Mixtures for producing photoactive layers for organic solar cells and organic photodetectors

Patent metadata

Field	Value
Publication number	US-9368729-B2
Application number	US-201013501018-A
Country	US
Kind code	B2
Filing date	Oct 11, 2010
Priority date	Oct 13, 2009
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

The present invention relates to the use of mixtures which comprise, as components K1), one or more merocyanines selected from the group of the compounds of the general formulae Ia, Ib, Ic, Id, Ie, IIa and IIb, as defined in more detail in the description, as an electron donor or electron acceptor, and, as component K2), one or more compounds which, with respect to component K1), act correspondingly as an electron acceptor or electron donor, for producing photoactive layers for organic solar cells and organic photodetectors, to a process for producing photoactive layers, corresponding solar cells and organic photodetectors, and to mixtures which comprise, as components, one or more compounds of the general formulae Ia, Ib, Ic, Id, Ie, IIa and/or IIb of component K1, as defined in more detail in the description, and one or more compounds of component K2.

First claim

The invention claimed is:

1. A process for producing a photoactive layer, comprising producing a photoactive layer with a mixture comprising a component K1 and a component K2,
wherein:
K1 is of any of general formulae:

K1 is an electron donor or electron acceptor;
each A is independently a bridge consisting of two or three sp 3 -hybridized carbon atoms, in which each carbon atom is optionally substituted by one R 101 substituent each, and in which each carbon atom is optionally benzofused;
each B and C is independently a bridge consisting of two or three carbon atoms, each of which is sp 2 - or sp 3 -hybridized, and each of which is optionally substituted by one R 101 substituent;
each W is independently O, S, N—CN, N—R 110 , C(CN) 2 , C(CO 2 R 110 ) 2 , C(CN)COR 110 , C(CN)CO 2 R 110 , or C(CN)CONR 110 ;
each L is independently a divalent carbocycle or heterocycle, which is optionally singly or multiply fused;
each n is independently 0 or 1;
each X 100 is independently CH, N, or C(CN);
each X 200 is independently C(R 111 ) 2 , O, S, SO 2 , or NR 110 ;
each X 201 is independently CR 111 or an sp 2 -hybridized unsubstituted carbon atom bonded to an sp 2 -hybridized carbon atom of B or C;
each R 100 is independently H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO-alkyl, C 1 -C 6 - alkylene-O—CO—O-alkyl, cycloalkyl, arylalkyl, aryl, OR 110 , SR 110 , hetaryl, halogen, NO 2 , or CN;
each R 101 is independently alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO—alkyl, C 1 -C 6 -alkylene-O—CO—O-alkyl, cycloalkyl, arylalkyl, aryl, or hetaryl;
each R 110 is independently H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO-alkyl, C 1 -C 6 - alkylene-O—CO—O-alkyl, cycloalkyl, arylalkyl, or aryl;
each R 111 is independently H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO-alkyl, C 1 -C 6 - alkylene-O—CO—O-alkyl, cycloalkyl, arylalkyl, aryl, or hetaryl;
each carbon chain of an alkyl or cycloalkyl radical in K1 independently is optionally interrupted by one or two nonadjacent oxygen atoms; and
component K2 is a compound capable of acting as an electron acceptor or electron donor correspondingly with respect to component K1.

2. The process of claim 1 , wherein:
when n is 1, L is a moiety selected from the group consisting of:

each R 102 is independently arylalkyl, aryl, or hetaryl;
each R 112 is independently H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO-alkyl, C 1 -C 6 - alkylene-O—CO—O-alkyl, cycloalkyl, arylalkyl, aryl, OR 110 , or SR 110 ;
each R 113 is independently H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO-alkyl, C 1 -C 6 - alkylene-O—CO—O-alkyl, cycloalkyl, arylalkyl, aryl, hetaryl, NH-aryl, N(aryl) 2 , NHCO-R 101 , or N(CO—R 101 ) 2 ;
each R 114 is independently H, alkyl, partly fluorinated alkyl, partly perfluorinated alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO-alkyl, or C 1 -C 6 -alkylene-O-—CO—O-alkyl;
each R 115 is independently H, alkyl, partly fluorinated alkyl, partly perfluorinated alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO-alkyl, C 1 -C 6 - alkylene-O—CO—O-alkyl, cycloalkyl, arylalkyl, aryl, NHCO-R 101 , or N(CO-R 101 ) 2 ;
each R 116 is independently H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO-alkyl, C 1 -C 6 - alkylene-O—CO—O-alkyl, cycloalkyl, arylalkyl, aryl, CO 2 R 110 , or CN;
each R 117 is independently H, alkyl, C 1 -C 6 -alkylene-COO-alkyl, C 1 -C 6 -alkylene-O—CO-alkyl, C 1 -C 6 - alkylene-O—CO—O-alkyl, cycloalkyl, arylalkyl, aryl, OR 110 , SR 110 halogen, or hetary;
each R 212 is independently H, CN, CONR 110 , or COR 101 ;
each X 202 is independently O, S, or two hydrogen atoms;
* and ** denote attachment to X 100 or W; and
each carbon chain of an alkyl or cycloalkyl radical in L independently is optionally interrupted by one or two nonadjacent oxygen atom.

