Picene derivative, photoelectric material, and photoelectric device
The present invention provides: a p-type organic semiconductor material which is able to be produced easily, while having high planarity in a polymer skeleton; and a photoelectric conversion layer, a photoelectric conversion element and an organic thin film solar cell, each of which uses this p-type organic semiconductor material and has high photoelectric conversion efficiency. The present invention specifically provides: a picene derivative which has at least one constituent unit represented by general formula (1); and a photoelectric conversion element which contains (A) the picene derivative serving as a p-type organic semiconductor material and (B) an n-type organic semiconductor material. The details of general formula (1) are as set forth in the description.
1. A picene derivative comprising 2 to 100 constitutional units represented by general formula (1):
wherein A 1 and A 2 each independently represent a monocyclic ring; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxy group, a carboxyl group, a thiol group, —SiR 7 R 8 R 9 , —NR 10 R 11 , or an optionally substituted hydrocarbon group, provided that at least one of R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is not hydrogen; and R 7 , R 8 , R 9 , R 10 , and R 11 each independently represent a hydrogen atom or an optionally substituted hydrocarbon group.
2. The picene derivative according to claim 1 , wherein said picene derivative comprises 2 to 100 constitutional units represented by the above formula (1) and at least one constitutional unit selected from the constitutional units of group Y and group Z:
wherein X 1 and X 4 each represent S, O, or NR 12 ; k represents an integer of 1 to 4; R 12 represents an optionally substituted hydrocarbon group; the hydrogen atom of the constitutional unit of group Y is optionally replaced with a halogen atom, a cyano group, a nitro group, a hydroxy group, a carboxyl group, a thiol group, —NR 13 R 14 , an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group; and R 13 and R 14 each represent an optionally substituted hydrocarbon group; and
wherein X 2 represents S or NR 15 ; X 3 represents S, NR 15 , CR 16 R 17 , or SiR 16 R 17 ; X 5 represents S, O, or NR 15 ; R 15 , R 16 , and R 17 each represent an optionally substituted hydrocarbon group; the hydrogen atom of the constitutional unit of group Z is optionally replaced with a halogen atom, a cyano group, a nitro group, a hydroxy group, a carboxyl group, a thiol group, —NR 18 R 19 , an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group; and R 16 and R 19 each represent an optionally substituted hydrocarbon group.
3. A photoelectric material comprising (A) the picene derivative according to claim 2 as a p-type organic semiconductor material and (B) an n-type organic semiconductor material.
4. The picene derivative according to claim 1 , comprising 2 to 100 constitutional unit represented by general formula (2):
wherein A 1 , A 2 , R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are as defined in claim 1 ; at least one R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is not hydrogen; Y 1 and Y 2 each represent a single bond or a combination of 1 to 5 groups selected from (Y-1) to (Y-8) linked to each other; Z 1 represents a single bond or a group selected form (Z-1) to (Z-21); and n represents an integer of 1 to 1000:
wherein X 1 and X 4 each represent S, O, or NR 12 ; k represents an integer 1 to 4; R 12 represents an optionally substituted hydrocarbon group; the hydrogen atom of the groups (Y-1) to (Y-4) and (Y-6) to (Y-8) is optionally replaced with a halogen atom, a cyano group, a nitro group, a hydroxy group, a carboxyl group, a thiol group, —NR 13 R 14 , an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group; and R 13 and R 14 each represent an optionally substituted hydrocarbon group:
wherein X 2 represents S or NR 15 , X 3 represents S, NR 15 , CR 16 R 17 , or SiR 16 R 17 ; X 5 represents S, O, or NR 15 ; R 15 , R 16 , and R 17 each represent an optionally substituted hydrocarbon group; the hydrogen atom of the groups (Z-1) to (Z-21) is optionally replaced with a halogen atom, a cyano group, a nitro group, a hydroxy group, a carboxyl group, a thiol group, —NR 18 R 19 , an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group; and R 18 and R 19 each represent an optionally substituted hydrocarbon group.
5. A photoelectric material comprising (A) the picene derivative according to claim 4 as a p-type organic semiconductor material and (B) an n-type organic semiconductor material.
6. A photoelectric material comprising (A) the picene derivative according to claim 1 as a p-type organic semiconductor material and (B) an n-type organic semiconductor material.
7. A photoelectric layer obtained by film formation using the photoelectric material according to claim 6 .
8. A photoelectric device comprising the photoelectric layer according to claim 7 .
9. An organic thin film solar cell comprising the photoelectric device according to claim 8 .