KR102428976B1 - 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

Compound and organic light emitting device comprising the same

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0161668 filed with the Korean Intellectual Property Office on December 14, 2018, 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. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, 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 It lights up when it falls back to the ground state.

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 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,

R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitro group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted ring,

Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r7 is 1 or 2, if 2, R7 are the same as or different from each other,

r8 is an integer of 1 to 3, and in the case of 2 or more, R8 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 described above.

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 lifetime characteristics of the device can be improved by the thermal stability of the compound.

1 to 3 illustrate examples of an organic light emitting diode according to an exemplary embodiment of the present specification.

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

The present specification provides a compound represented by Formula 1 above.

The compound represented by Formula 1 has a core structure in which benzofuran is condensed to a polycyclic ring in which one cyclohexane ring is condensed to naphthalene, and an arylamine group is connected to the core structure.

The cyclohexane ring in the core structure increases the solubility of the substance, thereby facilitating the synthesis of the compound. In addition, the molecular orientation value is high compared to the case where one cyclohexane ring is condensed and two cyclohexane rings are condensed, so that the luminous efficiency is high.

Since the compound represented by Formula 1 includes two amine groups, the radiation transfer probability (oscillator strength) is increased compared to a structure that does not include an amine group or includes one amine group, so that the luminous efficiency of the device is high.

Therefore, when the compound of the present invention is applied to an organic light emitting device, the luminous efficiency is excellent, and the effects of low driving voltage, high efficiency and long life are exhibited.

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

In the present specification, Cn means n carbon atoms.

In the present specification, “Cn-Cm” means “n to m carbon atoms”.

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 not limited, and when two or more are substituted , two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitro group; nitrile group; an alkyl group; cycloalkyl group; amine group; aryl group; And substituted with 1 or 2 or more substituents selected from the group consisting of a heteroaryl group containing at least one of N, O and S atoms, or substituted with a substituent to which two or more of the above-exemplified substituents are linked, or having no substituents means that

In one embodiment of the present specification, the "substituted or unsubstituted" is deuterium; halogen group; nitro group; nitrile group; C1-C10 alkyl group; C3-C10 cycloalkyl group; silyl group; amine group; C6-30 aryl group; and 1 or 2 or more substituents selected from the group consisting of a C2-30 heteroaryl group containing at least one of N, O, and S atoms, or is substituted with a substituent to which two or more of the above exemplified substituents are linked, or It means not having any substituents.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50, more preferably 1 to 30. 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, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1- Methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl propyl, 1,1-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 preferably has 3 to 60 carbon atoms, more preferably 3 to 30 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3 ,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, 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 heteroaryl group includes at least one of N, O and S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms, and more preferably 2 to 30 or 2 to 20 carbon atoms. do. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, acri Din group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pteridine group, pyrido pyrimidine group, pyrido group pyrazine), pyrazino pyrazine, isoquinoline, indole, pyrido indole, indeno pyrimidine (5H-indeno pyrimidine), carbazole, benzoxazole, benzimidazole , benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofuran group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group and There is a thiadiazolyl group, and the like, but is not limited thereto.

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.

In the present specification, the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except for non-monovalent ones.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitro group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitro group; nitrile group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted C2-C30 ring.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitro group; nitrile group; a substituted or unsubstituted C1-C5 alkyl group; a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted C2-C30 ring.

In an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a C1-C5 alkyl group unsubstituted or substituted with deuterium; Or it is a C6-C30 aryl group substituted or unsubstituted with deuterium, or adjacent substituents combine to form a fluorene ring substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a C1-C5 alkyl group unsubstituted or substituted with deuterium; Or it is a C6-C30 aryl group, or adjacent substituents combine to form a fluorene ring.

In an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a methyl group unsubstituted or substituted with deuterium; or a phenyl group, or adjacent substituents combine to form a fluorene ring.

In an exemplary embodiment of the present specification, R1 is hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R2 is hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other.

In an exemplary embodiment of the present specification, R3 is hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R4 is hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R3 and R4 are bonded to each other to form a C2-C20 ring.

In the exemplary embodiment of the present specification, R3 and R4 are phenyl groups, and combine with each other to form a fluorene ring.

In an exemplary embodiment of the present specification, R3 and R4 are the same as or different from each other.

In an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; a methyl group unsubstituted or substituted with deuterium; or a phenyl group.

