fischer Co., and the distilled water 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, and then dried.

On the anode thus prepared, HI-1 was vacuum-deposited with a thickness of 50 Å to form a hole injection layer, and HT1, a hole transporting material, was vacuum-deposited with a thickness of 1150 Å thereon to form a hole transport layer. Next, an electron blocking layer was formed using EB1 (150 Å), and then the host compound 1 and dopant compound BD1 (2 wt% based on 100 wt% of the total of the host and dopant) synthesized in the above-described Preparation Example 5 were vacuum-deposited with a thickness of 360 Å to form a light-emitting layer. Thereafter, ET1 was deposited with a thickness of 50 Å to form a hole blocking layer, and compounds ET2 and Liq were mixed in a weight ratio of 7:3 to form an electron transport layer with a thickness of 250 Å. The device was completed by sequentially depositing 50Å thick lithium fluoride (LiF) as an electron injection layer, forming a 200Å cathode using magnesium and silver (1:4), and then depositing 600Å of CP1. During the above process, the deposition rate of the organic material was maintained at 1 Å/sec.

<Examples 2 to 28 and Comparative Examples 1 to 15>

A device was manufactured in the same manner as in Example 1, except that the compounds in Table 3 below were used instead of the above-mentioned compound 1 and compound BD1. The compounds BH1 to BH13 used in Table 3 below are as follows.

For the organic light-emitting devices manufactured in the above examples and comparative examples, the driving voltage, luminous efficiency, and color coordinates were measured at a current density of 20 mA/cm ² , and the time (T ₉₅ ) for the initial luminance to reach 95% of the current density of 20 mA/cm ² was measured. The results are shown in Table 3 below.

Experimental example
20 mA/㎠ Host dopant Voltage (V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) Color coordinates
(x,y) life
(T95, h)
(@20mA/cm ² ) Example 1 Compound 1 BD1 3.48 6.60 (0.135, 0.138) 53.8 Example 2 Compound 2 BD1 3.44 6.50 (0.134, 0.137) 55.1 Example 3 Compound 3 BD1 3.34 6.54 (0.135, 0.138) 52.5 Example 4 Compound 4 BD1 3.37 6.63 (0.134, 0.137) 54.8 Example 5 Compound 5 BD1 3.46 6.54 (0.136, 0.149) 55.9 Example 6 Compound 6 BD1 3.46 6.52 (0.135, 0.138) 56.1 Example 7 Compound 7 BD1 3.48 6.65 (0.135, 0.138) 55.8 Example 8 Compound 8 BD1 3.47 6.53 (0.134, 0.137) 55.0 Example 9 Compound 9 BD1 3.35 6.55 (0.135, 0.148) 53.4 Example 10 Compound 10 BD1 3.36 6.54 (0.134, 0.144) 53.9 Example 11 Compound 11 BD1 3.49 6.53 (0.134, 0.137) 56.1 Example 12 Compound 12 BD1 3.41 6.55 (0.134, 0.145) 53.4 Example 13 Compound 13 BD1 3.42 6.53 (0.135, 0.145) 54.7 Example 14 Compound 14 BD1 3.46 6.52 (0.134, 0.137) 55.2 Example 15 Compound 15 BD1 3.35 6.57 (0.134, 0.148) 52.9 Example 16 Compound 16 BD1 3.36 6.55 (0.134, 0.149) 53.0 Example 17 Compound 17 BD1 3.28 6.60 (0.135, 0.149) 54.2 Example 18 Compound 18 BD1 3.45 6.51 (0.135, 0.148) 55.0 Example 19 Compound 19 BD1 3.37 6.65 (0.135, 0.149) 54.9 Example 20 Compound 20 BD1 3.46 6.50 (0.134, 0.140) 56.8 Example 21 Compound 21 BD1 3.49 6.65 (0.135, 0.138) 73.8 Example 22 Compound 22 BD1 3.41 6.56 (0.134, 0.145) 70.2 Example 23 Compound 23 BD1 3.37 6.65 (0.135, 0.149) 72.7 Example 24 Compound 7 BD2 3.58 7.13 (0.133, 0.130) 49.1 Example 25 Compound 11 BD2 3.60 7.08 (0.133, 0.132) 50.5 Example 26 Compound 12 BD2 3.55 7.11 (0.134, 0.135) 48.2 Example 27 Compound 17 BD2 3.47 7.20 (0.135, 0.136)) 49.2 Example 28 Compound 20 BD2 3.48 7.09 (0.134, 0.140) 50.4 Comparative Example 1 BH1 BD1 3.81 5.32 (0.134, 0.138) 28.1 Comparative Example 2 BH2 BD1 3.80 5:30 (0.134, 0.138) 24.3 Comparative Example 3 BH3 BD1 3.79 5.20 (0.134, 0.138) 25.4 Comparative Example 4 BH4 BD1 3.80 5.21 (0.134, 0.137) 27.3 Comparative Example 5 BH5 BD1 3.83 5:30 (0.134, 0.137) 28.3 Comparative Example 6 BH6 BD1 3.85 5.33 (0.134, 0.137) 30.1 Comparative Example 7 BH7 BD1 3.79 5.38 (0.134, 0.137) 23.4 Comparative Example 8 BH8 BD1 3.87 5.24 (0.134, 0.138) 25.8 Comparative Example 9 BH9 BD1 3.81 5.66 (0.134, 0.137) 25.4 Comparative Example 10 BH10 BD1 3.80 5.28 (0.134, 0.138) 24.9 Comparative Example 11 BH11 BD1 3.72 6.01 (0.134, 0.142) 25.0 Comparative Example 12 BH12 BD1 3.79 6.00 (0.134, 0.143) 26.1 Comparative Example 13 BH13 BD1 3.74 5.31 (0.134, 0.141) 20.8 Comparative Example 14 BH1 BD2 4.01 5.60 (0.134, 0.138) 20.1 Comparative Example 15 BH2 BD2 4.00 5.61 (0.134, 0.138) 19.4

