PHOTOELECTRIC CONVERSION ELEMENT, IMAGING ELEMENT, OPTICAL SENSOR, AND COMPOUND

Abstract

A photoelectric conversion element having a high photoelectric conversion efficiency in a visible light region (particularly, a wavelength range of 450 to 650 nm) even after being subjected to heat treatment (annealing) is provided. In addition, an imaging element, an optical sensor, and a compound are provided.

Description

Claims

1. A photoelectric conversion element comprising, in the following order: a conductive film;a photoelectric conversion film; anda transparent conductive film,wherein the photoelectric conversion film at least contains a compound represented by Formula (1), in Formula (1), A1 represents a group represented by any one of Formula (1A) or Formula (2A),D1 represents a substituent having a nitrogen atom and an aromatic ring,R1 represents a hydrogen atom or a substituent,in Formula (1A), Y11 and Y12 each independently represent an oxygen atom, a sulfur atom, ═C(CN)2, =C(COR11)2, ═C(SO2R11)2, =C(SOR11)2, =C(CN)(COR11), ═C(CN)(SO2R11), =C(CN)(SOR11), =C(COR11)(SO2R11), =C(COR11)(SOR11), or =C(SO2R11)(SOR11), R11 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, or a heteroaryl group which may have a substituent, where Y11 and Y12 are not the same as each other,one of X11 or X12 represents a sulfur atom, an oxygen atom, a selenium atom, or NR12, and the other represents a nitrogen atom or —CRx═, X13 represents —CRx═ or a nitrogen atom, R12 represents a hydrogen atom or a substituent, Rx represents a hydrogen atom or a substituent, in a case where X11 and X13 each represent —CRx═, Rx’s may be bonded to each other to form a ring, in a case where X12 and X13 each represent —CRx═, Rx’s may be bonded to each other to form a ring,a dotted line specified in Formula (1A) represents that a ring structure having X11 to X13 and carbon atoms respectively adjacent to X11 and X13 in Formula (1A) as ring member atoms forms a resonance structure,* represents a bonding position,in Formula (2A), Y21 and Y22 each independently represent an oxygen atom, a sulfur atom, ═C(CN)2, =C(COR21)2, ═C(SO2R21)2, =C(SOR21)2, =C(CN)(COR21), ═C(CN)(SO2R21), =C(CN)(SOR21), =C(COR21)(SO2R21), =C(COR21)(SOR21), or =C(SO2R21)(SOR21), R21 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, or a heteroaryl group which may have a substituent, where Y21 and Y22 are not the same as each other,B represents a 5- or 6-membered monocyclic aromatic ring which may have a substituent,one of X21 or X22 represents a sulfur atom, an oxygen atom, a selenium atom, or NR22, and the other represents a nitrogen atom or -CRY=, X23 represents -CRY= or a nitrogen atom, R22 represents a hydrogen atom or a substituent, RY represents a hydrogen atom or a substituent, in a case where X21 and X23 each represent -CRY=, Ry’s may be bonded to each other to form a ring, in a case where X22 and X23 each represent -CRY=, Ry’s may be bonded to each other to form a ring,a dotted line specified in Formula (2A) represents that a ring structure having X21 to X23 and carbon atoms respectively adjacent to X21 and X23 in Formula (2A) as ring member atoms forms a resonance structure, and* represents a bonding position.

2. The photoelectric conversion element according to claim 1, wherein one of Y11 or Y12 represents an oxygen atom or a sulfur atom, andone of Y21 or Y22 represents an oxygen atom or a sulfur atom.

3. The photoelectric conversion element according to claim 1, wherein one of Y11 or Y12 represents ═C(CN)2, andone of Y21 or Y22 represents ═C(CN)2.

4. The photoelectric conversion element according to claim 1, wherein A1 represents a group represented by Formula (1Aa-1), in Formula (1Aa-1), Rx represents a hydrogen atom or a substituent.

5. The photoelectric conversion element according to claim 1, wherein D1 represents a group represented by any one of Formula (1D) or Formula (2D), in Formula (1D), * represents a bonding position,Ard11 represents an aromatic ring containing two or more carbon atoms, which may have a substituent,Rd11 and Rd12 each independently represent an aromatic ring group or -C(RL11)(RL12)(RL13), which may have a substituent, RL11 to RL13 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL11 to RL13 may be bonded to each other to form a ring,Rd13 represents a hydrogen atom or a substituent,in Formula (2D), * represents a bonding position,Ard21 represents an aromatic ring containing two or more carbon atoms, which may have a substituent,Rd22 represents an aromatic ring group which may have a substituent or -C(RL21)(RL22)(RL23), RL21 to RL23 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL21 to RL23 may be bonded to each other to form a ring,Xd21 represents a sulfur atom, an oxygen atom, or -C(RL24)(RL25)-, RL24 and RL25 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL24 and RL25 may be bonded to each other to form a ring, andRd23 represents a hydrogen atom or a substituent.

