CN106556970B - 混成碳黑与涂布组合物 - Google Patents
混成碳黑与涂布组合物 Download PDFInfo
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- CN106556970B CN106556970B CN201610050874.7A CN201610050874A CN106556970B CN 106556970 B CN106556970 B CN 106556970B CN 201610050874 A CN201610050874 A CN 201610050874A CN 106556970 B CN106556970 B CN 106556970B
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
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- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
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- HXDBMSZZSWTGKB-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylidenebutanoic acid Chemical compound CCOC(=O)C=C.CCC(=C)C(O)=O HXDBMSZZSWTGKB-UHFFFAOYSA-N 0.000 description 1
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- IQSHMXAZFHORGY-UHFFFAOYSA-N methyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound COC(=O)C=C.CC(=C)C(O)=O IQSHMXAZFHORGY-UHFFFAOYSA-N 0.000 description 1
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- 230000000877 morphologic effect Effects 0.000 description 1
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- WMRNGPYHLQSTDL-UHFFFAOYSA-N n-cyclohexyl-2-[[1-(cyclohexylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound C1CCCCC1NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC1CCCCC1 WMRNGPYHLQSTDL-UHFFFAOYSA-N 0.000 description 1
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- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- VIHFRCKJTLYJMW-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1.C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 VIHFRCKJTLYJMW-UHFFFAOYSA-N 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
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- 238000000235 small-angle X-ray scattering Methods 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
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- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- OIQNWJHRBIPDFR-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate 2-tert-butylbenzenecarboperoxoic acid Chemical compound C(C)(C)(C)C1=C(C(=O)OO)C=CC=C1.C(C1=CC=CC=C1)(=O)OOC(C)(C)C OIQNWJHRBIPDFR-UHFFFAOYSA-N 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- 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
