JP6094579B2 - 膜形成用組成物及び埋め込み材料 - Google Patents
膜形成用組成物及び埋め込み材料 Download PDFInfo
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- JP6094579B2 JP6094579B2 JP2014514758A JP2014514758A JP6094579B2 JP 6094579 B2 JP6094579 B2 JP 6094579B2 JP 2014514758 A JP2014514758 A JP 2014514758A JP 2014514758 A JP2014514758 A JP 2014514758A JP 6094579 B2 JP6094579 B2 JP 6094579B2
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- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- HUGHWHMUUQNACD-UHFFFAOYSA-N prop-2-enoxymethylbenzene Chemical compound C=CCOCC1=CC=CC=C1 HUGHWHMUUQNACD-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
- 150000003217 pyrazoles Chemical class 0.000 description 1
- MFUFBSLEAGDECJ-UHFFFAOYSA-N pyren-2-ylamine Natural products C1=CC=C2C=CC3=CC(N)=CC4=CC=C1C2=C43 MFUFBSLEAGDECJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- TVBIVRGNYNBFCD-UHFFFAOYSA-N triethylazanium;trifluoromethanesulfonate Chemical compound CC[NH+](CC)CC.[O-]S(=O)(=O)C(F)(F)F TVBIVRGNYNBFCD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 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
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- JODJRDDQVZMRIY-UHFFFAOYSA-N trityloxyboronic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OB(O)O)C1=CC=CC=C1 JODJRDDQVZMRIY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
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- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
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Description
更に、シロキサンポリマーの一部に高屈折率な縮合環状骨格を導入する手法も報告されている(特許文献2)。
これまで炭素及び窒素からなる耐熱性有機材料としては、芳香族ポリイミドや芳香族ポリアミドが主として用いられているが、これらの材料は直鎖構造を有しているため耐熱温度はそれほど高くない。
また、耐熱性を有する含窒素高分子材料として、トリアジン系縮合材料も報告されている(特許文献4)。
求められる具体的な特性としては、1)耐熱性、2)透明性、3)高屈折率、4)高溶解性、5)低体積収縮率等が挙げられる。
請求項1:
下記式(1)で表される繰り返し単位構造を含むトリアジン環含有重合体、架橋剤及びリニアポリマーを与え得る有機モノマーを含み、
前記有機モノマーが、式(A)で示される化合物であることを特徴とする膜形成用組成物。
請求項2:
前記式(A)におけるR102及びR103がともに水素原子であり、R104が重合性炭素−炭素二重結合含有基である請求項1記載の膜形成用組成物。
請求項3:
前記有機モノマーが、N−ビニルホルムアミドである請求項1又は2記載の膜形成用組成物。
