Thieno[2,3-C]Pyrrole-dione derivatives and their use for organic semiconductors
Compounds of formulae (I) and (II) useful as organic semiconductor materials, and semiconductor devices containing such organic semiconductor materials are described.
1. A compound having formula (II):
wherein:
R 1 , R 2 , R 3 independently of each other, are selected from a group consisting of C 1 -C 6 linear alkyl groups, C 6 cycloalkyl groups, and C 6 unsubstituted and substituted monocyclic aryl groups;
R 4 and R 5 , independently of each other, are selected from a group consisting of hydrogen, and C 1 alkyl group,
Ar 1 , Ar 2 , Ar 3 and Ar 4 , independently of each other, are moieties selected from a group consisting of a C 6 unsubstituted and substituted monocyclic aryl groups, C 4 unsubstituted and substituted monocyclic heteroaryl groups, and C 6 unsubstituted and substituted polycyclic heteroaryl groups or combinations thereof as dimers, trimers and tetramers;
Z and Z′, independently of each other, are selected from a group consisting of bivalent radicals of formulas (III), (IV), (V), and (VI):
wherein G is selected from a group consisting of hydrogen, halogens, C 1 -C 20 linear or branched alkyl groups, C 2 -C 20 linear or branched alkenyl groups, C 2 -C 20 linear or branched alkynyl groups, C 1 -C 20 linear or branched heteroalkyl groups, C 2 -C 20 linear or branched heteroalkenyl groups, C 2 -C 20 linear or branched heteroalkynyl groups, C 3 -C 20 linear or branched cycloalkyl groups, C 3 -C 20 linear or branched heterocycloalkyl groups, C 2 -C 20 linear or branched alkylcarboxylic groups, C 2 -C 20 linear or branched alkylcarboxamide groups, C 2 -C 20 linear or branched alkylimino groups, C 1 -C 20 linear or branched alkylsulphonic groups, C 1 -C 20 linear or branched nitrile groups, C 6 -C 50 unsubstituted and substituted monocyclic aryl groups, C 10 -C 50 polycyclic aryl groups, C 10 -C 50 substituted polycyclic aryl groups, C 1 -C 50 unsubstituted and substituted monocyclic heteroaryl groups, C 6 -C 50 polycyclic heteroaryl groups, and C 6 -C 50 substituted polycyclic heteroaryl groups or combinations thereof;
s is 0 or 1;
n, m, r and t, independently of each other, are integers between 1 and 50;
q and f, independently of each other, are integers between 1 and 10; and
p is 0.
2. The compound according to claim 1 , having formula (IIa):
wherein R 1 , R 2 , R 4 , R 5 , Ar 1 , Ar 4 , Z, f, n, m are as specified in claim 1 .
3. The compound according to claim 1 , wherein q and f are each 1 or 2, and n, and m are between 2 and 10.
4. The compound according to claim 1 , wherein Z′ and/or Z are selected from a group consisting of ethynylene, cis-ethenylene and trans-ethenylene.
5. The compound according to claim 1 , wherein Ar 1 , Ar 2 , Ar 3 and/or Ar 4 , independently of each other, are selected from a group consisting of the following units (a), (b), (c), (d), (e), (f), (g), (h), (i), (l), (m), (n), (o), (p), (q), and (r):
wherein A is selected from a group consisting of S, O, Se, atoms and SO, SO 2 , R 14 —P═O, P—R 14 , N—R 15 , Si(R 15 ) 2 ) groups;
D is selected from a group consisting of C, S, O Se, atoms and SO, SO 2 , R 14 —P═O, P—R 14 , BR 14 , N—R 15 , Si(R 15 ) 2 groups;
B, C, independently of each other, are selected from a group consisting of C, N atoms;
E is selected from a group consisting of C(R 15 ) 2 , S, O, and NR 15 group;
R 8 , R 9 , R 10 , R 11 , R 12 and R 13 , independently of each other, are selected from a group consisting of hydrogen, halogens, C 1 -C 20 linear or branched alkyl groups, C 2 -C 20 linear or branched alkenyl groups, C 2 -C 20 linear or branched alkynyl groups, C 1 -C 20 linear or branched heteroalkyl groups, C 2 -C 20 linear or branched heteroalkenyl groups, C 2 -C 20 linear or branched heteroalkynyl groups, C 3 -C 20 linear or branched cycloalkyl groups, C 2 -C 20 linear or branched heterocycloalkyl groups, C 2 -C 20 linear or branched alkylcarboxylic groups, C 2 -C 20 linear or branched alkylcarboxamide groups, C 2 -C 20 linear or branched alkylimino groups, C 1 -C 20 linear or branched alkylsulphonic groups, C 1 -C 20 linear or branched nitrile groups, and C 5 -C 40 aryl groups, C 6 -C 40 alkylaryl groups;
R 14 , R 15 independently of each other, are selected from a group consisting of hydrogen, C 1 -C 20 linear or branched alkyl groups, C 2 -C 20 linear or branched alkenyl groups, C 2 -C 20 linear or branched alkynyl groups, C 1 -C 20 linear or branched heteroalkyl groups, C 2 -C 20 linear or branched heteroalkenyl groups, C 2 -C 20 linear or branched heteroalkynyl groups, C 3 -C 20 linear or branched cycloalkyl groups, C 3 -C 20 linear or branched heterocycloalkyl groups, C 2 -C 20 linear or branched alkylcarboxylic groups, C 2 -C 20 linear or branched alkylcarboxamide groups, C 2 -C 20 linear or branched alkylimino groups, C 1 -C 20 linear or branched alkylsulphonic groups, C 1 -C 20 linear or branched nitrile groups, C 5 -C 40 aryl groups, and C 6 -C 40 alkylaryl groups.
