ORGANIC SEMICONDUCTOR MATERIAL
Novel compounds useful as organic semiconductor material are described. Semiconductor devices containing said organic semiconductor material are also described.
1 . A compound having formula selected in the group consisting of formula (I), formula (II), formula (III) and formula (IV):
wherein:
R 1 , R 2 , R 2′ independently of each other, are selected in the group consisting of hydrogen, C 1 -C 40 linear or branched alkyl groups, C 1 -C 40 linear or branched heteroalkyl groups, C 3 -C 40 linear or branched cycloalkyl groups, C 1 -C 40 linear or branched hydroxyalkyl groups, C 1 -C 40 linear or branched alkoxyl groups, C 1 -C 40 linear or branched alkylcarboxylic groups, C 1 -C 40 linear or branched alkylcarboxyamide groups, C 1 -C 40 linear or branched alkylsulphonic groups, and C 1 -C 40 linear or branched nitrile groups;
Ar is selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups;
Ar′, Ar″, independently of each other, are selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups;
n, r, independently of each other, are integers between 1 and 50; and
p is an integer between 0 and 5;
with the exception of compounds of formula A:
wherein R 4 is selected in the group consisting of C 1 -C 4 alkyls; and R 5 is selected in the group consisting of monocyclic aryl groups and substituted monocyclic aryl groups;
with the exception of the compound of formula 132:
and with the exception of compounds of formula B:
wherein R 6 is selected in the group consisting of isopropyl, cyclopropyl and terbutyl groups and R 7 is selected in the group consisting of phenyl, 2-fluorphenyl, 3-fluorphenyl, 4-fluorphenyl, 2-chlorphenyl, 3-chlorphenyl, 4-chlorphenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dichlorophenyl, 2,4,6-trimethylphenyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl.
2 . The compound according to claim 1 , wherein when p is 0, n is between 2 and 50.
3 . The compound according to claim 1 , having formula selected in the group consisting of formula (Ia), formula (IIa), formula (IIIa) and formula (IVa)
wherein:
R 1 , R 2 , independently of each other, are selected in the group consisting of hydrogen, C 1 -C 40 linear or branched alkyl groups, C 1 -C 40 linear or branched heteroalkyl groups, C 3 -C 40 linear or branched cycloalkyl groups, C 1 -C 40 linear or branched hydroxyalkyl groups, C 1 -C 40 linear or branched alkoxyl groups, C 1 -C 40 linear or branched alkylcarboxylic groups, C 1 -C 40 linear or branched alkylcarboxyamide groups, C 1 -C 40 linear or branched alkylsulphonic groups, and C 1 -C 40 linear or branched nitrile groups;
Ar is selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl group and polycyclic heteroaryl group;
Ar′ is a moiety selected in the group consisting of a monocyclic aryl group, polycyclic aryl group, monocyclic heteroaryl group and polycyclic heteroaryl group.
4 . The compound according to claim 3 , wherein Ar is selected in the group consisting of the following rings (f), (g), (h), (i), (l), (m), (n), (o), (p):
wherein X is selected in the group consisting of S, O, Si, Se, NR 3 ,
R 3 being selected in the group consisting of C 1 -C 12 linear or branched alkyl groups, C 1 -C 12 linear or branched halogenoalkyl groups, C 3 -C 12 linear or branched cycloalkyl groups, C 1 -C 12 linear or branched hydroxyalkyl groups, C 1 -C 12 linear or branched alkoxyl groups, C 1 -C 12 linear or branched alkylcarboxylic groups, C 1 -C 12 linear or branched alkylcarboxyamide groups, C 1 -C 12 linear or branched alkylsulphonic groups, and C 1 -C 12 linear or branched nitrile groups.
5 . The compound according to claim 1 , wherein R 1 , R 2 , independently of each other, are selected in the group consisting of C 1 -C 12 linear or branched alkyl groups, C 1 -C 12 linear or branched heteroalkyl groups, C 3 -C 12 linear or branched cycloalkyl groups, C 1 -C 12 linear or branched hydroxyalkyl groups, C 1 -C 12 linear or branched alkoxyl groups, C 1 -C 12 linear or branched alkylcarboxylic groups, C 1 -C 12 linear or branched alkylcarboxyamide groups, C 1 -C 12 linear or branched alkylsulphonic groups, and C 1 -C 12 linear or branched nitrile groups.