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/44—Carbon
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- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/44—Carbon
- C09C1/48—Carbon black
- C09C1/56—Treatment of carbon black ; Purification
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- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/006—Combinations of treatments provided for in groups C09C3/04 - C09C3/12
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- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/10—Treatment with macromolecular organic compounds
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- C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- Wood Science & Technology (AREA)
- Architecture (AREA)
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Abstract
本发明提供混成碳黑,包括:碳黑核心;以及高分子膜,包覆碳黑核心的所有表面,其中高分子膜包含网状交联的多个高分子主链,以及键结至高分子主链的多个分散侧链,其中该分散侧链来自于丙烯酸酯系单体,且丙烯酸酯系单体的结构如下:当n=4‑7时,R1为H或CH3;以及当n=8‑14时,R1为CH3。
Description
【技术领域】
本发明涉及混成碳黑(hybrid carbon black),更特别涉及包含混成碳黑的涂布组合物。
【背景技术】
目前触控面板仍需要在表面盖板上形成一层遮光的边框层,其中之一即是黑色矩阵光致抗蚀剂层。黑色矩阵光致抗蚀剂层主要是将碳黑分散于感光光致抗蚀剂中,然后在表面玻璃盖板上经由涂布、软烤、曝光、显影、及硬烤后完成。但是目前所用的碳黑虽然具有低成本与高黑度的优势,但是碳黑本身也是电导体,因此通常在高温硬烤完成后,会降低黑色矩阵光致抗蚀剂层的表面阻抗,导致欲遮蔽的金属线部分导通,而影响讯号。所以黑色矩阵光致抗蚀剂层的黑色色料亟需要具有高绝缘表面的碳黑。
另一方面,目前以高分子膜包覆碳黑以形成混成碳黑的作法,会使混成碳黑凝胶化而增加含有混成碳黑的光致抗蚀剂组合物的粘度。综上所述,目前亟需新的混成碳黑以解决凝胶化的问题。
【发明内容】
本发明一实施例提供混成碳黑,包括:碳黑核心;以及高分子膜,包覆碳黑核心的所有表面,其中高分子膜包含网状交联的多个高分子主链,以及多个分散侧链键结至高分子主链,其中分散侧链来自于丙烯酸酯系单体,且丙烯酸酯系单体的结构如下:当n=4-7时,R1为H或CH3;以及当n=8-14时,R1为CH3。
本发明一实施例提供涂布组合物,包括上述的混成碳黑。
【附图说明】
图1为本发明一实施例中,混成碳黑的示意图。
【符号说明】
10 混成碳黑;
11 碳黑核心;
13 高分子膜;
13A 网状交联的高分子主链;
13B 分散侧链。
【具体实施方式】
如图1所示,一实施例的混成碳黑10具有高分子膜13,其包覆碳黑核心11的所有表面,且高分子膜13包含网状交联的高分子主链13A,以及键结至高分子主链13A上的分散侧链13B。上述混成碳黑具有高的热裂解温度与优良的抗溶剂特性,使包含其的遮光材料能在高温下不易热裂解而导致碳黑表面电性裸露。此外,当混成碳黑配制成涂布组合物(如黑色油墨)时,有机溶剂只会膨润而不会溶解高分子膜。
上述碳黑核心具有紧密型碎形结构与十分光滑的表面,其表面性质可以碎形维度表示,比如质量碎形维度(mass fractal dimension、Dm)与表面碎形维度(surfacefractal dimension、Ds)。表面碎形维度(Ds)可表现碎形体的界面粗糙度。在一实施例中,碳黑核心的表面碎形维度(Ds)可介于2至3之间。Ds越小则碳黑核心的碎形体界面越平滑,而Ds越大则碳黑核心的碎形体界面越粗糙。质量碎形维度(Dm)可表现聚集体型态。在一实施例中,碳黑核心的质量碎形维度(Dm)介于1至3之间。Dm越小则碳黑核心的碎形体偏向线性型,而Dm越大则碳黑核心的碎形体较偏向紧密型(如紧密球形)。在一实施例中,上述具有紧密型碎形结构以及光滑界面的碳黑核心质量碎形维度(Dm)可介于2-3之间,且表面碎形维度(Ds)可介于2-2.5之间。
