JP2020161673A - 硬化性組成物、ドライフィルム、硬化物および電子部品 - Google Patents
硬化性組成物、ドライフィルム、硬化物および電子部品 Download PDFInfo
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- JP2020161673A JP2020161673A JP2019060301A JP2019060301A JP2020161673A JP 2020161673 A JP2020161673 A JP 2020161673A JP 2019060301 A JP2019060301 A JP 2019060301A JP 2019060301 A JP2019060301 A JP 2019060301A JP 2020161673 A JP2020161673 A JP 2020161673A
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- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WZESLRDFSNLECD-UHFFFAOYSA-N phenyl prop-2-eneperoxoate Chemical class C=CC(=O)OOC1=CC=CC=C1 WZESLRDFSNLECD-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- CCDXIADKBDSBJU-UHFFFAOYSA-N phenylmethanetriol Chemical compound OC(O)(O)C1=CC=CC=C1 CCDXIADKBDSBJU-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- QCTJRYGLPAFRMS-UHFFFAOYSA-N prop-2-enoic acid;1,3,5-triazine-2,4,6-triamine Chemical class OC(=O)C=C.NC1=NC(N)=NC(N)=N1 QCTJRYGLPAFRMS-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- LJFWQNJLLOFIJK-UHFFFAOYSA-N solvent violet 13 Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O LJFWQNJLLOFIJK-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229950009390 symclosene Drugs 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/075—Silicon-containing compounds
-
- 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
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials For Photolithography (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Epoxy Resins (AREA)
Abstract
Description
(A)アルカリ可溶性樹脂と、
(B)光重合開始剤と、
(C)エポキシ樹脂と、
(D)シリコーン化合物と、
(E)親水性シリカと、
(F)有機揺変剤と、
を含むことを特徴とする硬化性組成物により達成されることが見出された。
本発明の硬化性組成物を、基材上に塗布、乾燥させて得られる乾燥塗膜、または、前記硬化性組成物を、キャリアフィルム上に塗布、乾燥させて得られるドライフィルムが基材にラミネートされてなる塗膜を、硬化させて得られることを特徴とする硬化物、及び
この硬化物を備えることを特徴とする電子部品
によっても達成することができる。
本発明の硬化性組成物は、
(A)アルカリ可溶性樹脂と、
(B)光重合開始剤と、
(C)エポキシ樹脂と、
(D)シリコーン化合物と、
(E)親水性シリカと、
(F)有機揺変剤と、
を含む。
アルカリ可溶性樹脂は、硬化性組成物のアルカリ現像液への溶解、すなわち、アルカリでの現像を可能とする樹脂である。
このようなカルボキシル基含有樹脂の配合量は、硬化性組成物(固形分)中に、20質量%以上80質量%以下、好ましくは30質量%以上70質量%以下の範囲が適当である。カルボキシル基含有樹脂の配合量がこのような範囲内であれば、塗膜強度が低下せず、増粘や、作業性の低下が起こらない。
(B)光重合開始剤は、エネルギー線の照射により、エチレン性不飽和基のラジカル重合を開始させるために添加される。
