Material for photoelectric conversion element for imaging

Patent metadata

Field	Value
Publication number	US-12426503-B2
Application number	US-202118031956-A
Country	US
Kind code	B2
Filing date	Nov 25, 2021
Priority date	Nov 27, 2020
Publication date	Sep 23, 2025
Grant date	Sep 23, 2025

Abstract

Provided are a material that achieves higher sensitivity and higher resolution of a photoelectric conversion element for imaging, and a photoelectric conversion element for imaging using the above material. A material for a photoelectric conversion element for imaging, the material having a structure of the following general formula (1), wherein L each independently represents a single bond, an aromatic hydrocarbon group having 6 to 30 carbon atoms, or the like; “a” represents the number of substitutions, and represents an integer of 1 to 6; Ar1 each independently represents a group represented by the following formula (2); and Ar2 each independently represents an aromatic heterocyclic group having 3 to 30 carbon atoms and containing a nitrogen-containing six-membered cyclic structure, or the like, provided that a group bonded to L is the aromatic heterocyclic group. The ring B represents a heterocyclic ring represented by the formula (2a) and fused with an adjacent ring at any position; “*” in the formula (2) represents a bonding position to L in the formula (1); and X represents O, S, or N—Ar3.

First claim

The invention claimed is:

1. A material for a photoelectric conversion element for imaging, the material being a compound having a structure of the following general formula (1):

wherein L each independently represents a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 4 to 30 carbon atoms and containing a five-membered heterocyclic structure, or a substituted or unsubstituted linked aromatic group in which two to six of any one or more of the aromatic hydrocarbon group or the aromatic heterocyclic group are linked;
“a” represents the number of substitutions, and represents an integer of 1 to 6;
Ar 1 each independently represents a group represented by the following formula (2); and
Ar 2 each independently represents a substituted or unsubstituted aromatic heterocyclic group having 3 to 30 carbon atoms and containing a nitrogen-containing six-membered cyclic structure, or a substituted or unsubstituted linked aromatic group which contains at least one of the aromatic heterocyclic group and in which two to seven of any one or more of the aromatic heterocyclic group or an aromatic hydrocarbon group having 6 to 30 carbon atoms are linked, provided that a group bonded to L is the aromatic heterocyclic group,

wherein ring B represents a heterocyclic ring represented by the formula (2a) and fused with an adjacent ring at any position; “*” in the formula (2) represents a bonding position to L in the formula (1); and X represents O, S, or N—Ar 3 ;
Ar 3 each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 4 to 30 carbon atoms and containing a five-membered heterocyclic structure, a substituted or unsubstituted linked aromatic group in which two to six of any one or more of the aromatic hydrocarbon group or the aromatic heterocyclic group are linked, or L-Ar 2 ;
R 1 , R 2 , and R 3 represent a substituent, and each independently represent an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 4 to 30 carbon atoms and containing a five-membered heterocyclic structure, or a substituted or unsubstituted linked aromatic group in which two to six of any one or more of the aromatic hydrocarbon group or the aromatic heterocyclic group are linked; and R 1 , R 2 , and R 3 are optionally bonded to any adjacent substituent to form a ring or form a fused ring with an adjacent ring; and
“c” represents an integer of 0 to 4, “d” represents an integer of 0 to 2, and “e” represents an integer of 0 to 4.

2. The material for a photoelectric conversion element for imaging according to claim 1 , wherein Ar 2 contains at least one substituted or unsubstituted azine skeleton.

3. The material for a photoelectric conversion element for imaging according to claim 2 , wherein Ar 2 contains at least one substituted or unsubstituted pyridine, pyrimidine, or triazine skeleton.

4. The material for a photoelectric conversion element for imaging according to claim 3 , wherein Ar 2 contains at least one substituted or unsubstituted triazine skeleton.

5. The material for a photoelectric conversion element for imaging according to claim 1 , wherein an energy level of highest occupied molecular orbital (HOMO) obtained by structural optimization calculation with a density functional calculation B3LYP/6-31G(d) is −4.5 eV or lower.

6. The material for a photoelectric conversion element for imaging according to claim 5 , wherein an energy level of lowest unoccupied molecular orbital (LUMO) obtained by structural optimization calculation with a density functional calculation B3LYP/6-31G(d) is −2.5 eV or higher.

7. The material for a photoelectric conversion element for imaging according to claim 1 , wherein the material has a hole mobility of 1×10 −6 cm 2 /Vs or more.

8. The material for a photoelectric conversion element for imaging according to claim 1 , wherein when any one of L, the substituent in Ar 2 , Ar 3 , the substituent in Ar 3 , R 1 , R 2 , and R 3 represents the aromatic heterocyclic group having 4 to 30 carbon atoms and containing a five-membered heterocyclic structure, the five-membered heterocyclic structure is a pyrrole ring, a furan ring, or a thiophene ring.

9. The material for a photoelectric conversion element for imaging according to claim 1 , wherein the material for a photoelectric conversion element is amorphous.

10. The material for a photoelectric conversion element for imaging according to claim 1 , wherein the material is used as a hole transport material.

11. A photoelectric conversion element for imaging, comprising a photoelectric conversion layer and an electron blocking layer between two electrodes, wherein at least one layer of the photoelectric conversion layer or the electron blocking layer contains the material for a photoelectric conversion element for imaging according to claim 1 .

12. The photoelectric conversion element for imaging according to claim 11 , wherein the photoelectric conversion layer contains an electron transport material.

13. The photoelectric conversion element for imaging according to claim 11 , wherein the electron blocking layer contains the material for a photoelectric conversion element for imaging.

Assignees

• Nippon Steel Chemical & Mat Co Ltd

Inventors

• Kawada Atsushi
• Inoue Munetomo
• Hayashi Kentaro

Classifications

• C07D487/04

  Ortho-condensed systems · CPC title

• H10K30/86

  Layers having high hole mobility, e.g. hole-transporting layers or electron-blocking layers · CPC title

• H10K30/85

  Layers having high electron mobility, e.g. electron-transporting layers or hole-blocking layers · CPC title

• H10K85/654 Primary

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K39/00

  Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00 · CPC title