IP Library Granted Patent US 10,333,072
Granted Patent B2
US 10,333,072 · App. 15/506,802 · Granted Jun 25, 2019

Thin film semiconductor comprising a small-molecular semiconducting compound and a non-conductive polymer

Inventors: Thomas Weitz (Mannheim, DE); Thomas Gessner (Heidelberg, DE); Junichi Takeya (Kashiwa, JP); Masayuki Kishi (Ichikawa, JP)
Assignee: BASF SE
H01L51/0053C07D471/06H01L51/004H01L51/0566
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Quick Facts
Patent No.
US 10,333,072
App. No.
15/506,802
Granted
Jun 25, 2019
Kind
B2
Abstract

A thin film semiconductor comprising a compound of formula I or II wherein: R 1 and R 2 , at each occurrence, independently are selected from a C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group and a C 1-30 haloalkyl group, R 3 , R 4 , R 5 , and R 6 independently are H or an electron-withdrawing group, wherein at least one of R 3 , R 4 , R 5 , and R 6 is an electron-withdrawing group; and a non-conductive polymer.

Claims (24)

1. A thin film semiconductor comprising a compound of the following formula I or II:

wherein:

R 1 and R 2 , at each occurrence, independently are selected from the group consisting of a C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group, and a C 1-30 haloalkyl group,

R 3 , R 4 , R 5 , and R 6 independently are H or an electron-withdrawing group, wherein at least one of R 3 , R 4 , R 5 , and R 6 is an electron-withdrawing group; and

a non-conductive polymer,

wherein the non-conductive polymer is poly(methylmethacrylate), and

wherein a weight ratio of the compound of the formula I or II to the non-conductive polymer in the thin film semiconductor is from 5:1 to 1:5.

2. The thin film semiconductor of claim 1 , wherein R 1 and R 2 , at each occurrence, are selected from the group consisting of a C 1-12 alkyl group and a C 1-12 haloalkyl group.

3. The thin film semiconductor of claim 1 , wherein each of R 3 , R 4 , R 5 , and R 6 is selected from the group consisting of H, F, Cl, Br, I, and —CN.

4. The thin film semiconductor of claim 1 , wherein each of R 3 and R 4 is Br or CN and R 5 and R 6 are H.

5. The thin film semiconductor of claim 1 , wherein each of R 3 and R 6 is Br or —CN and R 4 and R 5 are H.

6. The thin film semiconductor of claim 1 , wherein the compound has the following formula Ia or formula Ib:

wherein R′, R″ are, at each occurrence, selected from the group consisting of a C 1-12 alkyl group and a C 1-12 haloalkyl group, and

R 3 , R 4 , and R 6 are as defined in claim 1 .

7. The thin film semiconductor of claim 1 , wherein the compound of the formula I is

8. The thin film semiconductor of claim 1 , wherein the compound of formula II is

9. A solution comprising at least one compound of the following formula I or II:

wherein:

R 1 and R 2 each independently, are selected from the group consisting of a C 1-30 alkyl group, a C 2-30 alkenyl group, a C 2-30 alkynyl group, and a C 1-30 haloalkyl group,

R 3 , R 4 , R 5 , and R 6 each independently, are H or an electron-withdrawing group, wherein at least one of R 3 , R 4 , R 5 , and R 6 is an electron-withdrawing group,

a non-conductive organic polymer, and

a solvent,

wherein the non-conductive organic polymer is poly(methylmethacrylate), and

wherein a weight ratio of the compound of the formula I or II to the non-conductive organic polymer in the solution is from 5:1 to 1:5.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2020
From: BASF SE
To: CLAP CO., LTD.
Reel/Frame 052459/0201 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 13, 2018
From: THE UNIVERSITY OF TOKYO
To: BASF SE
Reel/Frame 046069/0626 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2018
From: WEITZ, THOMAS; GESSNER, THOMAS
To: BASF SE
Reel/Frame 044662/0183 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 19, 2018
From: TAKEYA, JUNICHI; KISHI, MASAYUKI
To: UNIVERSITY OF TOKYO
Reel/Frame 044662/0194 →
Priority Claims (1)
EP 14182710 · Aug 28, 2014 · regional
Continuity (1)
Related Publication 20170244045A1 · Aug 24, 2017