KR102361786B1 - Heterocyclic compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification relates to a compound represented by Formula 1 and an organic light emitting device including the same.

Description

Heterocyclic compound and organic light emitting device comprising the same {HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0004686 filed with the Korean Intellectual Property Office on January 14, 2019, the entire contents of which are incorporated herein by reference.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

The development of new materials for the organic light emitting device as described above is continuously required.

International Patent Application Publication No. 2003-012890

An object of the present specification is to provide a heterocyclic compound and an organic light emitting device including the same.

The present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; And one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group or a substituent in which two or more substituents are connected, or adjacent substituents combine to form a ring,

R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

m is 0 or 1, n is 0 or 1,

The value of m+n is 1,

r1 is an integer from 0 to 5, r2 is an integer from 0 to 3, r3 is an integer from 0 to 2,

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

When r2 is 2 or more, R2 are the same as or different from each other,

When r3 is 2, R3 is the same as or different from each other.

In addition, the present specification is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

The compound according to an exemplary embodiment of the present specification may be used in an organic light emitting device, thereby lowering the driving voltage of the organic light emitting device and improving light efficiency. In addition, the lifespan characteristics of the device can be improved by the thermal stability of the compound.

The compound according to an exemplary embodiment of the present specification is an organic material suitable for a deposition device.

1 to 3 show examples of an organic light emitting device according to an exemplary embodiment of the present specification.
Figure 4 shows the TGA analysis of Compound A-2 according to an embodiment of the present specification.
5 shows the TGA analysis of comparative compound X-7.

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

The compound represented by Formula 1 has a core structure in which benzofuran is condensed with naphthobenzofuran. When two arylamine groups are connected to the core structure and used as a dopant in the light emitting layer of an organic light emitting device, it has characteristics of long life and high efficiency.

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

는 연결되는 부위를 의미한다.In this specification,

means the part to be connected.

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; an alkyl group; cycloalkyl group; amine group; silyl group; a phosphine oxide group; aryl group; and 1 or 2 or more substituents selected from the group consisting of a heteroaryl group containing at least one of N, O, S and Si atoms, or is substituted with a substituent to which two or more of the above exemplified substituents are linked, or any substituent It also means not having

또는

의 치환기가 될 수 있다. In the present specification, that two or more substituents are connected means that the hydrogen of any one substituent is connected with the other substituent. For example, an isopropyl group and a phenyl group are linked

or

It can be a substituent of

또는

의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 것과 동일하게 적용된다.In the present specification, three substituents are connected to (substituent 1)-(substituent 2)-(substituent 3) as well as consecutively connected (substituent 1) to (substituent 2) and (substituent 3) It also includes connecting. For example, two phenyl groups and an isopropyl group are linked

or

It can be a substituent of The same applies to those in which 4 or more substituents are connected.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but 1 to 30; 1 to 20; 1 to 10; Or 1 to 5 are preferable. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1 -Dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but has 3 to 30 carbon atoms; 3 to 20 carbon atoms; 3 to 10 carbon atoms; or preferably having 3 to 6 carbon atoms, specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -SiR ₂₀₁ R ₂₀₂ R ₂₀₃ , R ₂₀₁ to R ₂₀₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, methyldiphenylsilyl group, t- butyldiphenylsilyl group, phenylsilyl group, and the like, but is not limited thereto.

In the present specification, the aryl group means a monovalent group of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. In the present specification, the aromatic hydrocarbon refers to a compound in which pi electrons are completely conjugated and includes a planar ring, and the group derived from the aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon. . Also, in the present specification, the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other. The aryl group is not particularly limited, but has 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or it is preferably 6 to 13, and the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

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

In the present specification, when it is said that the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which the substituents of the pentacyclic ring of fluorene are spiro-bonded with each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group includes one or more atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic group may include one or more atoms selected from the group consisting of O, N and S. Although the number of carbon atoms is not particularly limited, 2 to 50 carbon atoms; 2 to 30; 2 to 20; 2 to 18; Or 2 to 13 are preferable. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzoxa Zol group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthroline group, thiazole group, isoxazole group, oxadiazole group, thia diazole group, benzothiazole group, phenothiazine group, dibenzofuran group, dihydrophenothiazine group, dihydrobenzoisoquinoline group, chromene group, and the like, but is not limited thereto.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of an aromatic and aliphatic group, and may be selected from examples of the heterocyclic group.

In the present specification, the heteroaryl group refers to a monovalent aromatic heterocyclic ring. Here, the aromatic heterocyclic ring is a monovalent group of an aromatic ring or a derivative of an aromatic ring, and refers to a group including at least one of N, O and S as heteroatoms in the ring. The aromatic ring derivative includes all structures in which an aromatic ring or an aliphatic ring is condensed on an aromatic ring. In addition, in the present specification, the heteroaryl group is intended to include a monovalent group in which an aromatic ring containing two or more heteroatoms or a derivative of an aromatic ring containing heteroatoms is connected to each other. the heteroaryl group having 2 to 50 carbon atoms; 2 to 30; 2 to 20; 2 to 18; Or 2 to 13 are preferable.

