Title: Bay-annulated indigo (BAI) as an excellent electron accepting building block for high performance organic semiconductors

Abstract

A novel electron acceptor based on bay-annulated indigo (BAI) was synthesized and used for the preparation of a series of high performance donor-acceptor small molecules and polymers. The resulting materials possess low-lying LUMO energy level and small HOMO-LUMO gaps, while their films exhibited high crystallinity upon thermal treatment, commensurate with high field effect mobilities and ambipolar transfer characteristics.

Inventors:

Liu, Yi; He, Bo; Pun, Andrew

Issue Date:

2016-04-19

Research Org.:

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Org.:

USDOE

OSTI Identifier:

1248011

Patent Number(s):

9315671

Application Number:

14/942,775

Assignee:

The Regents of the University of California (Oakland, CA)

Patent Classifications (CPCs):

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS

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H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES

H01L51/0074 - {comprising only sulfur in the heteroaromatic polycondensed ringsystem, e.g. benzothiophene}
H01L51/0035 - {comprising aromatic, heteroaromatic, or arrylic chains, e.g. polyaniline
H01L51/0558 - {characterised by the channel of the transistor}

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS

C07D471/22 - in which the condensed systems contains four or more hetero rings

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES

H01L51/0094 - {Silicon-containing organic semiconductors}

C - CHEMISTRY C09 - DYES C09B - ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS},

C09B7/02 - Bis-indole indigos

H - ELECTRICITY H01 - BASIC ELECTRIC ELEMENTS H01L - SEMICONDUCTOR DEVICES

H01L51/0068 - {comprising only sulfur as heteroatom}
H01L51/0036 - {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
H01L51/0072 - {comprising only nitrogen in the heteroaromatic polycondensed ringsystem, e.g. phenanthroline, carbazole}

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DOE Contract Number:  

AC02-05CH11231

Resource Type:

Patent

Resource Relation:

Patent File Date: 2015 Nov 16

Country of Publication:

United States

Language:

English

Subject:

36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 14 SOLAR ENERGY