US20170342199A1 - Oligomer, composition and composite material employing the same - Google Patents

Oligomer, composition and composite material employing the same Download PDF

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Publication number
US20170342199A1
US20170342199A1 US15/394,457 US201615394457A US2017342199A1 US 20170342199 A1 US20170342199 A1 US 20170342199A1 US 201615394457 A US201615394457 A US 201615394457A US 2017342199 A1 US2017342199 A1 US 2017342199A1
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Prior art keywords
hydrogen
oligomer
resin
copolymer
group
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US15/394,457
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Inventor
Wei-Ta YANG
Yen-Yi CHU
Ming-Tsung Hong
Li-Chun Liang
Yun-Ching Lee
Meng-Song Yin
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Industrial Technology Research Institute ITRI
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Industrial Technology Research Institute ITRI
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Priority to US15/394,457 priority Critical patent/US20170342199A1/en
Assigned to INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE reassignment INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: YIN, MENG-SONG, CHU, YEN-YI, HONG, MING-TSUNG, LEE, YUN-CHING, LIANG, LI-CHUN, YANG, WEI-TA
Publication of US20170342199A1 publication Critical patent/US20170342199A1/en
Priority to US15/851,309 priority patent/US10844164B2/en
Abandoned legal-status Critical Current

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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08J2365/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
    • C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • C08J2371/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
    • C08J2371/12—Polyphenylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2453/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • C08J2453/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers of vinyl aromatic monomers and conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2465/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/20—Applications use in electrical or conductive gadgets
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/0213—Electrical arrangements not otherwise provided for
    • H05K1/0237—High frequency adaptations
    • H05K1/024—Dielectric details, e.g. changing the dielectric material around a transmission line
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material
    • H05K1/032—Organic insulating material consisting of one material
    • H05K1/0326—Organic insulating material consisting of one material containing O

Definitions

  • the disclosure relates to an oligomer, a composition and a composite material employing the same.
  • the trend in electronic products has been toward smaller sizes, lighter weights, higher operating speeds, and higher-frequency transmission. Therefore, the distribution for printed circuit boards is toward high-density.
  • the ideal materials for use in printed circuit boards must have a low dielectric constant (dielectric constant, Dk) and a low dissipation factor (dissipation factor, Df).
  • Dk dielectric constant
  • DO dissipation factor
  • the disclosure provides an oligomer.
  • the oligomer has a structure represented by Formula (I)
  • R 1 and R 2 are independently hydrogen, C 1-20 alkyl group, C 2-20 alkenyl group, C 6-12 aryl group, C 6-12 alkylaryl group, C 5-12 cycloalkyl group, C 6-20 cycloalkylalkyl group, alkoxycarbonyl group, or alkylcarbonyloxy group, R 1 is not hydrogen when R 2 is hydrogen; a is 0 or 1; n ⁇ 0; m ⁇ 1; n:m is from about 0:100 to 99:1; the oligomer number average molecular weight less than or equal to 12,000; and the repeat unit
  • the disclosure also provides a composition including about 1-99 parts by weight of the aforementioned oligomer; and about 1-99 parts by weight of resin.
  • the disclosure also provides a composite material including a cured product or a semi-cured product prepared from the aforementioned composition; and a substrate, wherein the cured product or the semi-cured product is disposed on the substrate or disposed within the substrate.
  • Embodiments of the disclosure provide an oligomer, a composition, and a composite material employing the same.
  • the oligomer of the disclosure can be prepared by copolymerizing a first monomer (such as vinyl norbornene) and a second monomer (such as norbornene) via ring-opening polymerization, and ⁇ -olefin can be introduced during copolymerization in order to control the molecular weight of the obtained copolymer (i.e. the obtained copolymer can have a number average molecular weight less than or equal to 12,000).
  • the oligomer exhibits high processability.
  • the oligomer can enhance the mechanical strength of the substrate material when the oligomer is used as a reactant for preparing the substrate material.
  • Embodiments of the disclosure also provide a composition including the aforementioned oligomer and a composite material (such as a prepreg) including a cured product or a semi-cured product prepared from the composition.
  • the cured product of the composition of the disclosure exhibits a relatively low dielectric constant (Dk) (less than 3.0 (at 10 GHz)) and a relatively low dissipation factor (Df) (less than 0.0033 (at 10 GHz)), and can serve as a good material for the high-frequency substrate in order to improve the problem of insertion loss.
