JP2019178287A - インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品 - Google Patents
インクジェット印刷用の硬化性組成物、その硬化物及びその硬化物を有する電子部品 Download PDFInfo
- Publication number
- JP2019178287A JP2019178287A JP2018069537A JP2018069537A JP2019178287A JP 2019178287 A JP2019178287 A JP 2019178287A JP 2018069537 A JP2018069537 A JP 2018069537A JP 2018069537 A JP2018069537 A JP 2018069537A JP 2019178287 A JP2019178287 A JP 2019178287A
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- Prior art keywords
- meth
- curable composition
- acrylate monomer
- acrylate
- manufactured
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 100
- 238000007641 inkjet printing Methods 0.000 title claims abstract description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 105
- 239000000178 monomer Substances 0.000 claims abstract description 84
- 125000006841 cyclic skeleton Chemical group 0.000 claims abstract description 58
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 34
- 238000012986 modification Methods 0.000 claims abstract description 29
- 230000004048 modification Effects 0.000 claims abstract description 29
- 125000003827 glycol group Chemical group 0.000 claims abstract description 19
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 230000001588 bifunctional effect Effects 0.000 claims description 43
- 239000000463 material Substances 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 abstract description 28
- 238000000576 coating method Methods 0.000 abstract description 28
- 238000005476 soldering Methods 0.000 abstract description 15
- 239000004020 conductor Substances 0.000 abstract description 9
- -1 glycol ethers Chemical class 0.000 description 68
- 239000000047 product Substances 0.000 description 35
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- 229920000647 polyepoxide Polymers 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 28
- 239000000126 substance Substances 0.000 description 28
- 229910000679 solder Inorganic materials 0.000 description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- 239000000758 substrate Substances 0.000 description 24
- 238000000034 method Methods 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 16
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 15
- 239000002981 blocking agent Substances 0.000 description 15
- 239000012948 isocyanate Substances 0.000 description 15