In an exemplary embodiment of the present specification, R6 is hydrogen; heavy hydrogen; a methyl group unsubstituted or substituted with deuterium; or a phenyl group.

In an exemplary embodiment of the present specification, R5 and R6 are the same as or different from each other.

In an exemplary embodiment of the present specification, R7 and R8 are the same as or different from each other, and each independently hydrogen; or deuterium.

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 aryl group; Or a substituted or unsubstituted heteroaryl 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 C6-C30 aryl group unsubstituted or substituted with X1; or a C2-C30 heteroaryl group unsubstituted or substituted with X2.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a C6-C20 aryl group unsubstituted or substituted with X1; or a C2-C20 heteroaryl group unsubstituted or substituted with X2.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a monocyclic to 4-ring aryl group unsubstituted or substituted with X1; or a monocyclic to 5-ring heteroaryl group unsubstituted or substituted with X2.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a monocyclic to 4-ring aryl group unsubstituted or substituted with X1; or a monocyclic to 4-ring heteroaryl group unsubstituted or substituted with X2.

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 unsubstituted or substituted with X1; a biphenyl group unsubstituted or substituted with X1; a terphenyl group unsubstituted or substituted with X1; a naphthyl group unsubstituted or substituted with X1; a fluorenyl group substituted or unsubstituted with X1; A benzofluorenyl group substituted or unsubstituted with X1; A carbazole group unsubstituted or substituted with X2; A benzocarbazole group substituted or unsubstituted with X2; A dibenzofuran group substituted or unsubstituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group substituted or unsubstituted with X2; A naphthobenzothiophene group unsubstituted or substituted with X2; an indolocarbazole group substituted or unsubstituted with X2; A pyridine group unsubstituted or substituted with X2; a pyrimidine group unsubstituted or substituted with X2; Or a triazine group unsubstituted or substituted with X2.

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 unsubstituted or substituted with X1; a biphenyl group unsubstituted or substituted with X1; a naphthyl group unsubstituted or substituted with X1; a fluorenyl group substituted or unsubstituted with X1; A benzofluorenyl group substituted or unsubstituted with X1; A dibenzofuran group substituted or unsubstituted with X2; A dibenzothiophene group substituted or unsubstituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; A naphthobenzothiophene group unsubstituted or substituted with X2; Or an indolocarbazole group substituted or unsubstituted with X2.

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 unsubstituted or substituted with X1; a biphenyl group unsubstituted or substituted with X1; a terphenyl group unsubstituted or substituted with X1; a naphthyl group unsubstituted or substituted with X1; a fluorenyl group substituted or unsubstituted with X1; A dibenzofuran group substituted or unsubstituted with X2; A dibenzothiophene group substituted or unsubstituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; Or a naphthobenzothiophene group unsubstituted or substituted with X2.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C3-C10 cycloalkyl group, a C6-C20 aryl group and a C6-C20 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a silyl group or a substituent to which two or more groups selected from the group are connected; or a C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C1-C5 alkyl group, and a C3-C10 cycloalkyl group, or a substituent to which two or more groups selected from the group 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 one or more substituents selected from the group consisting of deuterium, a halogen group and a C1-C5 alkyl group or two or more groups selected from the group are linked a C6-C20 aryl group unsubstituted or substituted with a substituent; or a C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and a C1-C5 alkyl group or a substituent to which two or more groups selected from the group 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 substituted with deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C1-C5 alkyl group substituted with deuterium, a halogen group a phenyl group unsubstituted or substituted with a C1-C5 alkyl group, a C3-C10 cycloalkyl group, a trimethylsilyl group, or a dimethylphenylsilyl group; a biphenyl group unsubstituted or substituted with a halogen group, a C1-C5 alkyl group, or a trimethylsilyl group; terphenyl group; a naphthyl group unsubstituted or substituted with a C1-C5 alkyl group; a fluorenyl group unsubstituted or substituted with a C1-C5 alkyl group; a benzofluorenyl group unsubstituted or substituted with a C1-C5 alkyl group; a dibenzofuran group unsubstituted or substituted with a C1-C5 alkyl group or a C3-C10 cycloalkyl group; naphthobenzofuran group; dibenzothiophene group; naphthobenzothiophene group; or an indolocarbazole 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, a nitrile group, a C1-C5 alkyl group, a C1-C5 alkyl group substituted with deuterium, or a halogen group a phenyl group unsubstituted or substituted with a C1-C5 alkyl group; biphenyl group; terphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a C1-C5 alkyl group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene 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 deuterium, a halogen group, a nitrile group, a methyl group, a tert-butyl group, a methyl group substituted with deuterium, a trifluoromethyl group, a cyclohexyl group a phenyl group unsubstituted or substituted with a sil group, a trimethylsilyl group, or a dimethylphenylsilyl group; a biphenyl group unsubstituted or substituted with a halogen group, a tert-butyl group, or a trimethylsilyl group; terphenyl group; a naphthyl group unsubstituted or substituted with a tert-butyl group; a fluorenyl group unsubstituted or substituted with a methyl group; a methyl group-substituted or unsubstituted benzofluorenyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; naphthobenzofuran group; dibenzothiophene group; naphthobenzothiophene group; or an indolocarbazole 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 or unsubstituted with deuterium, a halogen group, a methyl group, a tert-butyl group, a methyl group substituted with deuterium, or a trifluoromethyl group phenyl group; biphenyl group; terphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group, and Ar2 is a substituted or unsubstituted heteroaryl group,

