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Method of forming polyaryl polymers and polymers formed thereby

a polyaryl polymer and polymerization method technology, applied in the field of polyaryl polymerization and polymerization field, can solve the problems of increasing cost and complexity of the polymerization process, synthesis and handling of aryl mesylates, tosylates, and triflates

Inactive Publication Date: 2017-02-23
DOW GLOBAL TECH LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This approach provides a more convenient and cost-effective method for producing polyaryl polymers, reducing the complexity and cost associated with handling sensitive aryl halides and enabling efficient polymerization without the need for purification steps.

Problems solved by technology

While the Ober polymerization method works well, it is known to be sensitive to impurities in the aryl halide.
Also, the synthesis and handling of aryl mesylates, tosylates, and triflates adds cost and complexity to the polymerization process.

Method used

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  • Method of forming polyaryl polymers and polymers formed thereby
  • Method of forming polyaryl polymers and polymers formed thereby
  • Method of forming polyaryl polymers and polymers formed thereby

Examples

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examples

Synthesis of Polymer 1

[0049]This example illustrates homopolymerization of a single monomer. FIG. 1 is a chemical scheme for the synthesis of Polymer 1. Polymer 1, shown in FIG. 1, is synthesized by the following prophetic procedure. Inside a nitrogen-purged glovebox, to a 30 millilter vial is added 4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)methoxy)phenyl sulfurofluoridate (500 milligrams, 1 millimole, 1 equivalent) and 1,4-dioxane (3 milliliters). Potassium phosphate (637 milligrams, 3 millimoles, 3 equivalents) is dissolved in water (637 microliters) and added to the vial. The mixture is vigorously stirred until both phases are well-blended after which a catalyst solution of Pd(crotyl)(P(tBu)3) (0.4 milligram, 1 micromole, 0.001 equivalent) dissolved in 1,4-dioxane (100 microliters) is added. The reaction is vigorously stirred overnight, optionally with mild heating. The obtained polymer is optionally end-capped by adding phenyl boronic acid (18 milligrams, 0.15 m...

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Abstract

In a method of forming a polyaryl polymer, a fluorosulfonate-containing monomer is coupled with itself or a boron-containing comonomer in the presence of a catalyst and a base. The resulting polymers can be used as precursors to electrically conducting polymers, and as components of resist or underlayer compositions for photolithography, among other applications.

Description

FIELD[0001]The present invention relates to a method of synthesizing polyaryl polymers using fluorosulfonyl-substituted monomers.INTRODUCTION[0002]Polyaryl polymers in which aryl groups are directly bonded to each other are useful in a variety of applications, including as precursors to conductive and semiconductive polymers for use in Organic Light Emitting Diodes (OLED) and Polymeric Light Emitting Diodes (PLED), as acid-sensitive polymers and highly etch-resistant polymers for photolithography, and as pH-sensitive drug delivery encapsulants.[0003]Ober U.S. Pat. No. 8,962,779 B2 describes forming polyacetal and polyketal polymers by coupling an acetal- or ketal-containing monomer with itself or a comonomer in the presence of a catalyst and a base. The aryl-aryl coupling reaction involves the reaction of a first functional group directly bound to an aryl group and selected from chloro, bromo, iodo, mesylate, tosylate, or triflate with a second functional group that is a boron-conta...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08G61/12C08G61/10
CPCC08G61/10C08G61/128C08G61/02C08G61/12C08G2261/344C08G2261/11C08G2261/95C08G2261/312C08G2261/314C08G2261/3142C08G2261/41C07F5/04C07F5/05C08G75/02C08G75/0204C08G75/0213C08K5/55
Inventor OBER, MATTHIAS S.KRASOVSKIY, ARKADYHANLEY, PATRICK
Owner DOW GLOBAL TECH LLC