JP2021512179A - 架橋剤化合物、これを含む感光性組成物、およびこれを利用した感光材料 - Google Patents
架橋剤化合物、これを含む感光性組成物、およびこれを利用した感光材料 Download PDFInfo
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- JP2021512179A JP2021512179A JP2020528337A JP2020528337A JP2021512179A JP 2021512179 A JP2021512179 A JP 2021512179A JP 2020528337 A JP2020528337 A JP 2020528337A JP 2020528337 A JP2020528337 A JP 2020528337A JP 2021512179 A JP2021512179 A JP 2021512179A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 109
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- 239000000463 material Substances 0.000 title claims abstract description 45
- 125000000524 functional group Chemical group 0.000 claims abstract description 100
- 239000000126 substance Substances 0.000 claims description 232
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- 229920000642 polymer Polymers 0.000 claims description 44
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- 229920001577 copolymer Polymers 0.000 claims description 29
- 229920005575 poly(amic acid) Polymers 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000962 organic group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 21
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- 239000001257 hydrogen Substances 0.000 claims description 18
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- 229910052710 silicon Inorganic materials 0.000 claims description 17
- 239000010703 silicon Substances 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 125000000732 arylene group Chemical group 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
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- 125000006850 spacer group Chemical group 0.000 description 2
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical group C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-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
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000006836 terphenylene group Chemical group 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
- 150000003512 tertiary amines Chemical group 0.000 description 1
- KYWIYKKSMDLRDC-UHFFFAOYSA-N undecan-2-one Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Abstract
Description
本出願は、2018年12月21日付の韓国特許出願第10−2018−0167760号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示された全ての内容は本明細書の一部として含まれる。
[化学式1]
本発明に係る架橋剤化合物は、上記化学式1で表される特定の化学構造を有することができる。前記架橋剤化合物の物理/化学的特性は、上述した化学式1の特定構造に起因すると考えられる。
[化学式2]
[化学式3]
[化学式1−1]
[化学式1−2]
[化学式1−3]
一方、本発明の一実施形態によれば、上記化学式1で表される架橋剤化合物を含む、感光性組成物が提供され得る。
[化学式6]
[化学式8]
[化学式9]
[化学式10]
[化学式12]
[化学式14]
[化学式8−1]
[化学式10−1]
[化学式10−4]
一方、本発明のさらに他の実施形態によれば、前記一実施形態の感光性組成物の硬化物を含む感光材料が提供され得る。前記硬化物とは、前記一実施形態の感光性組成物の硬化工程を経て得られる物質を意味する。