  • Dk dielectric constant
  • Df dissipation factor
  • the oligomer has a structure represented by Formula (I)
  • R 1 and R 2 are independently hydrogen, C 1-20 alkyl group, C 2-20 alkenyl group, C 6-12 aryl group, C 6-12 alkylaryl group, C 5-12 cycloalkyl group, C 6-20 cycloalkylalkyl group, alkoxycarbonyl group, or alkylcarbonyloxy group, R 1 is not hydrogen when R 2 is hydrogen; a is 0 or 1; n ⁇ 0 (such as n ⁇ 1); m ⁇ 1; n:m is from about 0:100 to 99:1; the oligomer number average molecular weight less than or equal to 12,000; and the repeat unit
  • the alkyl group of the disclosure can be linear or branched alkyl group.
  • R 1 and R 2 can be independently a linear or branched alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
  • the alkenyl group of the disclosure can be linear or branched alkenyl group.
  • R 1 and R 2 can be independently a linear or branched alkenyl group having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
  • R 1 and R 2 can be independently hydrogen, or
  • b can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, or 19; and R 1 is not hydrogen when R 2 is hydrogen.
  • the C 6-12 aryl group of the disclosure can be phenyl group, biphenyl group, or naphthyl group.
  • R 1 and R 2 are independently hydrogen, or
  • c can be 0, 1, 2, 3, 4, 5, or 6; and R 1 is not hydrogen when R 2 is hydrogen.
  • R 1 and R2 can be independently hydrogen, or
  • d can be 0, 1, 2, 3, 4, 5, or 6; and R 1 is not hydrogen when R 2 is hydrogen.
  • R 1 and R 2 can be independently hydrogen, or
  • e can be 0, 1, 2, 3, 4, 5, or 6; and R 1 is not hydrogen when R 2 is hydrogen.
  • R 1 and R 2 can be independently hydrogen, or
  • R 3 can be C 1-6 alkyl group, R 1 is not hydrogen when R 2 is hydrogen.
  • R 3 can be methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, or hexyl group.
  • R 1 and R 2 can be independently hydrogen, or
  • R 4 can be C 1-6 alkyl group; and R 1 is not hydrogen when R 2 is hydrogen.
  • R 4 can be methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, or hexyl group.
  • R 1 and R 2 can be independently hydrogen, or
  • h can be 1, 2, 3, 4, 5, or 6; and R 1 is not hydrogen when R 2 is hydrogen.
  • R 1 and R 2 can be independently hydrogen, or
  • i can be 0, 1, 2, 3, 4, 5, or 6; and R 1 is not hydrogen when R 2 is hydrogen.
  • R 1 and R 2 can be independently hydrogen, or
  • j can be 0, 1, 2, 3, 4, 5, or 6; and R 1 is not hydrogen when R 2 is hydrogen.
  • n:m can be from about 0:100 to 99:1, such as from about 1:9 to 9:1, from about 2:8 to 8:2, from about 3:7 to 7:3, or from about 3:7 to 6:4. Due to the adjustment of the ratio between the two repeat units of the oligomer, the properties of the cured product prepared by crosslinking the oligomer and the resin can be modified. For example, when increasing the amount of the repeat unit
  • the crosslinking density of the cured product can be increased.
  • the molecular weight of the coploymer can be controlled.
  • the number average molecular weight of the oligomer can be less than 12,000, such as from about 800 to 12,000, from about 800 to 9,000, from about 800 to 8,000, from about 800 to 7,000, from about 800 to 6,000, or from about 800 to 5,000.
  • the oligomer can have high solubility in organic solvent, thereby enhancing the processability of the oligomer.
  • the oligomer of the disclosure exhibits superior storability.
  • the method for preparing the aforementioned oligomer can include mixing and reacting a first monomer, a second monomer, and ⁇ -olefin to obtain the oligomer.
  • the method for preparing the aforementioned oligomer can include mixing and reacting a metal catalyst, a first monomer, a second monomer, and ⁇ -olefin to obtain the oligomer.
  • the method for preparing the aforementioned oligomer can include mixing and reacting a photoredox initiator, a photoredox mediator, a first monomer, a second monomer, and ⁇ -olefin to obtain the oligomer.
  • the photoredox initiator can be vinyl ether, 1-methoxy-4-phenyl butene, 2-cyclohexyl-1-methoxyethylene, or a combination thereof.
