KR20200134149A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by chemical formula 1, and to an organic light-emitting device comprising the same. The compound is capable of improving high color purity and/or service life properties in the organic light-emitting device.

Description

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

The present invention claims the benefit of the filing date of Korean Patent No. 10-2019-0059533 filed with the Korean Intellectual Property Office on May 21, 2019, the entire contents of which are incorporated herein.

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of 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 such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The principle is that when a small amount of a dopant having an energy band gap smaller than that of a host that mainly constitutes the light emitting layer is mixed with the light emitting layer, excitons generated from the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

In order to fully exhibit the excellent characteristics of the organic light emitting device described above, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron suppression materials, electron transport materials, electron injection materials, etc., are stable and efficient materials. As it is supported by, the development of new materials is continuously required.

US Patent Application Publication No. 2004-0251816

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

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

[Formula 1]

In Formula 1,

L is a divalent substituted or unsubstituted N-containing polycyclic heteroaryl,

A ₁ and A ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

X ₁ to X ₃ are the same as or different from each other, and each independently N or CR,

At least one of X ₁ to X ₃ is N,

R is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,

R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, Combined with an adjacent group to form a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaryl,

a and b are each an integer of 0 to 4,

When a or b is plural, the substituents in parentheses are the same as or different from each other.

In addition, the present invention is a first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

The compound according to an exemplary embodiment of the present specification may be used as a material for an organic material layer of an organic light emitting device, and by using the compound, high color purity and/or lifespan characteristics may be improved in the organic light emitting device. In particular, the compound of the present invention increases the rate and speed at which the excitons generated in the triplet move to the singlet by the reverse interphase transfer (RISC), so that the time that the excitons stay in the triplet decreases, so the efficiency and lifespan of the organic light emitting device There is an increasing advantage of this.

1 and 2 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.
3 is NMR data of Compound 1.
4 is NMR data of compound 6.

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

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

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

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the 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, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heteroaryl group substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, the "substituent to which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heteroaryl group substituted with an aryl group, an aryl group substituted with an alkyl group, and the like.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 1 to 10 carbon atoms. Specific examples include methyl group; Ethyl group; Propyl group; n-propyl group; Isopropyl group; Butyl group; n-butyl group; Isobutyl group; tert-butyl group; sec-butyl group; 1-methylbutyl group; 1-ethylbutyl group; Pentyl group; n-pentyl group; Isopentyl group; Neopentyl group; tert-pentyl group; Hexyl group; n-hexyl group; 1-methylpentyl group; 2-methylpentyl group; 4-methyl-2-pentyl group; 3,3-dimethylbutyl group; 2-ethylbutyl group; Heptyl group; n-heptyl group; 1-methylhexyl group; Cyclopentylmethyl group; Cyclohexylmethyl group; Octyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethylpropyl group; 1,1-dimethylpropyl group; Isohexyl group; 2-methylpentyl group; 4-methylhexyl group; 5-methylhexyl group and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but it is preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms. Specifically, a cyclopropyl group; Cyclobutyl group; Cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; Cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; Cycloheptyl group; Cyclooctyl group, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 1 to 10 carbon atoms. Specifically, a methoxy group; Ethoxy group; n-propoxy group; Isopropoxy group; i-propyloxy group; n-butoxy group; Isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; Neopentyloxy group; Isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; Benzyloxy group; It may be a p-methylbenzyloxy group and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methylanthracenylamine group; Diphenylamine group; N-phenylnaphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group and the like, but are not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiRaRbRc, wherein Ra, Rb and Rc are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; Triethylsilyl group; t-butyldimethylsilyl group; Vinyldimethylsilyl group; Propyldimethylsilyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. More specifically, it is preferably 6 to 20 carbon atoms. Specifically, the monocyclic aryl group is a phenyl group; Biphenyl group; It may be a terphenyl group or the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferred that it has 10 to 30 carbon atoms, and more specifically, it is preferred that it has 10 to 20 carbon atoms. Specifically, the polycyclic aryl group includes a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenalenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group or the like, but is not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I 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 to each other.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes one or more atoms other than carbon, that is, heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; Furanyl group; Pyrrole group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyrido pyrimidyl group; Pyrido pyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazolyl group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Phenanthroline; Isoxazolyl group; Thiadiazolyl group; There may be a phenothiazinyl group and a dibenzofuranyl group, but are not limited thereto.

In the exemplary embodiment of the present specification, X ₁ to X ₃ are N.

In the exemplary embodiment of the present specification, X ₁ and X ₂ are N, and X ₃ is CR.

