OLED light-emitting organic material and OLED light-emitting device thereof

Abstract

The invention relates to the technical field of organic light-emitting diodes, in particular to IPC C07, and more particularly relates to an OLED light-emitting organic material and an OLED light-emitting device thereof. The OLED light-emitting organic material provided by the invention comprises a naphthoalicyclic ring structure, and the electron donating ability of molecules is improved, so that the electron transfer ability is improved, holes are stabilized, and the stability of the molecules is further improved. When the compound is applied to the organic electroluminescent device, the device can have high efficiency, molecules have high stability, the luminous efficiency of the device can be further improved, and the service life of the device can be further prolonged.

Description

An OLED luminescent organic material and its OLED luminescent device Technical Field

[0001] 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. This application is a divisional application of patent application 2023106726904, filed on June 7, 2023, entitled "An OLED Light-Emitting Organic Material and an OLED Light-Emitting Device Thereof". Background Technology

[0002] Organic light-emitting diodes (OLEDs) have the characteristics of low energy consumption, thinness, wide viewing angle, fast response, and active light emission. They have been widely used in weaponry, electrical appliances, and harsh environments, especially as planar light sources or lighting sources in the field of electrical displays.

[0003] With the continuous development of organic light-emitting diodes (OLEDs) and the expansion of their application fields, the requirements for the performance of OLEDs in various aspects are becoming increasingly stringent. Naphthalene, as a commonly used material component in OLED devices, is widely used in hole transport materials, light-emitting layer materials, and electron transport layer materials. Naphthalene has a large conjugated plane, which allows it to form a good conjugation effect when linked with other groups, resulting in excellent molecular stability.

[0004] Chinese invention patent application (application number CN201911129807.4) discloses a nitrogen-containing seven-membered ring carbazole organic light-emitting material and its application. The organic light-emitting material's structure is based on a nitrogen-containing seven-membered ring carbazole, and its general structural formula is shown in Formula I. In Formula I, R is benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, pyrene, binaphthalene, bianthracene, fluoranthene, benzo[a]anthracene, fluorene, benzo[a]fluorene, N-phenylcarbazole, N-naphthylcarbazole, N-phenylbenzo[a]carbazole, dibenzofuran, or dibenzothiophene. When the nitrogen-containing seven-membered ring carbazole organic light-emitting materials are used in the fabrication of OLED devices as the main light-emitting material or electron transport material, the external quantum efficiency, power efficiency, and current efficiency of OLED devices are greatly improved, which also significantly extends the service life of OLED devices and has good market prospects. However, the planarity of naphthalene causes strong π-π interactions between molecules, which leads to problems such as high sublimation temperature and easy crystallization. Its evaporation temperature and film stability still need to be improved. Summary of the Invention

[0005] To address the problems in the prior art, the first aspect of the present invention provides an OLED light-emitting organic material, comprising the structure shown in Formula 1.

[0006]

[0007] In Formula 1, R1~R6 represent hydrogen atoms, substituted or unsubstituted C1~C30 alkyl groups, substituted or unsubstituted C3~C30 cycloalkyl groups, heterocycloalkyl groups, substituted or unsubstituted C6~C30 aryl groups, and substituted or unsubstituted C3~C30 heteroaryl groups; Y is independently 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, and C3~C30 heteroaryl groups; the 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, and C3~C30 heteroaryl groups may also be replaced by 0 atoms. The substituents in group A may be replaced by any number of substituents selected from substituent group C; the substituents in group A are 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, and C3-C30 heteroaryl groups; the substituents in group A may also be replaced by 0 or any number of substituents selected from substituent group B; the substituents in group B are 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, and C3-C30 heteroaryl groups; the substituents in group B may also be replaced by 0 or any number of substituents selected from substituent group C. The substituents in substituent group C are 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, and C3-C30 heteroaryl groups; the substituents in substituent group C may also be replaced by 0 or any number of substituents selected from substituent group D; the substituents in substituent group D are selected from hydrogen atoms, metal atoms, amino groups, hydroxyl groups, mercapto groups, C1-C30 alkyl groups, C2-C30 heterocycloalkyl groups, C6-C30 aryl groups, and C3-C30 heteroaryl groups. 3~C30 cycloalkyl, C2~C30 heterocycloalkyl, C6~C30 aryl, C3~C30 heteroaryl; m is 1~4; Y and any one or more of the substituents in substituent groups A, B, C, and D can be linked by any bond to form an aliphatic ring, heterocyclic ring, aromatic ring, or heteroaromatic ring; all hydrogen atoms in Formula 1 can be replaced by deuterium atoms or C1~C12 alkyl, C3~C12 cycloalkyl, C2~C12 heterocycloalkyl, and C6~C12 aryl.

[0008] In one embodiment, the OLED light-emitting organic material includes a hole transport layer material, a light-emitting layer material, and an electron transport layer material.

[0009] In one embodiment, the luminescent layer material includes a fluorescent luminescent layer material or a phosphorescent luminescent layer material; the fluorescent luminescent layer material includes a blue fluorescent luminescent host material; the phosphorescent luminescent layer material includes a phosphorescent host material and a phosphorescent guest material; the phosphorescent host material is a red phosphorescent host material; and the phosphorescent guest material is a red phosphorescent guest material.

[0010] In one embodiment, the hole transport layer material has a structure shown in any one of Formula 2, Formula 3, or Formula 4.

[0011] In one embodiment, the structure of Formula 2 is as follows:

[0012] In Formula 2, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra is selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; m is 0 to 3; L1, L2, and L3 are selected from single bonds, substituted or unsubstituted C6 to C30 arylene groups, or substituted or unsubstituted C3 to C30 heteroarylene groups; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted C6 to C30 aryl groups or substituted or unsubstituted C3 to C30 heteroaryl groups.

[0013] In Formula 2, all hydrogen atoms can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, or heterocycloalkyl groups.

[0014] The substituted groups may be 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.

[0015] In one embodiment, the hole transport layer material has the following structure:

[0016] In Formula 2-1, R1 to R7 are each independently selected from hydrogen atoms and methyl groups; L1, L2, and L3 are selected from single bonds, substituted or unsubstituted C6-C20 arylene groups, or substituted or unsubstituted C3-C20 heteroarylene groups; in one embodiment, the C6-C20 arylene groups and C3-C20 heteroarylene groups in L1, L2, and L3 are phenylene, diphenylene, terphenylene, naphthylene, fluorene, carbazolyl, dibenzothiophene, or dibenzofuranyl; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aromatic groups. The aryl group or substituted or unsubstituted C3-C30 heteroaryl group in Ar1 and Ar2 is phenyl, diphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazolyl, dibenzothiophene, dibenzofuranyl, benzofluorenyl, benzocarbazolyl, benzonaphthothiophene, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, or quinoxalinyl.

[0017] Wherein, the substituted groups may be 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, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, and quinoxalinyl.

[0018] In Formula 2-1, all hydrogen atoms can be replaced by deuterium atoms or C1-C6 alkyl groups.

[0019] In one embodiment, the structure of Formula 3 is as follows:

[0020] In Formula 3, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra and Rb are each independently selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; X is selected from CR7R8, NR9, O, and S; R7-R9 are selected from hydrogen atoms, C1 to C30 alkyl groups. C3~C30 cycloalkyl, C2~C30 heterocycloalkyl, R7-R8 can be connected by any bond to form an aliphatic ring; m is 0~2; p is 0~3; L is selected from single bond, substituted or unsubstituted C6~C30 arylene or substituted or unsubstituted C3~C30 heteroarylene; Ar1, Ar2 are each independently selected from substituted or unsubstituted C6~C30 aryl or substituted or unsubstituted C3~C30 heteroaryl.

[0021] In Formula 3, all hydrogen atoms can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, or heterocycloalkyl groups.

[0022] The substituted groups may be 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.

[0023] In one embodiment, the hole transport layer material has the following structure:

[0024] In Formula 3-1, R1 to R6 are each independently selected from hydrogen atoms and methyl groups, and n is 1 or 2; X is selected from CR7R8, NR9, O, and S; R7 to R9 are selected from hydrogen atoms, C1 to C6 alkyl groups, C3 to C6 cycloalkyl groups, and C2 to C6 heterocycloalkyl groups; R7 to R8 can be connected by any bond to form an aliphatic ring; L is selected from single bonds, substituted or unsubstituted C6 to C20 arylene groups, or substituted or unsubstituted C3 to C20 heteroarylene groups; in one embodiment, the C6 to C20 arylene groups and C3 to C20 heteroarylene groups in L are phenylene, diphenylene, terphenylene, naphthylene, fluorene, or carboxylidene. Azolyl, dibenzothiophene, dibenzofuranyl; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl groups; in one embodiment, the C6-C30 aryl or C3-C30 heteroaryl group in Ar1 and Ar2 is phenyl, diphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, dibenzofuranyl, benzo[fluorenyl], benzo[carbazole], benzo[naphthothiophene], benzo[naphthofuranyl], pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl.

