US 11,767,315 B2
Heterocyclic compound and organic light-emitting device including same
Min Woo Jung, Daejeon (KR); Dong Hoon Lee, Daejeon (KR); Boonjae Jang, Daejeon (KR); Jungha Lee, Daejeon (KR); Su Jin Han, Daejeon (KR); and Seulchan Park, Daejeon (KR)
Assigned to LG Chem, Ltd., Seoul (KR)
Appl. No. 16/967,201
Filed by LG CHEM, LTD., Seoul (KR)
PCT Filed Jun. 14, 2019, PCT No. PCT/KR2019/007198
§ 371(c)(1), (2) Date Aug. 4, 2020,
PCT Pub. No. WO2019/240532, PCT Pub. Date Dec. 19, 2019.
Claims priority of application No. 10-2018-0068054 (KR), filed on Jun. 14, 2018.
Prior Publication US 2021/0047306 A1, Feb. 18, 2021
Int. Cl. C07D 405/14 (2006.01); C07D 405/04 (2006.01); C07D 405/10 (2006.01); C07D 409/14 (2006.01); H01L 51/00 (2006.01); H01L 51/50 (2006.01); H10K 85/60 (2023.01)
CPC C07D 405/14 (2013.01) [C07D 405/04 (2013.01); C07D 405/10 (2013.01); C07D 409/14 (2013.01); H10K 85/615 (2023.02); H10K 85/654 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02)] 6 Claims
OG exemplary drawing
 
1. A heterocyclic compound of Chemical Formula 1:

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1:
X1 to X3 are the same as or different from each other, and each independently is N or CH;
at least two or more of X1 to X3 are N;
Y is O or S;
R1 and R2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, an unsubstituted alkyl group, an unsubstituted aryl group, or a silyl group selected from the group consisting of a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group;
R3 to R6 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, an unsubstituted alkyl group, a silyl group selected from the group consisting of a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group, an unsubstituted aryl group, or an unsubstituted heteroaryl group;
Ar1 and Ar2 are the same as or different from each other, and each independently is a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorene group, a spirobifluorene group, a phenanthrene group, a triphenylene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a benzonaphthofuran group, or a benzonaphthothiophene group, and the phenyl group, the biphenyl group, the naphthyl group, the terphenyl group, the fluorene group, the spirobifluorene group, the phenanthrene group, the triphenylene group, the carbazole group, the dibenzofuran group, the dibenzothiophene group, the benzonaphthofuran group, or the benzonaphthothiophene group is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, and a heteroaryl group having 3 to 30 carbon atoms that is unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms;
L1 and L2 are the same as or different from each other, and each independently is a direct bond, a phenylene group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a naphthylene group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a divalent biphenyl group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a divalent terphenyl group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a divalent quaterphenyl group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a divalent fluorene group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a divalent anthracene group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a divalent pyrene group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a divalent triphenylene group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or a divalent phenanthrene group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms;
Z is a nitrile group, a halogen group, an unsubstituted alkyl group having 1 to 10 carbon atoms, a silyl group that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group, or an unsubstituted heteroaryl group selected from the group consisting of a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, or a dibenzofuranyl group;
n is an integer of 1 to 2;
when n is 2, the Zs are the same as or different from each other; and
a and b are an integer of 0 to 5, and when a and b are a plural number, the substituents in the parentheses are the same as or different from each other.