Thiadiazolopyridine polymers, their synthesis and their use

Patent metadata

Field	Value
Publication number	US-2018105637-A1
Application number	US-201615573257-A
Country	US
Kind code	A1
Filing date	Apr 27, 2016
Priority date	May 12, 2015
Publication date	Apr 19, 2018
Grant date	—

Abstract

The present invention relates to thiadiazolopyridine polymers, their synthesis and their use. The present invention further relates to organic electronic devices comprising such thiadiazolopyridine polymers.

First claim

1 . Polymer comprising
(i) a first monomer unit M 1 of formula (I) in a first molar ratio m 1 ;

(ii) a second monomer unit M 2 of formula (II) in a second molar ratio m 2 ;

(iii) one or more third monomer units M 3 , each being independently of each other selected from the group consisting of formula (II), formula (IV), formula (V), and formula (VI), in a third molar ratio m 3 ,

(iv) one or more fourth monomer units M 4 , each independently of the other, one or more electron donors comprising a group selected from the group consisting of aryl, heteroaryl, ethene-2,1-diyl(*—(R 81 )C═C(R 82 )—*) and ethyndiyl (*—C≡C—*), wherein such aryl or heteroaryl group is different from formulae (I) to (VI), in a fourth molar ratio m 4 ,
and

(v) a fifth monomer unit M 5 of formula (VII) in a fifth molar ratio m 5 ,

wherein, independently at each occurrence, one of X 1 and X 2 is N and the other is C—R 71 , and X 3 is at each occurrence independently selected from the group consisting of O, S, Te, Se and N—R 91 ,

wherein the sum of first molar ratio m 1 and second molar ratio m 2 is at least 0.10 and at most 0.90, the third molar ratio m 3 is at least 0 and at most 0.80, the fourth molar ratio m 4 is at least 0 and at most 0.20, the fifth molar ratio m 5 is at least 0.10 and at most 0.90, and m 1 +m 2 +m 3 +m 4 +m 5 =1, with the respective molar ratios m 1 to m 5 being relative to the total number of monomer units M 1 to M 5 , and
wherein, independently at each occurrence, R 11 to R 14 , R 21 to R 24 , R 31 to R 34 , R 41 to R 43 , R 51 to R 58 , R 61 to R 68 , R 71 , R 81 to R 82 and R 91 ae independently of each other H or a carbyl group.

2 . Polymer according to claim 1 , wherein at least 50% of the first monomer units M 1 , which are comprised in the polymer, are comprised in a first sequence unit S 1 , wherein the first monomer unit M 1 is adjacent to at least one monomer unit of formula (VII).

3 . Polymer according to claim 1 , wherein at least 50% of the second monomer units M 2 , which are comprised in the polymer, are comprised in a second sequence unit S 2 , wherein the second monomer unit M 2 is adjacent to at least one monomer unit of formula (VII).

4 . Polymer according to claim 1 , wherein at least 50% of the third monomer units M 3 , which are comprised in the polymer, are comprised in a third sequence unit S 3 , wherein the third monomer unit M 3 is adjacent to at least one monomer unit of formula (VII).

5 . Polymer according to claim 1 , wherein at least 50% of the fourth monomer units M 4 , which are comprised in the polymer, are comprised in a fourth sequence unit S 4 , wherein the fourth monomer unit M 4 is adjacent to at least one monomer unit of formula (VII).

6 . Polymer according to claim 1 , wherein said polymer comprises a sequence unit S 1 of formula (S-I).

7 . Polymer according to claim 1 , wherein said polymer comprises a second sequence unit S 2 of formula (S-II).

8 . Polymer according to claim 1 , wherein said polymer comprises one or more third sequence units S 3 independently of each other selected from the group consisting of formula (S-III), formula (S-IV), formula (S-V), and formula (S-VI).

9 . Polymer according to claim 1 , wherein said polymer comprises one or more fourth sequence unit S 4 of formula (S-VII)

wherein M 4 is at each occurrence independently as defined above.

10 . Polymer according to claim 1 , wherein for m 3 >0 the ratio (m 1 +m 2 )/m 3 is at least 1 and at most 100.

11 . Polymer according to claim 1 , wherein the first molar ratio m 1 is at least 0.10.

12 . Polymer according to claim 1 , wherein if m 1 =0 or m 2 =0 then m 3 is at least 0.10 and at most 0.80

13 . A mixture or a blend comprising one or more polymers of claim 1 , and one or more compounds or polymers selected from the group consisting of binders and compounds or polymers having semiconducting, charge transport, hole transport, electron transport, hole blocking, electron blocking, electrically conducting, photoconducting or light emitting properties.

14 . Charge transport, semiconducting, electrically conducting, photoconducting or light emitting material comprising the polymer of claim 1 .

15 . A component or device comprising the polymer of claim 1 , said component or device being selected from the group consisting of organic field effect transistors (OFET), thin film transistors (TFT), integrated circuits (IC), logic circuits, capacitors, radio frequency identification (RFID) tags, devices or components, organic light emitting diodes (OLED), organic light emitting transistors (OLET), flat panel displays, backlights of displays, organic photovoltaic devices (OPV), organic solar cells (O-SC), photodiodes, laser diodes, photoconductors, organic photodetectors (OPD), electrophotographic devices, electrophotographic recording devices, organic memory devices, sensor devices, charge injection layers, charge transport layers or interlayers in polymer light emitting diodes (PLEDs), Schottky diodes, planarising layers, antistatic films, polymer electrolyte membranes (PEM), conducting substrates, conducting patterns, electrode materials in batteries, alignment layers, biosensors, biochips, security markings, security devices, and components or devices for detecting and discriminating DNA sequences.

16 . A component or device according to claim 15 , said component or device being an organic photodetector (OPD).

Assignees

• Merck Patent Gmbh

Inventors

• Mitchell William
• D'Lavari Mansoor

Classifications

• C08G75/32

  Polythiazoles; Polythiadiazoles · CPC title

• C08G2261/122

  statistical · CPC title

• C08G2261/3243

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

• C08G2261/92

  TFT applications · CPC title

• C08G75/00

  Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule · CPC title