US 12,396,361 B2
Imaging devices and imaging apparatuses
Naotoshi Suganuma, Yokohama (JP); Chul Joon Heo, Busan (KR); and Kyung Bae Park, Hwaseong-si (KR)
Assigned to Samsung Electronics Co., Ltd., Gyeonggi-do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Feb. 26, 2021, as Appl. No. 17/186,641.
Claims priority of application No. 2020-034248 (JP), filed on Feb. 28, 2020; and application No. 10-2021-0025996 (KR), filed on Feb. 25, 2021.
Prior Publication US 2021/0273188 A1, Sep. 2, 2021
Int. Cl. H10K 85/60 (2023.01); H10K 30/20 (2023.01); H10K 39/32 (2023.01); H10K 85/40 (2023.01)
CPC H10K 85/615 (2023.02) [H10K 30/211 (2023.02); H10K 39/32 (2023.02); H10K 85/40 (2023.02); H10K 85/626 (2023.02); H10K 85/649 (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)] 11 Claims
 
1. An imaging device, comprising:
a photoelectric conversion device including a sequential stack of an anode, a hole transport buffer layer, a photoelectric conversion layer, an electron transport buffer layer, and a cathode,
wherein the photoelectric conversion layer includes a p-type organic semiconductor and an n-type organic semiconductor,
wherein the electron transport buffer layer includes a compound represented by General Formula (1),
wherein the p-type organic semiconductor includes a compound represented by General Formula (2):

OG Complex Work Unit Chemistry
wherein, in General Formula (1),
Ar is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and
R1 to R4 are independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

OG Complex Work Unit Chemistry
wherein, in General Formula (2),
Ar3 is a substituted or unsubstituted hydrocarbon cyclic group including two carbonyl groups, or a substituted or unsubstituted heterocyclic group including two carbonyl groups,
R1 to R3 are independently a hydrogen atom, deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and R1 and R2 are optionally linked to each other to form a ring,
Arl and Ar2 are independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and
G1 and G2 are independently —(CRdRe)n—, —Te—, —O—, —S—, —Se—, —NRf—, —SiRgRh—, —SiRggRhh—, —GeRiRj—, —GeRiiRjj—, —(C(Rm))═(C(Rn))—, —(C(Rmm))═(C(Rnn))—, or a single bond, wherein Rd, Re, Rf, Rg, Rh, Ri, Rj, Rm, and Rn are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, Rgg, Rhh, Rii, Rjj, Rmm, and Rnn are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, at least one of Rgg and Rhh, Rii and Rjj, or Rmm and Rnn is linked to each other to form a ring, and n in —(CRdRe)n— is 1 or 2, and
wherein at least one of Ar, R1, R2, R3, or R4 in General Formula (1) is a non-condensed polycyclic aryl group, a condensed polycyclic aryl group, a monocyclic heteroaryl group, or a polycyclic heteroaryl group,
the condensed polycyclic aryl group is a phenanthryl group, a fluorenyl group, an indenyl group, a pyrenyl group, an acetonaftenyl group, a bisphenyl fluorenyl group, or a 9-(9-fluorenyl)fluorenyl group,
the monocyclic heteroaryl group is a pyrrolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, an oxadiazolyl group, a thiazolyl group, a pyranyl group, a pyrazyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, or an isoquinolyl group, and
the polycyclic heteroaryl group is a benzo(pyridyl)furanyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbonyl group, a phenanthridinyl group, an acridinyl group, a perimidinyl group, a phenanthrolinyl group, a benzooxazolyl group, a quinoxalyl group, a pyrazolyl group, a dibenzofuranyl group, or a dibenzothienyl group.