KR20240061432A - Compound and organic light emitting device comprising same - Google Patents

Abstract

This specification provides a compound represented by Formula 1 and an organic light-emitting device containing the same.

Description

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

This specification relates to compounds and organic light-emitting devices containing the same.

In general, organic luminescence 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 usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may 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 this organic light-emitting device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton When it falls back to the ground state, it glows.

The development of new materials for organic light-emitting devices as described above continues to be required.

Korean Patent Publication No. 2000-0051826

This specification provides compounds and organic light-emitting devices containing the same.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Or a naphthylene group substituted or unsubstituted with deuterium,

Ar1 is represented by the following formula A,

Ar2 is an aryl group substituted or unsubstituted with deuterium or an aryl group; Or a heteroaryl group substituted or unsubstituted with deuterium or an aryl group,

[Formula A]

In Formula A,

One of R9 to R17 is connected to L1, and the remainder not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Y is O; or S,

Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In addition, an exemplary embodiment of the present specification includes an anode; cathode; and an organic light emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes the compound represented by Formula 1.

The compounds described in this specification can be used as a material for the organic layer of an organic light-emitting device. The compound according to at least one embodiment can improve efficiency, low driving voltage, and/or improve lifespan characteristics in organic light-emitting devices.

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

Hereinafter, this specification will be described in more detail.

In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.

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

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

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

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.

In one embodiment of the present specification, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group (-CN); nitro group; hydroxyl group; Alkyl group; Cycloalkyl group; Alkoxy group; Phosphine oxide group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; alkenyl group; silyl group; boron group; Amine group; Aryl group; Alternatively, it means that it is substituted with one or two or more substituents selected from the group consisting of heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

In one embodiment of the present specification, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; amino group; silyl group; boron group; Alkoxy group; Aryloxy group; Alkyl group; Cycloalkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.

In one embodiment of the present specification, the term “substituted or unsubstituted” refers to deuterium; Alkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.

In one embodiment of the present specification, the term “substituted or unsubstituted” refers to deuterium; Alkyl group; and an aryl group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.

In this specification, N% substitution with deuterium means that N% of the hydrogen available in the structure is replaced with deuterium. For example, if 25% of dibenzofuran is replaced with deuterium, it means that 2 of the 8 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 fluoro group (-F), chloro group (-Cl), bromo group (-Br), or iodo group (-I).

In the present specification, the silyl group may be represented by the formula -SiY _a Y _b Y _c , where Y _a , Y _b and Y _c are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.

In the present specification, the boron group may be represented by the chemical formula -BY _{dY e} , where Y _d and Y _e are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.

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

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

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, It may be isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto. .

Substituents containing alkyl groups, alkoxy groups, and other alkyl group moieties described in this specification include both straight-chain or branched forms.

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

In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the carbon number 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, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and adamantyl group, but is not limited thereto.

In the present specification, the amine group is -NH ₂ , and the amine group may be substituted with the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to 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 methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, and diphenylamine. group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Ditolylamine group, phenyltolylamine group, diphenylamine group, etc., but are not limited to these.

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 aryl group may be a monocyclic aryl group such as a phenyl group, biphenyl group, terphenyl group, or quarterphenyl group, but is not limited thereto. The polycyclic aryl group may include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.

(1,1,4,4-테트라메틸-1,2,3,4-테트라하이드로나프탈렌기)를 포함할 수 있으나, 이에 한정되는 것은 아니다.In the present specification, a substituted aryl group may include a structure in which an aliphatic hydrocarbon ring is condensed with an aryl group. According to one embodiment, the substituted aryl group may include a tetrahydronaphthalene group, more specifically,

It may include (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 combined with each other to form a spiro structure. At this time, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

When the fluorenyl group is substituted, , , Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited to this.

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

In the present specification, the above-described description of the alkyl group may be applied to the alkyl group among the alkylthioxy group and the alkylsulfoxy group.

In the present specification, the above-mentioned description of the aryl group may be applied to the aryl group among the arylthioxy group and the arylsulfoxy group.

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

In the present specification, the description regarding the heterocyclic group described above can be applied, except that the heteroaryl group is aromatic.

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

In the present specification, the description of the above heterocyclic group can be applied, except that the divalent heterocycle is divalent.

In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, “ring” is a hydrocarbon ring; Or refers to a heterocycle.

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

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

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

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

As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine. , thiocane, etc., but is not limited thereto.

As used herein, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, and thiazole. Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazindene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzoyl Examples include, but are not limited to, carbazole, dibenzocarbazole, phenazine, 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 forms, and the scope of the present invention is not limited to the embodiments described below.

The compound represented by Formula 1 according to the present invention increases internal quantum efficiency through the triplet-triplet fusion (TTF) mechanism of anthracene by linking anthracene to the benzene ring in the structure of Formula A containing isobenzofuran or isobenzothiophene. can help

The isobenzofuran structure and the anthracene structure each have similar triplet energy levels (T1). By introducing the isobenzofuran structure into anthracene, orbitals with similar triplet energy levels (T1) are spatially close to each other, thereby creating the TTF of anthracene. The probability of the mechanism occurring increases, and when such compounds are used in organic light-emitting devices, singlet excitons can be generated more effectively, thereby increasing fluorescence efficiency.

