Organic semiconductor device and process for its production

Patent metadata

Field	Value
Publication number	US-9543521-B2
Application number	US-201214357014-A
Country	US
Kind code	B2
Filing date	Nov 14, 2012
Priority date	Nov 15, 2011
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

An organic semiconductor device selected from organic diodes, organic field effect transistors, and devices comprising an organic diode and/or organic field effect transistor and a method of producing such a device are provided. The organic semiconductor device comprises at least one semiconducting layer based on a diketopyrrolopyrrole (DPP) polymer. The semiconducting layer may effectively be protected against degradation by radiation and/or oxidation by adding at least one stabilizing agent selected from hydroxybenzophenones, hydroxyphenyl benzotriazoles, oxalic acid anilides, hydroxyphenyl triazines, hindered phenols and/or merocyanines to the DPP polymer layer. The stabilization is effective both during production and during usage of the device, while the device's electronic properties are retained. The stabilizing agent is preferably a UV absorbing agent or an antioxidant or anti-radical agent known from the field of organic polymer technology.

First claim

The invention claimed is:

1. An organic semiconductor device, comprising:
at least one of an organic diode and an organic field effect transistor,
wherein the at least one of the organic diode and the organic field effect transistor comprises a semiconducting layer comprising a mixture comprising a diketopyrrolopyrrole (DPP) polymer and a stabilizing agent, the stabilizing agent being included in the mixture in an amount of from 0.0005 to 0.1 parts by weight per 1 part by weight of the DPP polymer, and
the stabilizing agent is selected from the group consisting of a UV absorbing agent, an antioxidant, and an anti-radical agent.

2. The device of claim 1 , wherein the stabilizing agent is at least one selected from the group consisting of a hydroxybenzophenone, a hydroxyphenyl benzotriazole, an oxalic acid anilide, a hydroxyphenyl triazine, a hindered phenole, and a merocyanine.

3. The device of claim 1 , wherein the stabilizing agent comprises a UV absorbing agent selected from the group consisting of:
a 2-hydroxybenzophenone of formula I

a 2-hydroxyphenylbenzotriazole of formula IIa, IIb or IIc

a 2-hydroxyphenyltriazine of formula III

an oxanilide of formula IV

 and
a merocyanine of formula V

each including E,E-, E,Z- and Z,Z-geometrical isomers thereof;
wherein
in formula I,
v is an integer from 1 to 3, w is 1 or 2, and the substituents Z independently of one another are hydrogen, halogen, hydroxyl or alkoxy having 1 to 12 carbon atoms;
in formula IIa,
R 1 is hydrogen, alkyl having 1 to 24 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, cycloalkyl having 5 to 8 carbon atoms or a radical of formula

 in which R 4 and R 5 independently of one another are alkyl having 1 to 5 carbon atoms, or R 4 , together with the radical C n H 2n+1−m , forms a cycloalkyl radical having 5 to 12 carbon atoms,
m is 1 or 2, n is an integer from 2 to 20, and
M is a radical of formula —COOR 6 in which R 6 is hydrogen, alkyl having 1 to 12 carbon atoms, alkoxyalkyl having in each case 1 to 20 carbon atoms in the alkyl moiety and in the alkoxy moiety or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,
R 2 is hydrogen, halogen, alkyl having 1 to 18 carbon atoms, alkyl of 2 to 4 carbon atoms substituted by C 2 -C 6 alkanoyloxy or C 3 -C 6 alkenoyloxy, or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, and
R 3 is hydrogen, halogen, alkyl or alkoxy having in each case 1to 4 carbon atoms or —COOR 6 in which R 6 is as defined above, at least one of the radicals R 1 and R 2 being other than hydrogen;
in formula IIb,
T is hydrogen or alkyl having 1 to 6 carbon atoms,
T 1 is hydrogen, chloro or alkyl or alkoxy having in each case 1to 4 carbon atoms,
n is 1 or 2 and,
if n is 1, T 2 is chloro or a radical of the formula —OT 3 or

 and,
if n is 2, T 2 is a radical of the formula

 or —O-T 9 -O—;
in which
T 3 is hydrogen, alkyl which has 1 to 18 carbon atoms and is unsubstituted or substituted by 1 to 3 hydroxyl groups or by —OCOT 6 , alkyl which has 3 to 18 carbon atoms, is interrupted once or several times by —O—or —NT 6 - and is unsubstituted or substituted by hydroxyl or —OCOT 6 , cycloalkyl which has 5 to 12 carbon atoms and is unsubstituted or substituted by hydroxyl and/or alkyl having 1 to 4 carbon atoms, alkenyl which has 2 to 18 carbon atoms and is unsubstituted or substituted by hydroxyl, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or a radical of formula
—CH 2 CH(OH)-T 7 or