在一实施例中,上述高分子膜由苯乙烯系单体、交联剂、与丙烯酸酯系单体共聚而成。苯乙烯系单体通常能吸附于碳黑表面,因此与碳黑间有良好的交互作用力。此外,苯乙烯系单体可提升高分子膜的热裂解温度。在一实施例中,苯乙烯系单体具有单一乙烯基,其可为苯乙烯(styrene)、甲基丙烯酸苯甲酯(benzyl methacrylate)、或丙烯酸苯甲酯(benzyl acrylate)。
交联剂具有两个或两个以上的乙烯基,使高分子主链交联成网状。举例来说,交联剂可为二乙烯基苯(divinyl benzene)、乙二醇二甲基丙烯酸酯(ethylene glycoldimethacrylate)、1,4-丁二醇二丙烯酸酯(1,4-butanediol diacrylate)、季戊四醇三丙烯酸酯(pentaerythritol triacrylate)、乙氧基化三甲基丙烷三丙烯酸酯(ethoxylatedtrimethylpropane triacrylate)、二季戊四醇五丙烯酸酯(dipentaerythritolpentaacrylate)、乙氧基化季戊四醇四丙烯酸酯(ethoxylated pentaerythritoltertaacrylate)、季戊四醇四丙烯酸酯(pentaerythritol tertaacrylate)、二季戊四醇六丙烯酸酯(dipentaerythritol hexaacrylate)、或上述的组合。在一实施例中,交联剂为二乙烯基苯(divinyl benzene)。
上述丙烯酸酯系单体在聚合后,形成的分散侧链将键结至高分子主链。分散侧链可降低油墨粘度与提高分散性。在一实施例中,丙烯酸酯系单体的化学结构式如下:
在式1中,当n=4-7时,R1为H或CH3。当n=8-14时,R1为CH3。值得注意的是,n的数目超过7且R1为H时,会使包含混成碳黑的组合物的粘度大幅增加。另一方面,当n大于14时,即使采用R1为CH3的丙烯酸酯,也无法使包含混成碳黑的组合物的粘度下降。在一实施例中,丙烯酸酯系单体为甲基丙烯酸十二烷基酯(LMA)。在一实施例中,丙烯酸酯系单体为甲基丙烯酸己酯(HMA)。在一实施例中,丙烯酸酯系单体为丙烯酸己酯(HA)。
在一实施例中,苯乙烯系单体与交联剂的摩尔比介于70:1至100:1之间。若交联剂的比例过低,则高分子主链的交联度不足,而无法形成高分子膜包覆碳黑的所有表面。若交联剂的比例过高,则混成碳黑的高分子膜硬度过高且易脆。在一实施例中,苯乙烯系单体与丙烯酸酯系单体的摩尔比介于17:1至23:1之间。若丙烯酸酯系单体的比例过低,则所配制的黑色光致抗蚀剂液粘度过高。若丙烯酸酯系单体的比例过高,则分散侧链分散功能失效,引发混成碳黑凝胶化。
在一实施例中,高分子膜与碳黑核心的重量比介于5:1至30:1之间。若高分子膜的比例过高,则具有混成碳黑的膜层的光学密度过低。若高分子膜的比例过低,则无法有效遮蔽碳黑,且具有混成碳黑的膜层的表面阻抗值过低。在一实施例中,高分子膜的膜厚与碳黑核心的粒径比介于0.5:1至1.5:1之间。若高分子膜的膜厚过厚,则具有混成碳黑的膜层的光学密度过低。若高分子膜的膜厚过薄,则无法有效遮蔽碳黑,且具有混成碳黑的膜层的表面阻抗值过低。在一实施例中,混成碳黑的粒径介于40nm至150nm之间,例如介于80nm至130nm之间。若混成碳黑的粒径过大,则粒径间空隙过大,所配制的黑色光致抗蚀剂液的光学密度低下,降低遮蔽效果。若混成碳黑的粒径过小,则所配制的黑色光致抗蚀剂液粘度过高,影响后续涂布制程参数设计。
上述混成碳黑的制备方法,可包含(1)碳黑微细化处理及(2)合成混成碳黑。碳黑微细化处理的方法包含配制碳黑分散液,并选用研磨方法如球磨、砂磨、高速冲击式粉碎机、或类似方法。在一实施例中,使用纳米研磨法进行碳黑微细化处理,以得特定质量碎形维度(Dm)及表面碎形维度(Ds)的碳黑核心。
举例来说,碳黑微细化处理的方法可具有以下步骤:首先,取裸碳黑材料,以四氢呋喃(THF)清洗数次与烘干,可除去碳黑表面的污物。接着,配制碳黑/第一表面活性剂/水的分散液(固含量9~15wt%),控温搅拌(50~100rpm/20~30min)后,将所得的分散液倒入纳米研磨机的研磨槽中,以进行纳米研磨微细化处理。研磨珠可选用小于或等于0.1mm的陶瓷研磨珠(如高密度、高硬度、高稳定、与耐磨耗的球形氧化锆珠)、钢材研磨珠(如火碳钢材质制成的球形铸钢球、铬钢研磨珠以及轴承钢硬化处理的研磨珠),且研磨温度可为15~25℃。研磨速度一开始可先以低转速研磨(500~1500rpm),然后逐步调高转速(1500~2500rpm),直到粒径不再剧烈变动为止。微细化的碳黑水溶液经离心分离,并以甲醇清洗数次后通过减压干燥形成碳黑粉末,以便后续合成混成碳黑使用。上述研磨珠的粒径若过大,则研磨后的碳黑粒径无法有效降低与均匀分布。上述研磨速度若过快,则表面活性剂在碳黑表面润湿会失效,导致过磨现象。研磨速度若过慢,则碳黑间碰撞力道不足,降低研磨效果。上述第一表面活性剂作为分散剂,主要是提供碳黑粉体在水相中的分散与稳定,使吸附于碳黑上的单体能在稳定的微胞中聚合成高分子链,且高分子链又交联成网状以形成高分子膜。第一表面活性剂的种类没有特别限制,阴离子型、阳离子型、非离子型、或高分子型表面活性剂均可,比如十二烷基硫酸钠(SDS)。此外,可进一步添加第二表面活性剂(与第一表面活性剂不同,可例如为疏水性(hydrophobic)表面活性剂),以抑制聚合反应过程中表面活性剂/单体组成物/碳黑微胞的奥斯瓦尔德熟化(Ostwald ripening)现象,避免最后所得的碳黑粒径严重不均匀。第二表面活性剂并没有特别限制,只要能与第一表面活性剂相容即可,比如十六烯(hexadecane)。