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- 230000000052 comparative effect Effects 0.000 description 14
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- 238000012360 testing method Methods 0.000 description 13
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- 239000000412 dendrimer Substances 0.000 description 12
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- 125000003118 aryl group Chemical group 0.000 description 7
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- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 4
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
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- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
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- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
(A)環状骨格を有し、1以上6以下のアルキレンオキサイド変性数を有する(メタ)アクリレートモノマーと、
(B1)環状骨格を有さず、2以上のアルキレングリコール構造を有する二官能(メタ)アクリレートモノマーと、
(B2)環状骨格を有さず、モノアルキレングリコール構造を有する二官能(メタ)クリレートモノマーと、
(C)光重合開始剤と、を含むことにより達成されることが見出された。
本発明のインクジェット印刷用の硬化性組成物(以下、「硬化性組成物」と略記する場合がある。)は、
(A)環状骨格を有し、1以上6以下のアルキレンオキサイド変性数を有する(メタ)アクリレートモノマーと、
(B1)環状骨格を有さず、2以上のアルキレングリコール構造を有する二官能(メタ)アクリレートモノマーと、
(B2)環状骨格を有さず、モノアルキレングリコール構造を有する二官能(メタ)クリレートモノマーと、
(C)光重合開始剤と、を含む。
(A)環状骨格を有し、1以上6以下のアルキレンオキサイド変性数を有する(メタ)アクリレートモノマーは、比較的高粘度であるものの、添加されることにより得られた被膜の繰り返しリフロー後のクラック耐性およびはんだ耐熱性を向上させるモノマーである。
(B1)環状骨格を有さず、2以上のアルキレングリコール構造を有する二官能(メタ)アクリレートモノマーは、硬化性組成物の粘度を低下させるために添加される希釈剤のうち、添加されることにより得られた被膜のリフロー時クラック耐性を向上させるものである。すなわち、この二官能(メタ)アクリレートモノマーは、(A)環状骨格を有し、1以上6以下のアルキレンオキサイド変性数を有する(メタ)アクリレートモノマーと、後述する(B2)環状骨格を有さず、モノアルキレングリコール構造を有する二官能(メタ)クリレートモノマーとの組み合わせにより、インクジェット法に使用可能な液性を維持しつつ、得られた被膜のリフロー時クラック耐性およびはんだ耐熱性を向上させる。
(B2)環状骨格を有さず、モノアルキレングリコール構造を有する二官能(メタ)アクリレートモノマーは、硬化性組成物の粘度を低下させるために添加される希釈剤のうち、添加されることにより得られた被膜のはんだ耐熱性を向上させるものである。すなわち、この二官能(メタ)アクリレートモノマーは、(A)環状骨格を有し、1以上6以下のアルキレンオキサイド変性数を有する(メタ)アクリレートモノマーと、上記(B1)環状骨格を有さず、2以上のアルキレングリコール構造を有する二官能(メタ)アクリレートモノマーとの組み合わせにより、インクジェット法に使用可能な液性を維持しつつ、得られた被膜のリフロー時クラック耐性およびはんだ耐熱性を向上させる。
光重合開始剤としては、エネルギー線の照射により、(メタ)アクリレートを重合させることが可能なものであれば、特に制限はなく、ラジカル重合開始剤が使用できる。
さらに、エチレン性不飽和基を有する多分岐状のオリゴマーまたはポリマーは官能基数または使用量を増加させても比較的低粘度であることから、硬化性得組成物を高硬度とするために有意である。
本発明の硬化性組成物の硬化物は、例えば、上記印刷直後の組成物層に50mJ/cm2〜1000mJ/cm2光照射を行うことにより組成物層を光硬化させることで得られる。光照射は、紫外線、電子線、化学線等の活性エネルギー線の照射により、好ましくは紫外線照射により行われる。
このように基板等の基材上にパターン印刷した硬化性組成物からなる被膜(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。
1.組成物の調製
表1に示す割合(単位:質量部)で各成分を配合し、これをディゾルバーで撹拌した。
その後ビーズミルを用いて1mmのジルコニアビーズにて分散を2時間行い、本発明の組成物(実施例1〜8)および比較組成物(比較例1および2)を得た。
