Organic electroluminescent material and organic electroluminescent device comprising same

Patent metadata

Field	Value
Publication number	US-11778901-B2
Application number	US-202217718174-A
Country	US
Kind code	B2
Filing date	Apr 11, 2022
Priority date	Jun 19, 2019
Publication date	Oct 3, 2023
Grant date	Oct 3, 2023

Abstract

The present invention relates to an organic electroluminescent material and organic electroluminescent device thereof. The organic electroluminescent material has the structural formula as shown in formula 1. Compared with a monoamine structure containing an adamantyl group, the diamine structure disclosed in the present invention has higher HOMO energy level and hole mobility, and can exhibit higher efficiency and service life than a monoamine material device. The organic electroluminescent device comprising the organic electroluminescent material has lower driving voltage, and higher luminous efficiency and service life.

First claim

What is claimed is:

1. An organic electroluminescent material, having a structure as shown in chemical formula 1:

wherein R 2 , R 4 , and R 5 are identical or different, and are each independently selected from substituted or unsubstituted aryl with 6-30 carbon atoms, or substituted or unsubstituted heteroaryl with 1-30 carbon atoms;
R 1 and R 3 are identical or different, R 1 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, or substituted or unsubstituted naphthylene, and R 3 is selected from substituted or unsubstituted arylene with 6-25 carbon atoms, or substituted or unsubstituted heteroarylene with 5-18 carbon atoms;
substituents of R 1 , R 2 , R 3 , R 4 , and R 5 are identical or different, and are each independently selected from deuterium, cyano, nitro, alkyl group with 1-40 carbon atoms, alkenyl group with 2-40 carbon atoms, alkynyl group with 2-40 carbon atoms, heterocycloalkyl group with 2-40 carbon atoms, aralkyl group with 7-40 carbon atoms, heteroaralkyl group with 2-40 carbon atoms, aryl group with 6-40 carbon atoms, heteroaryl group with 1-40 carbon atoms, alkoxyl group with 1-40 carbon atoms, alkylthio group with 1-40 carbon atoms, alkylsilyl group with 1-45 carbon atoms, arylsilyl group with 6-50 carbon atoms, aryloxyl group with 6-30 carbon atoms or arylthio group with 6-30 carbon atoms; and
when there is more than one substituent, the substituents are identical or different.

2. The organic electroluminescent material according to claim 1 , wherein R 2 , R 4 , and R 5 are identical or different, and are each independently selected from substituted or unsubstituted aryl with 6-18 carbon atoms, or substituted or unsubstituted heteroaryl with 5-18 carbon atoms;
the substituents of R 1 , R 2 , R 3 , R 4 , and R 5 are identical or different, and are each independently selected from deuterium, cyano, nitro, alkyl group with 1-10 carbon atoms, aryl group with 6-15 carbon atoms or heteroaryl group with 3-12 carbon atoms; and
when there is more than one substituent, the substituents are identical or different.

3. The organic electroluminescent material according to claim 1 , wherein R 1 is selected from substituted or unsubstituted group W 1 , the unsubstituted group W 1 is selected from the following groups:

R 3 is selected from substituted or unsubstituted group the unsubstituted group W 1 ′ is selected from the following groups:

when the group W 1 and W 1 ′ is substituted by one or more substituents, the substituents of W 1 and W 1 ′ are each independently selected from the group consisting of deuterium, cyano, methyl, ethyl, propyl, tert-butyl, trimethylsilyl, phenyl, naphthyl, dibenzofuryl, dibenzothienyl and carbazolyl; and
when there is more than one substituent of the W 1 or W 1 ′ the substituents are identical or different.

4. The organic electroluminescent material according to claim 1 , wherein R 3 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted chrysenylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted naphthylene, substituted or unsubstituted azulenylene, substituted or unsubstituted indenylene, substituted or unsubstituted pyridylene, or substituted or unsubstituted imidazolylidene.

5. The organic electroluminescent material according to claim 1 , wherein R 3 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted naphthylene, substituted or unsubstituted 9,9-dimethylfluorenylidene, substituted or unsubstituted dibenzofurylene, substituted or unsubstituted dibenzothienylene, or substituted or unsubstituted carbazolylidene;
the “substituted” means to be independently substituted by substituent(s) selected from the following groups: deuterium, cyano, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, carbazolyl, dibenzofuryl and dibenzothienyl; and
when there are multiple substituents, the substituents are identical or different.

6. The organic electroluminescent material according to claim 1 , wherein R 2 , R 4 , and R 5 are identical to or different from each other, and are each independently selected from substituted or unsubstituted group Y 1 , the unsubstituted group Y 1 is selected from the following groups:

when the group Y 1 is substituted by one or more substituents, the substituents of Y 1 are each independently selected from the group consisting of deuterium, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, trimethylsilyl, phenyl, naphthyl, dibenzothienyl, and dibenzofuryl; and when there is more than one substituent of the Y 1 , the substituents are identical or different.

7. The organic electroluminescent material according to claim 1 , wherein R 2 , R 4 , and R 5 are identical or different, and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted naphthyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, or a group formed by linking two or three of the groups through a single bond;
the “substituted” means to be independently substituted by substituent(s) selected from the following groups: deuterium, cyano, methyl, ethyl, propyl, tert-butyl, phenyl, naphthyl, carbazolyl, dibenzofuryl, and dibenzothienyl; and
when there are a plurality of substituents, the substituents are identical or different.

8. The organic electroluminescent material according to claim 1 , wherein the substituents of R 1 , R 2 , R 3 , R 4 , and R 5 are identical or different, and are each independently selected from deuterium, cyano, alkyl with 1-4 carbon atoms, alkoxyl with 1-4 carbon atoms, trialkylsilyl with 3-9 carbon atoms, aryl with 6-15 carbon atoms, heteroaryl with 3-12 carbon atoms or triphenylsilyl.

9. The organic electroluminescent material according to claim 1 , wherein the substituents of R 1 , R 2 , R 3 , R 4 , and R 5 are identical or different, and are each independently selected from deuterium, cyano, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxyl, ethoxyl, trimethylsilyl, phenyl, pyridyl, 9,9-dimethylfluorenyl, dibenzofuryl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl or triphenylsilyl.

10. The organic electroluminescent material according to claim 1 , being selected from the following comp

Assignees

• Shaanxi Lighte Optoelectronics Mat Co Ltd

Inventors

• Ma Tiantian
• Nie Qiqi
• Feng Zhen
• Li Hongyan
• Sha Xunshan
• Sun Zhanyi
• Wang yalong

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K85/633 Primary

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07D209/86 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system · CPC title