As described in Table 1 above, it can be confirmed that the organic light-emitting devices of Examples 1 to 28 using the compound represented by Chemical Formula 1 of the present invention exhibit superior characteristics in voltage, efficiency, and/or lifespan compared to Comparative Examples 1 to 15.

Specifically, the compound represented by chemical formula 1 of the present invention has a structure in which an anthracene structure is combined with an indolocarbazole structure and a 4-ring or more ring group represented by chemical formula A-1 or A-2.

On the other hand, Comparative Example 1 uses a structure in which a dibenzofuran group and an aryl group are bonded to an anthracene structure, Comparative Examples 2 to 10, 13 and 14 use a structure in which an indolocarbazole structure and an aryl group are bonded to an anthracene structure, and Comparative Example 15 uses a structure in which naphthobenzofuran and an aryl group are bonded to an anthracene structure. In addition, Comparative Examples 11 and 12 use compounds in which the 3-position of dibenzofuran is bonded to anthracene. In the case of Comparative Examples 1 to 15, it can be confirmed that the voltage, efficiency and life characteristics are significantly lowered compared to the case of using a compound in which an indolocarbazole group and a group represented by the chemical formula A-1 or A-2 are bonded simultaneously to an anthracene structure as in the present invention.

From the above results, it can be confirmed that by using the compound according to the present invention, the role of smooth hole injection into the light-emitting layer can be controlled, and excellent characteristics in terms of efficiency, driving voltage, and lifespan can be exhibited due to the balance of holes and electrons according to the chemical structure.

1: Substrate
2: Anode
3: Hole injection layer
4: Hole transport layer
5: Electron blocking layer
6: Emissive layer
7: Hole blocking layer
8: Electron transport layer
9: Electron injection layer
10: Cathode
11: Capping layer

Claims (14)

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

In the above chemical formula 1,
R1 to R4 are the same or different and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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,
L1 and L2 are the same or different, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,
Ar is represented by the following chemical formula A-1 or A-2,
[Chemical Formula A-1]

[Chemical Formula A-2]

In the above chemical formulas A-1 and A-2,
X1, Y1 and Y2 are equal to or different from each other, and are each independently O or S,
Any one of R11 to R14 and Ra is bonded to L2,
Any one of R21 to R24 and Rb is bonded to L2,
Among R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same or different, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 bond to adjacent groups to form a substituted or unsubstituted ring,
m is an integer from 1 to 4, and when m is 2 or more, 2 or more Ar are equal to or different from each other,
n1 and n2 are integers from 0 to 4, and when n1 and n2 are each 2 or more, 2 or more R1 and R2 are each equal to or different from each other,
n3 is an integer from 0 to 3, and when n3 is 2 or greater, 2 or more R3s are equal to or different from each other,
n4 is an integer from 0 to 8, and if n4 is 2 or greater, 2 or more R4s are equal to or different from each other,
n2+n3 is 0 to 6,
a and b are integers from 0 to 6, and when a and b are each 2 or greater, Ra and Rb, which are 2 or greater, are each equal to or different from each other. In claim 1, the chemical formula 1 is a compound represented by any one of the following chemical formulas 1-1 to 1-6:
[Chemical Formula 1-1]