  • the photoredox mediator can be pyrylium salt, acridinium salt, or a combination thereof.
  • the method for preparing the aforementioned oligomer can include mixing and reacting a first monomer, a second monomer, and ⁇ -olefin under electrochemical condition to obtain the oligomer.
  • the metal catalyst can be Grubbs catalyst, such as first-generation Grubbs catalyst, second-generation Grubbs catalyst, Hoveyda-Grubbs catalyst, derivatives thereof, or a combination including at least one of the above catalysts.
  • Grubbs catalyst such as first-generation Grubbs catalyst, second-generation Grubbs catalyst, Hoveyda-Grubbs catalyst, derivatives thereof, or a combination including at least one of the above catalysts.
  • the first monomer can be
  • the first monomer is vinyl norbornene.
  • the second monomer can be norbornene
  • the ⁇ -olefin can be
  • R 5 can be C 1-20 alkyl group, C 2-20 alkenyl group, C 6-12 aryl group, C 6-12 alkylaryl group, C 5-12 cycloalkyl group, C 6-20 cycloalkylalkyl group, alkoxycarbonyl group, or alkylcarbonyloxy group.
  • ⁇ -olefin can be
  • b, c, d, e, f, g, h, i, j, R 3 , and R 4 have the same definition as above.
  • the sequence in which components are added is not limited.
  • a metal catalyst can be dissolved in a solvent first, obtaining a metal-catalyst-containing solution.
  • a solution including the first monomer and ⁇ -olefin is mixed with the metal-catalyst-containing solution.
  • the second monomer is added into the above mixture.
  • the molar ratio of the first monomer to the second monomer can be from about 100:0 (i.e.
  • the second monomer added there is no the second monomer added) to 1:99, such as from about 9:1 to 1:9, from about 8:2 to 2:8, from about 3:7 to 7:3, or from about 3:7 to 6:4.
  • the molar percentage of ⁇ -olefin can be from about 1 mol % to 85 mol %, such as about from 5 mol % to 75 mol %, or about from 10 mol % to 75 mol %, based on the total moles of the first monomer and the second monomer.
  • the amount of the ⁇ -olefin is inversely proportional to the molecular weight of the oligomer, so that the molecular weight of the oligomer can be controlled by means of the amount of ⁇ -olefin.
  • the molar percentage of ⁇ -olefin is too low, the oligomer would have relatively high molecular weight and exhibit poor processability and storability.
  • the molar percentage of ⁇ -olefin is too high, the oligomer would have a relatively low molecular weight and the process for preparing the substrate is not easy to control.
  • the disclosure also provides a composition including the aforementioned oligomer, and one or at least one resin.
  • the composition can include about 1-99 parts by weight of the oligomer, about 10-90 parts by weight of the oligomer, or about 20-80 parts by weight of the oligomer.
  • the composition can include about 1-99 parts by weight of the resin, about 10-90 parts by weight of the resin, or about 20-80 parts by weight of the resin.
  • the resin can be polyolefin resin (such as polybutadiene resin), polyalkenamer resin, cyclic olefin polymer resin, cycloolefin copolymer resin, epoxy resin, cyanate resin, phenol resin, novolac resin, polystyrene resin, styrene-butadiene copolymer resin (such as polystyrene-butadiene-styrene resin), polyamide resin, polyimide resin, maleimide resin, bismaleimide resin, polyphenylene ether resin, or a combination thereof.
  • the weight percentage of the oligomer can be from about 1 wt % to 99 wt %, from about 10 wt % to 90 wt %, or from about 20 wt % to 80 wt %
  • the weight percentage of the resin can be from about 1 wt % to 99 wt %, from about 10 wt % to 90 wt %, or from about 20 wt % to 80 wt %, based on the total weight of the oligomer and resin.
  • the disclosure also provides a composite material.
  • the composite material can include a cured product or a semi-cured product of the composition, and a substrate.
  • the cured product or semi-cured product is disposed on the substrate or within the substrate.
  • the substrate can be a glass fiber, or a copper foil.
  • the composite material can include a prepreg, and the method for preparing the prepreg includes immersing a glass fiber (serving as the substrate) into the aforementioned composition. Next, the composition is subjected to a semi-curing process, obtaining the prepreg.
