CN116751229B

CN116751229B - An OLED luminescent organic material and its OLED luminescent device

Info

Publication number: CN116751229B
Application number: CN202310672690.4A
Authority: CN
Inventors: 王湘成; 王鹏; 何睦
Original assignee: Shanghai Yaoyi Electronic Technology Co ltd
Current assignee: Shanghai Yaoyi Electronic Technology Co ltd
Priority date: 2023-06-07
Filing date: 2023-06-07
Publication date: 2025-12-30
Anticipated expiration: 2043-06-07
Also published as: CN116751229A

Abstract

This invention relates to the field of organic light-emitting diode (OLED) technology, particularly to IPC C07, and more specifically to an OLED light-emitting organic material and an OLED light-emitting device thereof. In this invention, the OLED light-emitting organic material comprises a naphthyl aliphatic ring structure, which enhances the electron-donating ability of the molecule, thereby improving electron migration ability, stabilizing holes, and further improving molecular stability. When the compound of this invention is applied to organic electroluminescent devices, it enables the device to possess high efficiency, while the molecule exhibits high stability, further improving the luminous efficiency and lifespan of the device.

Description

OLED luminescent organic material and OLED luminescent device thereof

Technical Field

The invention relates to the technical field of organic light emitting diodes, in particular to an IPC C07, and more particularly relates to an OLED light emitting organic material and an OLED light emitting device thereof.

Background

The Organic Light Emitting Diode (OLED) has the characteristics of low energy consumption, light weight, wide visual angle, quick response, active luminescence and the like, and is widely applied and developed in the fields of weaponry, electric appliances and severe environments, in particular to a planar light source or a lighting source in the display field of electric appliances.

With the continuous development of the organic light emitting diode OLED, the application range increases, and the requirements on performances of various aspects of the organic light emitting diode OLED are higher and higher. Naphthalene is widely used as a material segment commonly used in OLED devices, and is widely used as a hole transport material, a luminescent layer material and an electron transport layer material. Naphthalene has a larger conjugation plane, can form a better conjugation effect when being connected with other groups, and has a very good effect on the stability of molecules.

The prior patent CN201911129807.4 is a nitrogen-containing hetero seven-membered ring carbazole organic luminescent material and application thereof. The organic luminescent material structure takes nitrogen-containing heteroseven-membered ring carbazole as a main body, and the structural general formula of the organic luminescent material is shown as a formula I, wherein R is benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, pyrene, binaphthyl, bianthracene, fluoranthene, benzanthracene, fluorene, benzofluorene, N-phenylcarbazole, N-naphthylcarbazole, N-phenylbenzocarbazole, dibenzofuran or dibenzothiophene. When the nitrogen-containing hetero-seven-membered ring carbazole organic luminescent material is applied to the manufacture of OLED devices and is used as a main luminescent material or an electron transport material, the external quantum efficiency, the power efficiency and the current efficiency of the OLED devices are greatly improved, so that the service life of the OLED devices is obviously prolonged, the good market prospect is achieved, but the pi-pi effect among molecules is strong due to the flatness of naphthalene, the problems of high sublimation temperature, easiness in crystallization and the like are caused, and the evaporation temperature and the film stability of the organic luminescent material are still to be improved.

Disclosure of Invention

In order to solve the problems in the prior art, a first aspect of the present invention provides an OLED light-emitting organic material, including the structure shown in formula 1.

In the formula 1, R ₁～R₆ represents a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; Y is independently selected from hydrogen atom, metal atom, amino, hydroxyl, mercapto, C1-C30 alkyl, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, wherein the hydrogen atom, metal atom, amino, hydroxy, mercapto, C1-C30 alkyl, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl may be substituted with 0 or any substituent selected from the group A, wherein the substituent of the substituent group A is selected from hydrogen atom, metal atom, amino, hydroxy, mercapto, C1-C30 alkyl, C3-C30 cycloalkyl, C2-C30 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, wherein the substituent of the substituent group A may be further substituted with 0 or any substituent group B, and the substituent of the substituent group B may be selected from the group B, wherein the substituent group B is further selected from the group C1-C30 cycloalkyl, C3-C30 cycloalkyl, C2-C30 cycloalkyl, C6-C30 cycloalkyl, C3-C30 heteroaryl, C3-C30 cycloalkyl, C3-C30 aryl, C3-C30 heteroaryl, C3-C30 cycloalkyl, C30C 3-C30 cycloalkyl, C3-C30 aryl The substituent group C can be further substituted by 0 or any substituent group selected from the substituent group D, the substituent group of the substituent group D is selected from hydrogen atoms, metal atoms, amino groups, hydroxyl groups, mercapto groups, C1-C30 alkyl groups, C3-C30 cycloalkyl groups, C2-C30 heterocycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, m is 1-4, any one or more of the substituent groups of the substituent group A, B, C, D and Y can be connected into an aliphatic ring, a heterocyclic ring, an aromatic ring or a heteroaromatic ring through any bond, and all hydrogen atoms in the formula 1 can be substituted by deuterium atoms or C1-C12 alkyl groups, C3-C12 cycloalkyl groups, C2-C12 heterocycloalkyl groups and C6-C12 aryl groups.

Preferably, the OLED light-emitting organic material includes a hole transport layer material, a light-emitting layer material, and an electron transport layer material.

Preferably, the luminescent layer material comprises a fluorescent luminescent layer material or a phosphorescent luminescent layer material, the fluorescent luminescent layer material comprises a blue fluorescent luminescent host material, the phosphorescent luminescent layer material comprises a phosphorescent luminescent host material and a phosphorescent luminescent guest material, the phosphorescent luminescent host material is a red phosphorescent luminescent host material, and the phosphorescent luminescent guest material is a red phosphorescent luminescent guest material.

Preferably, the hole transport layer material has a structure represented by any one of formulas 2, 3, and 4.

Preferably, the structure of formula 2 is

In the formula 2, R ₁～R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra is selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, m is 0-3, L ₁、L₂、L₃ is selected from single bond, substituted or unsubstituted C6-C30 arylene groups or substituted or unsubstituted C3-C30 heteroarylene groups, ar ₁,Ar₂ is independently selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C30 heteroaryl groups, all hydrogen atoms in the formula 2 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups, wherein substituents are the same or different and are independently selected from hydrogen atoms, halogen atoms, cyano groups, nitro groups, trifluoromethyl groups, methoxy groups, ethoxy groups, methylthio groups, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, C3-C20 heteroaryl groups, phenyl groups, and tert-phenyl groups.

Further preferably, the hole transport layer material has a structure of

In formula 2-1, R ₁～R₇ is independently selected from hydrogen atom and methyl; L ₁、L₂、L₃ is selected from single bond, substituted or unsubstituted C6-C20 arylene or substituted or unsubstituted C3-C20 heteroarylene; preferably, the C6-C20 arylene and C3-C20 heteroarylene in L ₁、L₂、L₃ are phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, carbazolylene, dibenzothienyl and dibenzofuranylene; ar ₁,Ar₂ is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, preferably, the C6-C30 aryl or C3-C30 heteroaryl in Ar ₁,Ar₂ is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl, spirofluorenyloxy, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzofluorenyl, benzocarbazolyl, benzonaphthothiophenyl, benzonaphthofuranyl, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, wherein the substituents in the formula are the same or different and are independently selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, butanyl, pyrazinyl, quinolinyl, quinoxalinyl, pyrrolyl, C1-C6 alkyl, and C1-C6 alkyl groups.

Preferably, the structure of formula 3 is

In the formula 3, R ₁～R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra and Rb are independently selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl or heterocycloalkyl groups, C6-C30 aryl groups and C3-C30 heteroaryl groups; X is selected from CR ₇R₈、NR₉、O、S,R₇-R₉ and is selected from hydrogen atom, C1-C30 alkyl, C3-C30 cycloalkyl and C2-C30 heterocycloalkyl, R ₇-R₈ can be connected into an aliphatic ring through any bond, m is 0-2, p is 0-3, L is selected from single bond, substituted or unsubstituted arylene of C6-C30 or substituted or unsubstituted C3-C30 heteroarylene, ar ₁,Ar₂ is selected from substituted or unsubstituted aryl of C6-C30 or substituted or unsubstituted C3-C30 heteroaryl, all hydrogen atoms in the formula 3 can be substituted by deuterium atom, C1-C6 alkyl, C3-C6 cycloalkyl or heterocycloalkyl, wherein substituents are the same or different and are independently selected from hydrogen atom, halogen atom, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C20 heteroaryl, phenyl and tert-phenyl.

Further preferably, the hole transport layer material has a structure of

In the formula 3-1, R ₁～R₆ is independently selected from a hydrogen atom and a methyl group, n is 1 or 2, X is selected from CR ₇R₈、NR₉、O、S,R₇-R₉ and is selected from a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group and a C2-C6 heterocycloalkyl group, and R ₇-R₈ can be connected into an alicyclic ring through any bond; L is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C20 heteroarylene group; preferably, the C6-C20 arylene and C3-C20 heteroarylene in the L are phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, carbazolylene, dibenzothiophenylene and dibenzofuranylene; ar ₁,Ar₂ is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, preferably, the C6-C30 aryl or C3-C30 heteroaryl in Ar ₁,Ar₂ is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzofluorenyl, benzocarbazolyl, benzonaphthothienyl, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, wherein the substituents in the formula are the same or different and are independently selected from hydrogen, fluoro, chloro, bromo, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, butanyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinolinyl, quinoxalinyl, and the substituents in the formula are the same or different, quinoxalinyl, wherein all hydrogen atoms in the formula 3-1 can be replaced by deuterium atoms and C1-C6 alkyl groups.

