IP Library › Granted Patent US 9,431,145
Granted Patent B2
US 9,431,145 · App. 14/118,811 · Granted Aug 30, 2016

Transistors and methods for making them

Inventors: Beverley Anne Brown (Warrington, GB); Simon Dominic Ogier (Ripon, GB); Keri Laura McCall (Ripon, GB); Marco Palumbo (Liverpool, GB)
Assignee: Neudrive Limited
H01B1/121H01L51/0035H01L51/0043H01L51/0512H01L51/0566H01L51/0094H01L51/0541H01L51/0545
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Quick Facts
Patent No.
US 9,431,145
App. No.
14/118,811
Granted
Aug 30, 2016
Kind
B2
Abstract

A semiconductor composition which comprises a soluble polyacene semiconductor and a polymeric semiconducting binder the binder having a permittivity greater than 3.4 at 000 Hz. The charge mobility of the semiconducting binder when measured in a pure state is greater than 10 −7 cm 2 /Vs and more preferably greater than 10 −6 cm 2 /Vs. Organic thin film transistors in which the source and drain electrodes are bridged by the semiconductor composition have desirable properties of reproducibility and charge mobility. The organic semiconducting composition can be applied by solution coating.

Claims (63)

1. A semiconductor composition comprising:

a soluble polyacene semiconductor;

a polymeric semiconducting binder;

wherein the polymeric semiconducting binder has a permittivity greater than 3.4 at 1000 Hz; and

wherein the polymeric semiconducting binder comprises triarylamine repeat units.

2. The semiconductor composition according to claim 1 , wherein the charge mobility of the polymeric semiconducting binder when measured in a pure state is greater than 10 −7 cm 2 V −1 s −1 .

3. The semiconductor composition according to claim 2 , wherein the charge mobility of the polymeric semiconducting binder when measured in a pure state is greater than 10 −6 cm 2 V −1 s −1 .

4. The semiconductor composition according to claim 1 , wherein at least one of the triarylamine repeat units is substituted by cyano groups or by groups which comprise cyano groups or by alkoxy groups.

5. The semiconductor composition according to claim 1 , wherein the triarylamine repeat units comprise at least one of:

6. The semiconductor composition according to claim 1 , wherein the polymeric semiconducting binder is represented by the Formula (I) comprising at least one of first and second monomer units:

wherein each R x is independently selected from hydrogen, an alkyl group, an alkoxy group, halogen, a nitro group or R y , where each R y is independently a cyano group (CN) or an organic group that includes at least one CN group, and wherein at least one of the repeat units is substituted by cyano groups or by groups which comprise cyano groups or by alkoxy groups;

the sum of indices (j+k+l) is at least 1;

each R Z is independently an alkyl group optionally substituted by one or more substituents selected from hydroxyl, alkoxy, alkylsulphonyl, halogen, cyano, nitro, amino and carboxyl;

A is independently in each occurrence hydrogen, halogen or any suitable end-capping group;

j and l are independently in each occurrence 0 to 4;

k is independently in each occurrence 0 to 5;

a is the number of first monomer units and is greater than or equal to 1; and

b is the number of second monomer units, which may be 0.

7. The semiconductor composition according to claim 6 , wherein the polymeric semiconducting binder has alkoxy substituents directly substituted onto an aromatic ring in at least one of the 2, 4 and 6 positions.

8. The semiconductor composition according to claim 6 , wherein the polymeric semiconducting binder has a cyano group attached to the aromatic ring by means of a linker group.

9. The semiconductor composition according to claim 8 , wherein the cyano group attached to the aromatic ring by means of a linker group comprises at least one of:

wherein each R x is independently selected from hydrogen, an alkyl group, an alkoxy group, halogen, a nitro group or R y , where each R y is independently a cyano group (CN) or an organic group that includes at least one CN group.

10. The semiconductor composition according to claim 6 , wherein the polymeric semiconducting binder has at least one of alkoxy and cyano substitution on the pendant aromatic ring.

11. The semiconductor composition according to claim 6 , wherein the polymeric semiconducting binder has methoxy groups on the 2,4-positions of the pendant aromatic ring.

12. The semiconductor composition according to claim 1 , wherein the polymeric semiconducting binder comprises the copolymer:

wherein a is the number of first monomer units and is greater than or equal to 1; and

b is the number of second monomer units.

13. The semiconductor composition according to claim 1 , wherein the polymeric semiconducting binder is represented by at least one of the Formula (VII), (VIII), (IXa) and (IXb), wherein each Formula comprises at least one of first and second monomer units:

wherein each R x is independently selected from hydrogen, an alkyl group, an alkoxy group, halogen, a nitro group or R y , where each R y is independently a cyano group (CN) or an organic group that includes at least one CN group, and wherein at least one of the repeat units is substituted by cyano groups or by groups which comprise cyano groups or by alkoxy groups;

the sum of indices (j+k+l) is at least 1;

each R Z is independently an alkyl group optionally substituted by one or more substituents selected from hydroxyl, alkoxy, alkylsulphonyl, halogen, cyano, nitro, amino and carboxyl;

A is independently in each occurrence hydrogen, halogen or any suitable end-capping group;

j and l are independently in each occurrence 0 to 4;

k is independently in each occurrence 0 to 5;

a is the number of first monomer units and is greater than or equal to 1;

b is the number of second monomer units, which may be 0; and

each R a and R b is independently selected from hydrogen and optionally substituted alkyl, alkaryl, aralkyl, alkoxy and polyalkoyloxy groups.