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group, and Ar4 is a substituted or unsubstituted heteroaryl group,

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroaryl group, and Ar2 is a substituted or unsubstituted aryl group,

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted heteroaryl group, and Ar4 is a substituted or unsubstituted aryl group,

In the exemplary embodiment of the present specification, at least one of Ar1 and Ar2 may be represented by the following Chemical Formula A1.

In the exemplary embodiment of the present specification, at least one of Ar3 and Ar4 may be represented by the following Chemical Formula A1.

[Formula A1]

In the formula A1,

Q1 is C(T2)(T3); S; or O;

T1 to T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; nitro group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with adjacent substituents,

t1 is an integer from 0 to 7, and when t1 is 2 or more, T1 is the same as or different from each other.

In an exemplary embodiment of the present specification, T2 and T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a C1-C5 alkyl group.

In an exemplary embodiment of the present specification, T2 and T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a methyl group.

In an exemplary embodiment of the present specification, T1 is hydrogen; or deuterium, or two adjacent T1s combine with each other to form a benzene ring.

According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.

According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group; benzofluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; dibenzothiophene group; naphthobenzofuran group; or a naphthobenzothiophene group.

According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.

According to an exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.

According to an exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is a fluorenyl group unsubstituted or substituted with a methyl group; benzofluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; dibenzothiophene group; naphthobenzofuran group; or a naphthobenzothiophene group.

According to an exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.

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

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

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and any one selected from the following group A or B.

[Group A]

[Group B]

은 N에 연결되는 위치이며,In groups A and B,

is the position connected to N,

The group A is unsubstituted or substituted with X1, and the group B is unsubstituted or substituted with X2.

In an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently one or more substituents selected from the group consisting of deuterium, a halogen group and a C1-C5 alkyl group or two or more groups selected from the group are linked is a substituent.

In an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently deuterium; halogen group; nitrile group; a C1-C5 alkyl group unsubstituted or substituted with deuterium or a halogen group; C3-C10 cycloalkyl group; a silyl group substituted with a C1-C5 alkyl group or a C6-C20 aryl group; or a C6-C20 aryl group.

In an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently deuterium; halogen group; nitrile group; methyl group; tert-butyl group; a methyl group substituted with deuterium; a methyl group substituted with a halogen group; cyclohexyl group; trimethylsilyl group; It is a dimethylphenylsilyl group.

In an exemplary embodiment of the present specification, X1 is deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C1-C5 alkyl group substituted with deuterium, a C1-C5 alkyl group substituted with a halogen group, C3-C10 Cycloalkyl group, trimethylsilyl group or dimethylphenylsilyl group

In an exemplary embodiment of the present specification, X1 is deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C1-C5 alkyl group substituted with deuterium, or a C1-C5 alkyl group substituted with a halogen group.

In an exemplary embodiment of the present specification, X2 is a C1-C5 alkyl group or a C3-C10 cycloalkyl group.

In an exemplary embodiment of the present specification, X2 is a C1-C5 alkyl group.

In an exemplary embodiment of the present specification, r7 is 1 or 2, and in the case of 2, R7 is the same as or different from each other.

In the exemplary embodiment of the present specification, r7 is 2.

In the exemplary embodiment of the present specification, r8 is an integer of 1 to 3, and when 2 or more, R8 is the same or different from each other.