  • the composite material can further include a copper foil, and the composite material can be a copper foil substrate, a printed circuit board, or an integrated circuit.
  • inventive concept of the disclosure may be embodied in various forms without being limited to the exemplary embodiments set forth herein.
  • Copolymer (I) was about 1:1.
  • Copolymer (II) was about 1:1
  • Copolymer (IV) was about 0.5:1.
  • Copolymer (V) was about 1:1
  • Copolymer (VI) was about 1:1.
  • Copolymer (VII) was about 1:1.
  • Copolymer (IX) was about 1:1.
  • Copolymer (X) was about 1:1.
  • the number average molecular weight (Mn), the polydispersity index (PDI) of the obtained copolymer can be controlled by means of the addition of 1-hexene ( ⁇ -olefin). Therefore, the obtained copolymer has a molecular weight less than or equal to 12,000, thereby increasing the solubility of the copolymer and promoting the subsequent process.
  • ⁇ -olefin (1-octadecene) had a molar percentage of 50 mol %, based on the total moles of vinyl norbornene and norbornene.
  • 25 ml of ethyl vinyl ether was added into the reaction bottle.
  • the catalyst of the result was removed and then was purified by a reprecipitation with methanol. After concentration, Copolymer (XII) was obtained.
  • Example 11 was performed in the same manner as Example 10 except that the amount of 1-octadecene was reduced from 0.247 mol to 0.049 mol, obtaining Copolymer (XIII).
  • the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XIII) were determined, and the results are shown in Table 2.
  • Example 12 was performed in the same manner as Example 10 except that the 1-octadecene was replaced with styrene, obtaining Copolymer (XIV).
  • Mn number average molecular weight
  • PDI polydispersity index
  • TGA thermogravimetric analysis
  • Example 15 was performed in the same manner as Example 10 except that the 1-octadecene was replaced with allyl acetate, obtaining Copolymer (XVII).
  • Mn number average molecular weight
  • PDI polydispersity index
  • TGA thermogravimetric analysis
  • Example 16 was performed in the same manner as Example 10 except that the 1-octadecene was replaced with 1,5-hexadiene, obtaining Copolymer (XVIII).
  • the number average molecular weight (Mn), the polydispersity index (PDI), the solubility (in toluene), and the temperature corresponding to a thermogravimetric analysis (TGA) weight loss of 5% of Copolymer (XVIII) were determined, and the results are shown in Table 2.
  • the number average molecular weight (Mn), the polydispersity index (PDI) of the obtained copolymer can be controlled by means of the addition of ⁇ -olefin.
  • Mn number average molecular weight
  • PDI polydispersity index
  • the suitable amount (mol %) of ⁇ -olefin is larger than about 70 mol %, such as larger than 80 mol %.
  • copolymers prepared from Examples 1-6 and 9-16 and Comparative Examples 1-2 were kept for one day (or two days), and then the solubility (in toluene) and viscosity of the copolymer were measured. The results are shown in Table 3.
  • Example Example Example Example 1 2 3 5 6 9 10 solubility kept >70 >70 >70 >60 >60 20 >70 in toluene for one (wt %) day kept >70 >70 >60 >60 >15 >70 for 2 days viscosity(cP) 100 534 11,260 376,200 2,754 solid 18
  • Example 1 Example 2 solubility kept >70 >70 >70 >70 ⁇ 10 ⁇ 10 in toluene for one (wt %) day kept >70 >70 >70 >70 ⁇ 1 insoluble for 2 days viscosity(cP) 2,869 11,260 52,140 78 solid solid solid solid
  • the copolymers prepared from Examples exhibit superior solubility after two days, since the molecular weight and polydispersity index of the copolymer can be controlled by means of the addition of ⁇ -olefin (the obtained copolymers have a molecular weight less than or equal to 12,000). Accordingly, the oligomer of the disclosure exhibits superior storability.