Additionally, when the compound represented by 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 rarely change, but the physical properties of the deuterated compound change and the vibrational energy level is lowered. Compounds substituted with deuterium can prevent a decrease in quantum efficiency due to a decrease in intermolecular van der Waals forces or collisions due to intermolecular vibrations. Additionally, C-D bonds can improve the stability of compounds.

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

Hereinafter, Chemical Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Or a naphthylene group substituted or unsubstituted with deuterium,

Ar1 is represented by the following formula A,

Ar2 is an aryl group substituted or unsubstituted with deuterium or an aryl group; Or a heteroaryl group substituted or unsubstituted with deuterium or an aryl group,

[Formula A]

In Formula A,

One of R9 to R17 is connected to L1, and the remainder not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Y is O; or S,

Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 30 carbon atoms and containing O, S or N.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 20 carbon atoms and containing O, S or N.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; Aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; An aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heteroaryl group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; Or it is deuterium.

In one embodiment of the present specification, R1 to R8 are hydrogen.

In one embodiment of the present specification, R1 to R8 are deuterium.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Or it is a naphthylene group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a phenylene group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; phenylene group; Or it is a naphthylene group.

In one embodiment of the present specification, L1 and L2 are a direct bond.

In one embodiment of the present specification, L1 is a direct bond.

In one embodiment of the present specification, L2 is a direct bond; A phenylene group substituted or unsubstituted with deuterium; Or it is a naphthylene group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, L2 is a direct bond; Or it is a phenylene group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, L1 and L2 are deuterium at 40% or more and 50% or more, respectively. It may be substituted by more than 60%, more than 70%, more than 80%, or more than 90%. In another embodiment, L1 and L2 may each be 100% substituted with deuterium.

In one embodiment of the present specification, Ar2 is an aryl group substituted or unsubstituted by deuterium or an aryl group; Or it is a heteroaryl group substituted or unsubstituted with deuterium or an aryl group.

In an exemplary embodiment of the present specification, Ar2 is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 60 carbon atoms; Or it is a heteroaryl group having 2 to 60 carbon atoms that is substituted or unsubstituted with deuterium or an aryl group having 6 to 60 carbon atoms.

In one embodiment of the present specification, Ar2 is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms; Or it is a heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with deuterium or an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar2 is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms; Or, it is a heteroaryl group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar2 is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 60 carbon atoms; Or it is a heteroaryl group containing O, S or N having 2 to 60 carbon atoms, substituted or unsubstituted with deuterium or an aryl group having 6 to 60 carbon atoms.

In one embodiment of the present specification, Ar2 is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms; Or it is a heteroaryl group containing O, S or N having 2 to 30 carbon atoms, substituted or unsubstituted with deuterium or an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar2 is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms; Or, it is a heteroaryl group containing O, S or N having 2 to 20 carbon atoms, substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar2 is an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; or a heteroaryl group having 2 to 60 carbon atoms that is unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In one embodiment of the present specification, Ar2 is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; or a heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In one embodiment of the present specification, Ar2 is an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; or a heteroaryl group having 2 to 20 carbon atoms that is unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In one embodiment of the present specification, Ar2 is an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; or an O, S or N-containing heteroaryl group having 2 to 60 carbon atoms that is substituted or unsubstituted with deuterium, phenyl group, naphthyl group or phenanthrenyl group.

In one embodiment of the present specification, Ar2 is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; or an O, S or N-containing heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with deuterium, phenyl group, naphthyl group or phenanthrenyl group.

In one embodiment of the present specification, Ar2 is an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; or an O, S or N-containing heteroaryl group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium, phenyl group, naphthyl group or phenanthrenyl group.

이고, 상기 Z1 및 Z2는 서로 같거나 상이하고, 각각 독립적으로 O 또는 S이고, 상기 기들은 중수소 및 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 상기 군에서 선택된 2 이상이 연결된 기로 치환 또는 비치환된다.In an exemplary embodiment of the present specification, Ar2 is a phenyl group; Biphenyl group; Terphenyl group; Quarterphenyl group; naphthyl group; phenanthrenyl group; fluorenyl group; Spirobifluorenyl group; Triphenylenyl group; furan group; benzofuran group; Dibenzofuran group; Naphthobenzofuran group; Dibenzofuran group in which benzofuran is condensed; thiophene group; benzothiophene group; Dibenzothiophene group; Naphthobenzothiophene group; carbazole group; or

and Z1 and Z2 are the same or different from each other, and are each independently O or S, and the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium and aryl groups, or with two or more groups selected from the group connected. .