[Chemical Formula 1-2]

[Chemical Formula 1-3]

[Chemical Formula 1-4]

[Chemical Formula 1-5]

[Chemical Formula 1-6]

In the above chemical formulas 1-1 to 1-6, the definitions of R1 to R4, L1, L2, Ar, m and n1 to n4 are the same as those in the above chemical formula 1,
n2' is an integer from 0 to 3, and when n2' is 2 or greater, 2 or more R2 are equal to or different from each other,
n3' is an integer from 0 to 2, and when n3' is 2, two R3s are equal to or different from each other. In claim 1, the chemical formula A-1 is a compound represented by any one of the following chemical formulas A-1-1 to A-1-4:
[Chemical Formula A-1-1]

[Chemical Formula A-1-2]

[Chemical Formula A-1-3]

[Chemical Formula A-1-4]

In the above chemical formulas A-1-1 to A-1-4, the definition of X1 is the same as the definition in the above chemical formula A-1,
One of R11 to R14, Ra1 to Ra4, Ra11 to Ra14, Ra21 to Ra24 and Ra31 to Ra34 is bonded to L2, and the others not bonded to L2 are the same or different, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 are bonded to adjacent groups to form a substituted or unsubstituted ring. In claim 1, the chemical formula A-2 is a compound represented by any one of the following chemical formulas A-2-1 to A-2-6:

In the above chemical formulas A-2-1 to A-2-6, the definitions of Y1 and Y2 are the same as those in the above chemical formula A-2,
One of R11 to R14, Rb1 to Rb4, Rb11 to Rb14, Rb21 to Rb24 and Rb31 to Rb34 is bonded to L2, and the others not bonded to L2 are the same or different, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted silyl group; 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 are bonded to adjacent groups to form a substituted or unsubstituted ring. A compound according to claim 1, wherein L1 and L2 are the same as or different from each other, and each independently represent a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylenylene group; a substituted or unsubstituted divalent furan group; a substituted or unsubstituted divalent benzofuran group; a substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent thiophene group; a substituted or unsubstituted divalent benzothiophene group; a substituted or unsubstituted divalent dibenzothiophene group; a substituted or unsubstituted divalent carbazole group; or a substituted or unsubstituted divalent pyridyl group. A compound according to claim 1, wherein R1 to R3 are the same as or different from each other, and each independently represents hydrogen; deuterium; i-propyl group; t-butyl group; cyclopentyl group; cyclohexyl group; phenyl group; naphthyl group; or a thiophene group unsubstituted or substituted with a phenyl group. In claim 1, R1 to R4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; an alkylsilyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium or an aryl group having 6 to 30 carbon atoms,
The above L1 and L2 are the same as or different from each other, and each independently represents a direct bond; an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or a divalent O, S or N-containing heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium.
Among the above R11 to R14, R21 to R24, Ra and Rb, the groups not bonded to L2 are the same or different, and each independently represents hydrogen; deuterium; a cyano group; an alkylsilyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; a cycloalkyl group having 3 to 30 carbon atoms substituted or unsubstituted with deuterium; an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium, or bonds to adjacent groups to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with deuterium,
The compound above m is 1. A compound according to claim 1, wherein the chemical formula 1 is substituted by at least 40% deuterium. In claim 1, the chemical formula 1 is a compound represented by any one of the following compounds:










The above compounds are substituted or unsubstituted with deuterium. An organic light-emitting device comprising an anode; a cathode; and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 9. An organic light-emitting device according to claim 10, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound. An organic light-emitting device according to claim 11, wherein the light-emitting layer comprises the compound as a host and further comprises a dopant. An organic light-emitting device according to claim 10, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises the compound. An organic light-emitting device according to claim 10, wherein the organic layer comprises an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, electron injection layer, or electron transport and injection layer comprises the compound.