[0025] Wherein, the substituted groups may be 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, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, and quinoxalinyl.

[0026] In Formula 3-1, all hydrogen atoms can be replaced by deuterium atoms or C1-C6 alkyl groups.

[0027] In one embodiment, the structure of Formula 4 is as follows:

[0028] Formula 4: R1~R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1~C4 alkyl groups, and n is 1 or 2; Ra represents 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 none, CR 19 R 20 NR 21 O, S, R 19 -R 21 Selected from hydrogen atoms, C1~C30 alkyl groups, C3~C30 cycloalkyl groups, C2~C30 heterocycloalkyl groups, R 19 -R 20 They can be connected by any bond to form a fatty ring; m is selected from 0 to 2; R7 to R 18 Selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, R7~R 18 At least one of them is L is selected from single-bonded, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl.

[0029] In Formula 4, all hydrogen atoms can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, or heterocycloalkyl groups.

[0030] The substituted groups may be 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.

[0031] In one embodiment, the hole transport layer material has the following structure:

[0032] In Formula 4-1: R1 to R6 are each independently selected from hydrogen atoms or methyl groups, and n is 1 or 2; X is selected from none or X is selected from CR. 19 R 20 NR 21 O, S, R 19 -R 21 Selected from hydrogen atoms, C1~C6 alkyl, C3~C6 cycloalkyl, C2~C6 heterocycloalkyl, R19 -R 20 They can be connected by any bond to form a fatty ring; R7~R 18 Selected from hydrogen atoms, substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted C3-C6 cycloalkyl or heterocycloalkyl groups, substituted or unsubstituted C6-C12 aryl groups, substituted or unsubstituted C3-C12 heteroaryl groups, R7~R 18 At least one of them is L is selected from single-bonded, substituted or unsubstituted C6-C20 arylene groups or substituted or unsubstituted C3-C20 heteroarylene groups; in one embodiment, the C6-C20 arylene groups and C3-C20 heteroarylene groups in L are phenylene, diphenylene, terphenylene, naphthylene, fluorene, carbazolyl, dibenzothiophene, or dibenzofuranyl; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted groups. Substituted C3-C30 heteroaryl groups; in one embodiment, the C6-C30 aryl or C3-C30 heteroaryl groups in Ar1 and Ar2 are phenyl, diphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, dibenzofuranyl, benzofluorenyl, benzocarbazole, benzonaphthothiophene, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl.

[0033] Wherein, the substituted groups may be 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, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, and quinoxalinyl.

[0034] In Formula 4-1, all hydrogen atoms can be replaced by deuterium atoms or C1-C6 alkyl groups.

[0035] In one embodiment, the hole transport material has the structure shown in HT1 to HT36:

[0036]

[0037]

[0038]

[0039]

[0040]

[0041] In one embodiment, the electron transport layer material has a structure shown in any one of Formulas 5, 6, and 7.

[0042] In one embodiment, the structure of Formula 5 is as follows:

[0043] In Formula 5, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra represents hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; m is selected from 0 to 2; L is selected from single bonds, substituted or unsubstituted C6 to C30 arylene groups, or substituted or unsubstituted C3 to C30 heteroarylene groups.

[0044] In Formula 5, all hydrogen atoms can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, or heterocycloalkyl groups; the substituted groups may be 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.

[0045] In one embodiment, the structure of the electron transport layer material is as follows:

[0046] In Formula 5-1, R1 to R7 are each independently selected from hydrogen atoms and methyl groups; Ra is selected from hydrogen atoms and phenyl groups; m is 1, 2, or 3; L is selected from single bonds, substituted or unsubstituted C6-C20 arylene groups, or substituted or unsubstituted C3-C20 heteroarylene groups; in one embodiment, the C6-C20 arylene groups and C3-C20 heteroarylene groups in L are phenylene, diphenylene, terphenylene, naphthylene, fluorene, carbazolyl, dibenzothiophene, or dibenzofuranyl; X1, X2, and X3 are each independently C or N, and at least one of them is N; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C30 heteroarylene groups; the C6-C30 aryl groups or C3-C30 heteroarylene groups in Ar1 and Ar2 are... The substituted groups are phenyl, diphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, dibenzofuranyl, benzofluorenyl, benzocarbazole, benzonaphthothiophene, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl; wherein the substituted groups are the same or different and are independently selected from hydrogen, fluorine, chlorine, bromine, and cyanide. The following are listed: methyl, nitro, 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, isoquinolinyl, quinoxalinyl; all hydrogen atoms in Formula 5-1 may be replaced by deuterium atoms or C1-C6 alkyl groups.

[0047] In one embodiment, the structure of Formula 6 is as follows:

[0048] In Formula 6, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra and Rb are each independently selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; X is selected from CR7R8, NR9, O, and S; R7 to R9 are selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl groups, and C2 to C30 heterocycloalkyl groups; R7 to R8 can be connected by any bond to form an aliphatic ring; m is 0 to 2; p is 0 to 3; L is selected from single bonds, substituted or unsubstituted C6 to C30 arylene groups, or substituted or unsubstituted C3 to C30 heteroarylene groups.

[0049] In Formula 6, all hydrogen atoms can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, or heterocycloalkyl groups.

[0050] The substituted groups may be 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.

[0051] In one embodiment, the structure of the electron transport layer material is as follows:

[0052] In Formula 6-1, R1 to R7 are each independently selected from hydrogen atoms and methyl groups; Ra is selected from hydrogen atoms and phenyl groups; m is selected from 0 to 2; in one embodiment, it is 0, 1, or 2; X is selected from CR7R8, NR9, O, or S; R7 to R9 are selected from hydrogen atoms, C1 to C6 alkyl groups, C3 to C6 cycloalkyl groups, or C2 to C6 heterocycloalkyl groups; R7 to R8 can be connected by any bond to form an aliphatic ring; L is selected from single bonds, substituted or unsubstituted C6 atoms. ~C20 arylene or substituted or unsubstituted C3~C20 heteroarylene; in one embodiment, the C6~C20 arylene and C3~C20 heteroarylene in L are phenylene, diphenylene, terphenylene, naphthylene, fluorene, carbazolyl, dibenzothiophene, or dibenzofuranyl; X1, X2, and X3 are each independently C or N, and at least one of them is N; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted groups. The aryl group of C6-C30 or the substituted or unsubstituted heteroaryl group of C3-C30; wherein the aryl group of C6-C30 or the heteroaryl group of C3-C30 in Ar1 and Ar2 is phenyl, diphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, dibenzofuranyl, benzofluorenyl, benzocarbazole, benzonaphthothiophene, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, Isoquinolinyl, quinazolinyl, quinoxalinyl; wherein the substituted groups 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, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl.

[0053] In Formula 6-1, all hydrogen atoms can be replaced by deuterium atoms or C1-C6 alkyl groups.

[0054] In one embodiment, the structure of Formula 7 is as follows:

[0055] In Formula 7, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra represents hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; X is selected from none, CR 19 R 20 NR 21 O, S, R 19 -R 21 Selected from hydrogen atoms, C1~C30 alkyl groups, C3~C30 cycloalkyl groups, C2~C30 heterocycloalkyl groups, R 19 -R 20 They can be connected by any bond to form a fatty ring; m is selected from 0 to 2; R7 to R 18 Selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, R7~R 18 At least one of them is L is selected from single bonds, substituted or unsubstituted C6-C30 arylene or C3-C30 heteroarylene; all hydrogen atoms in Formula 7 may be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups; the substituted groups may be 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, tert-butylphenyl.

