US 11,685,859 B2
Organic light emitting device
Jae Seung Ha, Daejeon (KR); Yeon Hwan Kim, Daejeon (KR); Sang Young Jeon, Daejeon (KR); Sung Kil Hong, Daejeon (KR); Yong Bum Cha, Daejeon (KR); and Seong Mi Cho, Daejeon (KR)
Assigned to LG CHEM, LTD., Seoul (KR)
Appl. No. 16/754,904
Filed by LG CHEM, LTD., Seoul (KR)
PCT Filed Oct. 5, 2018, PCT No. PCT/KR2018/011790
§ 371(c)(1), (2) Date Apr. 9, 2020,
PCT Pub. No. WO2019/117440, PCT Pub. Date Jun. 20, 2019.
Claims priority of application No. 10-2017-0170536 (KR), filed on Dec. 12, 2017.
Prior Publication US 2021/0009894 A1, Jan. 14, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C09K 11/06 (2006.01); H10K 50/15 (2023.01); H10K 50/165 (2023.01); H10K 85/60 (2023.01)
CPC C09K 11/06 (2013.01) [H10K 50/156 (2023.02); H10K 50/165 (2023.02); H10K 85/631 (2023.02); H10K 85/6572 (2023.02); C09K 2211/1014 (2013.01); C09K 2211/1029 (2013.01)] 15 Claims
 
1. An organic light emitting device comprising:
an anode;
a hole transport layer;
a hole control layer;
a light emitting layer;
an electron transport layer; and
a cathode,
wherein:
the hole control layer includes a compound of the following Chemical Formula 1, and
the light emitting layer includes (i) a compound of the following Chemical Formula 2-1, or a compound of the following Chemical Formula 2-2; and (ii) a compound of the following Chemical Formula 3:

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1:
L11 is a single bond or a substituted or unsubstituted C6-60 arylene;
L12 and L13 are each independently a single bond or a substituted or unsubstituted C6-60 arylene;
R11 is a substituted or unsubstituted C6-60 aryl;
R12 and R13 are each independently any one substituent selected from the group consisting of the following:

OG Complex Work Unit Chemistry
wherein, each R′ is independently a substituted or unsubstituted C6-60 aryl;
R14 and R15 are hydrogen, or are linked to each other;

OG Complex Work Unit Chemistry
wherein, in Chemical Formulas 2-1 and 2-2;
X2 is O or S;
each Y2 is independently N or CH, with the proviso that at least one of Y2 is N;
L21, L22, L23, and L24 are each independently a single bond or a substituted or unsubstituted C6-60 arylene;
R21 is a substituted or unsubstituted C6-60 aryl or the following substituent:

OG Complex Work Unit Chemistry
wherein:
X′ is C or Si, and each R″ is independently hydrogen, C1-60 alkyl, or Si(C1-60 alkyl)3;
R23 and R24 are each independently a substituted or unsubstituted C6-60 aryl or a substituted or unsubstituted C2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O, and S;
R25 and R26 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-60 alkyl, cyano, or a substituted or unsubstituted C6-60 aryl;
n and m are each independently an integer of 1 to 3;

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 3:
L31 is a single bond or a substituted or unsubstituted C6-60 arylene;
L32 is a single bond or a substituted or unsubstituted C6-60 arylene;
R31 is a substituted or unsubstituted C3-60 cycloalkyl, a substituted or unsubstituted C1-60 alkyl, a substituted or unsubstituted C6-60 aryl, or a substituted or unsubstituted C2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S;
R32 and R33 are each independently hydrogen, cyano, a substituted or unsubstituted C1-60 alkyl, a substituted or unsubstituted C6-60 aryl, or a substituted or unsubstituted C2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S;
X3 is O, S, C(CH3)2, N—R34, or

OG Complex Work Unit Chemistry
and
R34 is a substituted or unsubstituted C6-60 aryl.