BPE-4:EO変性ビスフェノールAジアクリレート(EO4モル付加物)、第一工業製薬株式会社製
HBPE-4:EO変性水添ビスフェノールAジアクリレート(EO4モル付加物)、第一工業製薬株式会社製
BPE-10:EO変性ビスフェノールAジアクリレート(EO10モル付加物)、第一工業製薬株式会社製
DPGDA:ジプロピレングリコールジアクリレート、東洋ケミカルズ株式会社製
A-NOD-N:1,9-ノナンジオールジアクリレート、新中村化学工業社製
HDDA:1,6−ヘキサンジオールジアクリレート、第一工業製薬株式会社製
Laromer LR8863:EO変性トリメチロールプロパントリアクリレート(EO6モル付加物)
Omnirad 379:2-(ジメチルアミノ)-2-[(4-メチルフェニル)メチル]-1-[4-(4-モルホリニル)フェニル]-1-ブタノン、IGM社 Resins製
ITX:2−イソプロピルチオキサントン、日本化薬社製
TPO: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サイド、IGM Resins社製
ビスコート#1000:デンドリマーポリエステルアクリレートオリゴマー(末端にアクリレート基を有する多分岐(デンドリマー型)ポリエステルアクリレートを主成分とするデンドリマー)、大阪有機化学工業社製
EA-1010LC:(メタ)アクリロイル基含有ビスフェノールA型エポキシ樹脂(単官能)、新中村化学工業社製
BI7982:3官能ブロックイソシアネート、Baxenden chemmical社製
4HBA:4−ヒドロキシブチルアクリレート、日本化成社製
メラミン:日産化学社製
フタロシアニンブルー:フタロシアニン系青色顔料、
クロモフタルエローAGR:アントラキノン系黄色顔料、
BYK-315N:シリコン系表面調整剤、ビックケミー・ジャパン社製
組成物粘度:ビーズミルでの分散直後の、JIS K2283に準拠して測定された50℃における粘度を下記基準により判定した。
○ 15mPa・s以上150mPa・s未満
× 150mPa・sを超過粘度
2−1.高温処理後のクラック耐性の評価
得られた各実施例および比較例の硬化性組成物を用いて以下の条件
基材:銅張積層板
研磨:バフ研磨(Scotch brite SF(#600相当)とUEF(#1000相当)の2連)
塗布:アプリケーター(ERICHSEN社製)、塗布時の膜厚30μm
仮硬化条件:300mJ/cm2、高圧水銀灯(ORC社製HMW−713)を光源として使用
熱硬化条件:150℃60分、加熱装置はDF610(ヤマト科学株式会社製)を使用
UV bump:1000mJ/cm2、高圧水銀灯(ORC社製HMW−713)を光源として使用
に従ってそれぞれ試験基板を作製した。
熱源設定温度:A.210℃、B.190℃、C.〜F.185℃、G.265℃、H.285℃、I.〜J.ファンによる冷却工程
「1.組成物の調製」で得られた各実施例および比較例の硬化性組成物を用い、
「2−1.高温処理後のクラック耐性の評価」の条件と同じ条件で各試験基板を作製した。
作製した各試験基板を用いてクロスカットテープピール試験(JIS K 5600)を実施した。表3に、試験後にも残存する塗膜の割合を百分率で示す。
作成した各試験基板の表面における鉛筆硬度をJIS K 5600−5−4に準拠して測定を行った。表3に、塗膜表面の鉛筆硬度を示す。
さらに、「2−1.高温処理後のクラック耐性の評価」において作製した各試験基板に対して、市販の無電解ニッケルめっきおよび無電解金めっき浴を用いて、ニッケル0.5μm、金0.03μmの条件で硬化被膜上にめっきを行った。
Claims (6)
- (A)環状骨格を有し、1以上6以下のアルキレンオキサイド変性数を有する(メタ)アクリレートモノマーと、
(B1)環状骨格を有さず、2以上のアルキレングリコール構造を有する二官能(メタ)アクリレートモノマーと、
(B2)環状骨格を有さず、モノアルキレングリコール構造を有する二官能(メタ)クリレートモノマーと、
(C)光重合開始剤と、
を含むインクジェット印刷用の硬化性組成物。 - 硬化性組成物の100質量部あたりの(A)環状骨格を有し、1以上6以下のアルキレンオキサイド変性数を有する(メタ)アクリレートモノマーの量が、5質量部以上40質量部以下である請求項1に記載のインクジェット印刷用の硬化性組成物。
- (B1)環状骨格を有さず、2以上のアルキレングリコール構造を有する二官能(メタ)アクリレートモノマーおよび(B2)環状骨格を有さず、モノアルキレングリコール構造を有する二官能(メタ)クリレートモノマーの総量に対する(A)環状骨格を有し、1以上6以下のアルキレンオキサイド変性数を有する(メタ)アクリレートモノマーの質量比が、0.10以上0.70以下である請求項1または2に記載のインクジェット印刷用の硬化性組成物。
- (B2)環状骨格を有さず、モノアルキレングリコール構造を有する二官能(メタ)クリレートモノマーに対する(B1)環状骨格を有さず、2以上のアルキレングリコール構造を有する二官能(メタ)アクリレートモノマーの質量比が1.0以上3.0以下である請求項1〜3の何れか一項に記載のインクジェット印刷用の硬化性組成物。
- 請求項1〜4の何れか一項に記載のインクジェット印刷用の硬化性組成物の硬化物。
- 請求項5に記載の硬化物を有する電子部品。
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