(C)エポキシ樹脂は、本発明の硬化性組成物を熱硬化させるために添加される化合物である。
(D)シリコーン化合物は、銅張基板(基材)に対する本発明の硬化性組成物のぬれ性を向上させ、そのはじきを抑え、レベリング性を向上させるために配合される。
(E)親水性シリカは、本発明の硬化性組成物の硬化収縮抑制のため、及び得られた硬化物の剛性強化のために添加される。
容量100mlのビーカーにエタノール30mlとシリカ粉末1gを入れて、卓上型超音波洗浄機内で3分間攪拌後、レーザー回折/散乱式粒度分布計(マイクロトラック・ベル社製)マイクロトラックMT−3300を使用し、エタノール溶媒にて体積基準メジアン径(D50)を測定した。
(F)有機揺変剤は、本発明の硬化性組成物中での(E)親水性シリカの凝集・沈殿抑制のため、及び本発明で初めて明らかになったように、本発明の硬化性組成物の硬化物に対するフラックスのぬれ性向上のために添加される。
本発明の硬化性組成物は、(G)酸化防止剤が添加されていることが好ましい。(G)酸化防止剤は、銅張基板(基材)の銅の酸化を抑制することで基材と硬化性組成物の密着性を向上させる。
さらに、本発明の硬化性組成物には、光重合性多官能モノマーを添加することが好ましい。光重合性多官能モノマーは、1分子中に2個以上のエチレン性不飽和基を有する化合物であって、((A)アルカリ可溶性樹脂にエチレン性不飽和基が含まれる場合には、)活性エネルギー線照射による(A)アルカリ可溶性樹脂の光硬化を助け、硬化性組成物を光硬化させるために用いられる。
本発明の硬化性組成物は、キャリアフィルム(支持体)上に塗布、乾燥させて得られるドライフィルムの形態とすることができる。ドライフィルム化に際しては、本発明の硬化性組成物を上記有機溶剤により希釈して適切な粘度に調整し、コンマコーター、ブレードコーター、リップコーター、ロッドコーター、スクイズコーター、リバースコーター、トランスファロールコーター、グラビアコーター、スプレーコーター等でキャリアフィルム上に均一な厚さに塗布し、通常、50〜130℃の温度で1〜30分間乾燥して、乾燥塗膜とすることができる。塗布膜厚については特に制限はないが、一般に、乾燥後の膜厚で0.1〜100μm、好適には0.5〜50μmの範囲で適宜選択される。
上記基材上にパターン印刷した硬化性組成物の硬化物がソルダーレジストとして用いられる場合、部品の実装のためのはんだ付け工程で加熱される。はんだ付けは、手はんだ付け、フローはんだ付け、リフローはんだ付け等のいずれで行われてもよいが、例えば、リフローはんだ付けの場合には、100℃〜140℃で1〜4時間の予熱と、その後、240〜280℃で5〜20秒程度の加熱を複数回(例えば、2〜4回)繰り返してはんだを加熱・溶融させるリフロー工程に供され、冷却後、必要により部品が実装されて電子部品が完成する。
[合成例1]
ビスフェノールF型エポキシ樹脂(エポキシ当量950g/eq、軟化点85℃)380部とエピクロルヒドリン925部をジメチルスルホキシド462.5部に溶解させた後、攪拌下70℃で98.5%NaOH60.9部を100分かけて添加した。添加後さらに70℃で3時間反応を行った。反応終了後、水250部を加え水洗を行った。油水分離後、油層よりジメチルスルホキシドの大半および過剰の未反応エピクロルヒドリンを減圧下に蒸留回収し、残留した副製塩とジメチルスルホキシドを含む反応生成物をメチルイソブチルケトン750部に溶解させ、更に30%NaOH10部を加え、70℃で1時間反応させた。反応終了後、水200部で2回水洗を行った。油水分離後、油層よりメチルイソブチルケトンを蒸留回収して、エポキシ当量310g/eq、軟化点69℃のエポキシ樹脂(a)を得た。得られたエポキシ樹脂(a)は、エポキシ当量から計算すると、前記出発物質ビスフェノールF型エポキシ樹脂におけるアルコール性水酸基6.2個のうち約5個がエポキシ化されたものであった。このエポキシ樹脂(a)310部およびカルビトールアセテート282部をフラスコに仕込み、90℃に加熱・攪拌し、溶解した。得られた溶液を一旦60℃まで冷却し、アクリル酸72部(1モル)、メチルハイドロキノン0.5部、トリフェニルホスフィン2部を加え、100℃に加熱し、約60時間反応させ、酸価が0.2mgKOH/gの反応物を得た。これにテトラヒドロ無水フタル酸140部(0.92モル)を加え、90℃に加熱し、反応を行い、感光性のカルボキシル基含有樹脂ワニス(A−1)を得た。得られたカルボキシル基含有樹脂ワニス(A−1)の固形分濃度は62.5%、固形分酸価(mgKOH/g)は100であった。
クレゾールノボラック型エポキシ樹脂(大日本インキ化学工業(株)製、登録商標“エピクロン”N−695、エポキシ当量:220)220部を撹拌機及び還流冷却器の付いた四つ口フラスコに入れ、カルビトールアセテート214部を加え、加熱溶解した。次に、重合禁止剤としてハイドロキノン0.1部と、反応触媒としてジメチルベンジルアミン2.0部を加えた。この混合物を95〜105℃に加熱し、アクリル酸72部を徐々に滴下し、16時間反応させた。この反応生成物を80〜90℃まで冷却し、テトラヒドロフタル酸無水物106部を加え、8時間反応させ、冷却後、取り出した。
