IP Library › Granted Patent US 8,771,841
Granted Patent B2
US 8,771,841 · App. 12/993,051 · Granted Jul 8, 2014

Organic electroluminescent device

Inventors: Norimasa Yokoyama (Ibaraki, JP); Shigeru Kusano (Ibaraki, JP); Shuichi Hayashi (Ibaraki, JP)
Assignee: Hodogaya Chemical Co., Ltd.
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,771,841
App. No.
12/993,051
Granted
Jul 8, 2014
Kind
B2
Abstract

A problem of the invention is to provide an organic EL device having a high efficiency, a low driving voltage and a long life, by combining various materials for organic EL device, which are excellent in an injection or transportation performance of holes or electrons, and in stability and durability in a thin film, so as to enable the respective materials to effectively reveal their characteristics. The invention relates to an organic electroluminescent device including at least an anode electrode, a hole-injecting layer, a hole-transporting layer, an emitting layer, an electron-transporting layer and a cathode electrode in this order, in which the hole-injecting layer contains an arylamine compound having, in its molecule, a structure in which three or more triphenylamine structures are connected through a single bond or a hetero atom-free divalent group; and the hole-transporting layer contains an arylamine compound having two triphenylamine structures in its molecule.

Claims (140)

1. An organic electroluminescent device comprising, in this order:

an anode electrode;

a hole-injecting layer;

a hole-transporting layer;

an emitting layer;

an electron-transporting layer; and

a cathode electrode,

wherein the electron-transporting layer comprises a third compound having a pyridine ring and a pyridoindole ring in its structure and represented by formula (1):

wherein:

Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

R 1 to R 11 may be the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

B1 represents a substituted or unsubstituted aromatic hydrocarbon divalent group, a substituted or unsubstituted aromatic heterocyclic divalent group, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond;

m1 and n1 each represent an integer of from 1 to 3; and

W, X, Y, and Z each represent a carbon atom or a nitrogen atom, provided that when m1 is 2, and when m1 is 3, then n1 is 1, and only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 8 to R 11 ;

wherein the hole-injecting layer comprises a first arylamine compound represented by formula (2):

wherein:

R 12 to R 23 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic, group or a substituted or unsubstituted condensed polycyclic aromatic group, and when a plurality of these substituents are bonded on the same benzene ring, they may be bonded to each other to form a ring;

r 12 to r 23 each represent an integer of from 1 to 4; and

A 1 , A 2 , and A 3 are the same or different and each represents a divalent group represented by one of structural formulae (B) to (F):

wherein n2 represents an integer of from 1 to 3;

or

a single bond, and

wherein the hole-transporting layer comprises a second arylamine compound represented by formula (3):

wherein:

R 24 to R 29 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a linear or branched alkenyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and when a plurality of these substituents are bonded on the same benzene ring, they may be bonded to each other to form a ring;

r 24 to r 29 each represent an integer of from 1 to 4; and

A 4 represents a divalent group represented by one of structural formulae (B) to (F):

wherein n2 represents an integer of from 1 to 3;

or

a single bond.

2. The organic electroluminescent device according to claim 1 , wherein the hole-transporting layer has a film thickness of from 20 to 300 nm.

3. An organic electroluminescent device comprising, in this order:

an anode electrode;

a hole-injecting layer;

a hole-transporting layer;

an emitting layer;

an electron-transporting layer; and

a cathode electrode,

wherein the hole-injecting layer comprises a first arylamine compound having a structure in which three or more triphenylamine structures are connected through a single bond or a hetero atom-free divalent group, and

wherein the hole-transporting layer comprises a second arylamine compound having two triphenylamine structures,

wherein the electron-transporting layer comprises a third compound having a pyridine ring and a pyridoindole ring in its structure and represented by formula (1):

wherein:

Ar 1 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

R 1 to R 11 may be the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

B1 represents a substituted or unsubstituted aromatic hydrocarbon divalent group, a substituted or unsubstituted aromatic heterocyclic divalent group, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond;

m1 and n1 each represent an integer of from 1 to 3; and

W, X, Y, and Z each represent a carbon atom or a nitrogen atom, provided that when m1 is 2, and when m1 is 3, then n1 is 1, and only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 8 to R 11 .

4. The organic electroluminescent device according to claim 3 , wherein the first arylamine compound is represented by formula (2):

wherein:

R 12 to R 23 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and when a plurality of these substituents are bonded on the same benzene ring, they may be bonded to each other to form a ring;

r 12 to r 23 each represent an integer of from 1 to 4; and

A 1 , A 2 , and A 3 are the same or different and each represents a divalent group represented by one of structural formulae (B) to (F):

wherein n2 represents an integer of from 1 to 3;

a single bond.

5. The organic electroluminescent device according to claim 3 , wherein the second arylamine compound represented by formula (3):

wherein:

R 24 to R 29 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a linear or branched alkenyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and when a plurality of these substituents are bonded on the same benzene ring, they may be bonded to each other to form a ring;

r 24 to r 29 each represent an integer of from 1 to 4; and

A 4 represents a divalent group represented by one of structural formulae (B) to (F):

wherein n2 represents an integer of from 1 to 3;

or

a single bond.