請求項4:
更に溶剤を含む請求項1、2又は3記載の膜形成用組成物。
請求項5:
溶剤を含まない請求項1、2又は3記載の膜形成用組成物。
請求項6:
前記架橋剤が、多官能エポキシ化合物及び/又は多官能(メタ)アクリル化合物である請求項1〜4のいずれか1項記載の膜形成用組成物。
請求項7:
前記架橋剤が、多官能(メタ)アクリル化合物である請求項6記載の膜形成用組成物。
請求項8:
前記多官能(メタ)アクリル化合物が、25℃で液体であり、かつ、その粘度が5,000mPa・s以下の化合物である請求項6又は7記載の膜形成用組成物。
請求項9:
前記架橋剤が、多官能エポキシ化合物、多官能ビニルエーテル化合物又は多官能アリルエーテル化合物である請求項1、2、3又は5記載の膜形成用組成物。
請求項10:
前記架橋剤が、多官能アリルエーテル化合物である請求項9記載の膜形成用組成物。
請求項11:
請求項1〜4及び6〜8のいずれか1項記載の膜形成用組成物からなる埋め込み材料。
請求項12:
請求項11記載の埋め込み材料から得られる埋め込み膜。
請求項13:
請求項12記載の埋め込み膜を備える電子デバイス。
請求項14:
請求項1〜10のいずれか1項記載の膜形成用組成物を硬化させて得られる硬化膜。
請求項15:
請求項14記載の硬化膜を備える電子デバイス。
請求項16:
請求項1〜3、5、9及び10のいずれか1項記載の膜形成用組成物を硬化させて得られる硬化膜を備えるトップエミッション型有機エレクトロルミネッセンス素子。
本発明の組成物から得られた硬化膜は、液晶ディスプレイ、有機ELディスプレイ、LED素子、固体撮像素子、有機薄膜太陽電池、色素増感太陽電池、有機TFT等の電子デバイスを作製する際の一部材として好適に利用できる。
特に、本発明の硬化膜はクラックが発生しにくい膜であるため、有機エレクトロルミネッセンス(EL)素子の光取り出し層に適用できる埋め込み材料として好適に利用できる。更に、無溶剤型膜形成用組成物は有機EL膜等の有機膜を劣化させることがないため、これから得られる硬化膜はトップエミッション型有機EL素子の光取り出し層として好適に利用できる。
また、固体撮像素子の部材である、フォトダイオード上の埋め込み膜及び平坦化膜、カラーフィルター前後の平坦化膜、マイクロレンズ、マイクロレンズ上の平坦化膜及びコンフォーマル膜等として好適に利用できる。
なお、アルキル基、アルコキシ基としては前記と同様のものが挙げられる。
なお、本発明における重量平均分子量は、ゲルパーミエーションクロマトグラフィー(以下、GPCという)分析による標準ポリスチレン換算で得られる平均分子量である。
例えば、下記スキーム1に示されるように、繰り返し構造(17’)を有する高分岐重合体は、ハロゲン化シアヌル(18)及びm−フェニレンジアミン化合物(19)を適当な有機溶剤中で反応させて得ることができる。
中でも、N,N−ジメチルホルムアミド、ジメチルスルホキシド、N−メチル−2−ピロリドン、N,N−ジメチルアセトアミド、及びこれらの混合溶剤が好ましく、特に、N,N−ジメチルアセトアミド、N−メチル−2−ピロリドンが好適である。
また、添加は、滴下等によって徐々に加えても、全量一括して加えてもよい。
いずれのスキームの方法においても、反応終了後、生成物は再沈法等によって容易に精製できる。
これらの中でも、アルキルアミノ、アルコキシシリル基含有アルキルアミノ、アラルキルアミノ、アリールアミノ基が好ましく、アルキルアミノ、アリールアミノ基がより好ましく、アリールアミノ基が更に好ましい。
エステル基の具体例としては、メトキシカルボニル、エトキシカルボニル基等が挙げられる。
この手法によって得られた高分岐重合体は、溶剤への溶解性(凝集抑制)や、架橋剤との架橋性に優れたものとなるため、後述する架橋剤と組み合わせた組成物として用いる場合に特に有利である。
また、このような有機モノアミンの存在下で、ハロゲン化シアヌル化合物とジアミノアリール化合物とを反応させる反応は、前記と同様の有機溶剤を用いて行ってもよい。
本発明の膜形成用組成物に用いられる架橋剤としては、本発明の重合体と反応し得る置換基を有する化合物であれば特に限定されるものではない。
このような骨格を有する多官能(メタ)アクリル化合物としては、例えば、NKエステルA−9300、同A−9300−1CL(いずれも、新中村化学工業(株)製)が挙げられる。