[0056] In one embodiment, Electron in Equations 5, 6, and 7 Each acceptor is independently selected from naphthyl, anthracene, phenanthryl, pyrenyl, peryl, fluorenyl, fluoranyl, pyridyl, pyrroleyl, pyrimidinyl, pyridazinyl, imidazolyl, pyrazolyl, azole, isozolyl, thiazolyl, isothiazolyl, triazolyl, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, pyrazinyl, azinyl, thiazolyl, dioxazinyl, dioxazinyl, triazinyl, tetraazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, acridineyl, xanthyl, phenanthridineyl, diazanaphthyl, triazaindenyl, indoleyl, dihydroindoleyl, nitro-indenyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzoxoxane Azolyl, benzimidazolyl, benzothiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, carbazoyl, benzocarbazoyl, dibenzocarbazoyl, indolocarbazoyl, indocarbazoyl, phenazinyl, imidazopyridyl, phenazinyl, phenanthridine, phenanthridine, phenanthridine, phenthiazinyl, imidazopyridyl, imidazophenanthridine, benzimidazolylquinazolinyl, benzimidazolylphenanthridine, spiro[fluorene-9,9'-oxazanthene], phenylbinaphthyl, dinaphthofuranyl, naphthobenzofuranyl, dinaphthiophene, naphthobenzothiophene, triphenylphosphine oxide, triphenylborane, 1-10 o-phenanthrolinel, cyano-substituted aryl or heteroaryl, fluorine-substituted aryl or heteroaryl, trifluoromethyl-substituted aryl or heteroaryl.

[0057] In one embodiment, the structure of the electron transport layer material is as follows:

[0058] Formula 7-1, R1~R6 are each independently selected from hydrogen atoms or methyl groups, and n is 1 or 2; Ra is selected from hydrogen atoms or phenyl groups; X is selected from none, CR 19 R 20 NR 21 O, S, R 19 -R 20 Selected from hydrogen atoms, C1~C6 alkyl, C3~C6 cycloalkyl, C2~C6 heterocycloalkyl, R 19 -R 20 They can be connected by any bond to form a fatty ring; R7~R 18 Selected from hydrogen atoms, substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted C3-C6 cycloalkyl or heterocycloalkyl groups, substituted or unsubstituted C6-C12 aryl groups, substituted or unsubstituted C3-C12 heteroaryl groups, R7~R 18 At least one of them is L is selected from single-bonded, substituted or unsubstituted C6-C20 arylene groups or substituted or unsubstituted C3-C20 heteroarylene groups; in one embodiment, the C6-C20 arylene groups and C3-C20 heteroarylene groups in L are phenylene, diphenylene, terphenylene, naphthylene, fluorene, carbazolyl, dibenzothiophene, or dibenzofuranyl; X1, X2, and X3 are each independently C or N, and at least one of them is N; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted groups. The substituted C6-C30 aryl group or the substituted or unsubstituted C3-C30 heteroaryl group; the C6-C30 aryl group or C3-C30 heteroaryl group in Ar1 and Ar2 is phenyl, diphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazolyl, dibenzothiophene, dibenzofuranyl, benzofluorenyl, benzocarbazolyl, benzonaphthothiophene, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl.

[0059] Wherein, the substituted groups may be 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, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, and quinoxalinyl.

[0060] In Formula 7-1, all hydrogen atoms can be replaced by deuterium atoms or C1-C6 alkyl groups.

[0061] In one embodiment, the specific structure of the electron transport layer material is shown in E1~E24.

[0062]

[0063]

[0064]

[0065]

[0066] In one embodiment, the red phosphorescent luminescent host material has a structure shown in any one of Formula 8 or Formula 9.

[0067] In one embodiment, the structure of Formula 8 is as follows:

[0068] In Formula 8, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra and Rb are each independently selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; Rb can be connected by any bond to form an aliphatic ring, heterocyclic ring, aromatic ring, or heteroaromatic ring; m is 0 to 2; p is 0 to 3; Ar1 ​​and Ar2 are each independently selected from hydrogen atoms, substituted or unsubstituted C6 to C30 aryl groups, or substituted or unsubstituted C3 to C30 heteroaryl groups; all hydrogen atoms in Formula 8 can be substituted by deuterium atoms, C1 to C6 alkyl groups, C3 to C6 cycloalkyl or heterocycloalkyl groups.

[0069] The substituted groups may be 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.

[0070] In one embodiment, the structure of the red phosphorescent luminescent host material is as follows:

[0071] In Formula 8-1, R1 to R6 are each independently selected from hydrogen atoms and methyl groups, and n is 1 or 2; Rb are each independently selected from hydrogen atoms, C1 to C6 alkyl groups, C3 to C6 cycloalkyl or heterocycloalkyl groups, C6 to C20 aryl groups, and C3 to C20 heteroaryl groups; Rb can be connected by any bond to form aliphatic rings, heterocycles, aromatic rings, or heteroaromatic rings; p is 0 to 3, and in one embodiment, it is 0, 1, 2, or 3; Ar1 ​​and Ar2 are each independently selected from hydrogen atoms, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C3-C30 heteroaryl groups; the C6-C30 aryl or C3-C30 heteroaryl groups in Ar1 and Ar2 are phenyl, diphenyl, naphthyl, phenanthrene, phenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, dibenzofuranyl, benzofluorenyl, benzocarbazole, or benzonaphthothiophene. The groups substituted with benzo[a]naphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, or quinoxalinyl are selected independently 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, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, or quinoxalinyl.

[0072] In Formula 8-1, all hydrogen atoms can be replaced by deuterium atoms or C1-C6 alkyl groups.

[0073] In one embodiment, the structure of Formula 9 is as follows:

[0074] In Formula 9, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra and Rb are each independently selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; m is 0 to 2; p is 0 to 3; X1 and X2 are each independently selected from CR7R8, NR9, O, and S; R7 to R9 are selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl groups, and C2 to C30 heterocycloalkyl groups; R7 to R8 can be connected by any bond to form an aliphatic ring. R7 and R8 are each independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl groups; Rc groups are each independently selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl groups; Rc groups can be fused together to form a ring by any bond; q Selected from 0 to 3; all hydrogen atoms in Formula 9 may be replaced by deuterium atoms, C1 to C6 alkyl groups, C3 to C6 cycloalkyl groups, or heterocycloalkyl groups; the substituted groups may be the same or different, and are independently selected from hydrogen atoms, halogen atoms, cyano, nitro, trifluoromethyl, methoxy, ethoxy, methylthio, C1 to C6 alkyl, C3 to C6 cycloalkyl, C2 to C6 heterocycloalkyl, C6 to C20 aryl, C3 to C20 heteroaryl, tolyl, and tert-butylphenyl.

[0075] In one embodiment, the structure of the red phosphorescent luminescent host material is as follows:

[0076] In Formula 9-1, R1 to R6 are each independently selected from hydrogen atoms or methyl groups, and n is 1 or 2; Ra is selected from hydrogen atoms or phenyl groups; m is 1, 2, or 3; X1 and X2 are each independently selected from CR9R 10 NR 11 O, S, R9-R 11 Selected from hydrogen atoms, C1~C6 alkyl, C3~C6 cycloalkyl, C2~C6 heterocycloalkyl, R9-R 10The atoms can be linked by any bond to form an aliphatic ring; R7 and R8 are each independently selected from C6-C30 aryl or C3-C30 heteroaryl groups that are unsubstituted, hydrogen-atom-free, substituted, or unsubstituted; the C6-C30 aryl or C3-C30 heteroaryl groups in R7 and R8 are phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, or dibenzofuranyl. , benzo[fluorenyl], benzo[carbazoyl], benzo[naphthothioyl], benzo[naphthofuranyl], pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl; m is selected from 0 to 2; Rc represents a hydrogen atom or a C1 to C10 alkyl, C3 to C10 cycloalkyl, or C2 to C10 heterocycloalkyl, C6 to C30 aryl, or C3 to C30 heteroaryl; Rc can be fused together by any bond to form a ring; q is selected from 0 to 3.

[0077] In Formula 9-1, all hydrogen atoms can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, or heterocycloalkyl groups.

[0078] In one embodiment, the specific structure of the red phosphorescent luminescent host material is shown as RH1~RH24.

[0079]

[0080] In one embodiment, the blue fluorescent emitting layer material has a structure shown in any one of Formulas 10, 11, and 12.

[0081] In one embodiment, the structure of Formula 10 is as follows:

[0082] In Formula 10, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; R7 to R6 are selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups. 14 The atom 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, or a substituted or unsubstituted C3-C30 heteroaryl group; Ra is selected from hydrogen atom, C1-C30 alkyl group, C3-C30 cycloalkyl or heterocycloalkyl group, C6-C30 aryl group, or C3-C30 heteroaryl group; m is 0-3; L is selected from single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group; Ar is selected from substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group.

[0083] In Formula 10, all hydrogen atoms can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, or heterocycloalkyl groups.

