JP7489608B2 - 紫外線硬化性樹脂組成物、及び発光装置 - Google Patents
紫外線硬化性樹脂組成物、及び発光装置 Download PDFInfo
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- JP7489608B2 JP7489608B2 JP2019133150A JP2019133150A JP7489608B2 JP 7489608 B2 JP7489608 B2 JP 7489608B2 JP 2019133150 A JP2019133150 A JP 2019133150A JP 2019133150 A JP2019133150 A JP 2019133150A JP 7489608 B2 JP7489608 B2 JP 7489608B2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- MFTPIWFEXJRWQY-UHFFFAOYSA-N phosphoric acid prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OP(O)(O)=O MFTPIWFEXJRWQY-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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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Description
式(7)において、R1及びR2の各々は水素又はメチル基、nは1以上の整数、R3は炭素数1以上のアルキレン基であり、nが2以上の場合は一分子中の複数のR3は互いに同一であっても異なっていてもよい。
後掲の表1及び表2に示す成分を混合することで、実施例及び比較例の組成物を調製した。
・トリプロピレングリコールジアクリレート;2官能の化合物、式(7)においてn=3、
・ポリエチレングリコール200ジメタクリレート;2官能の化合物、式(7)においてn=4、
・ポリエチレングリコール200ジアクリレート;2官能の化合物、式(7)においてn=4、
・TPO;2,4,6-トリメチルベンゾイル-ジフェニル-フォスフィンオキサイド。アシルフォスフィンオキサイド系光重合開始剤、BASF株式会社製、品名IrgacureTPO。
・OXE01;式(5)に示す化合物。BASF株式会社製、品名IrgacureOXE01。
・OXE02;式(6)に示す化合物。BASF株式会社製、品名IrgacureOXE02。
・EPA;4-ジメチルアミノ安息香酸エチル。3級アミン系増感剤、日本化薬社製、品番カヤキュアーEPA。
(4-1)ゼオライト粒子1
ゼオライト粒子1は、下記の方法で製造され、そのD50は60nm、そのD90は110nm、pHは11である。
ゼオライト粒子2は、下記の方法で製造され、そのD50は150nm、そのD90は250nm、pHは11である。
・ソルスパース32000:ルーブリゾール株式会社製、品名SOLSPERSE32000、3級アミノ基を含有する界面活性剤。
2.1.ブリーチング性
硬化後のフィルムの厚みが10μmとなるようにして各実施例及び比較例の組成物を基板上に塗布して塗膜を作製した。そして、塗膜を波長395nmの紫外線により一旦露光させた(第1露光)。第1露光後、波長365nmでかつ露光量が1500mJ/cm2の紫外線により組成物をさらに露光させた(第2露光)。これにより、組成物の硬化物であるフィルムを得た。各実施例及び比較例のブリーチング性を、下記の項目に従って評価した。
A:第2露光後のフィルムの透過率(JIS K7361-1に準拠した全光線透過率)が95%以上である、
B:第2露光後のフィルムの透過率が90%以上95%未満である、
C:第2露光後のフィルムの透過率が90%未満である。
組成物の水分量を、カールフィッシャー水分測定装置(三菱アナリテック社製、型番CA-200)及び水分気化装置(三菱アナリテック社製、型番VA-200)を用いて測定した。
ガラス製の基板上に厚み100nmのITO電極を作製した。このITO電極上に、真空蒸着法で、厚み60nmのα-NPDの層、厚み60nmのAlq3の層、厚み0.5nmのフッ化リチウムの層、厚み10nmのMgAgの層、及び厚み100nmのIZO(酸化インジウム亜鉛)の層を順次作製した。これにより、基板上に、平面視寸法10mm×10mmの有機EL素子を作製した。次に、基板上に、有機EL素子を覆う平面視寸法13mm×13mm、厚み約250nmの窒化ケイ素の層を、プラズマCVD法にて作製した。この窒化ケイ素の層上に組成物を、インクジェットプリンター(マイクロジェット社製、「NanoPrinter300」)にて塗布した。続いて、酸素を含む雰囲気(酸素濃度210L/m3)で、かつ約30mW/cm2の条件の下、組成物をピーク波長が395nmの光で15秒間露光させた。その後、同条件の下、組成物をピーク波長が365nmの光で15秒間更に露光させることで、組成物を硬化させて封止材を作製した。封止材の作製後、さらに、基板上に、有機EL素子を覆う平面視寸法12mm×12mm、厚み約250nmの窒化ケイ素の層(パッシベーション層)を、プラズマCVD法にて作製した。これにより、有機EL発光装置を得た。
上記2.3.の試験のために作製した有機EL発光装置を、85℃、85%RHの条件下に100時間暴露した後、有機EL素子に3Vの電圧を印加して有機EL素子を発光させた。このときの有機EL素子の発光状態(ダークスポット及び有機EL素子周辺消光の有無)を目視で観察した。