In the exemplary embodiment of the present specification, X ₁ and X ₃ are N, and X ₂ is CR.

In the exemplary embodiment of the present specification, X ₂ and X ₃ are N, and X ₁ is CR.

In the exemplary embodiment of the present specification, X ₁ and X ₂ are CR, and X ₃ is N.

In the exemplary embodiment of the present specification, X ₁ and X ₃ are CR, and X ₂ is N.

In the exemplary embodiment of the present specification, X ₂ and X ₃ are CR, and X ₁ is N.

In the exemplary embodiment of the present specification, L is a substituted or unsubstituted divalent N-containing polycyclic heteroaryl group having 3 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L is a divalent N-containing polycyclic heteroaryl group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, L is a divalent N-containing polycyclic heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted with an aryl group.

In the exemplary embodiment of the present specification, L is a divalent carbazole group unsubstituted or substituted with an aryl group; Or a divalent benzocarbazole group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, L is a divalent carbazole group, or a divalent benzocarbazole group,

The divalent carbazole group or the divalent benzocarbazole group is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L is a divalent carbazole group, or a divalent benzocarbazole group,

The divalent carbazole group or the divalent benzocarbazole group is unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, L is a divalent carbazole group, or a divalent benzocarbazole group,

The divalent carbazole group or the divalent benzocarbazole group is unsubstituted or substituted with an aryl group having 6 to 15 carbon atoms.

In the exemplary embodiment of the present specification, L is a divalent carbazole group, or a divalent benzocarbazole group,

The divalent carbazole group or the divalent benzocarbazole group is substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group.

In the exemplary embodiment of the present specification, L is a divalent carbazole group unsubstituted or substituted with a phenyl group.

In the exemplary embodiment of the present specification, L is a divalent carbazole group substituted with a phenyl group.

In the exemplary embodiment of the present specification, L is a divalent N-phenylcarbazole group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or It is an unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, an alkyl group, an aryl group, or a heteroaryl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ 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 the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms. It is an aryl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or Unsubstituted terphenyl group, substituted or unsubstituted anthracene group, substituted or unsubstituted phenanthrene group, substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorene group, substituted or unsubstituted carbazole group, substituted Or an unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ 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 naphthyl group, a substituted or It is an unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted dibenzofuran group to be.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, carbazole group, dibenzofuran group, or dibenzothiophene group is deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted Substituted or unsubstituted with a heteroaryl group, a substituted or unsubstituted phosphine oxide group, or a substituted or unsubstituted silyl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, carbazole group, dibenzofuran group, or dibenzothiophene group is deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or non-substituted It is unsubstituted or substituted with a cyclic heteroaryl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, carbazole group, dibenzofuran group, or dibenzothiophene group is substituted or unsubstituted with deuterium, nitrile group, halogen group, or substituted or unsubstituted alkyl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, carbazole group, dibenzofuran group, or dibenzothiophene group is substituted or unsubstituted with an alkyl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are a phenyl group, a biphenyl group, or a dibenzofuran group unsubstituted or substituted with an alkyl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are a phenyl group, a biphenyl group, or a dibenzofuran group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are a phenyl group, a biphenyl group, or a dibenzofuran group, and the phenyl group is a methyl group, ethyl group, propyl group, isopropyl group, butyl group, terbutyl group, pen It is unsubstituted or substituted with a yl group or a hexyl group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are a phenyl group unsubstituted or substituted with any one or more selected from methyl group, ethyl group, propyl group, isopropyl group, and terbutyl group; Biphenyl group; Or a dibenzofuran group.

In the exemplary embodiment of the present specification, A ₁ and A ₂ are a phenyl group unsubstituted or substituted with a terbutyl group; Biphenyl group; Or a dibenzofuran group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or combined with an adjacent group to form a substituted or unsubstituted heterocycle.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently an aryl group; Or a heteroaryl group, or combined with an adjacent group to form a heterocycle,

The aryl group; Or a heteroaryl group, or a heterocycle formed by bonding with an adjacent group is in the group consisting of deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group It is unsubstituted or substituted with one or more selected substituents.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently an aryl group; Or a substituted or unsubstituted heteroaryl group with an aryl group, or combined with an adjacent group to form a substituted or unsubstituted heterocycle.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted with an aryl group, or combined with an adjacent group to form a heterocycle substituted or unsubstituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms unsubstituted or substituted with an aryl group. .