In the present specification, the phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthyl phosphine oxide, and the like.

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

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

As used herein, the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.

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

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from among the examples of the aryl group except for those that are not monovalent.

Hereinafter, the compound represented by Formula 1 will be described in detail.

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

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

In the exemplary embodiment of the present specification, the value of m+n is 1.

In the present specification, when m or n is 0, the -O- bond does not exist between the two benzene rings and the two benzene rings are not connected.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; And one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group or a substituent to which two or more substituents are connected, or adjacent substituents combine to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C 3 to C 30 cycloalkyl group; a substituted or unsubstituted silyl group having 1 to 30 carbon atoms; a substituted or unsubstituted C6-C30 aryl group; And one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituent in which two or more substituents are connected, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring having 2 to 30 carbon atoms .

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; cycloalkyl group; a silyl group unsubstituted or substituted with an alkyl group or an aryl group; an aryl group unsubstituted or substituted with deuterium, a halogen group, an alkyl group, or a haloalkyl group; And one substituent selected from the group consisting of a heterocyclic group substituted or unsubstituted with an alkyl group or a substituent to which two or more substituents are connected, or adjacent substituents combine to form a ring substituted or unsubstituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently substituted with deuterium, a halogen group, an alkyl group, an alkyl group substituted with deuterium, a cycloalkyl group, a silyl group substituted with an alkyl group or an aryl group, an alkyl group Or an unsubstituted arylamine group, or an aryl group unsubstituted or substituted with an O or S-containing heterocyclic group; Or a heterocyclic group substituted or unsubstituted with an alkyl group, or adjacent substituents combine to form a carbazole ring substituted or unsubstituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a silyl group, an amine group and 2 carbon atoms to 20 O or S-containing heterocyclic group, a C 6 to C 20 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of or two or more substituents connected thereto; Or a C 2 to C 20 or S-containing heterocyclic group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms,

Ar1 and Ar2 are a phenyl group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms, combine with each other to form a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms, Ar3 and Ar4 are a phenyl group having 1 to 6 carbon atoms A phenyl group substituted or unsubstituted with an alkyl group, and combined with each other to form a carbazole ring substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; an alkyl group; cycloalkyl group; silyl group; amine group; and an aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of O or S-containing heterocyclic groups or a substituent to which two or more substituents are connected.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; an alkyl group having 1 to 10 carbon atoms; a cycloalkyl group having 3 to 30 carbon atoms; silyl group; amine group; It is an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of O or S-containing heterocyclic groups having 2 to 30 carbon atoms or a substituent to which two or more substituents are connected.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; an alkyl group having 1 to 6 carbon atoms; a cycloalkyl group having 3 to 20 carbon atoms; silyl group; amine group; and an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with one or more substituents selected from the group consisting of O or S-containing heterocyclic groups having 2 to 20 carbon atoms or a substituent to which two or more substituents are connected.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; an alkyl group unsubstituted or substituted with deuterium or a halogen group; cycloalkyl group; a silyl group unsubstituted or substituted with an alkyl group or an aryl group; an arylamine group unsubstituted or substituted with an alkyl group; It is an aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of O or S-containing heterocyclic groups.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium or a halogen group; a cycloalkyl group having 3 to 60 carbon atoms; a silyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 3 to 60 carbon atoms; an arylamine group having 6 to 90 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; It is an aryl group having 3 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of O or S-containing heterocyclic groups having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium or a halogen group; a cycloalkyl group having 3 to 30 carbon atoms; a silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 3 to 30 carbon atoms; an arylamine group having 6 to 60 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; and an aryl group having 3 to 30 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of an O or S-containing heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; an alkyl group having 1 to 6 carbon atoms that is unsubstituted or substituted with deuterium or a halogen group; a cycloalkyl group having 3 to 20 carbon atoms; a silyl group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 3 to 20 carbon atoms; an arylamine group having 6 to 40 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; and an aryl group having 3 to 20 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of an O or S-containing heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium or a halogen group; a cycloalkyl group having 3 to 30 carbon atoms; a silyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 3 to 30 carbon atoms; and an aryl group having 3 to 30 carbon atoms that is unsubstituted or substituted with one or more substituents selected from the group consisting of an arylamine group having 6 to 60 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; an alkyl group having 1 to 6 carbon atoms that is unsubstituted or substituted with deuterium or a halogen group; a cycloalkyl group having 3 to 20 carbon atoms; and an aryl group having 3 to 20 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of a silyl group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium; halogen group; methyl group; isopropyl group; t-butyl group; cyclohexyl group; trimethylsilyl group; triethylsilyl group; triphenylsilyl group; t-butyldiphenylsilyl group; t-butyldimethylsilyl group; methyldiphenylsilyl group; bistolylamine group; and an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with one or more substituents selected from the group consisting of a benzothiophene group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a phenyl group; biphenyl group; naphthyl group; or a phenanthrenyl group, and the phenyl group, biphenyl group, naphthyl group or phenanthrenyl group is deuterium; halogen group; methyl group; CD ₃ ; CF ₃ ; isopropyl group; t-butyl group; cyclohexyl group; trimethylsilyl group; triethylsilyl group; triphenylsilyl group; t-butyldiphenylsilyl group; t-butyldimethylsilyl group; methyldiphenylsilyl group; And it is unsubstituted or substituted with one or more substituents selected from the group consisting of a bistolylamine group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently represents a C 2 to C 30 heterocyclic group unsubstituted or substituted with an alkyl group having 1 to 10 C atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently represents an O or S-containing heterocyclic group having 2 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a dibenzofuran group unsubstituted or substituted with a methyl group or t-butyl group; dibenzothiophene group; or a naphthobenzofuran group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently represents a dibenzofuran group unsubstituted or substituted with a methyl group or a t-butyl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are bonded to each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are bonded to each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are phenyl groups unsubstituted or substituted with an alkyl group, and combine with each other to form a carbazole ring substituted or unsubstituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are phenyl groups substituted or unsubstituted with an alkyl group, and combine with each other to form a carbazole ring substituted or unsubstituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are phenyl groups unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms, and combine with each other to form a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are phenyl groups unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms, and combine with each other to form a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are a phenyl group unsubstituted or substituted with a methyl group or a t-butyl group, and combine with each other to form a carbazole ring unsubstituted or substituted with a methyl group or a t-butyl group.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are a phenyl group unsubstituted or substituted with a methyl group or a t-butyl group, and combine with each other to form a carbazole ring unsubstituted or substituted with a methyl group or a t-butyl group.

