US 12,457,841 B2
Photoelectric conversion element and photoelectric conversion device including the photoelectric conversion element
Hiroyuki Watanabe, Shizuoka (JP); Akihiro Maruyama, Shizuoka (JP); Tatsuya Yamaai, Kanagawa (JP); Kenichi Kaku, Shizuoka (JP); Shuntaro Watanabe, Kanagawa (JP); Jumpei Kuno, Kanagawa (JP); Kazunori Noguchi, Ibaraki (JP); Takashi Anezaki, Kanagawa (JP); Nobuhiro Nakamura, Tokyo (JP); and Kohei Makisumi, Shizuoka (JP)
Assigned to Canon Kabushiki Kaisha, Tokyo (JP)
Filed by CANON KABUSHIKI KAISHA, Tokyo (JP)
Filed on Sep. 15, 2022, as Appl. No. 17/932,603.
Application 17/932,603 is a continuation of application No. PCT/JP2021/009941, filed on Mar. 12, 2021.
Claims priority of application No. 2020-049504 (JP), filed on Mar. 19, 2020; application No. 2020-096830 (JP), filed on Jun. 3, 2020; application No. 2020-112744 (JP), filed on Jun. 30, 2020; and application No. 2021-028128 (JP), filed on Feb. 25, 2021.
Prior Publication US 2023/0068976 A1, Mar. 2, 2023
Int. Cl. H10K 30/85 (2023.01); H01G 9/20 (2006.01); H10K 30/30 (2023.01); H10K 30/50 (2023.01); H10K 30/81 (2023.01); H10K 30/82 (2023.01); H10K 30/84 (2023.01); H10K 30/86 (2023.01); H10K 30/87 (2023.01); H10K 85/10 (2023.01); H10K 85/30 (2023.01); H10K 85/50 (2023.01); H10K 85/60 (2023.01)
CPC H10K 30/85 (2023.02) [H10K 30/30 (2023.02); H10K 30/50 (2023.02); H10K 30/84 (2023.02); H10K 30/86 (2023.02); H10K 30/87 (2023.02); H10K 85/111 (2023.02); H10K 85/141 (2023.02); H10K 85/30 (2023.02); H10K 85/50 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H01G 9/2009 (2013.01); H10K 30/81 (2023.02); H10K 30/82 (2023.02)] 9 Claims
OG exemplary drawing
 
1. A photoelectric conversion element comprising: a first layer containing a perovskite compound between an anode and a cathode; and a second layer between the cathode and the first layer,
wherein the second layer contains at least one of the structures represented by formula (U1) presented below and the structures represented by formula (U2) presented below;

OG Complex Work Unit Chemistry
wherein
in formulas (U1) and (U2), R1 and R3 each independently represent a substituted or unsubstituted alkylene group whose main chain has 1 to 10 atoms, or a substituted or unsubstituted phenylene group;
R2 represents a single bond, a substituted or unsubstituted alkylene group whose main chain has 1 to 10 atoms, or a substituted or unsubstituted phenylene group;
the substituent of the substituted alkylene group is an alkyl group, an aryl group, a hydroxy group, or a halogen atom;
the substituent of the substituted phenylene group is a halogen atom, a nitro group, a cyano group, a hydroxy group, an alkyl group, or a halogen-substituted alkyl group;
R9 represents a hydrogen atom or an alkyl group;
A1 represents any one of the groups represented by formulas (A-1) to (A-6) presented below;
B1 represents a group represented by any one of formulas (B-1) to (B-3) presented below;
D1 represents a group represented by formula (D) presented below and whose main chain has 5 to 15 atoms;
E1 represents a divalent group represented by any one of formulas (E-1) to (E-3) presented below;

OG Complex Work Unit Chemistry
in formula (A-5), R10 represents a hydrogen atom or an alkyl group;

OG Complex Work Unit Chemistry
in formulas (B-1) to (B-3), R6 and R7 each independently represent an alkylene group whose main chain has 1 to 5 atoms, an alkylene group which is substituted by an alkyl group with 1 to 5 carbon atoms and whose main chain has 1 to 5 atoms, a benzyl-substituted alkylene group whose main chain has 1 to 5 atoms, alkoxycarbonyl-substituted alkylene group whose main chain has 1 to 5 atoms, or a phenyl-substituted alkylene group whose main chain has 1 to 5 atoms;
one of the carbon atoms of the main chain of the alkylene group may be replaced with O, S, NH, or NR15, wherein R15 is an alkyl group;
R2 represents a single bond, a substituted or unsubstituted alkylene group whose main chain has 1 to 10 atoms, or a substituted or unsubstituted phenylene group;
the substituent of the substituted alkylene group is an alkyl group, an aryl group, a hydroxy group, or a halogen atom;
the substituent of the substituted phenylene group is a halogen atom, a nitro group, a cyano group, a hydroxy group, an alkyl group, or a halogen-substituted alkyl group;
R12 represents a hydrogen atom or an alkyl group;
Ar2 represents a substituted or unsubstituted phenylene group;
the substituent of the substituted phenylene group is a halogen atom, a nitro group, a hydroxy group, a cyano group, an alkyl group, or a halogenated alkyl group;
A1 and A2 represent any one of the groups represented by formulas (A-1) to (A-6) presented above;
E1 represents a divalent group represented by any one of formulas (E-1) to (E-3) presented below;
o, p, and q are each independently 0 or 1, and the sum of o, p, and q is 1 to 3;
arrows point to the side bound to R3;

OG Complex Work Unit Chemistry
in formula (D), R4, R5, R6, and R7 each independently represent an alkylene group whose main chain has 1 to 5 atoms, an alkylene group which is substituted by an alkyl group with 1 to 5 carbon atoms and whose main chain has 1 to 5 atoms, a benzyl-substituted alkylene group whose main chain has 1 to 5 atoms, an alkoxycarbonyl-substituted alkylene group whose main chain has 1 to 5 atoms, or a phenyl-substituted alkylene group whose main chain has 1 to 5 atoms;
one of the carbon atoms of the main chain of the alkylene group may be replaced with O, S, NH, or NR15, wherein R15 is an alkyl group;
Ar1 and Ar2 each independently represent a substituted or unsubstituted phenylene group;
the substituent of the substituted phenylene group is a halogen atom, a nitro group, a hydroxy group, a cyano group, an alkyl group, or a halogenated alkyl group;
A2 represents a group represented by any one of formulas (A-1) to (A-6) presented above;
I, m, n, o, p, and q are each independently 0 or 1, and the sum of I, m, and n and the sum of o, p, and q are 1 to 3;

OG Complex Work Unit Chemistry
in formulas (E-1) to (E-3), R101 to R106, R201 to R210, and R301 to R304 each independently represent a single bond, a hydrogen atom, a cyano group, a nitro group, a halogen atom, an alkoxycarbonyl group, a carboxyl group, a dialkylamino group, a hydroxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
two of R101 to R106, two of R201 to R210, and two of R301 to R304 are single bonds;
the substituent of the substituted alkyl group is an alkyl group, an aryl group, a halogen atom, or a carbonyl group; and
the substituent of the substituted aryl group or the substituted heterocyclic group is a halogen atom, a nitro group, a cyano group, an alkyl group, a halogen-substituted alkyl group, an alkoxy group, or a carbonyl group.