US 12,490,652 B2
Organic optoelectronic device and display device
Byungku Kim, Yongin-si (KR); Giwook Kang, Yongin-si (KR); Dong Min Kang, Yongin-si (KR); Jun Seok Kim, Yongin-si (KR); Eun Sun Yu, Yongin-si (KR); Sangshin Lee, Yongin-si (KR); Sangil Lee, Yongin-si (KR); Kipo Jang, Yongin-si (KR); and Jinhyun Lui, Yongin-si (KR)
Assigned to SAMSUNG SDI CO., LTD., Yongin-si (KR)
Filed by SAMSUNG SDI CO., LTD., Yongin-si (KR)
Filed on Nov. 6, 2019, as Appl. No. 16/675,543.
Claims priority of application No. 10-2018-0136029 (KR), filed on Nov. 7, 2018.
Prior Publication US 2020/0144510 A1, May 7, 2020
Int. Cl. H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/636 (2023.02) [H10K 85/622 (2023.02); H10K 85/633 (2023.02); H10K 85/654 (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 2101/10 (2023.02); H10K 2101/90 (2023.02)] 11 Claims
OG exemplary drawing
 
1. An organic optoelectronic device, comprising:
an anode and a cathode facing each other,
a light emitting layer disposed between the anode and the cathode, the light emitting layer including a first compound represented by Chemical Formula 1E-2-2, and a second compound represented by Chemical Formula 3-1a, Chemical Formula 3-2, or Chemical Formula 3-3a,
a hole transport layer disposed between the anode and the light emitting layer, and
a hole transport auxiliary layer disposed between the light emitting layer and the hole transport layer, the hole transport auxiliary layer including a third compound represented by Chemical Formula 4,

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1E-2-2,
X1 is O or S,
La, Lb, Lc, L1, L2, L3, and L4 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted divalent C2 to C20 heterocyclic group, or a combination thereof, provided that at least one of Lb or Lc is a phenylene group,
Ra, R1, R2, and R4 to R6 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
Rb is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and
Rc is a substituted or unsubstituted fluorenyl group,

OG Complex Work Unit Chemistry
in Chemical Formula 3-1a,
L6 is a single bond,
L8 and L10 are each independently a single bond or a substituted or unsubstituted phenylene group,
R8 is an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenyl group,
R10 and R12 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
at least one of R10 and R12 is a substituted or unsubstituted naphthyl group, and
-L6-R8 is different from -L8-R10, -L6-R8 is different from -L10-R12, and -L8-R10 is different from -L10-R12;

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 3-2,
Z1 is N or C-L5-R7,
Z4 is N or C-L8-R10,
Z5 is N or C-L9-R11,
at least two of Z1, Z4, and Z5 are N,
L5, L8, L9, and L10 are each independently a single bond, an unsubstituted C6 to C20 arylene group, a substituted or unsubstituted divalent C2 to C20 heterocyclic group, or a combination thereof,
R7, R10, R11, and R12 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
at least one of R7, R10, and R11 is independently an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenyl group, and
Rd and Re are each independently hydrogen, deuterium, a halogen, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a combination thereof,

OG Complex Work Unit Chemistry
in Chemical Formula 3-3a,
X3 is O or S, and
L5 and L9 are each independently a single bond, an unsubstituted C6 to C20 arylene group, a substituted or unsubstituted divalent C2 to C20 heterocyclic group, or a combination thereof,
R7 is an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenyl group,
R11 is a substituted or unsubstituted carbazolyl group, and
Rf and Rg are each independently hydrogen, deuterium, a halogen, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a combination thereof;

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 4,
X2 is O or S,
L11 to L16 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted divalent C2 to C20 heterocyclic group, or a combination thereof,
R13 to R16 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
R17 and R18 are each independently hydrogen, deuterium, a cyano group, or a substituted or unsubstituted C1 to C10 alkyl group.