In an exemplary embodiment of the present specification, Ar1 and Ar3 are the same as or different from each other.

In an exemplary embodiment of the present specification, Ar2 and Ar4 are the same as or different from each other.

In an exemplary embodiment of the present specification, Ar1 and Ar3 are the same.

In an exemplary embodiment of the present specification, Ar2 and Ar4 are the same.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; an amine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; an amine group unsubstituted or substituted with an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted C 1 to C 5 alkyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R1 to R3 are hydrogen.

In an exemplary embodiment of the present specification, r1 is an integer of 0 to 5, r2 is an integer of 0 to 3, r3 is an integer of 0 to 2, and when r1 is 2 or more, R1 is the same as or different from each other, r2 When is 2 or more, R2 is the same as or different from each other, and when r3 is 2, R3 is the same or different from each other.

In an exemplary embodiment of the present specification, r1 is 0.

In the exemplary embodiment of the present specification, r2 is 0.

In one embodiment of the present specification, r3 is 0.

In an exemplary embodiment of the present specification, -N(Ar1)(Ar2) and -N(Ar3)(Ar4) of Formula 1 are the same as or different from each other.

In the exemplary embodiment of the present specification, -N(Ar1)(Ar2) and -N(Ar3)(Ar4) of Formula 1 are the same.

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

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,

Ar1 to Ar4, R1 to R3, and r1 to r3 have the same definitions as in Formula 1.

In the exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 4-1 or 4-2.

[Formula 4-1]

[Formula 4-2]

In Formulas 4-1 and 4-2,

Ar1 to Ar4, R1 to R3, and r1 to r3 have the same definitions as in Formula 1.

In the exemplary embodiment of the present specification, Chemical Formula 2-1 is represented by Chemical Formula 4-1.

In the exemplary embodiment of the present specification, Chemical Formula 2-2 is represented by Chemical Formula 4-2.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-8.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

In Formulas 3-1 to 3-8,

Ar1 to Ar4, R1 to R3, and r1 to r3 have the same definitions as in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 2-1 is represented by any one of Chemical Formulas 3-1 to 3-4.

In an exemplary embodiment of the present specification, Chemical Formula 2-2 is represented by any one of Chemical Formulas 3-5 to 3-8.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 5-1 to 5-8.

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

[Formula 5-5]

[Formula 5-6]

[Formula 5-7]

[Formula 5-8]

In Formulas 5-1 to 5-8,

Ar1 to Ar4, R1 to R3, and r1 to r3 have the same definitions as in Formula 1.

In the exemplary embodiment of the present specification, Chemical Formula 2-1 is represented by any one of Chemical Formulas 5-1 to 5-4.

In an exemplary embodiment of the present specification, Chemical Formula 2-2 is represented by any one of Chemical Formulas 5-5 to 5-8.

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

In an exemplary embodiment of the present specification, Chemical Formula 4-2 is represented by any one of Chemical Formulas 5-5 to 5-8.

