IP Library Granted Patent US 10,435,506
Granted Patent B2
US 10,435,506 · App. 15/573,257 · Granted Oct 8, 2019

Thiadiazolopyridine polymers, their synthesis and their use

Inventors: William Mitchell (Chandler's Ford, GB); Mansoor D'Lavari (Bude, GB)
Assignee: MERCK PATENT GMBH
C08G61/126C08G61/122C08G61/123C08G61/124C08G75/00C08G75/02C08G75/32C08G79/00C08K3/045C08L65/00H01L51/0036H01L51/0043H01L51/0094C08G2261/12C08G2261/122C08G2261/1412C08G2261/3241C08G2261/3243C08G2261/3246C08G2261/344C08G2261/414C08G2261/90C08G2261/91C08G2261/92C08G2261/94C08G2261/95H01L51/42H01L51/4253H01L51/50H01L51/5012H01L51/5056H01L51/5072H01L51/5096Y02E10/549Y02P70/521
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,435,506
App. No.
15/573,257
Granted
Oct 8, 2019
Kind
B2
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.

Claims (39)

1. A 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 (III), 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, selected from 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

the sum of the molar ratios 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 are independently of each other H or a carbyl group.

2. The polymer according to claim 1 , wherein at least 50% of the first monomer units M 1 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. The polymer according to claim 1 , wherein at least 50% of the second monomer units M 2 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. The polymer according to claim 1 , wherein at least 50% of the third monomer units M 3 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. The polymer according to claim 1 , wherein at least 50% of the fourth monomer units M 4 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. The polymer according to claim 1 , wherein said polymer comprises a sequence unit S 1 of formula (S-I)

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

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

9. The 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. The 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. The polymer according to claim 1 , wherein the first molar ratio m 1 is at least 0.10.

12. The 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. A charge transport, semiconducting, electrically conducting, photoconducting or light emitting material comprising a 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, thin film transistors, integrated circuits, logic circuits, capacitors, radio frequency identification tags, devices or components, organic light emitting diodes, organic light emitting transistors, flat panel displays, backlights of displays, organic photovoltaic devices, organic solar cells, photodiodes, laser diodes, photoconductors, organic photodetectors, 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, planarizing 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 , wherein said component or device is an organic photodetector.

17. The polymer according to claim 1 , wherein said polymer contains at least 50 wt % of monomer units M 1 to M 5 .

18. The polymer according to claim 1 , wherein m 1 =0 or m 2 =0 and m 3 is at least 0.10 and at most 0.80.

19. The polymer according to claim 1 , wherein m 4 is at least 0.01.

20. The polymer according to claim 1 , wherein m 5 is at least 0.15 and at most 0.85.

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

22. The polymer according to claim 1 , wherein the polymer has a molecular weight M n of at least 5,000 g/mol and at most 250,000 g/mol.

23. The polymer according to claim 1 , wherein said polymer does not contain monomer units of optionally substituted benzo[1,2-b;4,5-b′]dithiophene.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2023
From: FLEXENABLE LTD.
To: FLEXENABLE TECHNOLOGY LIMITED
Reel/Frame 064279/0813 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 7, 2023
From: MERCK PATENT GMBH
To: FLEXENABLE LTD.
Reel/Frame 063907/0525 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2017
From: MITCHELL, WILLIAM; D'LAVARI, MANSOOR
To: MERCK PATENT GMBH
Reel/Frame 044090/0952 →
Priority Claims (1)
EP 15167266 · May 12, 2015 · regional
Continuity (1)
Related Publication 20180105637A1 · Apr 19, 2018