In one embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Terphenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; a quarterphenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; A phenanthrenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; A fluorenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Spirobifluorenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; A triphenylenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; A furan group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; A benzofuran group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; A dibenzofuran group in which substituted or unsubstituted benzofuran is condensed with deuterium or an aryl group having 6 to 20 carbon atoms; A thiophene group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; A benzothiophene group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Naphthobenzothiophene group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Or it is a carbazole group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; Naphthyl group substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; Phenanthrenyl group substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; Dibenzofuran group substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; Naphthobenzofuran group substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; Or, it is a dibenzofuran group obtained by condensing benzofuran substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium or phenyl group; A phenanthrenyl group substituted or unsubstituted with deuterium; Dibenzofuran group substituted or unsubstituted with deuterium; Naphthobenzofuran group substituted or unsubstituted with deuterium; Or, it is a dibenzofuran group obtained by condensing benzofuran substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by a naphthyl group or a phenanthrenyl group; Biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Dibenzofuran group; Naphthobenzofuran group; Or it is a dibenzofuran group in which benzofuran is condensed, and the groups are substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by deuterium or a naphthyl group; Biphenyl group; naphthyl group; Dibenzofuran group; Naphthobenzofuran group; Or it is a dibenzofuran group in which benzofuran is condensed.

In one embodiment of the present specification, Ar2 is 40% or more, 50% or more of deuterium. It may be substituted by more than 60%, more than 70%, more than 80%, or more than 90%. In another embodiment, Ar2 may be 100% substituted with deuterium.

In one embodiment of the present specification, Ar1 is represented by the following formula A.

[Formula A]

In Formula A,

One of R9 to R17 is connected to L1, and the remainder not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Y is O; or S,

Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, one of R9 to R17 is connected to L1.

In one embodiment of the present specification, one of R9 to R12 is connected to L1.

In one embodiment of the present specification, one of R13 to R17 is connected to L1.

In one embodiment of the present specification, R9 is connected to L1.

In one embodiment of the present specification, R10 is connected to L1.

In one embodiment of the present specification, R11 is connected to L1.

In one embodiment of the present specification, R12 is connected to L1.

In one embodiment of the present specification, R13 is connected to L1.

In one embodiment of the present specification, R14 is connected to L1.

In one embodiment of the present specification, R15 is connected to L1.

In one embodiment of the present specification, R16 is connected to L1.

In one embodiment of the present specification, R17 is connected to L1.

In an exemplary embodiment of the present specification, the remainders of R9 to R17 that are not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, the remainders of R9 to R17 that are not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, the remainders of R9 to R17 that are not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, the remainders of R9 to R17 that are not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 30 carbon atoms and containing O, S or N.

In an exemplary embodiment of the present specification, the remainders of R9 to R17 that are not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 20 carbon atoms and containing O, S or N.

In an exemplary embodiment of the present specification, the remainders of R9 to R17 that are not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, the remainders of R9 to R17 that are not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heteroaryl group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, the remainders of R9 to R17 that are not connected to L1 are the same or different from each other, and are each independently hydrogen; Or it is deuterium.

In one embodiment of the present specification, the remainder of R9 to R17 that is not connected to L1 is hydrogen.

In one embodiment of the present specification, the remainder of R9 to R17 that is not connected to L1 is deuterium.

In one embodiment of the present specification, Y is O; Or S.

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

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

In one embodiment of the present specification, Ar1 is 40% or more, 50% or more of deuterium. It may be substituted by more than 60%, more than 70%, more than 80%, or more than 90%. In another embodiment, Ar1 may be 100% substituted with deuterium.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 60 carbon atoms and containing O, S or N.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 30 carbon atoms and containing O, S or N.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 20 carbon atoms and containing O, S or N.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 18 carbon atoms and containing O, S or N.

In one embodiment of the present specification, Ar3 is deuterium or an aryl group having 6 to 20 carbon atoms; Or, it is a heteroaryl group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar3 is an aryl group having 6 to 18 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms; Or, it is a heteroaryl group having 2 to 18 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar3 is an aryl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted quarterphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted furan group; Substituted or unsubstituted benzofuran group; Substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted benzonaphthofuran group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzonaphthothiophene group; Or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted dibenzofuran group; Or it is a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar3 is a phenyl group unsubstituted or substituted with deuterium; Or it is a naphthyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar3 is deuterium at least 40% and at least 50%. It may be substituted by more than 60%, more than 70%, more than 80%, or more than 90%. In another embodiment, Ar3 may be 100% substituted with deuterium.

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

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

The definitions of R1 to R8, L1, L2 and Ar2 are the same as those in Formula 1 above,

The definitions of Y and Ar3 are the same as those in Chemical Formula A,

R9 to R17, Ra and Rb are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a is an integer from 0 to 3,

b is an integer from 0 to 4,

When a and b are each 2 or more, 2 or more Ra and Rb are the same or different from each other, respectively.

In an exemplary embodiment of the present specification, R9 to R17, Ra, and Rb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R9 to R17, Ra, and Rb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R9 to R17, Ra, and Rb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R9 to R17, Ra, and Rb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 30 carbon atoms and containing O, S or N.

