US 12,108,664 B2
Compound and organic semiconducting layer, organic electronic device, display device and lighting device comprising the same
Elena Galan Garcia, Dresden (DE); Benjamin Schulze, Dresden (DE); Jens Wutke, Dresden (DE); and Horst Hartmann, Dresden (DE)
Assigned to Novaled GmbH, Dresden (DE)
Appl. No. 17/259,762
Filed by Novaled GmbH, Dresden (DE)
PCT Filed Jul. 16, 2019, PCT No. PCT/EP2019/069132
§ 371(c)(1), (2) Date Jan. 12, 2021,
PCT Pub. No. WO2020/016233, PCT Pub. Date Jan. 23, 2020.
Claims priority of application No. 18184297.2 (EP), filed on Jul. 18, 2018.
Prior Publication US 2021/0367157 A1, Nov. 25, 2021
Int. Cl. H10K 85/60 (2023.01); C07D 221/18 (2006.01); C07D 251/24 (2006.01); C07D 405/04 (2006.01); H10K 50/16 (2023.01)
CPC H10K 85/654 (2023.02) [C07D 221/18 (2013.01); C07D 251/24 (2013.01); C07D 405/04 (2013.01); H10K 85/615 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 50/16 (2023.02)] 28 Claims
OG exemplary drawing
 
1. A compound according to formula 1:

OG Complex Work Unit Chemistry
wherein
R1, R2, R3 and R4 are independently selected from hydrogen, substituted or unsubstituted C6 to C38 aryl, substituted or unsubstituted C3 to C36 heteroaryl, substituted or unsubstituted C1 to C16 alkyl group, —PO(R′)2, D, F, CN, or formula 2;

OG Complex Work Unit Chemistry
 wherein
the substituents are selected from C6 to Cis aryl, C3 to C25 heteroaryl, —PO(R′)2, D, F, CN, C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkoxy, or partially or perdeuterated C1 to C16 alkoxy;
R′ is independently selected from alkyl, aryl or heteroaryl;
a, b, c, d and e are independently 0, 1 or 2, wherein at least one of a, b, c and d is 1 or 2;
wherein
at least one of R1, R2, R3 and R4 is formula 2,
Ar1 is selected from substituted or unsubstituted C6 to C38 arylene, substituted or unsubstituted C3 to C6 or C8 to C36 heteroarylene or substituted or unsubstituted C1 to C16 alkylene group, wherein
the substituents are selected from C6 to C18 aryl, C3 to C25 heteroaryl, —PO(R′)2, D, F, CN, C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkoxy, or partially or perdeuterated C1 to C16 alkoxy;
Ar2 is selected from substituted or unsubstituted C6 to C38 aryl, substituted or unsubstituted C3 to C6 or C8 to C36 heteroaryl, or substituted or unsubstituted C1 to C16 alkyl group, wherein
the substituents are selected from C6 to C18 aryl, C3 to C25 heteroaryl, —PO(R′)2, D, F, CN, C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkoxy, or partially or perdeuterated C1 to C16 alkoxy;
wherein
Ar1 does not contain one or more CN substituents when Ar2 is substituted or unsubstituted C6 to C38 aryl;
wherein
the following compound 3 is excluded:

OG Complex Work Unit Chemistry
wherein, when present, R1, R2, or both R1 and R2, independently, (i) comprises a triazine moiety, or (ii) comprises a cyano substituent, or (iii) is formula 2 at the 1-, 2-, or 4-position of the 9,10-diphenylphenanthrene moiety of formula 1, wherein e is 1 or 2, or (iv) a combination thereof;
wherein, when present, R3 (i) is not CN, (ii) is not an unsubstituted phenyl, (iii) is not an unsubstituted ethyl, (iv) is not a 4,6-diphenyl-1,3,5-triazin-2-yl, and (v) does not include a phenanthrenylene moiety; and
wherein, when present, R4 (i) is not CN, (ii) is not an unsubstituted phenyl, (iii) is not an unsubstituted ethyl, (iv) is not a 4,6-diphenyl-1,3,5-triazin-2-yl, and (v) does not include a phenanthrenylene moiety.