IP Library › Granted Patent US 9,608,207
Granted Patent B2
US 9,608,207 · App. 14/110,630 · Granted Mar 28, 2017

Organic electroluminescence element

Inventors: Koji Takaku (Kanagawa, JP); Tetsu Kitamura (Kanagawa, JP); Toru Watanabe (Kanagawa, JP); Yasunori Yonekuta (Kanagawa, JP)
Assignee: UDC Ireland Limited
H01L51/0067C07B59/001C07C13/62C07C25/22C07C33/26C07C211/61C07D213/74C07D239/22C07D295/04C07D307/77C07D333/50C07D333/78C07D487/06C07D493/06C07D495/06C07F7/0807C09B1/00C09B57/00C09B57/001C09K11/06H01L51/006H01L51/0056H01L51/0058H01L51/0061H01L51/0071H01L51/0072H01L51/0073H01L51/0074H01L51/0094H01L51/50C07B2200/05C07C2103/54C09K2211/1011C09K2211/1022C09K2211/1033C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096H01L51/5012
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Quick Facts
Patent No.
US 9,608,207
App. No.
14/110,630
Granted
Mar 28, 2017
Kind
B2
Abstract

An organic electroluminescence element that uses a compound expressed by the following general formula has low inter-molecular interaction and high orientation during vapor deposition, and by using compounds that are resistant to aggregation, luminous efficiency is high, and there is little change in chromaticity accompanying drive deterioration (either V 1 or W 1 and either V 2 or W 2 form rings, the rings formed by V 1 and V 2 are six-membered rings, and the rings formed by W 1 and W 2 are five-membered rings; A 2 to A 4 and A 6 to A 8 represent CR Z or N, and R Z represents a hydrogen atom or a substituent; and R 2 , R 3 , R 7 , and R 8 represent a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom [sic], or a deuterium atom.).

Claims (63)

1. An organic electroluminescence element having

a substrate,

a pair of electrodes that is disposed on this substrate and that includes an anode and a cathode, and

an organic layer disposed between these electrodes, wherein

said organic layer contains a compound expressed by General Formula 1 below:

either V 1 or W 1 forms a ring, either V 2 or W 2 also forms a ring, the ring formed by V 1 and V 2 is a six-membered ring, and the ring formed by W 1 and W 2 is a five-membered ring,

wherein when both V 1 and V 2 form a six-membered ring, at least one of V 1 and V 2 has a linking group E that links the portion represented by a dotted line in General Formula 1, wherein E is CR x R y , SiR a R b , or O;

each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group;

each of R a and R b independently represents an alkyl group or an aryl group;

each of A 2 to A 4 and A 6 to A 8 independently represents CR Z or N, wherein two adjacent CR Z groups may together form a five- or six-membered ring, and

R Z represents a hydrogen atom or a substituent; and

each of R 2 , R 3 , R 7 , and R 8 independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom.

2. The organic electroluminescence element according to claim 1 , wherein the compound expressed by General Formula 1 above is expressed by General Formula 2 below:

wherein A 1 to A 8 represent CR Z or N, and R Z represents a hydrogen atom or a substituent; E represents CR x R y , SiR a R b , or O; each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group; each of R a and R b independently represents an alkyl group or an aryl group; and each of R 2 to R 4 and R 7 to R 9 independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom.

3. The organic electroluminescence element according to claim 1 , wherein the compound expressed by General Formula 1 above is expressed by General Formula 3 below:

wherein A 1 to A 8 represent CR Z or N, and R Z represents a hydrogen atom or a substituent; G represents CR x R y , SiR a R b , NR c , S, or O; each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group; R a , R b , and R c represent each independently an alkyl group or an aryl group; and each of R 1 to R 3 and R 6 to R 8 independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom.

4. The organic electroluminescence element according to claim 2 , wherein the compound expressed by General Formula 2 above is expressed by General Formula 4 below:

wherein E represents CR x R y , SiR a R b , or O; each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group; R a and R b represent each independently represents an alkyl group or an aryl group; each of R 2 to R 4 and R 7 to R 9 independently an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom; each of R 11 to R 18 independently represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an arylthio group, a fluorine atom, a hydrogen atom, a deuterium atom, a cyano group, or an amino group; and each pair of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 may bond to each other to form a ring.

5. The organic electroluminescence element according to claim 4 , wherein in General Formula 4 above, one of R 12 to R 14 and R 16 to R 18 is NR 19 R 20 , wherein each of R 19 and R 20 independently represents an alkyl group or an aryl group, and these may bond to each other to form a ring.