在一实施例中,合成混成碳黑的方式如下。先配制碳黑分散液,亦即在具有一表面活性剂的水溶液中添加已经过微细化处理的碳黑。经搅拌后,使之形成稳定分散的碳黑分散液。接者,将苯乙烯系单体、交联剂、丙烯酸酯系单体、与起始剂一起填入另一容器,待搅拌成均一相单体液体后,添加入碳黑分散液中。值得注意的是,此时仍需持续搅拌一段时间(约30-40分钟),以便单体能溶入碳黑微胞内并吸附于碳黑表面。最后进行聚合反应。聚合反应方式可依起始剂种类调整,起始剂可包括热起始剂或光起始剂,以热起始剂为例,聚合反应在氮气下升温至热起始剂热裂解温度65-70℃以上开始进行聚合反应,在反应的最后一段时间,可以再升温至更高的温度75-85℃以便将未反应的单体反应完全,反应时间可为2-20小时。若反应温度过高,则起始剂一开始即热裂解,容易引发单体/碳黑微胞间的跨区反应。若反应温度过低,则起始剂无法完全热裂解。需注意的是,热起始剂产生热裂解后的成分必须不能使网状交联高分子膜带电荷,以避免所得的混成碳黑失去绝缘特性。因此,需根据使用的单体搭配合适的热起始剂。上述热起始剂可采用常见的偶氮二异丁晴(AIBN)。上述表面活性剂的种类没有特别限制,阴离子型、阳离子型、非离子型、或高分子型表面活性剂均可,一般采用高HLB(亲水亲油平衡,hydrophile-lipophile balance)值的十二烷基磺酸钠(SDS)。最后,将合成好的混成碳黑分散液与适量甲醇混合后分批装入离心瓶中,并在离心机中进行离心分离;接着将上层液取出,并重新填入新鲜甲醇与离心分离。上述清洗步骤需重复数次,使表面活性剂被清洗干净。最后将清洗完全的混成碳黑从离心瓶底部取出并减压浓缩干燥,即可得到粉状的混成碳黑。
上述混成碳黑可用于涂布组合物。在一实施例中,涂布组合物可含有溶剂,且混成碳黑的固含量可介于15-30wt%(溶液中混成碳黑平均粒径为170-250nm)。上述溶剂可为任何使混成碳黑分散于其中的溶剂,比如:丙二醇甲醚醋酸酯(propylene glycolmonomethyl ether acetate,简称PGMEA)、环己酮、丙二醇、或丙二醇单甲基醚(propyleneglycol methyl ether,简称PGME)。此外,涂布组合物亦可包含分散剂如烃基官能羧酸(如BYK-108)、丙烯酸共聚合物(如BYK-116)、不饱和聚胺酸的聚酰胺(如BYK-130)、含颜料亲和基团高分子共聚合物(如BYK-163,164,167,170,171,174,182,183,184,185,191,192,9075,9076,9077)、丙烯酸高分子共聚合物(如BYK-2000,2001)、或丙烯酸酯共聚合物(如BYK-2050,2070)。分散剂的比例可介于1wt%-30wt%之间,以溶剂与混成碳黑的总重为基准。
在一实施例中,上述涂布组合物可搭配负型感光光致抗蚀剂以作为遮光涂料。在一实施例中,作为遮光涂料的涂布组合物的粘度小于20cP,例如小于或等于10cP且大于0cP。上述负型感光光致抗蚀剂包括组成重量比为5-40wt%的多官能基单体。这些多官能基单体含有两个以上的碳碳双键。举例来说,多官能基单体可为丙烯酸酯类单体如乙二醇基二甲基丙烯酸甲酯(ethylene glycol dimethacrylate)、1,4-丁二醇基二丙烯酸酯(1,4-butanediol diacrylate)、二甘醇二丙烯酸酯(diethylene glycol diacrylate)、季戊四醇三丙烯酸酯(pentaerythritol triacrylate)、乙氧基化季戊四醇三丙烯酸酯(ethoxylated pentaerythritol triacrylate)、二季戊四醇五丙烯酸酯(dipentaetrythritol pentaacrylate)、乙氧基化季戊四醇四丙烯酸酯(ethoxylatedpentaerythritol tetraacrylate)、季戊四醇四丙烯酸酯((pentaerythritoltetraacrylate)、二季戊四醇六丙烯酸酯(dipentaerythritol hexaacrylate)、或其他合适的丙烯酸酯。
负型感光光致抗蚀剂亦包含20-60wt%的粘着剂,以与多官能基单体交联形成网状结构。粘着剂的重均分子量介于3000-100000,且平均聚合度介于1.2-4.3。在一实施例中,粘着剂的重均分子量介于6000-40000,且平均聚合度介于1.2-3.8。粘着剂为水溶性粘着剂或碱溶性粘着剂,且酸基单体的摩尔比介于10-50%,或介于15-30%。粘着剂亦具有与上述多官能基单体交联的不饱和酯类,使粘着剂具有涂布性、与基材的附着性、以及足够高的玻璃转换温度。不饱和酯类包括甲基丙烯酸酯类,如甲基丙烯酸甲酯(methylmethacrylate)、甲基丙烯酸苯甲酯(benzyl methacrylate)、甲基丙烯酸乙酯(ethylmethacrylate)、甲基丙烯酸2-羟基乙酯(2-hydroxyethyl methacrylate)、甲基丙烯酸甲羟基丙酯(hydroxypropyl methacrylate)、甲基丙烯酸异丁酯(isobutyl methacrylate)、其他合适的甲基丙烯酸酯;或丙烯酸酯类,如丙烯酸甲酯(methyl acrylate)、丙烯酸苯甲酯(benzyl acrylate)、丙烯酸乙酯(ethyl acrylate)、丙烯酸2-羟基乙酯(2-hydroxyethyl acrylate)、丙烯酸羟基丙基酯(hydroxylpropyl acrylate)、丙烯酸异丁基酯(isobutyl acrylate)、或其他合适的丙烯酸酯。