6. The photoelectric conversion element according to claim 5, wherein D1 represents a group represented by Formula (1D).

7. The photoelectric conversion element according to claim 6, wherein the group represented by Formula (1D) represents a group represented by Formula (3D), in Formula (3D), * represents a bonding position,Rd11 and Rd12 each independently represent an aromatic ring group or -C(RL11)(RL12)(RL13), which may have a substituent, RL11 to RL13 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL11 to RL13 may be bonded to each other to form a ring,Rd13 represents a hydrogen atom or a substituent,Ed31 to Ed34 each independently represent a nitrogen atom or -CRE31=, RE31 represents a hydrogen atom or a substituent, and in a case where a plurality of RE31′s exist, RE31′s may be bonded to each other to form a ring.

8. The photoelectric conversion element according to claim 6, wherein the group represented by Formula (1D) represents a group represented by Formula (4D), in Formula (4D), * represents a bonding position,Rd11 and Rd12 each independently represent an aromatic ring group or -C(RL11)(RL12)(RL13), which may have a substituent, RL11 to RL13 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL11 to RL13 may be bonded to each other to form a ring,Rdl3, Rd44, and Rd45 each independently represent a hydrogen atom or a substituent, and Rd44 and Rd45 may be bonded to each other to form a ring.

9. The photoelectric conversion element according to claim 6, wherein the group represented by Formula (1D) is a group represented by Formula (5D), in Formula (5D), * represents a bonding position,Rd11 and Rd12 each independently represent an aromatic ring group or -C(RL11)(RL12)(RL13), which may have a substituent, RL11 to RL13 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL11 to RL13 may be bonded to each other to form a ring,Rd13 Rd54, and Rd55 each independently represent a hydrogen atom or a substituent, Rd54 and Rd55 may be bonded to each other to form a ring,Ed51 and Ed52 each independently represent a nitrogen atom or -CRE51=, and RE51 represents a hydrogen atom or a substituent.

10. The photoelectric conversion element according to claim 5, wherein structures of Rd11 and Rd12 are different from each other.

11. The photoelectric conversion element according to claim 5, wherein one of Rd11 or Rd12 represents an alkyl group which may have a substituent, and the other represents a group represented by Formula (X), in Formula (X), * represents a bonding position, C1 represents a monocyclic aromatic ring containing at least two carbon atoms, which may have a substituent other than Rd1, and Rd1 represents an alkyl group which may have a substituent, a silyl group which may have a substituent, an alkoxy group which may have a substituent, an alkylthio group which may have a substituent, a cyano group, a halogen atom, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, an alkenyl group which may have a substituent, or an alkynyl group which may have a substituent.

12. The photoelectric conversion element according to claim 11, wherein the group represented by Formula (X) represents a group represented by Formula (ZB), in Formula (ZB), T1 to T3 each independently represent —CRe12═ or a nitrogen atom, Re12 represents a hydrogen atom or a substituent, Rf3 and Rf4 each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent, and * represents a bonding position.

13. The photoelectric conversion element according to claim 5, wherein D1 represents a group represented by Formula (2D), andthe group represented by Formula (2D) represents a group represented by Formula (6D), in Formula (6D), * represents a bonding position,Rd22 represents an aromatic ring group which may have a substituent or -C(RL21)(RL22)(RL23), RL21 to RL23 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL21 to RL23 may be bonded to each other to form a ring,Xd21 represents a sulfur atom, an oxygen atom, or -C(RL24)(RL25)-, RL24 and RL25 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL24 and RL25 may be bonded to each other to form a ring,Rd23 and Rd61 to Rd64 each independently represent a hydrogen atom or a substituent, and Rd61 to Rd64 may be bonded to each other to form a ring.

14. The photoelectric conversion element according to claim 13, wherein Formula (6D) satisfies at least one or more following requirements,a requirement X1: Rd22 represents an aromatic ring group which may have a substituent,a requirement X2: Xd21 represents -C(RL24)(RL25)-, and RL24 and RL25 are bonded to each other to form a ring, anda requirement X3: any one or more of Rd61 and Rd62, Rd62 and Rd63, and Rd63 and Rd64 are bonded to each other to form a ring.

15. The photoelectric conversion element according to claim 1, wherein the photoelectric conversion film further contains a n-type semiconductor.

