Process for preparing a crystalline organic semiconductor material

Patent metadata

Field	Value
Publication number	US-10224485-B2
Application number	US-201515504463-A
Country	US
Kind code	B2
Filing date	Aug 17, 2015
Priority date	Aug 18, 2014
Publication date	Mar 5, 2019
Grant date	Mar 5, 2019

Abstract

Provided are a process for preparing a crystalline organic semiconductor material wherein the conditions of crystallization lead to the formation of crystals at the gas liquid interface having advantageous semiconductor properties, the obtained crystalline organic semiconductor material and the use thereof for the production of organic semiconductor devices, in particular organic field effect transistors and organic solar cells.

First claim

The invention claimed is:

1. A process for preparing a crystalline organic semiconductor material, the process comprising:
(a) providing a solution comprising an organic semiconductor A) in a solvent (L1) or in a solvent mixture comprising a solvent (L1) and a solvent (L2), which is different from the solvent (L1),
wherein the solvent (L1) has
a boiling point at 1013.25 mbar of at least 140° C.,
a viscosity of at least 1.2 mPas at 23° C., and
a surface tension of at least 31.5 mN/m at 20° C.; and

(b) applying dig solution to a surface of a substrate, evaporating of the solvent (L1) or die solvent mixture comprising the solvent (L1) and the solvent (L2), and crystallizing the organic semiconductor A),
wherein the organic semiconductor A) is at least one selected from the group consisting of:
a rylene compound of formula (II.a):

wherein:
n is 1, 2, 3, or 4;
R a and R b are independently hydrogen, an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkadienyl an optionally substituted alkynyl, an optionally substituted cycloalkyl, an optionally substituted bicycloalkyl, an optionally substituted cycloalkenyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, or an optionally substituted heteroaryl; and
R n1 , R n2 , R n3 and R n4 are independently hydrogen, F, Cl, Br, I, CN, hydroxy, mercapto, nitro, cyanato, thiocyanato, formyl, acyl, carboxy, carboxylate, alkylcarbonyloxy, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, sulfo, sulfonate, sulfoamino, sulfamoyl, alkylsulfonyl, arylsulfonyl, amidino,
NE 1 E 2 :
where E 1 and E 2 are each independently hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl, or hetaryl,

an optionally substituted alkyl, an optionally substituted alkoxy, an optionally substituted alkylthio, an optionally substituted (monoalkyl)amino, an optionally substituted (dialkyl)amino, an optionally substituted cycloalkyl, an optionally substituted cycloalkoxy, an optionally substituted cycloalkylthio, an optionally substituted (monocycloalkyl)amino, an optionally substituted (dicycloalkyl)amino, an optionally substituted heterocycloalkyl, an optionally substituted heterocycloalkoxy, an optionally substituted heterocycloalkylthio, an optionally substituted (monoheterocycloalkyl)amino, an optionally substituted (diheterocycloalkyl)amino, an optionally substituted aryl, an optionally substituted aryloxy, an optionally substituted arylthio, an optionally substituted (monoaryl)amino, an optionally substituted (diaryl)amino, an optionally substituted hetaryl, an optionally substituted hetaryloxy, an optionally substituted hetarylthio, an optionally substituted (monohetaryl)amino, or an optionally substituted (dihetaryl)amino;

a compound of formula (II.b)

wherein:
R 1b and R 2b are independently hydrogen, an optionally substituted linear C 1 -C 30 -alkyl, an optionally substituted branched C 3 -C 30 -alkyl, an optionally substituted linear C 2 -C 30 -alkenyl, an optionally substituted branched C 3 -C 30 -alkenyl, an optionally substituted linear C 2 -C 30 -alkynyl, an optionally substituted branched C 4 -C 30 -alkynyl, an optionally substituted cycloalkyl, an optionally substituted aryl, or an optionally substituted hetaryl; and
Y 1b and Y 2b are independently O, S, Se, or NR 3b , where R 3b is independently hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl;

a compound of formula (II.c):

wherein:
R 1c and R 2c are independently hydrogen, an optionally substituted linear C 1 -C 30 -alkyl, an optionally substituted branched C 3 -C 30 -alkyl, an optionally substituted linear C 2 -C 30 -alkenyl, an optionally substituted branched C 3 -C 30 -alkenyl, an optionally substituted linear C 2 -C 30 -alkynyl, an optionally substituted branched C 4 -C 30 -alkynyl, an optionally substituted cycloalkyl, an optionally substituted aryl, or an optionally substituted hetaryl; and
Y 1c , Y 2c and Y 3c are independently O, S, Se, or NR 3c , where R 3c is independently hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl;

a compound of formula (II.d):

wherein:
R 1d and R 2d are independently hydrogen, an optionally substituted linear C 1 -C 30 -alkyl, an optionally substituted branched C 3 -C 30 -alkyl, an optionally substituted linear C 2 -C 30 -alkenyl, an optionally substituted branched C 3 -C 30 -alkenyl, an optionally substituted linear C 2 -C 30 -alkynyl, an optionally substituted branched C 4 -C 30 -alkynyl, an optionally substituted cycloalkyl, an optionally substituted aryl, or an optionally substituted hetaryl; and
Y 1d , Y 2d , Y 3d and Y 4d are independently O, S, Se, or NR 3d , where R 3d is independently hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; and

a compound of formula (II.e):

wherein:
R 1e and R 2e are independently hydrogen, an optionally substituted linear C 1 -C 30 -alkyl, an optionally substituted branched C 3 -C 30 -alkyl, an optionally substituted linear C 2 -C 30 -alkenyl, an optionally substituted branched C 3 -C 30 -alkenyl, an optionally substituted linear C 2 -C 30 -alkynyl, an optionally substituted branched C 4 -C 30 -alkynyl, an optionally substituted cycloalkyl, an optionally substituted aryl, or an optionally substituted hetaryl; and
Y 1e and Y 2e are independently O, S, Se or NR 3e , where R 3e is independently hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl,

wherein the solvent (L1) is at least one selected from the group consisting of a hydroxybenzoic ester, a compound of formula (I.1), a compound of formula (I.2), a compound of formula (I.3), a compound of formula (I.4), and a compound of formula (I.5):

wherein:
X 1 and X 2 are independently *—(C═O)—O—, *—(CH 2 ) m —O—, or *—(CH 2 ) m —O—(C═O)—, where * is a point of linkage to the aliphatic or aromatic carbocycle or heterocycle, and m is 0, 1, or 2; and
R c and R d are independently unbranched or branched C 1 -C 12 -alkyl or C 2 -C 12 -alkenyl, and

wherein the solvent (L2) is at least one compound selected from the group consisting of:
an aliphatic, a cycloaliphatic, or an aromatic hydrocarbon other than a polycyclic hydrocarbon comprising a cycloaliphatic ring;
an aromatic ether;
an open chain aliphatic ether, a polyether, an ether alcohol, or a cyclic ether;
a ketone other than an aromatic aliphatic ketone;
an ester other than an alkyl benzoate, a hydroxybenzoic acid ester, and an alkylene carbonate;
an aliphatic or a cycloaliphatic alcoh

Assignees

• Basf Se

Inventors

• Weitz Thomas
• Vladimirov Ilja
• Chiodo Tiziana
• Seyfried Thomas

Classifications

• Y02E10/549

  Organic PV cells · CPC title

• Y02P70/521

  Cross-Sectional Technologies · mapped topic

• H01L51/4253

  Electricity · mapped topic

• H01L51/0004

  Electricity · mapped topic

• H01L51/0007

  Electricity · mapped topic