Preferably, the structure of formula 4 is

R ₁～R₆ is independently selected from hydrogen atom, substituted or unsubstituted C1-C4 alkyl, n is 1 or 2, ra represents hydrogen atom, C1-C30 alkyl, C3-C30 cycloalkyl or heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl; X is selected from the group consisting of a hydrogen atom, a C1-C30 alkyl group, a C3-C30 cycloalkyl group and a C2-C30 heterocycloalkyl group, R ₁₉-R₂₀ can be connected with any bond to form an aliphatic ring, m is selected from the group consisting of 0-2, R ₇～R₁₈ is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group or a heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group,At least one of R ₇～R₁₈ isL is selected from single bond, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene, ar ₁,Ar₂ is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl. All hydrogen atoms in the formula 4 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups, wherein substituents are the same or different and are independently selected from hydrogen atoms, halogen atoms, cyano groups, nitro groups, trifluoromethyl groups, methoxy groups, ethoxy groups, methylthio groups, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, C2-C6 heterocycloalkyl groups, C6-C20 aryl groups, C3-C20 heteroaryl groups, tolyl groups and tert-butylphenyl groups.

Further preferably, the hole transport layer material has a structure of

In the formula 4-1, R ₁～R₆ is independently selected from a hydrogen atom and a methyl group, n is 1 or 2, X is selected from none, X is selected from CR ₁₉R₂₀、NR₂₁、O、S,R₁₉-R₂₁ and is selected from a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 heterocycloalkyl group, and R ₁₉-R₂₀ can be connected into an alicyclic ring through any bond; R ₇～R₁₈ is selected from a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C3-C6 cycloalkyl or heterocycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C3-C12 heteroaryl group,At least one of R ₇～R₁₈ isL is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C20 heteroarylene group; preferably, the C6-C20 arylene and C3-C20 heteroarylene in the L are phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, carbazolylene, dibenzothiophenylene and dibenzofuranylene; ar ₁,Ar₂ is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl; preferably, the C6-C30 aryl or C3-C30 heteroaryl in Ar ₁,Ar₂ is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzocarbazolyl, benzonaphthothiophenyl, benzonaphthofuranyl, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl and quinoxalinyl, wherein the substituents are the same or different and are independently selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl and quinoxalinyl, and the substituents in the formula are all substituted by hydrogen atoms of C1-C6-C1 alkyl.

Preferably, the structure of the hole transport material is shown in HT 1-HT 36:

Preferably, the electron transport layer material has a structure represented by any one of formulas 5, 6, and 7.

Preferably, the structure of formula 5 is

In the formula 5, R ₁～R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra represents hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, m is selected from 0-2, L is selected from single bonds, substituted or unsubstituted C6-C30 arylene groups or substituted or unsubstituted C3-C30 heteroarylene groups, all hydrogen atoms in the formula 5 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups, wherein substituents are the same or different and are independently selected from hydrogen atoms, halogen atoms, cyano groups, nitro groups, trifluoromethyl groups, methoxy groups, ethoxy groups, methylthio groups, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, C2-C6 heterocycloalkyl groups, C6-C20 aryl groups, C3-C20 heteroaryl groups, and tert-butyl groups.

Further preferably, the electron transport layer material has a structure of

In formula 5-1, R ₁～R₇ is independently selected from a hydrogen atom and a methyl group; ra is selected from hydrogen atom and phenyl; m is 1,2 or 3;L is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C20 heteroarylene group; preferably, the C6-C20 arylene and C3-C20 heteroarylene in L are phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, carbazolylene, dibenzothiophenylene, dibenzofuranylene, X ₁,X₂,X₃ are each independently C or N, ar ₁,Ar₂ is each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, C6-C30 aryl or C3-C30 heteroaryl in Ar ₁,Ar₂ is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl, carbazolyl, dibenzothiophenyl, dibenzofuranyl, benzocarbazolyl, benzonaphtalenyl, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, pyrrolyl, pyridinyl, C1-C6 alkyl.

Preferably, the structure of formula 6 is

In the formula 6, R ₁～R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra and Rb are independently selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkylene or heterocycloalkyl groups, C6-C30 aryl groups and C3-C30 heteroaryl groups, X is selected from CR ₇R₈、NR₉、O、S,R₇-R₉ and is selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups and C2-C30 heterocycloalkyl groups, R ₇-R₈ can be connected into an aliphatic ring through any bond, m is 0-2, p is 0-3, L is selected from single bond, substituted or unsubstituted C6-C30 arylene groups or substituted or unsubstituted C3-C30 heteroarylene groups, all hydrogen atoms in the formula 6 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups, and substituents in the formula 6 are identical or different, and are independently selected from hydrogen atoms, halogen atoms, nitro groups, C3-C20 methyl groups, methoxymethyl groups, C20-C6 heteroaryl groups, phenyl groups, C20-C6 heteroaryl groups and the like.

Further preferably, the electron transport layer material has a structure of

In formula 6-1, each R ₁～R₇ is independently selected from a hydrogen atom, a methyl group; ra is selected from hydrogen atom and phenyl; m is selected from 0 to 2; preferably 0,1, 2, X is selected from CR ₇R₈、NR₉、O、S,R₇-R₉ is selected from hydrogen atom, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, R ₇-R₈ can be connected with any bond to form an aliphatic ring, L is selected from single bond, substituted or unsubstituted C6-C20 arylene or substituted or unsubstituted C3-C20 heteroarylene, preferably C6-C20 arylene and C3-C20 heteroarylene in L are selected from phenylene, biphenylene, terphenyl, naphthylene, fluorenylene, carbazolylene, dibenzothienyl, dibenzofuranylene, X ₁,X₂,X₃ is each independently C or N, ar ₁,Ar₂ is each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, C6-C30 aryl or C3-C30 heteroaryl in Ar ₁,Ar₂ is preferably selected from phenyl, terphenyl, naphtylene, pyrrolopyranyl, pyrrolyl, etc., and the like, wherein X may be selected from the formula, and may be optionally bonded to be optionally bonded to be one with any one or optionally with an optional bond, and may be attached, and optionally, and may be bonded, and optionally, and may be selected, and optionally, selected, and be selected from 0, and optionally, and be selected, and optionally, and optionally, and C and C, and C, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, wherein all hydrogen atoms in formula 6-1 may be replaced by deuterium atoms, C1-C6 alkyl groups.

Preferably, the structure of formula 7 is

In the formula 7, R ₁～R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra represents hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, X is selected from CR ₁₉R₂₀、NR₂₁、O、S,R₁₉-R₂₁, is selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups and C2-C30 heterocycloalkyl groups, R ₁₉-R₂₀ can be connected into an aliphatic ring through any bond, and m is selected from 0-2, R ₇～R₁₈ is selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, R ₁₉-R₂₀ and R is selected from hydrogen atoms, substituted or unsubstituted C3-C30 heteroaryl groups,At least one of R ₇～R₁₈ isL is selected from single bond, substituted or unsubstituted arylene of C6-C30 or heteroarylene of C3-C30, all hydrogen atoms in the formula 7 can be substituted by deuterium atoms, alkyl of C1-C6, cycloalkyl of C3-C6 or heterocycloalkyl, and substituent groups in the formula are the same or different and are independently selected from hydrogen atoms, halogen atoms, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, tolyl and tert-butylphenyl.

Preferably, the method comprises the steps of, electron acceptor in the formulas 5,6 and 7 are each independently selected from naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, fluoranthryl, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxanyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinopyrazinyl, pyrazinopyrazinyl, triazinyl, naphthyridinyl, phenanthridinyl, naphthyridinyl, and the like benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoloquinazolinyl, benzimidazolophenidinyl, spiro [ fluorene-9, 9' -xanthene ], benzobinaphthyl, dinaphthofuranyl, naphthafuranyl, dinaphthiothienyl, naphthabenzothiophenyl, triphenylphosphine oxide, triphenylborane, 1-10 phenanthroline, cyano-substituted aryl or heteroaryl, fluoro-substituted aryl or heteroaryl, trifluoromethyl-substituted aryl or heteroaryl.

