Granted Patent B2

US 9,502,665 · App. 14/435,411 · Granted Nov 22, 2016

Inventors: Manuela Melucci (Bologna, IT); Laura Favaretto (Ozzano dell'Emilia, IT); Massimo Zambianchi (Cesena, IT); Raffaella Capelli (Bologna, IT); Michele Muccini (Bologna, IT)

Assignee: E.T.C. S.R.L.

H01L51/0071C07D495/04C09K11/06H01L51/0068C09K2211/1037H01L51/0545H01L51/0558H01L51/5296H01L2251/308

Abstract

Claims (46)

1. A compound having formula (IIa)

wherein:

n is an integer between 1 and 50;

Ar′ is:

a unit selected from the group consisting of the following units (a), (b), (c), (d), (e), (f), (g), (h), (i), (l), (m), (k), (o), (p), (q), and (r):

wherein A is selected from the group consisting of S, O Se, atoms and SO, SO 2 ,R 14 —P═O, P—R 14 , N—R 15 , and Si(R 15 ) 2 groups;

D is selected from the group consisting of C, S, O Se, atoms and SO, SO 2 , R 14 —P═O, P—R 14 ,BR 14 , N—R 15 , and Si(R 15 ) 2 groups;

B, C, independently of each other, are selected from the group consisting of C, and N atoms;

E is selected from the 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 the 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;

R 14 , R 15 independently of each other, are selected from the 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 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 2 -C 20 linear or branched nitrile groups, C 5 -C 40 aryl groups, C 1 -C 40 heteroaryl groups, and C 6 -C 40 alkylaryl groups; or

the [Ar′] n unit is selected from the group consisting of the following groups (s) and (t):

wherein A is as defined above;

W is a moiety selected from the group consisting of the above defined units (a), (b), (c), (d), (e), (f), (g), (h), (i), (l), (m), (n), (o), (p), (q), and (r); and

R 16 is selected from the group consisting of the 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, C 1 -C 40 heteroaryl groups, and C 6 -C 40 alkylaryl groups; or

the [Ar′] n unit is selected from the group consisting of following formulas (u), (v), (w), (x)and (y):

wherein n is comprised between 2 and 10 and R 8 , R 9 are as defined above;

T is selected from the group consisting of 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 fluoroalkyl groups, C 1 -C 20 thioalkyl groups, C 1 -C 20 silicioalkyl groups, C 1 -C 20 alkylamino groups, C 2 -C 20 alkylimino groups, phenyl groups, phenyl groups substituted with at least one C 1 -C 10 alkyl group and/or with at least one C 1 -C 10 heteroalkyl groups, thienyl group, thienyl groups substituted with at least one C 1 -C 10 alkyl group and/or with at least one C 1 -C 10 heteroalkyl groups, naphthalene, substituted naphthalene, antracene, substituted antracene, and C 4 -C 20 triciclic heteroaryl groups, and

R 1 is selected from the group consisting of C 1 -C 40 linear and branched alkyl groups.

2. The compound according to claim 1 , wherein said compound is selected from the group consisting of the following compounds 6, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, and 18:

3. An electronic device comprising the compound according to claim 1 as an organic semiconductor material.

4. The electronic device according to claim 3 , wherein the organic semiconductor material is an n-type organic semiconductor material.

5. An electronic device comprising a semiconductor layer in contact with a number of electrodes, wherein the semiconductor layer includes at least one compound according claim 1 .

6. A compound having formula (Ia)

wherein:

n is an integer between 1 and 50;

Ar is selected from the group consisting of the following rings (α), (β), (γ), (δ), (∈), (ζ), (η), (θ), and (ι):

wherein X is selected from the group consisting of S, SO, SO 2 , O, Si, Se, and NR 17 ,

Y is selected from the group consisting of C and N;

R 17 is selected from the 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 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, C 1 -C 40 heteroaryl groups, and C 6 -C 40 alkylaryl groups;

Ar′ is:

a unit selected from the group consisting of the following units (a), (b), (c), (d), (e), (f), (g), (h), (i), (l), (m), (k), (o), (p), (q), and (r):

wherein A is selected from the group consisting of S, O, and Se atoms and SO, SO 2 , R 14 —P═O, P—R 14 ,N—R 15 , and Si(R 15 ) 2 groups;

D is selected from the group consisting of C, S, O, Se, atoms and SO, SO 2 , R 14 —P═O, P—R 14 ,BR 14 ,N—R 15 , and Si(R 15 ) 2 groups;

B, C, independently of each other, are selected from the group consisting of C, and N atoms;

E is selected from the 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 the 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;

R 14 ,R 15 independently of each other, are selected from the 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 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 2 -C 20 linear or branched nitrile groups, C 5 -C 40 aryl groups, C 1 -C 40 heteroaryl groups, and C 6 -C 40 alkylaryl groups; or

the [Ar′] n unit is selected from the group consisting of the following groups (s) and (t):

wherein A is as defined above;

W is a moiety selected from the group consisting of the above defined units (a), (b), (c), (d), (e), (f), (g), (h), (i), (l), (m), (n), (o), (p), (q), and (r); and

R 16 is selected from the group consisting of the 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, C 1 -C 40 heteroaryl groups, and C 6 -C 40 alkylaryl groups; or

the [Ar′] n unit is selected from the group consisting of following formulas (u), (v), (w), (X) and(y):

wherein n is comprised between 2 and 10 and R 8 , R 9 are as defined above;

T is selected from the group consisting of 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 fluoroalkyl groups, C 1 -C 20 thioalkyl groups, C 1 -C 20 silicioalkyl groups, C 1 -C 20 alkylamino groups, C 2 -C 20 alkylimino groups, phenyl groups, phenyl groups substituted with at least one C 1 -C 10 alkyl group and/or with at least one C 1 -C 10 heteroalkyl groups, thienyl group, thienyl groups substituted with at least one C 1 -C 10 alkyl group and/or with at least one C 1 -C 10 heteroalkyl groups, naphthalene, substituted naphthalene, antracene, substituted antracene, and C 4 -C 20 triciclic heteroaryl groups, and

R 1 is selected from the group consisting of C 1 -C 40 linear and branched alkyl groups.

Assignments (9)

Priority Claims (1)

Continuity (1)