上述粘着剂与多官能基单体交联的方式为自由基聚合,包括热聚合、光聚合、或上述的组合。感光起始剂感光波长低于400纳米的紫外线。感光起始剂可占负型感光光致抗蚀剂0.1-10wt%,包括:苯乙酮类如2-甲基-1-(4-(甲基硫基)苯基-2-吗啉基丙烷(2-methyl-1-(4-(methylthio)phenyl)-2-morpholino-propane)、1-羟基环己基苯基酮(1-hydroxycyclohexyl phenyl ketone)、二乙氧基苯乙酮(diethoxyacetophenone)、2-羟基-2-甲基-1-苯基-丙烷-1-酮(2-hydroxy-2-methyl-1-phenyl-propane-1-one)、2-苄基-2-(二甲基氨基)-1-[4-(吗啉基)苯基]-1-丁酮(2-benzyl-2-(dimethylamino)-1-[4-(morpholinyl)phenyl]-1-butanone)、其他合适的苯乙酮;安息香类如安息香(benzoin)、安息香甲基醚(benzoin methyl ether)、其他合适的安息香;二苯基酮类如二苯甲酮(benzophenone)、4-苯基二苯甲酮(4-phenyl benzophenone)、羟基二苯甲酮(hydroxylbenzophenone)、或其他合适的二苯甲酮;噻吨酮类如异丙基噻吨酮(isopropylthioxanthone)、2-氯基噻吨酮(2-chlorothioxanthone)、或其他合适的噻吨酮;蒽醌类如2-乙基蒽醌(2-ethylanthraquinone)、或其他合适的蒽醌。上述光起始剂除可单一使用外,亦可混合使用以得到较快的感光速度,比如异丙基噻吨酮混合2-甲苯基-2-(二甲基氨基)-1-[4-(吗啉基)苯基]-1-丁酮。
感热起始剂的热裂解温度介于30-200℃。感热起始剂可占负型感光光致抗蚀剂的0.01-1wt%,包括偶氮类如2,2’-偶氮双(2,4-二甲基正戊腈)(2,2’-azobis(2,4-dimethylvaleronitrile))、二甲基-2,2’-偶氮双(2-丙酸甲酯)(dimethyl 2,2’-azobis(2-methylpropionate)、2,2-偶氮双异丁腈(2,2-azobisisobutyronitrile,以下简称AIBN)、2,2-偶氮双(2-甲基异丁腈)(2,2-azobis(2-methylisobutyronitrile))、1,1’-偶氮双(环己烷-1-腈)1,1’-azobis(cyclohexane-1-carbonitrile))、2,2’-偶氮双[N-2-丙基-2-甲基丙酰胺](2,2’-azobis[N-(2-propenyl)-2-methylpropionamide])、1-[(氰基-1-甲基乙基)-偶氮基]甲酰胺(1-[(cyano-1-methylethyl)azo]formamide)、2,2’-偶氮双(N-丁基-2-甲基丙酰胺)(2,2’-azobis(N-butyl-2-methylpropionamide))、2,2’-偶氮双(N-环己基-2-甲基丙酰胺)(2,2’-azobis(N-cyclohexyl-2-methylpropionamide)、或其他合适的偶氮类起始剂;过氧化物类包括苯甲酰基过氧化物(benzoyl peroxide)、1,1-双(叔丁基过氧基)环己烷(1,1-bis(tert-butylperoxy)cyclohexane)、2,5-双(叔丁基过氧基)-2,5-二甲基环己烷(2,5-bis(tert-butylperoxy)-2,5-dimethylcyclohexane)、2,5-双(叔丁基过氧基)-2,5-二甲基-3-环己炔(2,5-bis(tert-butylperoxy)-2,5-dimethyl-3-cyclohexyne)、双(1-(叔丁基过氧基)-1-甲基乙基)苯(bis(1-(tert-butylpeorxy)-1-methy-ethyl)benzene)、叔丁基过氧化氢(tert-butyl hydroperoxide)、叔丁基过氧化物(tert-butyl peroxide)、叔丁基过氧基苯甲酸酯(tert-butyl peroxybenzoate)、氢过氧化枯烯(Cumene hydroperoxide)、环己酮基过氧化物(cyclohexanone peroxide)、二枯基过氧化物(dicumyl peroxide)、过氧化月桂酰(lauroyl peroxide)、或其他合适的过氧化物。上述的热起始剂除可单一使用外,亦可混合使用,应视需要而定。
除了上述多官能基单体、粘着剂与起始剂外,本发明的负型感光光致抗蚀剂的组成可还包括1-10wt%的添加物如硬化加速剂、表面活性剂、流平剂、消泡剂、硬质填充剂、或接着促进剂。