このような低粘度架橋剤も市販品として入手可能であり、例えば、上述した多官能(メタ)アクリル化合物のうち、NKエステルA−GLY−3E(85mPa・s,25℃)、同A−GLY−9E(95mPa・s,25℃)、同A−GLY−20E(200mPa・s,25℃)、同A−TMPT−3EO(60mPa・s,25℃)、同A−TMPT−9EO、同ATM−4E(150mPa・s,25℃)、同ATM−35E(350mPa・s,25℃)(以上、新中村化学工業(株)製)等の、(メタ)アクリル基間の鎖長が比較的長い架橋剤が挙げられる。
また、光塩基発生剤は市販品を用いてもよく、その具体例としては、TPS−OH、NBC−101、ANC−101(いずれも製品名、みどり化学(株)製)等が挙げられる。
光ラジカル重合開始剤としても、公知のものから適宜選択して用いればよく、例えば、アセトフェノン類、ベンゾフェノン類、ミヒラーのベンゾイルベンゾエート、アミロキシムエステル、テトラメチルチウラムモノサルファイド及びチオキサントン類等が挙げられる。
特に、光開裂型の光ラジカル重合開始剤が好ましい。光開裂型の光ラジカル重合開始剤については、最新UV硬化技術(159頁、発行人:高薄一弘、発行所:(株)技術情報協会、1991年発行)に記載されている。
市販の光ラジカル重合開始剤としては、例えば、BASF社製 商品名:イルガキュア 184、369、651、500、819、907、784、2959、CGI1700、CGI1750、CGI1850、CG24−61、ダロキュア 1116、1173、BASF社製 商品名:ルシリン TPO、UCB社製 商品名:ユベクリル P36、フラテツリ・ランベルティ社製 商品名:エザキュアー KIP150、KIP65LT、KIP100F、KT37、KT55、KTO46、KIP75/B等が挙げられる。
光ラジカル重合開始剤を用いる場合、多官能(メタ)アクリレート化合物100質量部に対して、0.1〜15質量部の範囲で使用することが好ましく、より好ましくは1〜10質量部の範囲である。
中でもR102としては、水素原子又はメチル基が好ましく、R103としては、トリアジン環含有重合体との水素結合形成能を確保するという点から、水素原子が好ましい。
これらのうち、好ましくは、炭素数1〜5のアルキル基である。
本発明の膜形成用組成物には各種の溶剤を添加し、トリアジン環含有重合体を溶解させて使用することができる。この場合、溶剤は重合時に用いた溶媒と同じものでも別のものでもよい。この溶剤は、重合体との相溶性を損なわなければ特に限定されず、1種でも複数種でも任意に選択して用いることができる。
本発明の膜形成用組成物組成物は、溶剤を含まない無溶剤型とすることもできる。この場合、上述のとおり、式(A)で表されるリニアポリマーを与え得る有機モノマーが反応性希釈剤として機能する。
本発明の膜形成用組成物は、本発明の効果を損なわない限りにおいて、トリアジン環含有重合体、架橋剤、リニアポリマーを与え得る有機モノマー以外のその他の成分、例えば、レベリング剤、界面活性剤等を含んでもよい。
なお、前記その他の成分は、本発明の組成物を調製する際の任意の工程で添加することができる。
本発明の膜形成用組成物を用いて硬化膜を形成する場合、その下地層は特に限定されない。例えば、有機EL膜等の有機膜又は基材に本発明の組成物を塗布し、その後必要に応じて加熱して溶剤を蒸発させた後、加熱又は光照射して所望の硬化膜を形成することができる。
[1H−NMR]
装置:Varian NMR System 400NB(400MHz)
JEOL−ECA700(700MHz)
測定溶剤:DMSO−d6
基準物質:テトラメチルシラン(TMS)(δ0.0ppm)
[GPC]
装置:東ソー(株)製 HLC−8200 GPC
カラム:Shodex KF−804L+KF−805L
カラム温度:40℃
溶剤:テトラヒドロフラン(以下、THF)
検出器:UV(254nm)
検量線:標準ポリスチレン
[エリプソメーター]
装置:ジェー・エー・ウーラム・ジャパン製 多入射角分光エリプソメーターVASE
[示差熱天秤(TG−DTA)]
装置:(株)リガク製 TG−8120
昇温速度:10℃/分
測定温度:25℃−750℃
合成例1で得られたHB−TmDA40について、TG−DTA測定を行ったところ、5%重量減少は419℃であった。その結果を図2に示す。
(2)屈折率測定
合成例1で得られたHB−TmDA40 0.5gを、シクロヘキサノン4.5gに溶解し、薄黄色透明溶液を得た。得られたポリマーワニスをガラス基板上にスピンコーターを用いて200rpmで5秒間、2,000rpmで30秒間スピンコートし、150℃で1分、250℃で5分間加熱して溶剤を除去し、被膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は1.790であった。
