TW202206537A - Halogen free very low loss resin composition - Google Patents
Halogen free very low loss resin composition Download PDFInfo
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- TW202206537A TW202206537A TW110119406A TW110119406A TW202206537A TW 202206537 A TW202206537 A TW 202206537A TW 110119406 A TW110119406 A TW 110119406A TW 110119406 A TW110119406 A TW 110119406A TW 202206537 A TW202206537 A TW 202206537A
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- 239000011342 resin composition Substances 0.000 title claims description 38
- 229910052736 halogen Inorganic materials 0.000 title 1
- 150000002367 halogens Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 119
- 239000001257 hydrogen Substances 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 89
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 125000004104 aryloxy group Chemical group 0.000 claims description 49
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- 125000003545 alkoxy group Chemical group 0.000 claims description 48
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
- 150000001336 alkenes Chemical class 0.000 claims description 42
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 38
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 26
- 229920005989 resin Polymers 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 22
- 229920001955 polyphenylene ether Polymers 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 15
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 14
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000000470 constituent Substances 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 4
- -1 methoxy, carboxy Chemical group 0.000 claims description 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 claims description 2
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical class N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 4
- 239000013032 Hydrocarbon resin Substances 0.000 abstract description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 2
- 229920006270 hydrocarbon resin Polymers 0.000 abstract description 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 2
- 239000011574 phosphorus Substances 0.000 abstract description 2
- 150000003949 imides Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 abstract 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 description 17
- 239000003063 flame retardant Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 5
- 239000002966 varnish Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- APOXBWCRUPJDAC-UHFFFAOYSA-N bis(2,6-dimethylphenyl) hydrogen phosphate Chemical compound CC1=CC=CC(C)=C1OP(O)(=O)OC1=C(C)C=CC=C1C APOXBWCRUPJDAC-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/093—Polyol derivatives esterified at least twice by phosphoric acid groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/126—Polyphenylene oxides modified by chemical after-treatment
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- C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
- C08L85/02—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers containing phosphorus
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- 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
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
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- H—ELECTRICITY
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- 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
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Abstract
Description
本公開總體涉及無鹵素的極低損耗樹脂組合物。The present disclosure generally relates to halogen-free very low loss resin compositions.
電腦工程的不斷進步已經形成對高速、低損耗的印刷電路板(PCB)材料的增加需求。與前幾代的PCB材料相比，高速、低損耗的PCB材料展示出隨著傳輸頻率的增加而介電常數(Dk)變化較小，並且展示出相對低的介電損耗。Continuous advancements in computer engineering have created an increased demand for high-speed, low-loss printed circuit board (PCB) materials. Compared to previous generations of PCB materials, high-speed, low-loss PCB materials exhibit less variation in dielectric constant (Dk) with increasing transmission frequency and exhibit relatively low dielectric losses.
最近，開發無鹵素且展現出卓越的低耗散係數(Df)的高速、低損耗的PCB材料變得尤其重要。本領域已知的製劑通常基於徹底地固化的樹脂系統，例如包括含有豐富的C=C雙鍵的烴樹脂、丙烯酸酯封端的聚苯醚(PPE)和/或具有豐富的C=C雙鍵的交聯劑的系統。Recently, it has become especially important to develop high-speed, low-loss PCB materials that are halogen-free and exhibit an excellent low dissipation factor (Df). Formulations known in the art are generally based on thoroughly cured resin systems, such as including hydrocarbon resins rich in C=C double bonds, acrylate terminated polyphenylene ethers (PPE) and/or rich in C=C double bonds system of cross-linking agents.
不幸地，缺乏具有足夠低的Df以在這些高性能的PCB系統中有用的磷系阻燃劑。目前已知的反應型阻燃劑不提供所需的電性特徵。雖然某些添加劑型阻燃劑，比如間苯二酚雙[二(2,6-二甲基苯基)磷酸酯]，將提供所需的電性特性，但這些添加劑型阻燃劑將顯著降低組合物的耐熱性，包括玻璃化轉變溫度(Tg)和分解溫度(Td)。Unfortunately, there is a lack of phosphorus-based flame retardants with Df low enough to be useful in these high performance PCB systems. Currently known reactive flame retardants do not provide the desired electrical characteristics. While some additive flame retardants, such as resorcinol bis[bis(2,6-dimethylphenyl) phosphate], will provide the desired electrical properties, these additive flame retardants will significantly Decreases the thermal resistance of the composition, including the glass transition temperature (Tg) and decomposition temperature (Td).
因此，期望開發出無鹵素、阻燃的PCB材料，其提供良好的電特性和良好的耐熱特性，足以允許其用於高性能的PCB系統。Therefore, it would be desirable to develop halogen-free, flame retardant PCB materials that provide good electrical properties and good thermal properties sufficient to allow their use in high performance PCB systems.
例如，本文提供了樹脂組合物，其包括：有機磷烯烴，以組合物的按重量計約10%至按重量計約65%的量；不飽和樹脂，以組合物的按重量計約0%至按重量計約50%的量；二氧化矽，以組合物的按重量計約20%至按重量計約80%的量；以及自由基起始劑，以組合物的按重量計約0.5%至按重量計約7.5%的量。For example, provided herein is a resin composition comprising: an organophosphorous olefin in an amount of from about 10% by weight to about 65% by weight of the composition; an unsaturated resin in an amount of about 0% by weight of the composition Silica, in an amount from about 20% by weight to about 80% by weight of the composition; and a free radical initiator, in an amount of about 0.5% by weight of the composition % to about 7.5% by weight.