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

The compound according to an exemplary embodiment of the present specification may be prepared by a method described below. If necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, etc. can be changed.

For example, the compound represented by Formula 1 may have a core structure as shown in Formula 1 below. 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. A substituent may be bonded as in the following general formula 1, but is not limited thereto.

[General formula 1]

In Formula 1, the definitions of Ar1 to Ar4 are the same as defined in Formula 1 above. Although R1 to R3 are not represented in Formula 1, a desired compound can be obtained by using a reactant in which R1 to R3 is substituted or by substituting R1 to R3 using a method known to the compound prepared above.

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

The present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, the maximum emission peak of the emission layer including the compound represented by Formula 1 is 400 nm to 500 nm. That is, the light emitting layer including the compound represented by Formula 1 emits blue light.

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

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

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

In the present specification, the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.

In the present specification, the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more layers C and one or more layers D, respectively.

The organic light emitting device according to the present specification may include an additional organic material layer in addition to the light emitting layer.

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

The organic light emitting diode according to an exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 and a compound represented by Formula H below.

[Formula H]

In the formula (H),

L21 and L22 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms including N, O, or S.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; an arylene group having 6 to 20 carbon atoms; or a heteroarylene group having 2 to 20 carbon atoms including N, O, or S. The arylene group or heteroarylene group is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms. In another exemplary embodiment, the 'substituted or unsubstituted' is substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms or does not have any substituents. .

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted divalent thiophene group.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; phenylene group; naphthylene group; or a divalent thiophene group.

In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; phenylene group; or a naphthylene group.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with Y1; or a C 2 to C 30 heteroaryl group unsubstituted or substituted with Y 1 .

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a monocyclic to 4-ring aryl group unsubstituted or substituted with Y1; or a monocyclic to 4-ring heteroaryl group unsubstituted or substituted with Y1.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with Y1; a biphenyl group unsubstituted or substituted with Y1; a terphenyl group unsubstituted or substituted with Y1; a naphthyl group unsubstituted or substituted with Y1; an anthracene group unsubstituted or substituted with Y1; a phenanthrene group unsubstituted or substituted with Y1; Y1 a substituted or unsubstituted phenalene group; a fluorenyl group substituted or unsubstituted with Y1; Y1 a substituted or unsubstituted benzofluorenyl group; a furan group unsubstituted or substituted with Y1; a thiophene group substituted or unsubstituted with Y1; a carbazole group unsubstituted or substituted with Y1; a benzocarbazole group substituted or unsubstituted with Y1; a dibenzofuran group substituted or unsubstituted with Y1; a naphthobenzofuran group unsubstituted or substituted with Y1; Y1 a substituted or unsubstituted dibenzothiophene group; Y1 a substituted or unsubstituted naphthobenzothiophene group; a pyridine group unsubstituted or substituted with Y1; a pyrimidine group unsubstituted or substituted with Y1; A triazine group unsubstituted or substituted with Y1; Y1 a substituted or unsubstituted quinoline group; Y1 a substituted or unsubstituted isoquinoline group; or an indolo[3,2,1-jk]carbazole group substituted or unsubstituted with Y1.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with Y1; a biphenyl group unsubstituted or substituted with Y1; a naphthylene group unsubstituted or substituted with Y1; anthracene group; phenanthrene group; phenalene group; a thiophene group substituted or unsubstituted with Y1; dibenzofuran group; dibenzothiophene group; naphthobenzofuran group; pyridine group; isoquinoline group; or an indolo[3,2,1-jk]carbazole group.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; or an O-containing heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; biphenyl group; 1-naphthyl group; 2-naphthyl group; dibenzofuran group; or a naphthobenzofuran group.

In an exemplary embodiment of the present specification, Y1 is deuterium; halogen group; nitrile group; an alkyl group having 1 to 10 carbon atoms; a cycloalkyl group having 3 to 20 carbon atoms; a silyl group substituted with an alkyl group having 1 to 10 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Y1 is deuterium; halogen group; nitrile group; methyl group; cyclohexyl group; trimethylsilyl group; or a phenyl group.

In an exemplary embodiment of the present specification, Y1 is deuterium; fluorine; nitrile group; methyl group; cyclohexyl group; or a trimethylsilyl group.

In an exemplary embodiment of the present specification, R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 10 alkyl group; a substituted or unsubstituted C 3 to C 20 cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R21 to R28 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, 4 or more of R21 to R28 are deuterium, and the remainder is hydrogen.

In an exemplary embodiment of the present specification, R21 to R28 are deuterium.

In an exemplary embodiment of the present specification, R21 to R28 are hydrogen.

In an exemplary embodiment of the present specification, Formula H includes at least one or more deuterium.

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

The organic light emitting device according to an exemplary embodiment of the present specification includes an emission layer, the emission layer includes the compound represented by Formula 1 as a dopant of the emission layer, and the compound represented by Formula H as a host of the emission layer.