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, Fluorene group, carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, terphenyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, fluorene group, carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group is deuterium, It is unsubstituted or substituted with one or more substituents selected from the group consisting of a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, Fluorene group, carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, terphenyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, fluorene group, carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group is an aryl group. Substituted or unsubstituted.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a naphthyl group, a carbazole group, a benzocarbazole group, a dibenzofuran group, or a dibenzothiophene And

The carbazole group, benzocarbazole group, dibenzofuran group, or dibenzothiophene group is unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; A carbazole group unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; A carbazole group unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group; Biphenyl group; A carbazole group unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group; A carbazole group unsubstituted or substituted with an aryl group; Or a benzocarbazole group unsubstituted or substituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group; A carbazole group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a benzocarbazole group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group; A carbazole group unsubstituted or substituted with a phenyl group, a biphenyl group, or a naphthyl group; Or a benzocarbazole group unsubstituted or substituted with a phenyl group, a biphenyl group, or a naphthyl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group; A carbazole group unsubstituted or substituted with a phenyl group; Or a benzocarbazole group unsubstituted or substituted with a phenyl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other, and each independently a phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ form a substituted heterocycle by bonding with an adjacent group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with an adjacent group to form a substituted N-containing heterocycle.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with adjacent groups to form a substituted N-containing bicyclic heterocycle.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with adjacent groups to form an N-containing bicyclic heterocycle substituted with an aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with adjacent groups to form an N-containing bicyclic heterocycle substituted with a deuterated aryl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with an adjacent group to form an N-containing bicyclic heterocycle substituted with an aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with an adjacent group to form an N-containing bicyclic heterocycle substituted with a deuterated aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with adjacent groups to form an N-containing bicyclic heterocycle substituted with a phenyl group.

In the exemplary embodiment of the present specification, R ₁ and R ₂ are combined with an adjacent group to form an N-containing bicyclic heterocycle substituted with a deuterated phenyl group.

The "deuterated" means that a replaceable hydrogen is substituted with deuterium.

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

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, when a member is said to be positioned "on" another member, this includes not only the case where a member is in contact with the other member, but also the case where another member exists between the two members.

The organic light-emitting device of the present invention includes a first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers may include the aforementioned compound.

For example, the structure of the organic light-emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.

1 illustrates an organic light-emitting device and is not limited thereto.

2 shows a first electrode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), an electron transport layer (7), an electron injection layer (8) and a second electrode ( 4) The structure of the organic light emitting device in which these are sequentially stacked is illustrated. The compound of the present invention is preferably contained in the light emitting layer (3).

In one embodiment of the present invention, the emission layer includes the compound.

In an exemplary embodiment of the present invention, the emission layer includes the compound as a dopant of the emission layer.

In an exemplary embodiment of the present invention, the emission layer may include the compound as a dopant for the emission layer, and may further include an additional dopant.

In an exemplary embodiment of the present invention, the emission layer may include the compound as a dopant for the emission layer, and may further include an additional fluorescent dopant.

In one embodiment of the present invention, the light emitting layer may use a carbazole-based organic compound as a host compound, but is not limited thereto.

In one embodiment of the present invention, the emission layer includes a host and a dopant in a ratio of 95:5 to 10:90.

In one embodiment of the present invention, the emission layer includes a host and a dopant in a ratio of 95:5 to 30:70.

In an exemplary embodiment of the present invention, the emission layer includes a compound represented by the following Formula A as a host.

[Formula A]

In the formula A,

XX1 and XX2 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent Can be combined with the group to form a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted hetero ring,

L101 is each independently a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

x1 is an integer of 0 to 8, and when x1 is 2 or more, XX1 is the same as or different from each other,

x2 is an integer of 0 to 8, and when x2 is 2 or more, XX2 is the same as or different from each other,

m101 is an integer of 1 to 10, and when m101 is 2 or more, L101 is the same as or different from each other.

In the exemplary embodiment of the present specification, L101 is a substituted or unsubstituted arylene group.

In the exemplary embodiment of the present specification, L101 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L101 is an arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present invention, L101 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent naphthyl group, a substituted or unsubstituted divalent anthracene group, a substituted Or an unsubstituted divalent phenanthrene group, a substituted or unsubstituted divalent triphenylene group, a substituted or unsubstituted divalent fluorene group, or a substituted or unsubstituted divalent pyrene group.

In an exemplary embodiment of the present invention, L101 is a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent anthracene group, a divalent phenanthrene group, a divalent triphenylene group, a divalent fluorene group, or a divalent. It's a pyrengi.

In the exemplary embodiment of the present specification, L101 is a divalent biphenyl group.

In the exemplary embodiment of the present specification, L101 is a phenylene group.

In the exemplary embodiment of the present specification, XX1 and XX2 are hydrogen.