16. The photoelectric conversion element according to claim 15, wherein the n-type semiconductor includes fullerenes selected from the group consisting of a fullerene and a derivative thereof.

17. The photoelectric conversion element according to claim 1, wherein the photoelectric conversion film further contains a p-type semiconductor.

18. The photoelectric conversion element according to claim 1, further comprising one or more interlayers between the conductive film and the transparent conductive film, in addition to the photoelectric conversion film.

19. An imaging element comprising the photoelectric conversion element according to claim 1.

20. An optical sensor comprising the photoelectric conversion element according to claim 1.

21. A compound represented by Formula (1), in Formula (1), A1 represents a group represented by any one of Formula (1A) or Formula (2A),D1 represents a substituent having a nitrogen atom and an aromatic ring,R1 represents a hydrogen atom or a substituent,in Formula (1A), Y11 and Y12 each independently represent an oxygen atom, a sulfur atom, ═C(CN)2, =C(COR11)2, ═C(SO2R11)2, =C(SOR11)2, =C(CN)(COR11), ═C(CN)(SO2R11), =C(CN)(SOR11), =C(COR11)(SO2R11, =C(COR11)(SOR11), or =C(SO2R11)(SOR11), R11 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, or a heteroaryl group which may have a substituent, where Y11 and Y12 are not the same as each other,one of X11 or X12 represents a sulfur atom, an oxygen atom, a selenium atom, or NR12, and the other represents a nitrogen atom or —CRx═, X13 represents —CRx═ or a nitrogen atom, R12 represents a hydrogen atom or a substituent, Rx represents a hydrogen atom or a substituent, in a case where X11 and X13 each represent —CRx═, Rx’s may be bonded to each other to form a ring, in a case where X12 and X13 each represent —CRx═, Rx’s may be bonded to each other to form a ring,a dotted line specified in Formula (1A) represents that a ring structure having X11 to X13 and carbon atoms respectively adjacent to X11 and X13 in Formula (1A) as ring member atoms forms a resonance structure,* represents a bonding position,in Formula (2A), Y21 and Y22 each independently represent an oxygen atom, a sulfur atom, ═C(CN)2, =C(COR21)2, ═C(SO2R21)2, =C(SOR21)2, =C(CN)(COR21), ═C(CN)(SO2R21), =C(CN)(SOR21), =C(COR21)(SO2R21), =C(COR21)(SOR21), or =C(SO2R21)(SOR21), R21 each independently represents a hydrogen atom, a hydrocarbon group which may have a substituent, or a heteroaryl group which may have a substituent, where Y21 and Y22 are not the same as each other,B represents a 5- or 6-membered monocyclic aromatic ring which may have a substituent,one of X21 or X22 represents a sulfur atom, an oxygen atom, a selenium atom, or NR22, and the other represents a nitrogen atom or -CRY=, X23 represents -CRY= or a nitrogen atom, R22 represents a hydrogen atom or a substituent, Ry represents a hydrogen atom or a substituent, in a case where X21 and X23 each represent —CRy═, Ry’s may be bonded to each other to form a ring, in a case where X22 and X23 each represent -CRY=, Ry’s may be bonded to each other to form a ring,a dotted line specified in Formula (2A) represents that a ring structure having X21 to X23 and carbon atoms respectively adjacent to X21 and X23 in Formula (2A) as ring member atoms forms a resonance structure, and* represents a bonding position.

22. The compound according to claim 21, wherein one of Y11 or Y12 represents an oxygen atom or a sulfur atom, andone of Y21 or Y22 represents an oxygen atom or a sulfur atom.

23. The compound according to claim 21, wherein one of Y11 or Y12 represents ═C(CN)2, andone of Y21 or Y22 represents ═C(CN)2.

24. The compound according to claim 21, wherein A1 represents a group represented by Formula (1Aa-1), in Formula (1Aa-1), Rx represents a hydrogen atom or a substituent.

25. The compound according to claim 21, wherein D1 represents a group represented by any one of Formula (1D) or Formula (2D), in Formula (1D), * represents a bonding position,Ard11 represents an aromatic ring containing two or more carbon atoms, which may have a substituent,Rd11 and Rd12 each independently represent an aromatic ring group or -C(RL11)(RL12)(RL13), which may have a substituent, RL11 to RL13 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL11 to RL13 may be bonded to each other to form a ring,Rd13 represents a hydrogen atom or a substituent,in Formula (2D), * represents a bonding position,Ard21 represents an aromatic ring containing two or more carbon atoms, which may have a substituent,Rd22 represents an aromatic ring group which may have a substituent or -C(RL21)(RL22)(RL23), RL21 to RL23 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL21 to RL23 may be bonded to each other to form a ring,Xd21 represents a sulfur atom, an oxygen atom, or -C(RL24)(RL25)-, RL24 and RL25 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL24 and RL25 may be bonded to each other to form a ring,Rd23 represents a hydrogen atom or a substituent.

