US 12,295,259 B2
Organic compound and organic electroluminescent device using same
Woojae Park, Yongin-si (KR); Minsik Eum, Yongin-si (KR); and Jaeyi Sim, Yongin-si (KR)
Assigned to SOLUS ADVANCED MATERIALS CO., LTD., Iksan-si (KR)
Appl. No. 17/312,788
Filed by SOLUS ADVANCED MATERIALS CO., LTD., Iksan-si (KR)
PCT Filed Dec. 12, 2019, PCT No. PCT/KR2019/017596
§ 371(c)(1), (2) Date Jun. 10, 2021,
PCT Pub. No. WO2020/122637, PCT Pub. Date Jun. 18, 2020.
Claims priority of application No. 10-2018-0161355 (KR), filed on Dec. 13, 2018.
Prior Publication US 2022/0052270 A1, Feb. 17, 2022
Int. Cl. H10K 85/60 (2023.01); C07D 239/26 (2006.01); C07D 251/24 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/654 (2023.02) [C07D 239/26 (2013.01); C07D 251/24 (2013.01); C09K 11/06 (2013.01); H10K 85/615 (2023.02); H10K 85/624 (2023.02); H10K 85/626 (2023.02); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/17 (2023.02); H10K 50/171 (2023.02); H10K 2101/10 (2023.02)] 12 Claims
 
1. A compound of the following Chemical Formula 1:

OG Complex Work Unit Chemistry
wherein in Chemical Formula 1,
Ra and Rb are the same as or different from each other, and are each independently a methyl group or a phenyl group, or combine with each other to form a fused ring,
m is 1, and n is an integer of 1 or 2,
wherein the cyano group (CN)-substituted ring is selected from the group of the following structural formulas:

OG Complex Work Unit Chemistry
wherein in the above structural formulas,
* represents a site where a bond is made with the compound of Chemical Formula 1,
Z1 to Z3 are the same as or different from each other, and are each independently N or C(R3), provided that Z1 to Z3 include at least one N,
R1 to R3 are the same as or different from each other, each independently being selected from the group consisting of: hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a C1 to C40 alkyl group, a C2 to C40 alkenyl group, a C2 to C40 alkynyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkylboron group, a C6 to C60 arylboron group, a C6 to C60 arylphosphine group, a C6 to C60 arylphosphine oxide group and a C6 to C60 arylamine group, and
with the proviso that:
(i) when Z1 to Z3 are all N, and n is 1, R1 and R2 are each a C6 to C60 aryl group,
(ii) when Z1 to Z3 are all N, n is 1, and R1 and R2 are each a C6 to C60 aryl group, R1 and R2 are different from each other, and
(iii) when Z1 to Z3 are all N, and n is 2, the compound of Chemical Formula 1 is selected from the group consisting of the compounds of the following Chemical Formula 4 to Chemical Formula 6:

OG Complex Work Unit Chemistry
wherein in Chemical Formulas 4 to 6,
Z1 to Z3, Ra and Rb, and R1 and R2 are as defined above, respectively,
the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group and the arylamine group of R1 to R3 are each independently substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, a C2 to C40 alkenyl group, a C2 to C40 alkynyl group, a C3 to C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1 to C40 alkyl group, a C6 to C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C40 alkyloxy group, a C6 to C60 aryloxy group, a C1 to C40 alkylsilyl group, a C6 to C60 arylsilyl group, a C1 to C40 alkylboron group, a C6 to C60 arylboron group, a C6 to C60 arylphosphine group, a C6 to C60 arylphosphine oxide group and a C6 to C60 arylamine group, and when the substituents are plural in number, the substituents are the same as or different from each other.