In an exemplary embodiment of the present specification, R9 to R17, Ra, and Rb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 20 carbon atoms and containing O, S or N.

In an exemplary embodiment of the present specification, R9 to R17, Ra, and Rb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R9 to R17, Ra, and Rb are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; An aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heteroaryl group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R9 to R17, Ra, and Rb are the same as or different from each other, and are each independently hydrogen; Or it is deuterium.

In an exemplary embodiment of the present specification, R9 to R17, Ra, and Rb are the same as or different from each other, and are each independently hydrogen.

In an exemplary embodiment of the present specification, R9 to R17, Ra and Rb are the same or different from each other and are each independently deuterium.

In one embodiment of the present specification, a is an integer from 0 to 3.

In one embodiment of the present specification, a is an integer of 1 to 3.

In one embodiment of the present specification, b is an integer from 0 to 4.

In one embodiment of the present specification, b is an integer from 1 to 4.

In one embodiment of the present specification, b is an integer of 1 to 3.

In one embodiment of the present specification, a is 0.

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

In one embodiment of the present specification, a is 2.

In one embodiment of the present specification, a is 3.

In one embodiment of the present specification, b is 0.

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

In one embodiment of the present specification, b is 2.

In one embodiment of the present specification, b is 3.

In one embodiment of the present specification, b is 4.

In an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 2-1 to 2-4.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4,

The definitions of R1 to R8, L1, L2 and Ar1 are the same as those in Formula 1 above,

Ar' is an aryl group substituted or unsubstituted by deuterium or an aryl group,

Z, Z1 and Z2 are the same or different from each other and are each independently O; or S,

Rc, Rd and Rf are the same or different from each other and are each independently hydrogen; heavy hydrogen; Or it is an aryl group,

c is an integer from 0 to 7,

d and f are integers from 0 to 9,

When c, d, and f are each 2 or more, 2 or more Rc, Rd, and Rf are the same or different from each other, respectively.

In an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 3-1 to 3-5.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

In Formulas 3-1 to 3-5,

The definitions of R1 to R8, L1, L2 and Ar1 are the same as those in Formula 1 above,

Ar' is an aryl group substituted or unsubstituted by deuterium or an aryl group,

Rc to Rf are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is an aryl group,

c is an integer from 0 to 7,

d to f are integers from 0 to 9,

When c to f are each 2 or more, 2 or more Rc to Rf are the same as or different from each other.

In one embodiment of the present specification, Ar' is an aryl group substituted or unsubstituted by deuterium or an aryl group.

In one embodiment of the present specification, Ar' is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 60 carbon atoms.

In one embodiment of the present specification, Ar' is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar' is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar' is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In one embodiment of the present specification, Ar' is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In one embodiment of the present specification, Ar' is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In one embodiment of the present specification, Ar' is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In one embodiment of the present specification, Ar' is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In one embodiment of the present specification, Ar' is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group.

In an exemplary embodiment of the present specification, Ar2 is a phenyl group; Biphenyl group; Terphenyl group; Quarterphenyl group; naphthyl group; phenanthrenyl group; fluorenyl group; Spirobifluorenyl group; or a triphenylenyl group, and the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium and aryl groups, or groups in which two or more groups selected from the group are connected.

In one embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Terphenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; a quarterphenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; A phenanthrenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; A fluorenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Spirobifluorenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms; Or it is a triphenylenyl group substituted or unsubstituted with deuterium or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; Naphthyl group substituted or unsubstituted with deuterium, phenyl group, naphthyl group, or phenanthrenyl group; Or it is a phenanthrenyl group substituted or unsubstituted by deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group.

In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by deuterium, a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium or phenyl group; Or it is a phenanthrenyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by a naphthyl group or a phenanthrenyl group; Biphenyl group; Or it is a naphthyl group substituted or unsubstituted with a phenyl group, and the groups are substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by deuterium or a naphthyl group; Biphenyl group; Or it is a naphthyl group.

In an exemplary embodiment of the present specification, Z, Z1, and Z2 are the same as or different from each other, and are each independently O; Or S.

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

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

In one embodiment of the present specification, Z1 is O.

In one embodiment of the present specification, Z1 is S.

In one embodiment of the present specification, Z2 is O.

In one embodiment of the present specification, Z2 is S.

In an exemplary embodiment of the present specification, Rc to Rf are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is an aryl group.

In an exemplary embodiment of the present specification, Rc to Rf are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is an aryl group having 6 to 60 carbon atoms.

In an exemplary embodiment of the present specification, Rc to Rf are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Rc to Rf are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is an aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Rc to Rf are the same as or different from each other, and are each independently hydrogen; Or it is deuterium.

In one embodiment of the present specification, Rc to Rf are hydrogen.

In one embodiment of the present specification, Rc to Rf are deuterium.

In one embodiment of the present specification, c is an integer from 0 to 7, d to f are integers from 0 to 9, and when c to f are each 2 or more, 2 or more Rc to Rf are the same or different from each other. .

In one embodiment of the present specification, c is an integer from 1 to 7, and d to f are an integer from 1 to 9.

