P-type semiconducting polymers and related methods

Patent metadata

Field	Value
Publication number	US-10439141-B2
Application number	US-201715716303-A
Country	US
Kind code	B2
Filing date	Sep 26, 2017
Priority date	Dec 28, 2012
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

There is provided p-type organic polymers of general formula I. The polymers may be useful as semi-conducting material. Thus, thin films and devices comprising such polymers are also provided.

First claim

What is claimed is:

1. A polymer of formula I:

wherein:
Ar 1 and Ar 2 are either
(i) both absent, or
(ii) both present and
Ar 1 is selected from:

and Ar 2 is selected from:

Ar 3 is selected from

V is selected from O, S, N, Se, C—R 12 , C═C, C═N and N═C;
X and Y are each independently selected from O, S, Se and N;
W and Z are each independently selected from C—R 12 and N;
each occurrence of R 1 (of 2n total occurrences) is each independently selected from H, straight or branched alkyl having from 1 to 60 backbone atoms, straight or branched alkenyl having from 2 to 60 backbone atoms, straight or branched alkynyl having from 2 to 60 backbone atoms, straight or branched arylalkyl having from 6 to 60 backbone atoms, straight or branched arylalkenyl having from 7 to 60 backbone atoms, straight or branched arylalkynyl having from 7 to 60 backbone atoms, straight or branched alkoxy having from 2 to 60 backbone atoms, straight or branched alkenyloxy having from 3 to 60 backbone atoms, straight or branched alkynyloxy having from 3 to 60 backbone atoms, straight or branched arylalkoxy having from 7 to 60 backbone atoms, straight or branched arylalkenyloxy having from 8 to 60 backbone atoms, straight or branched arylalkynyloxy having from 8 to 60 backbone atoms, straight or branched alkylamino having from 2 to 60 backbone atoms, straight or branched alkenylamino having from 3 to 60 backbone atoms, straight or branched alkynylamino having from 3 to 60 backbone atoms, straight or branched arylalkylamino having from 7 to 60 backbone atoms, straight or branched arylalkenylamino having from 8 to 60 backbone atoms, straight or branched arylalkynylamino having from 8 to 60 backbone atoms, straight or branched ester having from 2 to 60 backbone atoms, straight or branched carbonyl having from 1 to 60 backbone atoms;
each occurrence of each of R, R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 (of m or 2m total occurrences) is each independently selected from straight or branched alkyl having from 1 to 60 backbone atoms, straight or branched alkenyl having from 2 to 60 backbone atoms, straight or branched alkynyl having from 2 to 60 backbone atoms, straight or branched arylalkyl having from 6 to 60 backbone atoms, straight or branched arylalkenyl having from 7 to 60 backbone atoms, straight or branched arylalkynyl having from 7 to 60 backbone atoms, straight or branched alkoxy having from 2 to 60 backbone atoms, straight or branched alkenyloxy having from 3 to 60 backbone atoms, straight or branched alkynyloxy having from 3 to 60 backbone atoms, straight or branched arylalkoxy having from 7 to 60 backbone atoms, straight or branched arylalkenyloxy having from 8 to 60 backbone atoms, straight or branched arylalkynyloxy having from 8 to 60 backbone atoms, straight or branched alkylamino having from 2 to 60 backbone atoms, straight or branched alkenylamino having from 3 to 60 backbone atoms, straight or branched alkynylamino having from 3 to 60 backbone atoms, straight or branched arylalkylamino having from 7 to 60 backbone atoms, straight or branched arylalkenylamino having from 8 to 60 backbone atoms, straight or branched arylalkynylamino having from 8 to 60 backbone atoms, straight or branched ester having from 2 to 60 backbone atoms, straight or branched carbonyl having from 1 to 60 backbone atoms;
each occurrence of R 2 , R 3 and R 12 (of n total occurrences) is each independently selected from H, halide, straight or branched alkyl having from 1 to 60 backbone atoms, straight or branched alkenyl having from 2 to 60 backbone atoms, straight or branched alkynyl having from 2 to 60 backbone atoms, straight or branched arylalkyl having from 6 to 60 backbone atoms, straight or branched arylalkenyl having from 7 to 60 backbone atoms, straight or branched arylalkynyl having from 7 to 60 backbone atoms, straight or branched alkoxy having from 2 to 60 backbone atoms, straight or branched alkenyloxy having from 3 to 60 backbone atoms, straight or branched alkynyloxy having from 3 to 60 backbone atoms, straight or branched arylalkoxy having from 7 to 60 backbone atoms, straight or branched arylalkenyloxy having from 8 to 60 backbone atoms, straight or branched arylalkynyloxy having from 8 to 60 backbone atoms, straight or branched alkylamino having from 2 to 60 backbone atoms, straight or branched alkenylamino having from 3 to 60 backbone atoms, straight or branched alkynylamino having from 3 to 60 backbone atoms, straight or branched arylalkylamino having from 7 to 60 backbone atoms, straight or branched arylalkenylamino having from 8 to 60 backbone atoms, straight or branched arylalkynylamino having from 8 to 60 backbone atoms, straight or branched ester having from 2 to 60 backbone atoms, straight or branched carbonyl having from 1 to 60 backbone atoms;
n is an integer from 10 to 1000; and
when Ar 3 is

m is 0 when Ar 1 and Ar 2 are both absent, or when Ar 1 and Ar 2 are both present, m is an integer from 1 to 1000 and the ratio of m:n is from about 0.01 to about 1;
and when Ar 3 is

Ar 1 and Ar 2 are both present, and m is an integer from 1 to 1000 and the ratio of m:n is from about 0.01 to about 1, wherein the polymer has formula I-6:

2. The polymer of claim 1 , wherein the polymer has one of the following formulas:

3. A thin film comprising the polymer of claim 1 .

4. An organic electronic device comprising a photoactive layer, the photoactive layer comprising the polymer of claim 1 .

5. The organic electronic device of claim 4 , wherein the device comprises an organic photovoltaic cell having normal or inverted architecture, an organic thin film transistor, a photodiode, a light-emission diode, or a sensor including a chemical sensor, a biosensor or a biochemical sensor.

6. The organic electronic device of claim 4 , further comprising a polymeric electrolyte interlayer between the photoactive layer and a cathode.

7. The organic electronic device of claim 6 , wherein the polymeric electrolyte interlayer comprises a polymer electrolyte selected from:

wherein in the above formulas for the polymer electrolyte, m and n are integers independently selected from 10 to 1000.

8. A process for forming a thin film, comprising:
dissolving the polymer of claim 1 in a halogen-free solvent having a dispersion parameter of about 18 to about 20, a hydrogen bonding parameter of about 2 to about 4, and a polarity parameter of about 0.5 to about 6.5 to form a solution;
applying the solution to a substrate; and
allowing the solution to dry to form a thin layer comprising the polymer.

Assignees

• Agency Science Tech & Res

Inventors

• Li Jun
• Ong Kok Haw
• Chen Zhikuan
• Zhao Yujun
• Lim Siew Lay
• Wong Ivy
• Yang Le
• Seah Kang Yee

Classifications

• C08G2261/3246

  containing nitrogen and sulfur as heteroatoms · CPC title

• C08G2261/3223

  containing one or more sulfur atoms as the only heteroatom, e.g. thiophene · CPC title

• C08G2261/91

  Photovoltaic applications · CPC title

• C08G2261/143

  Side-chains containing nitrogen · CPC title

• C08G75/32

  Polythiazoles; Polythiadiazoles · CPC title