T 4 and T 5 independently of one another are hydrogen, alkyl having 1 to 18 carbon atoms, alkyl which has 3 to 18 carbon atoms and is interrupted once or several times by —O—or —NT 6 -, cycloalkyl having 5 to 12 carbon atoms, phenyl, phenyl which is substituted by alkyl having 1 to 4 carbon atoms, alkenyl having 3 to 8 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety or hydroxyalkyl having 2 to 4 carbon atoms,
T 6 is hydrogen, alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms, alkenyl having 3 to 8 carbon atoms, phenyl, phenyl which is substituted by alkyl having 1 to 4 carbon atoms, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,
T 7 is hydrogen, alkyl having 1 to 18 carbon atoms, phenyl which is unsubstituted or substituted by hydroxyl, phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, or —CH 2 OT 8 ,
T 8 is alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 8 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, phenyl, phenyl which is substituted by alkyl having 1 to 4 carbon atoms, or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,
T 9 is alkylene having 2 to 8 carbon atoms, alkenylene having 4 to 8 carbon atoms, alkynylene having 4 carbon atoms, cyclohexylene, alkylene which has 2 to 8 carbon atoms and is interrupted once or several times by —O—, or a radical of the formula —CH 2 CH(OH)CH 2 OT 11 OCH 2 CH(OH)CH 2 —or —CH 2 —C(CH 2 OH) 2 —CH 2 —,
T 10 is alkylene which has 2 to 20 carbon atoms and can be interrupted once or several times by —O—, or cyclohexylene,
T 11 is alkylene having 2 to 8 carbon atoms, alkylene which has 2 to 18 carbon atoms and is interrupted once or several times by —O—, 1,3-cyclohexylene, 1,4-cyclohexylene, 1,3-phenylene or 1,4-phenylene, or
T 10 and T 6 , together with the two nitrogen atoms, are a piperazine ring;
in formula IIc,
R′ 2 is C 1 -C 12 alkyl and k is a number from 1 to 4;
in formula III,
u is 1 or 2 and r is an integer from 1 to 3,
Y 1 independently of one another are hydrogen, hydroxyl, phenyl or halogen, halogenomethyl, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 18 carbon atoms, alkoxy having 1 to 18 carbon atoms which is substituted by a group —COO(C 1 -C 18 alkyl);
if u is 1,
Y 2 is alkyl having 1 to 18 carbon atoms, phenyl which is unsubstituted or substituted by hydroxyl, halogen, alkyl or alkoxy having 1 to 18 carbon atoms;
alkyl which has 1 to 12 carbon atoms and is substituted by —COOH, —COOY 8 , —CONH 2 , —CONHY 9 , —CONY 9 Y 10 , —NH 2 , —NHY 9 , —NY 9 Y 10 , —NHCOY 11 , —CN and/or —OCOY 11 ;
alkyl which has 4 to 20 carbon atoms, is interrupted by one or more oxygen atoms and is unsubstituted or substituted by hydroxyl or alkoxy having 1 to 12 carbon atoms, alkenyl having 3 to 6 carbon atoms, glycidyl, cyclohexyl which is unsubstituted or substituted by hydroxyl, alkyl having 1 to 4 carbon atoms and/or —OCOY 11 , phenylalkyl which has 1 to 5 carbon atoms in the alkyl moiety and is unsubstituted or substituted by hydroxyl, chlorine and/or methyl, —COY 12 or —S

Assignees

• Basf Se

Inventors

• Kaihovirta Nikolai
• Mustonen Tero
• Vaidyanathan Subramanian
• Budry Jean-Luc

Classifications

• C08G2261/596

  against oxidation · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title

• H01L51/0036 Primary

  Electricity · mapped topic

• C08L79/04

  Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors · CPC title

• C08G2261/344

  containing heteroatoms · CPC title