JP2023519314A - 化合物、それを含む反射防止フィルムおよびディスプレイ装置 - Google Patents
化合物、それを含む反射防止フィルムおよびディスプレイ装置 Download PDFInfo
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 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
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 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
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
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Abstract
Description
Mは2個の水素原子、2価の金属原子、3価の置換金属原子、4価の置換金属原子、水酸化金属原子または酸化金属原子であり、
R1~R16はそれぞれ独立して、水素、置換若しくは非置換されたC1~C20アルキル基、置換若しくは非置換されたC3~C20シクロアルキル基、置換若しくは非置換されたC6~C20アリール基、置換若しくは非置換されたC2~C20ヘテロアリール基、下記化学式2で表されるスルホニルアミド基、またはこれらの組み合わせであり、
R1~R8の少なくとも一つおよびR9~R16の少なくとも一つは下記化学式2で表されるスルホニルアミド基である。
R17およびR18はそれぞれ独立して水素、置換若しくは非置換されたC1~C20アルキル基、置換若しくは非置換されたC3~C20シクロアルキル基、置換若しくは非置換されたC6~C20アリール基、または置換若しくは非置換されたC2~C20ヘテロアリール基であり、
R17およびR18の少なくとも一つはC3~C20シクロアルキル基であり、
*は前記化学式1のベンゼン環に結合する部分を意味する。
MはCu、Co、Zn、V(=O)またはAgであり、
n1~n4はそれぞれ独立して0または1の整数であり、
n5は1~4の整数であり、
ただし、n1+n2+n3+n4≠0である。
以下、本発明の実施形態を詳細に説明する。ただし、これは例示として提示されるものであり、本発明はこれによって制限されず、本発明は後述する特許請求の範囲の範疇によってのみ定義される。
MはZn、CoまたはCuであり、
R1~R16はそれぞれ独立して、水素、置換若しくは非置換されたC1~C20アルキル基、置換若しくは非置換されたC3~C20シクロアルキル基、置換若しくは非置換されたC6~C20アリール基、置換若しくは非置換されたC2~C20ヘテロアリール基、下記化学式2で表されるスルホニルアミド基、またはこれらの組み合わせであり、
R1~R8の少なくとも一つおよびR9~R16の少なくとも一つは下記化学式2で表されるスルホニルアミド基であり、
R17およびR18はそれぞれ独立して水素、置換若しくは非置換されたC1~C20アルキル基、置換若しくは非置換されたC3~C20シクロアルキル基、置換若しくは非置換されたC6~C20アリール基、または置換若しくは非置換されたC2~C20ヘテロアリール基であり、R17およびR18の少なくとも一つはC3~C20シクロアルキル基であり、*は前記化学式1のベンゼン環に結合する部分を意味する。
MはCu、Co、Zn、V(=O)またはAgであり、
n1~n4はそれぞれ独立して0または1の整数であり、
n5は1~4の整数であり、
ただし、n1+n2+n3+n4≠0である。
前記反射防止層は低屈折層のみからなるか低屈折層を含むことができる。
L7およびL8はそれぞれ独立して単結合、置換若しくは非置換されたC1~C20アルキレン基、置換若しくは非置換されたC3~C20シクロアルキレン基、置換若しくは非置換されたC6~C20アリーレン基または置換若しくは非置換されたC2~C20ヘテロアリーレン基である。
L7およびL8はそれぞれ独立して単結合、置換若しくは非置換されたC1~C20アルキレン基、置換若しくは非置換されたC3~C20シクロアルキレン基、置換若しくは非置換されたC6~C20アリーレン基または置換若しくは非置換されたC2~C20ヘテロアリーレン基であり、
u1およびu2はそれぞれ独立して0または1の整数である。
前記硬化性組成物はインクジェット噴射方式で0.5~10μmの厚さで基板の上に塗布することが好ましい。前記インクジェット噴射は単一カラーのみ噴射して必要な色の数に応じて繰り返し噴射することでパターンを形成することができ、工程を減らすために必要な色の数を同時に噴射する方式でパターンを形成することもできる。