In the exemplary embodiment of the present specification, r8 is 3.

In the 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 an 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 any one of the following Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

Definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.

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

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical 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,

Definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.

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

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

In Formulas 3-1 to 3-4,

Definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.

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

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

[Formula 4-4]

In Formulas 4-1 to 4-4,

Definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 5-1.

[Formula 5-1]

In Formula 5-1,

Definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.

In the exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 6-1.

[Formula 6-1]

In Formula 6-1,

Definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.

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. In the following preparations, representative examples are described, but 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, and the like can be changed.

For example, according to an exemplary embodiment, 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, R5 and R6 are the same as those defined in Formula 1 above. Although R1 to R4, R7 and R8 are not indicated in the above general formula, R1 to R4, R7 and R8 are substituted by using a reactant or by a method known in the art for the product produced by the above general formula 1 to R4, R7 and R8 may be substituted.

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

In one embodiment of the present specification, the 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.

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, it 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 the '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 this 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 of C, ii) is included in one or more of the one or more layers of D, or iii) ) means all of which are included in one or more C-layers and one or more D-layers, 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.

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a dopant of the emission layer.

In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound represented by Formula 1, and the emission layer including the compound represented by Formula 1 has a blue color.

In the exemplary embodiment of the present specification, the organic material layer includes two or more emission layers, and at least one of the two or more emission layers includes the compound represented by Formula 1 above. The light emitting layer including the compound represented by Formula 1 has a blue color, and the light emitting layer not including the compound represented by Formula 1 may include a blue, red, or green light emitting compound known in the art.

The organic light emitting device 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 an exemplary embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene 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 C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 heteroarylene group 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; C6-C20 arylene group; or a C2-C20 heteroarylene group including N, O, or S. The arylene group or heteroarylene group is unsubstituted or substituted with a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 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 phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; or a substituted or unsubstituted divalent dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a C6-C30 aryl group unsubstituted or substituted with deuterium; or a C2-C30 heteroaryl group unsubstituted or substituted with deuterium.

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

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

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

In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C3-C10 cycloalkyl group, a C1-C5 alkyl group a phenyl group unsubstituted or substituted with a substituted silyl group or a C6-C20 aryl group; a biphenyl group unsubstituted or substituted with a silyl group substituted with deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C3-C10 cycloalkyl group, a C1-C5 alkyl group, or a C6-C20 aryl group; a naphthylene group unsubstituted or substituted with a deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C3-C10 cycloalkyl group, a C1-C5 alkyl group, or a C6-C20 aryl group; anthracene group; phenanthrene group; phenalene group; a thiophene group unsubstituted or substituted with a silyl group substituted with deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C3-C10 cycloalkyl group, a C1-C5 alkyl group, or a C6-C20 aryl group; 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 a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted phenalene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; a substituted or unsubstituted furan group; a substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.

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; terphenyl group; naphthyl group; phenanthryl group; a fluorenyl group unsubstituted or substituted with a methyl group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group, wherein Ar21 and Ar22 may include one or more deuterium.

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; terphenyl group; naphthyl group; dibenzofuran group; or a naphthobenzofuran group, wherein Ar21 and Ar22 may include one or more deuterium.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are different from each other.

In an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is an aryl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is a heteroaryl group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R22 is a group represented by -L23-Ar23.

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

In an exemplary embodiment of the present specification, four or more of R21 to R28 are deuterium, and the rest are hydrogen.

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

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

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

In an exemplary embodiment of the present specification, the formula H is represented by the following formula H-1.

[Formula H-1]

In Formula H-1,

The definitions of L21, L22, R21, R23 to R28, Ar21 and Ar22 are as defined in Formula H,

L23 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar23 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, the descriptions of Ar21 and Ar22 described above may be applied to Ar23.

In the exemplary embodiment of the present specification, the descriptions of L21 and L22 described above may be applied to L23.

In an exemplary embodiment of the present specification, Ar23 is a phenyl group unsubstituted or substituted with deuterium; biphenyl group; naphthylene group; anthracene group; phenanthrene group; dibenzofuran group; naphthobenzofuran group; pyridine group; or an isoquinoline group.

In one embodiment of the present specification, the L23 is a direct bond; phenylene group; naphthylene group; or a divalent thiophene group.