合成例1で得られたHB−TmDA40 100gをシクロヘキサノン57.6g、プロピレングリコールモノメチルエーテル230.4g、イオン交換水12gの混合溶媒に溶解させ、25質量%の溶液を調製した(以下、HB−TmDA40V1という)。
合成例1で得られたHB−TmDA40 100gをシクロヘキサノン288.0g、イオン交換水12gの混合溶媒に溶解させ、25質量%の溶液を調製した(以下、HB−TmDA40V2という)。
合成例1で得られたHB−TmDA40の20質量%シクロヘキサノン/イオン交換水溶液(96/4=wt/wt)を予め用意し、その溶液5.0g、ATM−35E(新中村化学工業(株)製)0.03g、A−GLY−20E(新中村化学工業(株)製)0.1g、光ラジカル開始剤イルガキュア184(BASF社製)0.05g、メガファックF−554(DIC(株)製)0.0005g、及びシクロヘキサノン2.23gを加え、目視で溶解したことを確認して総固形分濃度15質量%のワニス(以下、HB−TmDA40VF15という)を調製した。
合成例1で得られたHB−TmDA40 100gをシクロヘキサノン384.0g、イオン交換水16gの混合溶媒に溶解させ、20質量%の溶液を調製した(以下、HB−TmDA40V3という)。
製造例1で調製したHB−TmDA40V1 4g、60質量%シクロヘキサノン溶液のエトキシ化グリセリントリアクリレート(A−GLY−20E、200mPa・s、新中村化学工業(株)製)0.17g、60質量%シクロヘキサノン溶液のエトキシ化ペンタエリスリトールテトラアクリレート(ATM−35E、350mPa・s、新中村化学工業(株)製)0.05g、60質量%シクロヘキサノン溶液のN−ビニルホルムアミド1.17g、20質量%シクロヘキサノン溶液の光ラジカル開始剤イルガキュア184(BASF社製)0.4g、1質量%シクロヘキサノン溶液の界面活性剤メガファックR−30−N(DIC(株)製)0.05g、及びシクロヘキサノン/PGME/イオン交換水(19/77/4=wt/wt/wt)0.14gを加え、目視で溶解したことを確認して総固形分濃度32質量%のワニス(以下、HB−TmDA40VF1という)を調製した。
実施例1で調製したHB−TmDA40VF1を用い、下記手法により埋め込み性試験を行った。埋め込み性試験に用いた構造物基板は材質がシリコンであり、深さが1.6μm、Via径が400nmである。
HB−TmDA40VF1を構造物基板に5μm狙いでスピンコート法にて製膜し、ホットプレートを用いて130℃で5分間の焼成を行った。その後、低圧水銀ランプにより、積算露光量400mJ/cm2で硬化させ硬化膜を得た。
製膜された構造物基板は、ダイアモンドペンを用いて基板の端に傷をつけた後、基板をヘキ開し、SEM観察を行った。観察した画像を図3に示す。
図3に示されるように、HB−TmDA40VF1はViaのボトムにまで材料が到達しており、上部の膜厚が3μmほどあることから、平坦性を保持できる埋め込み材料として使用できる可能性が示唆された。
実施例1で調製したHB−TmDA40VF1を用い、深さが3.0μm、Via径が15μmのシリコン製構造基板を用いた以外は、実施例2と同様にして埋め込み性試験を行った。
製膜された構造物基板は、ダイアモンドペンを用いて基板の端に傷をつけた後、基板をヘキ開し、SEM観察を行った。観察した画像を図4に示す。
実施例1で調製したHB−TmDA40VF1を用い、下記手法により埋め込み性試験を行った。埋め込み性試験に用いた構造物基板は材質がシリコンであり、深さが3.0μm、Via径が15μmである。
HB−TmDA40VF1を構造物基板に5μm狙いでスピンコート法にて製膜し、ホットプレートを用いて130℃で5分間の焼成を行った。さらにその上から、平坦性を得る目的で、製造例3で調製したHB−TmDA40VF15を1μm狙いでスピンコート法にて製膜し、ホットプレートを用いて130℃で3分間の焼成を行った。
その後、低圧水銀ランプにより、積算露光量400mJ/cm2で硬化させ硬化膜を得た。
製膜された構造物基板は、ダイアモンドペンを用いて基板の端に傷をつけた後、基板をヘキ開し、SEM観察を行った。観察した画像を図5に示す。
実施例1で調製したHB−TmDA40VF1を用い、下記手法により埋め込み性試験を行った。埋め込み性試験に用いた構造物基板は材質がシリコンであり、深さが3.0μm、Via径が15μmである。