In an exemplary embodiment of the present invention, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer contains the compound of Formula 1 I can.

In an exemplary embodiment of the present invention, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound of Formula 1 I can.

In an exemplary embodiment of the present invention, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the compound of 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.

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers is formed using the compound.

The present specification also provides a method of manufacturing an organic light-emitting device formed by using the compound.

For example, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. After depositing an anode to form an anode, an organic material layer including a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an organic material layer including the compound of Formula 1 are formed thereon, and then a material that can be used as a cathode is deposited thereon. It can be produced by 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.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto.

As the hole transport material, a material capable of transporting holes from an anode or a hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

Dopant materials include aromatic compounds, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group, and the styrylamine compound is substituted or unsubstituted The arylamine is a compound in which at least one arylvinyl group is substituted, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer.As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and injects holes of excitons generated from the light emitting layer. A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP (2,9-dimethyl-4, 7-diphenylphenanthroline), aluminum complex, etc., but are not limited thereto.

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

The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compound.

The manufacturing method of the compound of Formula 1 and the manufacturing of an organic light emitting device using the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

In the following reaction scheme, various types of intermediates can be synthesized according to the type and number of substituents appropriately selecting a known starting material by a person skilled in the art. As for the reaction type and reaction conditions, those known in the art may be used.

For example, the compound of Formula 1 may have a core structure as shown in Scheme 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.

When the preparation formula described in the examples of the present specification and the intermediates are appropriately combined based on common technical knowledge, all of the compounds of Formula 1 described in the present specification can be prepared.

Synthesis of Compound A

4-chloro-1-methyl-9-phenyl-9H-carbazole (2.40 g, 6.47 mmol) was dissolved in tetrahydrofuran at -78°C under nitrogen conditions and 2.5M n-BuLi (5.17 mL, 12.9 mmol) Was slowly added dropwise. After stirring at the same temperature for 30 minutes, trimethylborate (3.61 mL, 32.4 mmol) was added, followed by stirring again at the same temperature for 30 minutes. Then, the temperature was raised to room temperature and stirred for 2 hours. After completion of the reaction with 2M HCl, extraction was performed twice with chloroform. The organic layer was washed with water, and the organic layer was then dried over anhydrous sodium sulfate (MgSO ₄ ). Then, after filtering-separated, the solvent was distilled off under reduced pressure, and 1.79g of compounds A were obtained.

MS (APCI) m/z 336.10 (M+H) ⁺ ].

Synthesis of compound A-1

Compound A (4.07 g, 12.10 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.92 g, 10.90 mmol), potassium carbonate (4.90 g, 21.90 mmol) and tetrakis ( Triphenylphosphine)-palladium (0) (0.30 g, 0.30 mmol) was dissolved in tetrahydrofuran and water for 12 hours under reflux reaction to synthesize compound A-1 (3.78g, yield: 68%).

MS (APCI) m/z 508.15 (M+H) ⁺ ]

Synthesis of compound 1

Palladium (II) acetate (0.21 g), xylene (20 mL), and tri-tert-butylphosphine (0.76 g) were added, followed by stirring at 60° C. for 30 minutes. Compound A-1 (5.1 g), 3,6-di-tert-butyl-9H-carbazole (2.8 g) and tert-butoxy sodium 7.7 g (80 mmol) were heated to 60° C. under a nitrogen stream. ) Of xylene (180 mL). Then, the temperature was raised to 130° C., and heated and stirred for 5 hours. After cooling to room temperature, 100 mL of water was added. After the organic layer was extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate (MgSO ₄ ), and the solvent was removed, followed by silica gel column chromatography to obtain Compound 1 (5.3 g, yield: 70%).

MS (APCI) m/z 508.15 (M+H) ⁺ ].

3 is NMR data of Compound 1.

1H NMR (500 MHz, CDCl3-d1): δ 8.57 (t, 4H, J=7.5 Hz), 8.27 (s, 2H),

8.13 (d, 1H, J=8.0 Hz), 7.61 (t, 2H, J=7.0 HZ), 7.55 (t, 5H, J=8.0 Hz), 7.43 (d, 2H, J=8.5 HZ),

7.33 (d, 1H, J=8.0 Hz), 7.31-7.28 (m, 3H), 7.19 (d, 2H, J=8.5 HZ), 6.91-6.85 (m, 4H), 6.75 (d,

1H, J= 8.0 Hz), 1.50 (s, 18H)

Synthesis of compound A-2

2,4-bis(4-(tert-butyl)phenyl)- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (2.92 g, 10.90 mmol) in the synthesis of compound A-1 Compound A-2 (2.90g, yield: 70%) was synthesized in the same manner except that 6-chloro-1,3,5-triazine was used. MS (APCI) m/z 379.18 (M+H) ⁺ ].