在一些實施方式中，本文提供的樹脂組合物包括式A的有機磷烯烴，
本文還提供了包括固化的樹脂組合物的印刷電路板，其中樹脂組合物如本文提供的。Also provided herein is a printed circuit board comprising the cured resin composition, wherein the resin composition is as provided herein.
其他目標和特徵將在下文中部分是顯而易見的並且部分被指出。Other objects and features will be partly apparent and partly pointed out hereinafter.
本文提供了無鹵素的、阻燃的可固化樹脂組合物，其提供良好的電特性和良好的耐熱特性，足以允許其用於高性能PCB系統。Provided herein are halogen-free, flame retardant curable resin compositions that provide good electrical properties and good thermal properties sufficient to allow their use in high performance PCB systems.
尤其，本文提供了作為反應型阻燃劑使用的新的有機磷烯烴。令人吃驚地，已經發現當併入PCB組合物時這些反應型化合物會提供良好的電特性和耐熱性。這些有機磷烯烴中C=C雙鍵的存在允許它們與不飽和樹脂(例如，C=C雙封端的聚苯醚、雙馬來酸亞胺等)反應，以形成網狀交聯。In particular, novel organophosphorous olefins for use as reactive flame retardants are provided herein. Surprisingly, these reactive compounds have been found to provide good electrical properties and thermal resistance when incorporated into PCB compositions. The presence of C=C double bonds in these organophosphorus olefins allows them to react with unsaturated resins (eg, C=C double-terminated polyphenylene ether, bismaleimide, etc.) to form network-like crosslinks.
例如，本文提供了包括有機磷烯烴、不飽和樹脂、二氧化矽以及自由基起始劑的樹脂組合物。下面將進一步詳細討論這些組成成分。 有機磷烯烴For example, provided herein are resin compositions comprising organophosphorous olefins, unsaturated resins, silica, and free radical initiators. These constituents are discussed in further detail below. Organophosphorous olefins
樹脂組合物可包括如本文提供的一種或多種有機磷烯烴。如以上討論的，已經發現本文提供的有機磷烯烴用作反應型阻燃劑，並且當併入PCB組合物時提供了令人吃驚地良好的介電性和耐熱性。The resin composition can include one or more organophosphorous olefins as provided herein. As discussed above, the organophosphorous olefins provided herein have been found to function as reactive flame retardants and provide surprisingly good dielectric and thermal resistance when incorporated into PCB compositions.
樹脂組合物可包括有機磷烯烴，例如，以組合物的按重量計約10%至按重量計約65%、按重量計約15%至按重量計約50%、按重量計約20%至按重量計約40%、按重量計約20%至按重量計約35%或按重量計約25%至按重量計約35%的量。The resin composition may include an organophosphorus olefin, for example, from about 10% by weight to about 65% by weight, from about 15% by weight to about 50% by weight, from about 20% by weight to about 20% by weight of the composition. An amount of about 40% by weight, about 20% by weight to about 35% by weight, or about 25% by weight to about 35% by weight.
在較佳實施方式中，樹脂組合物包括式A的化合物，
在較佳實施方式中，R4
和R5
各自獨立地選自由結構(1)、結構(2)和結構(3)所組成群組；
如本文使用的，專有名詞｢烷基｣指包括至多(up to)10個碳原子的直鏈或支鏈部分。合適的烷基的非限制性示例包括甲基、乙基、丙基、丁基、戊基和己基。烷基可以是直鏈烷基或支鏈烷基(例如異丙基)。在一些實施方式中，烷基任選地獨立地用選自由甲氧基、羧基所組成群組的一個或多個取代基取代。As used herein, the proper term "alkyl" refers to a straight or branched chain moiety that includes up to 10 carbon atoms. Non-limiting examples of suitable alkyl groups include methyl, ethyl, propyl, butyl, pentyl, and hexyl. Alkyl groups can be straight chain alkyl groups or branched chain alkyl groups (eg isopropyl). In some embodiments, the alkyl group is optionally substituted independently with one or more substituents selected from the group consisting of methoxy, carboxy.
如本文使用的，專有名詞｢芳基｣指包括6至14個碳原子的芳香族部分。在一些實施方式中，芳基任選地獨立地用選自由甲基、乙基、甲氧基和羧基所組成群組的一個或多個取代基取代。合適的芳基的非限制性示例包括苯基、萘基、苄基、甲苯基和甲苄基。As used herein, the proper term "aryl" refers to an aromatic moiety comprising 6 to 14 carbon atoms. In some embodiments, aryl groups are optionally substituted independently with one or more substituents selected from the group consisting of methyl, ethyl, methoxy, and carboxy. Non-limiting examples of suitable aryl groups include phenyl, naphthyl, benzyl, tolyl, and tolyl.
