CN-122003021-A - Organic electroluminescent device, deuterated mixture and display device

CN122003021ACN 122003021 ACN122003021 ACN 122003021ACN-122003021-A

Abstract

The invention provides an organic electroluminescent device, a deuterated mixture and a display device. The organic electroluminescent device comprises an anode, a cathode and an organic layer arranged between the anode and the cathode, wherein the material of the organic layer comprises a deuterated mixture and a doping material, the deuterated mixture comprises a deuterated mixture prepared by deuteration reaction of a compound A, and the doping material comprises a compound of the formula I. According to the invention, the organic layer material in the organic electroluminescent device is designed, and the organic electroluminescent device with excellent performance is prepared by using a specific deuterated mixture and a specific doping material.

Inventors

WANG ZHANQI
LI ZHIQIANG
GUO JINTAO
SONG BIN
XU LIWEI
HAN SHUAISHUAI
HONG HAOZHI
LU JINBO
HUANG CHANGGANG

Assignees

阜阳欣奕华新材料科技股份有限公司

Dates

Publication Date: 20260508
Application Date: 20241107

Claims (10)

1. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises an anode, a cathode and an organic layer between the anode and the cathode; The material of the organic layer comprises deuterated mixture and doping material; the deuterated mixture comprises a deuterated mixture prepared by deuteration reaction of the compound A; The compound A has the structure shown below; Wherein Ar 1 is selected from phenyl and naphthyl, ring A is selected from benzene ring and naphthalene ring, and Ar 1 is selected from benzene ring, ar 1 is selected from naphthalene ring, and ring A is selected from benzene ring; the doping material comprises a compound with a structure shown in the following formula I: Wherein Ar is selected from substituted or unsubstituted groups shown in the following formula I-1, and the groups shown in the formula I-1 are connected through sp 2 hybridized carbon atoms and N atoms in the compound shown in the formula I; n is selected from 0 or 1; Ar 1 ～Ar 4 is independently selected from any one of substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted structural group having the formula II-1 as shown below: In the group of the formula II-1, X is selected from O or S, and the group shown in the formula II-1 is connected with N atoms in the compound of the formula I through sp 2 hybridized carbon atoms; ar and Ar 1 ～Ar 4 are respectively and independently selected from at least one of-D, -F, -CN, C1-C12 alkyl, C1-C12 alkoxy or C6-C20 aryl; the compound of formula I contains at least 1 group of formula II-1.
2. The organic electroluminescent device according to claim 1, wherein the compound a is selected from any one of the following compounds: preferably, the deuteration rate of the deuteration mixture is 10% -99%; preferably, the deuteration rate of the deuteration mixture is 40-58%; preferably, the deuteration rate of the deuterated mixture is 70-90%.
3. The organic electroluminescent device according to claim 1 or 2, wherein n is selected from 0 and Ar is selected from a substituted or unsubstituted group having a structure represented by the following formula I-1A, the dotted line representing a linking site: The substituent of the substituent is selected from at least one of-D, -F, -CN, C1-C5 alkyl, C1-C5 alkoxy and C6-C15 aryl, preferably at least one of-D, -F, -CN, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, phenyl, naphthyl or biphenyl, more preferably at least one of-D, -F, -CN, methyl, ethyl, tert-butyl, phenyl or naphthyl; Preferably, n is selected from 1, and Ar is selected from any one of a substituted or unsubstituted group having a structure shown in the following formula I-1B, a substituted or unsubstituted group having a structure shown in the following formula I-1C, and a dotted line represents a connecting site: The substituted substituents in the groups of formula I-1B and formula I-1C are each independently selected from at least one of-D, -F, -CN, C1-C5 alkyl, C1-C5 alkoxy, C6-C15 aryl, preferably at least one of-D, -F, -CN, methyl, ethyl, propyl, tert-butyl, methoxy, ethoxy, phenyl, naphthyl or biphenyl, more preferably phenyl.
4. An organic electroluminescent device according to any one of claims 1 to 3, wherein the C6-C40 aryl group is selected from any one or a combination of at least two of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, triphenylenyl, or fluoranthenyl; preferably, the C1-C12 alkyl is selected from any one of methyl, ethyl, propyl, tertiary butyl, cyclohexyl, octyl or adamantyl; preferably, the C1-C12 alkoxy is selected from any one of methoxy, ethoxy, propoxy, butoxy, pentoxy or hexoxy; preferably, the C6-C20 aryl is selected from any one of phenyl, biphenyl, terphenyl or naphthyl.
5. The organic electroluminescent device of any one of claims 1-4, wherein each Ar 1 ～Ar 4 is independently selected from any one of a group of formula II-1, a substituted or unsubstituted C6-C20 aryl, and at least one of Ar 1 ～Ar 4 is selected from a group of formula II-1; The substituent group of the substituent is selected from at least one of C1-C10 alkyl, C1-C5 alkoxy and C6-C15 aryl, preferably at least one of methyl, ethyl, propyl, tertiary butyl, cyclohexyl, methoxy, ethoxy, propoxy, phenyl or naphthyl; Preferably, any one of Ar 1 、Ar 2 is selected from the group consisting of a group of formula II-1, and the other is selected from the group consisting of substituted or unsubstituted phenyl; The substituent group of the substituent is at least one selected from methyl, tertiary butyl, cyclohexyl, methoxy or propoxy; Preferably, any one of Ar 3 、Ar 4 is selected from the group consisting of a group of formula II-1, and the other is selected from the group consisting of substituted or unsubstituted phenyl; The substituent of the substituent is selected from at least one of methyl, tertiary butyl, cyclohexyl, methoxy or propoxy.
6. The organic electroluminescent device of any one of claims 1-5, wherein the compound of formula I comprises any one of the following compounds: Preferably, the compound of formula I is selected from compound 26 or compound 45, further preferably compound 45:
7. The organic electroluminescent device of any one of claims 1-6, wherein the organic layer of the organic electroluminescent device comprises a light-emitting layer; The material of the light-emitting layer comprises a host material, and the host material comprises a deuterated mixture prepared by deuteration reaction of the compound A.
8. A deuterated mixture comprising a deuterated mixture prepared from compound a via a deuteration reaction; The compound A has the following structure: Wherein Ar 1 is selected from phenyl and naphthyl, when Ar 1 is selected from phenyl, ar 1 is selected from naphthalene, ar 1 is selected from naphthyl, and when Ar is selected from benzene, ar is selected from benzene.
9. The deuterated mixture according to claim 8, wherein compound a is selected from any one of the following compounds: preferably, the deuteration rate of the deuteration mixture is 10% -99%; preferably, the deuteration ratio of the deuterated mixture is from 40 to 58%; preferably, the deuteration ratio of the deuterated mixture is from 70 to 90%.
10. A display device, characterized in that the display device comprises an organic electroluminescent device as claimed in any one of claims 1 to 7.

