Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device

Patent metadata

Field	Value
Publication number	US-12069943-B2
Application number	US-201917298363-A
Country	US
Kind code	B2
Filing date	Dec 3, 2019
Priority date	Dec 3, 2018
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

The present invention relates to a compound represented by the formula (1):

wherein R 1 to R 4 and L 1 to L 4 are those defined in the specification, and Ar is the following formula (A) or (B):

wherein R 11 to R 18 and R 20 to R 29 are those defined in the specification, and Ar is one defined in the specification.

First claim

The invention claimed is:

1. A compound of formula (1):

wherein,
R 1 to R 4 are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
wherein when substituted, the substituents on R 1 to R 4 are each independently selected from the group consisting of an alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, a mono-, di- or tri-substituted silyl group having a substituent selected from an alkyl group having 1 to 30 carbon atoms, and an aryl group having 6 to 30 ring carbon atoms, and a heteroaryl group having 5 to 30 ring atoms,
L 1 to L 4 are each independently selected from the group consisting of a single bond and a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,
R 1 or L 1 does not bond to R 2 or L 2 to form a ring structure, and R 3 or L 3 does not bond to R 4 or L 4 to form a ring structure, R 1 does not bond to R 3 to form a ring structure, R 1 does not bond to R 4 to form a ring structure, R 2 does not bond to R 3 to form a ring structure, and R 2 does not bond to R 4 to form a ring structure, and
Ar is formula (A) or (B):

wherein,
R 11 to R 18 and R 20 to R 29 are each a hydrogen atom
provided that one selected from R 11 to R 18 is a single bond bonding to *a, and one selected from R 20 to R 29 is a single bond bonding to *b, and
Ar does not bond to a benzene ring bonding to Ar to form a ring structure.

2. The compound according to claim 1 , wherein R 1 to R 4 are each independently selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

3. The compound according to claim 2 , wherein in the substituted or unsubstituted biphenylyl group, the biphenylyl group is a p-, o-, or m-biphenylyl group.

4. The compound according to claim 2 , wherein in the substituted or unsubstituted biphenylyl group, the biphenylyl group is a p-biphenylyl group.

5. The compound according to claim 2 , wherein the substituted or unsubstituted terphenylyl group is a 1,1′:4′,1″-terphenyl-4-yl group, a 1,1′:3′,1″-terphenyl-4-yl group, or a 1,1′:3′,1″-terphenyl-2-yl group.

6. The compound according to claim 2 , wherein in the substituted or unsubstituted fluorenyl group, the fluorenyl group is a 1-, 2-, 3-, or 4-fluorenyl group.

7. The compound according to claim 2 , wherein in the substituted or unsubstituted fluorenyl group, the fluorenyl group is a 2-fluorenyl group or a 4-fluorenyl group.

8. The compound according to claim 2 , wherein in the substituted or unsubstituted dibenzofuranyl group, the dibenzofuranyl group is a 2- or 3-dibenzofuranyl group.

9. The compound according to claim 2 , wherein in the substituted or unsubstituted dibenzofuranyl group, the dibenzofuranyl group is a 2-dibenzofuranyl group.

10. The compound according to claim 2 , wherein in the substituted or unsubstituted dibenzothiophenyl group, the dibenzothiophenyl group is a 2- or 3-dibenzothiophenyl group.

11. The compound according to claim 2 , wherein in the substituted or unsubstituted dibenzothiophenyl group, the dibenzothiophenyl group is a 2-dibenzothiophenyl group.

12. The compound according to claim 2 , wherein in the substituted or unsubstituted carbazolyl group, the carbazolyl group is a 1-, 2-, 3-, or 4-carbazolyl group.

13. The compound according to claim 2 , wherein in the substituted or unsubstituted carbazolyl group, the carbazolyl group is a 2- or 3-carbazolyl group.

14. The compound according to claim 2 , wherein in the substituted or unsubstituted carbazolyl group, the carbazolyl group is a 2-carbazolyl group.

15. The compound according to claim 1 , wherein Ar is the formula (A), and R 11 or R 12 is a single bond bonding to *a.

16. The compound according to claim 1 , wherein Ar is the formula (B), and one selected from R 20 to R 23 and R 29 is a single bond bonding to *b.

17. The compound according to claim 1 , wherein Ar is the formula (B), and R 29 is a single bond bonding to *b.

18. The compound according to claim 1 , wherein L 1 to L 4 are a single bond.

19. The compound according to claim 1 , wherein the compound of formula (1) comprises at least one deuterium atom.

20. A material for organic electroluminescent devices comprising the compound according to claim 1 .

21. An organic electroluminescent device comprising a cathode, an anode, and organic layers between the cathode and the anode, wherein the organic layers comprise a light emitting layer, and at least one layer of the organic layers comprises the compound according to claim 1 .

22. The organic electroluminescent device according to claim 21 , wherein the organic layer comprises a hole transporting zone between the anode and the light emitting layer, and the hole transporting zone comprises the compound.

23. The organic electroluminescent device according to claim 21 , wherein the hole transporting zone comprises a first hole transporting layer on the anode side and a second hole transporting layer on the cathode side, and the first hole transporting layer, the second hole transporting layer, or both of them comprise the compound.

24. The organic electroluminescent device according to claim 23 , wherein the first hole transporting layer comprises the compound.

25. The organic electroluminescent device according to claim 23 , wherein the second hole transporting layer comprises the compound.

26. The organic electroluminescent device according to claim 25 , wherein the second hole transporting layer is adjacent to the light emitting layer.

27. The organic electroluminescent device according to claim 21 , wherein the light emitting layer contains a fluorescent light emitting material.

Assignees

• Idemitsu Kosan Co

Inventors

• Haketa Tasuku
• Ito Hirokatsu
• Kudo Yu

Classifications

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• H10K50/156

  comprising a multilayered structure · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title