如本文使用的，專有名詞｢烷氧基｣指形成‒ORʹ的基團，其中Rʹ是如本文定義的烷基。例如，基團‒OCH3 本文可被稱為｢甲氧基｣。基團‒OCH2 CH3 本文可被稱為｢乙氧基｣。As used herein, the proper noun "alkoxy" refers to a group forming ‒ORʹ, where Rʹ is an alkyl group as defined herein. For example, the group -OCH3 may be referred to herein as "methoxy". The group ‒OCH 2 CH 3 may be referred to herein as "ethoxy".
如本文使用的，專有名詞｢芳氧基｣指形成‒ORʹ的基團，其中Rʹ是如本文定義的芳基。例如，基團‒O(C6 H6 )本文可被稱為｢苯氧基｣。As used herein, the proper noun "aryloxy" refers to a group forming ‒ORʹ, where Rʹ is an aryl group as defined herein. For example, the group -O ( C6H6 ) may be referred to herein as "phenoxy".
如本文使用的，專有名詞｢氫｣包括氫的兩種穩定同位素，即1 H (也稱為氕)和2 H (也稱為氘)。As used herein, the proper term "hydrogen" includes the two stable isotopes of hydrogen, namely 1 H (also known as protium) and 2 H (also known as deuterium).
如本文使用的，專有名詞｢羧基｣指形成‒C(O)OH的基團。As used herein, the proper term "carboxy" refers to a group that forms -C(O)OH.
在較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在一些實施方式中，每個Ar2 是相同的。例如，每個Ar2 可以是結構(4)的部分，其中每個X是相同的。在其他實施方式中，每個Ar2 是結構(5)的部分。In some embodiments, each Ar 2 is the same. For example, each Ar 2 can be part of structure (4), where each X is the same. In other embodiments, each Ar 2 is part of structure (5).
在較佳實施方式中，X選自由‒CH2 ‒和‒C(CH3 )2 ‒所組成群組。例如，X可以是‒C(CH3 )2 ‒。In a preferred embodiment, X is selected from the group consisting of -CH 2 - and -C(CH 3 ) 2 -. For example, X can be -C(CH 3 ) 2 -.
在較佳實施方式中，n是1至10的整數。例如，n可以是1、2、3、4、5、6、7、8、9或10。在一個示例性實施方式中，n是1。In a preferred embodiment, n is an integer from 1 to 10. For example, n can be 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. In an exemplary embodiment, n is 1.
例如，樹脂組合物可包括式I的化合物，
一般而言，每個R1 、R2 、R3 、Ar2 、X和n可以如上述關於式A選擇。In general, each of R 1 , R 2 , R 3 , Ar 2 , X and n can be selected as described above with respect to Formula A.
在式I的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In preferred embodiments of compounds of formula I, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式I的化合物的較佳實施方式中，Ar2 選自由結構(4)和結構(5)所組成群組，並且每個Ar2 是相同的。In a preferred embodiment of the compound of formula I, Ar 2 is selected from the group consisting of structure (4) and structure (5), and each Ar 2 is the same.
在式I的化合物的示例性實施方式中，Ar2 是結構(4)的部分，和X選自由‒CH2 ‒和‒C(CH3 )2 ‒所組成群組。例如，X可以是‒C(CH3 )2 ‒。In an exemplary embodiment of the compound of Formula I, Ar 2 is part of structure (4), and X is selected from the group consisting of -CH 2 - and -C(CH 3 ) 2 -. For example, X can be -C(CH 3 ) 2 -.
在式I的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula I, n is one.
例如，當Ar2
是結構(4)的部分時，化合物具有式Ia，
一般而言，R1 、R2 、R3 、X和n各自可如上述關於式A和/或式I選擇。In general, each of R 1 , R 2 , R 3 , X, and n can be selected as described above for Formula A and/or Formula I.
在式Ia的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In preferred embodiments of compounds of formula Ia, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式Ia的化合物的較佳實施方式中，X選自由‒CH2 ‒和‒C(CH3 )2 ‒所組成群組。例如，X可以是‒C(CH3 )2 ‒。In a preferred embodiment of the compound of formula Ia, X is selected from the group consisting of -CH 2 - and -C(CH 3 ) 2 -. For example, X can be -C(CH 3 ) 2 -.
在式Ia的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula Ia, n is 1.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，X是‒C(CH3
)2
‒，n是1，並且化合物是式Ia-i。
樹脂組合物可包括式II的化合物，
一般而言，R1 、R2 、R3 、Ar2 、X和n各自可如上述關於式A選擇。In general, each of R 1 , R 2 , R 3 , Ar 2 , X, and n can be selected as described above for formula A.
在式II的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula II, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式II的化合物的較佳實施方式中，Ar2 選自由結構(4)和結構(5)所組成群組，並且每個Ar2 是相同的。In a preferred embodiment of the compound of formula II, Ar 2 is selected from the group consisting of structure (4) and structure (5), and each Ar 2 is the same.
在式II的化合物的示例性實施方式中，Ar2 是結構(4)的部分，和X選自由‒CH2 ‒和‒C(CH3 )2 ‒所組成群組。例如，X可以是‒C(CH3 )2 ‒。In an exemplary embodiment of the compound of formula II, Ar 2 is part of structure (4), and X is selected from the group consisting of -CH 2 - and -C(CH 3 ) 2 -. For example, X can be -C(CH 3 ) 2 -.
