# US 10,312,395 B2 · Luminescent solar concentrator comprising disubstituted benzoheterodiazole compounds

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- Number: US 10,312,395 B2
- Document ID: US10312395B2
- Status: Granted
- Kind: B2
- Application number: 15/514,393
- Filed: 2015-09-24
- Published: 2017-08-31
- Granted: 2019-06-04
- Earliest claimed: 2014-09-25
- Assignees: ENI S.p.A.
- Applicants: ENI S.p.A.
- Inventors: Luigi Abbondanza; Antonio Alfonso Proto; Giuliana Schimperna; Liliana Gila
- Web page: https://patentgrep.com/patent/US10312395B2

## CPC

- H10F 77/45: Wavelength conversion means, e.g. by using luminescent material, fluorescent concentrators or up-conversion arrangements
- C07D 413/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C09K 11/06: containing organic luminescent materials
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1048: with oxygen
- C09K 2211/1051: with sulfur
- C09K 2211/1092: containing sulfur as the only heteroatom
- Y02E 10/52: PV systems with concentrators
- H10F: INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Luminescent solar concentrator (LSC) comprising at least one disubstituted benzoheterodiazole compound of general formula (I), in which: —Z represents a sulfur atom, an oxygen atom, a selenium atom; or an NR6 group in which R6 is selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, or from optionally substituted aryl groups; —R1, R2 and R3, which are the same or different, represent a hydrogen atom; or are selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, optionally containing heteroatoms, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted linear or branched C1-C20, preferably C1-C8, alkoxyl groups, optionally substituted phenoxyl groups, or —COOR7 groups or —OCOR7 groups in which R7 is selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, or is a cyano group, provided that when the substituents R1 represents a hydrogen atom, at least one of the substituents R2 and R3 represents an optionally substituted aryl group or an optionally substituted phenoxyl group; —or R1 and R2, can optionally be linked together so as to form, together with the carbon atoms to which they are linked, a saturated, unsaturated or aromatic cyclic ring or a polycyclic system containing from 3 to 14 carbon atoms, preferably from 4 to 6 carbon atoms, optionally containing one or more heteroatoms such as, for example, oxygen, sulfur, nitrogen, silicon, phosphorus, selenium; —or R2 and R3 can optionally be linked together so as to form, together with the carbon atoms to which they are linked, a saturated, unsaturated or aromatic cyclic ring or a polycyclic system containing from 3 to 14 carbon atoms, preferably from 4 to 6 carbon atoms, optionally containing one or more heteroatoms such as, for example, oxygen, sulfur, nitrogen, silicon, phosphorus, selenium; —R4 and R5, which are the same or different, represent a hydrogen atom; or are selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, optionally containing heteroatoms, optionally substituted cycloalkyl groups, optionally substituted aryl groups, optionally substituted linear or branched C1-C20, preferably C1-C8, alkoxyl groups, —COOR7 groups or —OCOR7 groups in which R7 is selected from linear or branched C1-C20, preferably C1-C8, alkyl groups, or is a cyano group; or R4 and R5, can optionally be linked together so as to form, together with the carbon atoms to which they are linked, a saturated, unsaturated, or aromatic cyclic ring or a polycyclic system containing from 3 to 14 carbon atoms, preferably from 4 to 6 carbon atoms, containing one or more heteroatoms such as, for example, sulfur, nitrogen, silicon, phosphorus, selenium.

## Claims

### Claim 1

Luminescent solar concentrator comprising at least one disubstituted benzoheterodiazole compound of general formula (I):
in which:
Z represents a sulfur atom, an oxygen atom, a selenium atom, or an NR6 group in which R6 is selected from: i) linear or branched C1-C20 alkyl groups, or ii) optionally substituted-aryl groups;
R1, R2 and R3, which are the same or different, represent a hydrogen atom, except R1, R2 and R3 cannot all represent hydrogen, or are selected from: i) linear or branched C1-C20 alkyl groups optionally containing heteroatoms, ii) optionally substituted cycloalkyl groups, iii) optionally substituted aryl groups, iv) optionally substituted linear or branched C1-C20 alkoxyl groups, v) optionally substituted phenoxyl groups, or vi) —COOR7 groups or —OCOR7 groups in which R7 is selected from linear or branched C1-C20-alkyl groups, or R7 is a cyano group, and provided that when the substituents R1 represents a hydrogen atom, at least one of the substituents R2 and R3 represents an optionally substituted phenoxyl group;
R1 and R2 can optionally be linked together so as to form, together with carbon atoms to which they are linked, a saturated, unsaturated or aromatic cyclic ring, or a polycyclic system containing from 3 to 14 carbon atoms, the cyclic ring or polycyclic system optionally containing one or more heteroatoms;
R2 and R3 can optionally be linked together so as to form, together with carbon atoms to which they are linked, a saturated, unsaturated or aromatic cyclic ring, or a polycyclic system containing from 3 to 14 carbon atoms, the cyclic ring or polycyclic system optionally containing one or more heteroatoms;
R4 and R5, which are the same or different, represent a hydrogen atom, or are selected from: i) linear or branched C1-C20 alkyl groups optionally containing heteroatoms, ii) optionally substituted cycloalkyl groups, iii) optionally substituted aryl groups, iv) optionally substituted linear or branched C1-C20 alkoxyl groups, or v) —COOR7 groups or —OCOR7 groups in which R7 is selected from linear or branched C1-C20 alkyl groups, or R7 is a cyano group;
R4 and R5 can optionally be linked together so as to form, together with carbon atoms to which they are linked, a saturated, unsaturated, or aromatic cyclic ring, or a polycyclic system containing from 3 to 14 carbon atoms, the cyclic ring or polycyclic system optionally containing one or more heteroatoms.