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

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

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

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

[Formula 4-5]

[Formula 4-6]

[Formula 4-7]

In Formulas 4-1 to 4-7,

The definitions of R1 to R8, L1, L2 and Ar2 are the same as those in Formula 1 above,

The definitions of Y, Ar3, and R9 to R17 are the same as those in Formula A above.

)의 구조의 삼중항 에너지 준위(T1_a)와 화학식 A가 결합되기 전의 안트라센 구조(

)의 삼중항 에너지 준위(T1_b)의 차이는 0.1 eV 이하일 수 있다. 구체적으로 0.8 eV이하, 0.6 eV 이하, 0.5 eV 이하일 수 있다.In an exemplary embodiment of the present specification, when the lowest triplet excitation energy level (T1) is calculated using the time dependent density functional theory (TD-DFT) method of a Gaussian program (B3PW91, 6-31G*), the formula Formula A before A is bonded to L1 of Formula 1 (

) of the structure's triplet energy level (T1 _a ) and the anthracene structure before the formula A is combined (

) The difference between the triplet energy levels (T1 _b ) may be 0.1 eV or less. Specifically, it may be 0.8 eV or less, 0.6 eV or less, and 0.5 eV or less.

If the above energy level difference is satisfied, the probability of occurrence of the TTF mechanism of anthracene can be increased by placing orbitals with similar T1 energy levels close to each other spatially, and singlet excitons can be generated more effectively, thereby increasing luminous efficiency. .

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

The core structure of the compound represented by Formula 1 according to an exemplary embodiment of the present specification may be manufactured as in the method of the production example described later. Substituents may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques 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 Formula 1 above. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents into the core structure of the above structure.

Additionally, the present specification provides an organic light-emitting device containing the above-mentioned compound.

The organic light emitting device according to the present specification includes an anode; cathode; And an organic light-emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes a compound represented by the above-mentioned formula (1).

The organic light-emitting device of the present specification can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that the organic material layer is formed using the compound of Formula 1 described above.

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

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention is an organic material layer that includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, a hole injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron injection and transport layer. It can have a structure. However, the structure of the organic light emitting device of the present specification is not limited to this and may include fewer or more organic material layers.

In the organic light emitting device of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer is a compound represented by the above-mentioned formula 1. It can be included.

In the organic light emitting device of the present specification, the organic material 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 above-described formula (1).

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

In the organic light emitting device of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, an electron injection layer, or an electron injection and transport layer is a compound represented by the above-mentioned formula 1. It can be included.

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

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

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

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

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

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

At this time, the dopant is a phosphorescent material such as (4,6-F ₂ ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), PFO-based polymer, Fluorescent materials such as PPV-based polymers, anthracene-based compounds, pyrene-based compounds, boron-based compounds, etc. may be used, but are not limited to these.

In another embodiment, the organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1 described above.

In the organic light emitting device according to an exemplary embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

In one embodiment of the present specification, the thickness of the organic material layer containing the compound represented by Formula 1 is 10 Å to 500 Å, according to one example, 50 Å to 400 Å, and according to another example, 100 Å to 400 Å. It is Å.

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

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

In one embodiment of the present specification, the dopant includes an arylamine-based 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 for example, any one of the following structures may be used, but is not limited thereto.

In one embodiment of the present specification, the light-emitting layer containing the compound represented by Formula 1 has a blue color.

According to one example, the content of the compound represented by Formula 1 is 70 parts by weight to 99.99 parts by weight, based on 100 parts by weight of the sum of the host and dopant of the light emitting layer; Preferably, 80 to 99.9 parts by weight; More preferably, it is 90 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 one or more organic material layers among a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer. .

In one embodiment of the present specification, the organic light emitting device includes an anode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein at least one of the two or more organic material layers includes the compound represented by 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 injection and transport 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 injection and transport layer, an electron control layer, and a hole blocking layer.

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

Additionally, in an exemplary embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, other materials except the compound represented by Formula 1 may be the same or different from each other.

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

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 the compound represented by Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 may be included in one 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 an exemplary embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more hole transport layers, other materials except the compound represented by Formula 1 may be the same or different from each other. there is.

In one embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamine group, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1. It can be included.

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

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

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

The organic light emitting device may have, for example, a stacked structure as shown below, 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 injection and transport layer/cathode

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

Figure 1 shows 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. In this structure, the compound may be included in the light-emitting layer 6.

2 shows a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), and electron transport layer (8). , shows an example of an organic light emitting device in which the electron injection layer 9 and the cathode 10 are sequentially stacked. In this structure, the compound is 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), or an electron injection layer. It can be included in (9).

Figure 3 shows a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron injection and transport layer ( 11) and the cathode 10 are sequentially stacked. In this structure, the compound is 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), or the electron injection and transport layer (11). You can.

In one embodiment of the present specification, the electron blocking layer and the light emitting layer may be provided adjacent to each other. For example, the electron blocking layer and the light emitting layer may be provided in physical contact.

