Granted Patent B2

US 12,435,099 · App. 17/628,432 · Granted Oct 7, 2025

Inventors: Sebastian Dück (Heidelberg, DE); Alhama Arjona Esteban (Karlsruhe, DE); Federico Koch (Schonungen, DE)

Assignee: Samsung Display Co., Ltd.

C07F5/027C07C15/28C07C211/54C07D307/91C07D401/14C07D403/14C07F7/0805H10K85/322H10K85/40H10K85/615H10K85/631H10K85/654H10K85/6572H10K85/6574H10K85/658H10K50/11H10K50/15H10K50/16H10K50/17H10K50/171H10K50/18H10K50/81H10K50/82

Abstract

Claims (101)

1. An organic molecule of Formula Ib:

wherein

each of R II , and R III is independently selected from the group consisting of:

hydrogen,

deuterium,

N(R 5 ) 2 ,

OR 5 ,

SR 5 ,

Si(R 5 ) 3 ,

B(OR 5 ) 2 ,

OSO 2 R 5 ,

CF 3 ,

CN,

halogen,

C 1 -C 40 -alkyl,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 1 -C 40 -alkoxy,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 1 -C 40 -thioalkoxy,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 2 -C 40 -alkenyl,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 2 -C 40 -alkynyl,

which is optionally substituted with one or more substituents R 5 and

wherein one or more non-adjacent CH 2 -groups are optionally substituted by R 5 C═CR 5 , C≡C, Si(R 5 ) 2 , Ge(R 5 ) 2 , Sn(R 5 ) 2 , C═O, C═S, C═Se, C═NR 5 , P(═O)(R 5 ), SO, SO 2 , NR 5 , O, S or CONR 5 ;

C 6 -C 60 -aryl,

which is optionally substituted with one or more substituents R 5 ; and

C 3 -C 57 -heteroaryl,

which is optionally substituted with one or more substituents R 5 ;

R 5 is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, OPh, SPh, CF 3 , CN, F, Si(C 1 -C 5 -alkyl) 3 , Si(Ph) 3 ,

C 1 -C 5 -alkyl,

wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;

C 1 -C 5 -alkoxy,

wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;

C 1 -C 5 -thioalkoxy,

wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;

C 2 -C 5 -alkenyl,

wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;

C 2 -C 5 -alkynyl,

wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F;

C 6 -C 18 -aryl,

which is optionally substituted with one or more C 1 -C 5 -alkyl substituents;

C 3 -C 17 -heteroaryl,

which is optionally substituted with one or more C 1 -C 5 -alkyl substituents;

N(C 6 -C 18 -aryl) 2 ,

N(C 3 -C 17 -heteroaryl) 2 ; and

N(C 3 -C 17 -heteroaryl)(C 6 -C 18 -aryl);

R V is at each occurrence independently selected from the group consisting of: C 1 -C 5 -alkyl,

wherein one or more hydrogen atoms are optionally substituted by deuterium;

R VI is at each occurrence independently selected from the group consisting of:

C 6 -C 18 -aryl,

wherein optionally one or more hydrogen atoms are independently from each other substituted by C 1 -C 5 -alkyl, C 6 -C 18 aryl or C 3 -C 17 -heteroaryl;

C 3 -C 15 -heteroaryl,

wherein optionally one or more hydrogen atoms are independently from each other substituted by C 1 -C 5 -alkyl, C 6 -C 18 aryl or C 3 -C 17 -heteroaryl.

2. The organic molecule according to claim 1 , wherein R II , and R III are independently from each other selected from the group consisting of: hydrogen, deuterium, halogen, Me, i Pr, tBu, CN, CF 3 , SiMe 3 , SiPh 3 ,

Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph,

triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph, and N(Ph) 2 .

3. An optoelectronic device comprising the organic molecule according to claim 2 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

4. The optoelectronic device according to claim 3 , comprising:

a substrate;

an anode;

a cathode, wherein the anode or the cathode is applied to the substrate; and

at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

5. The organic molecule according to claim 1 , wherein

each of R II , and R III is independently selected from the group consisting of:

hydrogen, deuterium, Me, i Pr, tBu, SiMe 3 , SiPh 3 ,

Ph, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, and Ph,

and N(Ph) 2 .

6. The organic molecule according to claim 1 , wherein R II is equal to R III .

7. The organic molecule according to claim 1 , wherein R V is methyl (Me), wherein one or more hydrogen atoms are optionally substituted by deuterium.

8. The organic molecule according to claim 1 , wherein R VI is at each occurrence independently from each other selected from the group consisting of

C 1 -C 5 -alkyl, and

C 6 -C 18 -aryl,

wherein optionally one or more hydrogen atoms are independently from each other substituted by C 1 -C 5 -alkyl or C 6 -C 18 -aryl.

9. A composition, comprising:

(a) an organic molecule according to claim 1 as an emitter and/or a host;

(b) an emitter and/or a host material different from the organic molecule according to claim 1 ; and

(c) optionally, a dye and/or a solvent.

10. An optoelectronic device comprising the composition according to claim 9 .

11. The optoelectronic device according to claim 10 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

12. The optoelectronic device according to claim 10 , comprising:

a substrate;

an anode;

a cathode, wherein the anode or the cathode is disposed on the substrate; and

at least one light-emitting layer disposed between the anode and the cathode and which comprises the composition.

13. An optoelectronic device comprising the organic molecule according to claim 1 .

14. The optoelectronic device according to claim 13 , wherein the optoelectronic device is an organic light-emitting diode, a light-emitting electrochemical cell, an organic light-emitting sensor, an organic diode, an organic solar cell, an organic transistor, an organic field-effect transistor, an organic laser or a down-conversion element.

15. The optoelectronic device according to claim 13 , comprising:

a substrate;

an anode;

a cathode, wherein the anode or the cathode is disposed on the substrate; and

at least one light-emitting layer disposed between the anode and the cathode and which comprises the organic molecule.

16. An optoelectronic device comprising the organic molecule according to claim 1 , wherein the organic molecule is one of a luminescent emitter, an electron transport material, a hole injection material or a hole blocking material in the optoelectronic device.

17. A method for producing an optoelectronic device, comprising processing of the organic molecule according to claim 1 by a vacuum evaporation method or from a solution.

Assignments (2)

Priority Claims (5)

Continuity (1)

References Cited (22)