[0084] The substituted groups may be 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.

[0085] In one embodiment, in Formula 10, R1~R6 are each independently selected from hydrogen atoms and methyl groups; Ra is selected from hydrogen atoms or phenyl groups; m is 1, 2, or 3; R7~R 14 L is a hydrogen atom; L is selected from single bonds, substituted or unsubstituted C6-C20 arylene groups, or substituted or unsubstituted C3-C20 heteroarylene groups; in one embodiment, the C6-C20 arylene groups and C3-C20 heteroarylene groups in L are phenylene, diphenylene, terphenylene, naphthylene, fluorene, carbazolyl, dibenzothiophene, or dibenzofuranyl; Ar is selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C30 heteroarylene groups.

[0086] In one embodiment, the C6-C30 aryl or C3-C30 heteroaryl group in Ar is selected from phenyl, diphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, benzofluorenyl, benzocarbazole, benzonaphthothiophene, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl.

[0087] 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, tolyl, tert-butylphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, and quinoxalinyl.

[0088] In one embodiment, the structure of formula 11 is as follows:

[0089] In Formula 11, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra represents hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; m is 0 to 2; L is selected from single bonds, substituted or unsubstituted C6 to C30 arylene groups, or C3 to C30 heteroarylene groups; Ar are each independently selected from substituted or unsubstituted C6 to C3 0 aryl or C3-C30 heteroaryl; all hydrogen atoms in Formula 11 may be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups; the substituted groups may be 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, tert-butylphenyl.

[0090] In one embodiment, in Formula 11, R1 to R6 are each independently selected from hydrogen atoms or methyl groups, and n is 1 or 2; Ra is selected from hydrogen atoms or phenyl groups; m is 1, 2, or 3; X is selected from CR 15 R 16 NR 17 O, S, R 15 -R 17 Selected from hydrogen atoms, C1~C6 alkyl, C3~C6 cycloalkyl, C2~C6 heterocycloalkyl, R 15 -R 16 They can be connected by any bond to form a fatty ring; R7~R 14 The atom is a hydrogen atom; L is selected from single-bonded, substituted or unsubstituted C6-C20 arylene groups or substituted or unsubstituted C3-C20 heteroarylene groups; in one embodiment, the C6-C20 arylene group and the C3-C20 heteroarylene group in L are phenylene, diphenylene, terphenylene, naphthylene, fluorene, carbazolyl, dibenzothiophene, or dibenzofuranyl; Ar is each independently selected from substituted or unsubstituted C6-C30 aryl groups. The aryl group of C6-C30 or the heteroaryl group of C3-C30 in Ar may be phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, benzofluorenyl, benzocarbazole, benzonaphthothiophene, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, or quinoxalinyl.

[0091] Wherein, the substituted groups may be 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, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, and quinoxalinyl.

[0092] In one embodiment, the structure of formula 12 is as follows:

[0093] In Formula 12: R1~R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1~C4 alkyl groups, and n is 1 or 2; R7~R 14 Each element is 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 none, CR 15 R 16 NR 17 O, S, R 15 -R 17 Selected from hydrogen atoms, C1~C30 alkyl groups, C3~C30 cycloalkyl groups, and C2~C30 heterocycloalkyl groups, R 15 -R 16 The atoms can be linked by any bond to form an aliphatic ring; L is selected from single bonds, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl; 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 atoms, C1-C6 alkyl, C3-C6 cycloalkyl or heterocycloalkyl.

[0094] The substituted groups may be 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.

[0095] In one embodiment, in Formula 12: R1~R6 are each independently selected from hydrogen atoms and methyl groups, and n is 1 or 2; X is selected from none, CR 15 R 16 NR 17 O, S, R 15 -R 17 Selected from hydrogen atoms, C1~C6 alkyl, C3~C6 cycloalkyl, C2~C6 heterocycloalkyl, R 15 -R 16They can be connected by any bond to form a fatty ring; R7~R 14 L is a hydrogen atom; L is selected from single bonds, substituted or unsubstituted C6-C20 arylene groups, or substituted or unsubstituted C3-C20 heteroarylene groups; in one embodiment, the C6-C20 arylene groups and C3-C20 heteroarylene groups in L are phenylene, diphenylene, terphenylene, naphthylene, fluorene, carbazolyl, dibenzothiophene, or dibenzofuranyl; Ar is selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C3-C30 heteroarylene groups.

[0096] In one embodiment, the C6-C30 aryl or C3-C30 heteroaryl group in Ar is phenyl, diphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, benzofluorenyl, benzocarbazole, benzonaphthothiophene, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, or quinoxalinyl.

[0097] Wherein, the substituted groups may be 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, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, and quinoxalinyl.

[0098] In one embodiment, the specific structure of the blue fluorescent luminescent host material is shown as BH1~BH12.

[0099]

[0100] In one embodiment, the red phosphorescent guest material specifically has the structure shown in Formula 13.

[0101]

[0102] In Formula 13, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra represents hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; m is selected from 0 to 2; R7 to R6 are also selected from R7 to R6. 10Each is independently selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C3-C30 heteroaryl groups; R7~R 10 It can fuse into rings by any bond; R 11 R 12 Each of the following is independently selected from halogen atoms, hydrogen atoms, cyano groups, substituted or unsubstituted C1-C30 haloalkyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, or substituted or unsubstituted C2-C30 heterocyclic alkyl groups; substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C3-C30 heteroaryl groups; all hydrogen atoms in Formula 13 may be substituted with deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, or heterocyclic alkyl groups.

[0103] The substituted groups may be 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.

[0104] In one embodiment, the structure of the red phosphorescent guest material is as follows:

[0105] In Equation 13-1, p=2, q=1, R1~R6 are each independently selected from hydrogen atoms and methyl groups, and n is 1 or 2; R7~R 10 Each of the R7 to R10 atoms is independently selected from hydrogen atoms, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C2-C10 heterocycloalkyl groups, substituted or unsubstituted C6-C20 aryl groups, or substituted or unsubstituted C3-C20 heteroaryl groups; in one embodiment, the R7-R10 atoms are selected from hydrogen atoms, substituted or unsubstituted C1-C10 alkyl groups, substituted or unsubstituted C3-C10 heteroaryl groups, or substituted or unsubstituted C3-C20 heteroaryl groups. 10 The C6-C30 aryl or C3-C30 heteroaryl groups are phenyl, diphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, spirofluorenyl, spirofluorenoxanthyl, carbazole, dibenzothiophene, dibenzofuranyl, benzofluorenyl, benzocarbazole, benzonaphthothiophene, benzonaphthofuranyl, pyridyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl; R 11 R 12Each is independently selected from halogen atoms, hydrogen atoms, cyano groups, substituted or unsubstituted C1-C30 haloalkyl groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C10 cycloalkyl groups, substituted or unsubstituted C2-C10 heterocycloalkyl groups; substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups.

[0106] Wherein, the substituted groups may be 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, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl; all hydrogen atoms in Formula 13-1 may be replaced by deuterium atoms or C1-C6 alkyl groups.

[0107] In one embodiment, the specific structure of the red phosphorescent guest material is shown as RD1~RD6; .

[0108] In one embodiment, in Formula 1, when n=2, R1, R2, R3, and R4 are methyl groups; when n=1, R1, R2, R3, R4, R5, and R6 are methyl groups.

[0109] In this invention, a naphthalene-aliphatic ring structure is used as the parent core. The introduction of alkyl groups enhances the electron-donating ability of the molecule, thereby improving hole migration and stabilizing electrons, thus improving molecular stability. Simultaneously, the introduction of alkyl groups prevents excessively dense molecular packing, lowering the sublimation temperature of the material and reducing the energy consumption of the vapor deposition process. The inventors have discovered that naphthalene has a large conjugated plane, which can form a good conjugation effect when connected with other groups, thereby improving molecular stability. However, in practical applications, the planarity of naphthalene has resulted in strong π-π interactions between molecules, leading to a higher sublimation temperature and problems such as easy crystallization. The inventors have creatively replaced the naphthalene structure with groups from Formula 1 as the parent core, which reduces intermolecular interactions, making the amorphous film less prone to crystallization and thus improving the performance of many functional layers of the device.

[0110] A second aspect of the present invention provides an OLED light-emitting device containing OLED light-emitting organic material, wherein the OLED light-emitting device includes at least an anode, a cathode, and an organic layer.

[0111] In one embodiment, the anode is a first electrode; and the cathode is a second electrode.

