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Polyarylene material

A technology of aryl and aralkyl, applied in the field of polyarylene materials, can solve problems such as limited solubility and limited use of polymers

Active Publication Date: 2017-12-12
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such reaction solvents are poor choices as casting solvents in the electronics industry, from which polyarylene polymers must be precipitated and dissolved in different organic compounds with much lower boiling points suitable for casting films of these polymers. in solvent
Such polyarylene polymers, especially those prepared from certain diethynyl aromatic monomers, have limited solubility in organic solvents commonly used in the electronics industry, limiting the use of these polymers. usage of

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0048] Example 1. DPO-CPD (6.21 g, 7.93 mmol), 1,3-DEB (1.00 g, 7.93 mmol) and propiolic acid (0.056 g, 0.79 mmol) were added via a powder funnel to a multi-neck round bottom flask containing a stir bar, The reaction solvent ethoxybenzene (40 mL) was then added. The reaction was stirred gently at room temperature. The flask was then equipped with a reflux condenser and an internal thermocouple probe attached to a self-regulating thermostat attached to a heating mantle, and placed under a nitrogen atmosphere. Next, the dark maroon contents of the flask were warmed to an internal temperature of 130°C and maintained at this temperature for 22 hours before being cooled to 25°C by removing the heating element. The resulting orange-red solution was bottled and evaluated as a crude mixture. GPC of the resulting oligomer (Oligomer 1) indicated M as determined using polystyrene standards. w It is 13900 Da.

example 4

[0049] Example 4. The procedure of Example 3 was repeated multiple times using DPO-CPD as the first monomer, 1,3-DEB or 1,4-DEB as the second monomer, and the third monomer listed in Table 1 . The weight average molecular weights of the resulting oligomers are also reported in Table 1.

[0050] Table 1

[0051] Oligomer ID

[0052] 8

example 5

[0053] Example 5. Evaluate the solubility of oligomers in various organic solvents. Each oligomer was formulated by adding 5 g of a 30% solution of the reaction product along with 5 g of ethoxybenzene (EB) to a vial to make a 15% diluted polymer solution. 1 g of polymer solution was added to a 20 mL clear vial. The solvent MMP, PGMEA or PGME / PGMEA (30:70 v / v) mixture was added dropwise to the vial until a persistent precipitation was observed or until the solution became cloudy or until a maximum of 10 g of solvent was added. The amount of solvent added in grams to the weight ratio of 1 g of polymer solution is reported in Table 2.

[0054] Table 2

[0055]

[0056] The higher the ratio in Table 2, the more soluble the oligomer in the solvent. The above data show that oligomers formed using 1,4-DEB as the second monomer are more soluble in organic solvents than corresponding oligomers formed from 1,3-DEB. These data further show that oligomers of the present invention...

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Abstract

Polyarylene material. The present invention relates to certain polyarylene oligomers with enhanced solubility, which are suitable for forming layers of dielectric materials in electronic applications. The present invention provides an oligomer comprising as polymerized units a first monomer comprising two cyclopentadienone moieties, a second monomer having formula (1) and a second monomer having formula (2) the third monomer.

Description

technical field [0001] The present invention relates generally to the field of polyarylene materials and, more particularly, to polyarylene oligomers for electronic applications. Background technique [0002] Polymer dielectrics can be used as insulating layers in various electronic devices such as integrated circuits, multi-chip modules, laminated circuit boards, displays, and the like. The electronics manufacturing industry has different requirements for dielectric materials, such as dielectric constant, thermal expansion coefficient, modulus, etc., depending on the specific application. [0003] Various inorganic materials, such as silicon dioxide, silicon nitride, and aluminum oxide, have been used as dielectric materials in electronic devices. These inorganic materials can generally be deposited in thin layers, usually by vapor deposition techniques, and have advantageous properties, such as low water absorption. Polymer dielectric materials often have properties that...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C08L65/00C08J3/09
CPCC08G61/10C08G61/12C09D165/02C08L65/02H01L23/5329C08G2261/135C08G2261/1644C08G2261/312C08G2261/64C08G2261/76C08G2261/65H01L23/49894H01B3/307H01L2924/0002C08G2261/46C08G65/38C08L71/00C09D171/00H10K85/111H01L2924/00
Inventor C·D·吉尔莫L·卜P-W·庄D·王Y·姜P·丁Y·S·金K·M·奥康奈尔
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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