Further preferably, the electron transport layer material has a structure of

Formula 7-1, R ₁～R₆ are each independently selected from a hydrogen atom, a methyl group, n is 1 or 2, ra is selected from a hydrogen atom or a phenyl group, X is selected from none, CR ₁₉R₂₀、NR₂₁、O、S,R₁₉-R₂₀ is selected from a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 heterocycloalkyl group, R ₁₉-R₂₀ may be linked to form an aliphatic ring by any bond, R ₇～R₁₈ is selected from a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted C3-C6 cycloalkyl group or a heterocycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, a substituted or unsubstituted C3-C12 heteroaryl group,At least one of R ₇～R₁₈ isL is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C20 heteroarylene group; preferably, the C6-C20 arylene and C3-C20 heteroarylene in the L are phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, carbazolylene, dibenzothiophenylene and dibenzofuranylene; each X ₁,X₂,X₃ is independently C or N, and at least one of them is N; ar ₁,Ar₂ is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, C6-C30 aryl or C3-C30 heteroaryl in Ar ₁,Ar₂ is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl, spirofluorenyloxy, carbazolyl, dibenzothienyl, dibenzofuranyl, benzofluorenyl, benzocarbazolyl, benzonaphthothienyl, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl and quinoxalinyl, wherein substituents in the formula are the same or different and are independently selected from hydrogen, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, N-propyl, isopropyl, N-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, phenylbutadienyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinolinyl and quinoxalinyl, wherein the substituents in the formula are all substituted by hydrogen, fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl, thiomethyl, ethyl, N-propyl, isopropyl, N-butyl, tert-butyl, cyclobutyl, cyclohexyl, pyridinyl, quinolinyl, C1-C6 alkyl, and the like.

Preferably, the specific structure of the electron transport layer material is shown as E1-E24.

Preferably, the red phosphorescent host material has a structure represented by any one of formulas 8 and 9.

Preferably, the structure of formula 8 is

In the formula 8, R ₁～R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra and Rb are independently selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups and C3-C30 heteroaryl groups, rb can be connected into an aliphatic ring, heterocycle, aromatic ring or heteroaromatic ring through any bond, m is 0-2, p is 0-3, ar ₁,Ar₂ is independently selected from hydrogen atoms, substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C30 heteroaryl groups, all hydrogen atoms in the formula 8 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups, wherein substituents are the same or different and are independently selected from hydrogen atoms, halogen atoms, cyano groups, nitro groups, trifluoromethyl groups, methoxy groups, ethoxy groups, methylthio groups, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, C20 heteroaryl groups, phenyl groups and tert-20-phenyl groups.

Further preferably, the red phosphorescent host material has a structure of

In the formula 8-1, R ₁～R₆ is independently selected from a hydrogen atom, a methyl group, n is 1 or 2, rb is independently selected from a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl or heterocycloalkyl group, a C6-C20 aryl group and a C3-C20 heteroaryl group; rb can be connected into an aliphatic ring, a heterocycle, an aromatic ring or a heteroaromatic ring through any bond; p is 0 to 3, preferably 0, 1,2, 3; the Ar ₁,Ar₂ is independently selected from hydrogen atoms, substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C30 heteroaryl groups, the C6-C30 aryl groups or C3-C30 heteroaryl groups in Ar ₁,Ar₂ are phenyl groups, biphenyl groups, naphthyl groups, phenanthryl groups, triphenylene groups, fluorenyl groups, spirofluorenyl groups, spirofluorenyloxy and anthracenyl groups, carbazolyl groups, dibenzothienyl groups, dibenzofuranyl groups, benzofluorenyl groups, benzocarbazolyl groups, benzonaphthothienyl groups, benzonaphthofuranyl groups, pyridyl groups, pyrazinyl groups, pyrimidinyl groups, quinolinyl groups, isoquinolinyl groups, quinazolinyl groups, and quinoxalinyl groups, wherein the substituents in the formula are the same or different and are independently selected from hydrogen, fluorine, chlorine, bromine groups, cyano groups, nitro groups, trifluoromethyl groups, methoxy groups, ethoxy groups, methylthio groups, ethylthio groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, tertiary butyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, phenylbutyl groups, phenyltriazinyl groups, pyrrolyl groups, C1-C6 alkyl groups, quinoxazinyl groups, quinolyl groups, and the like groups.

Preferably, the structure of formula 9 is

In the formula 9, R ₁～R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra and Rb are independently selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl or heterocycloalkyl groups, C6-C30 aryl groups and C3-C30 heteroaryl groups; m is 0-2, p is 0-3, X ₁,X₂ is independently selected from CR ₇R₈、NR₉、O、S,R₇-R₉, C1-C30 alkyl, C3-C30 cycloalkyl and C2-C30 heterocycloalkyl, and R ₇-R₈ can be connected into an alicyclic ring through any bond; R ₇、R₈ is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, rc is independently selected from hydrogen atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl or heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, rc can be fused into a ring by any bond, q is selected from 0-3, all hydrogen atoms in the formula 9 can be substituted by deuterium atom, C1-C6 alkyl, C3-C6 cycloalkyl or heterocycloalkyl, wherein substituents in the formula are the same or different and are independently selected from hydrogen atom, halogen atom, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, phenylmethyl and tert-butyl.

Further preferably, the red phosphorescent host material has a structure of

In the formula 9-1, R ₁～R₆ is independently selected from a hydrogen atom and methyl, n is 1 or 2, ra is selected from a hydrogen atom or phenyl, m is 1,2 or 3;X ₁、X₂ is independently selected from CR ₉R₁₀、NR₁₁、O、S,R₉-R₁₁, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, R ₉-R₁₀ can be connected into an aliphatic ring through any bond, R ₇、R₈ is independently selected from an aryl group of C6-C30 which is not substituted or is not substituted, C3-C30 heteroaryl, the aryl group of C6-C30 in R ₇、R₈ or C3-C30 heteroaryl is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl oxa-anthracenyl, carbazolyl, dibenzofluorenyl, benzocarbazolyl, benzonaphtalenyl, benzonaphtalenofuranyl, pyridinyl, pyrazinyl, pyrimidinyl, isoquinolinyl, quinazolinyl, C3-C30 heteroaryl, and m is selected from phenyl, biphenacyl, C10 Rc is selected from phenyl, biphenyl, phenanthryl, C3-C10, C10 Rc is synthesized through any bond, and C10 is selected from C3-C30 heteroaryl, and C10 is selected from C10. All hydrogen atoms in formula 9-1 may be substituted with deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups.

Preferably, the specific structure of the red phosphorescent light-emitting main body material is shown as RH 1-RH 24.

Preferably, the blue fluorescent light emitting layer material has a structure represented by any one of formulas 10, 11, and 12.

Preferably, the structure of formula 10 is

In the formula 10, R ₁～R₆ is independently selected from a hydrogen atom, a substituted or unsubstituted C ₁ -C4 alkyl group, n is 1 or 2;R ₇～R₁₄ is a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl or heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; ra is selected from hydrogen atoms, C1-C30 alkyl, C3-C30 cycloalkyl or heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, m is 0-3, L is selected from single bond, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene, ar is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, all hydrogen atoms in formula 10 can be substituted by deuterium atoms, C1-C6 alkyl, C3-C6 cycloalkyl or heterocycloalkyl, wherein substituents are the same or different and are independently selected from hydrogen atoms, halogen atoms, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, C6-C20 aryl, C3-C20 heteroaryl, methylbenzyl and tert-butylphenyl.

Further preferably, in formula 10, each R ₁～R₆ is independently selected from a hydrogen atom, a methyl group; ra is selected from a hydrogen atom or phenyl; m is 1,2 or 3;R ₇～R₁₄ is a hydrogen atom; L is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C20 heteroarylene group, preferably, the C6-C20 arylene group and the C3-C20 heteroarylene group in L are phenylene, biphenylene, terphenyl, naphthylene, fluorenylene, carbazolylene, dibenzothienyl, dibenzofuranylene, ar is selected from a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group, preferably, the C6-C30 aryl group or the C3-C30 heteroaryl group in Ar is phenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl, dibenzothiophenyl, benzonaphtalenyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, pyrrolyl, and the like, and the methyl, the three-or the substituents of which are all of which are independently selected from the formulae, and are phenyl, the groups, the substituents of which are selected from the following, and are phenyl, methyl, naphthyl, pyrrolyl, benzoimidazolyl, benzofluorenyl, benzoyl, benzofluorenyl, benzopyrrolyl, and pyrrolyl, and methyl, and are all substituted, and are substituted, and are substituted and are selected from substituted, and are substituted and are selected from substituted and are substituted C.

Preferably, the structure of formula 11 is

In the formula 11, R ₁～R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra represents hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, m is 0-2, L is selected from single bonds, substituted or unsubstituted C6-C30 arylene groups or C3-C30 heteroarylene groups, ar is independently selected from substituted or unsubstituted C6-C30 aryl groups or C3-C30 heteroaryl groups, all hydrogen atoms in the formula 11 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups, wherein substituents are the same or different and are independently selected from hydrogen atoms, halogen atoms, cyano groups, nitro groups, trifluoromethyl groups, methoxy groups, ethoxy groups, methylthio groups, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, C3-C20 heteroaryl groups, phenyl groups and tert-phenyl groups.

