Organic electroluminescent element and electronic device

Patent metadata

Field	Value
Publication number	US-12022728-B2
Application number	US-202217733306-A
Country	US
Kind code	B2
Filing date	Apr 29, 2022
Priority date	Feb 18, 2016
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

The compound represented by formula (1):

wherein A, B, R 1 , and R 2 are as defined in the description,

provides organic electroluminescence (EL) devices 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-I), (2-2), (2-3), (2-4) (2-5), (2-6) and 2-8)):

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
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 , R 21 to R 26 , R 31 to R 38 , and R 41 to R 48 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 ;
with the proviso that R 12 and R 22 in formula (2-1) and R 15 and R 25 in formula (2-6) are not a substituted or unsubstituted aryl having 6 to 30 carbon atoms;
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 at least one of R 11 to R 16 and R 21 to R 26 of each of formulae (2-1), (2-2), (2-3), (2-4), (2-5), and (2-6) is a group represented by —Z—R a ; at least one of R 11 to R 16 and R 31 to R 38 of formula (2-8) is a group represented by —Z—R a ;
adjacent two selected from R 11 to R 16 , R 21 to R 26 , R 31 to R 38 , R 41 and R 48 may be bonded to each other to form a ring structure.

2. The compound according to claim 1 , wherein the compound is represented by any of formulae (2-1) to (2-6);
each of R 11 to R 16 and R 21 to R 26 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 substituted 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 105 )(R 103 ), or a group represented by —Z—R a ;
provided that at least one of R 11 to R 16 and R 21 to R 26 of each of formulae (2-1), (2-2), (2-3), (2-4), (2-5), and (2-6) is 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; and
adjacent two selected from R 11 to R 16 and R 21 to R 26 may be bonded to each other to form a ring structure.

3. A material for organic electroluminescence devices comprising the compound according to claim 1 .

4. An organic electroluminescence device comprising an organic thin film layer which comprises one or more layers and is disposed between a cathode and an anode; wherein the organic thin film layer comprises a light emitting layer and at least one layer of the organic thin film layer comprises the compound according to claim 1 .

5. The organic electroluminescence device according to claim 4 , wherein the light emitting layer comprises the compound.

6. The organic electroluminescence device according to claim 4 , wherein the at least one layer comprises the compound and an anthracene derivative represented by 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.

7. The organic electroluminescence device according to claim 4 , therein the organic thin film layer comprises an electron transporting layer and the electron transporting layer comprises the compound.

8. The organic electroluminescence device according to claim 4 , wherein the organic thin film layer comprises a hole transporting layer and the hole transporting layer comprises the compound.

9. The organic electroluminescence device according to claim 4 , wherein 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.

10. An electronic device comprising the organic electroluminescence

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

• H10K71/00

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

• H10K85/624 Primary

  containing six or more rings · CPC title

• C07C211/61 Primary

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C07C2603/97

  containing five-membered rings · CPC title