US2016149144A1 · US · A1
| Field | Value |
|---|---|
| Publication number | US-2016149144-A1 |
| Application number | US-201615012203-A |
| Country | US |
| Kind code | A1 |
| Filing date | Feb 1, 2016 |
| Priority date | Aug 2, 2013 |
| Publication date | May 26, 2016 |
| Grant date | — |
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An object of the invention is to provide: a photoelectric conversion material which has excellent deposition stability such that when the photoelectric conversion material is used in a photoelectric conversion element, the change in the performance of the element due to variations in the concentration of the photoelectric conversion material is small; a photoelectric conversion element using the photoelectric conversion material; and an optical sensor and an imaging element including the photoelectric conversion element. The photoelectric conversion material of the invention is a compound (A) expressed by the following Formula (1).
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What is claimed is: 1 . A photoelectric conversion material which is a compound (A) expressed by the following Formula (1), (in Formula (1), Z 1 is a ring including at least two carbon atoms, and indicates a five-membered ring, a six-membered ring, or a condensed ring including at least any one of the five-membered ring and the six-membered ring, and Z 1 may have a substituent, each of L 1 , L 2 , and L 3 independently indicates a methine group which may have a substituent, n indicates an integer of 0 or greater, Ar 11 indicates an arylene group or a heteroarylene group which may have a substituent, Ar 11 and L 1 may be bonded to each other to form a ring, and the ring formed by bonding Ar 11 and L 1 may have a substituent, each of Ar 12 and Ar 13 independently indicates an aryl group or a heteroaryl group which may have a substituent, and Ar 12 and Ar 13 may be bonded to each other to form a ring, at least one of Ar 11 and Ar 12 ; and Ar 11 and Ar 13 are bonded to each other to form a ring, at least one of Z 1 , Ar 11 , Ar 12 , and Ar 13 has a specific substituent, and the specific substituent is a monovalent substituent including at least one type of atom selected from the group consisting of oxygen atom, sulfur atom, selenium atom, silicon atom, and germanium atom.). 2 . The photoelectric conversion material according to claim 1 , wherein Z 1 is a ring expressed by the following Formula (Z1), (in Formula (Z1), Z 2 is a ring including at least three carbon atoms, and indicates a five-membered ring, a six-membered ring, or a condensed ring including at least any one of the five-membered ring and the six-membered ring, and * indicates a bonding position with L 1 .). 3 . The photoelectric conversion material according to claim 1 , wherein Ar 11 is an arylene group which may have a substituent. 4 . The photoelectric conversion material according to claim 1 , wherein at least one of Ar 11 , Ar 12 , and Ar 13 has the specific substituent. 5 . The photoelectric conversion material according to claim 1 , wherein the compound (A) is a compound (a1) expressed by the following Formula (2), (in Formula (2), Z 1 is a ring including at least two carbon atoms, and indicates a five-membered ring, a six-membered ring, or a condensed ring including at least any one of the five-membered ring and the six-membered ring, and Z 1 may have a substituent, each of L 1 , L 2 , and L 3 independently indicates a methine group which may have a substituent, n indicates an integer of 0 or greater, each of R 21 to R 26 independently indicates a hydrogen atom or a substituent, and R 22 and R 23 ; R 23 and R 24 ; R 25 and R 26 ; and R 21 and R 26 may be respectively bonded to each other to form a ring, m indicates 0 or 1, each of Ar 12 and Ar 13 independently indicates an aryl group or a heteroaryl group which may have a substituent, and Ar 12 and Ar 13 may be bonded to each other to form a ring, at least one of Ar 12 and Ar 13 is bonded to any of R 21 to R 26 via Xa, which is a single bond or a divalent group, to form a ring, Xa indicates an oxygen atom, a sulfur atom, an alkylene group, a silylene group, an alkenylene group, a cycloalkylene group, a cycloalkenylene group, an arylene group, a heteroarylene group, or —NR a — (R a indicates a hydrogen atom or a substituent), and Xa may have a substituent, and at least one of the following (i) and (ii) is satisfied: (i) at least one of Ar 12 and Ar 13 has the specific substituent, and (ii) at least one of R 21 to R 26 is the specific substituent.). 6 . The photoelectric conversion material according to claim 1 , wherein n is 0. 7 . The photoelectric conversion material according to claim 5 , wherein the compound (A) is a compound (a2) expressed by the following Formula (3), (in Formula (3), each of Rz 1 to Rz 4 independently indicates a hydrogen atom or a substituent, and Rz 1 and Rz 2 ; Rz 2 and Rz 3 ; and Rz 3 and Rz 4 may be respectively bonded to each other to form a ring, each of R 21 , R 22 , R 23 , R 25 , and R 26 independently indicates a hydrogen atom or a substituent, and R 22 , and R 23 ; R 25 and R 26 ; and R 21 and R 26 may be respectively bonded to each other to form a ring, each of R 1a and R 1b independently indicates a hydrogen atom or a substituent, and R 1a and R 1b may be bonded to each other to form a ring, each of R 31 to R 35 independently indicates a hydrogen atom or a substituent, and R 31 and R 32 ; R 32 and R 33 ; R 33 and R 34 ; and R 34 and R 35 may be respectively bonded to each other to form a ring, each of R 36 to R 39 independently indicates a hydrogen atom or a substituent, and R 36 and R 37 ; R 37 and R 38 ; and R 38 and R 39 may be respectively bonded to each other to form a ring, and at least one of the following (i) and (ii) is satisfied: (i) at least one of R 31 and R 39 is the specific substituent, and (ii) at least one of R 21 , R 22 , R 23 , R 25 , and R 26 is the specific substituent.). 8 . The photoelectric conversion material according to claim 7 , wherein at least one of R 33 and R 38 is the specific substituent, and at least one type of atom selected from the group consisting of oxygen atom, sulfur atom, selenium atom, silicon atom, and germanium atom included in the specific substituent is directly bonded to a carbon atom to which R 33 or R 38 is bonded. 9 . A photoelectric conversion element comprising, in this order: a conductive film; a photoelectric conversion film containing the photoelectric conversion material according to claim 1 ; and a transparent conductive film. 10 . The photoelectric conversion element according to claim 9 , wherein the photoelectric conversion film further contains an n-type organic semiconductor. 11 . The photoelectric conversion element according to claim 10 , wherein the n-type organic semiconductor includes fullerenes selected from the group consisting of fullerenes and derivatives thereof. 12 . The photoelectric conversion element according to claim 11 , wherein the content of the fullerenes with respect to the total content of the photoelectric conversion material and the fullerenes (=film thickness of fullerenes in terms of single layer/(film thickness of photoelectric conversion material in terms of single layer+film thickness of fullerenes in terms of single layer)) is 50 vol % or greater. 13 . The photoelectric conversion element according to claim 9 , wherein a charge blocking layer is disposed between the conductive film and the transparent conductive film. 14 . The photoelectric conversion element according to claim 13 , wherein the charge blocking layer is an electron blocking layer, and the electron blocking layer contains a compound expressed by the following Formula (EB-1), (in Formula (EB-1), each of A 11 and A 12 indepe
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