[化学式11]
前記製造例1の反応物であるN4,N4,N4',N4'−テトラキス(2−ヒドロキシエチル)ビフェニル−4,4'−ジカルボキシアミド(N4,N4,N4',N4'−tetrakis(2−hydroxyethyl)biphenyl−4,4'−dicarboxamide)を比較製造例1の架橋剤として使用した。
下記化学式Aで表されるジアミンDA1 5.0g(13.3mmol)を無水N−メチルピロリドン(NMP)71.27gに完全に溶かした。そして、ice bath下で1,3−ジメチル−シクロブタン−1,2,3,4−テトラカルボン酸二無水物(DMCBDA)2.92g(13.03mmol)を前記溶液に添加し、約16時間常温で攪拌して重合体P−1を製造した。GPCにより前記重合体P−1の分子量を確認した結果、数平均分子量(Mn)が15,500g/molであり、重量平均分子量(Mw)が31,000g/molであった。そして、重合体P−1のモノマー構造は、使用したモノマーの当量比によって決められるもので、分子内のイミド構造の比率が50.5%、アミック酸構造の比率が49.5%であった。
[化学式A]
[化学式B]
前記製造例1で得られた架橋剤を全体溶液に対して10重量%添加したことを除いて、前記実施例1と同様の方法で、感光性組成物を製造した。
前記製造例1で得られた架橋剤の代わりに前記製造例2で得られた架橋剤を添加したことを除いて、前記実施例1と同様の方法で、感光性組成物を製造した。
前記製造例1で得られた架橋剤の代わりに前記製造例2で得られた架橋剤を全体溶液に対して10重量%添加したことを除いて、前記実施例2と同様の方法で、感光性組成物を製造した。
前記製造例1で得られた架橋剤の代わりに比較製造例1におけるN4,N4,N4',N4'−テトラキス(2−ヒドロキシエチル)ビフェニル−4,4'−ジカルボキシアミド(N4,N4,N4',N4'−tetrakis(2−hydroxyethyl)biphenyl−4,4'−dicarboxamide)を添加したことを除いて、前記実施例1と同様の方法で、感光性組成物を製造した。
前記実施例および比較例で製造した感光性組成物に対して、初期粘度および常温で30日間保管した以降の粘度をそれぞれ測定して、下記数式1によって粘度の変化率を測定した。
粘度変化率(%)=(常温で30日間保管後の感光性組成物の粘度−初期感光性組成物の粘度)/初期感光性組成物の粘度*100
前記実施例および比較例の感光性組成物でそれぞれ使用した架橋剤に対して、上記表1の架橋剤の添加量を満たすように溶媒(γ−ブチロラクトン)に添加した後、10秒間混合した混合溶液を製造して、混合溶液の透明度を肉眼で確認し、以下の基準により溶解性を評価した。
Claims (14)
- 上記化学式1中、
L1およびL2は、それぞれ独立して、炭素数1〜5のアルキレン基である、請求項1または2に記載の架橋剤化合物。 - 感光材料用途に使用される、請求項1から5のいずれか一項に記載の架橋剤化合物。
- 請求項1から6のいずれか一項に記載の架橋剤化合物を含む、感光性組成物。
- 上記化学式4で表される化合物の含有量は、化学式1で表される架橋剤化合物100重量部に対して0.001重量部〜10重量部である、請求項9に記載の感光性組成物。
- 前記少なくとも1つ以上のカルボキシル基を含む高分子は、
下記化学式6で表される繰り返し単位を含む第1ポリアミック酸(共)重合体、および下記化学式7で表される繰り返し単位を含む第2ポリアミック酸(共)重合体を含む、請求項8から11のいずれか一項に記載の感光性組成物:
[化学式6]
[化学式8]
R13〜R18は、それぞれ独立して、水素または炭素数1〜6のアルキル基であり、
L'は、単一結合、−O−、−CO−、−COO−、−S−、−SO−、−SO2−、−CR19R20−、−(CH2)Z−、−O(CH2)ZO−、−COO(CH2)ZOCO−、−CONH−、またはフェニレンの中から選択されるいずれか一つであり、
R19およびR20は、それぞれ独立して、水素、炭素数1〜10のアルキル基または炭素数1〜10のハロアルキル基であり、
zは1〜10の整数であり、
Y3は、下記化学式9で表される2価の有機基であり、
[化学式9]
Tは、上記化学式8で表される4価の有機基であり、
D1およびD2は、それぞれ独立して、炭素数1〜20のアルキレン基、炭素数1〜10のヘテロアルキレン基、炭素数3〜20のシクロアルキレン基、炭素数6〜20のアリーレン基または炭素数2〜20のヘテロアリーレン基の中から選択されるいずれか一つであり、
Y6は、下記化学式10で表される2価の有機基であり、
[化学式10]
A'は、15族元素であり、
R'は、水素、または炭素数1〜10のアルキルであり、
aは、1〜3の整数であり、
Z1〜Z4のうち少なくとも一つは窒素であり、
残りは炭素である。 - 請求項7から12のいずれか一項に記載の感光性組成物の硬化物を含む、感光材料。
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CN111601843A (zh) | 2020-08-28 |
CN111601843B (zh) | 2021-12-07 |
JP7124871B2 (ja) | 2022-08-24 |
WO2020130261A1 (ko) | 2020-06-25 |
KR102238704B1 (ko) | 2021-04-08 |
EP3702403A4 (en) | 2021-04-14 |
KR20200078139A (ko) | 2020-07-01 |
TWI725496B (zh) | 2021-04-21 |
EP3702403A1 (en) | 2020-09-02 |
US20210061976A1 (en) | 2021-03-04 |
US11754921B2 (en) | 2023-09-12 |
TW202024102A (zh) | 2020-07-01 |
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