In one embodiment of the present specification, the hole transport layer and the electron blocking layer may be provided adjacent to each other. For example, the hole transport layer and the electron blocking layer may be provided in physical contact with each other.

The organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer contains the above compound, that is, the compound represented by Formula 1 above.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials. For example, the organic light emitting device according to the present specification uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to deposit a metal, a conductive metal oxide, or an alloy thereof on a substrate. Manufactured by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode on it. It can be. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

The organic material layer may have a multi-layer 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 injection and transport layer, etc., but is not limited to this and may have a single-layer structure. there is. In addition, the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.

The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to ensure smooth hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combination of metal and oxide such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

The cathode is an electrode that injects electrons, and the cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are multi-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

The hole injection layer is a layer that plays a role in smoothing the injection of holes from the anode to the light emitting layer. The hole injection material is a material that can well inject holes from the anode at a low voltage, and is the HOMO (highest occupied) of the hole injection material. It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these. 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 in preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.

In one embodiment of the present specification, the hole injection layer may include one or more N-containing polycyclic compounds 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 above compounds alone or may include two or more types of compounds. According to another example, the HATCN may be deposited and used as a first hole transport layer, and an amine compound containing the carbazole group may be deposited thereon and used as a second hole transport layer.

The hole transport layer may play a role in facilitating the transport of holes. The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

In one embodiment of the present specification, the hole transport layer may include an amine compound containing a carbazole group.

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

The electron blocking layer is a layer that prevents electrons from flowing into the anode from the light emitting layer and regulates the overall performance of the device by controlling the flow of holes flowing into the light emitting layer. The electron blocking material is preferably a compound that prevents the inflow of electrons from the light-emitting layer to the anode and has the ability to control the flow of holes injected into the light-emitting layer or the 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 amine compound containing a carbazole group. According to one example, the compound may have a carbazole group and an amine group connected to an ortho-biphenylene group.

The light-emitting layer may emit red, green, or blue light and may be made of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can emit light in the visible light range by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include the compounds of Formula 1 described above; 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.

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

When the light-emitting layer emits red light, the light-emitting dopants include PIQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium). ), phosphorescent materials such as PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these. If the light-emitting layer emits green light, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant. However, it is not limited to this. When the light-emitting layer emits blue light, the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.

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

The hole blocking layer is a layer that blocks holes from flowing into the cathode from the light-emitting layer and controls the overall performance of the device by controlling electrons flowing into the light-emitting layer. The hole blocking material is preferably a compound that prevents holes from entering the cathode from the light-emitting layer and has the ability to control electrons injected into the light-emitting layer or the light-emitting material. As a hole blocking material, an appropriate material can be used depending on the composition of the organic layer used in the device. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.

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

The electron transport layer may play a role in facilitating the transport of electrons. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include the above-mentioned compounds or Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The thickness of the electron transport layer may be 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.

In one embodiment of the present specification, the electron transport layer may include a compound containing an N-containing ring and CN, 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 Formula 1 of the present invention and the n-type dopant (or organometallic compound) are 2:8 to 8:2, for example, 4: It may be included in a weight ratio of 6 to 6:4.

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

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

Examples of the 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-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.

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

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

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

<Preparation Example 1. Synthesis of A1>

SM1 (1eq) and SM2 (1eq) were added to ethanol (excess), refluxed, and stirred for 12 hours. The temperature was lowered to room temperature, the reaction was terminated, distilled under reduced pressure to remove half of the ethanol, and then filtered to prepare Formula A1.

A1-1 to A1-6 of [Table A] were synthesized in the same manner except that SM1 and SM2 were changed as follows in the synthesis method of Chemical Formula A1.

[Table A]

<Preparation Example 2. Synthesis of A2>

SM1 (1eq, Chemical Formula A1) was dissolved in tetrahydrofuran (excess), cooled to 0 degrees, and then SM2 (Pb(OAc) ₄ ) (1eq) was slowly added and stirred for 2 hours. After filtering with Celite to remove inorganic substances, the organic solvent was removed by distillation under reduced pressure. Afterwards, the organic layer was column-columned with hexane and ethyl acetate to prepare Chemical Formula A2.

In the synthesis method of Chemical Formula A2, A2-1 to A2-6 of [Table B] were synthesized in the same manner except that SM1 was changed as follows.

[Table B]

<Preparation Example 3. Synthesis of A3-1 to A3-6>

1) Synthesis of A3-1 to A3-6

After dissolving SM1 (1eq, Chemical Formula A2) in tetrahydrofuran (excess) and cooling the temperature to 0 degrees, SM2 (3M Ar ₃ MgBr) (1eq) was added dropwise, stirred for 1 hour, and then added with 4N aq. HCl (8eq) was added. Afterwards, the reactant was warmed to room temperature and stirred for 4 hours. After completion of the reaction, the layers were separated and the solvent was removed, and the residue was subjected to silica column chromatography (ethyl acetate/hexane) to prepare A3.

