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US 12,108,664 B2Granted
Compound and organic semiconducting layer, organic electronic device, display device and lighting device comprising the same
AssigneeNovaled GmbH
InventorsElena Galan Garcia, Benjamin Schulze, Jens Wutke, Horst Hartmann
Life of this patent
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Abstract
The present invention relates to an organic compound of formula (1), suitable for use as a layer material for electronic devices, and it relates to an organic semiconductor layer comprising at least one compound thereof, as well as to an organic electronic device comprising at least one organic semiconductor layer, and a method of manufacturing the same.
Claims28
A compound according to formula 1:
- 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;
- 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:
- 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.
17 more elements
A compound of any one of structures J1 to J37 or J39 to J53, or a salt thereof:
A compound of the following structure or a salt thereof:
Dependencies are inferred from the claim text.