Further preferably, in formula 11, R ₁～R₆ is each independently selected from a hydrogen atom, a methyl group, n is 1 or 2, ra is selected from a hydrogen atom or a phenyl group; m is 1,2 or 3;X is selected from CR ₁₅R₁₆、NR₁₇、O、S,R₁₅-R₁₇ and is selected from hydrogen atom, C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 heterocycloalkyl, and R ₁₅-R₁₆ can be connected into an alicyclic ring through any bond; R ₇～R₁₄ is a hydrogen atom; L is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C20 heteroarylene group, preferably, the C6-C20 arylene group and the C3-C20 heteroarylene group in L are phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, carbazolylene, dibenzothienyl, dibenzofuranyl, ar is each independently selected from a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group, preferably, the C6-C30 aryl group or the C3-C30 heteroaryl group in Ar is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothienyl, dibenzofuranyl, pyrimidyl, pyrazinyl, quinolyl, pyrrolyl, and the like, and the same or the substituents of which are selected from the formulae, and the substituents of which may be independently selected from the group consisting of the following, and the formulae, and the group consisting of, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, all hydrogen atoms in formula 11 may be replaced by deuterium atoms, C1-C6 alkyl groups.

Preferably, the structure of formula 12 is

R ₁～R₆ is independently selected from hydrogen atom, substituted or unsubstituted C1-C4 alkyl, n is 1 or 2;R ₇～R₁₄ is independently selected from hydrogen atom, C1-C30 alkyl, C3-C30 cycloalkyl or heterocycloalkyl, C6-C30 aryl or C3-C30 heteroaryl, X is selected from a non-CR ₁₅R₁₆、NR₁₇、O、S,R₁₅-R₁₇ hydrogen atom, C1-C30 alkyl, C3-C30 cycloalkyl or C2-C30 heterocycloalkyl, R ₁₅-R₁₆ can be connected to form an aliphatic ring through any bond, L is selected from a single bond, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene, ar is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl, all hydrogen atoms in formula 12 can be replaced by deuterium atom, C1-C6 alkyl, C3-C6 cycloalkyl or heterocycloalkyl, R ₁₅-R₁₆ can be connected to form an aliphatic ring through any bond, L is selected from a single bond, substituted or unsubstituted C3-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene, ar is independently selected from substituted or unsubstituted C6-C30 heteroaryl, all hydrogen atoms in formula 12 can be replaced by deuterium atom, C1-C6 alkyl, C3-C6 cycloalkyl or C6 heterocycloalkyl, phenyl, halogen, phenyl, C20-C20 nitro, cyano, nitro, phenyl or nitro.

Further preferably, in formula 12, R ₁～R₆ is independently selected from a hydrogen atom, a methyl group, n is 1 or 2, X is selected from none, CR ₁₅R₁₆、NR₁₇、O、S,R₁₅-R₁₇ is selected from a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 heterocycloalkyl group, R ₁₅-R₁₆ may be linked to form an alicyclic ring by any bond; R ₇～R₁₄ is a hydrogen atom; L is selected from a single bond, a substituted or unsubstituted C6-C20 arylene group or a substituted or unsubstituted C3-C20 heteroarylene group; preferably, the C6-C20 arylene and C3-C20 heteroarylene in L are phenylene, biphenylene, terphenylene, naphthylene, fluorenylene, carbazolylene, dibenzothienyl, benzonaphthothienyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, wherein the substituents in Ar are the same or different and are independently selected from phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl, dibenzoxarenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and the substituents in Ar are selected from the group consisting of phenyl, biphenyl, naphthyl, phenanthrenyl, fluorenyl, benzofluorenyl, benzonaphtalenyl, benzothienyl, benzofuranyl, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, and the substituents in Ar are the same or different and are independently selected from the group consisting of hydrogen, chloro, bromo, pyridinyl, cyclohexyl, a the L-containing the L-a the L-aryl-a the L-be a preferably a L-a preferably a C-aryl, a L-a L-a-C- -, quinoxalinyl, wherein all hydrogen atoms in formula 12 can be replaced by deuterium atoms and C1-C6 alkyl groups.

Preferably, the specific structure of the blue fluorescent light-emitting main body material is shown as BH 1-BH 12.

Preferably, the red phosphorescent guest material specifically has a structure shown in formula 13.

In the formula 13, R ₁～R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra represents hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups and C3-C30 heteroaryl groups; m is selected from 0 to 2, R ₇～R₁₀ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C30 heteroaryl groups; R ₇～R₁₀ may be optionally condensed to form a ring, R ₁₁、R₁₂ is each independently selected from a halogen atom, a hydrogen atom, a cyano group, a substituted or unsubstituted C1-C30 haloalkyl group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group or a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, all hydrogen atoms in formula 13 may be substituted by deuterium atoms, a C1-C6 alkyl group, a C3-C6 cycloalkyl group or a heterocycloalkyl group, wherein the substituents are the same or different and are independently selected from a hydrogen atom, a halogen atom, a cyano group, a nitro group, a trifluoromethyl group, a methoxy group, an ethoxy group, a methylthio group, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C2-C6 heterocycloalkyl group, a C6-C20 aryl group, a C3-C20 heteroaryl group, a methylphenyl group, a tert-butylbenzene group.

Further preferably, the red phosphorescent guest material has the structure of

In the formula 13-1, p=2, q=1, R ₁～R₆ is independently selected from a hydrogen atom, a methyl group, n is 1 or 2;R ₇～R₁₀ is independently selected from a hydrogen atom, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C3-C20 heteroaryl group; preferably, the C6-C30 aryl or C3-C30 heteroaryl in R ₇～R₁₀ is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirofluorenyl, carbazolyl, dibenzothienyl, dibenzofuranyl, benzofluorenyl, benzocarbazolyl, benzonaphthothienyl, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl; R ₁₁、R₁₂ is independently selected from halogen atom, hydrogen atom, cyano group, substituted or unsubstituted C1-C30 haloalkyl group, substituted or unsubstituted C1-C30 alkyl group substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C2-C10 heterocycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C30 heteroaryl group, wherein the substituents are the same or different and are independently selected from hydrogen, fluorine, chlorine, bromine, cyano group, nitro group, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, cyclohexyl, phenyl, tert-butylphenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, and quinolinyl, isoquinolinyl and quinoxalinyl, wherein all hydrogen atoms in the formula 13-1 can be replaced by deuterium atoms and C1-C6 alkyl groups.

Preferably, the specific structure of the red phosphorescent guest material is shown as RD 1-RD 6;

Preferably, in the formula 1, R ₁、R₂、R₃、R₄ is methyl when n=2, and R ₁、R₂、R₃、R₄、R₅、R₆ is methyl when n=1.

In the invention, a naphtho alicyclic structure is taken as a mother nucleus, and the introduction of alkyl improves the electron supply capacity of molecules, thereby improving the hole migration capacity, stabilizing electrons and further improving the stability of molecules. Meanwhile, due to the introduction of alkyl, intermolecular accumulation is not too tight, the sublimation temperature of the material is reduced, and the energy consumption of the evaporation process is reduced. The inventor discovers that naphthalene has a larger conjugation plane, and can form better conjugation effect when being connected with other groups, thereby improving the stability of molecules. However, in practical application, it is found that the flatness of naphthalene causes stronger pi-pi acting force between molecules, which can lead to higher sublimation temperature of the material and generate problems of easy crystallization, etc., and the inventor creatively replaces the naphthalene structure with the group of formula 1 to be a mother nucleus, which can reduce the intermolecular effect, thereby making the amorphous film difficult to crystallize and further improving the performance of a plurality of functional layers of the element.

In a second aspect, the present invention provides an OLED light-emitting device comprising an OLED light-emitting organic material, said OLED light-emitting device comprising at least an anode, a cathode, and an organic layer.

Preferably, the anode is a first electrode, and the cathode is a second electrode.

Preferably, the organic layer includes an electron transport layer, a hole blocking layer, a light emitting layer, a second hole transport layer, a first hole transport layer, and a hole injection layer.

Preferably, the preparation material of at least one layer of the hole transport layer, the light emitting layer and the electron transport layer contains OLED light emitting organic materials, and the OLED light emitting device structure is shown in figure 1.

Advantageous effects

1. In the invention, a naphtho alicyclic structure is taken as a mother nucleus, and the introduction of alkyl improves the electron supply capacity of molecules, thereby improving the hole migration capacity, stabilizing electrons and further improving the stability of molecules.

2. The introduction of the alkyl and naphthalene in the invention form an aliphatic ring, so that the accumulation among molecules is not too tight, the sublimation temperature of the material is reduced, the energy consumption of the evaporation process is reduced, and the high-temperature pyrolysis of organic molecules is improved.

3. The compound provided by the invention is applied to an organic electroluminescent device, so that the device has higher efficiency, and molecules have high stability, and the luminous efficiency and the service life of the device can be further improved.

4. The compound provided by the invention has very high hole transmission capability and electron transmission capability, reduces voltage, improves efficiency, and further prolongs service life.

5. The preparation material of at least one layer of the hole transmission layer, the light-emitting layer and the electron transmission layer contains OLED light-emitting organic materials, and the specific structure is adopted for combination, so that the light-emitting efficiency and the service life of the device are improved.

