US 12,071,447 B2
Composition for photoelectric device, and image sensor and electronic device including the same
Hyeongju Kim, Changwon-si (KR); Hye Rim Hong, Suwon-si (KR); Kyung Bae Park, Hwaseong-si (KR); Jeong Il Park, Seongnam-si (KR); Sung Young Yun, Suwon-si (KR); Seon-Jeong Lim, Yongin-si (KR); Youn Hee Lim, Suwon-si (KR); and Taejin Choi, Suwon-si (KR)
Assigned to Samsung Electronics Co., Ltd., Gyeonggi-do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Aug. 27, 2021, as Appl. No. 17/459,582.
Claims priority of application No. 10-2020-0110628 (KR), filed on Aug. 31, 2020.
Prior Publication US 2022/0073542 A1, Mar. 10, 2022
Int. Cl. C07F 7/08 (2006.01); H10K 30/82 (2023.01); H10K 39/32 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01)
CPC C07F 7/0816 (2013.01) [H10K 30/82 (2023.02); H10K 39/32 (2023.02); H10K 85/40 (2023.02); H10K 85/6572 (2023.02)] 31 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,
Ar1 and Ar2 are each independently 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 at least one pair of Rbb and Rcc, Rdd and Ree, or Rff and Rgg is linked with 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, Re, 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, at least one pair of Rbband Rcc, Rdd and Ree, Rff and Rgg, or Rmm and Rnn is linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
R11 and R12 are each independently hydrogen, deuterium, a halogen, a cyano group, 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, wherein R11 and R12 are each independently present or are linked to each other to provide a ring structure, or SiR11R12 is optionally linked with Ar1 or Ar2 to providing a ring structure,
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 a combination thereof.