在式II的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula II, n is one.
例如，當Ar2
是結構(4)的部分時，化合物具有式IIa，
一般而言，R1 、R2 、R3 、X和n各自可如上述關於式A和/或式II選擇。In general, each of R 1 , R 2 , R 3 , X and n can be selected as described above with respect to Formula A and/or Formula II.
在式IIa的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula IIa, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIa的化合物的較佳實施方式中，X選自由‒CH2 ‒和‒C(CH3 )2 ‒所組成群組。例如，X可以是‒C(CH3 )2 ‒。In a preferred embodiment of the compound of formula IIa, X is selected from the group consisting of -CH 2 - and -C(CH 3 ) 2 -. For example, X can be -C(CH 3 ) 2 -.
在式IIa的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IIa, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，X是‒C(CH3
)2
‒，n是1，並且化合物是式IIa-i。
樹脂組合物可包括式IIb的化合物，
一般而言，R1 、R2 、R3 和n各自可如上述關於式A和/或式II選擇。In general, each of R 1 , R 2 , R 3 and n can be selected as described above with respect to Formula A and/or Formula II.
在式IIb的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula lib, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIb的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula lib, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，n是1，並且化合物是式IIb-i。
樹脂組合物可包括式IIc的化合物，
一般而言，R1 、R2 、R3 和n各自可如上述關於式A和/或式II選擇。In general, each of R 1 , R 2 , R 3 and n can be selected as described above with respect to Formula A and/or Formula II.
在式IIc的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula IIc, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIc的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IIc, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，n是1，並且化合物是式IIc-i。
樹脂組合物可包括式IId的化合物，
一般而言，R1 、R2 、R3 和n各自可如上述官於式A和/或式II選擇。In general, each of R 1 , R 2 , R 3 and n can be selected as described above for Formula A and/or Formula II.
在式IId的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula IId, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IId的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IId, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，n是1，並且化合物是式IId-i。
樹脂組合物可包括式IIe的化合物，
一般而言，R1 、R2 、R3 和n各自可如上述關於式A和/或式II選擇。In general, each of R 1 , R 2 , R 3 and n can be selected as described above with respect to Formula A and/or Formula II.
在式IIe的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula IIe, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIe的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IIe, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，n是1，並且化合物是式IIe-i。
樹脂組合物可包括式IIf的化合物，
一般而言，R1 、R2 、R3 、R6 、R7 、X和n各自可如上述關於式A和/或式II選擇。In general, each of R 1 , R 2 , R 3 , R 6 , R 7 , X and n can be selected as described above with respect to Formula A and/or Formula II.
在式IIf的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula Ilf, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIf的化合物的較佳實施方式中，X選自由‒CH2 ‒和‒C(CH3 )2 ‒所組成群組。例如，X可以是‒C(CH3 )2 ‒。In a preferred embodiment of the compound of formula If, X is selected from the group consisting of -CH 2 - and -C(CH 3 ) 2 -. For example, X can be -C(CH 3 ) 2 -.
在式IIf的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula If, n is 1.
在示例性實施方式中，R1
和R2
是甲基，R3
、R6
和R7
各自是氫，X是‒C(CH3
)2
‒，n是1，並且化合物是式IIf-i。
本文進一步提供了式III的化合物，
一般而言，R1 、R2 、R3 、Ar2 、X和n各自可如上述關於式A選擇。In general, each of R 1 , R 2 , R 3 , Ar 2 , X, and n can be selected as described above for formula A.
在式III的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In preferred embodiments of compounds of formula III, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式III的化合物的較佳實施方式中，Ar2 選自由結構(4)和結構(5)所組成群組，並且每個Ar2 是相同的。In a preferred embodiment of the compound of formula III, Ar 2 is selected from the group consisting of structure (4) and structure (5), and each Ar 2 is the same.
在式III的化合物的示例性實施方式中，Ar2 是結構(4)的部分，和X選自由‒CH2 ‒和‒C(CH3 )2 ‒所組成群組。例如，X可以是‒C(CH3 )2 ‒。In an exemplary embodiment of the compound of Formula III, Ar 2 is part of structure (4), and X is selected from the group consisting of -CH 2 - and -C(CH 3 ) 2 -. For example, X can be -C(CH 3 ) 2 -.
在式III的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula III, n is one.
例如，當Ar2
是結構(4)的部分時，化合物具有式IIIa，
一般而言，R1 、R2 、R3 、X和n各自可如上述關於式A和/或式III選擇。In general, each of R 1 , R 2 , R 3 , X and n can be selected as described above with respect to Formula A and/or Formula III.
在式IIIa的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula Ilia, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIIa的化合物的較佳實施方式中，X選自由‒CH2 ‒和‒C(CH3 )2 ‒所組成群組。例如，X可以是‒C(CH3 )2 ‒。In a preferred embodiment of the compound of formula IIIa, X is selected from the group consisting of -CH 2 - and -C(CH 3 ) 2 -. For example, X can be -C(CH 3 ) 2 -.