Drawings

Fig. 1 is a structural diagram of an OLED light emitting device, wherein 1 is a cover layer, 2 is a second electrode, 3 is an electron transport layer, 4 is a hole blocking layer, 5 is a light emitting layer (which may be phosphorescent or fluorescent), 6 is a second hole transport layer, 7 is a first hole transport layer, 8 is a hole injection layer, 9 is a first electrode, and 10 is a substrate.

Detailed Description

The synthesis method of the hole transport material and the red phosphorescence luminescent main material adopts Buchwald-Hartwig coupling reaction, and the reaction formula is as follows:

The reaction process comprises the steps of adding 1 molar equivalent of halogen-containing compound (halogen atoms are fluorine, chlorine, bromine and iodine) and 1 molar equivalent of amino compound into a three-neck flask, adding 0.01 molar equivalent of tris (dibenzylideneacetone) dipalladium (Pd ₂(dba)₃, 0.02 molar equivalent of tri-tert-butylphosphine (t-Bu ₃ P), 2 molar equivalent of sodium tert-butoxide (NaOBu-t), adding 10 times of toluene by weight of chlorine-containing compound, replacing by systematic nitrogen, heating the reaction liquid to reflux, stirring and reacting for 180min, cooling the reaction liquid to 70 ℃, overheating a silica gel column while the reaction liquid is hot, concentrating the mother liquid to one third of the volume, adding one sixth of ethanol in the reaction liquid, stirring for 1h at room temperature, filtering, purifying by using a recrystallization and silica gel chromatographic column to obtain solid, drying the purified solid, and performing vacuum sublimation purification.

The electron transport material and the blue fluorescent luminescent main material are obtained by adopting a Suzuki coupling reaction, and the reaction formula is as follows:

The reaction process comprises mixing 1 molar equivalent of halogen-containing compound (halogen atoms are fluorine, chlorine, bromine and iodine), 1 molar equivalent of boric acid-containing compound, 0.1 molar equivalent of tetraphenylpalladium (Pd (PPh ₃)₄) and 2 molar equivalents of potassium carbonate (K ₂CO₃), adding 10 times of toluene, 1.5 times of ethanol and 1.5 times of deionized water, displacing 3 times of nitrogen, heating the reaction mixture to reflux, continuing stirring and reacting for 3 hours, cooling the reaction mixture to 50 ℃, standing and layering, washing an upper organic phase with 1.5 times of deionized water, purifying by using a standard-moment chromatographic column, recrystallizing and purifying to obtain solid, and drying and then sublimating and purifying by vacuum.

The red phosphorescent guest material has the following reaction formula:

the specific synthesis method comprises the steps of dissolving 4 molar equivalents of RDA and 1 molar equivalent of iridium trichloride hydrate into 10 times of ethylene glycol diethyl ether and 1 time of RDA of water, reacting liquid nitrogen gas for protection, heating and refluxing, and stirring for 24 hours. The reaction solution was cooled to room temperature, water was added dropwise in an amount of 10 times the weight of RDA to precipitate a large amount of solids, and the filtrate was filtered, concentrated and dried to a red solid, which was RDB.

1 Molar equivalent of compound RDB and 6 molar equivalents of diketone are dissolved in ethylene glycol diethyl ether 10 times the weight of RDB, 6 molar equivalents of sodium carbonate are added and nitrogen is purged. Stirred at 60 ℃ for 24 hours. The reaction liquid is subjected to silica gel column chromatography purification and recrystallization purification to obtain red solid RD. And drying the solid compound, and performing vacuum sublimation purification.

All the starting materials in the examples can be prepared conventionally.

Synthesis example 1

HT2 is prepared by adding 1 molar equivalent of 6-bromo-1, 2,3, 4-tetrahydro-1, 4-tetramethylanthracene and 1 molar equivalent of N- (9, 9' -spirofluorene-7-yl) -5a,9 a-dihydrodibenzo [ b, d ] furan-3-amine, 0.01 molar equivalent of tris (dibenzylideneacetone) dipalladium (Pd ₂(dba)₃, 0.02 molar equivalent of tri-tert-butylphosphine (t-Bu ₃ P), 2 molar equivalent of sodium tert-butoxide (NaOBu-t), adding 10 times the weight of bromine-containing compound into a three-necked flask, displacing with nitrogen, heating the reaction solution to reflux, stirring for 180min, cooling the reaction solution to 70 ℃, overheating the silica gel column while hot, concentrating to one third of the volume, adding one sixth of the reaction solution, stirring for 1h at room temperature, filtering, recrystallizing and purifying the mother solution by silica gel column to obtain solid, and obtaining the solid by using the mother solution and purifying the mother solution by silica gel column 72％.¹H NMR(400MHz,Chloroform-d)δ7.99(d,1H),7.84(d,4H),7.64(d,1H),7.61–7.52(m,2H),7.52–7.43(m,3H),7.42–7.16(m,10H),7.16–7.11(m,1H),7.04(d,1H),6.87(d,2H),6.83–6.76(m,1H),6.65(d,1H),1.75(s,4H),1.30(s,12H).

Synthesis example 2

HT11 was prepared by adding 1 molar equivalent of 2-bromo-7,7,10,10-tetramethyl-13, 13-diphenyl-8,9,10,13-tetrahydro-7H-indeno [1,2-b ] anthracene and 1 molar equivalent of N- [1,1' -biphenyl-4-yl ] -9, 9-dimethyl-9H-fluoren-2-amine, 0.01 molar equivalent of tris (dibenzylideneacetone) dipalladium (Pd ₂(dba)₃, 0.02 molar equivalent of tri-tert-butylphosphine (t-Bu ₃ P), 2 molar equivalents of sodium t-butoxide (NaOBu-t), further adding 10 times the weight of bromine-containing compound in a three-necked flask, displacing the system with nitrogen, heating the reaction solution to reflux, stirring to react for 180min, cooling the reaction solution to 70 ℃, thermally superheating the silica gel column, concentrating the mother solution to one sixth of the volume, adding ethanol to one third of the reaction solution, stirring at room temperature, filtering, recrystallizing and purifying and drying the silica gel column to obtain a solid, and drying the solid 75％.¹H NMR(400MHz,Chloroform-d)δ7.86(d,1H),7.83–7.77(m,1H),7.72(d,1H),7.69–7.50(m,10H),7.49–7.44(m,1H),7.44–7.33(m,6H),7.32–7.16(m,14H),7.14–7.06(m,4H),6.95(d,1H),1.75(s,4H),1.58(s,6H),1.30(s,12H).

Synthesis example 3

HT28 is prepared by adding 1 molar equivalent of 2' -chloro-1, 4-tetramethyl-1, 2,3, 4-tetrahydrospiro [1,2-a ] anthracene-8, 9' -xanthene ] and 1 molar equivalent of N- [1,1' -biphenyl-4-yl ] -9, 9-dimethyl-9H-fluorene-2-amine, 0.01 molar equivalent of tris (dibenzylideneacetone) dipalladium (Pd ₂(dba)₃, 0.02 molar equivalent of tri-tert-butylphosphine (t-Bu ₃ P), 2 molar equivalents of sodium tert-butoxide (NaOBu-t), adding 10 times of toluene by weight of chlorine-containing compound, displacing the system with nitrogen, heating the reaction solution to reflux, stirring the reaction solution for 180min, cooling the reaction solution to 70 ℃, concentrating the hot overheated silica gel column to one third of the volume, adding one sixth of ethanol of the reaction solution, stirring the reaction solution for 1H at room temperature, filtering, recrystallizing and purifying the silica gel column, and drying the silica gel column to obtain solid 70％.¹H NMR(400MHz,Chloroform-d)δ7.87(d,1H),7.72(d,1H),7.66–7.56(m,4H),7.56–7.50(m,3H),7.50–7.44(m,2H),7.43(d,6H),7.28–7.14(m,7H),7.11–7.04(m,3H),7.00(d,2H),6.97–6.90(m,2H),1.74(s,4H),1.58(d,6H),1.30(d,12H).

Synthesis example 4

E1 is prepared by mixing 1 molar equivalent of 6-bromo-1, 2,3, 4-tetrahydro-1, 4-tetramethylanthracene, 1 molar equivalent of 4, 6-bis (4- (naphthalenyl-2-yl) phenyl) -1,3, 5-triazine-2-boronic acid, 0.1 molar equivalent of tetrakis triphenylphosphine palladium (Pd (PPh ₃)₄) and 2 molar equivalents of potassium carbonate (K ₂CO₃), adding 10 times the weight of bromine-containing compound in toluene, 1.5 times the weight of bromine-containing compound in ethanol and 1.5 times the weight of bromine-containing compound in deionized water, displacing 3 times with nitrogen, heating the reaction mixture to reflux, continuing to stir the reaction mixture for 3 hours, cooling the reaction mixture to 50 ℃ for standing delamination, washing the upper organic phase with 1.5 times the weight of bromine-containing compound in deionized water, subjecting the organic phase to column chromatography purification and recrystallization purification, and drying to obtain a solid in yield 75％.¹H NMR(400MHz,Chloroform-d)δ8.86(t,1H),8.21(d,1H),8.03–7.84(m,5H),7.84–7.75(m,6H),7.71–7.59(m,10H),7.57–7.43(m,7H),1.75(s,4H),1.30(s,12H).

