IP Library › Granted Patent US 9,902,687
Granted Patent B2
US 9,902,687 · App. 14/908,929 · Granted Feb 27, 2018

Compound

Inventors: Hirokatsu Ito (Sodegaura, JP); Masahiro Kawamura (Sodegaura, JP); Yumiko Mizuki (Sodegaura, JP); Tasuku Haketa (Sodegaura, JP); Tomoharu Hayama (Sodegaura, JP); Ryota Takahashi (Sodegaura, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
C07C211/50C07C255/50H01L51/0062H01L51/0064H01L51/0067H01L2251/50
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Quick Facts
Patent No.
US 9,902,687
App. No.
14/908,929
Granted
Feb 27, 2018
Kind
B2
Abstract

A compound is represented by the following formula (1). In the formula (1), Ar is a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, R a are independently a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms, R b1 to R b4 are independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or the like, R c1 to R c10 are independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or the like, * is a bonding position at which one of R c1 to R c10 is bonded to either nitrogen atom, x is an integer from 0 to 3, y is an integer from 0 to 4, and z are independently an integer from 0 to 5.

Claims (81)

1. A compound of a formula (1),

wherein Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzo[c]phenanthryl group, a substituted or unsubstituted benzo[g]chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted fluoranthenyl group,

R a are independently a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms,

R b1 to R b4 are independently a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms, a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms, a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 15 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 15 carbon atoms, a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms, a substituted or unsubstituted arylamino group including 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group including 3 to 30 ring atoms,

R c1 to R c10 are independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms,

a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms,

a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms,

a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms,

a substituted or unsubstituted alkoxy group including 1 to 15 carbon atoms,

a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted alkylthio group including 1 to 15 carbon atoms,

a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted arylamino group including 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted heteroaryl group including 3 to 30 ring atoms, or

a single bond that is bonded to either nitrogen atom,

* is a bonding position at which any of R c1 to R c10 is bonded to either nitrogen atom,

x is an integer from 0 to 3,

y is an integer from 0 to 4,

z are independently an integer from 0 to 5,

a plurality of R b1 are either identical or different when x is an integer equal to or larger than 2, a plurality of R b2 are either identical or different when y is an integer equal to or larger than 2, and a plurality of R b3 or R b4 are either identical or different when z is an integer equal to or larger than 2,

when R a is substituted with a substituent, the substituent is an alkyl group including 1 to 10 carbon atoms, a cycloalkyl group including 3 to 10 ring carbon atoms, an alkylsilyl group including 3 to 30 carbon atoms, an arylsilyl group including 6 to 60 carbon atoms, an alkoxy group including 1 to 10 carbon atoms, aryloxy group including 6 to 20 ring carbon atoms, an alkylthio group including 1 to 10 carbon atoms, an arylthio group including 6 to 20 ring carbon atoms, an arylamino group including 12 to 30 ring carbon atoms, an aryl group including 6 to 20 ring carbon atoms, or a heteroaryl group including 5 to 20 ring atoms.

2. The compound according to claim 1 , the compound being of a formula (2),

wherein Ar, R a , R b1 to R b4 , R c1 to R c10 , x, z, and * are the same as defined for the formula (1).

3. The compound according to claim 1 , wherein R c1 to R c10 are independently a hydrogen atom, a halogen atom, a cyano group,

a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms,

a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms,

a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms,

a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms,

a substituted or unsubstituted alkoxy group including 1 to 15 carbon atoms,

a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted alkylthio group including 1 to 15 carbon atoms,

a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted heteroaryl group including 3 to 30 ring atoms, or

a single bond that is bonded to either nitrogen atom.

4. The compound according to claim 1 , the compound being of a formula (3),

wherein Ar, R a , R b1 to R b4 , R c2 to R c10 , x, z, and * are the same as defined for the formula (1).

5. The compound according claim 1 , the compound being of a formula (4),

wherein Ar, R a , R b1 to R b4 , x, and z are the same as defined for the formula (1), and R c2 to R c5 and R c7 to R c10 are independently a hydrogen atom, a halogen atom,

a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms, a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms, a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 15 carbon atoms,

a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted alkylthio group including 1 to 15 carbon atoms,

a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted arylamino group including 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or

a substituted or unsubstituted heteroaryl group including 3 to 30 ring atoms.

6. The compound according to claim 5 , the compound being of a formula (4-1),

wherein Ar, R a , R b1 to R b4 , R c3 , R c8 , x, and z are the same as defined for the formula (4).

7. The compound according to claim 6 , wherein R c3 and R c8 are independently a hydrogen atom, an alkyl group including 1 to 6 carbon atoms, or a cycloalkyl group including 1 to 6 carbon atoms.

