US 12,232,414 B2
Aromatic amine derivatives and organic electroluminescent elements using same
Tomoki Kato, Chiba (JP)
Assigned to IDEMITSU KOSAN CO., LTD., Tokyo (JP)
Filed by IDEMITSU KOSAN CO., LTD., Tokyo (JP)
Filed on Apr. 13, 2022, as Appl. No. 17/719,823.
Application 15/436,352 is a division of application No. 14/933,453, filed on Nov. 5, 2015, granted, now 9,614,160, issued on Apr. 4, 2017.
Application 17/719,823 is a continuation of application No. 16/424,061, filed on May 28, 2019, granted, now 11,335,858.
Application 16/424,061 is a continuation of application No. 15/436,352, filed on Feb. 17, 2017, granted, now 10,355,218, issued on Jul. 16, 2019.
Application 14/933,453 is a continuation of application No. 13/399,412, filed on Feb. 17, 2012, granted, now 9,260,390, issued on Feb. 16, 2016.
Application 13/399,412 is a continuation of application No. PCT/JP2010/063425, filed on Aug. 6, 2010.
Claims priority of application No. 2009-190398 (JP), filed on Aug. 19, 2009.
Prior Publication US 2022/0255005 A1, Aug. 11, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/60 (2023.01); C07D 209/86 (2006.01); C07D 307/91 (2006.01); C07D 333/76 (2006.01); C07D 405/12 (2006.01); C09K 11/06 (2006.01); H05B 33/14 (2006.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01)
CPC H10K 85/633 (2023.02) [C07D 209/86 (2013.01); C07D 307/91 (2013.01); C07D 333/76 (2013.01); C07D 405/12 (2013.01); C09K 11/06 (2013.01); H10K 85/636 (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); C09K 2211/1022 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1088 (2013.01); H05B 33/14 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/17 (2023.02); H10K 85/615 (2023.02); H10K 85/626 (2023.02)] 25 Claims
 
1. An aromatic amine derivative of formula (I):

OG Complex Work Unit Chemistry
wherein Ara is of formula (II):

OG Complex Work Unit Chemistry
wherein
R1 and R2 are each a linear or branched alkyl group having 1 to 50 carbon atoms, or an aryl group having 6 to 50 ring carbon atoms,
R3 is independently a linear or branched alkyl group having 1 to 50 carbon atoms, a linear or branched alkenyl group having 3 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an aryl group having 6 to 50 ring carbon atoms, a heteroaryl group having 5 to 50 ring atoms, a triarylalkyl group having aryl groups each having 6 to 50 ring carbon atoms, a trialkylsilyl group having alkyl groups each having 1 to 50 carbon atoms, a triarylsilyl group having aryl groups each having 6 to 50 ring carbon atoms, an alkylarylsilyl group having an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, a halogen atom, or a cyano group, such that a plurality of R3s adjacent to each other are optionally bonded to each other to form a ring,
o is an integer in a range of from 0 to 3,
Arb is of formula (IIIa) or (IIIb):

OG Complex Work Unit Chemistry
wherein
R7 is a linear or branched alkyl group having 1 to 50 carbon atoms, a linear or branched alkenyl group having 3 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an aryl group having 6 to 50 ring carbon atoms, a heteroaryl group having 6 to 50 ring atoms, a triarylalkyl group having aryl groups each having 6 to 50 ring carbon atoms, a trialkylsilyl group having alkyl groups each having 1 to 50 carbon atoms, a triarylsilyl group having aryl groups each having 6 to 50 ring carbon atoms, an alkylarylsilyl group having an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, a halogen atom, or a cyano group,
n is 0, 1, or 2, and when n is 2, R7s on different benzene rings are identical to or different from each other, and respective R7s present on benzene rings adjacent to each other are optionally bonded to each other to form a ring,
s is 0 or 1, and
Arc is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or is of formula (IIIa) or (IIIb), and Arc is not a fluorenyl group and is not a substituted or unsubstituted terphenylyl group.