In an exemplary embodiment of the present specification, Ar23 is a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; Or a dibenzofuran group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, the L23 is a direct bond; a phenylene group unsubstituted or substituted with deuterium; or a naphthylene group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, the compound represented by Formula H-1 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 is 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 one embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer.

In one 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, wherein at least one of the two or more organic material layers includes a compound represented by Formula 1 above.

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

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

In one embodiment of the present specification, the second electrode is a negative electrode or 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 the 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 a first electrode 102 , a light emitting layer 106 , and a second electrode 110 are sequentially stacked on a substrate 101 . The compound represented by Formula 1 is included in the light emitting layer.

2 shows the structure of an organic light emitting device in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. is exemplified. According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in one or more of the organic material layers. According to another exemplary embodiment, the compound represented by Formula 1 is included in at least one of the hole injection layer, the hole transport layer, and the light emitting layer.

3 shows a first electrode 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, an electron transport layer ( 108), the electron injection layer 109, and the second electrode 110 are sequentially stacked, the structure of the organic light emitting device is exemplified. According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in one or more of the organic material layers. According to another exemplary embodiment, the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an 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 at least one layer of the organic material layer includes the 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 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 a substrate to form an 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 the above 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 means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to the above 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.

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

In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

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; A multi-layered material such as LiF/Al or 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.

In the present specification, when the compound represented by Formula 1 is included in an organic material layer other than the light emitting layer or an additional light emitting layer is provided, the light emitting material of the light emitting layer receives and bonds holes and electrons from the hole transport layer and the electron transport layer, respectively. As a material capable of emitting light in the visible light region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, 8-hydroxyquinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; and rubrene, 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 migration 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 include metal porphyrin, oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic materials; 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. As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is preferable, 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, samarium, and the like, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injection material is excellent in the ability to transport electrons and has an electron receiving effect from the second electrode and an excellent electron injection 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 and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, 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 a 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 1]

Under nitrogen atmosphere, intermediate 1-a 20 g, 4-chloro-2-fluorophenyl boronic acid 1-b [(4-chloro-2-fluorophenyl) boronic acid] 14 g, potassium carbonate [potassium carbonate] 18 g dioxane After adding 400 mL and 100 mL of water, 2.2 g of tetrakis(triphenylhosphine)palladium(0)[tetrakis(triphenylhosphine)palladium(0)]Pd(PPh ₃ ) ₄ was added, and then heated at 120 ^o C. Stirred for 12 hours. After completion of the reaction, the reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and filtered by treatment with MgSO ₄ (anhydrous). The filtered solution was distilled off under reduced pressure and purified by recrystallization (ethylacetate/hexane) to obtain 18 g of Intermediate 1-c. (Yield 78%, Mass [M+]=357)

In a nitrogen atmosphere, 18 g of Intermediate 1-c and 21 g of potassium carbonate were added to 300 mL of dimethylformamide [N-dimethylformamide] and stirred at 140 ^o C for 1 hour to synthesize Intermediate 1-d. After completion of the reaction, the reaction solution was cooled to room temperature, and then 9.8 mL of nona plate fluoride [perfluorobutanesulfonyl floride] was added and stirred for 0.5 hours. 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 20 g of Intermediate 1-e. (Yield 65%, Mass [M+]=619)

After dissolving 2.0 g of Intermediate 1-e, 1.9 g of amine A-1, and 2.0 g of potassium phosphate in toluene (30 ml) under a nitrogen atmosphere, bis(tritert-butylphosphine)palladium(0)[Bis 16 mg of (tri-tert-butylphosphine)palladium(0)] was added, heated at 120 ^o C, and stirred for 18 hours. When the reaction was completed, the reaction solution was cooled to room temperature, water and aq.NH ₄ Cl 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 (hexane/toluene) to obtain 1.8 g of Compound 1. (Yield 67%, Mass [M+]=846)

[Synthesis Example 2]

In the synthesis of Compound 1 of Synthesis Example 1, 2.3 g of Compound 2 was obtained in the same manner as in the synthesis of Compound 1, except that 2.8 g of A-2 was used instead of amine A-1. (Yield 64%, Mass [M+]=1134)

[Synthesis Example 3]

In the synthesis of Compound 1 of Synthesis Example 1, 2.2 g of Compound 3 was obtained in the same manner as in the synthesis of Compound 1, except that 1.8 g of A-3 was used instead of amine A-1. (Yield 73%, Mass [M+]=631)

[Synthesis Example 4]