[0112] In one embodiment, 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.

[0113] In one embodiment, the material used to prepare at least one of the hole transport layer, the light-emitting layer, and the electron transport layer contains OLED light-emitting organic material; the structure of the OLED light-emitting device is shown in Figure 1.

[0114] Beneficial effects 1. In this invention, the naphthoid aliphatic ring structure is used as the parent core. The introduction of alkyl groups improves the electron-donating ability of the molecule, thereby improving the hole migration ability and stabilizing the electrons, thus improving the stability of the molecule.

[0115] 2. The introduction of alkyl groups in this invention forms an aliphatic ring with naphthalene, which prevents the molecules from packing too tightly, reduces the sublimation temperature of the material, reduces the energy consumption of the vapor deposition process, and improves the high-temperature pyrolysis of organic molecules.

[0116] 3. When the compounds of the present invention are applied to organic electroluminescent devices, the devices can have high efficiency, and the molecules have high stability, which can further improve the luminous efficiency and lifespan of the devices.

[0117] 4. The compounds in this invention provide high hole transport capability and electron transport capability, reduce voltage, improve efficiency, and thus extend service life.

[0118] 5. The hole transport layer, light-emitting layer, and electron transport layer in this invention are prepared using materials containing OLED light-emitting organic materials, and are combined in a specific structure to improve the luminous efficiency and lifespan of the device. Attached Figure Description

[0119] Figure 1 is a structural diagram of the blue fluorescent device provided in Example 14; 1 is the capping layer, 2 is the second electrode, 3 is the electron transport layer, 4 is the hole blocking layer, 5 is the light-emitting layer (which can be phosphorescent or fluorescent), 6 is the second hole transport layer, 7 is the first hole transport layer, 8 is the hole injection layer, 9 is the first electrode, and 10 is the substrate. Detailed Implementation

[0120] The synthesis method for hole transport materials and red phosphorescent host materials employs the Buchwald–Hartwig coupling reaction, as shown in the following equation:

[0121] Reaction 1

[0122] Reaction 2 Reaction 3 Reaction 4

[0123] Reaction 5 The reaction process for reaction 6 is as follows: In a three-necked flask, first add 1 molar equivalent of a halogen-containing compound (halogen atoms are fluorine, chlorine, bromine, and iodine), 1 molar equivalent of an amino compound, 0.01 molar equivalent of tris(dibenzylacetone)dipalladium (Pd2(dba)3), 0.02 molar equivalent of tri-tert-butylphosphine (t-Bu3P), and 2 molar equivalents of sodium tert-butoxide (NaOBu-t). Then add toluene at 10 times the weight of the chlorine-containing compound. The system is purged with nitrogen, and the reaction solution is heated to reflux and stirred for 180 min. The reaction solution is then cooled to 70°C and superheated through a silica gel column. The mother liquor is concentrated to one-third of its volume, and one-sixth the volume of the reaction solution of ethanol is added. The mixture is stirred at room temperature for 1 h and then filtered. The solid is then purified by recrystallization and silica gel column chromatography. The purified solid is dried and then purified by vacuum sublimation.

[0124] The electron transport material and the blue fluorescent luminescent host material were obtained using the Suzuki coupling reaction, as shown in the following reaction formula:

[0125] Reaction 7

[0126] Reaction 8 Reaction 9 Reaction 10

[0127] The reaction process for reaction formula 11 is as follows: In a reaction flask, 1 molar equivalent of a halogen-containing compound (halogen atoms are fluorine, chlorine, bromine, or iodine), 1 molar equivalent of a boric acid compound, 0.1 molar equivalent of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4), and 2 molar equivalents of potassium carbonate (K2CO3) are mixed. Toluene (10 times the weight of the chlorine-containing compound), ethanol (1.5 times the weight of the chlorine-containing compound), and deionized water (1.5 times the weight of the chlorine-containing compound) are added. The system is purged with nitrogen three times. The reaction mixture is heated to reflux and stirred for 3 hours. The reaction mixture is cooled to 50°C and allowed to stand for phase separation. The upper organic phase is washed with 1.5 times the weight of the chlorine-containing compound in deionized water. The organic phase is purified by regular column chromatography and recrystallization to obtain a solid. After drying, it is purified by vacuum sublimation.

[0128] The reaction formula for the red phosphorescent guest material is as follows:

[0129] The specific synthesis method for reaction 12 is as follows: 4 molar equivalents of RDA and 1 molar equivalent of iridium trichloride hydrate are dissolved in 10 times the weight of RDA in ethylene glycol diethyl ether and 1 times the weight of RDA in water. The reaction solution is heated to reflux under nitrogen protection and stirred for 24 hours. The reaction solution is cooled to room temperature, and 10 times the weight of RDA in water is added dropwise, resulting in the precipitation of a large amount of solid. This solid is filtered, and the filtrate is concentrated and dried to obtain a red solid, which is RDB.

[0130] One molar equivalent of compound RDB and six molar equivalents of diketone were dissolved in 10 times the weight of RDB in ethylene glycol diethyl ether. Six molar equivalents of sodium carbonate were added, and the mixture was purged with nitrogen. The mixture was stirred at 60°C for 24 hours. The reaction solution was purified by silica gel column chromatography and recrystallization to obtain a red solid, RD. The solid compound was dried and then purified by vacuum sublimation.

[0131] All the raw materials in the examples can be prepared conventionally.

[0132] The preparation method of HT2 in Synthetic Example 1 is as follows: In a three-necked flask, first add 1 molar equivalent of 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylanthracene, 1 molar equivalent of N-(9,9'-spirofluorene-7-yl)-5a,9a-dihydrodibenzo[b,d]furan-3-amine, 0.01 molar equivalent of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.02 molar equivalent of tri-tert-butylphosphine (t-Bu3P), 2 molar equivalents of sodium tert-butoxide (NaOBu-t), then add 10 times the weight of the bromine-containing compound in toluene. The system is purged with nitrogen, and the reaction solution is heated to reflux. The reaction mixture was stirred for 180 min. The reaction solution was cooled to 70 °C and then superheated through a silica gel column while still hot. The mother liquor was concentrated to one-third of its volume, and one-sixth the volume of ethanol was added. The mixture was stirred at room temperature for 1 h and then filtered. The solid was then purified by recrystallization and silica gel column chromatography, with a yield of 72%. 1 H NMR (400 MHz, Chloroform-d) δ 7.99 (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).

