US 12,225,813 B2
Organic compound and organic electroluminescent device comprising the same
Hyung Chan Bae, Yongin-si (KR); Young Bae Kim, Yongin-si (KR); and Ho Jun Son, Yongin-si (KR)
Assigned to DOOSAN SOLUS CO., LTD., Iksan-si (KR)
Appl. No. 16/615,891
Filed by DOOSAN SOLUS CO., LTD., Iksan-si (KR)
PCT Filed May 2, 2018, PCT No. PCT/KR2018/005076
§ 371(c)(1), (2) Date Nov. 22, 2019,
PCT Pub. No. WO2018/216921, PCT Pub. Date Nov. 29, 2018.
Claims priority of application No. 10-2017-0063365 (KR), filed on May 23, 2017.
Prior Publication US 2020/0144511 A1, May 7, 2020
Int. Cl. H10K 85/60 (2023.01); C07D 263/57 (2006.01); C07D 405/10 (2006.01); C07D 405/14 (2006.01); C07D 409/10 (2006.01); C07D 413/10 (2006.01); C07D 413/14 (2006.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/17 (2023.01); H10K 71/00 (2023.01); H10K 71/16 (2023.01); H10K 101/10 (2023.01); H10K 102/00 (2023.01)
CPC H10K 85/654 (2023.02) [C07D 263/57 (2013.01); C07D 405/10 (2013.01); C07D 405/14 (2013.01); C07D 409/10 (2013.01); C07D 413/10 (2013.01); C07D 413/14 (2013.01); H10K 85/636 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/17 (2023.02); H10K 71/00 (2023.02); H10K 71/164 (2023.02); H10K 2101/10 (2023.02); H10K 2102/351 (2023.02)] 12 Claims
 
1. A compound of the following Chemical Formula 1:

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1,
L1 is selected from the group consisting of a single bond, a C6˜C18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
Ar1 is a substituent represented by any one of the following Chemical Formula 13, Chemical Formula 14, and Chemical Formula C-1 to Chemical Formula C-6,

OG Complex Work Unit Chemistry
in Chemical Formulas 13, 14, and C1-C6,
* means a part where a bond is formed;
Z1, Z3 and Z5 are each independently N or C (R8), wherein at least one of Z1, Z3 and Z5 is N;
o is an integer of 0 to 4;
R8 to R14 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylamine group, or bond to adjacent groups to form a fused ring; and
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group of R8, to R14 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;
any one of X1 and X2, X2 and X3, X3 and X4, and X4 and X5 bonds to a ring of the following Chemical Formula 2 or 4 to form a fused ring;
m and n are an integer of 4;
R1 and R2 are hydrogen;
X1 to X5 not forming a fused ring with a ring of the following Chemical Formula 2 or 4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylsulfonyl group, a C6˜C60 arylsulfonyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group, a C1˜C40 alkylcarbonyl group, a C6˜C60 arylcarbonyl group and a C6˜C60 arylamine group; and
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group and the arylsilyl group of R1, R2, and X1 to X5 not forming a fused ring with a ring represented by the following Chemical Formula 2 or 4 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other;

OG Complex Work Unit Chemistry
wherein in Chemical Formula 2 or 4,
wherein in Chemical Formula 2 or 4,
a dotted line means a part that is fused to Chemical Formula 1;
p is an integer of 0 to 5;
Y1 is O;
R3 is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1˜C40 alkyloxy group, a C6˜C60 aryloxy group, a C3˜C40 alkylsilyl group, a C6˜C60 arylsilyl group, a C1˜C40 alkylsulfonyl group, a C6˜C60 arylsulfonyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group, a C1˜C40 alkylcarbonyl group, a C6˜C60 arylcarbonyl group and a C6˜C60 arylamine group; and
the alkyl group, the alkenyl group, the alkynyl group, the aryl group, the heteroaryl group, the aryloxy group, the alkyloxy group, the cycloalkyl group, the heterocycloalkyl group, the arylamine group, the alkylsilyl group, the alkylsulfonyl group, the arylsulfonyl group, the alkylboron group, the arylboron group, the arylphosphanyl group, the mono or diarylphosphinyl group, the alkylcarbonyl group, the arylcarbonyl group and the arylsilyl group of R3 to R6 are each independently unsubstituted or substituted with one or more types of substituents selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C1˜C40 alkyl group, a C2˜C40 alkenyl group, a C2˜C40 alkynyl group, a C6˜C60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C6˜C60 aryloxy group, a C1˜C40 alkyloxy group, a C6˜C60 arylamine group, a C3˜C40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C1˜C40 alkylsilyl group, a C1˜C40 alkylsulfonyl group, a C6˜C60 arylsulfonyl group, a C1˜C40 alkylboron group, a C6˜C60 arylboron group, a C6˜C60 arylphosphanyl group, a C6˜C60 mono or diarylphosphinyl group, a C1˜C40 alkylcarbonyl group, a C6˜C60 arylcarbonyl group and a C6˜C60 arylsilyl group, and when substituted with a plurality of the substituents, these are the same as or different from each other.