8. The compound according to claim 1 , the compound being of a formula (5),

wherein Ar, R a , R b1 to R b4 , x, and z are the same as defined for the formula (1), and R c2 and R c4 to R c10 are independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms,

a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms,

a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms,

a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms,

a substituted or unsubstituted alkoxy group including 1 to 15 carbon atoms,

a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted alkylthio group including 1 to 15 carbon atoms,

a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms,

a substituted or unsubstituted arylamino group including 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or

a substituted or unsubstituted heteroaryl group including 3 to 30 ring atoms.

9. The compound according to claim 8 , the compound being of a formula (5-1),

wherein Ar, R a , R b1 to R b4 , R c7 , x, and z are the same as defined for the formula (5).

10. The compound according to claim 9 , wherein R c7 is a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms.

11. The compound according to claim 1 , wherein the benzene ring-containing group to which R b1 is bonded has a structure in which R b1 and Ar are not bonded at the para position with respect to the bonding position at which the N atom is bonded, and the benzene ring-containing group to which R b2 is bonded has a structure in which R b2 is not bonded at the para position with respect to the bonding position at which the N atom is bonded.

12. The compound according to claim 1 , wherein the benzene ring-containing group to which R b1 is bonded is represented by a formula (10), and the benzene ring-containing group to which R b2 is bonded is represented by a formula (11),

wherein Ar, R a , R b1 , R b2 , and x are the same as defined for the formula (1).

13. The compound according to claim 1 , wherein the benzene ring-containing group to which R b3 is bonded is represented by a formula (12), and the benzene ring-containing group to which R b4 is bonded is represented by a formula (13),

wherein R b3 and R b4 are the same as defined for the formula (1),

R b3 ′ and R b4 ′ are independently a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, or a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms, and

z1 are independently an integer from 0 to 4.

14. The compound according to claim 1 , wherein R b1 to R b4 are independently a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms, a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms, a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms, a substituted or unsubstituted alkoxy group including 1 to 15 carbon atoms, a substituted or unsubstituted aryloxy group including 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group including 1 to 15 carbon atoms, a substituted or unsubstituted arylthio group including 6 to 30 ring carbon atoms, a substituted or unsubstituted arylamino group including 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group including 3 to 30 ring atoms.

15. The compound according to claim 1 , wherein R b1 to R b4 are independently a cyano group, an unsubstituted phenyl group, a substituted or unsubstituted alkyl group including 1 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 15 carbon atoms, a substituted or unsubstituted alkylsilyl group including 1 to 45 carbon atoms, a substituted or unsubstituted arylsilyl group including 6 to 50 carbon atoms, or a substituted or unsubstituted aryl group including 6 to 30 ring carbon atoms.

16. The compound according to claim 1 , wherein R a are independently a substituted or unsubstituted alkyl group including 1 to 6 carbon atoms.

17. The compound according to claim 1 , the compound being a material for an organic electroluminescence device.

18. The compound according to claim 1 , the compound being an emitting material for an organic electroluminescence device.

19. The compound according to claim 1 , the compound being a doping material for an organic electroluminescence device.

20. An organic electroluminescence device comprising a cathode, an anode, and one or more organic thin film layers that are provided between the cathode and the anode, the one or more organic thin film layers comprising at least an emitting layer, and at least one organic thin film layer included in the one or more organic thin film layers comprising the compound according to claim 1 either alone or as a component of a mixture.

21. The organic electroluminescence device according to claim 20 , wherein the at least one organic thin film layer is the emitting layer.

22. The organic electroluminescence device according to claim 20 , wherein the compound is a dopant material.

23. An electronic apparatus comprising the organic electroluminescence device according to claim 20 .

24. The compound according to claim 1 , wherein R a are independently an unsubstituted alkyl group including 1 to 15 carbon atoms, or an unsubstituted cycloalkyl group including 3 to 15 carbon atoms.

25. The compound according to claim 1 , wherein R b1 to R b4 are independently an unsubstituted phenyl group, or an unsubstituted alkyl group including 1 to 15 carbon atoms.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2016
From: ITO, HIROKATSU; KAWAMURA, MASAHIRO; MIZUKI, YUMIKO; HAKETA, TASUKU; HAYAMA, TOMOHARU; TAKAHASHI, RYOTA
To: IDEMITSU KOSAN CO., LTD.
Reel/Frame 037729/0889 →
Priority Claims (1)
JP 2014-191964 · Sep 19, 2014 · national
Continuity (1)
Related Publication 20170183291A1 · Jun 29, 2017