[0133] The preparation method of HT11 in Synthesis Example 2 is as follows: In a three-necked flask, first add 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, 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 (Pd2(dba)3), and 0.02 molar equivalents of... Equivalents of tri-tert-butylphosphine (t-Bu3P), 2 molar equivalents of sodium tert-butoxide (NaOBu-t), and 10 times the weight of the bromine-containing compound in toluene were added. The system was purged with nitrogen, and the reaction solution was heated to reflux and stirred for 180 min. The reaction solution was then cooled to 70 °C and superheated through a silica gel column. The mother liquor was concentrated to one-third of its volume, and one-sixth the volume of the reaction solution in ethanol was added. The mixture was stirred at room temperature for 1 h and then filtered. The solution was then purified by recrystallization and silica gel column chromatography, and dried to obtain a solid with a yield of 75%. 1 H NMR (400 MHz, Chloroform-d) δ 7.86 (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). The preparation method of HT28 in Example 3 is as follows: In a three-necked flask, first add 1 molar equivalent of 2'-chloro-1,1,4,4-tetramethyl-1,2,3,4-tetrahydrospiro[1,2-a]anthracene-8,9'-oxazanthracene], 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 (Pd2(dba)3), and 0.02 molar equivalent of... Add 1 / 3 mol of tri-tert-butylphosphine (t-Bu3P), 2 molar equivalents of sodium tert-butoxide (NaOBu-t), and 10 times the weight of the chlorine-containing compound in toluene. Purge the system with nitrogen, heat the reaction mixture to reflux, and stir for 180 min. Cool the reaction mixture to 70°C and superheat it using a silica gel column chromatography column. Concentrate the mother liquor to one-third of its volume, add one-sixth the volume of ethanol, stir at room temperature for 1 h, and filter. Purify by recrystallization and silica gel column chromatography, then dry to obtain a solid with a yield of 70%. 1H NMR (400 MHz, 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). The preparation method of Synthetic Example 4E1 is as follows: In a reaction flask, 1 molar equivalent of 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylanthracene, 1 molar equivalent of 4,6-bis(4-(naphthyl-2-yl)phenyl)-1,3,5-triazine-2-boronic acid, 0.1 molar equivalent of tetra(triphenylphosphine)palladium (Pd(PPh3)4), and 2 molar equivalents of potassium carbonate (K2CO3) were mixed. Toluene (10 times the weight of the bromine-containing compound), ethanol (1.5 times the weight of the bromine-containing compound), and deionized water (1.5 times the weight of the bromine-containing compound) were added. The system was purged with nitrogen three times. The reaction mixture was heated to reflux and stirred for 3 hours. The reaction mixture was cooled to 50°C and allowed to stand for phase separation. The upper organic phase was washed with 1.5 times the weight of the bromine-containing compound in deionized water. The organic phase was purified by regular column chromatography and recrystallization, and dried to obtain a solid with a yield of 75%. 1H NMR (400 MHz, Chloroform-d) δ 8.86 (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). The preparation method of Synthetic Example 5E9 is as follows: In a reaction flask, 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-(5a,9a-dihydrodibenzofuran-3-yl)-6-phenylpyrimidine-2-boronic acid, 0.1 molar equivalent of tetra(triphenylphosphine)palladium (Pd(PPh3)4), and 2 molar equivalents of potassium carbonate (K2CO3) were mixed. Toluene, 1.5 molar equivalents of chlorinated compounds, and deionized water were added. The system was purged with nitrogen three times. The reaction mixture was heated to reflux and stirred for 3 hours. The reaction mixture was cooled to 50°C, allowed to stand and separate into layers, and the upper organic phase was washed with 1.5 molar equivalents of deionized water containing chlorinated compounds. The organic phase was purified by regular column chromatography and recrystallization, and dried to obtain a solid with a yield of 70%. 1H NMR (400 MHz,Chloroform-d) δ 8.51 (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, The preparation method of Example 6E14 (12H).20) is as follows: In a reaction flask, 1 molar equivalent of 2-chloro-7,7,10,10-tetramethyl-7,8,9,10-tetrahydrospiro[1,2-b]anthracene-13,9'-oxazanthracene], 1 molar equivalent of (4-([1,1'-biphenyl]-4-yl)-6-phenyl-1,3,5-triazin-2-yl)boronic acid, 0.1 molar equivalent of tetratriphenylphosphine palladium (Pd(PPh3)4) and 2 molar equivalents of potassium carbonate (K2CO3) are mixed, and 10 times the weight of the chlorinated compound in toluene, 1.5 times the weight of the chlorinated compound in ethanol and 1.5 times the weight of the chlorinated compound in deionized water are added. The system is purged with nitrogen 3 times, the reaction mixture is heated to reflux, and the reaction is stirred for 3 hours. The reaction mixture was cooled to 50°C and allowed to stand to separate into layers. The upper organic phase was washed with 1.5 times the weight of the chlorinated compound in deionized water. The organic phase was purified by regular column chromatography and recrystallization, and dried to obtain a solid with a yield of 74%. 1H NMR (400 MHz, Chloroform-d) δ 8.62 – 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). The preparation method of RH2 in Synthesis Example 7 is as follows: In a three-necked flask, first add 1 molar equivalent of 4-chlorobiphenyl, and 1 molar equivalent of 8,8,11,11-tetramethyl-2-(9-phenyl-9,9a-dihydro-4aH-carbazole-6-yl)-5,8,9,10,11,13b-hexahydro-4aH-naphtho[2,3-b]carbazole, and 0.01 molar equivalent of tris(dibenzylacetone)dipalladium (Pd2(dba)3, 0.02 mol equivalents of tri-tert-butylphosphine (t-Bu3P), 2 mol equivalents of sodium tert-butoxide (NaOBu-t), and 10 times the weight of the chlorine-containing compound in toluene were added. The system was purged with nitrogen, and the reaction solution was heated to reflux and stirred for 180 min. The reaction solution was then cooled to 70°C and superheated on a silica gel column. The mother liquor was concentrated to one-third of its volume, and one-sixth the volume of the reaction solution in ethanol was added. The mixture was stirred at room temperature for 1 h and then filtered. Further purification was achieved by recrystallization and silica gel column chromatography. 1 ¹H NMR (400 MHz, Chloroform-d) δ 9.12 (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). Drying yielded a solid, 78% yield.

[0134] The preparation method of RH7 in Synthetic Example 8 is as follows: In a three-necked flask, first add 1 molar equivalent of 2-chloro-4,6-diphenyl-1,3,5-triazine, 1 molar equivalent of 8,8,11,11-tetramethyl-5,8,9,10,11,13b-hexahydro-4aH-naphtho[2,3-b]carbazole, 0.01 molar equivalent of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.02 molar equivalent of tritert-butylphosphine (t-Bu3P), 2 molar equivalents of sodium tert-butoxide (NaOBu-t), and then add 10 times the weight of the chlorine-containing compound in toluene. The system is purged with nitrogen, the reaction solution is heated to reflux, and the reaction is stirred for 180 min. The reaction solution is cooled to 70°C and superheated on a silica gel column while still hot. The mother liquor is concentrated to one-third of its volume, and one-sixth the volume of the reaction solution in ethanol is added. The mixture is stirred at room temperature for 1 h, filtered, and then... 1 ¹H NMR (400 MHz, Chloroform-d) δ 8.65 – 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). Drying yielded a solid, 73% yield.

[0135] The preparation method of RH18 in Synthetic Example 9 is as follows: In a three-necked flask, first add 1 molar equivalent of 4-chlorobiphenyl, and 1 molar equivalent of 10,10,13,13-tetramethyl-5-phenyl-4a,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 (Pd2(dba)3), and 0.02 molar equivalent of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3). tert-Butylphosphine (t-Bu3P), 2 molar equivalents of sodium tert-butoxide (NaOBu-t), and 10 times the weight of the chlorine-containing compound in toluene were added. The system was purged with nitrogen, and the reaction solution was heated to reflux and stirred for 180 min. The reaction solution was then cooled to 70 °C and superheated on a silica gel column. The mother liquor was concentrated to one-third of its volume, and one-sixth the volume of the reaction solution in ethanol was added. The mixture was stirred at room temperature for 1 h and then filtered. The solution was then purified by recrystallization and silica gel chromatography, and dried to obtain a solid with a yield of 75%. 1 H NMR (400 MHz, 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).

[0136] The preparation method of BH2 in Synthetic Example 10 is as follows: In a reaction flask, 1 molar equivalent of 6-bromo-1,2,3,4-tetrahydro-1,1,4,4-tetramethylanthracene, 1 molar equivalent of 1,2,3,4,5,6,7,8-octadeuter-10-(dibenzo[b,d]furan-2-yl)anthracene-9-yl)boronic acid, 0.1 molar equivalent of tetra(triphenylphosphine)palladium (Pd(PPh3)4) and 2 molar equivalents of potassium carbonate (K2CO3) are mixed, and 10 times the weight of the bromine-containing compound in toluene, 1.5 times the weight of the bromine-containing compound in ethanol and 1.5 times the weight of the bromine-containing compound in deionized water are added. The system is purged with nitrogen three times, the reaction mixture is heated to reflux, and the reaction is stirred for 3 hours. The reaction mixture was cooled to 50°C and allowed to stand to separate into layers. The upper organic phase was washed with 1.5 times the weight of the bromine-containing compound in deionized water. The organic phase was purified by regular column chromatography and recrystallization, and dried to obtain a solid with a yield of 81%. 1 H NMR (400 MHz, Chloroform-d) δ 8.03(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). The preparation method of Synthetic Example 11BH9 is as follows: In a reaction flask, 1 molar equivalent of 3-chloro-8,8,11,11-tetramethyl-4a,8,9,10,13b-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 tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) and 2 molar equivalents of potassium carbonate (K2CO3) are mixed, and 10 times the weight of the chlorinated compound in toluene, 1.5 times the weight of the chlorinated compound in ethanol and 1.5 times the weight of the chlorinated compound in deionized water are added. The system is purged with nitrogen 3 times, the reaction mixture is heated to reflux, and the reaction is stirred for 3 hours. The reaction mixture was cooled to 50°C and allowed to stand to separate into layers. The upper organic phase was washed with 1.5 times the weight of the chlorinated compound in deionized water. The organic phase was purified by regular column chromatography and recrystallization, and dried to obtain a solid with a yield of 76%. 1¹H NMR (400 MHz, Chloroform-d) δ 8.01 (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). The preparation method of RD2 in Synthesis Example 12 is as follows:

[0137] Four molar equivalents of RD2-1 and one molar equivalent of iridium trichloride hydrate were dissolved in 10 times the weight of RD2-1 in ethylene glycol diethyl ether and 1 times the weight of RD2-1 in water. The reaction mixture was heated to reflux under nitrogen protection and stirred for 24 hours. After cooling the reaction mixture to room temperature, 10 times the weight of RD2-1 in water was added dropwise, resulting in the precipitation of a large amount of solid. The solid was filtered, and the concentration of the filtrate was measured. The solid dried to obtain a red solid, which was RD2-2, with a yield of 70%.

