IP Library Granted Patent US 7,571,894
Granted Patent B2
US 7,571,894 · App. 11/074,899 · Granted Aug 11, 2009

Organic electroluminescence element

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 7,571,894
App. No.
11/074,899
Granted
Aug 11, 2009
Kind
B2
Abstract

This organic electroluminescence element has an organic light-emitting layer between a positive electrode and a negative electrode, wherein the organic light-emitting layer contains a 1,3,6,8-tetrasubstituted pyrene compound having a specific structure as an organic light-emitting layer forming material. Provided are an organic light-emitting layer forming material that emits blue light with a high color purity, has a high luminous efficiency, and is stable for a long duration of operation, when used singly or as a guest, an organic EL element having a high luminous efficiency and a long operation lifetime, and a high-performance organic EL display that has a high luminous efficiency and a long operation lifetime.

Claims (31)

1. A 1,3,6,8-tetrasubstituted pyrene compound represented by the following formula (1),

in formula (1), R's have, independently from each other, a structure represented by the following formula (2),

in formula (2), R 1 -R 5 are, independently from each other, hydrogen, a straight-chain or branched-chain aliphatic group, an aromatic group, an alicyclic group, or one of the groups represented by the following formulae (3)-(6),

in formulae (3) to (6), R 6 -R 12 are, independently from each other, hydrogen, a straight-chain or branched-chain aliphatic group, an aromatic group, or an alicyclic group and

at least one of R 1 -R 5 is represented by formulae (3) and R 6 and R 7 in formula (3) are, independently from each other, an aromatic group

or

at least one of R 1 -R 5 is represented by formula (6) and R 12 in said formula (6) is an aromatic group.

2. A 1,3,6,8-tetrasubstituted pyrene compound according to claim 1 , wherein at least one of R 1 -R 5 is represented by formula (3) and R 6 and R 7 in said formula (3) are, independently from each other, an aromatic group.

3. A 1,3,6,8-tetrasubstituted pyrene compound according to claim 1 , wherein at least one of R 1 -R 5 is represented by formula (6) and R 12 in said formula (6) is an aromatic group.

4. A 1,3,6,8-tetrasubstituted pyrene compound according to claim 1 that is used as an organic light-emitting layer forming material in an organic electroluminescence element.

5. A 1,3,6,8-tetrasubstituted pyrene compound according to claim 1 that is used as an organic light-emitting layer forming material in the capacity of a host or a guest in an organic electroluminescence element.

6. An organic electroluminescence element having an organic light-emitting layer between a positive electrode and a negative electrode, wherein said organic light-emitting layer contains a 1,3,6,8-tetrasubstituted pyrene compound represented by the following formula (1) as an organic light-emitting layer forming material,

in formula (1), R's have, independently from each other, a structure represented by the following formula (2),

in formula (2), R 1 -R 5 are, independently from each other, hydrogen, a straight-chain or branched-chain aliphatic group, an aromatic group, an alicyclic group, or one of the groups represented by the following formulae (3)-(6),

in formulae (3) to (6), R 6 -R 12 are, independently from each other, hydrogen , straight-chain or branched-chain aliphatic group, an aromatic group, or an alicyclic group and

at least one of R 1 -R 5 is represented by formulae (3) and R 6 and R 7 in formula (3) are, independently from each other, an aromatic group

or

at least one of R 1 -R 5 is represented by formula (6) and R 12 in said formula (6) is an aromatic group.

7. An organic electroluminescence element according to claim 6 , wherein said 1,3,6,8-tetrasubstituted pyrene compound represented by formula (1) is an organic light-emitting layer forming material in the capacity of a host or a guest.

8. An organic electroluminescence element according to claim 6 , wherein said organic light-emitting layer is a single layer of a 1,3,6,8-tetrasubstituted pyrene compound represented by said formula (1).

9. An organic electroluminescence element according to claim 6 , wherein at least one of R 1 -R 5 is represented by formula (3) and R 6 and R 7 in said formula (3) are, independently from each other, an aromatic group.

10. An organic electroluminescence element according to claim 6 , wherein at least one of R 1 -R 5 is represented by formula (6) and R 12 in said formula (6) is an aromatic group.

11. An organic electroluminescence element according to claim 6 , wherein said organic light-emitting layer contains one or more aromatic amine compounds represented by the following formula (7),

in formula (7), Ar 1 is a di, tri or tetravalent aromatic group that may have a substituent group; R 17 and R 18 are, independently from each other, a monovalent aromatic group; and n is an integer of 2-4.

12. An organic electroluminescence element according to claim 11 , wherein the aromatic amine compound represented by formula (7) is N,N′-dinaphthyl -N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine represented by the following formula (8)

13. An organic electroluminescence element according to claim 6 , wherein said organic light-emitting layer contains one of more carbazole compounds represented by the following formula (9),

in formula (9), Ar 2 is a di, tri or tetravalent aromatic group that may have a substituent group; R 13 and R 13′ are, independently from each other, a hydrogen atom, a halogen atom, or an alkyl, aralkyl, alkenyl, aromatic, cyano, amino, acyl, alkoxycarbonyl, carboxy, alkoxy, alkylsulfonyl, hydroxyl, amide or aromatic oxy group ; and n is an integer of 2-4.

14. An organic electroluminescence element according to claim 13 , wherein the carbazole compound represented by formula (9) is 4,4′-bis(9-carbazolyl)-biphenyl represented by the following formula (10)

15. An organic electroluminescence element according to claim 6 , wherein said organic light-emitting layer contains one or more hydroxyquinoline-oxyaryl complex represented by the following formula (11),

in formula (11), R 14 is hydrogen or an alkyl group that may have a substituent group; R 15 is an aromatic group; M is a trivalent metal; and n is 1 or 2.

16. An organic electroluminescence element according to claim 15 , wherein the hydroxyquinoline-oxyaryl complex represented by formula (11) is an aluminum hydroxyquinoline-oxybiphenyl complex represented by the following formula (12)

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 1, 2012
From: FUJIFILM CORPORATION
To: UDC IRELAND LIMITED
Reel/Frame 028889/0636 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 18, 2006
From: FUJITSU LIMITED
To: FUJI PHOTO FILM CO., LTD.
Reel/Frame 018269/0287 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2005
From: SOTOYAMA, WATARU
To: FUJITSU LIMITED
Reel/Frame 016367/0362 →