The compounds in [Table C] were synthesized in the same manner except that SM1 and SM2 were changed as follows in the synthesis method of Chemical Formula A3.

[Table C]

2) Synthesis of A3-7

After dissolving A3-1 (1eq) in toluene (excess), Lawesson's reagent (1.5eq) was added, the temperature was raised to 80 degrees, and the mixture was heated and stirred for 3 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was subjected to silica column chromatography (ethyl acetate/hexane) to synthesize A3-7 (45% yield, MS[M+H]+ = 367.00).

<Preparation Example 4. Synthesis of A4>

In the above formula, X may be a halogen, and one of R9 to R17 may be represented as -X.

SM1 (1eq, Chemical Formula A3) and SM2 (1.3eq) are added to 1,4-dioxane (12 times <mass ratio> compared to SM1), and potassium acetate (3eq) is added, stirred and refluxed. Palladium acetate (0.02eq) and tricyclohexylphosphine (0.04eq) were added after stirring in 1,4-dioxane for 5 minutes, and after 10 hours, the reaction was confirmed to be complete and cooled to room temperature. Ethanol and water were added, filtered, and purified by recrystallization with ethyl acetate and ethanol to prepare Chemical Formula A4.

A4-1 to A4-7 of [Table D] were synthesized in the same manner, except that SM1 was changed as follows in the synthesis method of Chemical Formula A4.

[Table D]

<Preparation Example 5. Synthesis of Compounds 1 to 11>

SM1 (1eq, Chemical Formula A4) and SM2 (1.0eq) were added to tetrahydrofuran (excess), then 2M potassium carbonate aqueous solution (30% volume ratio compared to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added. ) was added, and then heated and stirred 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. Compounds 1 to 11 were prepared by distillation under reduced pressure to remove the organic solvent and then recrystallized with toluene.

Compounds 1 to 11 shown in Table 1 below were synthesized in the same manner except that SM1 and SM2 were changed.

SM2 in [Table 1] below was prepared according to the following scheme.

<Example 1-1> Manufacturing of OLED

As an anode, a substrate on which 70/1000/70Å ITO/Ag/ITO was deposited was cut into 50mm x 50mm x 0.5mm, placed in distilled water with a dispersant dissolved in it, and washed ultrasonically. Detergent was used from Fischer Co., and distilled water was from Millipore Co. Distilled water that was filtered secondarily was used as a filter for the product. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed in the order of isopropyl alcohol, acetone, and methanol and dried.

On the anode prepared in this way, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a hole transport material, was vacuum deposited to a thickness of 1150 Å on top of it to form a hole transport layer. Next, an electron blocking layer was formed using EB1 (150Å), and then host compound 1 and dopant BD (98% by weight: 2% by weight) synthesized in Preparation Example 5 were vacuum deposited to a thickness of 360Å. A light emitting layer was formed. Afterwards, 50Å of ET1 was deposited to form a hole blocking layer, and compounds ET2 and Liq were mixed in a ratio of 7:3 to form an electron transport layer with a thickness of 250Å. Magnesium and lithium fluoride (LiF) with a thickness of 50 Å were sequentially formed as an electron injection layer, and then 200 Å of magnesium and silver (1:4 weight ratio) were formed as a cathode, and then 600 Å of CP1 was deposited to complete the device. In the above process, the deposition rate of organic matter was maintained at 1 Å/sec.

<Example 1-2 to Example 1-11>

An organic light-emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 2 below were used instead of Compound 1.

<Comparative Examples 1-1 to 1-4>

An organic light-emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 2 below were used instead of Compound 1. The compounds BH1, BH2, BH3 and BH4 used in Table 2 below are as follows.

<Experimental Example 1>

When current was applied to the organic light-emitting devices manufactured in the above examples and comparative examples, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 2 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.

Experiment example host Voltage (V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) Color coordinates
(x,y) life span
(T95,h)
(@20mA/cm ² ) Example 1-1 Compound 1 3.44 6.74 (0.129, 0.128) 65 Example 1-2 compound 2 3.42 6.76 (0.131, 0.141) 68.5 Example 1-3 Compound 3 3.43 6.68 (0.129, 0.129) 65.4 Example 1-4 Compound 4 3.42 6.7 (0.130, 0.129) 73.7 Examples 1-5 Compound 5 3.46 6.66 (0.130, 0.128) 67.6 Example 1-6 Compound 6 3.37 6.73 (0.130, 0.134) 71.8 Example 1-7 Compound 7 3.38 6.68 (0.131, 0.134) 67.2 Examples 1-8 Compound 8 3.39 6.78 (0.131, 0.135) 65.2 Example 1-9 Compound 9 3.4 6.78 (0.132, 0.141) 66.4 Examples 1-10 Compound 10 3.43 6.65 (0.131, 0.134) 69.4 Example 1-11 Compound 11 3.49 6.75 (0.129, 0.129) 68.9 Comparative Example 1-1 BH1 3.90 5.88 (0.134, 0.139) 40.8 Comparative Example 1-2 BH2 3.75 5.42 (0.134, 0.151) 43.2 Comparative Example 1-3 BH3 3.80 5.31 (0.134, 0.138) 38.3 Comparative Example 1-4 BH4 3.78 6.01 (0.134, 0.137) 21.3

As shown in Table 2, the organic light-emitting device using the compound represented by Formula 1 according to the present invention as the light-emitting layer host showed excellent characteristics in terms of voltage, efficiency, and lifespan of the organic light-emitting device.

