US 12,082,496 B2
Composition material for organic electroluminescent device, plurality of host materials, and organic electroluminescent device comprising the same
Bitnari Kim, Gyeonggi-do (KR); Sang-Hee Cho, Gyeonggi-do (KR); Hyo-Jung Lee, Gyeonggi-do (KR); Ye-Jin Jeon, Gyeonggi-do (KR); Hyun-Ju Kang, Gyeonggi-do (KR); Su-Hyun Lee, Gyeonggi-do (KR); and Jeong-Eun Yang, Gyeonggi-do (KR)
Assigned to Rohm and Haas Electronic Materials Korea Ltd., (KR)
Appl. No. 17/042,652
Filed by ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD., Chungcheongnam-do (KR)
PCT Filed Mar. 26, 2019, PCT No. PCT/KR2019/003473
§ 371(c)(1), (2) Date Sep. 28, 2020,
PCT Pub. No. WO2019/190149, PCT Pub. Date Oct. 3, 2019.
Claims priority of application No. 10-2018-0035261 (KR), filed on Mar. 27, 2018; and application No. 10-2019-0030023 (KR), filed on Mar. 15, 2019.
Prior Publication US 2021/0028369 A1, Jan. 28, 2021
Int. Cl. C09K 11/06 (2006.01); C07D 209/86 (2006.01); C07D 209/88 (2006.01); C07D 403/04 (2006.01); C07D 403/10 (2006.01); C07D 487/16 (2006.01); C07F 15/00 (2006.01); C09K 11/02 (2006.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/00 (2023.01)
CPC H10K 85/636 (2023.02) [C07D 209/86 (2013.01); C07D 209/88 (2013.01); C07D 403/04 (2013.01); C07D 403/10 (2013.01); C07D 487/16 (2013.01); C07F 15/0033 (2013.01); C09K 11/02 (2013.01); C09K 11/06 (2013.01); H10K 85/342 (2023.02); H10K 85/633 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 85/615 (2023.02); H10K 85/626 (2023.02); H10K 2101/90 (2023.02)] 9 Claims
 
1. A composition material for an organic electroluminescent device comprising a compound represented by at least one of the following formulas 3 to 6 and a compound represented by the following formula 2:

OG Complex Work Unit Chemistry
wherein
Ar2 and Ar3 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;
L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
Y represents CR7R8, NR9, O, or S;
T1 to T13 each independently represent N or CV1;
V1 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or two adjacent V1's may be linked to each other to form a ring;
R2 to R9 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a ring;
L4 represents a single bond, a substituted or unsubstituted (C1-C30)alkylene, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
Ar4 represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl;
b, c, d, and f each independently represent an integer of 1 to 4, e represents an integer of 1 or 2, c′ represents an integer of 1 to 3, where if b to f and c′ each independently are an integer of 2 or more, each of R2 to Re may be the same or different; and

OG Complex Work Unit Chemistry
wherein
X1 represents N-L-(Ar)a, S, or O;
L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
Ar represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;
Y1 to Y12 each independently represent N or CR10;
R10 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a substituted or unsubstituted ring; and
a represents an integer of 1 to 4, where if a is an integer of 2 or more, each of Ar may be the same or different.