[0138] One molar equivalent of compound RD2-2 and six molar equivalents of a diketone were dissolved in 10 times the weight of RD2-2 in ethylene glycol diethyl ether. Six molar equivalents of sodium carbonate were added, and the mixture was protected under nitrogen atmosphere. The mixture was stirred at 60°C for 24 hours. The reaction solution was purified by silica gel column chromatography and recrystallization, and dried to give red solid RD2, with a yield of 50%. 1 H NMR (400 MHz, Chloroform-d)δ 7.86 (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).

[0139] The preparation method of RD4 in Synthetic Example 13 is as follows:

[0140] Four molar equivalents of RD4-1 and one molar equivalent of iridium trichloride hydrate were dissolved in 10 times the weight of RD4-1 in ethylene glycol diethyl ether and 1 times the weight of RD4-1 in water. The reaction mixture was heated to reflux under nitrogen protection and stirred for 24 hours. After cooling the reaction mixture to room temperature, 10 times the weight of RD4-1 in water was added dropwise, resulting in the precipitation of a large amount of solid. The solid was filtered, and the filtrate was concentrated and dried to obtain a red solid, RD4-2, with a yield of 75%.

[0141] One molar equivalent of compound RD4-2 and six molar equivalents of a diketone were dissolved in 10 times the weight of RD4-2 in ethylene glycol diethyl ether. Six molar equivalents of sodium carbonate were added, and the mixture was protected under nitrogen atmosphere. The mixture was stirred at 60°C for 24 hours. The reaction solution was purified by silica gel column chromatography and recrystallization, and dried to give red solid RD4, with a yield of 42%. 1 ¹H NMR (400 MHz, Chloroform-d) δ 8.11 (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 1–13 provided HT-ref1, HT-ref2, HT-ref3, E-ref1, E-ref2, E-ref3, RH-ref1, RH-ref2, and RH-ref3, respectively. Compounds BH-Ref3, BH-Ref1, BH-Ref2, RD-Ref1, and RD-Ref2; the structures of these compounds are shown below.

[0142]

[0143]

[0144] .

[0145] Example 14 (Referring to Figure 1) provides a method for fabricating a blue fluorescent device, including the following steps: forming a transparent anode ITO film with a thickness of 150 nm on a glass substrate 1 to obtain a first electrode 2 as the anode, followed by vapor deposition. A mixture of compound HT2 and hole transport material was used as hole injection layer 3, with a mixing ratio of 3:97 (mass ratio). A 100 nm thick layer of compound HT2 was then deposited to obtain the first hole transport layer 4, followed by the deposition of a 20 nm thick layer of compound. The second hole transport layer 5 was obtained, and then compound BH2 material was deposited at a deposition rate of 95:5. 30nm, fabricate blue light-emitting units (fluorescent light-emitting layer 6), then evaporate 10nm. A hole-blocking layer 7 is formed, and then compound E1 is deposited by vapor deposition. A 30 nm thick electron transport layer 8 is formed by mixing materials in a 4:6 mass ratio. Then, a 3 nm thick ytterbium layer and a 10 nm thick magnesium-silver layer (mass ratio 1:9) are formed sequentially as the second electrode 9. Finally, a 70 nm thick capping layer material is deposited on top of this. , forming a covering layer 10.

[0146] Comparative Example 14 is implemented in the same way as Example 14, except that HT2 in the hole injection layer 3 and the first hole transport layer 4 is replaced with HT2 that has been sealed and heated for 240 hours in the thermal stability test; E1 of the compound in the electron transport layer 8 is replaced with E1 that has been sealed and 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 that has been sealed and heated for 240 hours in the thermal stability test.

[0147] Comparative Example 15 is implemented in the same way as Example 14, except that HT-ref1 is used to replace HT2 in hole injection layer 3 and first hole transport layer 4, E-ref1 is used to replace E1 in electron transport layer 8, and BH-ref1 is used to replace compound BH2 in blue light emitting unit (light emitting layer 6).

[0148] Comparative Example 16 is implemented in the same way as Example 14, except that the hole injection layer 3 and the first hole transport layer 4 are replaced by HT-ref1 which has been sealed and heated for 240 hours in the thermal stability test, replacing the HT-ref1 in Comparative Example 2; the electron transport layer 8 is replaced by E-ref1 which has been sealed and heated for 240 hours in the thermal stability test, replacing the E-ref1 in Comparative Example 2; and the blue light emitting unit (fluorescent light emitting layer 6) is replaced by BH-ref1 which has been sealed and heated for 240 hours in the thermal stability test, replacing the BH-ref1 in Comparative Example 2.

[0149] Example 15 This example provides a method for fabricating a red phosphorescent device, including the following steps: forming a transparent anode ITO film layer with a thickness of 150 nm on a glass substrate 1 to obtain a first electrode 102 as the anode, followed by vapor deposition. With hole transport materials The mixed material was used as hole injection layer 3, with a mixing ratio of 3:97 (mass ratio), followed by the deposition of a 100nm thick layer. The first hole transport layer 4 was obtained, and then a compound with a thickness of 100 nm was deposited by evaporation. A second hole transport layer 5 was obtained, and then 40 nm of compound RH2 and compound RD2 were deposited at a 95:5 evaporation ratio to fabricate red light emitting units 6, followed by the deposition of 10 nm... A hole-blocking layer 7 is formed, and then vapor-deposited. and A 30 nm thick electron transport layer 8 is formed by mixing in a 4:6 mass ratio, followed by the formation of a 100 nm thick magnesium-silver layer (mass ratio 1:9) as the second electrode 9.

[0150] Comparative Example 17 The specific implementation of Comparative Example 17 is the same as that of Example 15, except that the compounds RH2 and RD2 in the red light emitting unit 6 are replaced with RH2 and RD2 that have been sealed and heated for 240 hours in the thermal stability test.

[0151] Comparative Example 18 The specific implementation of Comparative Example 18 is the same as that of Example 15, except that the compounds RH2 and RD2 in the red light emitting unit 6 are replaced by RH-ref1 and RD-ref1, respectively.

[0152] Comparative Example 19 The specific implementation of Comparative Example 19 is the same as that of Example 15, except that RH-ref1 and RD-ref1 in the red light emitting unit 6 are replaced by RH-ref1 and RD-ref1 that have been sealed and heated for 240 hours in the thermal stability test.

[0153] Performance Test 1. Evaporation Temperature Comparison: The evaporation temperatures of the compounds in Examples 1-13 were compared with those of the corresponding naphthalene-containing compounds in Comparative Examples 1-13. Experimental Method: 5g of material was added to a vacuum chamber containing a heating source and a 50cm³ boron nitride crucible. The vacuum level was 5*10⁻⁸ torr, and the temperature was monitored at an evaporation rate of 10A / h.

[0154] The compounds in Examples 1-13 exhibited lower evaporation temperatures compared to the naphthalene-containing compounds in Comparative Examples 1-13. The results are shown in Table 1.

[0155] 2. Thermal Stability Test: Thermal stability tests were conducted on the compounds in Examples 1, 4, 7, 10, and 12, and the compounds in Comparative Examples 1, 4, 7, 10, and 12. The experimental method was as follows: A quartz tube with a diameter of 10 mm and a length of 150 mm was prepared, with one end sealed and the other unsealed. The test material was added to the unsealed end, and the quartz tube was evacuated to 1*10-6 torr. The unsealed end was then heat-sealed. The sealed quartz tube was placed in a heating furnace and heated at 10 Å / h plus 40 °C for 240 hours. Purity was determined by liquid chromatography, and the experimental results are shown in Table 2.

[0156] 3. The device tests in Examples 14 and 14-16 were performed using a combination of a Keithley power supply and an MS-75 spectroradiometer. The voltage was 10 mA / cm². 2 The voltage at that time, with an efficiency of 10mA / cm 2 The current efficiency at that time is expressed as the color coordinate CIEy value divided by the value (unit: Cd / A / CIEy), and the lifetime is 10 mA / cm. 2 The time required for the brightness to decay to 95% of the initial brightness under current conditions. Using device example 14 as the 100% result, Example 14: voltage 4.0V, efficiency 141Cd / A / CIEy, 95% lifetime 650 hours. The results of the comparative examples are shown in Table 3.

