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Polymers derived from norbornadiene and maleic anhydride and use thereof

A technology of polymers and compositions, applied in the direction of photolithography, instruments, and optomechanical equipment on the pattern surface, can solve the problems of increasing wiring density and high signal speed, not suitable for many applications, low permittivity, etc.

Active Publication Date: 2018-08-31
SUMITOMO BAKELITE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While some polyimides and polybenzoxazoles have low dielectric constants, they still may not have sufficiently low permittivity to be effective for use in heightened wiring with increased wiring density and high signal speeds Integrated and / or Miniaturized Devices
In addition, both polyimide and polybenzoxazole require curing temperatures in excess of 300°C, thus rendering them unsuitable for many applications

Method used

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  • Polymers derived from norbornadiene and maleic anhydride and use thereof
  • Polymers derived from norbornadiene and maleic anhydride and use thereof
  • Polymers derived from norbornadiene and maleic anhydride and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment ( 1

[0412] Unless otherwise indicated, the following definitions are used in the following examples.

[0413] NBD: norbornadiene; MA: maleic anhydride; MI: maleimide; N-CyHexMI: N-cyclohexylmaleimide; N-PhMI: N-phenylmaleimide; NB : norbornene; NBTON: 5-((2-(2-methoxyethoxy)ethoxy)methyl)bicyclo[2.2.1]hept-2-ene; TrisP3M6C-2-201: general formula (VIo) PAC (where Q is the general formula (Va)); TMPTGE: trimethylolpropane triglycidyl ether; VG3101L: 2,2'-((((1-(4-(2-(4- (Oxirane-2-ylmethoxy)phenyl)propan-2-yl)phenyl)ethane-1,1-diyl)bis(4,1-phenylene))bis(oxyl )) bis(methylene))bis(ethylene oxide); GE-36: triglycidyl ether of poly(oxypropylene)epoxide ether of glycerol; Heloxy 505: polyglycidyl ether of castor oil; GT-401: epoxy crosslinking agent; JER1032H60: epoxy crosslinking agent; THETATO: 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6 - Triketone; TOTATO: 1,3,5-tris(oxirane-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione; Powderlink1174: 1,3 ,4,6-Tetra(methoxymethyl)tetrahydro...

Embodiment 1

[0417] (Terpolymer of NBD / MA / N-PhMI)

[0418] Dissolve maleic anhydride (MA, 4.9g, 50mmol), N-phenylmaleimide (N-PhMI, 7.45g, 43mmol) and 2,5-norbornadiene (NBD, 9.2g, 100mmol) in toluene (67 g) and charged to an appropriately sized reaction vessel with nitrogen inlet / outlet, water cooled condenser and ports for thermocouple. The solution was sparged with nitrogen for 10 minutes to deoxygenate, then heated to about 65°C. Then lauroyl peroxide (0.8 g, 2 mmol) was added, and after the mixture was stirred at 65° C. to 70° C. for 5 hours, the solution was cooled to room temperature. The solid polymer was separated from the solution and washed with enough heptane, filtered, and dried in a vacuum oven at 80°C for 20 hours. Approximately 18 g (84% yield) of NBD / N-PhMI / MA polymer (GPC(DMAc) Mw = 52,350, Mn = 15,400, PDI = 3.4) was isolated. According to the polymer in deuterated DMSO 13 C-NMR characterization, in the presence of the cyclopropane structure, peaks appear at 10-20ppm...

Embodiment 2

[0420] (terpolymer of NBD / MA / MI)

[0421] Maleic anhydride (MA, 10.3 g, 105 mmol), maleimide (MI, 4.4 g, 45 mmol) and 2,5-norbornadiene (NBD, 13.8 g, 150 mmol) were dissolved in toluene (69.2 g) and charged into an appropriately sized reaction vessel with nitrogen inlet / outlet, water-cooled condenser, and ports for thermocouples. The solution was sparged with nitrogen for 10 minutes to deoxygenate, then heated to about 65°C. Then lauroyl peroxide (1.2 g, 3 mmol) was added, and after stirring the mixture at 65˜70° C. for 5 hours, the solution was cooled to room temperature. The solid polymer was separated from the solution and washed with enough heptane, filtered, and dried in a vacuum oven at 80°C for 20 hours. Approximately 23.6 g (83% yield) of NBD / MI / MA polymer (GPC(DMAc) Mw = 43,200, Mn = 19,000, PDI = 2.27) was isolated. According to the polymer in deuterated DMSO 13 According to C-NMR, in the presence of a cyclopropane structure, a peak appears at 10 to 20 ppm, in th...

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Abstract

Embodiments encompassing a series of compositions containing polymers of norbornadiene and maleic anhydride monomers which are useful in forming a variety of photopatternable structures are disclosedand claimed. The compositions are useful as permanent dielectric materials. More specifically, embodiments encompassing compositions containing a series of ter- and tetrapolymers of a variety of norbornadiene, maleic anhydride, maleimide and norbornene-type cycloolefinic monomers in which maleic anhydride is fully or partially hydrolyzed (i.e., ring opened and fully or partially esterified), and aphotoactive compound are disclosed, which are useful in forming permanent dielectric materials having utility in a variety of electronic material applications, among various other uses.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application Serial No. 62 / 273,553, filed December 31, 2015, which is hereby incorporated by reference in its entirety. technical field [0003] The present invention relates to a composition useful as a permanent dielectric material comprising a series of polymers derived from various polycycloolefin monomers, maleic anhydride and maleimide monomers. More specifically, the present invention relates to a combination of a series of terpolymers and tetrapolymers containing various norbornadiene, norbornene-type cycloolefin monomers, maleimide monomers and maleic anhydride Compositions wherein total or partial hydrolysis (i.e., ring opening and total or partial esterification) of maleic anhydride, the compositions of the present invention can be used to form permanent dielectrics useful in a variety of other applications, including various electronic material applications M...

Claims

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Application Information

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IPC IPC(8): C08L47/00C08F32/06C08L45/00
CPCC08F32/06C08L47/00C08F2/50C08F22/06C08F232/06C08F232/08C08L45/00G03F7/022G03F7/168G03F7/2002G03F7/322C08F32/08G03F7/039G03F7/162G03F7/40
Inventor L·F·罗德P·坎达纳朗齐
Owner SUMITOMO BAKELITE CO LTD