  • Copolymer (I) (40 parts by weight) of Example 1, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (60 parts by weight), and a suitable quantity of initiator were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a composition was obtained. Next, the aforementioned composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the composition was heated at 100° C. for a period of time. Next, the above copper foil was then heated gradually and then the composition was subjected to a crosslinking reaction under a temperature less than 250° C. (in order to achieve the best crosslinking density), obtaining Film (I). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (I) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 18 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (III) of Example 3, obtaining Film (II). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (II) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 19 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (IV) of Example 4, obtaining Film (III). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (III) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 20 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (V) of Example 5, obtaining Film (IV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (IV) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 21 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (VI) of Example 6, obtaining Film (V). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (V) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 22 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (VIII) of Example 8, obtaining Film (VI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (VI) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 23 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XII) of Example 10, obtaining Film (VII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (VII) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 24 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XIII) of Example 11, obtaining Film (VIII). Next, the dielectric constant (Dk) and the dissipation factor (DO of Film (VIII) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 25 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XIV) of Example 12, obtaining Film (XI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XI) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 26 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XV) of Example 13, obtaining Film (X). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (X) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 27 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVI) of Example 14, obtaining Film (XI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XI) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 28 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVII) of Example 15, obtaining Film (XII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XII) were measured at 10 GHz, and the results are shown in Table 4.
  • Example 29 was performed in the same manner as Example 17 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVIII) of Example 16, obtaining Film (XIII). Next, the dielectric constant (Dk) and the dissipation factor (DO of Film (XIII) were measured at 10 GHz, and the results are shown in Table 4.
  • 1,3,5-tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (40 parts by weight), polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (60 parts by weight), and a suitable quantity of initiator were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a composition was obtained. Next, the aforementioned composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the composition was heated at 100° C. for a period of time.
  • TAIL 1,3,5-tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
  • Copolymer (I) (31 parts by weight) of Example 1, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (46 parts by weight), polystyrene-butadiene-styrene (SBS, manufactured by Cray Valley with a trade No. of Ricon100) (with a molecular weight of about 4,500) (23 parts by weight) and a suitable quantity of initiator were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a composition was obtained. Next, the aforementioned composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.).
  • the copper foil coated with the composition was heated at 100° C. for a period of time.
  • the above copper foil was then heated gradually and then the composition was subjected to a crosslinking reaction under a temperature less than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XV).
  • the dielectric constant (Dk) and the dissipation factor (Df) of Film (XV) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 31 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (III) of Example 3, obtaining Film (XVI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XVI) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 32 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (IV) of Example 4, obtaining Film (XVII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XVII) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 33 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (V) of Example 5, obtaining Film (XVIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XVIII) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 34 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (VI) of Example 6, obtaining Film (XIX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XIX) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 35 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (VIII) of Example 8, obtaining Film (XX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XX) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 36 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (XII) of Example 10, obtaining Film (XXI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXI) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 37 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (XIII) of Example 11, obtaining Film (XXII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXII) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 38 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (XIV) of Example 12, obtaining Film (XXIII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXIII) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 39 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (XV) of Example 13, obtaining Film (XXIV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXIV) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 40 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVI) of Example 14, obtaining Film (XXV). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXV) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 41 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVII) of Example 15, obtaining Film (XXVI). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXVI) were measured at 10 GHz, and the results are shown in Table 5.
  • Example 42 was performed in the same manner as Example 30 except that Copolymer (I) of Example 1 was replaced with Copolymer (XVIII) of Example 16, obtaining Film (XXVII). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXVII) were measured at 10 GHz, and the results are shown in Table 5.
  • 1,3,5-tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (31 parts by weight), polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (46 parts by weight), polystyrene-butadiene-styrene (SBS, manufactured by Cray Valley with a trade No. of Ricon100) (with a molecular weight of about 4,500) (23 parts by weight) and a suitable quantity of initiator were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a composition was obtained.
  • PPE polyphenylene ether
  • SBS polystyrene-butadiene-styrene
  • Ricon100 polystyrene-butadiene-styrene
  • a suitable quantity of initiator were added into a reaction bottle, and then
  • the aforementioned composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.).
  • the copper foil coated with the composition was heated at 100° C. for a period of time.
  • the above copper foil was then heated gradually and then the composition was subjected to a crosslinking reaction under a temperature less than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XXVIII).
  • the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXVIII) were measured at 10 GHz, and the results are shown in Table 5.
  • Copolymer (I) 70 parts by weight) of Example 1, polystyrene-butadiene-styrene (SBS, manufactured by Cray Valley with a trade No. of Ricon100) (with a molecular weight of about 4,500) (30 parts by weight) and a suitable quantity of initiator were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a composition was obtained. Next, the aforementioned composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.). Next, the copper foil coated with the composition was heated at 90° C. for a period of time.