In the synthesis of Compound 1 of Synthesis Example 1, 3.1 g of Compound 4 was obtained in the same manner as in the synthesis of Compound 1, except that 3.0 g of A-4 was used instead of amine A-1. (Yield 74%, Mass [M+]=886)

[Synthesis Example 5]

In the synthesis of Compound 1 of Synthesis Example 1, 3.3 g of Compound 5 was obtained in the same manner as in the synthesis of Compound 1, except that 3.2 g of A-5 was used instead of amine A-1. (Yield 75%, Mass [M+]=914)

[Synthesis Example 6]

In the synthesis of Intermediate 1-c of Synthesis Example 1, 16 g of Intermediate 2-c was obtained in the same manner as in the synthesis of Intermediate 1-c, except that 20 g of 2-a was used instead of Intermediate 1-a. (Yield 70%, Mass [M+]=357)

In the synthesis of Intermediate 1-e of Synthesis Example 1, 21 g of Intermediate 2-e was obtained in the same manner as in the synthesis of Intermediate 1-e, except that 16 g of 2-c was used instead of 1-c. (Yield 75%, Mass [M+]=619)

In the synthesis of Compound 1 of Synthesis Example 1, 3.0 g of 2-e instead of intermediate 1-e and 2.4 g of A-6 instead of amine A-1 were used in the synthesis of Compound 1 in the same manner as in the synthesis of Compound 1 to prepare 2.8 g of Compound 6 obtained. (Yield 78%, Mass [M+]=757)

[Synthesis Example 7]

In the synthesis of Compound 1 of Synthesis Example 1, 3.0 g of 2-e instead of Intermediate 1-e and 2.6 g of A-4 instead of amine A-1 were used in the synthesis of Compound 1 in the same manner as in the synthesis of Compound 1 to prepare 3.2 g of Compound 7 obtained. (Yield 84%, Mass [M+]=801)

[Synthesis Example 8]

In the synthesis of Intermediate 1-c of Synthesis Example 1, 18 g of Intermediate 2-c was obtained in the same manner as in the synthesis of Intermediate 1-c, except that 20 g of 2-a was used instead of Intermediate 1-a. (Yield 78%, Mass [M+]=357)

In the synthesis of Intermediate 1-e of Synthesis Example 1, 18 g of Intermediate 2-e was obtained in the same manner as in the synthesis of Intermediate 1-e, except that 18 g of 2-c was used instead of 1-c. (Yield 58%, Mass [M+]=619)

In the synthesis of Compound 1 of Synthesis Example 1, 3.0 g of 3-e instead of Intermediate 1-e and 1.7 g of A-8 instead of amine A-1 were used in the synthesis of Compound 1 in the same manner as in the synthesis of Compound 1 to prepare 2.1 g of Compound 8 obtained. (Yield 72%, Mass [M+]=621)

[Synthesis Example 9]

In the synthesis of Compound 1 of Synthesis Example 1, 5.1 g of Compound 9 was obtained in the same manner as in the synthesis of Compound 1, except that 5.0 g of 3-e was used instead of Intermediate 1-e. (Yield 75%, Mass [M+]=846)

[Synthesis Example 10]

In the synthesis of Compound 1 of Synthesis Example 1, 3.3 g of Compound 10 was prepared in the same manner as in the synthesis of Compound 1, except that 3.0 g of 3-e instead of Intermediate 1-e and 3.0 g of A-9 instead of amine A-1 were used. obtained. (Yield 78%, Mass [M+]=886)

[Synthesis Example 11]

In the synthesis of Compound 1 of Synthesis Example 1, 3.0 g of 3-e instead of Intermediate 1-e and 1.8 g of A-3 instead of amine A-1 were used in the synthesis of Compound 1 in the same manner as in the synthesis of Compound 1 to prepare 2.3 g of Compound 11 obtained. (Yield 77%, Mass [M+]=631)

[Synthesis Example 12]

In the synthesis of Compound 1 of Synthesis Example 1, 2.1 g of Compound 12 was prepared in the same manner as in the synthesis of Compound 1, except that 3.0 g of 3-e instead of Intermediate 1-e and 3.0 g of A-10 instead of amine A-1 were used. obtained. (Yield 70%, Mass [M+]=886)

[Synthesis Example 13]

In the synthesis of Intermediate 1-c of Synthesis Example 1, 15 g of Intermediate 4-c was obtained in the same manner as in the synthesis of Intermediate 1-c, except that 20 g of 4-a was used instead of Intermediate 1-a. (Yield 65%, Mass [M+]=357)