Synthesis of compound 2

In the synthesis of compound 1, compound A-2 was substituted for compound A-1 (5.1 g) and 3,6-diphenyl-9H-carbazole was substituted for 3,6-di-tert-butyl-9H-carbazole (2.8 g) Except for using the compound 2 (4.90g, yield: 62%) was synthesized in the same manner.

MS (APCI) m/z 791.30 (M+H) ⁺ ].

Synthesis of compound A-3

In the synthesis of compound A-1, 2-([1,1'-biphenyl]-4-yl instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (2.92 g, 10.90 mmol) Compound A-3 (4.59g, yield: 72%) was synthesized in the same manner except for using )-4-chloro-6-phenyl-1,3,5-triazine. MS (APCI) m/z 584.18 (M+H) ⁺ ]

Synthesis of compound 3

In the synthesis of compound 1, compound A-3 was used instead of compound A-1 (5.1 g), and 9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole (2.8 g). Compound 3 (4.30g, yield: 60%) was synthesized by the method. MS (APCI) m/z 715.27 (M+H) ⁺ ].

Synthesis of compound 4

In the synthesis of compound 1, A-3 was used instead of compound A-1 (5.1 g), and 9-phenyl-9H,9'H- instead of 3,6-di-tert-butyl-9H-carbazole (2.8 g) Compound 4 (4.97g, yield: 52%) was synthesized in the same manner except that 3,3'-biscarbazole was used.

MS (APCI) m/z 956.36 (M+H) ⁺ ].

Synthesis of compound A-5

In the synthesis of compound A-1, 2-chloro-4-(dibenzo[b,d]furan- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (2.92 g, 10.90 mmol) Compound A-5 (4.43g, yield: 68%) was synthesized in the same manner except that 3-yl)-6-phenyl-1,3,5-triazine was used. MS (APCI) m/z 598.16 (M+H) ⁺ ].

Synthesis of compound 5

In the synthesis of compound 1, compound A-5 was used instead of compound A-1 (5.1 g), and 5H-benzo[b] carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole (2.8 g). Except for the same method, compound 5 (4.83g, yield: 62%) was synthesized. MS (APCI) m/z 779.27 (M+H) ⁺ ].

Synthesis of compound 6

In the synthesis of compound 1, compound A-1 (5.1 g) was used, and 9-phenyl-9H,9'H-3,3' instead of 3,6-di-tert-butyl-9H-carbazole (2.8 g) -Compound 6 (4.97g, yield: 52%) was synthesized in the same manner except that biscarbazole was used. MS (APCI) m/z 880.33 (M+H) ⁺ ].

4 is NMR data of compound 6.

1H NMR (500 MHz, CDCl3): δ 8.60-8.58 (m, 5H), 8.51 (s, 1H), 8.39 (d,

1H, J=8.0 Hz), 8.26 (d, 1H, J=7.5 HZ), 8.18 (d, 1H, J=7.5 Hz), 7.83 (d, 1H, J=8.5 HZ), 7.77

(d, 1H, J=8.5 Hz), 7.65-7.61 (m, 7H), 7.57-7.53 (m, 5H), 7.51-7.47 (m, 1H), 7.45-7.30 (m,

11H), 6.91-6.88 (m, 4H), 6.75 (d, 1H, J=8.0 HZ)

Synthesis of compound B

3-chloro-1-methyl-9-phenyl-9H-carbazole (2.40 g, 6.47 mmol) was dissolved in tetrahydrofuran at -78 °C under nitrogen conditions and 2.5M n-BuLi (5.17 mL, 12.9 mmol) Was slowly added dropwise. After stirring at the same temperature for 30 minutes, trimethylborate (3.61 mL, 32.4 mmol) was added, followed by stirring again at the same temperature for 30 minutes. Then, the temperature was raised to room temperature and stirred for 2 hours. After completion of the reaction with 2M HCl, extraction was performed twice with chloroform. The organic layer was washed with water, and the organic layer was then dried over anhydrous sodium sulfate (MgSO ₄ ). Then, after filtration separation, the solvent was distilled off under reduced pressure to obtain 1.70 g of Compound B.

MS (APCI) m/z 336.10 (M+H) ⁺ ].

Synthesis of compound B-1

In the synthesis of compound A-1, compound B-1 (3.94 g, yield: 64%) was synthesized in the same manner, except that compound B was used instead of compound A (4.07 g, 12.10 mmol). MS (APCI) m/z 508.15 (M+H) ⁺ ].