  • SBS polystyrene-butadiene-styrene
  • Example 44 was performed in the same manner as Example 39 except that Copolymer (I) of Example 1 was replaced with Copolymer (VIII) of Example 8, obtaining Film (XXX). Next, the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXX) were measured at 10 GHz, and the results are shown in Table 6.
  • Copolymer (III) 31 parts by weight) of Example 3, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (46 parts by weight), polybutadiene (PB, manufactured by Nippon Soda with a trade No. of B2000) (with a molecular weight of about 2,100) (23 parts by weight) and a suitable quantity of initiator were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a composition was obtained. Next, the aforementioned composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.).
  • the copper foil coated with the composition was heated at 100° C. for a period of time.
  • the above copper foil was then heated gradually and then the composition was subjected to a crosslinking reaction under a temperature less than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XXXI).
  • the dielectric constant (Dk) and the dissipation factor (Df) of Film (XXXI) were measured at 10 GHz, and the results are shown in Table 6.
  • Copolymer (V) 38 parts by weight) of Example 5, polyphenylene ether (PPE, manufactured and sold by SABIC with a trade No. of SA9000 (with a molecular weight of about 2,300) (57 parts by weight), bismaleimide (manufactured and sold by Daiwa Kasei Kogyo Co. with a trade No. of BMI-5,100) (with a molecular weight of about 2,100) (5 parts by weight) and a suitable quantity of initiator were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a composition was obtained. Next, the aforementioned composition was coated on a copper foil (manufactured and sold by Furukawa Circuit Foil Co., Ltd.).
  • the copper foil coated with the composition was heated at 100° C. for a period of time.
  • the above copper foil was then heated gradually and then the composition was subjected to a crosslinking reaction under a temperature less than 250° C. (in order to achieve the best crosslinking density), obtaining Film (XXXII).
  • the dielectric constant (Dk) and the dissipation factor (DO of Film (XXXII) were measured at 10 GHz, and the results are shown in Table 6.
  • Copolymer (III) (17 parts by weight) of Example 3, polyphenylene ether (PPE, manufactured and sold by Mitsubishi Gas Chemical with a trade No. of OPE-2st (with a molecular weight of about 2,200) (70 parts by weight), polystyrene-butadiene-styrene (manufactured and sold by Cray Valley. with a trade No. of Ricon100) (with a molecular weight of about 4,500) (13 parts by weight) and a suitable quantity of initiator were added into a reaction bottle, and then dissolved in toluene. After mixing completely, a composition was obtained. After stirring completely, a composition was obtained. Next, glass fiber (sold by Asahi Fiber Glass with a trade No.
  • the composition includes an oligomer having a structure represented by Formula (I)
  • the cured product exhibits a relatively low dielectric constant (less than or equal to 3.0 (at 10 GHz) and a relatively low dissipation factor (less than or equal to 0.0033 (at 10 GHz)), thereby serving as a good material for a high-frequency substrate.
  • the composition of the disclosure can be crosslinked at a temperature less than 250° C., and the obtained oligomer exhibits superior crosslinking density.
  • the oligomer can achieve optimal crosslinking density which is checked by means of the crosslinking exotherm determined by differential scanning calorimetry.

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US10844164B2 (en) 2016-05-24 2020-11-24 Industrial Technology Research Institute Oligomer, composition and composite material employing the same
CN113088060A (zh) * 2019-12-23 2021-07-09 台光电子材料(昆山)有限公司 一种树脂组合物及由其制备的制品
US11059938B2 (en) 2018-10-05 2021-07-13 Industrial Technology Research Institute Film composition and a film prepared thereby

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CN113444355B (zh) * 2020-03-24 2023-04-14 中山台光电子材料有限公司 树脂组合物及其制品
CN112608631B (zh) * 2020-12-22 2021-11-26 石狮市星盛五金制品有限公司 一种手机按键及其加工工艺
US11932714B2 (en) 2021-07-22 2024-03-19 Industrial Technology Research Institute Copolymer, film composition and composite material employing the same
TWI818811B (zh) * 2022-11-21 2023-10-11 南亞塑膠工業股份有限公司 樹脂組成物

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US11059938B2 (en) 2018-10-05 2021-07-13 Industrial Technology Research Institute Film composition and a film prepared thereby
CN113088060A (zh) * 2019-12-23 2021-07-09 台光电子材料(昆山)有限公司 一种树脂组合物及由其制备的制品

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