IP Library Granted Patent US 10,270,040
Granted Patent B2
US 10,270,040 · App. 15/658,596 · Granted Apr 23, 2019

Oxygen-containing fused ring amine compound, sulfur-containing fused ring amine compound and organic electroluminescence device

Inventors: Yoichi Ikeda (Chiba, JP); Hirokatsu Ito (Chiba, JP); Masahiro Kawamura (Chiba, JP); Hiroyuki Saito (Chiba, JP); Takeshi Ikeda (Chiba, JP)
Assignee: IDEMITSU KOSAN CO., LTD.
H01L51/0061C07D209/80C07D235/08C07D307/91C07D403/14C07D405/04C07D409/14C07D497/04H01L51/0073H01L51/5012
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Quick Facts
Patent No.
US 10,270,040
App. No.
15/658,596
Granted
Apr 23, 2019
Kind
B2
Abstract

A fused amine compound including a furan ring or a thiophene ring and an organic electroluminescence device employing the amine compound. The organic electroluminescence device includes a cathode, an anode, and one or more organic thin film layers which are disposed between the cathode and the anode. The organic thin film layers include a light emitting layer and at least one layer of the organic thin film layers includes at least one amine compound.

Claims (39)

1. An amine compound represented by formula (I):

B A) n   (1)

wherein:

n is 1;

B represents a structure represented by formula (2) shown below;

A represents a group represented by formula (6) shown below:

wherein two adjacent groups in at least one pair of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 are bonded to each other to form a divalent group represented by formula (3):

n group of R 1 to R 8 and R a to R d represents a single bond which is bonded to the group A represented by formula (6);

each of R 1 to R 8 which does not form the divalent group and does not represent the single bond bonded to the group A represented by formula (6), and each of R a to R d which does not represent the single bond bonded to the group A represented by formula (6) are independently selected from 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 aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy 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 alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; and

X represents an oxygen atom; and

wherein:

Ar 1 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;

L represents an arylene group having 6 to 30 ring carbon atoms, a heteroarylene group having 5 to 30 ring atoms, or a divalent linking group formed by bonding 2 to 4 groups selected from the arylene groups and the heteroarylene groups;

L 2 represents a single bond, an arylene group having 6 to 30 ring carbon atoms, a heteroarylene group having 5 to 30 ring atoms, or a divalent linking group formed by bonding 2 to 4 groups selected from the arylene groups and the heteroarylene groups; and

HAr represents a structure represented by formula (7):

wherein:

X 2 represents an oxygen atom or a sulfur atom;

one of R 131 to R 138 represents a single bond bonded to L 2 , and the others of R 131 to R 138 each independently represent 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 aryl group having, 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy 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 alkylsilyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aryls group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

2. The amine compound according to claim 1 , wherein one pair selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 forms the divalent group represented by formula (3).

3. The amine compound according to claim 1 , wherein the structure B is represented by any of formulae (11) to (13):

wherein X and R 1 to R 8 are as defined above, and R 11 to R 14 , R 21 to R 24 , and R 31 to R 34 are defined as in R a to R d .

4. The amine compound according to claim 1 , wherein two pairs selected from R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 form the divalent groups represented by formula (3).

5. The amine compound according to claim 1 , wherein the structure B is represented by any of formulae (14) to (19):

wherein X and R 1 to R 8 are as defined above, and R 41 to R 48 , R 51 to R 58 , R 61 to R 68 , R 71 to R 78 , R 81 to R 88 , and R 91 to R 98 are defined as in R a to R d .

6. The amine compound according to claim 1 , wherein the structure B is represented by any of formulae (14) to (16):

wherein X, R 1 to R 8 , R 41 to R 48 , R 51 to R 58 , and R 61 to R 68 are as defined above.

7. The amine compound according to claim 1 , wherein one of R 132 , R 134 , R 135 , and R 137 represents a single bond bonded to L 2 .

8. An organic electroluminescence device which comprises a cathode, an anode, and one or more organic thin film layers which are disposed between the cathode and the anode, wherein the organic thin film layers comprise a light emitting layer, and at least one layer of the organic thin film layers comprises at least one amine compound according to claim 1 .

9. The organic electroluminescence device according to claim 8 , wherein the light emitting layer comprises the amine compound.

10. The organic electroluminescence device according to claim 8 , wherein the at least one layer comprises the amine compound and an anthracene derivative represented by formula (5a):

wherein each of Ar 11 and Ar 12 independently represents 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 independently represents 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 constituted of 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.

11. The organic electroluminescence device according to claim 10 , wherein each of Ar 11 and Ar 12 of formula (5a) independently represents the substituted or unsubstituted fused ring group having 8 to 50 ring atoms.

12. The organic electroluminescence device according to claim 10 , wherein one of Ar 11 and Ar 12 of formula (5a) represents the substituted or unsubstituted monocyclic group having 5 to 50 ring carbon atoms, and the other represents the substituted or unsubstituted fused ring group having 8 to 50 ring atoms.

13. The organic electroluminescence device according to claim 12 , wherein in formula (5a), Ar 12 represents a naphthyl group, a phenanthryl group, a benzanthryl group, a 9,9-dimethylfluorenyl group, or a dibenzofuranyl group, and Ar 11 represents an unsubstituted phenyl group or a phenyl group substituted with the monocyclic group or the fused ring group.

14. The organic electroluminescence device according to claim 12 , wherein in formula (5a), Ar 12 represents the substituted or unsubstituted fused ring group having 8 to 50 ring atoms, and Ar 11 represents an unsubstituted phenyl group.

15. The organic electroluminescence device according to claim 10 , wherein each of Ar 11 and Ar 12 of formula (5a) independently represents the substituted or unsubstituted monocyclic group having 5 to 50 ring atoms.

16. The organic electroluminescence device according to claim 15 , wherein each of Ar 11 and Ar 12 of formula (5a) independently represents a substituted or unsubstituted phenyl group.

17. The organic electroluminescence device according to claim 15 , wherein in formula (5a), Ar 11 represents an unsubstituted phenyl group, and Ar 12 represents a phenyl group substituted with the monocyclic group or the fused ring group.

18. The organic electroluminescence device according to claim 15 , wherein each of Ar 11 and Ar 12 of formula (5a) independently represents a phenyl group substituted with the monocyclic group or the fused ring group.

Priority Claims (1)
JP 2012-282908 · Dec 26, 2012 · national
Continuity (2)
Continuation 14140806 · Dec 26, 2013
Related Publication 20170324043A1 · Nov 9, 2017
Cited By (2)
US 12,559,674 US 12,721,037