Organic electric-field light-emitting element, light-emitting material for organic electric-field light-emitting element, and light-emitting device, display device, and illumination device using same element

Patent metadata

Field	Value
Publication number	US-9954190-B2
Application number	US-201214124945-A
Country	US
Kind code	B2
Filing date	Jun 5, 2012
Priority date	Jun 16, 2011
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

An organic electroluminescent element that uses a compound expressed by the following general formula emits dark blue light and exhibits little change in chromaticity during brightness modulation. (n1 is an integer from 0 to 8; the R 1 [groups] are each independently a substituent substituted for a hydrogen atom of the pyrene skeleton; X is CR a R b (R a and R b are each independently a hydrogen atom or a substituent), O, S, or SiR d R e (R d and R e are each independently a hydrogen atom or a substituent); and A 1 to A 4 represent each independently either N or CR f (R f represents a hydrogen atom or a substituent, and two adjacent R f [groups] may jointly form a saturated or unsaturated ring, but no more than two rings may be formed jointly by two or more of the R f [groups]).)

First claim

The invention claimed is:

1. An organic electroluminescent element having
a substrate,
a pair of electrodes disposed on this substrate and including an anode and a cathode, and a single or a plurality of organic layers disposed between these electrodes, wherein
said organic layer(s) include a light-emitting layer, and this light-emitting layer contains a host material and at least one light-emitting material expressed by General Formula 1 below:

n1 represents an integer from 0 to 8; the R 1 groups each independently represents a substituent substituted for a hydrogen atom of the pyrene skeleton, with the proviso that if n1 is 2 or greater, adjacent R 1 groups are not linked to each other to form a saturated or unsaturated ring; X represents CR a R b , wherein R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b may jointly form a five- or six-membered ring, NR c , wherein R c represents a hydrogen atom or a substituent, O, S, or SiR d R e , wherein R d and R e each independently represents a hydrogen atom or a substituent, and R d and R e may jointly form a five- or six-membered ring; and A 1 to A 4 each independently represents either N or CR f , wherein R f represents a hydrogen atom or a substituent, and two adjacent R f groups may jointly form a saturated or unsaturated ring, but no more than two rings may be formed jointly by two or more of the R f groups.

2. The organic electroluminescent element according to claim 1 , wherein R a , R b , R d , and R e each independently represent an alkyl group, an aryl group, or a heteroaryl group in General Formula 1 above.

3. The organic electroluminescent element according to claim 1 , wherein R c represents a substituent in General Formula 1 above.

4. The organic electroluminescent element according to claim 1 wherein X represents CR a′ R b′ , wherein R a′ and R b′ each independently represents an alkyl group, an aryl group, or a heteroaryl group, and R a′ and R b′ may jointly form a five- or six-membered ring or wherein represents a substituent in General Formula 1 above.

5. The organic electroluminescent element according to claim 1 wherein R 1 has at least one N,N-diarylamino group or an aryl group substituted with an N,N-diarylamino group in General Formula 1 above.

6. The organic electroluminescent element according to claim 1 wherein the light-emitting material expressed by General Formula 1 above is expressed by General Formula 2 below:

R 2 to R 7 each independently represent a hydrogen atom or a substituent, with the proviso that adjacent R 2 to R 7 groups are not linked to each other to form a saturated or unsaturated ring; X represents CR a R b , wherein R a and R b each independently represent a hydrogen atom or a substituent, and R a and R b may jointly form a five- or six-membered ring, NR c , wherein R c represents a hydrogen atom or a substituent, O, S, or SiR d R e , wherein R d and R e each independently represents a hydrogen atom or a substituent, and R d and R e may jointly form a five- or six-membered ring; and A 1 to A 4 each independently represents either N or CR f , wherein R f represents a hydrogen atom or a substituent, and two adjacent R f groups may jointly form a saturated or unsaturated ring, but no more than two rings may be formed jointly by two or more of the R f groups.

7. The organic electroluminescent element according to claim 1 wherein the light-emitting material expressed by General Formula 1 above is expressed by General Formula 3 below:

R 2 to R 7 each independently represents a hydrogen atom or a substituent, with the proviso that adjacent R 2 to R 7 groups are not linked to each other to form a saturated or unsaturated ring;
X represents CR a R b , wherein R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b may jointly form a five- or six-membered ring, NR c , wherein R c represents a hydrogen atom or a substituent, O, S, or SiR d R e , wherein R d and R e each independently represents a hydrogen atom or a substituent, and R d and R e may jointly form a five- or six-membered ring; and
R 8 to R 11 each independently represents a hydrogen atom or a substituent, and adjacent two of the R 8 to R 11 groups may jointly form a saturated or unsaturated ring, but no more than two rings may be formed jointly by two or more of the R 8 to R 11 groups.

8. The organic electroluminescent element according to claim 1 wherein the light-emitting material expressed by General Formula 1 above is expressed by General Formula 4 below:

R 2 to R 7 each independently represents a hydrogen atom or a substituent, with the proviso that adjacent R 2 to R 7 groups are not linked to each other to form a saturated or unsaturated ring;
R 8 to R 11 each independently represents a hydrogen atom or a substituent, and adjacent two of the R 8 to R 11 groups may jointly form a saturated or unsaturated ring, but no more than two rings may be formed jointly by two or more of the R 8 to R 11 groups; and
R 12 and R 13 each independently represents a hydrogen atom or a substituent, and R 12 and R 13 may jointly form a five- or six-membered ring.

9. The organic electroluminescent element according to claim 8 , wherein at least one of R 2 to R 11 represents a substituent in General Formula 4 above.

10. The organic electroluminescent element according to claim 8 , wherein R 5 and/or R 10 represents a substituent in General Formula 4 above.

11. The organic electroluminescent element according to claim 1 wherein said host material contained in said light-emitting layer has a hydrocarbon condensed ring structure with a carbon number of 10 to 50.

12. The organic electroluminescent element according to claim 1 wherein said light-emitting layer is formed by a vacuum vapor deposition process.

13. The organic electroluminescent element according to claim 1 wherein said light-emitting layer is formed by a wet process.

14. A light-emitting device comprising the organic electroluminescent element according to claim 1 .

15. A display device comprising the organic electroluminescent element according to claim 1 .

16. An illumination device comprising the organic electroluminescent element according to claim 1 .

17. A light-emitting material for an organic electroluminescent element expressed by General Formula 1 below:

n1 represents an integer from 0 to 8; the R 1 groups each independently represents a substituent substituted for a hydrogen atom of the pyrene skeleton; however, if n1 is 2 or greater, a case is excluded in which adjacent R 1 groups are linked to each other to form a saturated or unsaturated ring; X represents CR a R b , wherein R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b may jointly form a five- or six-membered ring, NR c , wherein R c represents a hydrogen atom or a substituent, O, S, or SiR d R e ; R d and R e each independently a hydrogen atom

Assignees

• Takada Saki
• Yonekuta Yasunori
• Ise Toshihiro
• Kitamura Tetsu
• Watanabe Toru
• Sotoyama Wataru
• Takaku Koji
• Youfu Katsuyuki
• Udc Ireland Ltd

Inventors

• Takada Saki
• Yonekuta Yasunori
• Ise Toshihiro
• Kitamura Tetsu
• Watanabe Toru
• Sotoyama Wataru
• Takaku Koji
• Youfu Katsuyuki

Classifications

• C07F7/0809

  Chemistry & Metallurgy · mapped topic

• H01L51/5012

  Electricity · mapped topic

• H01J29/20

  characterised by the luminescent material · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• H01L51/006

  Electricity · mapped topic