Fluorescent organic light emitting elements having high efficiency
An organic light-emitting element which emits delayed fluorescence comprising specifically substituted 1,2,4-triazole derivatives, 1,2,4-oxadiazole derivatives or 1,2,4-thiadiazole derivatives in the light-emitting layer, a light-emitting layer comprising the specifically substituted 1,2,4-triazole derivatives, 1,2,4-oxadiazole derivatives or 1,2,4-thiadiazole derivatives, specific specifically substituted 1,2,4-triazole derivatives, 1,2,4-oxadiazole derivatives and 1,2,4-thiadiazole derivatives and an organic light emitting element comprising the specific 1,2,4-azole derivatives as well as a light emitting layer comprising the specific 1,2,4-azole derivatives; the use of the specifically substituted 1,2,4-triazole derivatives, 1,2,4-oxadiazole derivatives and 1,2,4-thiadiazole derivatives for electrophotographic photoreceptors, photoelectric converters, sensors, dye lasers, solar cell devices and organic light emitting elements, and the use of the specifically substituted 1,2,4-triazole derivatives, 1,2,4-oxadiazole derivatives and 1,2,4-thiadiazole derivatives for generating delayed fluorescence emission.
1. A compound of formula
wherein
X is N—Y 4 —R 4 ,
Y 1 and Y 2 and Y 4 are independently of each other a direct bond, C 1 -C 25 -alkylene, or C 6 -C 10 -arylene, which is unsubstituted or substituted by one or more groups R 3 ;
R 1 and R 2 are independently of each other deuterium, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, which is unsubstituted or substituted by one or more groups R 3 , a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
R 3 is deuterium, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, or a C 6 -C 14 aryl group;
R 4 is a C 1 -C 25 alkyl group, a C 6 -C 10 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
X 1 is 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 hydrogen, deuterium, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, which is unsubstituted or substituted by one or more groups R 3 , or a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3;
R 15 , R 16 , R 17 , R 18 , R 19 , and R 20 are independently of each other a C 1 -C 25 alkyl group, or a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3 ;
wherein at least one group of formula (Xa), or (Xd) is present in the compound of formula (I).
2. The compound according to claim 1 , wherein Y 1 and Y 2 and Y 4 are independently of each other a direct bond, or a group of formula
3. The compound according to claim 1 , wherein
R 1 and R 2 are independently of each other a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 10 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
R 3 is a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 10 aryloxy group, or a C 6 -C 14 aryl group;
R 4 is a C 1 -C 25 alkyl group, a C 6 -C 10 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
X 1 is O, S, C(O), N(R 15 ), or C(R 16 )(R 17 ); and
R 10 , R 11 , R 21 and R 21′ are independently of each other hydrogen, or a C-C 25 alkyl group;
R 15 is a group of formula
R 16 and R 17 are independently of each other hydrogen, or a C 1 -C 25 alkyl group;
R 22 and R 23 are independently of each other hydrogen, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 10 aryloxy group, or a C 6 -C 10 aryl group;
wherein at least one group of formula (Xa), or (Xd) is present in the compound of formula (I).
4. The compound according to claim 1 , wherein the group of formula (Xa) or (Xd) is a group of formula (Xa), wherein X 1 is O, S, C(CH 3 )(CH 3 ), C(═O),
or a group of formula (Xd), wherein R 21 and R 21′ are hydrogen.
5. The compound according to claim 1 , wherein the group of formula (Xa) or (Xd) is a group of formula
6. The compound according to claim 1 , wherein
R 1 and R 2 are independently of each other a C 6 -C 10 aryl group, or a group of formula (Xa) or (Xd);
R 4 is a C 1 -C 25 alkyl group, a C 6 -C 10 aryl group, or a group of formula (Xa) or (Xd);
X 1 is O, S, C(CH 3 )(CH 3 ), C(═O), or
and
R 10 , R 11 , R 21 and R 21 ′ are independently of each other hydrogen, or a C 1 -C 25 alkyl group;
wherein at least one group of formula (Xa), or (Xd) is present in the compound of formula (I).
7. A light-emitting layer comprising at least one compound of formula (I) as described in claim 1 as guest and a host material; or comprising at least one compound of formula (I) as described claim 1 as host and a fluorescent guest material.
8. A compound of formula
wherein
X is N—Y 4′ —R 4 or N—Y 4″ —R 4 ,
Y l and Y 2 are independently of each other a direct bond, C 1 -C 25 -alkylene, or C 6 -C 10 -arylene, which is unsubstituted or substituted by one or more groups R 3 ;
Y 4′ is a direct bond, C 1 -C 25 -alkylene;
Y 4″ is C 6 -C 10 -arylene, which is unsubstituted or substituted by one or more groups R 3 ;
R 1 and R 2 are independently of each other deuterium, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, which is unsubstituted or substituted by one or more groups R 3 , a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
R 3 is deuterium, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, or a C 6 -C 14 aryl group;
R 4 is a C 1 -C 25 alkyl group, a C 6 -C 10 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
X 1 is O, S, N(R 15 ), C(═O), C(R 16 )(R 17 ), B(R 18 ), or Si(R 19 )(R 20 ), or
when X is N—Y 4″ —R 4 ,
X 1 is 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 hydrogen, deuterium, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, which is unsubstituted or substituted by one or more groups R 3 , or a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3 ;
R 15 , R 16 , R 17 , R 18 , R 19 , R 20 are independently of each other a C 1 -C 25 alkyl group, or a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3 ;
R 15′ is a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3 ,
wherein at least one group of formula (Xa) or (Xd) is present in the compound of formula (I′).