14. The semiconductor composition according to claim 1 , wherein the triarylamine repeat units comprise at least one of (II e), (II f), (II g) and (II h):

wherein each R x is independently selected from hydrogen, an alkyl group, an alkoxy group, halogen, a nitro group or R y , where each R y is independently a cyano group (CN) or an organic group that includes at least one CN group, and wherein at least one of the repeat units is substituted by cyano groups or by groups which comprise cyano groups or by alkoxy groups;

the sum of indices (j+k+l) is at least 1;

each R z is independently an alkyl group optionally substituted by one or more substituents selected from hydroxyl, alkoxy, alkylsulphonyl, halogen, cyano, nitro, amino and carboxyl;

j and l are independently in each occurrence 0 to 4;

k is independently in each occurrence 0 to 5; and

each R a and R b is independently selected from hydrogen and optionally substituted alkyl, alkaryl, aralkyl, alkoxy and polyalkoyloxy groups.

15. The semiconductor composition according to claim 1 , wherein the soluble polyacene semiconductor is represented by at least one of the Formula (A2), (A3) and (C):

wherein R 1 , R 4 , R 8 and R 11 are methyl groups and R f are ethyl or isopropyl groups,

wherein R 2 , R 3 , R 9 , R 10 are methyl groups and R f are ethyl or isopropyl groups,

wherein one of Y 1 and Y 2 denotes —CH═ or ═CH— and the other denotes —X′—;

one of Y 3 and Y 4 denotes —CH═ or ═CH— and the other denotes —X′—;

X′ is —O—, —S—, —Se—, or —NR′″—;

R s is cyclic, straight chain or branched alkyl or alkoxy having 1 to 20 carbon atoms, or aryl having 2 to 30 carbon atoms, all of which are optionally fluorinated or perfluorinated;

R t is H, F, Cl, Br, I, CN, straight chain or branched alkyl or alkoxy having 1 to 20 carbon atoms and optionally being fluorinated or perfluorinated, optionally fluorinated or perfluorinated aryl having 6 to 30 carbon atoms, or CO 2 R″, with R″ being H, optionally fluorinated alkyl having 1 to 20 carbon atoms, or optionally fluorinated aryl having 2 to 30 carbon atoms;

R′″ is H or cyclic, straight chain or branched alkyl with 1 to 10 carbon atoms;

m is 0 or; and

n is 0 or 1.

16. The semiconductor composition according to claim 15 , wherein the soluble polyacene semiconductor is represented by at least one of the Formula (Cl) and (C2):

wherein X′, R t and R s are as defined in claim 15 .

17. The semiconductor composition according to claim 1 , wherein the polymeric semiconducting binder comprises the copolymer:

wherein a is the number of first monomer units and b is the number of second monomer units, and wherein the soluble polyacene semiconductor comprises 1,4,8,11-tetramethyl bis-triethylsilylethynyl pentacene.

18. An organic thin film transistor in which the source and drain electrodes are bridged by a semiconductor composition according to claim 1 .

19. A solution of an organic semiconducting composition according to claim 1 for use in a process of manufacturing organic thin film transistors, the process comprising depositing an organic semiconducting composition by solution coating.

20. A process of manufacturing organic thin film transistors, the process comprising:

depositing an organic semiconducting composition according to claim 1 by solution coating.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 3, 2023
From: NEUDRIVE LIMITED
To: SILVERRAY LTD.
Reel/Frame 064136/0459 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 14, 2019
From: WUHAN XINQU CHUANGROU OPTOELECTRONICS TECHNOLOGY CO., LTD.
To: NEUDRIVE LIMITED
Reel/Frame 047987/0664 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 13, 2018
From: NEUDRIVE LIMITED
To: WUHAN XINQU CHUANGROU OPTOELECTRONICS TECHNOLOGY CO., LTD.
Reel/Frame 046866/0990 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2015
From: CENTRE FOR PROCESS INNOVATION LIMITED
To: NEUDRIVE LIMITED
Reel/Frame 035880/0688 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2014
From: BROWN, BEVERLEY ANNE; OGIER, SIMON DOMINIC; PALUMBO, MARCO; MCCALL, KERI LAURA
To: CENTRE FOR PROCESS INNOVATION LIMITED
Reel/Frame 032049/0001 →
Priority Claims (4)
GB 1108864.8 · May 26, 2011 · national
GB 1118867.9 · Nov 1, 2011 · national
GB 1120997.0 · Dec 7, 2011 · national
GB 1205022.5 · Mar 22, 2012 · national
Continuity (1)
Related Publication 20140175409A1 · Jun 26, 2014