In an exemplary embodiment of the present specification, based on 100 parts by weight of the compound represented by Formula H, the content of the compound represented by Formula 1 is 0.01 parts by weight to 30 parts by weight; 0.1 parts by weight to 20 parts by weight; or 0.5 to 10 parts by weight.

In the exemplary embodiment of the present specification, the light emitting layer may further include one host material in addition to the compound represented by Formula H. In this case, the host material (mixed host compound) further included may be a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

The mixing ratio of the compound represented by Formula H and the mixed host compound is 95:5 to 5:95.

In an exemplary embodiment of the present specification, the light emitting layer including the compound represented by Formula 1 and the compound represented by Formula H has a blue color.

The organic light emitting device according to an exemplary embodiment of the present specification includes two or more light emitting layers, and at least one of the two or more light emitting layers includes a compound represented by Formula 1 and a compound represented by Formula H. The light emitting layer including the compound represented by Formula 1 and the compound represented by Formula H is blue, and the light emitting layer not including the compound represented by Formula 1 and the compound represented by Formula H is blue, known in the art; It may include a red or green light emitting compound.

In the exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer.

In an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer or an electron transport layer.

In an exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer.

In an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer.

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

In an exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; a second electrode provided to face the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.

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

In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

In the exemplary embodiment of the present specification, the first electrode is a cathode, and the second electrode is an anode.

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

For example, the structure of an organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3 . 1 to 3 illustrate an organic light emitting device, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which an anode 102, a light emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101. As shown in FIG. The compound represented by Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by Formula H may be further included in the emission layer.

2 illustrates a structure of an organic light emitting device in which an anode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101. According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by Formula H may be further included in the emission layer. According to another exemplary embodiment, the compound represented by Formula 1 is included in the hole injection layer or the hole transport layer.

3 shows an anode 102 , a hole injection layer 103 , a hole transport layer 104 , an electron blocking layer 105 , a light emitting layer 106 , a hole blocking layer 107 , and an electron transport layer 108 on a substrate 101 . , the structure of the organic light emitting device in which the electron injection layer 109 and the cathode 110 are sequentially stacked is exemplified. According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is included in the light emitting layer. According to an exemplary embodiment of the present specification, the compound represented by Formula H may be further included in the emission layer. According to another exemplary embodiment, the compound represented by Formula 1 is included in the hole injection layer, the hole transport layer, the electron blocking layer, the hole blocking layer, the electron transport layer, or the electron injection layer.

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that the light emitting layer includes the compound, that is, the compound represented by Formula 1 and the compound represented by Formula H.

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

In addition, the compound represented by Formula 1 or the compound represented by Formula H 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 coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

The organic light emitting device according to the present specification may include an additional light emitting layer other than the light emitting layer including the compound represented by Formula 1 or the compound represented by Formula H. The additional light emitting layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material excellent in the ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material, metal porphyrin (porphyrin), oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material, as used in accordance with the prior art. In particular, suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.

The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injecting material has excellent electron transport ability and has an electron receiving effect from the second electrode and an excellent electron injecting effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

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

The electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer. A known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer or between the light emitting layer and the layer that simultaneously injects and transports holes.

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

The organic light emitting device according to the present specification may be a top emission type, a back emission type, or a double side emission type depending on the material used.

Hereinafter, in order to describe the present specification in detail, it will be described in detail with reference to Examples and Comparative Examples. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the Examples and Comparative Examples described below. Examples and comparative examples of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

Synthesis example

Synthesis Example 1. Synthesis of Intermediate S-3

In a nitrogen atmosphere, 60 g of compound S-1, 62.8 g of compound S-2, 43.5 g of potassium carbonate, 600 mL of dioxane and 150 mL of water were added, and then tetrakis (triphenylphosphine) palladium (0) ( After adding 2.1 g of Pd(PPh ₃ ) ₄ ), the mixture was heated at 120° C. and stirred for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the mixture, and the mixture was treated with MgSO ₄ (anhydrous) and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (ethylacetate/hexane) to obtain 63.5 g of intermediate S-3. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=379.

Synthesis Example 2. Synthesis of intermediate S-5

In a nitrogen atmosphere, 61 g of intermediate S-3 and 55.6 g of potassium carbonate were placed in 550 mL of N-dimethylformamide and stirred at 160° C. for 2 hours to synthesize intermediate S-4. After completion of the reaction, the reaction solution was cooled to room temperature, and 63 g of perfluorobutanesulfonyl fluoride was immediately added and stirred for 1 hour. After the reaction was completed, water and ethyl acetate were added to separate the mixture, followed by MgSO ₄ (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 52 g of intermediate S-5.

Synthesis Example 3. Synthesis of Intermediate S-7

In the same manner as for synthesizing Intermediate S-3 in Synthesis Example 1., 20 g of S-1 was used to obtain Intermediate S-7 (20.3 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=379.