Synthesis example 5

E9 was prepared by mixing 1 molar equivalent of 2-chloro-7,7,10,13,13-hexamethyl-8,9,10,13-tetrahydro-7H-indeno [1,2-b ] anthracene, 1 molar equivalent of (4- (5 a,9 a-dihydrodibenzofuran-3-yl) -6-phenylpyrimidine-2-boric acid, 0.1 molar equivalent of tetrakis triphenylphosphine palladium (Pd (PPh ₃)₄) and 2 molar equivalents of potassium carbonate (K ₂CO₃), adding 10 times the weight of chlorine-containing compound in toluene, 1.5 times the weight of chlorine-containing compound in ethanol and 1.5 times the weight of chlorine-containing compound in deionized water, displacing 3 times with nitrogen, heating the reaction mixture to reflux, continuing to stir the reaction mixture for 3 hours, cooling the reaction mixture to 50 ℃, standing for delamination, washing the upper organic phase with 1.5 times the weight of chlorine-containing compound in deionized water, subjecting the organic phase to column purification and recrystallization purification, and drying to obtain a solid 70％.¹H NMR(400MHz,Chloroform-d)δ8.51(d,1H),8.24–8.18(m,3H),8.16(s,1H),8.00(d,1H),7.91(t,3H),7.86(d,1H),7.76(d,1H),7.67–7.51(m,3H),7.51–7.32(m,6H),1.75(s,4H),1.58(s,6H),1.30(s,12H).20

Synthesis example 6

E14 is prepared by mixing 1 molar equivalent of 2-chloro-7,7,10,10-tetramethyl-7, 8,9, 10-tetrahydrospiro [1,2-b ] anthracene-13, 9 '-xanthene ],1 molar equivalent of (4- ([ 1,1' -biphenyl ] -4-yl) -6-phenyl-1, 3, 5-triazin-2-yl) boric acid, 0.1 molar equivalent of tetraphenylpalladium (Pd (PPh ₃)₄) and 2 molar equivalents of potassium carbonate (K ₂CO₃) in a reaction flask, adding 10 times the weight of chlorine-containing compounds of toluene, 1.5 times the weight of ethanol and 1.5 times the weight of chlorine-containing compounds of deionized water, displacing 3 times with nitrogen, heating the system to reflux, continuing stirring the reaction mixture for 3 hours, cooling the reaction mixture to 50 ℃, standing for layering, washing the upper organic phase with 1.5 times the weight of chlorine-containing compounds of deionized water, purifying the organic phase by a conventional column chromatography, recrystallizing, drying to obtain a solid, purifying the organic phase, and drying to obtain a solid 74％.¹H NMR(400MHz,Chloroform-d)δ8.62–8.49(m,2H),7.96–7.85(m,2H),7.82(d,1H),7.78–7.70(m,3H),7.68–7.61(m,3H),7.61–7.54(m,4H),7.52–7.30(m,6H),7.26(m,2H),7.14(d,2H),7.06(m,2H),6.99(m,2H),1.75(s,4H),1.30(s,12H).

Synthesis example 7

The RH2 is prepared by adding 1 molar equivalent of 4-chlorobiphenyl and 1 molar equivalent of 8,8,11,11-tetramethyl-2- (9-phenyl-9, 9 a-dihydro-4 aH-carbazole-6-yl) -5,8,9,10,11,13 b-hexahydro-4 aH-naphtho [2,3-b ] carbazole, 0.01 molar equivalent of tris (dibenzylideneacetone) dipalladium (Pd ₂(dba)₃, 0.02 molar equivalent of tri-tert-butylphosphine (t-Bu ₃ P), 2 molar equivalents of sodium tert-butoxide (NaOBu-t) into a three-necked flask, adding 10 times of toluene by weight of chlorine-containing compounds, replacing the system with nitrogen, heating the reaction liquid to reflux, stirring and reacting for 180min, cooling the reaction liquid to 70 ℃, heating a silica gel column, concentrating the mother liquid to one third of the volume, adding ethanol of the volume of the reaction liquid, stirring for 1h at room temperature, filtering, re-crystallizing and purifying by using the silica gel column, and obtaining a solid with ,¹H NMR(400MHz,Chloroform-d)δ9.12(d,1H),8.14(d,1H),8.09–8.03(m,1H),7.80(m,1H),7.72–7.56(m,10H),7.55–7.42(m,8H),7.42–7.13(m,7H),1.75(s,4H),1.30(s,12H)., wherein the solid is obtained.

Synthesis example 8

The RH7 is prepared by adding 1 molar equivalent of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and 1 molar equivalent of 8,8,11,11-tetramethyl-5, 8,9,10,11,13 b-hexahydro-4 aH-naphtho [2,3-b ] carbazole, 0.01 molar equivalent of tris (dibenzylideneacetone) dipalladium (Pd ₂(dba)₃, 0.02 molar equivalent of tri-tert-butylphosphine (t-Bu ₃ P), 2 molar equivalent of sodium tert-butoxide (NaOBu-t), adding 10 times of toluene by weight of chlorine-containing compound, replacing by nitrogen, heating the reaction solution to reflux, stirring and reacting for 180min, reducing the reaction solution to 70 ℃, superheating a silica gel column while hot, concentrating to one third of the volume, adding ethanol of one sixth of the reaction solution, stirring for 1h at room temperature, filtering ,¹H NMR(400MHz,Chloroform-d)δ8.65–8.50(m,2H),8.27–8.16(m,1H),7.95–7.86(m,2H),7.70–7.54(m,7H),7.54–7.23(m,10H),1.75(d,4H),1.30(s,12H)., and drying to obtain a solid with the yield of 73%.

Synthesis example 9

RH18 is prepared by adding 1 molar equivalent of 4-chlorobiphenyl and 1 molar equivalent of 10,10,13,13-tetramethyl-5-phenyl-4 a,5,6a,7,10,11,12,13,15b,16b decahydroindolo [2,3-b ] naphtho [2,3-h ] carbazole, 0.01 molar equivalent of tris (dibenzylideneacetone) dipalladium (Pd ₂(dba)₃, 0.02 molar equivalent of tri-tert-butylphosphine (t-Bu ₃ P), 2 molar equivalent of sodium tert-butoxide (NaOBu-t), adding 10 times the weight of chlorine-containing compound into a three-necked flask, displacing the mixture with nitrogen, heating the mixture to reflux, stirring the mixture to react for 180min, cooling the mixture to 70 ℃, superheating the silica gel column while the mixture is hot, concentrating the mixture to one third of the volume, adding one sixth of ethanol into the mixture, stirring the mixture at room temperature for 1h, filtering, recrystallizing and drying the mixture to obtain a solid, purifying the solid, and drying the solid 75％.¹H NMR(400MHz,Chloroform-d)δ8.90(d,1H),8.15–8.02(m,1H),7.71–7.49(m,11H),7.49–7.30(m,9H),7.30–7.24(m,2H),1.75(d,4H),1.30(s,12H)..

Synthesis example 10

BH2 was prepared by mixing 1 molar equivalent of 6-bromo-1, 2,3, 4-tetrahydro-1, 4-tetramethylanthracene, 1 molar equivalent of 1,2,3,4,5,6,7, 8-octadeuterium-10- (dibenzo [ b, d ] furan-2-yl) anthracene-9-yl) boronic acid, 0.1 molar equivalent of tetraphenylpalladium (Pd (PPh ₃)₄) and 2 molar equivalents of potassium carbonate (K ₂CO₃), adding 10 times the weight of bromine-containing compound in toluene, 1.5 times the weight of bromine-containing compound in ethanol and 1.5 times the weight of bromine-containing compound in deionized water, displacing the system with nitrogen 3 times, heating the reaction mixture to reflux, and continuing the stirring reaction for 3 hours. Cooling the reaction mixture to 50 ℃, standing for layering, washing an upper organic phase with deionized water with the weight 1.5 times of the weight of the bromine-containing compound, purifying the organic phase by a standard chromatographic column, recrystallizing and purifying, and drying to obtain a solid with the yield 81％.¹H NMR(400MHz,Chloroform-d)δ8.03(m,1H),7.97–7.92(m,1H),7.84(m,1H),7.66–7.56(m,3H),7.57–7.43(m,4H),7.38(m,1H),7.28(d,1H),1.75(d,4H),1.30(s,12H).

Synthesis example 11

BH9 is prepared by mixing 1 molar equivalent of 3-chloro-8,8,11,11-tetramethyl-4 a,8,9,10,13 b-hexahydroanthracene [2,3-b ] benzofuran, 1 molar equivalent of 1,2,3,4,5,6,7, 8-octadeuterium-10- (dibenzo [ b, d ] furan-2-yl) anthracene-9-yl) boronic acid, 0.1 molar equivalent of tetraphenylpalladium (Pd (PPh ₃)₄) and 2 molar equivalents of potassium carbonate (K ₂CO₃), adding 10 times the weight of chlorine-containing compounds of toluene, 1.5 times the weight of ethanol and 1.5 times the weight of chlorine-containing compounds of deionized water, displacing the system with nitrogen for 3 times, heating the reaction mixture to reflux, and continuing stirring for reaction for 3 hours. Cooling the reaction mixture to 50 ℃, standing for layering, washing an upper organic phase with deionized water with the weight 1.5 times of that of the chlorine-containing compound, purifying the organic phase by a standard chromatographic column, recrystallizing and purifying, and drying to obtain solid with the yield 76％.¹H NMR(400MHz,Chloroform-d)δ8.01(d,1H),7.98–7.95(m,1H),7.85–7.72(m,4H),7.68–7.58(m,2H),7.58–7.30(m,6H),1.74(s,4H),1.30(s,12H).

