US 11,968,892 B2
Organic light emitting device containing a light emitting layer an anthracene derivative, and an organic material layer containing a compound including as sustituents a cyano group and a nitrogen-containing heteroring
Jungoh Huh, Daejeon (KR); Sung Kil Hong, Daejeon (KR); Miyeon Han, Daejeon (KR); and Jae Tak Lee, Daejeon (KR)
Assigned to LG CHEM, LTD., Seoul (KR)
Appl. No. 17/058,295
Filed by LG CHEM, LTD., Seoul (KR)
PCT Filed Sep. 20, 2019, PCT No. PCT/KR2019/012282
§ 371(c)(1), (2) Date Nov. 24, 2020,
PCT Pub. No. WO2020/060320, PCT Pub. Date Mar. 26, 2020.
Claims priority of application No. 10-2018-0112963 (KR), filed on Sep. 20, 2018.
Prior Publication US 2021/0210694 A1, Jul. 8, 2021
Int. Cl. H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01)
CPC H10K 85/654 (2023.02) [H10K 85/626 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 50/11 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02); H10K 50/18 (2023.02)] 16 Claims
OG exemplary drawing
 
1. An organic light emitting device, comprising:
an anode;
a cathode;
a light emitting layer provided between the anode and the cathode; and
an electron injection layer, an electron transfer layer, an electron injection and transfer layer, or an electron control layer provided between the cathode and the light emitting layer,
wherein the light emitting layer comprises a compound of the following Chemical Formula 1; and
the electron injection layer, the electron transfer layer, the electron injection and transfer layer, or the electron control layer provided between the cathode and the light emitting layer comprises a compound of the following Chemical Formula 2:

OG Complex Work Unit Chemistry
wherein in Chemical Formula 1:
L3 is a direct bond or a substituted or unsubstituted arylene group, or bonds to R1 to form a substituted or unsubstituted ring;
L4 is a direct bond or a substituted or unsubstituted arylene group;
Ar1 and Ar2 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;
R1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, —OR, —SiRaRbRc, —OSiRaRbRc, a substituted or unsubstituted aryl group, or —NRmRn, or bonds to L3 to form a substituted or unsubstituted ring;
R2 to R8 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, —OR, —SiRaRbRc, —OSiRaRbRc, a substituted or unsubstituted aryl group, or —NRmRn;
R, Ra, Rb, Rc, Rm and Rn are the same as or different from each other, and each independently is hydrogen, deuterium, an alkyl group, or an aryl group; and
the compound of Chemical Formula 1 comprises at least one deuterium;

OG Complex Work Unit Chemistry
HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group;
L2 is an unsubstituted phenylene group, a substituted or unsubstituted naphthylenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted divalent spiro[fluorene-9,9′-xanthene] group, a substituted or unsubstituted divalent pyridinyl group, a substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent benzimidazole group, or a substituted or unsubstituted divalent dibenzofuranyl group;
L is a substituted or unsubstituted divalent to tetravalent naphthyl group, a substituted or unsubstituted divalent to tetravalent fluorenyl group, a substituted or unsubstituted divalent to tetravalent anthracenyl group, a substituted or unsubstituted divalent to tetravalent spiro[fluorene-9,9′-xanthene] group, a substituted or unsubstituted divalent to tetravalent carbazolyl group, a substituted or unsubstituted divalent to tetravalent benzimidazole group, or a substituted or unsubstituted divalent to tetravalent dibenzofuranyl group;
L1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a terphenylene group, a substituted or unsubstituted naphthylenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted divalent spiro[fluorene-9,9′-xanthene] group, a substituted or unsubstituted divalent carbazole group, a substituted or unsubstituted divalent benzimidazole group, a substituted or unsubstituted divalent dibenzofuranyl group, or a 9,9-diphenylfluorenyl group;
a1 is an integer of 1 to 3, and when a1 is 2 or greater, the L1s are the same as or different from each other;
b1 is an integer of 1 to 3, and when b1 is 2 or greater, the L2s are the same as or different from each other;
a is 1 or 2;
b is 1 or 2, and when b is 2, the HArs are the same as or different from each other;
a2 is 1 or 2, and b2 is 1 or 2;
when a2 is 2, the -[(L1)a1-(CN)a]s are the same as or different from each other; and
when b2 is 2, the -[(L2)b1-(HAr)b]s are the same as or different from each other.