Semiconducting compounds and devices incorporating same

• US 8,927,971 B2
• Filed: 04/06/2010
• Issued: 01/06/2015
• Est. Priority Date: 04/06/2009
• Status: Expired due to Fees

• Current Assignee: University Of Kentucky Research Foundation (University of Kentucky)
• Original Assignee: University Of Kentucky Research Foundation (University of Kentucky)
• Inventors: Watson, Mark D.
• Primary Examiner(s): Krylova, Irina
• Application Number:
  US12/755,308
• Publication Number:
  US 20100252112A1
• Time in Patent Office: 1,736 Days
• Field of Search: 528/310, 528/322
• US Class Current: 257/40
• CPC Class Codes: C08G 2261/3223 containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
• CPC Class Codes: C08G 2261/344 containing heteroatoms
• CPC Class Codes: C08G 2261/414 Stille reactions
• CPC Class Codes: C08G 2261/92 TFT applications
• CPC Class Codes: C08G 61/123 derived from five-membered heterocyclic compounds
• CPC Class Codes: C08G 61/126 with a five-membered ring containing one sulfur atom in the ring
• CPC Class Codes: C08G 73/0672 with only one nitrogen atom in the ring
• CPC Class Codes: C08G 73/10 Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
• CPC Class Codes: C09B 57/00 Other synthetic dyes of known constitution
• CPC Class Codes: C09B 57/08 Naphthalimide dyes; Phthalimide dyes
• CPC Class Codes: C09B 69/109 containing other specific dyes
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 30/30 comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
• CPC Class Codes: H10K 30/50 Photovoltaic [PV] devices
• CPC Class Codes: H10K 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/113 Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• CPC Class Codes: H10K 85/151 Copolymers
• CPC Class Codes: H10K 85/621 Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Disclosed are semiconducting compounds having one or more phthalimide units and/or one or more head-to-head (H-H) substituted biheteroaryl units. Such compounds can be monomeric, oligomeric, or polymeric, and can exhibit desirable electronic properties and possess processing advantages including solution−processability and/or good stability at ambient conditions.

Claims

1. An electionic, optical or optoelectronic device comprising a semiconductor component, wherein the semiconductor component comprises a p-type semiconductor consisting of a polymeric compound having a degree of polymerization in the range of 10 to 10,000, wherein the polymeric compound is a copolymer consisting of a first repeating unit:

2. The electronic, optical or optoelectronic device according to claim 1 configured as a thin film transistor comprising a substrate, a source electrode, a drain electrode a gate electrode a gate dielectric component, and the semiconductor component wherein the semiconductor component is in contact with the source electrode and the drain electrode, and the gate dielectric component is in contact with the semiconductor component on one side and the gate electrode on an opposite side.

3. The electronic, optical or optoelectronic device according to claim 1 configured as a photovoltaic device comprising a substrate an anode, a cathode, and the semiconductor component disposed between the anode and the cathode.

4. The device of claim 3, wherein the semiconductor component is photoactive and comprises a blend material comprising one or more fullerene derivatives.

5. The device of claim 1, wherein the second repeating unit is selected from the group consisting of:

6. The device of claim 1, wherein R¹ is a linear C_1-40 alkyl group, a linear C_1-40 haloalkyl group, or a branched group selected from the group consisting of:

7. An electronic, optical or optoelectronic device comprising a semiconductor component, wherein the semiconductor component comprises a p-type semiconductor consisting of a polymeric compound having a degree of polymerization in the range of 10 to 10,000, wherein the polymeric compound consists of the repeating units:

8. The device of claim 7, wherein R¹ is a linear C_1-40 alkyl group, a linear C_1-40 haloalkyl group, or a branched group selected from the group consisting of:

9. The electronic, optical or optoelectronic device according to claim 7 configured as a thin film transistor comprising a substrate, a source electrode, a drain electrode, a gate electrode, a gate dielectric component, and the semiconductor component, wherein the semiconductor component is in contact with the source electrode and the drain electrode, and the gate dielectric component is in contact with the semiconductor component on one side and the gate electrode on an opposite side.

10. The electronic, optical or optoelectronic device according to claim 7 configured as a photovoltaic device comprising a substrate, an anode, a cathode, and the semiconductor component disposed between the anode and the cathode.

11. The device of claim 10, wherein the semiconductor component is photoactive and comprises a blend material comprising one or more fullerene derivatives.

12. An electionic, optical or optoelectionic device comprising a semiconductor component, wherein the semiconductor component comprises a p-type semiconductor consisting of a polymeric compound having a degree of polymerization in the range of 10 to 10,000, wherein the polymeric compound consists of repeating units selected from the group consisting of:

13. The electronic, optical or optoelectronic device according to claim 12 configured as a thin film transistor comprising a substrate, a source electrode, a drain electrode, a gate electrode, a gate dielectric component, and the semiconductor component, wherein the semiconductor component is in contact with the source electrode and the drain electrode, and the gate dielectric component is in contact with the semiconductor component on one side and the gate electrode on an opposite side.

14. The electronic, optical or optoelectronic device according to claim 12 configured as a photovoltaic device comprising a substrate, an anode, a cathode, and the semiconductor component disposed between the anode and the cathode.

15. The device of claim 14, wherein the semiconductor component is photoactive and comprises a blend material comprising one or more fullerene derivatives.