Synthesis Example 4. Synthesis of Intermediate S-10

In the same manner as for synthesizing intermediate S-5 in Synthesis Example 2., 18 g of S-7 was used to obtain intermediate S-10 (15.5 g).

Synthesis Example 5. Synthesis of compound A-2

In a nitrogen atmosphere, 20 mL of xylene was added to 3 g of intermediate S-5, 2.8 g of N-1 and 3.5 g of potassium phosphate, and bis (dibenzylideneacetone) palladium (0) (Bis (dibenzylideneacetone) palladium (0) )) 0.09 g and 0.13 g of Xphos are dissolved in xylene and slowly added dropwise to the reaction solution. The reaction solution is 140 It was heated at ℃ and stirred for 24 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water and NaCl solution were added to separate the mixture, and then, MgSO ₄ (anhydrous) was treated and filtered. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain Compound A-2 (2.6 g). As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=867.

Synthesis Example 6. Synthesis of compound A-3

Compound A-3 (2.7 g) was obtained in the same manner as for synthesizing Compound A-2 in Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=935.

Synthesis Example 7. Synthesis of compound A-4

Compound A-4 (2.4 g) was obtained in the same manner as for synthesizing Compound A-2 in Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=1011.

Synthesis Example 8. Synthesis of compound A-5

Compound A-5 (1.9 g) was obtained in the same manner as for synthesizing Compound A-2 in Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=1043.

Synthesis Example 9. Synthesis of compound A-6

Compound A-6 (2.8 g) was obtained in the same manner as for synthesizing Compound A-2 in Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=991.

Synthesis Example 10. Synthesis of compound A-7

Compound A-7 (3.0 g) was obtained in the same manner as for synthesizing Compound A-2 in Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=970.

Synthesis Example 11. Synthesis of compound C-1

Compound C-1 (3.5 g) was obtained by using 4 g of intermediate S-10 in the same manner as for synthesizing compound A-2 of Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=1048.

Synthesis Example 12. Synthesis of Intermediate S-14

Method for synthesizing the intermediate S-3 of Synthesis Example 1. and the method of synthesizing the intermediate S-5 of Synthesis Example 2. In the same manner, 40 g of S-1 was used to obtain an intermediate S-14 (34 g).

Synthesis Example 13. Synthesis of intermediate S-17

Method for synthesizing the intermediate S-3 of Synthesis Example 1. and the method for synthesizing the intermediate S-5 of Synthesis Example 2. In the same manner, 20 g of S-1 was used to obtain an intermediate S-17 (8 g).

Synthesis Example 14. Synthesis of compound B-2

Compound B-2 (2.7 g) was obtained by using 3 g of intermediate S-14 in the same manner as for synthesizing compound A-2 in Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=947.

Synthesis Example 15. Synthesis of compound B-3

Compound B-3 (2.4 g) was obtained by using 3 g of intermediate S-14 in the same manner as for synthesizing compound A-2 of Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=811.

Synthesis Example 16. Synthesis of compound B-4

Compound B-4 (3.1 g) was obtained by using 3 g of intermediate S-14 in the same manner as for synthesizing compound A-2 of Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=1193.

Synthesis Example 17. Synthesis of compound B-5

Compound B-5 (2.6 g) was obtained by using 3 g of intermediate S-14 in the same manner as for synthesizing compound A-2 of Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=1019.

Synthesis Example 18. Synthesis of compound B-6

Compound B-6 (2.5 g) was obtained by using 3 g of intermediate S-14 in the same manner as for synthesizing compound A-2 in Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=1061.

Synthesis Example 19. Synthesis of compound B-7

Compound B-7 (2.2 g) was obtained using 3 g of intermediate S-14 in the same manner as for synthesizing compound A-2 of Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=863.

Synthesis Example 20. Synthesis of compound D-1

Compound D-1 (1.7 g) was obtained by using 3 g of intermediate S-17 in the same manner as for synthesizing compound A-2 of Synthesis Example 5. As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M+H+]=726.32.

Experimental Example 1

Examples 1 to 2.

The compound was HOMO in the absorption state of the molecule using the TD-DFT (B3LYP) method/6-31G* basis method. The energy level of LUMO and singlet(S ₁ ) and oscillator strength (radiation transition probability, f) of singlet were calculated. The calculation results are shown in Table 1 below.

Comparative Example 1 Comparative Example 2 Example 1 Example 2 compound X-1 compound X-2 Compound A-1 compound B-1 HOMO 5.37 5.38 4.78 4.79 LUMO 1.43 1.64 1.57 1.47 S ₁ 3.60 3.44 2.84 2.94 f 0.343 0.042 1.32 1.12

The emission wavelength of the compound is a value shifted by the Stokes shift from the absorption wavelength, and the degree of emission wavelength can be predicted from the absorption wavelength.