### Claim 2 (depends on 1)

Luminescent solar concentrator according to claim 1, wherein in said general formula (I):
Z represents a sulfur atom or an oxygen atom;
R1 are selected from optionally substituted aryl groups or optionally substituted phenoxyl groups;
R2 and R3, which are the same or different, represent a hydrogen atom, or are selected from: i) linear or branched C1-C20 alkyl groups, ii) optionally substituted aryl groups, or iii) optionally substituted phenoxyl groups;
R4 and R5, which are the same, represent a hydrogen atom.

### Claim 3 (depends on 1)

Photovoltaic device comprising at least one photovoltaic cell, and at least one luminescent solar concentrator including at least a disubstituted benzoheterodiazole compound of general formula (I) according to claim 1.

### Claim 4

Luminescent solar concentrator comprising at least one disubstituted benzoheterodiazole compound of general formula (I):
in which:
Z represents a sulfur atom, an oxygen atom, a selenium atom, or an NR6 group in which R6 is selected from: i) linear or branched C1-C8 alkyl groups, or ii) optionally substituted-aryl groups;
R1, R2 and R3, which are the same or different, represent a hydrogen atom, except R1, R2 and R3 cannot all represent hydrogen, or are selected from: i) linear or branched C1-C8 alkyl groups optionally containing heteroatoms, ii) optionally substituted cycloalkyl groups, iii) optionally substituted aryl groups, iv) optionally substituted linear or branched C1-C8 alkoxyl groups, v) optionally substituted phenoxyl groups, or vi) —COOR7 groups or —OCOR7 groups in which R7 is selected from linear or branched C1-C8-alkyl groups, or R7 is a cyano group, and provided that when the substituents R1 represents a hydrogen atom, at least one of the substituents R2 and R3 represents an optionally substituted phenoxyl group;
R1 and R2 can optionally be linked together so as to form, together with carbon atoms to which they are linked, a saturated, unsaturated or aromatic cyclic ring, or a polycyclic system containing from 4 to 6 carbon atoms, the cyclic ring or polycyclic system optionally containing one or more heteroatoms;
R2 and R3 can optionally be linked together so as to form, together with carbon atoms to which they are linked, a saturated, unsaturated or aromatic cyclic ring, or a polycyclic system containing from 4 to 6 carbon atoms, the cyclic ring or polycyclic system optionally containing one or more heteroatoms;
R4 and R5, which are the same or different, represent a hydrogen atom, or are selected from: i) linear or branched C1-C8 alkyl groups optionally containing heteroatoms, ii) optionally substituted cycloalkyl groups, iii) optionally substituted aryl groups, iv) optionally substituted linear or branched C1-C8 alkoxyl groups, or v) —COOR7 groups or —OCOR7 groups in which R7 is selected from linear or branched C1-C8 alkyl groups, or R7 is a cyano group;
R4 and R5 can optionally be linked together so as to form, together with carbon atoms to which they are linked, a saturated, unsaturated, or aromatic cyclic ring, or a polycyclic system containing from 4 to 6 carbon atoms, the cyclic ring or polycyclic system optionally containing one or more heteroatoms.

### Claim 5 (depends on 4)

Luminescent solar concentrator according to claim 4, wherein in said general formula (I):
Z represents a sulfur atom or an oxygen atom;
R1, which are the same, represent a hydrogen atom, or represent optionally substituted aryl groups that are selected from phenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2,6-di-iso-propylphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, or 2,4-dimethoxyphenyl;
R2 and R3, which are the same or different, represent a hydrogen atom, or are selected from: i) linear or branched C1-C8 alkyl groups, ii) optionally substituted aryl groups selected from phenyl, 2,6-dimethylphenyl, or 2-phenoxyphenyl, or iii) optionally substituted phenoxyl groups;
R4 and R5, which are the same, represent a hydrogen atom.

### Claim 6 (depends on 5)

Luminescent solar concentrator according to claim 5 wherein R2 and R3 are both methyl groups.

### Claim 7 (depends on 5)

Photovoltaic device comprising at least one photovoltaic cell, and at least one luminescent solar concentrator including at least a disubstituted benzoheterodiazole compound of general formula (I) according to claim 5.