6. The organic electroluminescence element according to claim 3 , wherein the compound expressed by General Formula 3 above is expressed by General Formula 5 below:

wherein G represents CR x R y , SiR a R b , NR c , S, or O; each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group; each of R a , R b , and R c represent each independently represents an alkyl group or an aryl group; each of R 1 to R 3 and R 6 to R 8 independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom; each of R 11 to R 18 independently represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an arylthio group, a fluorine atom, a hydrogen atom, a deuterium atom, a cyano group, or an amino group; and each pair of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 may bond to each other to form a ring.

7. The organic electroluminescence element according to claim 6 , wherein in General Formula 5 above, one of R 11 to R 13 and R 16 to R 18 is NR 19 R 20 , wherein each of R 19 and R 20 independently represents an alkyl group or an aryl group, and these may bond to each other to form a ring.

8. The organic electroluminescence element according to claim 6 , wherein in General Formula 5 above, G is CR x R y , S, or O, wherein each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group.

9. The organic electroluminescence element according to claim 4 , wherein the compound expressed by General Formula 4 above is expressed by General Formula 6 below:

wherein X and Y represent each independently an alkyl group, an aryl group, or a silyl group; each of R 2 to R 4 and R 7 to R 9 independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom; each of R 11 to R 18 independently represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an arylthio group, a fluorine atom, a hydrogen atom, a deuterium atom, a cyano group, or an amino group; and each pair of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 may bond to each other to form a ring.

10. The organic electroluminescence element according to claim 9 , wherein in General Formula 6 above, one of R 12 to R 14 and R 16 to R 18 is NR 19 R 20 , wherein each of R 19 and R 20 independently represents an alkyl group or an aryl group, and these may bond to each other to form a ring.

11. The organic electroluminescence element according to claim 9 , wherein in General Formula 6 above, R 13 and/or R 17 is NR 19 R 20 , wherein each of R 19 and R 20 independently represents an alkyl group or an aryl group, and these may bond to each other to form a ring.

12. The organic electroluminescence element according to claim 6 , wherein the compound expressed by General Formula 5 above is expressed by General Formula 7 below:

wherein X and Y represent each independently an alkyl group, an aryl group, or a silyl group; R 1 to R 3 and R 6 to R 8 represent each independently an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom; R 11 to R 18 independently represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an arylthio group, a fluorine atom, a hydrogen atom, a deuterium atom, a cyano group, or an amino group; and each pair of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 may bond to each other to form a ring.

13. The organic electroluminescence element according to claim 12 , wherein in General Formula 7 above, one of R 11 to R 13 and R 16 to R 18 is NR 19 R 20 , wherein each of R 19 and R 20 independently represents an alkyl group or an aryl group, and these may bond to each other to form a ring.

14. The organic electroluminescence element according to claim 12 , wherein in General Formula 7 above, R 12 and/or R 17 is NR 19 R 20 , wherein each of R 19 and R 20 independently represents an alkyl group or an aryl group, and these may bond to each other to form a ring.

15. The organic electroluminescence element according to claim 1 , wherein the compound expressed by General Formula 1 above includes in its molecule a group containing an alkyl group, a silyl group, or a fluorine atom.

16. The organic electroluminescence element according to claim 1 , wherein the molecular weight of the compound expressed by General Formula 1 above is 1000 or less.

17. The organic electroluminescence element according to claim 1 , wherein at least one organic layer that contains the compound expressed by General Formula 1 above is a light-emitting layer.

18. The organic electroluminescence element according to claim 17 , wherein the compound expressed by General Formula 1 above is a light-emitting material.

19. The organic electroluminescence element according to claim 17 , wherein said light-emitting layer includes an anthracene-based host material.

20. The organic electroluminescence element according to claim 19 , wherein said anthracene-based host material is expressed by General Formula An-1 below:

wherein Ar 1 and Ar 2 represent each independently an aryl group or a heteroaryl group; each of R 301 to R 308 independently represents a hydrogen atom or a substituent; and R 301 and R 302 , R 302 and R 303 , R 303 and R 304 , R 305 and R 306 , R 306 and R 307 , and R 307 and R 308 may bond to each other to form a ring.

21. The organic electroluminescence element according to claim 20 , wherein the compound expressed by General Formula An-1 above is a compound expressed by General Formula An-2 below:

wherein each of R 301 to R 318 independently represents a hydrogen atom or a substituent; and each pair of R 301 and R 302 , R 302 and R 303 , R 303 and R 304 , R 305 and R 306 , R 306 and R 307 , R 307 and R 308 , R 309 and R 310 , R 310 and R 311 , R 311 and R 312 , R 312 and R 313 , R 314 and R 315 , R 315 and R 316 , R 316 and R 317 , and R 317 , and R 318 may bond to each other to form a ring.

