US 12,089,491 B2
Light-emitting element, light-emitting device, electronic device, and lighting device
Sachiko Kawakami, Kanagawa (JP); Tsunenori Suzuki, Kanagawa (JP); Yusuke Takita, Kanagawa (JP); and Satoshi Seo, Kanagawa (JP)
Assigned to Semiconductor Energy Laboratory Co., Ltd., Atsugi (JP)
Filed by SEMICONDUCTOR ENERGY LABORATORY CO., LTD., Atsugi (JP)
Filed on Aug. 13, 2021, as Appl. No. 17/401,948.
Application 17/401,948 is a continuation of application No. 16/533,881, filed on Aug. 7, 2019, granted, now 11,101,432.
Application 16/533,881 is a continuation of application No. 15/416,348, filed on Jan. 26, 2017, granted, now 10,411,193, issued on Sep. 10, 2019.
Claims priority of application No. 2016-016262 (JP), filed on Jan. 29, 2016.
Prior Publication US 2021/0384440 A1, Dec. 9, 2021
Int. Cl. H01L 51/50 (2006.01); C07D 307/77 (2006.01); C09K 11/06 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 59/121 (2023.01); H10K 101/30 (2023.01); H10K 101/40 (2023.01)
CPC H10K 85/636 (2023.02) [C07D 307/77 (2013.01); C09K 11/06 (2013.01); H10K 85/633 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1014 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/156 (2023.02); H10K 59/1213 (2023.02); H10K 85/622 (2023.02); H10K 85/626 (2023.02); H10K 2101/30 (2023.02); H10K 2101/40 (2023.02)] 21 Claims
OG exemplary drawing
 
1. An organic compound represented by General Formula (G1),

OG Complex Work Unit Chemistry
wherein R1 and R3 to R8 independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,
wherein R2 represents hydrogen, and
wherein one of A and B represents a group represented by General Formula (g1) and the other represents any one of hydrogen, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,

OG Complex Work Unit Chemistry
wherein Ar1 and Ar2 independently represent any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms and a group represented by General Formula (g2), and in Ar1 and Ar2, a substituent of the substituted aromatic hydrocarbon group having 6 to 60 carbon atoms is any of a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituent represented by Formulae (1-41) to (1-135),

OG Complex Work Unit Chemistry

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OG Complex Work Unit Chemistry

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OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

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OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein R11 to R18 independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,
wherein one of Z1 and Z2 is bonded to a nitrogen atom in General Formula (g1) and the other represents any one of hydrogen, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and
wherein at least one of Ar1 and Ar2 represents a group represented by General Formula (g2).
 
8. An organic compound represented by General Formula (G1),

OG Complex Work Unit Chemistry
wherein R1 and R3 to R8 independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,
wherein R2 represents hydrogen, and
wherein one of A and B represents a group represented by General Formula (g1) and the other represents any one of hydrogen, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,

OG Complex Work Unit Chemistry
wherein Ar1 and Ar2 independently represent any one of an unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms and a group represented by General Formula (g2), and in the case Ar1 and Ar2 have a substituent, the substituent excludes a dinaphthothiophenyl group and a fluorenyl group,

OG Complex Work Unit Chemistry
wherein R11 to R18 independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,
wherein one of Z1 and Z2 is bonded to a nitrogen atom in General Formula (g1) and the other represents any one of hydrogen, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and
wherein at least one of Ar1 and Ar2 represents a group represented by General Formula (g2).
 
15. An organic compound represented by General Formula (G1),

OG Complex Work Unit Chemistry
wherein R1 and R3 to R8 independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,
wherein R2 represents hydrogen, and
wherein one of A and B represents a group represented by General Formula (g1) and the other represents any one of hydrogen, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,

OG Complex Work Unit Chemistry
wherein Ar1 and Ar2 independently represent any one of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms and a group represented by General Formula (g2), and in the case Ar1 and Ar2 have a substituent, the substituent excludes a dinaphthothiophenyl group and a fluorenyl group,

OG Complex Work Unit Chemistry
wherein R11 to R18 independently represent any one of hydrogen, a hydrocarbon group having 1 to 6 carbon atoms, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms,
wherein one of Z1 and Z2 is bonded to a nitrogen atom in General Formula (g1) and the other represents any one of hydrogen, a cyclic hydrocarbon group having 3 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cyano group, halogen, a haloalkyl group having 1 to 6 carbon atoms, a hydrocarbon group having 1 to 6 carbon atoms, and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 60 carbon atoms, and
wherein at least one of Ar1 and Ar2 represents a group represented by General Formula (g2).