6. The compound according to claim 1 , wherein Ar 1 , Ar 2 , Ar 3 and/or Ar 4 , independently of each other, are selected from a group consisting of the following groups (s) and (t):
wherein A is selected from a group consisting of S, O, Se, atoms and SO, SO 2 , R 14 —P═O, P—R 14 , N—R 15 , Si(R 15 ) 2 groups;
W is a moiety selected from a group consisting of the units (a), (b), (c), (d), (e), (f), (g), (h), (i), (l), (m), (n), (o), (p), (q), and (r) of claim 5 ; and
R 16 is selected from a group consisting of hydrogen, halogens, C 1 -C 20 linear or branched alkyl groups, C 2 -C 20 linear or branched alkenyl groups, C 2 -C 20 linear or branched alkynyl groups, C 1 -C 20 linear or branched heteroalkyl groups, C 2 -C 20 linear or branched heteroalkenyl groups, C 2 -C 20 linear or branched heteroalkynyl groups, C 3 -C 20 linear or branched cycloalkyl groups, C 3 -C 20 linear or branched heterocycloalkyl groups, C 1 -C 20 linear or branched alkylcarboxylic groups, C 1 -C 20 linear or branched alkylcarboxamide groups, C 1 -C 20 linear or branched alkylimino groups, C 1 -C 20 linear or branched alkylsulphonic groups, C 1 -C 20 linear or branched nitrile groups, C 5 -C 40 aryl groups, and C 6 -C 40 alkylaryl groups.
7. The compound according to claim 1 , wherein Ar 1 , Ar 2 , Ar 3 and/or Ar 4 , independently of each other, are selected from a group consisting of the following formulas (u), (v), (w), (x) and (y):
wherein n is comprised between 2 and 10 and R 8 , R 9 , independently of each other, are selected from a group consisting of hydrogen, halogens, C 1 -C 20 linear or branched alkyl groups, C 2 -C 20 linear or branched alkenyl groups, C 2 -C 20 linear or branched alkynyl groups, C 1 -C 20 linear or branched heteroalkyl groups, C 2 -C 20 linear or branched heteroalkenyl groups, C 2 -C 20 linear or branched heteroalkynyl groups, C 3 -C 20 linear or branched cycloalkyl groups, C 2 -C 20 linear or branched heterocycloalkyl groups, C 2 -C 20 linear or branched alkylcarboxylic groups, C 2 -C 20 linear or branched alkylcarboxamide groups, C 2 -C 20 linear or branched alkylimino groups, C 1 -C 20 linear or branched alkylsulphonic groups, C 1 -C 20 linear or branched nitrile groups, C 5 -C 40 aryl groups, and C 6 -C 40 alkylaryl groups.
8. A compound having the following formula:
9. An organic semiconductor material in an electronic device comprising the compound according to claim 1 .
10. The organic semiconductor material in the electronic device according to claim 9 , wherein the organic semiconductor material is an n-type organic semiconductor material.
11. 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 1 .
12. A compound having formula (I):
wherein:
R 1 , R 2 , R 3 independently of each other, are selected from a group consisting of C 1 -C 6 linear alkyl groups, C 6 cycloalkyl groups, and C 6 unsubstituted and substituted monocyclic aryl groups;
Ar, Ar 1 , Ar 2 , Ar 3 and Ar 4 , independently of each other, are moieties selected from a group consisting of a C 6 unsubstituted and substituted monocyclic aryl groups, C 4 unsubstituted and substituted monocyclic heteroaryl groups, and C 6 unsubstituted and substituted polycyclic heteroaryl groups or combinations thereof as dimers, trimers and tetramers;
Z and Z′, independently of each other, are selected from a group consisting of bivalent radicals of formulas (III), (IV), (V), and (VI):
wherein G is selected from a group consisting of hydrogen, halogens, C 1 -C 20 linear or branched alkyl groups, C 2 -C 20 linear or branched alkenyl groups, C 2 -C 20 linear or branched alkynyl groups, C 1 -C 20 linear or branched heteroalkyl groups, C 2 -C 20 linear or branched heteroalkenyl groups, C 2 -C 20 linear or branched heteroalkynyl groups, C 3 -C 20 linear or branched cycloalkyl groups, C 3 -C 20 linear or branched heterocycloalkyl groups, C 2 -C 20 linear or branched alkylcarboxylic groups, C 2 -C 20 linear or branched alkylcarboxamide groups, C 2 -C 20 linear or branched alkylimino groups, C 1 -C 20 linear or branched alkylsulphonic groups, C 1 -C 20 linear or branched nitrile groups, C 6 -C 50 unsubstituted and substituted monocyclic aryl groups, C 10 -C 50 polycyclic aryl groups, C 10 -C 50 substituted polycyclic aryl groups, C 1 -C 50 unsubstituted and substituted monocyclic heteroaryl groups, C 6 -C 50 polycyclic heteroaryl groups, and C 6 -C 50 substituted polycyclic heteroaryl groups or combinations thereof;
s is 0 or 1;
n, m, r and t, independently of each other, are integers between 1 and 50;
q and f, independently of each other, are integers between 1 and 10; and
p is 0.
13. The compound according to claim 12 , having formula (Ia):
wherein R 1 , R 2 , Ar, Ar 1 , Ar 4 , Z, f, n, m are as specified in claim 12 .
14. The compound according to claim 12 , wherein q and f are each 1 or 2, and n, and m are between 2 and 10.
15. The compound according to claim 12 , wherein Z′ and/or Z are selected from a group consisting of ethynylene, cis-ethenylene and trans-ethenylene.