インクジェットプリンターとしてリコー社製型番MH2420を用い、組成物をインクジェットプリンターのカートリッジに入れ、インクジェットプリンターにおけるノズルからカートリッジ内の組成物を吐出しうることを確認してから、ノズルから組成物を吐出させてテストパターンを連続で印刷した。その結果、組成物を1時間吐出できるとともに吐出動作が安定していた場合を「A」、組成物を1時間吐出できたが吐出動作が断続的に不安定になった場合を「B」、吐出開始から1時間経過前にノズルが詰まって組成物を吐出できなくなった場合を「C」と、評価した。
各実施例及び比較例の組成物を平滑な台の上に塗布してから、これにシーシーエス株式会社製のLED-UV照射器を用いて、ピーク波長365nm、出力100mW/cm2の条件で光を15秒間照射することで光硬化させた。光を照射する際、酸素を含む雰囲気(酸素濃度210L/m3)とした。これにより、厚み10μmのフィルムを作製した。試験者が、このフィルムの表面に指で触れて、タック性を評価した。その結果、試験者がタックを感じない場合を「A」、タックをやや感じた場合を「B」、タックを強く感じた場合を「C」と、評価した。
ピーク波長を395nmにした以外は、上記2.6.と同様にしてタック性を評価した。
各実施例及び比較例の組成物を塗布して塗膜を作製し、この塗膜を、シーシーエス株式会社製のLED-UV照射器を用いて、ピーク波長395nm、約100mW/cm2の条件で15秒間光を照射して光硬化させることで、厚み10μmのフィルムを作製した。光を照射する際の雰囲気は、上記2.6.の場合と同様である。このフィルムの、JIS K7361-1による全光線透過率を測定した。
組成物の硬化物を加熱した場合のアウトガスをヘッドスペース法でサンプリングしてガスクロマトグラフにより測定した。ヘッドスペース用バイアルに組成物を100mg入れ、組成物に、シーシーエス株式会社製のLED-UV照射器を用いて、ピーク波長395nm、約100mW/cm2の条件で光照射して組成物を硬化させた後、バイアルを封止し、80℃で30分間加熱してから、バイアル中の気相部分をガスクロマトグラフに導入して分析した。その結果、発生したガスが300ppm以下であった場合を「A」、300ppmを超え500ppm未満であった場合を「B」、500ppm以上であった場合を「C」と評価した。
Claims (9)
- アクリル化合物(A)と、
光重合開始剤(B)と、を含有し、
溶剤を含有せず、又は前記溶剤を含有し、かつ前記溶剤の含有量が1質量%以下であり、
前記光重合開始剤(B)は、オキシムエステル系光重合開始剤(B1)と、前記オキシムエステル系光重合開始剤(B1)以外の化合物(B11)とを含有し、
前記化合物(B11)は、アシルホスフィンオキサイド系開始剤を含有し、
紫外線硬化性樹脂組成物の固形分量に対する、前記化合物(B11)の量は、0.5質量%以上5質量%以下であり、
前記オキシムエステル系光重合開始剤(B1)の割合は、前記アクリル化合物(A)に対して、0.5質量%以上10質量%以下であり、
25℃での粘度は、1mPa・s以上35mPa・s以下であり、
光源が発する光を透過させる光学部品を作製するための、
紫外線硬化性樹脂組成物。 - 前記アクリル化合物(A)は、ポリアルキレングリコールジ(メタ)アクリレートを含有する、
請求項1に記載の紫外線硬化性樹脂組成物。 - 前記ポリアルキレングリコールジ(メタ)アクリレートの割合は、前記アクリル化合物(A)に対して、40質量%以上80質量%以下である、
請求項2に記載の紫外線硬化性樹脂組成物。 - 前記アクリル化合物(A)は、ペンタエリスリトールテトラ(メタ)アクリレートを含有する、
請求項1~3のいずれか1項に記載の紫外線硬化性樹脂組成物。 - 前記ペンタエリスリトールテトラ(メタ)アクリレートの割合は、前記アクリル化合物(A)に対して、0.5質量%以上10質量%以下である、
請求項4に記載の紫外線硬化性樹脂組成物。 - 前記アクリル化合物(A)は、モルホリン骨格を有する化合物を含有する、
請求項1~5のいずれか1項に記載の紫外線硬化性樹脂組成物。 - 前記モルホリン骨格を有する化合物の割合は、前記アクリル化合物(A)に対して、5質量%以上50質量%以下である、
請求項6に記載の紫外線硬化性樹脂組成物。 - 光源と、前記光源が発する光を透過させる光学部品とを備える発光装置を製造する方法であり、
請求項1~7のいずれか1項に記載の紫外線硬化性樹脂組成物をインクジェット法で成形して塗膜を作製し、
前記塗膜に紫外線を照射することで前記光学部品を作製することを含む、
発光装置の製造方法。 - 光源と、
前記光源が発する光を透過させる光学部品とを備え、
前記光学部品は、請求項1~7のいずれか1項に記載の紫外線硬化性樹脂組成物の硬化物からなる、
発光装置。
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JP2016204585A (ja) | 2015-04-28 | 2016-12-08 | 富士フイルム株式会社 | 硬化性組成物、硬化膜、有機el表示装置、液晶表示装置、タッチパネル及びタッチパネル表示装置 |
WO2019189185A1 (ja) | 2018-03-30 | 2019-10-03 | 太陽インキ製造株式会社 | インクジェット用硬化性組成物、その硬化物、及びその硬化物を有する電子部品 |
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