In the synthesis of Intermediate 1-e of Synthesis Example 1, 13 g of Intermediate 4-e was obtained in the same manner as in the synthesis of Intermediate 1-e, except that 15 g of 4-c was used instead of 1-c. (Yield 50%, Mass [M+]=619)

2.7 g of compound 13 was prepared in the same manner as in the synthesis of compound 1, except that 3.0 g of 4-e instead of intermediate 1-e and 2.0 g of A-11 instead of amine A-1 were used in the synthesis of compound 1 of Synthesis Example 1 obtained. (Yield 82%, Mass [M+]=689)

[Synthesis Example 14]

In the synthesis of Compound 1 of Synthesis Example 1, 3.2 g of Compound 14 was prepared in the same manner as in the synthesis of Compound 1, except that 3.0 g of 3-e instead of Intermediate 1-e and 3.0 g of A-12 instead of amine A-1 were used. obtained. (Yield 74%, Mass [M+]=914)

[Synthesis Example 15]

In the synthesis of Intermediate 1-c of Synthesis Example 1, 8.4 g of Intermediate 5-c was obtained in the same manner as in the synthesis of Intermediate 1-c, except that 10 g of 5-a was used instead of Intermediate 1-a. (Yield 70%, Mass [M+]=363)

In the synthesis of Intermediate 1-e of Synthesis Example 1, 8.5 g of Intermediate 5-e was obtained in the same manner as in the synthesis of Intermediate 1-e, except that 8.4 g of 5-c was used instead of 1-c. (Yield 61%, Mass [M+]=625)

In the synthesis of Compound 1 of Synthesis Example 1, 3.0 g of 5-e instead of Intermediate 1-e and 2.6 g of A-3 instead of amine A-1 were used in the synthesis of Compound 1 in the same manner as in the synthesis of Compound 1 to prepare 2.1 g of Compound 15 obtained. (Yield 70%, Mass [M+]=637)

[Synthesis Example 16]

In the synthesis of Intermediate 1-c of Synthesis Example 1, 8.0 g of Intermediate 6-c was obtained in the same manner as in the synthesis of Intermediate 1-c, except that 10 g of 6-a was used instead of Intermediate 1-a. (Yield 73%, Mass [M+]=481)

In the synthesis of Intermediate 1-e of Synthesis Example 1, 7.6 g of Intermediate 6-e was obtained in the same manner as in the synthesis of Intermediate 1-e, except that 8.0 g of 6-c was used instead of 1-c. (Yield 63%, Mass [M+]=744)

In the synthesis of Compound 1 of Synthesis Example 1, 2.7 g of Compound 16 was prepared in the same manner as in the synthesis of Compound 1, except that 3.0 g of 6-e instead of Intermediate 1-e and 1.9 g of A-13 instead of amine A-1 were used. obtained. (Yield 79%, Mass [M+]=858)

[Synthesis Example 17]

In the synthesis of Intermediate 1-c of Synthesis Example 1, 4.5 g of Intermediate 7-c was obtained in the same manner as in the synthesis of Intermediate 1-c, except that 5.0 g of 7-a was used instead of Intermediate 1-a. (Yield 80%, Mass [M+]=479)

In the synthesis of Intermediate 1-e of Synthesis Example 1, 4.2 g of Intermediate 7-e was obtained in the same manner as in the synthesis of Intermediate 1-e, except that 4.5 g of 7-c was used instead of 1-c. (Yield 61%, Mass [M+]=742)

In the synthesis of Compound 1 of Synthesis Example 1, 3.0 g of 7-e instead of Intermediate 1-e and 1.4 g of A-8 instead of amine A-1 were used in the synthesis of Compound 1 in the same manner as in the synthesis of Compound 1 to prepare 2.3 g of Compound 17 obtained. (Yield 77%, Mass [M+]=743)

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of the following formula [HAT-CN] to a thickness of 50 Å on the ITO transparent electrode prepared as described above. A hole transport layer was formed by vacuum-depositing the following formula [NPB] to a thickness of 1,000 Å on the hole injection layer. On the hole transport layer, the following formula [HT-A] was vacuum deposited to a thickness of 200 Å to form an electron blocking layer.