Synthesis of compound 7

In the synthesis of compound 1, compound 7 (4.51 g, yield: 60%) was synthesized in the same manner, except that compound B-1 was used instead of compound A-1 (5.1 g). MS (APCI) m/z 751.37 (M+H) ⁺ ].

Synthesis of compound B-2

2,4-bis(4-(tert-butyl)phenyl)- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (2.92 g, 10.90 mmol) in the synthesis of compound B-1 Compound B-2 (2.90g, yield: 70%) was synthesized in the same manner except that 6-chloro-1,3,5-triazine was used. MS (APCI) m/z 379.18 (M+H) ⁺ ].

Synthesis of compound 8

In the synthesis of compound 1, compound B-2 was substituted for compound A-1 (5.1 g), and 3,6-diphenyl-9H-carbazole was substituted for 3,6-di-tert-butyl-9H-carbazole (2.8 g) Except for using the compound 8 (5.79g, yield: 64%) was synthesized in the same manner. MS (APCI) m/z 903.43 (M+H) ⁺ ].

Synthesis of compound 9

In the synthesis of compound 1, compound B-1 was substituted for compound A-1 (5.1 g), and 9-phenyl-9 H ,9′ H -instead of 3,6-di-tert-butyl-9H-carbazole (2.8 g) Compound 9 (6.16g, yield: 70%) was synthesized by the same method except that 3,3'-bicarbazole was used.

MS (APCI) m/z 880.33 (M+H) ⁺ ].

Synthesis of compound 10

In the synthesis of compound 1, compound B-1 was used instead of compound A-1 (5.1 g), and 5H-benzo[b] carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole (2.8 g). Except for the same method, compound 10 (4.27g, yield: 62%) was synthesized.

MS (APCI) m/z 689.26 (M+H) ⁺ ].

Synthesis of compound C

1-Bromo-6-chloro-9-phenyl-9H-carbazole (2.40 g, 6.47 mmol) was dissolved in tetrahydrofuran at -78°C under nitrogen conditions and 2.5M n-BuLi (5.17 mL, 12.9 mmol) ) Was slowly added dropwise. After stirring at the same temperature for 30 minutes, trimethylborate (3.61 mL, 32.4 mmol) was added, followed by stirring again at the same temperature for 30 minutes. Then, the temperature was raised to room temperature and stirred for 2 hours. After completion of the reaction with 2M HCl, the mixture was extracted twice with chloroform. The organic layer was washed with water, and then the obtained organic layer was dried over anhydrous sodium sulfate (MgSO ₄ ). Then, after filtering-separated, the solvent was distilled off under reduced pressure, and 1.92 g of compound C was obtained.

MS (APCI) m/z 336.10 (M+H) ⁺ ].

Synthesis of compound C-1

In the synthesis of compound A-1, compound C-1 (4.30 g, yield: 70%) was synthesized in the same manner, except that compound C was used instead of compound A (4.07 g, 12.10 mmol). MS (APCI) m/z 508.15 (M+H) ⁺ ].

Synthesis of compound 11

In the synthesis of compound 1, compound C-1 was used instead of compound A-1 (5.1 g), and 3-phenyl-9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole (2.8 g). Except for the same method, compound 11 (4.15g, yield: 58%) was synthesized. MS (APCI) m/z 715.27 (M+H) ⁺ ].

Synthesis of compound 12

In the synthesis of compound 1, compound C-1 was substituted for compound A-1 (5.1 g), and 9H-3,9'-bicarbazole was substituted for 3,6-di-tert-butyl-9H-carbazole (2.8 g). Compound 12 (4.83g, yield: 60%) was synthesized in the same manner except that it was used.

MS (APCI) m/z 804.30 (M+H) ⁺ ].

Synthesis of compound C-2

In the synthesis of compound A-1, compound C was used instead of compound A (4.07 g, 12.10 mmol), and instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (2.92 g, 10.90 mmol) 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine was used in the same manner, except that compound C-2 (4.43 g, Yield: 68%) was synthesized.

MS (APCI) m/z 598.16 (M+H) ⁺ ].

Synthesis of compound 13

In the synthesis of compound 1, compound C-2 was used instead of compound A-1 (5.1 g), and 9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole (2.8 g). Compound 13 (4.38g, yield: 60%) was synthesized by the method.

MS (APCI) m/z 729.25 (M+H) ⁺ ].