The radiation transition probability (f) is a measure indicating the fluorescence quantum efficiency and is calculated by the following equation. The greater the radiation transition probability (f), the greater the luminous efficiency.

The radiation transition probability (f) of Comparative Examples 1 and 2 was very small compared to the compounds A-1 and B-1 of Examples 1 and 2, and as a result, the device containing the compounds X-1 to X-2 It can be expected that the efficiency will be very low. In addition, the emission wavelength can be predicted from the singlet energy value of Compound X-1, and since it has a very short wavelength compared to the compounds of Examples, the efficiency of the device is expected to be very low when used as a blue dopant in the emission layer, so it is called an appropriate blue dopant. Can not.

Therefore, the luminous efficiency of compounds A-1 and B-1 is higher than that of compounds X-1 and X-2, and the efficiency of the blue light emitting device is also increased.

Experimental Example 2: Device Example

Example 3.

A glass substrate coated with indium tin oxide (ITO) to a thickness of 150 nm was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following compound HAT was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. The following compound HT-A was vacuum deposited thereon to form a first hole transport layer with a thickness of 100 nm, and then the compound HT-B was vacuum deposited to form a second hole transport layer with a thickness of 10 nm. On the second hole transport layer, compound BH-A as a host and compound A-2 as dopant were vacuum-deposited at a weight ratio of 96:4 to form a light emitting layer with a thickness of 20 nm.

Then, the following compound ET-A and compound Liq were deposited in a weight ratio of 1:1 to form a 30 nm electron injection and transport layer. On this, silver (Ag) and magnesium (Mg) were deposited in a weight ratio of 9:1 to a thickness of 15 nm, and aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting diode.

In the above process, the deposition rate of the organic material was maintained at 0.1 nm/sec, the deposition rate of 0.02 nm/sec for LiF and 0.3 nm/sec to 0.7 nm/sec for aluminum was maintained.

Examples 4 to 14 and Comparative Examples 3 to 6.

An organic light emitting diode was manufactured in the same manner as in Example 3, except that the materials shown in Table 2 below were used as the dopant and the host compound of the light emitting layer in Example 3, respectively.

The organic light emitting device manufactured using each compound as a host and a dopant material was tested at a current density of 20 mA/cm ² The results are shown in Table 2 below. The lifetime was measured as the time (T97) at which the luminance became 97% of the initial luminance.

Host (light emitting layer) dopant (light emitting layer) Driving voltage (V) Luminous Efficiency (cd/A) Lifetime (hr) Example 3 BH-A A-2 4.40 3.42 76 Example 4 BH-A A-4 4.35 3.61 63 Example 5 BH-A A-6 4.39 3.45 70 Example 6 BH-A A-7 4.41 3.58 75 Example 7 BH-B B-2 4.41 3.36 65 Example 8 BH-B B-5 4.21 3.36 64 Example 9 BH-B B-7 4.41 3.36 68 Example 10 BH-B A-7 4.41 3.61 84 Comparative Example 3 BH-A X-3 4.43 2.99 59 Comparative Example 4 BH-B X-4 4.41 3.14 54 Comparative Example 5 BH-B X-5 4.93 3.30 58 Example 11 BH-C A-2 4.11 3.39 65 Example 12 BH-C A-7 4.10 3.49 76 Example 13 BH-C B-2 4.09 3.33 62 Example 14 BH-C B-5 3.90 3.44 63 Comparative Example 6 BH-C X-3 4.23 2.78 57

As shown in Table 2, the devices of Examples 3 to 14 using the compound having the structure of Formula 1 have blue high efficiency and longer lifespan than the devices of Comparative Examples 3 to 6.

Experimental Example 3: Maximum emission wavelength measurement and TGA analysis

Example 15 and Comparative Examples 7 to 9

The maximum emission wavelengths of the following compounds were measured and described in Table 3 below, and the measuring equipment used to measure them is a JASCO FP-8600 fluorescence spectrophotometer.

The maximum emission wavelength of the compound can be obtained as follows. Prepare a sample for measurement by dissolving the compound to be measured using toluene as a solvent at a concentration of 1 μM (microM). The sample solution is placed in a quartz cell and degassed using nitrogen gas (N ₂ ) to remove oxygen in the solution, and then the fluorescence spectrum is measured at room temperature (300K) using a measuring device. At this time, the wavelength value (nm) of the maximum emission peak can be obtained.

Comparative Example 7 Comparative Example 8 Example 15 Comparative Example 9 compound X-6 X-3 A-2 X-7 Maximum emission wavelength (nm) 430 442 454 451 Molecular Weight 867 987 TGA Td-1% loss (℃) 407 403 395 490 Residual (%) 0.2 1.2 2.8 62.6

TGA (thermos gravimetric analyzer, thermogravimetric analyzer) is a device that measures the change in mass of a sample as a function of time or temperature by applying temperature to the sample. Mass loss of a material is caused by evaporation or chemical reactions that produce gaseous products. Using Q-500, take a sample of less than 5 mg on a Pt pan and heat it from room temperature to 700°C at a rate of 20°C/min. At this time, measure the temperature (=Td-1% loss) at which the mass of the compound is reduced by 1% relative to the total weight of the compound, and the amount (percent) of the residue remaining in the pan after heating to 700°C. A TGA graph of Compound A-2 of Example 15 is shown in FIG. 4 , and a TGA graph of Compound X-7 of Comparative Example 9 is shown in FIG. 5 .

