Organic electroluminescent element and electronic device

Patent metadata

Field	Value
Publication number	US-12492162-B2
Application number	US-202418645413-A
Country	US
Kind code	B2
Filing date	Apr 25, 2024
Priority date	Feb 18, 2016
Publication date	Dec 9, 2025
Grant date	Dec 9, 2025

Abstract

Compounds of formulae (2-7) or (2-9) are provided:

Also provided are organic electroluminescence (EL) devices containing the compounds having a high emission efficiency when operated at low voltage and a long lifetime and electronic devices including such organic EL devices.

First claim

The invention claimed is:

1 . A compound of formula (2-7) or (2-9):

wherein:
each of R 1 and R 2 is independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, or a group represented by —Si(R 101 )(R 102 )(R 103 ) or a group represented by —Z—R a ;
R 1′ s and R 2′ s, if present, may be the same or different, and R 1′ s and R 2′ s may be bonded to each other to form a ring structure, respectively;
Z is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a divalent linking group wherein two to four groups selected from the arylene group and the heteroarylene group are linked together;
Z′s, if present, may be the same or different;
R a is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
each of n1 and n2 is an integer of 0 to 4;
R a′ s, if present, may be the same or different;
each of R 11 to R 16 , and R 31 to R 38 , is independently a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a group represented by —Si (R 101 )(R 102 )(R 103 ), or a group represented by —Z—R a ;
each of R 101 to R 103 is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms:
provided that one of R 1 , R 2 , R 11 to R 16 and R 31 to R 38 is a group represented by —Z—R a , and
adjacent two selected from R 11 to R 16 , and R 31 to R 38 may be bonded to each other to form a ring structure.

2 . A material for organic electroluminescence devices comprising the compound of formula (2-7) or formula (2-9) according to claim 1 .

3 . An organic electroluminescence device, comprising:
an anode; a cathode; and an organic thin film layer disposed between the cathode and the anode, wherein the organic thin film layer comprises a light emitting layer and at least one other layer and at least one layer of the organic thin film layer comprises the compound of formula (2-7) or the compound of formula (2-9) according to claim 1 .

4 . The organic electroluminescence device according to claim 3 , wherein the light emitting layer comprises the compound of formula (2-7) or formula (2-9).

5 . The organic electroluminescence device according to claim 3 , wherein the at least one other layer comprises the compound of formula (2-7) or formula (2-9) and further comprises an anthracene derivative of formula (5):

wherein:
each of Ar 11 and Ar 12 is independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms or a substituted or unsubstituted fused ring group having 8 to 50 ring atoms; and
each of R 101 to R 108 is independently a group selected from a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, a group comprising a combination of the monocyclic group and the fused ring group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, a halogen atom, and a cyano group.

6 . The organic electroluminescence device according to claim 3 , wherein the at least one other layer of the organic thin film layer comprises an electron transporting layer and the electron transporting layer comprises the compound of formula (2-7) or formula (2-9).

7 . The organic electroluminescence device according to claim 3 , wherein the at least one other layer of the organic thin film layer comprises a hole transporting layer and the hole transporting layer comprises the compound of formula (2-7) or formula (2-9).

8 . The organic electroluminescence device according to claim 3 , wherein the at least one other layer of the organic thin film layer comprises an electron transporting layer and a blocking layer between the electron transporting layer and the light emitting layer, and the blocking layer comprises the compound of formula (2-7) or formula (2-2).

9 . An electronic device comprising the organic electroluminescence device according to claim 3 .

10 . The compound of formula (2-7) or (2-9) according to claim 1 , wherein R a is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

11 . The compound of formula (2-7) or (2-9) according to claim 1 , wherein one of R 11 to R 16 and R 31 to R 38 is a group represented by —Z—R a .

12 . The compound of formula (2-7) or (2-9) according to claim 1 , wherein one of R 11 to R 16 and R 31 to R 38 is a group represented by —Z—R a and the others of R 11 to R 16 and R 31 to R 38 are a hydrogen atom.

13 . An organic electroluminescence device, comprising:
an anode; a cathode; and an organic thin film layer disposed between the cathode and the anode, wherein the organic thin film layer comprises a light emitting layer and at least one other layer and at least one layer of the organic thin film layer comprises the compound of formula (2-7) or the compound of formula (2-9) according to claim 12 .

14 . The organic electroluminescence device according to claim 13 , wherein the light emitting layer comprises the compound of formula (2-7) or formula (2-9).

15 . The organic electroluminescence device according to claim 13 , wherein the at least one other layer comprises the compound of

Assignees

• Idemitsu Kosan Co

Inventors

• Takahashi Ryota
• Kato Tomoki
• Ito Hirokatsu
• Kawamura Masahiro
• Funahashi Masakazu
• Saito Hiroyuki
• Kawamura Yuichiro
• Takahashi Yoshiaki
• Masuda Tetsuya
• Kuma Hitoshi

Classifications

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C07C2603/97

  containing five-membered rings · CPC title

• H10K71/00

  Manufacture or treatment specially adapted for the organic devices covered by this subclass · CPC title

• H10K2102/351

  Thickness · CPC title

• H10K2101/27

  Combination of fluorescent and phosphorescent emission · CPC title