IP Library › Granted Patent US 9,978,943

Granted Patent B2

US 9,978,943 · App. 14/361,129 · Granted May 22, 2018

Organic field effect transistor

Inventors: Patrice Bujard (Courtepin, CH); Natalia Chebotareva (Hagenthal le Bas, FR); Thomas Weitz (Mannheim, DE); Pascal Hayoz (Hofstetten, CH)

Assignee: BASF SE

H01L51/0003 C08G61/124 C08G61/126 C08L65/00 C09B57/004 C09B69/105 C09B69/109 H01L51/002 H01L51/005 H01L51/0035 H01L51/0036 H01L51/0043 H01L51/0068 H01L51/0072 H01L51/0512 C08G2261/1412 C08G2261/226 C08G2261/228 C08G2261/3223 C08G2261/344 C08G2261/364 C08G2261/411 C08G2261/91 C08G2261/92 C08G2261/95 C08L2205/02 H01L51/0053 H01L51/0545 H01L51/0558

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Quick Facts

Patent No.: US 9,978,943
App. No.: 14/361,129
Granted: May 22, 2018
Kind: B2

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Abstract

The present invention provides an electronic component or device comprising a gate electrode, a source electrode and a drain electrode, wherein said component or device further comprising an organic semiconducting (OSC) material that is provided between the source and drain electrode, wherein the OSC material comprises (a) a polymer represented by formula: (I), and (b) a compound of formula (II). High quality OFETs can be fabricated by the choice of a semiconductor material, which is comprised of a polymer represented by formula I and (b) a compound of formula II.

Claims (150)

1. An electronic component or an electronic device comprising:

a gate electrode;

a source electrode; and

a drain electrode;

wherein the component or the device further comprises an organic semiconducting (OSC) material that is provided between the source electrode and the drain electrode, wherein the OSC material comprises

(a) a polymer of formula Ib:

wherein at least one of A 6 and A 7 is

and the other of A 6 and A 7 is

s is an integer 1, or 2; t is an integer 1, or 2;

M is

v is an integer 1, 2, or 3;

R 101 and R 102 are a C 1 -C 38 alkyl group and n is 5 to 1000,

wherein the polymer of formula Ib is not a polymer of formula Ib-3:

and

(b) a compound of formula IIa:

wherein

a is 1, or 2; b is 0, or 1; c is 0, or 1;

R 1 and R 2 are the same or different and are a C 1 -C 38 alkyl group,

Ar 1 , Ar 2 and Ar 3 are each independently a bivalent group of formula

R 3 is hydrogen, cyano,

wherein the compound of formula IIa is present in said OSC material in an amount of 0.1 to 99.9% by weight based on the amount of the polymer of formula Ib and the compound of formula IIa.

2. The component or the device of claim 1 , wherein the compound of formula IIa is a compound of formula

wherein R 1 and R 2 are the same and are a C 1 -C 38 alkyl group.

3. The component or the device of claim 1 , wherein the compound of formula IIa is present in said OSC material in an amount of 5 to 95% by weight, based on the amount of the polymer of formula Ib and the compound of formula IIa.

4. A process for preparing the device of claim 1 , the process comprising:

(i) mixing one or more the of compound of formula IIa and the polymer of formula Ib, optionally with a solvent or solvent mixture,

(ii) applying the mixture or the solvent comprising the compound of formula IIa and the polymer of formula Ib to a substrate; and

optionally evaporating the solvent to form a solid OSC layer.

5. An organic layer, comprising a polymer of a formula Ib and a compound of a formula IIa

wherein at least one of A 6 and A 7 is

and the other of A 6 and A 7 is

s is an integer 1, or 2; t is an integer 1, or 2;

M is

v is an integer 1, 2, or 3;

R 101 and R 102 are a C 1 -C 38 alkyl group and n is 5 to 1000,

wherein the polymer of formula Ib is not a polymer of formula Ib-3:

and

wherein

a is 1, or 2; b is 0, or 1; c is 0, or 1;

R 1 and R 2 are the same or different and are a C 1 -C 38 alkyl group,

Ar 1 , Ar 2 and Ar 3 are each independently a bivalent group of formula

R 3 is hydrogen, cyano,

6. A formulation, comprising

(a) a polymer of a formula Ib,

wherein at least one of A 6 and A 7 is

and the other of A 6 and A 7 is

s is an integer 1, or 2; t is an integer 1, or 2;

M is

v is an integer 1, 2, or 3;

R 101 and R 102 are a C 1 -C 38 alkyl group and n is 5 to 1000,

wherein the polymer of formula Ib is not a polymer of formula Ib-3:

(b) a compound of a formula IIa,

wherein

a is 1, or 2; b is 0, or 1; c is 0, or 1;

R 1 and R 2 are the same or different and are a C 1 -C 38 alkyl group,

Ar 1 , Ar 2 and Ar 3 are each independently a bivalent group of formula

R 3 is hydrogen, cyano,

and

7. An organic semiconductor device comprising the organic layer of claim 5 .

8. An organic layer comprising the formulation of claim 6 .

9. An apparatus, comprising the component or the device of claim 1 .

10. The component or the device of claim 4 , wherein the compound of formula IIa is a compound of formula (IIa-1).

11. The organic layer of claim 5 , wherein the organic layer is a semiconducting layer.

12. The electronic component or the electronic device of claim 1 , wherein the polymer represented by formula (Ib) is a polymer of formula

and

R 101 and R 102 are a C 1 -C 38 alkyl group, and n is 5 to 1000.