Description

Organic electroluminescent device, deuterated mixture and display device Technical Field The invention belongs to the technical field of organic electroluminescent devices, and particularly relates to an organic electroluminescent device, a deuterated mixture and a display device. Background The organic electroluminescence phenomenon has been discovered in 1963 but has not been paid attention to at the time, and the technology is focused again until the thin film type organic electroluminescent device (OLED) with high brightness and high efficiency, which is driven by direct current and low voltage, is made by the Tang research group of Kodak company in the United states in 1987. Compared with other display technologies, the OLED technology has the outstanding advantages of low power consumption, high response speed, easiness in bending, wide viewing angle, capability of displaying in a large area, full luminescent color and the like, and can be compatible with various existing standards and technologies to prepare a low-cost luminescent device, thereby exhibiting wide application prospect in the aspect of realizing color flat panel display. Over the last decades, OLEDs have evolved as a new display technology, with wide spread use in the fields of flat panel displays, flexible displays, solid state lighting and in-vehicle displays. Therefore, development of an organic electroluminescent device excellent in performance and a material used therein is an important point of study in the art. Disclosure of Invention In view of the shortcomings of the prior art, it is an object of the present invention to provide an organic electroluminescent device, deuterated mixture, and display device. According to the invention, the organic layer material in the organic electroluminescent device is designed, and the organic electroluminescent device with excellent performance is prepared by using a specific deuterated mixture and a specific doping material. In a first aspect, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode; The material of the organic layer comprises deuterated mixture and doping material; the deuterated mixture comprises a deuterated mixture prepared by deuteration reaction of the compound A; The compound A has the structure shown below; Wherein Ar 1 is selected from phenyl and naphthyl, ring A is selected from benzene ring and naphthalene ring, and Ar 1 is selected from benzene ring, ar 1 is selected from naphthalene ring, and ring A is selected from benzene ring; the doping material comprises a compound with a structure shown in the following formula I: Wherein Ar is selected from substituted or unsubstituted groups shown in the following formula I-1, and the groups shown in the formula I-1 are connected through sp 2 hybridized carbon atoms and N atoms in the compound shown in the formula I; n is selected from 0 or 1; Ar 1～Ar4 is independently selected from any one of substituted or unsubstituted C6-C40 aryl, substituted or unsubstituted structural group having the formula II-1 as shown below: In the group of the formula II-1, X is selected from O or S, and the group shown in the formula II-1 is connected with N atoms in the compound of the formula I through sp 2 hybridized carbon atoms; ar and Ar 1～Ar4 are respectively and independently selected from at least one of-D, -F, -CN, C1-C12 alkyl, C1-C12 alkoxy or C6-C20 aryl; The compound of the formula I at least contains 1 group shown in the formula II-1. According to the invention, the deuteration reaction is carried out on the anthracene compound (compound A) with a specific structure, so that complicated purification work is avoided, the preparation method is simple, the reaction condition is mild, the post-treatment is simple, and the deuteration mixture can be obtained after the deuteration reaction is carried out on the anthracene compound (compound A) with a specific structure, so that when the prepared deuteration mixture is used as a main material of a luminescent layer, the prepared OLED luminescent device has good comprehensive performance and excellent performance. According to the invention, the organic layer material in the organic electroluminescent device is designed, and the organic electroluminescent device with excellent performance is prepared by using a specific deuterated mixture and a specific doping material. In the present invention, C6-C40 may be C6, C8, C10, C12, C16, C20, C24, C28, C30, C32, C36, C40, or the like. C6-C20 may be C6, C8, C10, C12, C16 or C20, etc. C1-C12 may be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11 or C12. In the present invention, "-D" represents a deuterium atom, and the same applies to the following. It should be noted that, in the organic reaction process, when there is no significant difference in the reactive sites on the reactive molecule, it is difficult to perform substitution reaction at the