在式IIIa的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IIIa, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，X是‒C(CH3
)2
‒，n是1，並且化合物是式IIIa-i。
樹脂組合物可包括式IIIb的化合物，
一般而言，R1 、R2 、R3 和n各自可如上述關於式A和/或式III選擇。In general, each of R 1 , R 2 , R 3 and n can be selected as described above with respect to Formula A and/or Formula III.
在式IIIb的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In preferred embodiments of compounds of formula IIIb, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIIb的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IIIb, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，n是1，並且化合物是式IIIb-i。
樹脂組合物可包括式IIIc的化合物，
一般而言，R1 、R2 、R3 和n各自可如上述關於式A和/或式III選擇。In general, each of R 1 , R 2 , R 3 and n can be selected as described above with respect to Formula A and/or Formula III.
在式IIIc的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula IIIc, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIIc的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IIIc, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，n是1，並且化合物是式IIIc-i。
樹脂組合物可包括式IIId的化合物，
一般而言，R1 、R2 、R3 和n各自可如上述關於式A和/或式III選擇In general, each of R 1 , R 2 , R 3 and n can be selected as described above for Formula A and/or Formula III
在式Id的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula Id, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIId的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IIId, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，n是1，並且化合物是式IIId-i。
樹脂組合物可包括式IIIe的化合物，
一般而言，R1 、R2 、R3 和n各自可如上述關於式A和/或式III選擇。In general, each of R 1 , R 2 , R 3 and n can be selected as described above with respect to Formula A and/or Formula III.
在式IIIe的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In a preferred embodiment of the compound of formula IIIe, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIIe的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IIIe, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
是氫，n是1，並且化合物是式IIIe-i。
樹脂組合物可包括式IIIf的化合物，
一般而言，R1 、R2 、R3 、R6 、R7 、X和n各自可如上述關於式A和/或式III選擇。In general, each of R 1 , R 2 , R 3 , R 6 , R 7 , X and n can be selected as described above with respect to Formula A and/or Formula III.
在式IIIf的化合物的較佳實施方式中，R1 、R2 和R3 各自獨立地選自由氫和C1 –C6 烷基所組成群組。例如，R1 、R2 、和R3 可各自獨立地選自由氫和甲基所組成群組。在較佳實施方式中，R1 和R2 各自獨立地選自由C1 –C6 烷基所組成群組並且R3 是氫。In preferred embodiments of compounds of formula IIIf, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl. For example, R 1 , R 2 , and R 3 can each be independently selected from the group consisting of hydrogen and methyl. In preferred embodiments, R 1 and R 2 are each independently selected from the group consisting of C 1 -C 6 alkyl and R 3 is hydrogen.
在式IIIf的化合物的較佳實施方式中，X選自由‒CH2 ‒和‒C(CH3 )2 ‒所組成群組。例如，X可以是‒C(CH3 )2 ‒。In a preferred embodiment of the compound of formula IIIf, X is selected from the group consisting of -CH 2 - and -C(CH 3 ) 2 -. For example, X can be -C(CH 3 ) 2 -.
在式IIIf的化合物的較佳實施方式中，n是1。In a preferred embodiment of the compound of formula IIIf, n is one.
在示例性實施方式中，R1
和R2
是甲基，R3
、R6
和R7
各自是氫，X是‒C(CH3
)2
‒，n是1，並且化合物是式IIIf-i。
樹脂組合物可進一步包括一種或多種不飽和樹脂。如以上討論的，已經發現有機磷烯烴中的C=C雙鍵的存在允許它們與不飽和樹脂反應以形成網狀交聯。The resin composition may further include one or more unsaturated resins. As discussed above, it has been found that the presence of C=C double bonds in organophosphorus olefins allows them to react with unsaturated resins to form network-like crosslinks.
如本文使用的，專有名詞｢不飽和樹脂｣指包括至少一個C=C雙鍵的樹脂。As used herein, the proper term "unsaturated resin" refers to a resin that includes at least one C=C double bond.
樹脂組合物可包括一種或多種不飽和樹脂，例如，以組合物的按重量計約0%至按重量計約50%、按重量計約10%至約40%、按重量計約10%至約30%、按重量計約15%至約30%或按重量計約15%至約25%的量。The resin composition may include one or more unsaturated resins, for example, from about 0% by weight to about 50% by weight, from about 10% by weight to about 40% by weight, from about 10% by weight to about 10% by weight of the composition An amount of about 30%, about 15% to about 30% by weight, or about 15% to about 25% by weight.
不飽和樹脂的非限制性示例包括丙烯酸酯封端的聚苯醚；雙馬來醯亞胺及其混合物。Non-limiting examples of unsaturated resins include acrylate terminated polyphenylene ethers; bismaleimides and mixtures thereof.
丙烯酸酯封端的聚苯醚Acrylate-terminated polyphenylene ether
樹脂組合物可包括式B的丙烯酸酯封端的聚苯醚
在一些實施方式中，Y是脂肪族主鏈，係包括1至20個碳原子，例如1至10個碳原子、1至8個碳原子、或1至6個碳原子。In some embodiments, Y is an aliphatic backbone comprising 1 to 20 carbon atoms, such as 1 to 10 carbon atoms, 1 to 8 carbon atoms, or 1 to 6 carbon atoms.