26. The compound according to claim 25, wherein D1 represents a group represented by Formula (1D).

27. The compound according to claim 26, wherein the group represented by Formula (1D) represents a group represented by Formula (3D), in Formula (3D), * represents a bonding position,Rd11 and Rd12 each independently represent an aromatic ring group or -C(RL11)(RL12)(RL13), which may have a substituent, RL11 to RL13 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL11 to RL13 may be bonded to each other to form a ring,Rd13 represents a hydrogen atom or a substituent,Ed31 to Ed34 each independently represent a nitrogen atom or -CRE31=, RE31 represents a hydrogen atom or a substituent, and in a case where a plurality of RE31′s exist, RE31′s may be bonded to each other to form a ring.

28. The compound according to claim 26, wherein the group represented by Formula (1D) represents a group represented by Formula (4D), in Formula (4D), * represents a bonding position,Rd11 and Rd12 each independently represent an aromatic ring group or -C(RL11)(RL12)(RL13), which may have a substituent, RL11 to RL13 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL11 to RL13 may be bonded to each other to form a ring,Rd13, Rd44, and Rd45 each independently represent a hydrogen atom or a substituent, and Rd44 and Rd45 may be bonded to each other to form a ring.

29. The compound according to claim 26, wherein the group represented by Formula (1D) is a group represented by Formula (5D), in Formula (5D), * represents a bonding position,Rd11 and Rd12 each independently represent an aromatic ring group or -C(RL11)(RL12)(RL13), which may have a substituent, RL11 to RL13 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL11 to RL13 may be bonded to each other to form a ring,R43 Rd54, and Rd55 each independently represent a hydrogen atom or a substituent, Rd54 and Rd55 may be bonded to each other to form a ring,Ed51 and Ed52 each independently represent a nitrogen atom or -CRE51=, and RE51 represents a hydrogen atom or a substituent.

30. The compound according to claim 25, wherein structures of Rd11 and Rd12 are different from each other.

31. The compound according to claim 25, wherein one of Rd11 or Rd12 represents an alkyl group which may have a substituent, and the other represents a group represented by Formula (X), in Formula (X), * represents a bonding position, C1 represents a monocyclic aromatic ring containing at least two carbon atoms, which may have a substituent other than Rd1, and Rd1 represents an alkyl group which may have a substituent, a silyl group which may have a substituent, an alkoxy group which may have a substituent, an alkylthio group which may have a substituent, a cyano group, a halogen atom, an aryl group which may have a substituent, a heteroaryl group which may have a substituent, an alkenyl group which may have a substituent, or an alkynyl group which may have a substituent.

32. The compound according to claim 31, wherein the group represented by Formula (X) represents a group represented by Formula (ZB), in Formula (ZB), T1 to T3 each independently represent —CRe12═ or a nitrogen atom, Re12 represents a hydrogen atom or a substituent, Rf3 and Rf4 each independently represent an alkyl group which may have a substituent, an aryl group which may have a substituent, or a heteroaryl group which may have a substituent, and * represents a bonding position.

33. The compound according to claim 25, wherein D1 represents a group represented by Formula (2D), andthe group represented by Formula (2D) represents a group represented by Formula (6D), in Formula (6D), * represents a bonding position,Rd22 represents an aromatic ring group which may have a substituent or -C(RL21)(RL22)(RL23), RL21 to RL23 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL21 to RL23 may be bonded to each other to form a ring,Xd21 represents a sulfur atom, an oxygen atom, or -C(RL24)(RL25)-, RL24 and RL25 each independently represent a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent, RL24 and RL25 may be bonded to each other to form a ring,Rd23 and Rd61 to Rd64 each independently represent a hydrogen atom or a substituent, and Rd61 to Rd64 may be bonded to each other to form a ring.

34. The compound according to claim 33, wherein Formula (6D) satisfies at least one or more following requirements,a requirement X1: Rd22 represents an aromatic ring group which may have a substituent,a requirement X2: Xd21 represents -C(RL24)(RL25)-, and RL24 and RL25 are bonded to each other to form a ring, anda requirement X3: any one or more of Rd61 and Rd62, Rd62 and Rd63, and Rd63 and Rd64 are bonded to each other to form a ring.