Synthesis of compound 14

In the synthesis of compound 1, compound C-2 was used instead of compound A-1 (5.1 g), and 3-phenyl-9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole (2.8 g). Except for the same method, compound 14 (5.48g, yield: 68%) was synthesized. MS (APCI) m/z 7805.28 (M+H) ⁺ ].

Example 1

After patterning so that the light emitting area of the ITO (indium tin oxide) glass had a size of 3 mm × 3 mm, it was washed. After mounting the substrate in a vacuum chamber, make the base pressure 1x10 ^-6 torr, and then form HT-1 with a thickness of 100Å as a hole injection layer on the anode ITO, but compound A-1 with a doping concentration of 25% by weight. Doped. Subsequently, HT-1 was formed to a thickness of 600 Å as a hole transport layer, and 1,3-bis (N-carbazolyl) benzene (1,3-bis (N-carbazolyl) benzene (mCP)) was formed to a thickness of 50 Å. I did. Next, the compound 1 of Synthesis Example 1 was used as a dopant in m-CBP as a host as a light emitting layer, deposited so that the weight ratio was 8:2, and diphenyl[4-(triphenylsilyl)phenyl]phosphine was used as an electron transport layer. Oxide (diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide)(TSPO1, 5 nm)/ 2,2′,2″-(1,3,5-benzointriyl)-tris(1-phenyl-1-H -Benzimidazole) (2,2′,2″-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole))(TPBi, 20 nm was deposited as an electron injection layer. LiF was formed to a thickness of 10 Å, and Al was sequentially formed to a thickness of 800 Å as a cathode to fabricate an organic light emitting device.

Example 2

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 2 instead of Compound 1.

Example 3

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 3 instead of Compound 1.

Example 4

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 4 instead of Compound 1.

Example 5

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 5 instead of Compound 1.

Example 6

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 6 instead of Compound 1.

Example 7

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 7 instead of Compound 1.

Example 8

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 8 instead of Compound 1.

Example 9

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 9 instead of Compound 1.

Example 10

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 10 instead of Compound 1.

Example 11

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 11 instead of Compound 1.

Example 12

Under the same process conditions as in Example 1, only using Compound 12 instead of Compound 1 was used to manufacture an organic light-emitting device.

Example 13

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 13 instead of Compound 1.

Example 14

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Compound 14 instead of Compound 1.

Comparative Example 1

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Comparative Compound 1 instead of Compound 1.

[Comparative compound 1]

Comparative Example 2

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by using only Comparative Compound 2 instead of Compound 1.

[Comparative compound 2]

Comparative Example 3

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Comparative Compound 3 instead of Compound 1.

[Comparative compound 3]

Comparative Example 4

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Comparative Compound 4 instead of Compound 1.

[Comparative compound 4]

Comparative Example 5

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by only using Comparative Compound 5 instead of Compound 1.

[Comparative compound 5]

Comparative Example 6

Under the same process conditions as in Example 1, an organic light-emitting device was manufactured by using only Comparative Compound 6 instead of Compound 1.

[Comparative compound 6]

Voltage, efficiency, and lifetime (T95) were measured by applying a current to the organic light emitting devices prepared in Examples 1 to 14 and Comparative Examples 1 to 6, respectively, and the results are shown in Table 1 below. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and the lifetime (T95) means the time until the initial luminance at 3,000 nit decreases to 95%.

Voltage (V) (@10mA/cm ² ) Efficiency (cd/A) (@10mA/cm ² ) Life (T95, hr) Example 1 4.4 47.2 326 Example 2 4.4 47.0 360 Example 3 4.2 42.4 342 Example 4 4.4 41.6 346 Example 5 4.4 45.4 400 Example 6 4.3 45.8 312 Example 7 4.4 44.0 320 Example 8 4.2 42.4 300 Example 9 4.5 44.8 340 Example 10 4.2 45.0 320 Example 11 4.4 45.2 300 Example 12 4.2 45.8 280 Example 13 4.4 46.0 280 Example 14 4.4 45.0 268 Comparative Example 1 4.8 30.8 200 Comparative Example 2 4.8 30.8 180 Comparative Example 3 5.0 38.6 180 Comparative Example 4 5.0 36.6 200 Comparative Example 5 5.0 36.2 180 Comparative Example 6 4.8 36.0 164

As shown in the above table, Examples 1 to 14 in which the compound of Formula 1 of the present invention was used as a dopant for the light emitting layer of an organic light emitting device exhibited superior properties compared to Comparative Examples 1 to 6.

Specifically, compared to Comparative Examples 1, 2, 4, and 5 that do not contain a heteroarylene linker, Examples 1 to 14 showed excellent effects of low voltage, high efficiency, and long life.