當樹脂組合物包括丙烯酸酯封端的聚苯醚時，丙烯酸酯封端的聚苯醚的濃度較佳為是組合物的按重量計約20%至按重量計約80%，例如，按重量計約40%至按重量計約70%、按重量計約45%至按重量計約65%或按重量計約50%至按重量計約60%。When the resin composition includes an acrylate-terminated polyphenylene ether, the concentration of the acrylate-terminated polyphenylene ether is preferably from about 20% by weight to about 80% by weight of the composition, for example, about 40% to about 70% by weight, about 45% by weight to about 65% by weight, or about 50% by weight to about 60% by weight.
雙馬來醯亞胺bismaleimide
樹脂組合物可包括式C的雙馬來醯亞胺
在一些實施方式中，R1 是脂肪族主鏈，係包括1至20個碳原子，例如1至10個碳原子、1至8個碳原子、或1至6個碳原子。In some embodiments, R 1 is an aliphatic backbone comprising 1 to 20 carbon atoms, such as 1 to 10 carbon atoms, 1 to 8 carbon atoms, or 1 to 6 carbon atoms.
當樹脂組合物包括雙馬來醯亞胺時，雙馬來醯亞胺的濃度較佳為是組合物的按重量計約1%至按重量計約50%，例如，按重量計約10%至按重量計約40%、按重量計約15%至按重量計約35%或按重量計約20%至按重量計約30%。When the resin composition includes bismaleimide, the concentration of bismaleimide is preferably from about 1% by weight to about 50% by weight of the composition, eg, about 10% by weight To about 40% by weight, from about 15% by weight to about 35% by weight, or from about 20% by weight to about 30% by weight.
不飽和樹脂的組合Combination of unsaturated resins
在一些實施方式中，樹脂組合物包括兩種或更多種不飽和樹脂的組合。例如，樹脂組合物可包括(1)丙烯酸酯封端的聚苯醚(包括但不限於式B的化合物)，和(2)雙馬來醯亞胺(包括但不限於式C的化合物)的組合。In some embodiments, the resin composition includes a combination of two or more unsaturated resins. For example, the resin composition may include a combination of (1) acrylate-terminated polyphenylene ether (including but not limited to compounds of formula B), and (2) bismaleimide (including but not limited to compounds of formula C) .
作為非限制性示例，當組合物包括丙烯酸酯封端的聚苯醚和雙馬來醯亞胺二者時，丙烯酸酯封端的聚苯醚的濃度可以在組合物的按重量計約1%至按重量計約30%、按重量計約2%至按重量計約25%、按重量計約5%至按重量計約20%或按重量計約5%至按重量計約15%的範圍。相似地，雙馬來醯亞胺的濃度可以在組合物的，例如，按重量計約1%至按重量計約30%、按重量計約2%至按重量計約25%、按重量計約5%至按重量計約20%或按重量計約5%至按重量計約15%的範圍。 填料組成成分As a non-limiting example, when the composition includes both the acrylate-terminated polyphenylene ether and the bismaleimide, the concentration of the acrylate-terminated polyphenylene ether may range from about 1% by weight to 1% by weight of the composition. A range of about 30% by weight, about 2% by weight to about 25% by weight, about 5% by weight to about 20% by weight, or about 5% by weight to about 15% by weight. Similarly, the concentration of bismaleimide can range from, for example, from about 1% by weight to about 30% by weight, from about 2% by weight to about 25% by weight, to about 25% by weight, of the composition. A range from about 5% to about 20% by weight or about 5% by weight to about 15% by weight. Filler composition
樹脂組合物可進一步包括填料組成成分。不受具體的理論的限制，填料組成成分的存在可改善組合物的尺寸穩定性、機械強度和/或導熱性。The resin composition may further include filler constituents. Without being bound by a particular theory, the presence of filler constituents may improve the dimensional stability, mechanical strength and/or thermal conductivity of the composition.
合適的填料組成成分的非限制性示例包括球形二氧化矽、熔融二氧化矽、氧化鋁、氫氧化鋁、氧化鎂、氫氧化鎂、氮化硼、雲母、滑石及其混合物。在較佳實施方式中，填料組成成分包括無機填料。例如，填料組成成分可包括二氧化矽。Non-limiting examples of suitable filler constituents include spherical silica, fused silica, alumina, aluminum hydroxide, magnesium oxide, magnesium hydroxide, boron nitride, mica, talc, and mixtures thereof. In a preferred embodiment, the filler constituents include inorganic fillers. For example, the filler composition may include silica.
樹脂組合物可包括填料組成成分，例如，以組合物的按重量計約20%至按重量計約80%、按重量計約30%至約70%或按重量計約40%至按重量計約60%的量。 自由基起始劑The resin composition may include filler constituents, for example, from about 20% by weight to about 80% by weight, from about 30% by weight to about 70% by weight, or from about 40% by weight to about 40% by weight of the composition. about 60% of the amount. free radical initiator
樹脂組合物可包括一種或多種自由基起始劑。不受具體的理論的限制，自由基起始劑可用來在升高的溫度釋放自由基，並且藉此觸發組合物中所有組成成分的交聯。The resin composition may include one or more free radical initiators. Without being bound by a particular theory, free radical initiators can be used to release free radicals at elevated temperatures and thereby trigger crosslinking of all constituents in the composition.