前記収得したパターンを硬化させて硬化樹脂膜を得ることができる。この時、硬化させる方法としては熱硬化工程が好ましい。前記熱硬化工程は約100℃以上の温度で約3分間加熱して硬化性組成物内の溶媒を先に除去した後、引き続き160℃~300℃の温度で加熱して硬化させる工程であり得、より好ましくは180℃~250℃の温度で約30分間加熱して硬化させる工程であり得る。
以下、本発明の好ましい実施例を記載する。ただし、下記の実施例は本発明の好ましい一実施例だけであり、本発明は下記実施例によって限定されるものではない。
合成例1:化学式10で表される化合物の合成
(1)500ml丸底フラスコでchlorosulfonic acid(35g)を入れて攪拌して30℃未満に冷却する。CuPC(Copper(II) phthalocyanine)5gを50℃以下でゆっくり投入して反応温度90℃上で3時間の間攪拌する。反応物を再び30℃未満に冷却してThionyl chloride(4g)を30℃未満でゆっくり滴加する。投入が完了すると反応物を温度95℃条件で1時間の間攪拌する。その後常温に冷却して10℃以下の条件で水300mLを用いて中和する。そして複数回水を用いて固体を洗浄する。
前記合成例1で、cyclohexylamineの代わりにcyclopentylamineを使用したことを除いては合成例1と同様に行い、下記化学式17で表される化合物を合成した。
250mLフラスコに4-(2-phenylphenoxy)phthalonitrile(4g)、Diazabicycloundec-7-ene(2.5g)、1-ペンタノール(40mL)を入れて加熱して固体が溶けた後、Copper acetate(1.8g)を入れて加熱しながら還流する。反応終了後に溶媒を除去して、カラムクロマトグラフィーで精製する。得られた固体にジクロロメタンを適当に入れて固体を溶かした後メタノールを添加して結晶化した。この時、得られた固体を濾過して真空乾燥して下記化学式18で表される化合物を合成した。
前記合成例1で、cyclohexylamineの代わりに2-ethylhexylamineを使用したことを除いては前記合成例1と同様に行い、下記化学式19で表される化合物を合成した。
前記合成例1で、cyclohexylamineの代わりにmethyl leucinateを使用したことを除いては前記合成例1と同様に行い、下記化学式20で表される化合物を合成した。
窒素ガスが還流して温度調節が容易なように冷却装置が設けられた1Lの反応器にn-ブチルアクリレート99重量部、2-ヒドロキシエチルアクリレート1重量部を含む単量体混合物100重量部、酢酸エチル150重量部を投入して攪拌しながら窒素ガスを1時間の間投入して反応器内の酸素を窒素に置換させた後反応器温度を70℃に維持した。開始剤として2,2-アゾビスイソブチロニトリル0.06重量部を投入して8時間の間反応させて(メタ)アクリル系共重合体含有溶液を製造した。前記(メタ)アクリル系共重合体はTgが-46℃、重量平均分子量は1,100,000g/molであった。酢酸エチルを添加して19.4重量%の(メタ)アクリル系共重合体溶液を製造した。
製造した熱硬化性コート層用組成物を反射防止フィルム(基材フィルムであるPETフィルムの上部面にハードコート層、高屈折率層、低屈折率層が順次積層された反射防止フィルム、反射率:0.2%、DNP社)の基材フィルムであるPETフィルムの下部面にバーコーターで直接塗布して90℃オーブンで4分間乾燥させて厚さ20μmの熱硬化コート層を含む光学部材用シートを製造した。
実施例1の合成例1の化合物(化学式10で表示)の代わりに合成例2の化合物(化学式17で表示)を使用したことを除いては実施例1と同様にして、光学部材を製造した。
実施例1の合成例1の化合物(化学式10で表示)の代わりに比較合成例1の化合物(化学式18で表示)を使用したことを除いては実施例1と同様にして、光学部材を製造した。
実施例1の合成例1の化合物(化学式10で表示)の代わりにフタロシアニン系染料(IN-88,旭成(ウクソン)化学社、最大吸収波長:752nm)を使用したことを除いては実施例1と同様にして、光学部材を製造した
比較例3
実施例1の合成例1の化合物(化学式10で表示)の代わりに比較合成例2の化合物(化学式19で表示)を使用したことを除いては実施例1と同様にして、光学部材を製造した。
実施例1の合成例1の化合物(化学式10で表示)の代わりに比較合成例3の化合物(化学式20で表示)を使用したことを除いては実施例1と同様にして、光学部材を製造した。
