# US 8,772,443 B2 · Water soluble near infrared sensing polymers with low band gaps

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- Number: US 8,772,443 B2
- Document ID: US8772443B2
- Status: Granted
- Kind: B2
- Application number: 13/580,799
- Filed: 2011-03-28
- Published: 2012-12-20
- Granted: 2014-07-08
- Earliest claimed: 2010-03-26
- Assignees: Hitachi Chemical Company, Ltd.; Hitachi Chemical Research Center, Inc.
- Applicants: Cuihua Xue
- Inventors: Cuihua Xue
- Web page: https://patentgrep.com/patent/US8772443B2

## CPC

- C08G 61/122: {derived from five- or six-membered heterocyclic compounds, other than imides}
- C08G 61/123: {derived from five-membered heterocyclic compounds}
- C08G 61/126: {with a five-membered ring containing one sulfur atom in the ring}
- C09K 11/06: containing organic luminescent materials
- C08G 2261/1424: containing ether groups, including alkoxy
- C08G 2261/1426: containing carboxy groups (COOH) and/or -C(=O)O-moieties
- C08G 2261/3223: containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
- C08G 2261/3241: containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
- C08G 2261/3246: containing nitrogen and sulfur as heteroatoms
- C08G 2261/94: Applications in sensors, e.g. biosensors
- C09K 2211/1458: containing sulfur as the only heteroatom
- C09K 2211/1483: containing nitrogen and sulfur as heteroatoms
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/151: {Copolymers}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present invention is directed to polymeric materials including a copolymer of at least a first and second monomer that have desirable electrical and optical properties, such as a low band gap and near infrared (NIR) absorption, respectively. More specifically, the present invention is directed to polymeric materials with charge neutrality that display increased solubility in aqueous media while retaining their electrical and optical properties. The polymeric materials in accordance with the present invention can be modified with any desired functional group to tailor the polymer materials for a specific application. Also described are methods of making the polymeric materials in accordance with the present invention.

## Claims

### Claim 1

A polymeric material comprising: a copolymer of
a first monomer (1), (2) or (3); and
a second monomer (4), (5), (6) or (7);
wherein,
wherein
R1=OH, Br, I, Cl, SH, COOH, NH2, N(R2)3 (R2 can be same or different), SR2, SR2COOH, SR2NH2, SR2SO3H, SR2SH, SR2OH, malemide, or NHS ester,
X=C0-C3 alkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl,
R2=Alkyl, aryl or heteroaryl, substituted aryl or substituted heteroaryl; and
n=0, 1, or an integer greater than 1; and
wherein R3 and R4=H or

### Claim 2 (depends on 1)

The polymeric material of claim 1, further comprising a third monomer (11), (12), (13), (14), (15), (16), (17), (18), or (19); wherein:
wherein R3 and R4=H or

### Claim 3 (depends on 1)

A polymeric material of claim 1 comprising: a copolymer of
a first monomer (8), (9) or (10); and
the second monomer (4), (5), (6) or (7);
wherein,
wherein
R1=OH, Br, I, Cl, SH, COOH, NH2, N(R2)3 (R2 can be same or different), SR2, SR2COOH, SR2NH2, SR2SOH, SR2SH, SR2OH, malemide, or NHS ester,
X=C0-C3 alkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl, and
R′=Alkyl, aryl, heteroaryl, substituted aryl or substituted heteroaryl.

### Claim 4 (depends on 3)

The polymeric material of claim 3, further comprising a third monomer (11), (12), (13), (14), (15), (16), (17), (18), or (19); wherein:
wherein R3 and R4=H or

### Claim 5 (depends on 1)

The polymeric material of claim 1, further comprising at least one functional unit.

### Claim 6 (depends on 5)

The polymeric material of claim 5, wherein the at least one functional unit comprises one or more of: carbohydrates, proteins, peptides, DNA, RNA, antibodies, antigens, enzymes, bacteria, redox molecules, host molecules, guest molecules, haptens, lipids, microbes, sugars and aptamers.

### Claim 7 (depends on 5)

The polymeric material of claim 5, wherein the polymeric material comprises at least one of the following:
wherein:
R1=OH, Br, I, Cl, SH, COOH, NH2, N(R2)3 (R2 can be same or different), SR2, SR2COOH, SR2NH2, SR2SO3H, SR2SH, SR2OH, malemide, or NHS ester,
X=C0-C3 alkyl, aryl, substituted aryl, heteroaryl, or substituted heteroaryl,
R2=alkyl, aryl or heteroaryl, substituted aryl, substituted heteroaryl, and
Y=one or more of carbohydrates, proteins, peptides, DNA, RNA, antibodies, antigens, enzymes, bacteria, redox molecules, host molecules, guest molecules, haptens, lipids, microbes, sugars and aptamers.

### Claim 8 (depends on 4)

A polymeric material comprising a self-polymerized product of one of the monomers (1)-(19) as defined by claim 4.

### Claim 9 (depends on 7)

The polymeric material of claim 7, wherein an absorption spectrum of the material comprises a maximum wavelength absorption of at least 600 nm.