为了让本发明上述内容和其他目的、特征、和优点能更明显易懂,下文特举数个实施例作详细说明如下:
实施例
在下述实施例中,粒径测量系使用高浓度粒径、Zeta电位及分子量仪(MalvernZetasizer nanov5(Nano ZS))。碳黑形态分析系使用小角度X光散射仪(Bruker NanostarSAXS)。粘度测量系使用粘度计(BROOKFIELD LVDV-Ⅱ+P)。
制备例
制备例1(纳米研磨法碳黑微细化处理)
首先称取适量裸碳黑材料(MOGUL L,购自Cabot),以THF清洗数次后烘干以除去碳黑表面的污物。接着以十二烷基硫酸钠(sodium dodecyl sulfate(SDS),购自ACROS)作为分散剂,配制碳黑/SDS/水的分散液(固含量约13wt%),接着进行控温搅拌(50rpm/30min),再将分散液倒入纳米研磨机(Just Nano,JBM-B035(BatchType),选用0.1mm锆珠)的研磨槽中,以进行纳米研磨微细化处理。在研磨温度(20℃)下先以低转速研磨(500rpm),然后逐步调高转速至2000rpm,直到粒径不再剧烈变动为止。微细化的碳黑水溶液经离心分离后以甲醇清洗数次,通过减压干燥即形成微细化碳黑。上述微细化碳黑的平均粒径约为109nm、质量碎形维度(mass-fractal dimension,Dm)为2.3,且表面碎形维度(surface-fractaldimension,Ds)约为2.0,显示经过研磨微细化的碳黑具有紧密碎形聚集体和十分光滑的表面。
制备例2(负型感光光致抗蚀剂液)
(1)压克力粘着剂的制备
首先取160g的单甲基醚丙二醇乙酸酯(propylene glycol monomethyl etheracetate,简称PGMEA,购自Sigma-Aldrich)置于4升反应瓶内,于氮气下加热至90℃,以350rpm的速率搅拌。接着按计量混合0.8g的偶氮二异丁腈(azobisisobutyronitrile(AIBN),购自Showa)、0.81g的硫醇(thiol,购自Sigma-Aldrich)、60.01g的甲基丙烯酸苯甲酯(benzyl methacrylate(BzMa),购自Sigma)、26g的甲基丙烯酸(methyl acrylic acid(MAA),购自Sigma-Aldrich)、10g的甲基丙烯酸2-羟基乙酯(2-hydroxyethylmethacrylate(2-HEMA),购自Sigma-Aldrich)、40.02g的甲基丙烯酸甲酯(MethylMethacrylate(MMA))、以及40g的PGMEA后,将此混合物逐步滴入反应瓶中的PGMEA内,滴完后反应2小时,即得压克力粘着剂溶液,其固体含量为38.72%。
(2)光致抗蚀剂液的配制
取300g的压克力粘着剂溶液、50g的二季戊四醇六丙烯酸酯(dipentaerythritolhexaacrylate(DPHA),购自Sartomer)及20g的光起始剂OXE-02(购自CIBA),共同溶于300g的PGMEA与异丙醇(IPA)的共溶剂中(w/w=9/1)即制得光致抗蚀剂液,其粘度为5.94cP。
实施例1(混成碳黑CB-LMA)
取200g去离子水、2.12g的微细化碳黑(由制备例1所得)、与2.78g的SDS置入250mL的反应瓶中并搅拌混合以配制碳黑分散液。接着取0.18g的AIBN(购自Showa/纯度99%)、2.21g的甲基丙烯酸十二烷基酯(lauryl methacrylate(LMA),购自Aldrich)、21.1g的苯乙烯(购自ACROS)、与0.38g的1,2-二乙烯基苯(1,2-divinylbenzene(DVB),购自TCI)置于另一烧杯中,搅拌成均一相后,直接倒入碳黑分散液中混合。之后在氮气下加热上述混合物至65℃并于65℃下反应1小时,再升温至75℃并于75℃下反应16小时,即得混成碳黑分散液,且碳黑表面包覆有高分子膜。上述高分子膜具有网状交联的高分子主链如(苯乙烯-DVB-LMA)共聚物,且LMA形成的分散侧链如长烷基键结至高分子主链。上述混成碳黑分散液的固含量为15.7wt%,且混成碳黑的平均粒径为107nm。接着纯化与干燥混成碳黑如下:将混成碳黑分散液与甲醇混合后分批装入离心瓶中,再将离心瓶置入离心机(HERMLE Z300)中并以转速4500rpm离心10分钟以进行离心分离。接着取出上层液,再重新填入新鲜甲醇后再次离心分离。上述离心清洗步骤重复数次,直到离心瓶底部的固体的Zeta电位值接近零(所使用的仪器为Malvern Zetasizer nanov5(Nano ZS)),即SDS已被清洗干净。最后将清洗完全的混成碳黑从离心瓶底部取出并减压浓缩干燥,即得到粉状的混成碳黑(简称CB-LMA),其中高分子膜中单体的摩尔比为:苯乙烯/DVB=70/1,苯乙烯/LMA=23/1。
实施例1-1(CB-LMA混成碳黑分散液)
将实施例1所得的混成碳黑以颜料分散法方式配制碳黑分散液。首先,取4g的混成碳黑(CB-LMA)、4g的分散剂(BYK 191)、与20g的有机溶剂(PGMEA)放入已装入1/2磨罐体积的0.05mm直径锆球的PE磨罐中,并以球磨机进行混合分散,以得混成碳黑分散液。混成碳黑分散液的总固含量为28.6wt%,且碳黑固含量为15wt%。经Zeta表面电位监测(使用仪器为Malvern Zetasizer nanov5(Nano ZS)),显示混成碳黑分散液的zeta表面电位十分接近零。上述混成碳黑分散液中的混成碳黑的平均粒径为206nm,且混成碳黑分散液的粘度为14.4cP。