前記実施例1および比較例2による光学部材をUV-vis分光光度計を用いて波長別の透過率を測定し、その結果を表1に示した。
耐光信頼性改善の有無を確認するために、前記実施例1、実施例2および比較例1ないし比較例4による光学部材に対してXenon Test Chamber(Q-SUN)で[光源ランプ:Xenonランプ、照射強度:0.35W/cm2、照射温度:63℃、照射時間:500時間、照射方向:反射防止フィルム側からの照射]の条件で照射する前と照射した後の各化合物の最大吸収波長で光透過率を測定した後光透過率変化量で耐光信頼性を評価して、その結果を下記表2に示した。
20 量子ドット含有層
30 カラーフィルタ
40 基材
50 粘着層
60 染料含有層
70 反射防止層
80 反射防止フィルム
100 ディスプレイ装置
Claims (17)
- 下記化学式1で表される化合物:
前記化学式1において、
Mは2個の水素原子、2価の金属原子、3価の置換金属原子、4価の置換金属原子、水酸化金属原子または酸化金属原子であり、
R1~R16はそれぞれ独立して、水素、置換若しくは非置換されたC1~C20アルキル基、置換若しくは非置換されたC3~C20シクロアルキル基、置換若しくは非置換されたC6~C20アリール基、置換若しくは非置換されたC2~C20ヘテロアリール基、下記化学式2で表されるスルホニルアミド基、またはこれらの組み合わせであり、
R1~R8の少なくとも一つおよびR9~R16の少なくとも一つは下記化学式2で表されるスルホニルアミド基である;
前記化学式2において、
R17およびR18はそれぞれ独立して水素、置換若しくは非置換されたC1~C20アルキル基、置換若しくは非置換されたC3~C20シクロアルキル基、置換若しくは非置換されたC6~C20アリール基、または置換若しくは非置換されたC2~C20ヘテロアリール基であり、
R17およびR18の少なくとも一つはC3~C20シクロアルキル基であり、
*は前記化学式1のベンゼン環に結合する部分を意味する。 - R17およびR18はそれぞれ独立して水素または置換若しくは非置換されたC3~C20シクロアルキル基であり、
R17およびR18の少なくとも一つはC3~C20シクロアルキル基である、請求項1に記載の化合物。 - 前記MはCu、Co、Zn、V(=O)またはAgである、請求項1に記載の化合物。
- 前記R1~R4の少なくとも一つは前記化学式2で表されるスルホニルアミド基であり、
前記R5~R8の少なくとも一つは前記化学式2で表されるスルホニルアミド基であり、
前記R9~R12の少なくとも一つは前記化学式2で表されるスルホニルアミド基であり、
前記R13~R16の少なくとも一つは前記化学式2で表されるスルホニルアミド基である、請求項1に記載の化合物。 - 前記R1~R4の少なくとも一つは前記化学式2で表されるスルホニルアミド基であり、残りは水素原子であり、
前記R5~R8の少なくとも一つは前記化学式2で表されるスルホニルアミド基であり、残りは水素原子であり、
前記R9~R12の少なくとも一つは前記化学式2で表されるスルホニルアミド基であり、残りは水素原子であり、
前記R13~R16の少なくとも一つは前記化学式2で表されるスルホニルアミド基であり、残りは水素原子である、請求項1に記載の化合物。 - 前記化合物は赤色吸収染料である、請求項1に記載の化合物。
- 前記染料は650nm~750nmの波長で最大吸収ピークを有する、請求項8に記載の化合物。
- 請求項1から9のいずれか一項による化合物を含む、反射防止フィルム。
- 前記反射防止フィルムは粘着層および前記粘着層上に形成された反射防止層を含み、
前記化合物は前記粘着層に含まれる、請求項10に記載の反射防止フィルム。 - 前記反射防止フィルムは粘着層、染料含有層および前記染料含有層上に形成された反射防止層を含み、
前記化合物は前記染料含有層に含まれる、請求項10に記載の反射防止フィルム。 - 請求項10による反射防止フィルムを含む、ディスプレイ装置。
- 前記ディスプレイ装置は量子ドット含有層をさらに含む、請求項13に記載のディスプレイ装置。
- 前記ディスプレイ装置は光源、カラーフィルタおよび基材をさらに含む、請求項13に記載のディスプレイ装置。
- 前記ディスプレイ装置は、
前記光源上に前記量子ドット含有層が位置し、
前記量子ドット含有層上に前記カラーフィルタが位置し、
前記カラーフィルタ上に前記基材が位置し、
前記基材上に前記反射防止フィルムが位置する、請求項15に記載のディスプレイ装置。 - 前記基材はガラス基材を含む、請求項15に記載のディスプレイ装置。
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