HB−TmDA40VF1を構造物基板に5μm狙いでスピンコート法にて製膜し、ホットプレートを用いて130℃で5分間の焼成を行った。得られた乾燥膜上に、同ワニスを同条件にて製膜し、さらにその上から、平坦性を得る目的で、製造例3で調製したHB−TmDA40VF15を1μm狙いでスピンコート法にて製膜し、ホットプレートを用いて130℃で3分間の焼成を行った。
その後、低圧水銀ランプにより、積算露光量400mJ/cm2で硬化させ硬化膜を得た。
製膜された構造物基板は、ダイアモンドペンを用いて基板の端に傷をつけた後、基板をヘキ開し、SEM観察を行った。観察した画像を図6に示す。
製造例2で調製したHB−TmDA40V2 10g、エトキシ化グリセリントリアクリレート(A−GLY−20E、200mPa・s、新中村化学工業(株)製)0.20g、エトキシ化ペンタエリスリトールテトラアクリレート(ATM−35E、350mPa・s、新中村化学工業(株)製)0.06g、光ラジカル開始剤イルガキュア184(BASF社製)0.10g、1質量%シクロヘキサノン溶液の界面活性剤メガファックF‐554(DIC(株)製)0.10g、及び濃度調整のためのシクロヘキサノン/イオン交換水(96/4=wt/wt)0.27gを加え、目視で溶解したことを確認して総固形分濃度22質量%のワニス(以下、HB−TmDA40VF2という)を調製した。
比較例1で調製したHB−TmDA40VF2を用い、実施例3と同様にして埋め込み性試験を行った。
製膜された構造物基板は、ダイアモンドペンを用いて基板の端に傷をつけた後、基板をヘキ開し、SEM観察を行った。観察した画像を図7に示す。
製造例4で調製したHB−TmDA40V3 5.0g、エトキシ化グリセリントリアクリレート(A−GLY−20E、200mPa・s、新中村化学工業(株)製)0.1g、エトキシ化ペンタエリスリトールテトラアクリレート(ATM−35E、350mPa・s、新中村化学工業(株)製)0.03g、光ラジカル開始剤イルガキュア184(BASF社製)0.05g、5質量%シクロヘキサノン溶液の界面活性剤メガファックF−554(DIC(株)製)0.01g、N−ビニルホルムアミド(東京化成工業(株)製)0.25g、及び濃度調整のためのシクロヘキサノン/イオン交換水(96/4=wt/wt)2.43gを加え、目視で溶解したことを確認して総固形分濃度15質量%(NVFを固形分に加えると総固形分濃度18質量%)のワニス(以下、HB−TmDA40VF3という)を調製した。
N−ビニルホルムアミド(東京化成工業(株)製)を0.50g、濃度調整のためのシクロヘキサノン/イオン交換水(96/4=wt/wt)を2.18gとした以外は、実施例6と同様にして総固形分濃度15質量%(NVFを固形分に加えると総固形分濃度21質量%)のワニス(以下、HB−TmDA40VF4という)を調製した。
続いて、得られたHB−TmDA40VF4を用いた以外は、実施例6と同様にして硬化膜を作製し、屈折率を測定したところ、550nmにおける屈折率は1.7649であった。
N−ビニルホルムアミド(東京化成工業(株)製)を0.75g、濃度調整のためのシクロヘキサノン/イオン交換水(96/4=wt/wt)を1.93gとした以外は、実施例6と同様にして総固形分濃度15質量%(NVFを固形分に加えると総固形分濃度25質量%)のワニス(以下、HB−TmDA40VF5という)を調製した。
続いて、得られたHB−TmDA40VF5を用いた以外は、実施例6と同様にして硬化膜を作製し、屈折率を測定したところ、550nmにおける屈折率は1.7463であった。
N−ビニルホルムアミド(東京化成工業(株)製)を1.00g、濃度調整のためのシクロヘキサノン/イオン交換水(96/4=wt/wt)を1.68gとした以外は、実施例6と同様にして総固形分濃度15質量%(NVFを固形分に加えると総固形分濃度28質量%)のワニス(以下、HB−TmDA40VF6という)を調製した。
続いて、得られたHB−TmDA40VF6を用いた以外は、実施例6と同様にして硬化膜を作製し、屈折率を測定したところ、550nmにおける屈折率は1.7452であった。
N−ビニルホルムアミド(東京化成工業(株)製)を1.50g、濃度調整のためのシクロヘキサノン/イオン交換水(96/4=wt/wt)を1.18gとした以外は、実施例6と同様にして総固形分濃度15質量%(NVFを固形分に加えると総固形分濃度34質量%)のワニス(以下、HB−TmDA40VF7という)を調製した。
続いて、得られたHB−TmDA40VF7を用いた以外は、実施例6と同様にして硬化膜を作製し、屈折率を測定したところ、550nmにおける屈折率は1.7441であった。