9. The compound according to claim 8 , wherein Y 1 and Y 2 are independently of each other a direct bond, or a group of formula
and
Y 4 is selected from a direct bond; and or
Y 4″ is a group of formula
10. The compound according to claim 8 , wherein
R 1 and R 2 are independently of each other a C 1 -C 25 alkyl group, a C 1 C 25 alkoxy group, a C 6 -C 10 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
R 3 is a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, or a C 6 -C 14 aryl group;
R 4 is a C 1 -C 25 alkyl group, a C 6 -C 10 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
X 1 is O , S, C(O), N(R 15 ), or C(R 16 )(R 17 ); or
when X is N—Y 4″ —R 4 ,
X 1 is N(R 15′ ) or C(R 16 )(R 17 ), and
R 10 , R 11 , R 21 and R 21 ′ are independently of each other hydrogen, or a C 1 -C 25 alkyl group;
R 15 and R 15′ are independently of each other a group of formula
R 16 and R 17 are independently of each other hydrogen, or a C 1 -C 25 alkyl group;
R 22 and R 23 are independently of each other hydrogen, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 10 aryloxy group, or a C 6 -C 10 aryl group;
wherein at least one group of formula (Xa), or (Xd) is present in the compound of formula (I′).
11. The compound according to claim 8 , wherein the group of formula (Xa) or (Xd) is a group of formula (Xa), wherein
X 1 is O, S, C(CH 3 )(CH 3 ), C(═O),
or
when X is N—Y 4″ —R 4 ,
X 1 is C(CH 3 )(CH 3 ), C(═O),
or a group of formula (Xd), wherein R 21 and R 21′ are hydrogen.
12. The compound according to claim 8 , wherein the group of formula (Xa) or (Xd) is a group of formula
or
when X is N—Y 4″ —R 4 , a group of formula
13. The compound according to claim 8 , wherein
R 1 and R 2 are independently of each other a C 6 -C 10 aryl group, or a group of formula (Xa) or (Xd);
R 4′ is a C 1 -C 25 alkyl group, a C 6 -C 10 aryl group, or a group of formula (Xa) or (Xd);
X 1 is O, S, C(CH 3 )(CH 3 ), C(═O), or
or
when X is N—Y 4″ —R 4 ,
X 1 is C(CH 3 )(CH 3 ), C(═O),
and
R 10 , R 11 , R 21 and R 21′ are independently of each other hydrogen, or a C 1 -C 25 alkyl group;
wherein at least one group of formula (Xa), or (Xd) is present in the compound of formula (I′).
14. A light-emitting layer comprising the compound according to claim 8 .
15. An organic light emitting element, comprising the compound according to claim 8 .
16. The organic light-emitting element according to claim 15 , characterized in that it emits light by delayed fluorescence.
17. A device selected from the group consisting of an electrophotographic photoreceptor, a photoelectric converter, a sensor, a dye laser, a solar cell device and an organic light emitting element, wherein the device comprises the organic light-emitting element of claim 15 .
18. A compound of formula
wherein
X is O, S or N—Y 4 —R 4 ,
Y 1 and Y 2 and Y 4 are independently of each other a direct bond, C 1 -C 25 -alkylene, or C 6 -C 10 -arylene, which is unsubstituted or substituted by one or more groups R 3 ;
R 1 and R 2 are independently of each other deuterium, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, which is unsubstituted or substituted by one or more groups R 3 , a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
R 3 is deuterium, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, or a C 6 -C 14 aryl group;
R 4 is a C 1 -C 25 alkyl group, a C 6 -C 10 aryl group, which is unsubstituted or substituted by one or more groups R 3 , or a group of formula (Xa) or (Xd);
X 1 is 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 hydrogen, deuterium, F, Cl, a C 1 -C 25 alkyl group, a C 1 -C 25 alkoxy group, a C 6 -C 14 aryloxy group, which is unsubstituted or substituted by one or more groups R 3 , or a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3 ;
R 15 , R 16 , R 17 , R 18 , R 19 and R 20 are independently of each other a C 1 -C 25 alkyl group, or a C 6 -C 14 aryl group, which is unsubstituted or substituted by one or more groups R 3 ;
wherein at least one group of formula (Xd) is present in the compound of formula (I).
19. A light-emitting layer comprising the compound according to claim 18 .
20. An organic light emitting element, comprising the compound according to claim 18 .
21. The organic light-emitting element according to claim 20 , characterized in that it emits light by delayed fluorescence.
22. A device selected from the group consisting of an electrophotographic photoreceptor, a photoelectric converter, a sensor, a dye laser, a solar cell device and an organic light emitting element, wherein the device comprises the organic light-emitting element of claim 20 .
23. A device selected from the group consisting of an electrophotographic photoreceptor, a photoelectric converter, a sensor, a dye laser, a solar cell device and an organic light emitting element, wherein the device comprises the organic light-emitting element of claim 7 .