Synthesis example 12

The preparation method of RD2 comprises the following steps:

4 molar equivalents of RD2-1 and 1 molar equivalent of iridium trichloride hydrate are dissolved in 10 times of ethylene glycol diethyl ether with the weight of RD2-1 and 1 time of water with the weight of RD2-1, and the mixture is heated and refluxed after being protected by liquid nitrogen gas and stirred for 24 hours. The reaction solution was cooled to room temperature, water 10 times the weight of RD2-1 was added dropwise to precipitate a large amount of solids, and the mixture was filtered to give a filtrate having a concentration of red solid, RD2-2, in a yield of 70%.

1 Molar equivalent of compound RD2-2 and 6 molar equivalents of diketone are dissolved in 10 times the weight of RD2-2 glycol diethyl ether, 6 molar equivalents of sodium carbonate are added and nitrogen is purged. Stirred at 60 ℃ for 24 hours. Purifying the reaction liquid by silica gel column chromatography and recrystallization, and drying to obtain red solid RD2, yield 50％.¹H NMR(400MHz,Chloroform-d)δ7.86(d,2H),7.79–7.67(m,4H),7.52(d,2H),7.27(d,4H),7.03–6.74(m,2H),5.65(d,1H),2.55(s,8H),2.42(d,10H),1.74(p,8H),1.73–1.38(m,22H),1.36–1.29(m,24H).

Synthesis example 13

The preparation method of RD4 comprises the following steps:

4 molar equivalents of RD4-1 and 1 molar equivalent of iridium trichloride hydrate are dissolved in 10 times of ethylene glycol diethyl ether with the weight of RD4-1 and 1 time of water with the weight of RD4-1, and the mixture is heated and refluxed after being protected by liquid nitrogen gas and stirred for 24 hours. The reaction solution was cooled to room temperature, water 10 times the weight of RD4-1 was added dropwise to precipitate a large amount of solid, filtered, and the filtrate was concentrated and dried to a red solid, RD4-2, in 75% yield.

1 Molar equivalent of compound RD4-2 and 6 molar equivalents of diketone are dissolved in 10 times the weight of RD4-2 glycol diethyl ether, 6 molar equivalents of sodium carbonate are added and nitrogen is purged. Stirred at 60 ℃ for 24 hours. Purifying the reaction liquid by silica gel column chromatography and recrystallization, and drying to obtain red solid RD4, yield 42％.¹H NMR(400MHz,Chloroform-d)δ8.11(s,2H),8.07(s,2H),8.00(d,2H),7.91(d,2H),7.65(d,2H),7.57–7.49(m,6H),6.96(d,2H),5.89(p,1H),2.47(s,6H),2.41(s,6H),2.36(s,6H),2.08(d,6H),1.87(s,8H),1.30(d,24H).

Comparative examples 1 to 13 respectively provided HT-ref1、HT-ref2、HT-ref3、E-ref1、E-ref2、E-ref3、RH-ref1、RH-ref2、RH-ref3、BH-Ref1、BH-Ref2、RD-Ref1、RD-Ref2 compounds, the structures of which are shown below;

Example 14

The embodiment provides a method for preparing a blue fluorescent device, comprising forming a transparent anode ITO film layer with a film thickness of 150nm on a glass substrate 1 to obtain a first electrode 2 as anode, and evaporatingThe mixed material with the hole transport material HT2 is used as a hole injection layer 3, the mixing ratio is 3:97 (mass ratio), then 100nm thick compound HT2 is evaporated to obtain a first layer hole transport layer 4, and then 20nm thick compound is evaporatedObtaining a second hole transport layer 5, and then evaporating a compound BH2 material and the compound BH2 material at an evaporation rate of 95:530Nm, a blue light emitting unit (fluorescent light emitting layer 6) was fabricated, and then 10nm was vapor depositedForming a hole blocking layer 7, and then evaporating the compound E1 andAn electron transport layer 8 having a thickness of 30nm was formed at a mixing ratio of 4:6 (mass ratio), and then ytterbium having a thickness of 3nm and magnesium silver having a thickness of 10nm (mass ratio of 1:9) were sequentially formed as a second electrode 9, followed by vapor deposition of a 70nm cap material thereonA cover layer 10 is formed.

Comparative example 14

The embodiment of comparative example 14 is the same as in example 14 except that HT2 in the hole injection layer 3 and the first hole transport layer 4 is replaced with HT2 after the seal was heated for 240 hours in the thermal stability test, E1 of the compound in the electron transport layer 8 is replaced with E1 after the seal was heated for 240 hours in the thermal stability test, and BH2 of the compound in the blue light emitting unit (light emitting layer 6) is replaced with BH2 after the seal was heated for 240 hours in the thermal stability test.

Comparative example 15

The embodiment of comparative example 15 is the same as in example 14 except that HT-ref1 is used instead of HT2 in the hole injection layer 3 and the first hole transport layer 4, E-ref1 is used instead of E1 of the compound in the electron transport layer 8, and BH-ref1 is used instead of BH2 of the compound in the blue light emitting cell (light emitting layer 6).

Comparative example 16

The embodiment of comparative example 16 is the same as in example 14 except that HT-ref1 after 240 hours of seal heating in the thermal stability test is used for the hole injection layer 3 and the first hole transport layer 4 instead of HT-ref1 in comparative example 2, E-ref1 after 240 hours of seal heating in the thermal stability test is used for the electron transport layer 8 instead of E-ref1 in comparative example 2, and BH-ref1 after 240 hours of seal heating in the thermal stability test is used for the blue light emitting unit (fluorescent light emitting layer 6) instead of BH-ref1 in comparative example 2.

Example 15

The embodiment provides a method for preparing a red phosphor device, comprising forming a transparent anode ITO film layer with a film thickness of 150nm on a glass substrate 1 to obtain a first electrode 102 as anode, and evaporatingWith hole-transporting materialsAs the hole injection layer 3, the mixture ratio was 3:97 (mass ratio), followed by evaporation of 100nm thickA first hole transport layer 4 was obtained, and then a 100nm thick compound was evaporatedObtaining a second hole transport layer 5, evaporating 40nm compound RH2 and compound RD2 at an evaporation rate of 95:5 to obtain a red light emitting unit 6, and evaporating 10nmForming a hole blocking layer 7, and then evaporatingAnd (3) withAn electron transport layer 8 having a thickness of 30nm was formed at a mixing ratio of 4:6 (mass ratio), and then magnesium silver having a thickness of 100nm (mass ratio of 1:9) was formed as the second electrode 9.

Comparative example 17

The embodiment of comparative example 17 is the same as in example 15, except that the compound RH2 and the compound RD2 in the red light emitting unit 6 are replaced with RH2 and RD2, respectively, after the sealing was heated for 240 hours in the thermal stability test.

Comparative example 18

The embodiment of comparative example 18 is the same as in example 15, except that the compound RH2 and the compound RD2 in the red light emitting unit 6 are replaced with RH-ref1, RD-ref1, respectively.

Comparative example 19

The embodiment of comparative example 19 is the same as in example 15 except that RH-ref1, RD-ref1 in the red light emitting unit 6 is replaced with RH-ref1, RD-ref1 after the seal has been heated for 240 hours in the thermal stability test, respectively.

Performance testing

1. Evaporating temperature comparison:

The compounds of examples 1 to 13 were tested for evaporation temperatures with the corresponding naphthalene molecule-containing compounds of comparative examples 1 to 13. The experimental method comprises the steps of adding 5g of material into a vacuum cavity of a boron nitride crucible with a heating source and 50 cubic centimeters, vacuumizing to a vacuum degree of 5 x 10 < -8 > torr, and monitoring the temperature when the evaporation speed is 10A/hour.

The compounds of examples 1 to 13 have lower material evaporation temperatures than the corresponding naphthalene molecule-containing compounds of comparative examples 1 to 13. The results are shown in Table 1.

2. Thermal stability test:

The compounds of examples 1,4, 7, 10, 12 and the compounds of comparative examples 1,4, 7, 10, 12 were subjected to a thermal stability test by preparing a quartz tube having a diameter of 10mm and a length of 150mm and one end of which was sealed and one end was unsealed, then adding a material to be tested from the unsealed end, evacuating the quartz tube to 1 x 10-6torr, and heating the unsealed end to heat seal. Heating the sealed quartz tube in a heating furnace at a heating temperature of The heating time was 240 hours, with the temperature at/hour plus 40 ℃. The purity was measured by liquid chromatography, and the experimental results are shown in Table 2.