13. An electronic component or an electronic device comprising:

a gate electrode;

a source electrode; and

a drain electrode;

(a) a polymer of formula Ib:

wherein A 6 and A 7 are each independently

s is an integer 1, or 2; t is an integer 1, or 2;

M is

v is an integer 1, 2, or 3;

R 101 and R 102 are a C 1 -C 38 alkyl group and n is 5 to 1000,

wherein the polymer of formula Ib is not a polymer of formula Ib-3:

and

(b) a compound of formula IIa:

wherein

a is 1, or 2; b is 0, or 1; c is 0, or 1;

R 1 and R 2 are the same or different and are a C 1 -C 38 alkyl group,

Ar 1 , Ar 2 and Ar 3 are each independently a bivalent group of formula

wherein at least one Ar 1 is

R 3 is hydrogen, cyano,

wherein the compound of formula IIa is present in said OSC material in an amount of 0.1 to 99.9% by weight based on the amount of the polymer of formula Ib and the compound of formula IIa.

14. The component or the device of claim 1 , wherein the compound of formula IIa is a compound of formula

wherein R 1 and R 2 are the same and are a C 1 -C 38 alkyl group.

15. The component or the device of claim 13 , wherein the compound of formula IIa is present in said OSC material in an amount of 5 to 95% by weight, based on the amount of the polymer of formula Ib and the compound of formula IIa.

16. A process for preparing the device of claim 13 , the process comprising:

(i) mixing one or more the of compound of formula IIa and the polymer of formula Ib, optionally with a solvent or solvent mixture,

(ii) applying the mixture or the solvent comprising the compound of formula IIa and the polymer of formula Ib to a substrate; and

optionally evaporating the solvent to form a solid OSC layer.

17. An organic layer, comprising a polymer of a formula Ib and a compound of a formula IIa

wherein A 6 and A 7 are each independently

s is an integer 1, or 2; t is an integer 1, or 2;

M is

v is an integer 1, 2, or 3;

R 101 and R 102 are a C 1 -C 38 alkyl group and n is 5 to 1000,

wherein the polymer of formula Ib is not a polymer of formula Ib-3:

and

wherein

a is 1, or 2; b is 0, or 1; c is 0, or 1;

R 1 and R 2 are the same or different and are a C 1 -C 38 alkyl group,

Ar 1 , and Ar 2 and Ar 3 are each independently a bivalent group of formula

wherein at least one Ar 1 is

R 3 is hydrogen, cyano,

18. A formulation, comprising

(a) a polymer of a formula Ib,

wherein A 6 and A 7 are each independently

s is an integer 1, or 2; t is an integer 1, or 2;

M is

v is an integer 1, 2, or 3;

R 101 and R 102 are a C 1 -C 38 alkyl group and n is 5 to 1000,

wherein the polymer of formula Ib is not a polymer of formula Ib-3:

(b) a compound of a formula IIa,

wherein

a is 1, or 2; b is 0, or 1; c is 0, or 1;

R 1 and R 2 are the same or different and are a C 1 -C 38 alkyl group,

Ar 1 , Ar 2 and Ar 3 are each independently a bivalent group of formula

wherein at least one Ar 1 is

R 3 is hydrogen, cyano,

and

19. An organic semiconductor device comprising the organic layer of claim 16 .

20. An organic layer comprising the formulation of claim 17 .

21. An apparatus, comprising the component or the device of claim 13 .

22. The component or the device of claim 14 , wherein the compound of formula IIa is a compound of formula (IIa-1).

23. The organic layer of claim 16 , wherein the organic layer is a semiconducting layer.

24. The electronic component or the electronic device of claim 13 , wherein the polymer represented by formula (Ib) is a polymer of formula

and

R 101 and R 102 are a C 1 -C 38 alkyl group, and n is 5 to 1000.

25. The electronic component or the electronic device of claim 13 , wherein the polymer represented by formula (Ib) is a polymer of formula

and

R 101 and R 102 are a C 1 -C 38 alkyl group, and n is 5 to 1000.

26. The electronic component or the electronic device of claim 13 , wherein the polymer represented by formula (Ib) is a polymer of formula

and

R 101 and R 102 are a C 1 -C 38 alkyl group, and n is 5 to 1000.

27. The electronic component or the electronic device of claim 13 , wherein the polymer represented by formula (Ib) is a polymer of formula

and

R 101 and R 102 are a C 1 -C 38 alkyl group, and n is 5 to 1000.

28. The electronic component or the electronic device of claim 13 , wherein the polymer represented by formula (Ib) is a polymer of formula

and

R 101 and R 102 are a C 1 -C 38 alkyl group, and n is 5 to 1000.

29. The electronic component or the electronic device of claim 13 , wherein the polymer represented by formula (Ib) is a polymer of formula

and

R 101 and R 102 are a C 1 -C 38 alkyl group, and n is 5 to 1000.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2020

From: BASF SE

To: CLAP CO., LTD.

Reel/Frame 052459/0201 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 28, 2014

From: BUJARD, PATRICE; CHEBOTAREVA, NATALIA; WEITZ, THOMAS; HAYOZ, PASCAL

To: BASF SE

Reel/Frame 032976/0763 →

Priority Claims (1)

EP 11192317 · Dec 7, 2011 · regional

Continuity (2)

Provisional Application 61567652 · Dec 7, 2011

Related Publication 20140299871A1 · Oct 9, 2014