Then, [BH-1] was vacuum-deposited to a thickness of 300 Å as a light emitting host on the electron blocking layer to form a light emitting layer. While depositing the light emitting layer, Compound 1 was used as a blue light emitting dopant in an amount of 3 wt% based on 100% of the total weight of the host. On the light emitting layer, [TPBI] and the following formula [LiQ] were vacuum-deposited in a 1:1 weight ratio to form a first electron transport layer to a thickness of 200 Å. [LiF] was vacuum-deposited on the first electron transport layer to form a second electron transport layer to a thickness of 100 Å. A cathode was formed by depositing aluminum to a thickness of 1,000 Å on the second electron transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 1.0 Å/sec, the deposition rate of the LiF of the second electron transport layer was 0.3 Å/sec, and the aluminum of the cathode was maintained at 2 Å/sec, and the vacuum degree during deposition was By maintaining 1 Х 10 ^-7 to 5 Х 10 ^-8 torr, an organic light emitting diode was manufactured.

Examples 2 to 17 and Comparative Examples 1 and 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds of Table 1 below were used as the host and dopant of the light emitting layer in Example 1.

Efficiency, lifetime, and voltage at a current density of 10 mA/cm 2 of the organic light emitting diodes prepared in Examples 1 to 17 and Comparative Examples 1 and 2 were measured, and the results are shown in Table 1 below.

host dopant Luminous Efficiency (Cd/A) Lifetime, T95(h) Example 1 BH-1 compound 1 6.64 164 Example 2 BH-1 compound 2 6.55 159 Example 3 BH-1 compound 3 6.52 162 Example 4 BH-1 compound 4 6.48 162 Example 5 BH-1 compound 5 6.44 160 Example 6 BH-2 compound 6 6.38 156 Example 7 BH-2 compound 7 6.41 160 Example 8 BH-2 compound 8 6.35 162 Example 9 BH-2 compound 9 6.52 166 Example 10 BH-2 compound 10 6.50 164 Example 11 BH-2 compound 11 6.42 168 Example 12 BH-2 compound 12 6.40 160 Example 13 BH-3 compound 13 6.26 164 Example 14 BH-3 compound 14 6.32 159 Example 15 BH-2 compound 15 6.58 170 Example 16 BH-2 compound 16 6.60 162 Example 17 BH-1 compound 17 6.63 165 Comparative Example 1 BH-1 BD-1 2.70 56 Comparative Example 2 BH-1 BD-2 5.40 136

Compounds 1 to 17 according to an exemplary embodiment of the present invention have a core structure in which benzofuran is condensed to a polycyclic ring in which one cyclohexane ring is condensed to naphthalene, and have two arylamine groups. On the other hand, Compound BD-1 of Comparative Example 1 has one arylamine group, or Compound BD-2 of Comparative Example 2 has a core structure in which two cyclohexane rings are condensed to naphthalene.

As shown in Table 1, the devices of Examples 1 to 17 using the compound having the structure of Formula 1 have blue high efficiency and longer lifespan than the devices of Comparative Examples 1 and 2.

101: substrate
102: first 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: second electrode

Claims (11)

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 each independently hydrogen; heavy hydrogen; halogen group; nitro group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted hydrocarbon ring,
Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r7 is 1 or 2, and when r7 is 2, R7 of 2 are the same as or different from each other,
r8 is an integer of 1 to 3, and when r8 is 2 or more, two or more R8s are the same as or different from each other. The method according to claim 1, wherein Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
Definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1. The method according to claim 1, wherein Chemical Formula 1 is a compound represented by any one of the following Chemical 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,
Definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1. The method according to claim 1,
Ar1 to Ar4 are the same or different from each other, and each independently one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C3-C10 cycloalkyl group, a C6-C20 aryl group, and a silyl group. Or a C6-C20 aryl group unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected; Or a C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C1-C5 alkyl group, and a C3-C10 cycloalkyl group, or a substituent to which two or more groups selected from the group are connected. The method according to claim 1,
R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a C1-C5 alkyl group unsubstituted or substituted with deuterium; Or a C6-C30 aryl group, or adjacent substituents combine to form a fluorene ring. The method according to claim 1, R7 and R8 are the same as or different from each other, and each independently hydrogen; or deuterium. The compound according to claim 1, wherein the compound represented by Formula 1 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 comprises the compound according to any one of claims 1 to 7 light emitting element. 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 according to 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 method according to claim 8, wherein the organic material layer comprises 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. device.

Images