6 . The compound according to claim 1 , wherein Ar′ is a unit selected in the group consisting of the following units (a), (b), (c):
wherein W is selected in the group consisting of S, SO and SO 2 ;
Y is selected in the group consisting of S, O, NR 8 ; and
R 6 , R 7 , and R 8 independently of each other, are selected in the group consisting of hydrogen, C 1 -C 12 linear or branched alkyl groups, C 1 -C 12 linear or branched halogenoalkyl groups, C 3 -C 12 linear or branched cycloalkyl groups, C 1 -C 12 linear or branched hydroxyalkyl groups, C 1 -C 12 linear or branched alkoxyl groups, C 1 -C 12 linear or branched alkylcarboxylic groups, C 1 -C 12 linear or branched alkylcarboxyamide groups, C 1 -C 12 linear or branched alkylsulphonic groups, and C 1 -C 12 linear or branched nitrile groups.
7 . The compound according to claim 1 having the following formula (V):
wherein R 4 , R 5 , independently of each other, are selected in the group consisting of C 1 -C 8 linear or branched saturated alkyl groups, C 1 -C 8 linear or branched fluoroalkyl groups, C 1 -C 8 linear or branched heteroalkyl groups comprising a heteroatom selected among O, S, N; and
m is an integer between 1 and 30.
8 . The compound according to claim 7 , having formula (VI):
9 . The compound according to claim 1 , having the following formula (VII):
wherein R 4 , R 5 , independently of each other, are selected in the group consisting of C 1 -C 8 linear or branched saturated alkyl groups, C 1 -C 8 linear or branched fluoroalkyl groups, C 1 -C 8 linear or branched heteroalkyl groups comprising a heteroatom selected among O, S, N.
10 . A process for the preparation of the compound according to claim 1 , comprising:
subjecting a reaction mixture comprising a reaction medium and an halogenated aromatic halide to:
a Stille coupling reaction with an organotin compound; or
to a Suzuki coupling reaction with an organoboron compound.
11 . A method comprising:
using a compound having formula selected in the group consisting of formula (I), formula (II), formula (III) and formula (IV):
wherein:
R 1 , R 2 , R 2′ independently of each other, are selected in the group consisting of hydrogen, C 1 -C 40 linear or branched alkyl groups, C 1 -C 40 linear or branched heteroalkyl groups, C 3 -C 40 linear or branched cycloalkyl groups, C 1 -C 40 linear or branched hydroxyalkyl groups, C 1 -C 40 linear or branched alkoxyl groups, C 1 -C 40 linear or branched alkylcarboxylic groups, C 1 -C 40 linear or branched alkylcarboxyamide groups, C 1 -C 40 linear or branched alkylsulphonic groups, and C 1 -C 40 linear or branched nitrile groups;
Ar is selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups;
Ar′, Ar″, independently of each other, are selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups;
n, r, independently of each other, are integers between 1 and 50; and
p is an integer between 0 and 5;
as an organic semiconductor material in an electronic device.
12 . A method comprising:
using the compound according to claim 2 as an organic semiconductor material in an electronic device.
13 . The method according to claim 11 , wherein the organic semiconductor material is an n-type organic semiconductor material.
14 . An electronic device comprising a semiconductor layer in contact with a number of electrodes, wherein the semiconductor layer includes at least one compound having formula selected in the group consisting of formula (I), formula (II), formula (III) and formula (IV):
wherein:
R 1 , R 2 , R 2′ independently of each other, are selected in the group consisting of hydrogen, C 1 -C 40 linear or branched alkyl groups, C 1 -C 40 linear or branched heteroalkyl groups, C 3 -C 40 linear or branched cycloalkyl groups, C 1 -C 40 linear or branched hydroxyalkyl groups, C 1 -C 40 linear or branched alkoxyl groups, C 1 -C 40 linear or branched alkylcarboxylic groups, C 1 -C 40 linear or branched alkylcarboxyamide groups, C 1 -C 40 linear or branched alkylsulphonic groups, and C 1 -C 40 linear or branched nitrile groups;
Ar is selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups;
Ar′, Ar″, independently of each other, are selected in the group consisting of monocyclic aryl groups, polycyclic aryl groups, monocyclic heteroaryl groups and polycyclic heteroaryl groups;
n, r, independently of each other, are integers between 1 and 50; and
p is an integer between 0 and 5.
15 . An electronic device comprising a semiconductor layer in contact with a number of electrodes, wherein the semiconductor layer includes at least one compound according to claim 2 .