Fluorescent organic light emitting elements having high efficiency

Patent metadata

Field	Value
Publication number	US-10074805-B2
Application number	US-201515500853-A
Country	US
Kind code	B2
Filing date	Sep 16, 2015
Priority date	Sep 22, 2014
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The present invention relates to organic light emitting elements, comprising thermally activated delayed fluorescence (TADF) emitters and/or hosts on basis of phthalimide and naphthalimide materials, which have a sufficiently small energy gap between S 1 and T 1 (ΔE ST ) to enable up-conversion of the triplet exciton from T 1 to S 1 . The organic light emitting elements show high electroluminescent efficiency.

First claim

The invention claimed is:

1. A compound of formula

wherein
X is O, or NR 2 ;
R 1 is a C 1 -C 25 alkyl group, a C 6 -C 10 aryl group which is optionally substituted by one or more groups R 8 ;
R 2 is a C 1 -C 6 alkyl group, a C 2 -C 4 alkenyl group, or a C 6 -C 10 aryl group, which is optionally substituted by one or more groups R 8 ; or
R 1 and R 2 together form a ring

wherein
R 37 , R 38 , R 39 and R 40 are independently of each other H, D, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 10 aryl group which may optionally be substituted by one or more groups R 8 ,
A 1 , A 2 and A 3 are C,
x is 0, or 1,
if x is 0,
A 1 and A 3 are connected via a double bond and together form a ring

if x is 1, then X is NR 2 ,
A 1 and A 2 and A 2 and A 3 are connected via a single bond and together form a ring system

R 3 , R 4 , R 5 , R 6 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 are independently of each other H, D, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 10 aryl group which may optionally be substituted by one or more groups R 8 , or a donor group of formula

R 8 is D, F, Cl, a C 1 -C 12 alkyl group, a C 1 -C 12 alkoxy group, or a C 6 -C 10 aryl group;
X 1 is a direct bond, O, S, N(R 15 ), C(═O), C(R 16 )(R 17 ), B(R 18 ), or Si(R 19 )(R 20 ),
R 10 , R 11 , R 21 and R 21′ are independently of each other H, D, F, Cl, Br, or a C 1 -C 25 alkyl group;
R 15 , R 16 , R 17 , R 18 , R 19 and R 20 are independently of each other H, D, a C 1 -C 25 alkyl group, or a C 6 -C 14 aryl group, which can optionally be substituted by one, or more groups selected from a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group and a C 6 -C 10 aryloxy group;
with the proviso that at least one of the groups R 3 , R 4 , R 5 , R 6 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 is a donor group of formula (Xa), or (Xd).

2. The compound according to claim 1 , which is a compound of formula

wherein X, R 1 , R 3 , R 4 , R 5 and R 6 are as defined in claim 1 .

3. The compound according to claim 2 , which is a compound of formula

wherein R 1 , R 3 , R 4 , R 5 and R 6 are as defined in claim 1 .

4. The compound according to claim 1 , wherein
R 3 , R 4 , R 5 and R 6 are independently of each other a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 3 and R 6 are H and R 4 and R 5 are independently of each other a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 4 and R 5 are H and R 3 and R 6 are independently of each other a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 4 and R 6 are H and R 3 and R 5 are independently of each other a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 3 , R 4 and R 6 are H and R 5 is a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 3 , R 4 and R 5 are H and R 6 is a donor group of formula (Xa), or (Xd) as defined in claim 1 .

5. The compound according to claim 2 , which is a compound of formula

wherein R 3 , R 4 , R 5 and R 6 are as defined in claim 1 .

6. The compound according to claim 5 , wherein
R 3 , R 4 , R 5 and R 6 are independently of each other a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 3 and R 6 are H and R 4 and R 5 are independently of each other a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 4 and R 5 are H and R 3 and R 6 are independently of each other a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 3 , R 4 and R 5 are H and R 6 is a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 3 , R 4 and R 6 are H and R 5 is a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 3 , R 5 and R 6 are H and R 4 is a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 4 , R 5 and R 6 are H and R 3 is a donor group of formula (Xa), or (Xd) as defined in claim 1 .

7. The compound according to claim 1 , which is a compound of formula

wherein X, R 1 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 are as defined in claim 1 .

8. The compound according to claim 7 , which is a compound of formula

wherein R 31 , R 32 , R 33 , R 34 , R 35 and R 36 are as defined in claim 1 .

9. The compound according to claim 8 , wherein
R 31 , R 32 , R 33 , R 35 and R 36 are H and R 34 is a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 31 , R 32 , R 34 , R 35 and R 36 are H and R 33 is a donor group of formula (Xa), or (Xd) as defined in claim 1 ; or
R 31 , R 32 , R 35 and R 36 are H and R 33 and R 34 are independently of each other a donor group of formula (Xa), or (Xd) as defined in claim 1 .

10. The compound according to claim 1 , wherein R 1 is a C 1 -C 25 alkyl group, a group of formula

wherein
R 41 and R 42 are a C 1 -C 8 alkyl group;
R 43 is a C 1 -C 8 alkyl group, or a C 1 -C 8 alkoxy group;
R 44 is a C 1 -C 8 alkyl group, or a phenyl group; and
R 45 is a C 1 -C 8 alkyl group.

11. The compound according claim 1 , wherein the donor group is a donor group of formula (Xa), wherein X 1 is a direct bond, O, S, C(CH 3 )(CH 3 ), C(═O), or

and R 10 and R 11 are as defined in claim 1 ; or a donor group of formula (Xd), wherein R 21 and R 21′ are H.

12. The compound according to claim 1 , wherein the donor group is a group of formula

13. A light-emitting layer comprising the compound according claim 1 .

14. An organic light emitting element, comprising the compound according to claim 1 .

15. The organic light-emitting element according to claim 14 , comprising a light-emitting layer comprising a compound according to claim 1 as guest and a host material.

16. The organic light-emitting element according to claim 14 , comprising a light-emitting layer comprising a compound according to claim 1 as host and a guest material.

17. The organic light-emitting element according to claim 14 , characterized in that it emits delayed fluorescence.

18. A device selected from the group consisting of a electrophotographic photoreceptor, pho

Assignees

• Udc Ireland Ltd

Inventors

• Tanabe Junichi
• Benedito Flavio Luiz
• Lennartz Christian

Classifications

• H01L51/5016

  Electricity · mapped topic

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C07D401/04

  directly linked by a ring-member-to-ring-member bond · CPC title