[0157] The device tests in Examples 15 and 17-19 were performed using a combination of a Keithley power supply and an MS-75 spectroradiometer. The voltage was 10 mA / cm². 2 The voltage at that time, with an efficiency of 10mA / cm 2 The current efficiency at that time is expressed as the color coordinate CIEy value divided by the value (unit: Cd / A / CIEy), and the lifetime is 10 mA / cm. 2 The time required for the brightness to decay to 95% of the initial brightness under current conditions. Using device example 15 as the 100% result, Example 15: voltage 3.7V, efficiency 173Cd / A / CIEy, 95% lifetime 3200 hours. The results of the comparative example are shown in Table 4.

[0158] Table 1

[0159] Table 2

[0160] Table 3

[0161] Table 4

Claims

1. An OLED luminescent organic material, characterized in that, It includes a hole transport layer material, a light-emitting layer material, and an electron transport layer material; the light-emitting layer material includes a fluorescent light-emitting layer material; the fluorescent light-emitting layer material includes a blue fluorescent light-emitting host material; the blue fluorescent light-emitting host material has a structure shown in any one of Formulas 10 and 11; the structure of Formula 10 is as follows: In Formula 10, R1, R2, R3, and R4 are methyl groups, R5 and R6 are hydrogen or deuterium, Ra is hydrogen or deuterium, n is 2, m is 0-3, L is a single bond, a substituted or unsubstituted phenylene group, and R7-R... 14 All are hydrogen or deuterium, and Ar is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl groups, wherein the C6-C30 aryl or C3-C30 heteroaryl group in Ar is selected from phenyl, diphenyl, naphthyl, phenanthryl, dimethylfluorenyl, carbazole; the structure of Formula 11 is as follows: In Formula 11, R1, R2, R3, and R4 are methyl groups, R5 and R6 are hydrogen or deuterium, Ra is hydrogen or deuterium, n is 2, m is 0-3, X is O, L is a single bond or a substituted or unsubstituted phenylene group, and R7-R... 14 All are hydrogen or deuterium, and Ar is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl groups. The C6-C30 aryl or C3-C30 heteroaryl groups in Ar are selected from phenyl, diphenyl, naphthyl, phenanthryl, dimethylfluorenyl, and carbazolyl. All hydrogen atoms in Formulas 10 and 11 above can be substituted with deuterium atoms.

2. The OLED light-emitting organic material according to claim 1, characterized in that, The hole transport layer material has a structure shown in any one of Formula 2, Formula 3, and Formula 4; the structure of Formula 2 is as follows: In Formula 2, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra is selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; m is 0 to 3; L1, L2, and L3 are selected from single bonds, substituted or unsubstituted C6 to C30 aryl groups, or C3 to C30 heteroaryl groups; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted C6 to C30 aryl groups or C3 to C30 heteroaryl groups; all hydrogen atoms in Formula 2 can be substituted by deuterium atoms, C1 to C6 alkyl groups, C3 to C6 cycloalkyl or heterocycloalkyl groups; the structure of Formula 3 is as follows: In Formula 3, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra and Rb are each independently selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; X is selected from CR7R8, NR9, O, and S; R7-R9 are selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl groups, and C2 to C30 heteroaryl groups. Cycloalkyl groups, R7-R8 can be linked by any bond to form an aliphatic ring; m is 0-2; p is 0-3; L is selected from single bonds, substituted or unsubstituted C6-C30 aryl or C3-C30 heteroaryl groups; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl or C3-C30 heteroaryl groups; all hydrogen atoms in Formula 3 can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups or heterocycloalkyl groups; the structure of Formula 4 is as follows: Formula 4: R1~R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1~C4 alkyl groups, and n is 1 or 2; Ra represents hydrogen atoms, C1~C30 alkyl groups, C3~C30 cycloalkyl or heterocycloalkyl groups, C6~C30 aryl groups, and C3~C30 heteroaryl groups; m is selected from 0~2; R7~R 18 Selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, R7~R 18 At least one of them is L is selected from single bonds, substituted or unsubstituted C6-C30 aryl or C3-C30 heteroaryl; Ar1 ​​and Ar2 are each independently selected from substituted or unsubstituted C6-C30 aryl or C3-C30 heteroaryl; all hydrogen atoms in Formula 4 can be replaced by deuterium atoms, C1-C6 alkyl, C3-C6 cycloalkyl or heterocycloalkyl.

3. The OLED light-emitting organic material according to claim 1, characterized in that, The electron transport layer material has a structure shown in any one of Formulas 5, 6, and 7; the structure of Formula 5 is as follows: In Formula 5, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra represents hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; m is selected from 0 to 2; L is selected from single bonds, substituted or unsubstituted C6 to C30 arylene groups, or C3 to C30 heteroarylene groups; all hydrogen atoms in Formula 5 can be substituted by deuterium atoms, C1 to C6 alkyl groups, C3 to C6 cycloalkyl or heterocycloalkyl groups; the electron transport layer includes Formula 6; In Formula 6, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra and Rb are each independently selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; X is selected from CR7R8, NR9, O, and S; R7-R9 are selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl groups, and C2 to C30 heterocycloalkyl groups; R7-R8 can be connected by any bond to form an aliphatic ring; m is 0 to 2; p is 0 to 3; L is selected from single bonds, substituted or unsubstituted C6 to C30 aryl groups, or C3 to C30 heteroaryl groups; all hydrogen atoms in Formula 6 can be substituted by deuterium atoms, C1 to C6 alkyl groups, C3 to C6 cycloalkyl groups, or heterocycloalkyl groups; the structure of Formula 7 is... In Formula 7, R1 to R6 are each independently selected from hydrogen atoms, substituted or unsubstituted C1 to C4 alkyl groups, and n is 1 or 2; Ra represents hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl or heterocycloalkyl groups, C6 to C30 aryl groups, and C3 to C30 heteroaryl groups; X is selected from CR7R8, NR9, O, and S; R7 to R9 are selected from hydrogen atoms, C1 to C30 alkyl groups, C3 to C30 cycloalkyl groups, and C2 to C30 heterocycloalkyl groups; R7 to R8 can be connected by any bond to form an aliphatic ring; m is selected from 0 to 2; R7 to R 18 Selected from hydrogen atoms, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C3-C30 cycloalkyl or heterocycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, R7~R 18 At least one of them is L is selected from single-bonded, substituted, or unsubstituted C6-C30 arylene or C3-C30 heteroarylene; all hydrogen atoms in Formula 7 can be replaced by deuterium atoms, C1-C6 alkyl groups, C3-C6 cycloalkyl groups, or heterocycloalkyl groups; Electron in Formulas 5, 6, and 7 Each acceptor is independently selected from naphthyl, anthracene, phenanthryl, pyrenyl, peryl, fluorenyl, fluoranyl, pyridyl, pyrroleyl, pyrimidinyl, pyridazinyl, imidazolyl, pyrazolyl, isozolyl, thiazolyl, isothiazolyl, triazolyl, diazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, pyrazinyl, azinyl, thiazolyl, dioxazinyl, dioxazinyl, triazinyl, tetraazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, acridineyl, xanthyl, phenanthridineyl, diazanaphthyl, triazaindenyl, indoleyl, dihydroindoleyl, nitro-indenyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl Benzoxazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazoyl, benzocarbazoyl, dibenzocarbazoyl, indolocarbazoyl, indocarbazoyl, phenazinyl, phenanthrolinel, phenthiazinyl, imidazopyridyl, imidazophenanthidyl, benzimidazolylquinazolinyl, benzimidazolylphenanthidyl, spiro[fluorene-9,9'-oxazanthracene], phenylbinaphthyl, dinaphthofuryl, naphthobenzofuranyl, dinaphthiopheneyl, naphthobenzothiopheneyl, triphenylphosphine oxide, triphenylborane, 1-10 o-phenanthrolinel, cyano-substituted aryl or heteroaryl, fluorine-substituted aryl or heteroaryl, trifluoromethyl-substituted aryl or heteroaryl.

4. An OLED light-emitting device containing the OLED light-emitting organic material according to any one of claims 1-3, characterized in that, The OLED light-emitting device includes at least an anode, a cathode, and an organic layer.

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