Specifically, the compound represented by Formula 1 is one in which a specific position of the isobenzofuran or isobenzothiophene structure is connected to the anthracene structure, and by having the above structure, it can be formed through the triplet-triplet fusion (TTF) mechanism of anthracene. It can help increase internal quantum efficiency, and it can be seen that voltage and lifespan characteristics are also improved.

On the other hand, when isobenzofuran or isobenzothiophene structures were not included as in Comparative Examples 1 to 3, it was confirmed that the TTF mechanism of anthracene did not occur and the voltage, efficiency, and lifespan characteristics were reduced.

In Comparative Example 4, although isobenzofuran is introduced into anthracene, anthracene is directly bonded to position 1 or 3 of isobenzofuran, and in this case, the two planes are perpendicular due to steric hindrance of the substituent, resulting in conjugation. It gets cut off. This reduces the chemical stability of isobenzofuran, and as a result, the voltage and efficiency of the compound are reduced, and in particular, it was confirmed that the lifespan characteristics are greatly reduced.

Therefore, it can be confirmed that the device using the compound represented by Formula 1 according to the present invention exhibits excellent characteristics in terms of driving voltage, efficiency, and lifespan through effective use of triplet excitons.

1: substrate
2: anode
3: Hole injection layer
4: Hole transport layer
5: Electronic blocking layer
6: Light-emitting layer
7: Hole blocking layer
8: Electron transport layer
9: Electron injection layer
10: cathode
11: Electron injection and transport layer

Claims (14)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Or a naphthylene group substituted or unsubstituted with deuterium,
Ar1 is represented by the following formula A,
Ar2 is an aryl group substituted or unsubstituted with deuterium or an aryl group; Or a heteroaryl group substituted or unsubstituted with deuterium or an aryl group,
[Formula A]

In Formula A,
One of R9 to R17 is connected to L1, and the remainder not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Y is O; or S,
Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. In claim 1,
The compound of Formula 1 is represented by the following Formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
The definitions of R1 to R8, L1, L2 and Ar2 are the same as those in Formula 1 above,
The definitions of Y and Ar3 are the same as those in Chemical Formula A,
R9 to R17, Ra and Rb are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a is an integer from 0 to 3,
b is an integer from 0 to 4,
When a and b are each 2 or more, 2 or more Ra and Rb are the same or different from each other, respectively. In claim 1,
Ar2 is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium or an aryl group having 6 to 30 carbon atoms; Or a compound that is a heteroaryl group containing O, S or N of 2 to 30 carbon atoms substituted or unsubstituted with deuterium or an aryl group of 6 to 30 carbon atoms. In claim 1,
Formula 1 is a compound represented by any one of the following formulas 2-1 to 2-4:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4,
The definitions of R1 to R8, L1, L2 and Ar1 are the same as those in Formula 1 above,
Ar' is an aryl group substituted or unsubstituted with deuterium or an aryl group,
Z, Z1 and Z2 are the same or different from each other and are each independently O; or S,
Rc, Rd and Rf are the same or different from each other and are each independently hydrogen; heavy hydrogen; Or it is an aryl group,
c is an integer from 0 to 7,
d and f are integers from 0 to 9,
When c, d, and f are each 2 or more, 2 or more Rc, Rd, and Rf are the same as or different from each other, respectively. In claim 1,
Ar3 is a substituted or unsubstituted phenyl group; Or a compound that is a substituted or unsubstituted naphthyl group. In claim 1,
R1 to R8 are the same as or different from each other, and are each independently hydrogen; Or a compound that is deuterium. In claim 1,
R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; Aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium,
Ar2 is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium or an aryl group having 6 to 30 carbon atoms; or an O, S or N-containing heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted with deuterium or an aryl group having 6 to 30 carbon atoms,
Among R9 to R17, the remainder not connected to L1 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; or an O, S or N-containing heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with deuterium,
Ar3 is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium; Or a compound that is a heteroaryl group containing O, S or N having 2 to 30 carbon atoms substituted or unsubstituted with deuterium. In claim 1,
One of R9 to R17 is connected to L1, and the remainder not connected to L1 are the same or different from each other, and are each independently hydrogen; Or a compound that is deuterium. In claim 1,
The compound of Formula 1 includes at least one deuterium. In claim 1,
Formula 1 is a compound represented by any one of the following compounds:

. anode; cathode; and an organic light-emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 10. In claim 11,
An organic light-emitting device wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound. In claim 12,
An organic light emitting device wherein the light emitting layer includes the compound as a host and further includes a dopant. In claim 11,
The organic material layer further includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer. .

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