Organic electroluminescence element

Patent metadata

Field	Value
Publication number	US-9608207-B2
Application number	US-201214110630-A
Country	US
Kind code	B2
Filing date	Apr 11, 2012
Priority date	Apr 12, 2011
Publication date	Mar 28, 2017
Grant date	Mar 28, 2017

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.).

First claim

The invention claimed is:

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:

Assignees

• Takaku Koji
• Kitamura Tetsu
• Watanabe Toru
• Yonekuta Yasunori
• Udc Ireland Ltd

Inventors

• Takaku Koji
• Kitamura Tetsu
• Watanabe Toru
• Yonekuta Yasunori

Classifications

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• C07C13/62 Primary

  with more than three condensed rings · CPC title

• C07D487/06

  Peri-condensed systems · CPC title

• C07F7/0807

  comprising Si as a ring atom · CPC title

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title