Even when compared with Comparative Examples 3 and 6 using a heteroarylene (dibenzofuran) linker that does not contain N, it can be seen that Examples 1 to 14 have excellent effects of low voltage, high efficiency, and long life.

Example 15

After patterning so that the light emitting area of the ITO (indium tin oxide) glass had a size of 3 mm × 3 mm, it was washed. After mounting the substrate in a vacuum chamber, the base pressure was 1x10 ^-6 torr, and then the HT-1 was formed to a thickness of 100Å as a hole injection layer on the anode ITO, but the compound 1 was used at a doping concentration of 25% by weight. Doped. Subsequently, HT-1 was formed to a thickness of 600 Å as a hole transport layer, and 1,3-bis(N-carbazolyl)benzene (mCP) was formed to a thickness of 50 Å. Next, the compound 1 and the fluorescent dopant compound-D were deposited to a weight ratio of 79:20:1 using m-CBP as a dopant as a light emitting layer, and diphenyl[4-(triphenylsilyl)phenyl as an electron transport layer. ] Phosphine oxide (TSPO1, 5 nm)/2,2′,2″-(1,3,5-benzointriyl) -tris(1-phenyl-1-H-benzimidazole) (TPBi, 20 nm LiF was formed as an electron injection layer to a thickness of 10 Å, and Al was sequentially formed as a cathode to a thickness of 800 Å, thereby fabricating an organic light emitting device.

[Compound-D]

Example 16

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by only using Compound 3 instead of Compound 1.

Example 17

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by only using Compound 6 instead of Compound 1.

Example 18

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by only using Compound 14 instead of Compound 1.

Comparative Example 7

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by only using Comparative Compound 1 instead of Compound 1.

Comparative Example 8

Under the same process conditions as in Example 15, an organic light-emitting device was manufactured by using only Comparative Compound 3 instead of Compound 1.

Voltage, efficiency, and lifetime (T95) were measured by applying current to the organic light-emitting devices prepared in Examples 15 to 18 and Comparative Examples 7 and 8, respectively, and the results are shown in Table 2 below. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and the lifetime (T95) means the time until the initial luminance at 3,000 nit decreases to 95%.

Voltage (V)
(@10mA/cm ² ) Efficiency (cd/A) (@10mA/cm ² ) Life (T95, hr) Example 15 4.4 49.0 346 Example 16 4.2 44.8 364 Example 17 4.3 47.8 330 Example 18 4.4 45.8 300 Comparative Example 7 4.8 28.8 180 Comparative Example 8 5.0 35.6 160

As shown in Table 2, Examples 15 to 18, in which the compound of Formula 1 of the present invention was used as a dopant for the emission layer of an organic light emitting diode, exhibited superior properties compared to Comparative Examples 7 and 8. In particular, it was confirmed that efficiency and lifespan were improved through the N-containing polycyclic heteroaryl structure of Formula 1 and the N-type and P-type units.

In addition, comparing Tables 1 and 2, compared to Examples 1, 3, 6, and 14 in which the compound of Formula 1 was used alone as the dopant material of the emission layer of the organic light-emitting device, Examples 15 to 18 using a fluorescent dopant at the same time. It was confirmed that the efficiency and lifetime of the organic light emitting device were improved. On the other hand, when comparing the results of Comparative Examples 1 and 3 with Comparative Examples 7 and 8, it could not be confirmed that the efficiency and lifespan were improved in Comparative Examples 7 and 8 despite the simultaneous use of the fluorescent dopant.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electron transport layer
8: electron injection layer

Claims (8)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
L is a divalent substituted or unsubstituted N-containing polycyclic heteroaryl,
A ₁ and A ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
X ₁ to X ₃ are the same as or different from each other, and each independently N or CR,
At least one of X ₁ to X ₃ is N,
R is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group,
R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, Combined with adjacent groups to form a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaryl
a and b are each an integer of 0 to 4,
When a or b is plural, the substituents in parentheses are the same as or different from each other. The compound according to claim 1, wherein L is a divalent N-containing polycyclic heteroaryl unsubstituted or substituted with an aryl group. The compound of claim 1, wherein A ₁ and A ₂ are a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. The method according to claim 1, wherein R ₁ and R ₂ are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted with an aryl group, or a compound which is combined with an adjacent group to form a substituted or unsubstituted heterocycle with an aryl group. The compound of claim 1, wherein Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided opposite to the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound of any one of claims 1 to 5 Light-emitting element. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the compound as a dopant of the emission layer, and further includes an additional fluorescent dopant.

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