# US 9,040,655 B2 · Direct CH arylation method using palladium-based catalyst

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- Number: US 9,040,655 B2
- Document ID: US9040655B2
- Status: Granted
- Kind: B2
- Application number: 14/129,828
- Filed: 2012-11-20
- Published: 2014-05-22
- Granted: 2015-05-26
- Earliest claimed: 2011-11-21
- Assignees: Gwangju Institute of Science and Technology
- Applicants: Gwangju Institute of Science and Technology
- Inventors: Jae-Suk Lee; Ashraf A El-Shehawy; Joon-Keun Min; Abdo Nabiha Ibrahim Mahmoud Mahamed
- Web page: https://patentgrep.com/patent/US9040655B2

## CPC

- C08G 61/122: {derived from five- or six-membered heterocyclic compounds, other than imides}
- B01J 31/2239: {Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands}
- C08F 234/04: in a ring containing sulfur
- C08G 61/126: {with a five-membered ring containing one sulfur atom in the ring}
- H10K 85/113: {Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene}
- H10K 85/151: {Copolymers}
- B01J 2231/4211: Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
- B01J 2531/824: Palladium
- C08G 2261/124: alternating
- C08G 2261/1412: Saturated aliphatic units
- 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 2261/3243: containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
- C08G 2261/364: containing hetero atoms
- C08G 2261/413: Heck reactions
- C08G 2261/414: Stille reactions
- C08G 2261/92: TFT applications
- H10K 10/466: {Lateral bottom-gate IGFETs comprising only a single gate}
- H10K 30/50: Photovoltaic [PV] devices
- Y02E 10/542: Dye sensitized solar cells
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A method for producing a copolymer includes reacting a first monomer with a second monomer using a Pd-based catalyst, wherein the first monomer is a first hetero cyclic compound which includes a first hetero atom selected from S, N, and O, the first hetero cyclic compound in which a carbon atom adjacent to the first hetero atom is coupled with at least one hydrogen atom, and the second monomer is a second hetero cyclic compound which includes a second hetero atom selected from S, N, and O, the second hetero cyclic compound in which the second hetero atom is coupled with a carbon atom in which a halogen group selected from Br, Cl, and I is substituted.

## Claims

### Claim 1

A method for producing a copolymer including reacting a first monomer with a second monomer using a Pd-based catalyst, wherein
the first monomer is a first hetero cyclic compound which includes a first hetero atom selected from S, N, and O, the first hetero cyclic compound in which a carbon atom adjacent to the first hetero atom is coupled with at least one hydrogen atom, and
the second monomer is a second hetero cyclic compound which includes a Chemical Formula
where Y is selected from S, N, and O; X, X′ are each independently selected from Br, Cl, and I; and R″ represents a phenyl group.

### Claim 2

A method for producing a copolymer of the following Chemical Formula 10 including reacting a first monomer with a second monomer using a Pd-based catalyst, wherein the first monomer is a compound of the following Chemical Formula 3; and the second monomer is selected from compounds of the following Chemical Formulas 5 to 9 or a mixture thereof,
in the Chemical Formula 10, the A has a structure of the following Chemical Formula 13; the B is selected from the following Chemical Formulas 15 to 19 or a combination thereof; mark * represents a coupled portion; and the n is an integer of 30 to 500,
in the Chemical Formulas, Y, Y′ are each selected from S, O, and N independently; the R, R′ each are an alkyl group of C1 to C6 independently; the R″ represents a phenyl group; the X, X′ are each selected from Br, Cl, and I independently; the m is an integer of 1 to 4; the Z is selected from Si, C, and N; the Ar represents benzene; and the X and X′ coupled with the Ar is coupled at position 1,3- or position 1,4- of the Ar.

### Claim 3 (depends on 1)

The method of claim 1, wherein the Pd-based catalyst is Pd(OAc)2.

### Claim 4 (depends on 1)

The method of claim 1, wherein the reaction is performed within N,N-dimethylformamide including potassium acetate (KOAc) and t-Bu4NBr.