合成例1で得られたHB−TmDA40 100gをN−ビニルホルムアミド300.0gに溶解させ、25質量%の溶液を調製した。
製造例5で調製した溶液3.0g、ペンタエリスリトールトリアリルエーテル(ダイソー(株)製、ネオアリルP−30M)0.3g、BYK−307(ビックケミー・ジャパン(株)製)の5質量%N−ビニルホルムアミド溶液0.075g、CXC−1802(KING INDUSTRY社製)0.0375g及びN−ビニルホルムアミド0.839gを加え、目視で溶解したことを確認して総固形分100質量%のワニス(以下、HB−TmDA40VF8という)を調製した。
製造例5で調製した溶液3.0g、ペンタエリスリトールトリアリルエーテル(ダイソー(株)製、ネオアリルP−30M)0.375g、BYK−307(ビックケミー・ジャパン(株)製)の5質量%N−ビニルホルムアミド溶液0.075g、CXC−1802(KING INDUSTRY社製)0.0375g及びN−ビニルホルムアミド0.763gを加え、目視で溶解したことを確認して総固形分100質量%のワニス(以下、HB−TmDA40VF9という)を調製した。
製造例5で調製した溶液3.0g、ペンタエリスリトールトリアリルエーテル(ダイソー(株)製、ネオアリルP−30M)0.45g、BYK−307(ビックケミー・ジャパン(株)製)の5質量%N−ビニルホルムアミド溶液0.075g、CXC−1802(KING INDUSTRY社製)0.0375g及びN−ビニルホルムアミド0.687gを加え、目視で溶解したことを確認して総固形分100質量%のワニス(以下、HB−TmDA40VF10という)を調製した。
実施例11で調製したHB−TmDA40VF8をソーダライムガラス基板上にスピンコーターを用いて200rpmで5秒間、2,000rpmで30秒間スピンコートし、ホットプレートを用いて100℃で10分間の焼成を行った。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は1.699であった。
実施例12で調製したHB−TmDA40VF9を用いた以外は、実施例5と同様にして硬化膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は1.702であった。
実施例13で調製したHB−TmDA40VF10を用いた以外は、実施例5と同様にして硬化膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は1.719であった。
Claims (16)
- 下記式(1)で表される繰り返し単位構造を含むトリアジン環含有重合体、架橋剤及びリニアポリマーを与え得る有機モノマーを含み、
前記有機モノマーが、式(A)で示される化合物であることを特徴とする膜形成用組成物。
- 前記式(A)におけるR102及びR103がともに水素原子であり、R104が重合性炭素−炭素二重結合含有基である請求項1記載の膜形成用組成物。
- 前記有機モノマーが、N−ビニルホルムアミドである請求項1又は2記載の膜形成用組成物。
- 更に溶剤を含む請求項1、2又は3記載の膜形成用組成物。
- 溶剤を含まない請求項1、2又は3記載の膜形成用組成物。
- 前記架橋剤が、多官能エポキシ化合物及び/又は多官能(メタ)アクリル化合物である請求項1〜4のいずれか1項記載の膜形成用組成物。
- 前記架橋剤が、多官能(メタ)アクリル化合物である請求項6記載の膜形成用組成物。
- 前記多官能(メタ)アクリル化合物が、25℃で液体であり、かつ、その粘度が5,000mPa・s以下の化合物である請求項6又は7記載の膜形成用組成物。
- 前記架橋剤が、多官能エポキシ化合物、多官能ビニルエーテル化合物又は多官能アリルエーテル化合物である請求項1、2、3又は5記載の膜形成用組成物。
- 前記架橋剤が、多官能アリルエーテル化合物である請求項9記載の膜形成用組成物。
- 請求項1〜4及び6〜8のいずれか1項記載の膜形成用組成物からなる埋め込み材料。
- 請求項11記載の埋め込み材料から得られる埋め込み膜。
- 請求項12記載の埋め込み膜を備える電子デバイス。
- 請求項1〜10のいずれか1項記載の膜形成用組成物を硬化させて得られる硬化膜。
- 請求項14記載の硬化膜を備える電子デバイス。
- 請求項1〜3、5、9及び10のいずれか1項記載の膜形成用組成物を硬化させて得られる硬化膜を備えるトップエミッション型有機エレクトロルミネッセンス素子。
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