实施例1-2(CB-LMA黑色光致抗蚀剂液)
将实施例1所得的混成碳黑以颜料分散法方式配制黑色光致抗蚀剂液。首先,取4g的混成碳黑(CB-LMA)与20g的负型感光光致抗蚀剂液放入已装入1/2磨罐体积的0.05mm直径锆球的PE磨罐中,并以球磨机进行混合分散,以得黑色光致抗蚀剂液,其总固含量为30wt%,且混成碳黑固含量为15wt%。黑色光致抗蚀剂液中混成碳黑的平均粒径为228nm。当粘度计转速为50rpm时,黑色光致抗蚀剂液的粘度为8.88cP。当粘度计转速为20rpm时,黑色光致抗蚀剂液的粘度为9.00cP。
实施例2
与实施例1类似,差别在于将苯乙烯/DVB的摩尔比调整至100/1,其余起始物的用量制程步骤参数均与实施例1相同。
接着以实施例1-2的方法调配CB-LMA的黑色光致抗蚀剂液。实施例2的黑色光致抗蚀剂液中的混成碳黑的平均粒径为245nm。当粘度计转速为50rpm时,黑色光致抗蚀剂液的粘度为8.23cP。当粘度计转速为20rpm时,黑色光致抗蚀剂液的粘度为9.18cP。
实施例3
与实施例1类似,差别在于将苯乙烯/LMA的摩尔比调整至17/1,其余起始物的用量制程步骤参数均与实施例1相同。
接着以实施例1-2的方法调配CB-LMA的黑色光致抗蚀剂液。实施例3的黑色光致抗蚀剂液中的混成碳黑的平均粒径为238nm。当粘度计转速为50rpm时,黑色光致抗蚀剂液的粘度为7.9cP。当粘度计转速为20rpm时,黑色光致抗蚀剂液的粘度为8.56cP。
上述实施例1至3的混成碳黑CB-LMA调配的黑色光致抗蚀剂液的性质比较如表1所示:
表1
实施例4(混成碳黑CB-HA)
取200g去离子水、2.0g的微细化碳黑(由制备例1所得)、与2.78g的SDS置入250mL的反应瓶中并搅拌混合以配制碳黑分散液。接着取0.12g的AIBN、1.38g的丙烯酸正己脂(Hexyl acrylate(HA),购自Aldrich)、21.05g的苯乙烯、与0.38g的DVB置于另一烧杯中,搅拌成均一相后,直接倒入碳黑分散液中混合。之后在氮气下加热上述混合物至65℃并于65℃下反应1小时,再升温至75℃并于75℃下反应16小时,即得混成碳黑分散液,且碳黑表面包覆有高分子膜。上述高分子膜具有网状交联的高分子主链如(苯乙烯-DVB-HA)共聚物,且HA形成的分散侧链如长烷基键结至高分子主链。上述混成碳黑分散液的固含量为9.58wt%,且混成碳黑的平均粒径为99nm。接着纯化与干燥混成碳黑(如实施例1),即得到粉状的混成碳黑(简称CB-HA),其中高分子膜中单体的摩尔比为:苯乙烯/DVB=70/1,苯乙烯/HA=23/1。
实施例4-1(CB-HA混成碳黑分散液)
与实施例1-1类似,差别在将CB-LMA置换为CB-HA。实施例4-1的混成碳黑分散液中的混成碳黑的平均粒径为178nm,且混成碳黑分散液的粘度为22.1cP。
实施例4-2(CB-HA黑色光致抗蚀剂液)
与实施例1-2类似,差别在将CB-LMA置换为CB-HA。实施例4-2的黑色光致抗蚀剂液中的混成碳黑的平均粒径为200nm。当粘度计转速为50rpm时,黑色光致抗蚀剂液的粘度为15.0cP。当粘度计转速为20rpm时,黑色光致抗蚀剂液的粘度为19.0cP。
实施例5(混成碳黑CB-HMA)
取200g去离子水、2.0g的微细化碳黑(由制备例1所得)、与2.78g的SDS置入250mL的反应瓶中并搅拌混合以配制碳黑分散液。接着取0.12g的AIBN、1.44g的甲基丙烯酸正己脂(Hexyl methacrylate(HMA),购自Aldrich)、21.05g的苯乙烯、与0.38g的DVB置于另一烧杯中,搅拌成均一相后,直接倒入碳黑分散液中混合。之后在氮气下加热上述混合物至65℃并于65℃下反应1小时,再升温至75℃并于75℃下反应16小时,即得混成碳黑分散液,且碳黑表面包覆有高分子膜。上述高分子膜具有网状交联的高分子主链如(苯乙烯-DVB-HMA)共聚物,且HMA形成的分散侧链如长烷基键结至高分子主链。上述混成碳黑分散液的固含量为8.1wt%,且混成碳黑的平均粒径为120nm。接着纯化与干燥混成碳黑(如实施例1),即得到粉状的混成碳黑(简称CB-HMA),其中高分子膜中单体的摩尔比为:苯乙烯/DVB=70/1,苯乙烯/HMA=23/1。
实施例5-1(CB-HMA混成碳黑分散液)
与实施例1-1类似,差别在将CB-LMA置换为CB-HMA。实施例5-1的混成碳黑分散液中的混成碳黑的平均粒径为163nm,且混成碳黑分散液的粘度为23cP。
实施例5-2(CB-HMA黑色光致抗蚀剂液)
与实施例1-2类似,差别在将CB-LMA置换为CB-HMA。实施例5-2的黑色光致抗蚀剂液中的混成碳黑的平均粒径为182.2nm。粘度计转速为50rpm时,黑色光致抗蚀剂液的粘度为15.2cP。当粘度计转速为20rpm时,黑色光致抗蚀剂液的粘度为17.8cP。
比较例1混成碳黑(CB-LA)
