Semiconducting compounds and optoelectronic devices incorporating same

Patent metadata

Field	Value
Publication number	US-9312501-B2
Application number	US-201313843633-A
Country	US
Kind code	B2
Filing date	Mar 15, 2013
Priority date	Sep 28, 2012
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

Abstract

Disclosed are new compounds having semiconducting properties. Such compounds can be processed in solution-phase into thin film semiconductors that exhibit high carrier mobility and/or good current modulation characteristics.

First claim

The invention claimed is:

1. A compound represented by formula I:

wherein:
Ar is an optionally substituted C 6-20 aryl group or an optionally substituted 5-20 membered heteroaryl group;
Ar′ is an optionally substituted C 6-20 aryl group or an optionally substituted 5-20 membered heteroaryl group;
R 1 and R 2 , at each occurrence, independently are selected from the group consisting of a halogen, —CN, and -L-R, wherein L, at each occurrence, is selected from —O—, —S—, —Se—, —C(O)—, —OC(O)—, —C(O)O—, and a covalent bond; and R, at each occurrence, independently is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group;
X is selected from the group consisting of —O—, —S—, and —Se—;
X′ is —CR 3 , wherein R 3 is selected from the group consisting of H, a halogen, —CN, and -L′-R′, wherein L′ is selected from the group consisting of —O—, —S—, —Se—, —C(O)—, —OC(O)—, —C(O)O—, and a covalent bond; and R′ is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group;
Y and Y′, independently, are CH or N;
m is 0, 1, 2, 3, 4 or 5;
n is 0, 1, 2, 3 or 4; and
p is 0 or 1.

2. The compound of claim 1 , wherein X is S or Se.

3. The compound of claim 1 , wherein the compound is represented by formula II:

wherein Ar, Ar′, R 1 , R 2 , Y, Y′, m, n and p are as defined in claim 1 .

4. The compound of claim 1 , wherein the compound is represented by formula III:

wherein Ar, Ar′, R 2 , m and p are as defined in claim 1 .

5. The compound of claim 1 , wherein the compound is represented by formula IV:

wherein:
Ar 1 is an optionally substituted C 6-14 aryl group or an optionally substituted 5-14 membered heteroaryl group;
W is selected from the group consisting of —CR 3 ═CR 3 —, —O—, —S—, and —Se—;
W′ is —CR 3 ═ or —N═; and
R 2 , R 3 , and m are as defined in claim 1 .

6. The compound of claim 5 , wherein the compound is represented by formula V:

wherein Ar 1 , R 2 , and m are as defined in claim 5 .

7. The compound of claim 6 , wherein the moiety

is selected from the group consisting of:

wherein:
V″, at each occurrence, independently is —CR 4 ═ or —N═;
Z, at each occurrence, independently is selected from the group consisting of —O—, —S—, and —Se—;
Z′, at each occurrence, independently is —CR 4 ═ or —N═; and
R 4 , at each occurrence, independently is selected from the group consisting of H, a halogen, —CN, and L′R′, wherein L′, at each occurrence, is selected from the group consisting of —O—, —S—, —Se—, —C(O)—, —OC(O)—, —C(O)O—, and a covalent bond; and R′, at each occurrence, independently is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group.

8. The compound of claim 7 , wherein the moiety

is selected from the group consisting of:

wherein any of the carbon atoms optionally is substituted with a halogen, —CN, or -L′-R′, wherein L′, at each occurrence, is selected from the group consisting of —O—, —S—, —Se—, —C(O)—, —OC(O)—, —C(O)O—, and a covalent bond; and R′, at each occurrence, independently is selected from the group consisting of a C 1-40 alkyl group, a C 2-40 alkenyl group, a C 2-40 alkynyl group, and a C 1-40 haloalkyl group.

9. The compound of claim 1 , wherein the compound has a formula selected from the group consisting of:

wherein R 2 and m are as defined in claim 1 .

10. The compound of claim 9 , wherein R 2 is a C 1-40 alkyl group or a C 1-40 haloalkyl group; and m is 0, 1 or 2.

11. An electronic, optical or optoelectronic device comprising a semiconductor component, the semiconductor component comprising a compound according to claim 1 .

12. The device of claim 11 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as an electron-conducting compound and is present in a blend material.

13. The device of claim 11 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as a hole-conducting compound and is present in a blend material.

14. The device of claim 11 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as an light-emitting compound and is present in a blend material.

15. The device of claim 11 configured as an organic light emitting diode comprising a substrate, an anode, a cathode, and in between the anode and the cathode the semiconductor component.

16. The device of claim 11 configured as an organic transistor, further comprising a source electrode, a drain electrode, a gate electrode, and a dielectric layer, wherein the dielectric layer is in contact with the semiconductor component on one surface, and the gate electrode on an opposite surface.

17. The device of claim 16 , wherein the organic transistor is an organic field-effect transistor.

18. The device of claim 16 , wherein the organic transistor is an organic light-emitting transistor.

19. The device of claim 18 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as an electron-conducting compound or a hole-conducting compound and is present in a blend material.

20. The device of claim 18 , wherein the semiconductor component is photoactive, and wherein the compound of claim 1 functions as an light-emitting compound and is present in a blend material.

Assignees

• Polyera Corp

Inventors

• Usta Hakan
• Denti Mitchell
• Sheets William Christopher
• Facchetti Antonio

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H05B33/10

  Apparatus or processes specially adapted to the manufacture of electroluminescent light sources · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title