3. The process of claim 1 , wherein component K2 comprises at least one compound selected from the group consisting of a fullerene, a polycyclic aromatic hydrocarbon, a quinone, a quinodimethane, a quinonediimine, a phthalocyanine, a subphthalocyanine, a porphyrin, a tetraazaporphyrin, a tetrabenzoporphyrin, athiophene, an oligothiophene, a fused thiophene, a thiadiazole, a carbazole, a triarylamine, an indanthrone, a violanthrone, a flavanthones, a fulvalene, a tetrathiafulvalene, a tetraselenafulvalene, a diketopyrrolopyrrole, and a derivative thereof.

4. The process of claim 1 , wherein component K2 comprises a fullerene, a fullerene derivative, or a combination thereof.

5. The process of claim 4 , wherein component K2 comprises a fullerene.

6. The process of claim 5 , wherein component K2 comprises a C60-fullerene of formula k2:

7. The process of claim 1 , wherein:
the component K1 is present in the mixture in a proportion of from 10 to 90% by mass;u
the component K2 is present in the mixture in a proportion of from 90 to 10% by mass; and
the proportions of the components K1 and K2, are based in each case on a total mass of components K1 and K2, add up to 100% by mass.

8. The process of claim 3 , wherein producing the photoactive layer with the mixture comprises depositing the components K1 and K2 on a substrate successively, simultaneously, or in alternating sequence by vacuum sublimation.

9. The process of claim 8 , wherein after depositing the components K1 and K2 the component K1 is present on the substrate in a proportion of from 10 to 90% by mass, and the component K2 is present on the substrate in a proportion of from 90 to 10% by mass, based in each case on a total mass of components K1 and K2.

10. An organic solar cell or organic photodetector, comprising a photoactive layer obtained by a process comprising the process of claim 1 .

11. A mixtur; comprising a component K1 and a component K2,
wherein:
the component K1 is of any of general formulae:

the component K1 is an electron donor or electron acceptor;
each A is independently a bridge consisting of two or three sp 3 -hybridized carbon atoms, in which each carbon atom is optionally substituted by one R 101 substituent each, and in which each carbon atom is optionally benzofused;
each B and C is independently a bridge consisting of two or three carbon atoms, each of which is sp 2 - or sp 3 -hybridized, and each of which is optionally substituted by one R 101 substituent;
each W is independently O, S, N—CN, N—R 110 , C(CN) 2 , C(CO 2 R 110 ) 2 , C(CN)COR 110 , C(CN)CO 2 R 110 , or C(CN)CONR 110 ;

Assignees

• Hwang Jae Hyung
• Erk Peter
• Reichelt Helmut
• Sens Ruediger
• Bruder Ingmar
• Ojala Antti
• Schoeneboom Jan
• Wuerthner Frank
• Buerckstuemmer Hannah
• Tulyakova Elena
• Meerholz Klaus
• Steinmann Vera
• Kronenberg Nils
• Basf Se

Inventors

• Hwang Jae Hyung
• Erk Peter
• Reichelt Helmut
• Sens Ruediger
• Bruder Ingmar
• Ojala Antti
• Schoeneboom Jan
• Wuerthner Frank
• Buerckstuemmer Hannah
• Tulyakova Elena
• Meerholz Klaus
• Steinmann Vera
• Kronenberg Nils

Classifications

• C09B23/105

  two >CH- groups · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K85/652 Primary

  Cyanine dyes · CPC title

• H01L51/0046

  Electricity · mapped topic