3. The device tests in example 14 and comparative examples 14 to 16 were performed using keithley power supply and a combination test apparatus of MS-75 spectrometer. The voltage was 10mA/cm ², the efficiency was expressed as the current efficiency at 10mA/cm ² divided by the color coordinate CIEy value (in Cd/A/CIEy), and the lifetime was the time required for the luminance to decay to 95% of the initial luminance at 10mA/cm ² current. The results of comparative example 14, which were obtained with device example 14 as 100%, were shown in Table 3, with a voltage of 4.0V, an efficiency of 141Cd/A/CIEy, and a 95% lifetime of 650 hours.

The device tests in example 15 and comparative examples 17 to 19 were performed using keithley power supply and a combination test apparatus of MS-75 spectrometer. The voltage was 10mA/cm ², the efficiency was expressed as the current efficiency at 10mA/cm ² divided by the color coordinate CIEy value (in Cd/A/CIEy), and the lifetime was the time required for the luminance to decay to 95% of the initial luminance at 10mA/cm ² current. The results of comparative example are shown in Table 4, with 100% results for device example 15, example 15 having a voltage of 3.7V, an efficiency of 173Cd/A/CIEy, and a 95% lifetime of 3200 hours.

TABLE 1

TABLE 2

TABLE 3 Table 3

	Voltage (V)	Efficiency of	Life span
				Example 14	100%	100%	100%
Comparative example 14	100%	98%	98%
				Comparative example 15	105%	97%	90%
Comparative example 16	110%	90%	70%

TABLE 4 Table 4

	Voltage (V)	Efficiency of	Life span
				Example 15	100%	100%	100%
Comparative example 17	100%	97%	95%
				Comparative example 18	102%	95%	89%
Comparative example 19	104%	91%	80%

Claims

1. The OLED luminescent organic material is characterized by comprising a hole transport layer material, a luminescent layer material and an electron transport layer material, wherein the luminescent layer material comprises a fluorescent luminescent layer material or a phosphorescent luminescent layer material;

(I) When the light-emitting layer material is a phosphorescent light-emitting layer material, the phosphorescent light-emitting layer material comprises a phosphorescent light-emitting host material and a phosphorescent light-emitting guest material, wherein the phosphorescent light-emitting host material is a red phosphorescent light-emitting host material;

Wherein the red phosphorescent light-emitting main material has a structure shown in any one of the formulas 8-1 and 9-1;

The structure of the formula 8-1 is

8-1

In the formula 8-1, R ₁、R₂、R₃、R₄ is methyl, R ₅、R₆ is hydrogen, rb is hydrogen, n is 2, p is 1, ar ₁ is biphenyl or triazinyl, ar ₂ is hydrogen or carbazolyl;

the structure of the formula 9-1 is

9-1

In the formula 9-1, R ₁、R₂、R₃、R₄ is methyl, R ₅、R₆ is hydrogen, ra and Rc are both hydrogen, N is 2, m and q are both 1, X ₁、X₂ is N, R ₇ is biphenyl, and R ₈ is phenyl;

The phosphorescent guest material is a red phosphorescent guest material having a structure shown in formula 13;

13 of the group

In the formula 13, R1, R2, R3 and R4 are methyl, R5 and R6 are hydrogen, ra is hydrogen, n is 2, m and q are 1, p is 2, R7 and R8 are fused to form a ring, R9 is methyl, R10 is hydrogen, and R11 and R12 are methyl or cyclohexyl;

(II) when the luminescent layer material is a fluorescent luminescent layer material, the fluorescent luminescent layer material comprises a blue fluorescent luminescent host material having a structure represented by any one of formulas 10, 11;

The structure of the said 10 is

10. The method of the invention

In the formula 10, R ₁、R₂、R₃、R₄ is methyl, R ₅、R₆ is hydrogen, ra is hydrogen, n is 2, m is 1, L is a single bond, R ₇-R₁₄ are deuterium, ar is dibenzofuranyl;

The structure of the said 11 is

11. The method of the invention

In the formula 11, R ₁、R₂、R₃、R₄ is methyl, R ₅、R₆ is hydrogen, ra is hydrogen, n is 2, m is 1, X is O, L is a single bond, R ₇-R₁₄ is deuterium, ar is dibenzofuranyl;

All hydrogen atoms in the above formulas 8-1, 9-1, 10, 11, 13 may be replaced with deuterium atoms.

2. The OLED light-emitting organic material according to claim 1, wherein the hole transport layer material has a structure represented by any one of formula 2, formula 3, and formula 4;

The structure of the formula 2 is

2, 2

In the formula 2, R ₁~R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra is selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl or heterocycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, m is 0-3, L ₁、L₂、L₃ is selected from single bonds, substituted or unsubstituted C6-C30 arylene groups or C3-C30 heteroarylene groups, ar ₁,Ar₂ is independently selected from substituted or unsubstituted C6-C30 aryl groups or C3-C30 heteroaryl groups, and all hydrogen atoms in the formula 2 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups;

The structure of the 3 is

3

In the formula 3, R ₁~R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra and Rb are independently selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups and C3-C30 heteroaryl groups, X is selected from CR ₇R₈、NR₉、O、S,R₇-R₉ and is selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups and C2-C30 heterocycloalkyl groups, R ₇-R₈ can be connected into an aliphatic ring through any bond, m is 0-2, p is 0-3, L is selected from single bond, substituted or unsubstituted C6-C30 arylene groups or C3-C30 heteroarylene groups, ar ₁,Ar₂ is independently selected from substituted or unsubstituted C6-C30 aryl groups or C3-C30 heteroaryl groups, and all hydrogen atoms in the formula 3 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocyclic groups;

The structure of the said 4 is

4. The method is to

In the formula 4, R ₁~R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra represents hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, m is selected from 0 to 2, R ₇~R₁₈ is selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, and R is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C30 heteroaryl group, and a substituted or unsubstituted C30-C30 heteroaryl group,At least one of R ₇~R₁₈ isWherein L is selected from single bond, substituted or unsubstituted C6-C30 arylene or C3-C30 heteroarylene, ar ₁,Ar₂ is independently selected from substituted or unsubstituted C6-C30 aryl or C3-C30 heteroaryl, and all hydrogen atoms in the formula 4 can be substituted by deuterium atoms, C1-C6 alkyl, C3-C6 cycloalkyl or heterocycloalkyl.

3. The OLED light-emitting organic material according to claim 1, wherein the electron transport layer material has a structure represented by any one of formula 5, formula 6, and formula 7;

The structure of the said 5 is

5. The method is to

In the formula 5, R ₁~R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra represents hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, m is selected from 0 to 2, L is selected from single bonds, substituted or unsubstituted C6-C30 arylene groups or C3-C30 heteroarylene groups, and all hydrogen atoms in the formula 5 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups;

the electron transport layer comprises a formula 6;

6. The method is to

In the formula 6, R ₁~R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra and Rb are independently selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups and C3-C30 heteroaryl groups, X is selected from CR ₇R₈、NR₉、O、S,R₇-R₉ and is selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups and C2-C30 heterocycloalkyl groups, R ₇-R₈ can be connected into an aliphatic ring through any bond, m is 0-2, p is 0-3, L is selected from single bond, substituted or unsubstituted C6-C30 arylene groups or C3-C30 heteroarylene groups, and all hydrogen atoms in the formula 6 can be substituted by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups;

The structure of the 7 is

7. The method of the invention

In the formula 7, R ₁~R₆ is independently selected from hydrogen atoms, substituted or unsubstituted C1-C4 alkyl groups, n is 1 or 2, ra represents hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups or heterocycloalkyl groups, C6-C30 aryl groups, C3-C30 heteroaryl groups, X is selected from CR ₇R₈、NR₉、O、S,R₇-R₉, is selected from hydrogen atoms, C1-C30 alkyl groups, C3-C30 cycloalkyl groups and C2-C30 heterocycloalkyl groups, R ₇-R₈ and can be connected with an optional bond to form an aliphatic ring, and m is selected from 0-2, R ₇~R₁₈ is selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, and R ₇~R₁₈ is selected from hydrogen atoms, substituted or unsubstituted C3-C30 heteroaryl groups,At least one of R ₇~R₁₈ isL is selected from single bond, substituted or unsubstituted C6-C30 arylene or C3-C30 heteroarylene; all hydrogen atoms in the formula 7 can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups; electron acceptor in the formulas 5, 6 and 7 are each independently selected from naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, fluoranthryl, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, imidazolyl, pyrazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxanyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, naphthyridinyl, and the like pyrazinopyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoloquinazolinyl, benzimidazolophenidinyl, spiro [ fluorene-9, 9' -xanthene ], benzonaphthyl, dinaphthofuranyl, naphthofuranyl, dinaphthiophene, naphthabenzothienyl, triphenylphosphine oxide, triphenylborane, 1-10 o-phenanthroline, cyano-substituted aryl or heteroaryl, fluoro-substituted aryl or heteroaryl, trifluoromethyl substituted aryl or heteroaryl.

4. An OLED light-emitting device comprising the OLED light-emitting organic material according to any one of claims 1-3, wherein the OLED light-emitting device comprises at least an anode, a cathode, an organic layer.