自由基起始劑的非限制性示例包括過氧化二異丙苯、二第三丁基過氧化物和過氧化苯甲醯。例如，自由基起始劑可包括過氧化物化合物。Non-limiting examples of free radical initiators include dicumyl peroxide, di-tert-butyl peroxide, and benzyl peroxide. For example, free radical initiators may include peroxide compounds.
樹脂組合物可包括一種或多種自由基起始劑，例如，以組合物的按重量計約0.5%至按重量計約7.5%、按重量計約0.5%至按重量計約5%、按重量計約0.5%至按重量計約2.5%、按重量計約1%至按重量計約2.5%或按重量計約1.5%至按重量計約2.5%的量。 印刷電路板The resin composition may include one or more free radical initiators, for example, from about 0.5% by weight to about 7.5% by weight, from about 0.5% by weight to about 5% by weight, by weight of the composition From about 0.5% to about 2.5% by weight, from about 1% by weight to about 2.5% by weight, or from about 1.5% by weight to about 2.5% by weight. A printed circuit board
還提供了包括如本文提供的樹脂組合物的印刷電路板。Also provided are printed circuit boards comprising the resin compositions as provided herein.
其他目標和特徵將在下文中是部分顯而易見的並且被部分指出。 實施例Other objects and features will be partly apparent and partly pointed out hereinafter. Example
提供以下非限制性實施例以進一步闡釋本公開。The following non-limiting examples are provided to further illustrate the present disclosure.
實驗材料Experimental Materials
本文提供的組合物可使用所屬技術領域中具有通常知識者已知的的典型技術配製。The compositions provided herein can be formulated using typical techniques known to those of ordinary skill in the art.
除非另外指示，以下描述的材料可在以下每個實施例中使用。Unless otherwise indicated, the materials described below can be used in each of the following examples.
SA9000是獲得自SABIC的丙烯酸酯封端的聚苯醚。SA9000 is an acrylate terminated polyphenylene ether available from SABIC.
TAIC是獲得自Tokyo Chemical Industry Co.的異氰尿酸三烯丙酯。TAIC is triallyl isocyanurate available from Tokyo Chemical Industry Co.
PX200是獲得自Daihachi Chemical Industry Co.的間苯二酚雙[二(2,6-二甲基苯基)磷酸酯]。PX200 is resorcinol bis[bis(2,6-dimethylphenyl)phosphate] available from Daihachi Chemical Industry Co.
BMI 5100是獲得自Daiwakasei Industry Co.的3,3'-二甲基-5,5'-二乙基-4,4'-二苯基甲烷雙馬來醯亞胺。BMI 5100 is 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide available from Daiwakasei Industry Co.
SC2300-SVJ是獲得自Admatechs Co., Ltd.的球形二氧化矽。SC2300-SVJ is spherical silica obtained from Admatechs Co., Ltd.
DCP是獲得自Sinopharm Chemical Reagent Co.的過氧化二異丙苯。DCP is dicumyl peroxide obtained from Sinopharm Chemical Reagent Co.
SPB100是獲得自Otsuka Chemical Co.的六苯氧基環三磷腈。SPB100 is hexaphenoxycyclotriphosphazene available from Otsuka Chemical Co.
如本文使用的，縮寫(tBuO)2 指獲得自Sinopharm Chemical Reagent Co.的二第三丁基過氧化物。As used herein, the abbreviation (tBuO) 2 refers to di-tert-butyl peroxide obtained from Sinopharm Chemical Reagent Co.
測試組合物的製備Preparation of test compositions
發明實施例1–6和比較實施例1–2如以下表1中描述的製備。
表1
層壓板應用Laminate Applications
測試如表1中描述的製備比較和發明實施例用於層壓板應用。Preparation comparisons and inventive examples as described in Table 1 were tested for laminate applications.
通過將實施例製劑與甲乙酮溶劑(按重量計清漆組合物的50%)組合來製備清漆。向托盤中倒入約200克的清漆。將一塊2116玻璃布(約30 cm × 30 cm)浸入清漆中，然後用手拉住通過一對有間隙的輥以控制厚度。製備的玻璃布的一個邊緣用夾子固定，然後掛在通風櫥裡，以允許清漆均勻地擴散，並促進溶劑蒸發。然後將玻璃布在小型處理機(具有良好的通風能力)中在升高的溫度下烘烤足以去除溶劑並且產生合理的預浸料凝膠時間的一段時間，所以溫度和時間可以根據具體情況進行調整。烘烤之後，獲得所期望的預浸料。Varnishes were prepared by combining the example formulations with methyl ethyl ketone solvent (50% by weight of the varnish composition). Pour about 200 grams of varnish into the tray. A piece of 2116 glass cloth (approximately 30 cm × 30 cm) was dipped into the varnish, then pulled by hand through a pair of gapped rollers to control thickness. One edge of the prepared glass cloth was clamped and then hung in a fume hood to allow the varnish to spread evenly and to facilitate solvent evaporation. The glass cloth is then baked in a small processor (with good ventilation) at elevated temperature for a period of time sufficient to remove the solvent and yield a reasonable prepreg gel time, so the temperature and time can be tailored to the situation Adjustment. After baking, the desired prepreg is obtained.
