US 12,448,397 B2
Composition for photoelectric device, and photoelectric device, image sensor and electronic device including the same
Jeong Il Park, Seongnam-si (KR); Cheol Ham, Yongin-si (KR); Hyeongju Kim, Changwon-si (KR); Feifei Fang, Suwon-si (KR); Sung Young Yun, Suwon-si (KR); Youn Hee Lim, Suwon-si (KR); and Hye Rim Hong, Suwon-si (KR)
Assigned to Samsung Electronics Co., Ltd., Gyeonggi-do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Mar. 7, 2022, as Appl. No. 17/688,051.
Claims priority of application No. 10-2021-0029757 (KR), filed on Mar. 5, 2021.
Prior Publication US 2022/0289767 A1, Sep. 15, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 517/22 (2006.01); H10K 30/20 (2023.01); H10K 30/40 (2023.01); H10K 30/80 (2023.01); H10K 30/84 (2023.01); H10K 39/32 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01)
CPC C07D 517/22 (2013.01) [H10K 30/20 (2023.02); H10K 39/32 (2023.02); H10K 85/40 (2023.02); H10K 85/615 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 30/40 (2023.02); H10K 30/80 (2023.02); H10K 30/84 (2023.02)] 27 Claims
 
1. A composition for a photoelectric device, the composition comprising:
a p-type semiconductor compound represented by Chemical Formula 1 and an n-type semiconductor compound:

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1,
L is —O—, —S—, —Se—, —Te—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRg)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, —(C(Rp)═N)—, or a single bond, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are each independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, each pair of Rbb and Rcc, Rdd and Ree, Rff and Rgg, or Rmm and Rnn are linked to each other to form a ring structure, and n1 of —(CRfRg)n1— is 1 or 2, or L is linked to Y1 or Y4 to provide a ring structure,
Y1 to Y6 are each independently N or CRk, wherein Rk is hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, amine group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group or adjacent Rk's are linked to each other to provide a substituted or unsubstituted C6 to C30 arene group, a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof,
X1 is —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —CRfRg—, or —CRffRgg—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, and Rg are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C6 to C20 aryloxy group, or a substituted or unsubstituted C3 to C20 heteroaryl group, and each pair of Rbb and Rcc, Rdd and Ree, or Rff and Rgg are linked to each other to provide a ring structure,
X2 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRg)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, or —(C(Rp)═N)—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are each independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C6 to C20 aryloxy group or a substituted or unsubstituted C3 to C20 heteroaryl group, and each pair of Rbb and Rcc, Rdd and Ree, Rff and Rgg, or Rmm and Rnn is linked to each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
Ar3 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a fused ring thereof, and
R1 and R2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group (—CN), a cyano-containing group, a nitro group, a pentafluorosulfanyl group (—SF5), a hydroxyl group, an amine group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SiRaRbRc, wherein Ra, Rb, and Rc are each independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group, or any combination thereof.