取100g去离子水、1.0g的微细化碳黑(由制备例1所得)、与1.4g的SDS置入250mL的反应瓶中并搅拌混合以配制碳黑分散液。接着取0.054g的AIBN、1.02g的丙烯酸月桂酯(lauryl acrylate(LA),购自Aldrich)、10.63g的苯乙烯(购自ACROS)、与0.19g的DVB置于另一烧杯中,搅拌成均一相后,直接倒入碳黑分散液中混合。之后在氮气下加热上述混合物至65℃并于65℃下反应1小时,再升温至75℃并于75℃下反应16小时,即得混成碳黑分散液,且碳黑表面包覆有高分子膜。上述高分子膜具有网状交联的高分子主链如(苯乙烯-DVB-LA)共聚物,且LA形成的分散侧链如长烷基键结至高分子主链。上述混成碳黑分散液的固含量为11.34wt%,且混成碳黑的平均粒径为92nm。接着纯化与干燥混成碳黑(如实施例1),即得到粉状的混成碳黑(简称CB-LA),其中高分子膜中单体的摩尔比为:苯乙烯/DVB=70/1,苯乙烯/LA=23/1。
比较例1-1(CB-LA混成碳黑分散液)
与实施例1-1类似,差别在将CB-LMA置换为CB-LA。比较例1-1的混成碳黑分散液中的混成碳黑的平均粒径为277nm,且混成碳黑分散液的粘度为21.3cP。
比较例1-2(CB-LA黑色光致抗蚀剂液)
与实施例1-2类似,差别在将CB-LMA置换为CB-LA。比较例1-2的黑色光致抗蚀剂液中的混成碳黑的平均粒径为257nm。当粘度计转速为50rpm时,黑色光致抗蚀剂液的粘度为49.1cP。当粘度计转速为20rpm时,黑色光致抗蚀剂液的粘度为75.4cP。
比较例2混成碳黑(CB-SMA)
取200g去离子水、2.0g的微细化碳黑(由制备例1所得)、与2.78g的SDS置入250mL的反应瓶中并搅拌混合以配制碳黑分散液。接着取0.12g的AIBN、2.99g的甲基丙烯酸硬脂酯(Stearyl methacrylate(SMA),购自Aldrich)、21.05g的苯乙烯(购自ACROS)、与0.38g的DVB置于另一烧杯中,搅拌成均一相后,直接倒入碳黑分散液中混合。之后在氮气下加热上述混合物至65℃并于65℃下反应1小时,再升温至75℃并于75℃下反应16小时,即得混成碳黑分散液,且碳黑表面包覆有高分子膜。上述高分子膜具有网状交联的高分子主链如(苯乙烯-DVB-SMA)共聚物,且SMA形成的分散侧链如长烷基键结至高分子主链。上述混成碳黑分散液的固含量为8.05wt%,且混成碳黑的平均粒径为106nm。接着纯化与干燥混成碳黑(如实施例1),即得到粉状的混成碳黑(简称CB-SMA),其中高分子膜中单体的摩尔比为:苯乙烯/DVB=70/1,苯乙烯/SMA=23/1。
比较例2-1(CB-SMA混成碳黑分散液)
与实施例1-1类似,差别在将CB-LMA置换为CB-SMA。比较例2-1的混成碳黑分散液中的混成碳黑的平均粒径为255nm,且混成碳黑分散液的粘度为32.4cP。
比较例2-2(CB-SMA黑色光致抗蚀剂液)
与实施例1-2类似,差别在将CB-LMA置换为CB-SMA。比较例2-2的黑色光致抗蚀剂液中的混成碳黑的平均粒径为279.3nm。当粘度计转速为50rpm时,黑色光致抗蚀剂液的粘度为58.3cP。当粘度计转速为20rpm时,黑色光致抗蚀剂液的粘度为89.4cP。
比较例3
取200g去离子水、2.12g的微细化碳黑(由制备例1所得)、与2.78g的SDS置入250mL的反应瓶中并搅拌混合以配制碳黑分散液。接着以实施例1-2的方法调配碳黑的黑色光致抗蚀剂液。比较例3的黑色光致抗蚀剂液中的混成碳黑的平均粒径为185.4nm。当粘度计转速为50rpm时,黑色光致抗蚀剂液的粘度为106.5cP。当粘度计转速为20rpm时,黑色光致抗蚀剂液的粘度为106.5cP。
上述实施例1、实施例4、实施例5、比较例1、比较例2、与比较例3的黑色光致抗蚀剂液的性质比较如表2所示:
表2
虽然本发明已以数个实施例揭露如上,然其并非用以限定本发明,任何本领域技术人员在不脱离本发明的精神和范围内,应可作任意的更动与润饰,因此本发明的保护范围应以所附权利要求书所界定的范围为准。
Claims (7)
1.一种混成碳黑,包括:
碳黑核心;以及
高分子膜,包覆该碳黑核心的所有表面,
其中该高分子膜包含网状交联的多个高分子主链,以及键结至该高分子主链的多个分散侧链,
其中该些分散侧链来自于丙烯酸酯系单体,且丙烯酸酯系单体的结构如下:
当n=6时,R1为H或CH3;以及
当n=8-14时,R1为CH3,
其中高分子膜由苯乙烯系单体、交联剂、与丙烯酸酯系单体共聚而成,且苯乙烯系单体与丙烯酸酯系单体的摩尔比为17:1至23:1;以及
其中混成碳黑的粒径为40nm至150nm。
2.如权利要求1所述的混成碳黑,其中苯乙烯系单体与交联剂的摩尔比为70:1至100:1。
3.如权利要求1所述的混成碳黑,其中该高分子膜与该碳黑核心的重量比为5:1至30:1。
4.如权利要求1所述的混成碳黑,其中该高分子膜的膜厚与该碳黑核心的粒径比为0.5:1至1.5:1。
5.如权利要求1所述的混成碳黑,其中该碳黑核心的质量碎形维度为2至3,且该碳黑核心的表面碎形维度为2至2.5。
6.一种涂布组合物,包括权利要求1所述的混成碳黑。
7.如权利要求6所述的涂布组合物,还包含光致抗蚀剂。
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