Novel dihydropyrrolo[2,3-f] indole-diketopyrrolopyrrole semiconducting materials, and methods and uses thereof

Patent metadata

Field	Value
Publication number	US-2016365518-A1
Application number	US-201615248164-A
Country	US
Kind code	A1
Filing date	Aug 26, 2016
Priority date	Feb 28, 2014
Publication date	Dec 15, 2016
Grant date	—

Abstract

Described herein are heterocyclic organic compounds. More specifically, described herein are compounds based on the combination of fused pyrrole structures with diketopyrrolopyrrole structures, methods for making these compounds, and uses thereof. The compounds disclosed have improved electronic, polymerization and stability properties that allow for improved material processibility and inclusion in organic semiconductor devices.

First claim

What is claimed is:

1 . A compound of formula:

wherein Ar is an optionally substituted aromatic or heteroaromatic group or conjugated group; k is an integer from 0 to 5 with the proviso that when k is 0, the structure results in a direct bond between the thiophene and pyrrole group; each X is independently NR 1 , PR 1 , AsR 1 , Sb, O, S, Te, or Se, with the proviso that due to conjugation, X may be bonded to one or more additional R 1 ; each Y is independently H, halo, trialkylsilane, optionally substituted C 1 -C 40 alkyl, optionally substituted aralkyl, alkoxy, alkylthio, optionally substituted C 2 -C 40 alkenyl, optionally substituted C 2 -C 40 alkynyl, aminocarbonyl, acylamino, acyloxy, aryl, aryloxy, optionally substituted amino, carboxyalkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, halo, acyl, optionally substituted heteroaryl, optionally substituted heteroaralkyl, heteroaryloxy, optionally substituted heterocyclyl, thiol, alkylthio, heteroarylthiol, optionally substituted sulfoxide, optionally substituted sulfone, OSO-alkyl, Mg-halo, Zn-halo, Sn(alkyl) 3 , SnH 3 , B(OH) 2 , B(alkoxy) 2 , or OTs; and each R, R 1 , R 2 , and R 3 is independently H, halo, optionally substituted C 1 -C 40 alkyl, optionally substituted aralkyl, alkoxy, alkylthio, optionally substituted C 2 -C 40 alkenyl, optionally substituted C 2 -C 40 alkynyl, aminocarbonyl, acylamino, acyloxy, optionally substituted aryl, aryloxy, optionally substituted amino, carboxyalkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, acyl, optionally substituted heteroaryl, optionally substituted heteroaralkyl, heteroaryloxy, optionally substituted heterocyclyl, thiol, alkylthio, heteroarylthiol, optionally substituted sulfoxide, or optionally substituted sulfone.

2 . The compound of claim 1 , wherein the compound comprises structure 1a or 1b.

3 . The compound of claim 1 , wherein the compound comprises structure 1c, 1d, or 1e.

4 . The compound of claim 1 , wherein the compound comprises structure 2.

5 . The compound of claim 1 , wherein k is from 0-3.

6 . The compound of claim 5 , wherein k is 0.

7 . The compound of claim 1 , wherein Ar is an optionally substituted aryl or heteroaryl.

8 . The compound of claim 1 , wherein Ar is a thiophene or fused thiophene.

9 . The compound of claim 8 , wherein the thiophene or fused thiophene is bonded to compound via the α positions and optionally substituted with one or more C 1 -C 20 alkyl groups at the β positions.

10 . The compound of claim 1 , wherein X is N, S, or O.

11 . The compound of claim 1 , wherein Y is H, optionally substituted alkyl, or halo.

12 . The compound of claim 1 , wherein each R 1 and R 3 are independently H, optionally substituted alkyl, halo, optionally substituted alkoxy, optionally substituted alkylthiol, or optionally substituted alkenyl.

13 . The compound of claim 12 , wherein each R and R 2 are independently H, optionally substituted alkyl, halo, or optionally substituted alkoxy.

14 . A method of making a compound of claim 1 , the method comprising reacting a compound of structure:

with a compound of structure:

where X is halo and Z is H or an optionally substituted alkyl.

15 . The method of claim 14 , wherein k is from 0-3.

16 . The method of claim 14 , wherein Ar is an optionally substituted aryl or heteroaryl.

17 . The method of claim 1 , wherein X is N, S, or O.

18 . The method of claim 1 , wherein each R 1 and R 3 are independently H, optionally substituted alkyl, halo, optionally substituted alkoxy, optionally substituted alkylthiol, or optionally substituted alkenyl.

19 . The method of claim 18 , wherein each R and R 2 are independently H, optionally substituted alkyl, halo, or optionally substituted alkoxy.

20 . The method of claim 14 , wherein k is from 0-3, Ar is a thiophene or fused thiophene, X is N, S, or O, Y is H, optionally substituted alkyl, or halo, and each R 1 and R 3 are independently H, optionally substituted alkyl, halo, optionally substituted alkoxy, optionally substituted alkylthiol, or optionally substituted alkenyl.

Assignees

• Corning Inc

Inventors

• He Mingqian
• Hu Jieyu
• Tandia Adama

Classifications

• C08G2261/344

  containing heteroatoms · CPC title

• C08G2261/3243

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

• C08G61/126 Primary

  with a five-membered ring containing one sulfur atom in the ring · CPC title