The compounds X-3, X-6, and A-2 of Comparative Examples 7, 8 and 15 all have the same molecular weight, but the maximum emission wavelength is all different. Compound A-2 satisfying Formula 1 has an emission wavelength very suitable for use as a blue dopant. The maximum emission wavelength of compound X-6 is very short.

Compound X-7 (Comparative Example 9) having a maximum emission wavelength similar to that of Compound A-2 (Example 15) had a Td-1% loss value of 490° C. as a result of thermogravimetric analysis of the compound. Compared to the Td-1% loss value (395° C.) of Compound A-2 (Example 15) satisfying Formula 1 of the present invention, it is a very high value. In addition, in Compound X-7 of Comparative Example 9, 62% of the compound remained in the pan after TGA analysis, but in Example Compound A-2 of the present invention, 2.8% of the compound remained in the pan after TGA analysis.

Through this experiment, it was confirmed that the compound satisfying Formula 1 has an appropriate maximum emission wavelength as a blue fluorescent dopant compared to a similar molecular weight, and at the same time has a low Td-1% loss value, so that it is an organic material suitable for a deposition device.

101: substrate
102: positive electrode
103: hole injection layer
104: hole transport layer
105: electron blocking layer
106: light emitting layer
107: hole blocking layer
108: electron transport layer
109: electron injection layer
110: cathode

Claims (14)

A compound represented by the following formula 2-1 or 2-2:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,
Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; And one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group or a substituent to which two or more substituents are connected, or adjacent substituents combine to form a substituted or unsubstituted ring,
R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r1 is an integer from 0 to 5, r2 is an integer from 0 to 3, r3 is an integer from 0 to 2,
When r1 is 2 or more, R1 are the same as or different from each other,
When r2 is 2 or more, R2 are the same as or different from each other,
When r3 is 2, R3 is the same as or different from each other. delete The compound according to claim 1, wherein Formula 2-1 is represented by Formula 4-1, and Formula 2-2 is represented by Formula 4-2:
[Formula 4-1]

[Formula 4-2]

In Formulas 4-1 and 4-2,
Ar1 to Ar4, R1 to R3 and r1 to r3 have the same definitions as in Formulas 2-1 and 2-2. The compound according to claim 1, wherein Formula 2-1 is represented by any one of Formulas 3-1 to 3-4, and Formula 2-2 is represented by any one of Formulas 3-5 to 3-8:
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

[Formula 3-6]

[Formula 3-7]

[Formula 3-8]

In Formulas 3-1 to 3-8,
Ar1 to Ar4, R1 to R3 and r1 to r3 have the same definitions as in Formulas 2-1 and 2-2. The compound according to claim 1, wherein Formula 2-1 is represented by any one of Formulas 5-1 to 5-4, and Formula 2-2 is represented by any one of Formulas 5-5 to 5-8:
[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

[Formula 5-4]

[Formula 5-5]

[Formula 5-6]

[Formula 5-7]

[Formula 5-8]

In Formulas 5-1 to 5-8,
Ar1 to Ar4, R1 to R3 and r1 to r3 have the same definitions as in Formulas 2-1 and 2-2. The method according to claim 1, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a silyl group, an amine group, and an O having 2 to 20 carbon atoms Or a C 6 to C 20 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of S-containing heterocyclic groups or a substituent to which two or more substituents are connected; Or a C 2 to C 20 or S-containing heterocyclic group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms,
Ar1 and Ar2 are a phenyl group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms, combine with each other to form a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms, Ar3 and Ar4 are a phenyl group having 1 to 6 carbon atoms A phenyl group substituted or unsubstituted with an alkyl group, and combined with each other to form a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms. The compound according to claim 1, wherein the compound represented by Formula 2-1 or 2-2 is any one selected from the following compounds:

. a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 and 3 to 7 Phosphorus organic light emitting device. The organic light-emitting device of claim 8 , wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic light emitting device of claim 8 , wherein the organic material layer includes an emission layer, the emission layer includes a dopant material, and the dopant material includes the compound. The organic light emitting device of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound and a compound represented by the following Chemical Formula H:
[Formula H]

In the formula (H),
L21 and L22 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar21 and Ar22 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The organic light-emitting device of claim 8 , wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound. The organic light-emitting device of claim 8 , wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer includes the compound. The organic material layer of claim 8, further comprising one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. light emitting element.

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