22. The organic electroluminescence element according to claim 17 , wherein said light-emitting layer is formed by a vacuum vapor deposition process.

23. The organic electroluminescence element according to claim 17 , wherein said light-emitting layer is formed by a wet process.

24. A light-emitting device, display device, or illumination device which makes use of the organic electroluminescence element according to claim 1 .

25. A material for an organic electroluminescence element expressed by General Formula 1 below:

wherein either V 1 or W 1 forms a ring, either V 2 or W 2 also forms a ring, the ring formed by V 1 and V 2 is a six-membered ring, and the ring formed by W 1 and W 2 is a five-membered ring, wherein when both V 1 and V 2 form a six-membered ring, at least one of V 1 and V 2 has a linking group E that links the portion represented by a dotted line in General Formula 1, wherein E is CR x R y , SiR a R b , or O;

each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group;

each of R a and R b independently represents an alkyl group or an aryl group;

each of A 2 to A 4 and A 6 to A 8 independently represents CR Z or N, wherein two adjacent CR Z groups may together form a five- or six-membered ring, and R Z represents a hydrogen atom or a substituent; and

R 2 , R 3 , R 7 , and R 8 independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom.

26. The material for an organic electroluminescence element according to claim 25 , wherein the material is expressed by General Formula 2 below:

wherein A 1 to A 8 represent CR Z or N, and R Z represents a hydrogen atom or a substituent; E represents CR x R y , SiR a R b , or O; each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group; each of R a and R b independently represents an alkyl group or an aryl group; and each of R 2 to R 4 and R 7 to R 9 independently represents, an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom.

27. The material for an organic electroluminescence element according to claim 25 , wherein the material is expressed by General Formula 3 below:

wherein A 1 to A 8 represent CR Z or N, and R Z represents a hydrogen atom or a substituent; G represents CR x R y , SiR a R b , NR c , S, or O; each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group; R a , R b , and R c represent each independently an alkyl group or an aryl group; and each of R 1 to R 3 and R 6 to R 8 independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom.

28. The material for an organic electroluminescence element according to claim 25 , wherein the material is expressed by General Formula 6 below:

wherein each of X and Y independently represents an alkyl group, an aryl group, or a silyl group; each of R 2 to R 4 and R 7 to R 9 independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom; each of R 11 to R 18 independently represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an arylthio group, a fluorine atom, a hydrogen atom, a deuterium atom, a cyano group, or an amino group; and each pair of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 may bond to each other to form a ring.

29. The material for an organic electroluminescence element according to claim 25 , wherein the material is expressed by General Formula 7 below:

wherein each of X and Y independently represents an alkyl group, an aryl group, or a silyl group; R 1 to R 3 and R 6 to R 8 represent each independently an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom; each of R 11 to R 18 independently represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, a heteroaryl group, an arylthio group, a fluorine atom, a hydrogen atom, a deuterium atom, a cyano group, or an amino group; and each pair of R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 may bond to each other to form a ring.

30. A compound expressed by General Formula 1 below:

wherein either V 1 or W 1 forms a ring, either V 2 or W 2 also forms a ring, the ring formed by V 1 and V 2 is a six-membered ring, and the ring formed by W 1 and W 2 is a five-membered ring, wherein when both V 1 and V 2 form a six-membered ring, at least one of V 1 and V 2 has a linking group E that links the portion represented by a dotted line in General Formula 1, wherein E is CR x R y , SiR a R b , or O;

each of R x and R y independently represents an alkyl group, an aryl group, or a silyl group;

each of R a and R b independently represents an alkyl group or an aryl group;

A 2 to A 4 and A 6 to A 8 represent each independently CR Z or N, wherein two adjacent CR Z groups may together form a five- or six-membered ring, and R Z represents a hydrogen atom or a substituent; and

R 2 , R 3 , R 7 , and R 8 independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a hydrogen atom, or a deuterium atom.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2014
From: TAKAKU, KOJI; KITAMURA, TETSU; WATANABE, TORU; YONEKUTA, YASUNORI
To: UDC IRELAND LIMITED
Reel/Frame 032147/0255 →
Priority Claims (2)
JP 2011-087857 · Apr 12, 2011 · national
JP 2012-089049 · Apr 10, 2012 · national
Continuity (1)
Related Publication 20140299851A1 · Oct 9, 2014