將六塊所得預浸料堆疊在一起，將頂部和底部表面的一半以35 μm的標準銅箔片覆蓋。然後將堆疊在200℃在壓機中層壓1.0小時。然後對所得的層壓板組合物測試以下表2所示的特性。The six resulting prepregs were stacked together, covering half of the top and bottom surfaces with 35 μm standard copper foil. The stack was then laminated in a press at 200°C for 1.0 hour. The resulting laminate compositions were then tested for the properties shown in Table 2 below.
表2表明，包括有機磷烯烴的發明實施例當用於層壓板應用時，提供了Tg、Td和Df之間理想的平衡。
表2
在比較實施例1和2中，將添加劑型阻燃劑SPB-100和PX-200分別與SA9000和TAIC配製。層壓板的Tg遠遠低於170°C，並非高Tg。這兩個實施例顯示了低損耗性能。PX-200可進一步降低層壓板Df至在1GHz的0.0020，比SPB-100更好。In Comparative Examples 1 and 2, additive flame retardants SPB-100 and PX-200 were formulated with SA9000 and TAIC, respectively. The Tg of the laminate is well below 170°C, not a high Tg. These two examples show low loss performance. PX-200 can further reduce laminate Df to 0.0020 at 1GHz, better than SPB-100.
在發明實施例1和2中，將式Ia和IIb的有機磷烯烴分別與SA9000和TAIC配製。由於有機磷烯烴可與其他組成成分反應以增加交聯密度，因此這兩種層壓板都對Tg具有顯著改善。兩種層壓板也實現有前景的低損耗性能，分別是在1GHz的0.0030 Df和在1GHz的0.0028 Df。阻燃性等級是V-1水準。In Inventive Examples 1 and 2, organophosphorous olefins of formula Ia and IIb were formulated with SA9000 and TAIC, respectively. Both laminates have a significant improvement in Tg because the organophosphorus olefins can react with other constituents to increase the crosslink density. Both laminates also achieved promising low loss performance, 0.0030 Df at 1 GHz and 0.0028 Df at 1 GHz, respectively. The flame retardancy level is the V-1 level.
在發明實施例3中，將式II的有機磷烯烴與SA9000配製。阻燃性等級進一步提高至V-0水準，儘管Df增加了一點為在1GHz的0.0040。In Inventive Example 3, an organophosphorus olefin of formula II was formulated with SA9000. The flame retardancy rating was further improved to the V-0 level, although the Df increased a little to 0.0040 at 1 GHz.
在發明實施例4中，將式IIa的有機磷烯烴與SA9000配製。層壓板可實現182°C的Tg和有前景的低損耗，在1GHz的0.0028 Df，而阻燃性被削弱到V-1水準。In Inventive Example 4, an organophosphorus olefin of formula IIa was formulated with SA9000. The laminate achieves a Tg of 182°C and promising low loss, 0.0028 Df at 1GHz, while the flame retardancy is weakened to V-1 levels.
在發明實施例5中，為了進一步增加抗熱性，BMI樹脂和球形二氧化矽被包括入製劑中。層壓板的Tg增加到205℃，具有良好的低損耗，在1GHz的0.0025 Df。In Inventive Example 5, to further increase heat resistance, BMI resin and spherical silica were included in the formulation. The Tg of the laminate increased to 205°C with good low loss, 0.0025 Df at 1GHz.
在發明實施例6中，不包括SA9000。將式IIa的有機磷烯烴與BMI樹脂配製。層壓板顯示出152°C的Tg，指示在製劑中沒有SA9000的情況下仍然形成了良好的交聯。Df沒有被削弱，並且在1GHz時保持在0.003以下。In Invention Example 6, SA9000 is not included. Organophosphorous olefins of formula IIa were formulated with BMI resins. The laminate showed a Tg of 152°C, indicating that good crosslinks were still formed without SA9000 in the formulation. Df is not nerfed and remains below 0.003 at 1GHz.
當引入本公開的要素或其較佳實施方式時，冠詞｢一個/一種｣(a)、｢一個/一種｣(an)、｢該｣和｢所述｣旨在代表有一個或多個要素。專有名詞｢包括/包含｣(comprising)、｢包括/包含｣(including)和｢具有｣意在包含，並且代表可能存在除所列元素之外的另外元素。When introducing elements of the present disclosure or the preferred embodiments thereof, the articles "a" (a), "an" (an), "the" and "said" are intended to mean that there are one or more of the elements . The proper terms "comprising", "including" and "having" are meant to be inclusive and mean that there may be additional elements other than the listed elements.
鑒於以上情況，將看出，本公開的幾個目標已經實現，並且取得了其他有利的結果。In view of the foregoing, it will be seen that several objectives of the present disclosure have been achieved, and other advantageous results have been obtained.
由於在不偏離本公開的範圍的情況下可以對以上產品和方法進行各種改變，其目的是以上描述中含有的所有事項應被解釋為說明性的，而不是限制性的。As various changes could be made in the above products and methods without departing from the scope of the present disclosure, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.
無without
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