このようにして得られたエチレン性不飽和結合及びカルボキシル基を併せ持つ感光性樹脂は、不揮発分65%、固形物の酸価85mgKOH/g、重量平均分子量Mw約3,500であった。以下、この樹脂溶液をワニス(A−2)と称す。
なお、得られた樹脂の重量平均分子量の測定は、(株)島津製作所製ポンプLC−804、KF−803、KF−802を三本つないだ高速液体クロマトグラフィーにより測定した。
合成例の樹脂溶液及び表1に示す各材料をそれぞれ配合、撹拌機にて予備混合し、次いで3本ロールミルにより混練して硬化性組成物を調製した。表1中、(A−1)〜(A−3)については、溶媒を含むそれぞれの樹脂溶液の質量部を示す。
化学研磨処理により表面を粗化した銅張基板(基材)上にスクリーン版(テトロン100メッシュ)を用いて<1.実施例1〜9および比較例1〜3の硬化性組成物の調製>で調整された各硬化性組成物を銅張基板の全面に膜厚10μmとなるように印刷した。
評価基準は以下のとおりである。
△:はじき有り、且つメッシュ跡が無い、あるいは、はじき無し、且つメッシュ跡有り
×:はじき有り、且つメッシュ跡有り
スクリーン版(テトロン100メッシュ)を用いて<1.実施例1〜4および比較例1〜4の硬化性組成物の調製>で調整された各硬化性組成物を、化学研磨処理により表面を粗化した外形150×95mm、厚さ1.6mmのFR−4、35μm厚銅張積層板の全面に膜厚10μmとなるように印刷した。
*2:2,4,6−トリメチルベンゾイルジフェニルホスフィンオキシド(Omnirad TPO H:IGM Resins B.V.社製)
*3:2−ジメチルアミノ−2−(4−メチル−ベンジル)−1−(4−モルホリン−4−イル−フェニル)−ブタン−1−オン(Omnirad 379:IGM Resins B.V.社製)
*4:ビスフェノールA型エポキシ樹脂(JER(登録商標)−834:三菱ケミカル社製)
*5:イソシアヌル酸トリグリシジル(TEPIC−HP:日産化学工業社製)
*6:ポリエステル変性ポリジメチルシロキサン(BYK(登録商標)−313:ビックケミー・ジャパン社製)
*7:ポリエーテル変性ポリジメチルシロキサン(BYK(登録商標)−300:ビックケミー・ジャパン社製)
*8:球状シリカ(D50=0.6μm)(SFP−130MC:電気化学工業社製)
*9:球状シリカ(D50=0.4μm)(SFP−20M:電気化学工業社製)
*10:ポリヒドロキシカルボン酸エステル(BYK(登録商標)−R 606:ビックケミー・ジャパン社製)
*11:メラミン(メラミン:日産化学工業社製)
*12:メタクリルシラン処理を表面に施した球状シリカ(1.5μmSM−C4:アドマテックス社製)
*13:ジペンタエリスリトールヘキサアクリレート(DPHA:日本化薬社製)
*14:ジシアンジアミド(C0454:東京化成工業社製)
*15:青色顔料(ファーストゲンブルー5380:DIC社製)、表1では固形分の質量部を示す。
*16:黄色顔料(Cromophtal(登録商標) Yellow S1515:BASF社製)、表1では固形分の質量部を示す。
*17:ジプロピレングリコールメチルエーテル(ダワノール(Dowanol)(登録商標)DPM:ダウ・ケミカル日本社製)
Claims (7)
- (A)アルカリ可溶性樹脂と、
(B)光重合開始剤と、
(C)エポキシ樹脂と、
(D)シリコーン化合物と、
(E)親水性シリカと、
(F)有機揺変剤と、
を含むことを特徴とする硬化性組成物。 - (E)親水性シリカのメジアン径D50が、0.2μm以上2.0μm以下であることを特徴とする請求項1に記載の硬化性組成物。
- (F)有機揺変剤の量が、(E)親水性シリカ100質量部に対して0.01質量部以上15質量部以下であり、且つ(D)シリコーン化合物2質量部に対して0.05質量部以上であることを特徴とする請求項1又は2に記載の硬化性組成物。
- (G)酸化防止剤をさらに含むことを特徴とする請求項1〜3の何れか一項に記載の硬化性組成物。
- 請求項1〜4の何れか一項に記載の硬化性組成物を、キャリアフィルム上に塗布、乾燥させて得られることを特徴とするドライフィルム。
- 請求項1〜4の何れか一項に記載の硬化性組成物を、基材上に塗布、乾燥させて得られる乾燥塗膜、または、前記硬化性組成物を、キャリアフィルム上に塗布、乾燥させて得られるドライフィルムが基材にラミネートされてなる塗膜を、硬化させて得られることを特徴とする硬化物。
- 請求項6に記載の硬化物を備えることを特徴とする電子部品。
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