6. The organic electroluminescent device according to claim 3 , wherein the third compound is represented by formula (4):

wherein:

Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

R 30 to R 44 may be the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

n3 represents an integer of from 1 to 3; and

W, X, Y, and Z each represents a carbon atom or a nitrogen atom, provided that only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 37 to R 40 .

7. The organic electroluminescent device according to claim 3 , wherein the third compound is represented by formula (5):

wherein:

Ar 3 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group;

R 45 to R 55 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

m2 and n4 each represent an integer of from 1 to 3; and

W, X, Y, and Z each represent a carbon atom or a nitrogen atom, provided that when m2 is 2, and when m2 is 3, then n4 is 1, and only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 52 to R 55 .

8. The organic electroluminescent device according to claim 1 , wherein the second arylamine compound is represented by formula (3):

wherein:

R 24 to R 29 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a linear or branched alkenyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and when a plurality of these substituents are bonded on the same benzene ring, they may be bonded to each other to form a ring;

r 24 to r 29 each represent an integer of from 1 to 4; and

A 4 represents a divalent group represented by one of structural formulae (B) to (F):

wherein n2 represents an integer of from 1 to 3;

or

a single bond.

9. The organic electroluminescent device according to claim 1 , wherein the hole-transporting layer has a film thickness of from 20 to 300 nm.

10. The organic electroluminescent device according to claim 8 , wherein the hole-transporting layer has a film thickness of from 20 to 300 nm.

11. The organic electroluminescent device according to claim 4 , wherein the second arylamine compound is represented by formula (3):

wherein:

R 24 to R 29 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a linear or branched alkenyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and when a plurality of these substituents are bonded on the same benzene ring, they may be bonded to each other to form a ring;

r 24 to r 29 each represent an integer of from 1 to 4; and

A 4 represents a divalent group represented by one of structural formulae (B) to (F):

wherein n2 represents an integer of from 1 to 3;

or

a single bond.

12. The organic electroluminescent device according to claim 4 , wherein the third compound is represented by formula (4):

wherein:

Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

R 30 to R 44 may be the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

n3 represents an integer of from 1 to 3; and

W, X, Y, and Z each represents a carbon atom or a nitrogen atom, provided that only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 37 to R 40 .

13. The organic electroluminescent device according to claim 5 , wherein the third compound is represented by formula (4):

wherein:

Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

R 30 to R 44 may be the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

n3 represents an integer of from 1 to 3; and

W, X, Y, and Z each represents a carbon atom or a nitrogen atom, provided that only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 37 to R 40 .

14. The organic electroluminescent device according to claim 11 , wherein the third compound is represented by formula (4):

wherein:

Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

R 30 to R 44 may be the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

n3 represents an integer of from 1 to 3; and

W, X, Y, and Z each represents a carbon atom or a nitrogen atom, provided that only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 37 to R 40 .

15. The organic electroluminescent device according to claim 4 , wherein the third compound is represented by formula (5):

wherein:

Ar 3 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group;

R 45 to R 55 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

m2 and n4 each represent an integer of from 1 to 3; and

W, X, Y, and Z each represent a carbon atom or a nitrogen atom, provided that when m2 is 2, and when m2 is 3, then n4 is 1, and only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 52 to R 55 .

16. The organic electroluminescent device according to claim 5 , wherein the third compound is represented by formula (5):

wherein:

Ar 3 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group;

R 45 to R 55 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

m2 and n4 each represent an integer of from 1 to 3; and

W, X, Y, and Z each represent a carbon atom or a nitrogen atom, provided that when m2 is 2, and when m2 is 3, then n4 is 1, and only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 52 to R 55 .

17. The organic electroluminescent device according to claim 11 , wherein the third compound is represented by formula (5):

wherein:

Ar 3 represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group or a substituted or unsubstituted condensed polycyclic aromatic group;

R 45 to R 55 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group;

m2 and n4 each represent an integer of from 1 to 3; and

W, X, Y, and Z each represent a carbon atom or a nitrogen atom, provided that when m2 is 2, and when m2 is 3, then n4 is 1, and only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom is not substituted with any of R 52 to R 55 .

18. The organic electroluminescent device according to claim 1 , wherein the first arylamine compound is Compound 2-1:

19. The organic electroluminescent device according to claim 1 , wherein the second arylamine compound is Compound 3-1:

20. The organic electroluminescent device according to claim 1 , wherein the third compound is Compound 1-10:

21. The organic electroluminescent device according to claim 1 , wherein the first arylamine compound is Compound 2-1:

and the second arylamine compound is Compound 3-1:

22. The organic electroluminescent device according to claim 1 , wherein the first arylamine compound is Compound 2-1:

and the third compound is Compound 1-10:

23. The organic electroluminescent device according to claim 1 , wherein the second arylamine compound is Compound 3-1:

and the third compound is Compound 1-10:

24. The organic electroluminescent device according to claim 1 , wherein the first arylamine compound is Compound 2-1:

the second arylamine compound is Compound 3-1:

and the third compound is Compound 1-10:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 23, 2010
From: YOKOYAMA, NORIMASA; KUSANO, SHIGERU; HAYASHI, SHUICHI
To: HODOGAYA CHEMICAL CO., LTD.
Reel/Frame 025396/0701 →
Priority Claims (2)
JP 2008-129340 · May 16, 2008 · national
JP 2008-173023 · Jul 2, 2008 · national
Continuity (1)
Related Publication 20110073852A1 · Mar 31, 2011