JP2016095497A5 - - Google Patents
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- Publication number
- JP2016095497A5 JP2016095497A5 JP2015198573A JP2015198573A JP2016095497A5 JP 2016095497 A5 JP2016095497 A5 JP 2016095497A5 JP 2015198573 A JP2015198573 A JP 2015198573A JP 2015198573 A JP2015198573 A JP 2015198573A JP 2016095497 A5 JP2016095497 A5 JP 2016095497A5
- Authority
- JP
- Japan
- Prior art keywords
- repeating units
- substituted
- photoacid generating
- independently
- unsubstituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920000642 polymer Polymers 0.000 claims description 27
- 125000000524 functional group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 15
- 229920002120 photoresistant polymer Polymers 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 12
- 150000001733 carboxylic acid esters Chemical group 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- -1 sulfonamide anion Chemical class 0.000 claims description 8
- 230000002708 enhancing effect Effects 0.000 claims description 7
- 150000002596 lactones Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 229920001515 polyalkylene glycol Chemical class 0.000 claims description 5
- 150000008053 sultones Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 3
- 239000008137 solubility enhancer Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 8
- 229940116333 ethyl lactate Drugs 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 3
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MSLTZKLJPHUCPU-WNQIDUERSA-M (2s)-2-hydroxypropanoate;tetrabutylazanium Chemical compound C[C@H](O)C([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MSLTZKLJPHUCPU-WNQIDUERSA-M 0.000 description 1
- FJALTVCJBKZXKY-UHFFFAOYSA-M (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;triphenylsulfanium Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FJALTVCJBKZXKY-UHFFFAOYSA-M 0.000 description 1
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
- OCOSJALLUPFFEI-UHFFFAOYSA-M OC12CC3(CC(CC(C1)C3)C2)C(=O)[O-].C2(=CC=CC=C2)[S+](C2=CC=CC=C2)C2=CC=CC=C2 Chemical compound OC12CC3(CC(CC(C1)C3)C2)C(=O)[O-].C2(=CC=CC=C2)[S+](C2=CC=CC=C2)C2=CC=CC=C2 OCOSJALLUPFFEI-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- FWYVYMWDETVPRV-UHFFFAOYSA-N [O-]C(=O)C12CC3CC(CC(C3)C1)C2.CC(C)(C)c1ccc2[SH+]c3ccccc3-c2c1-c1ccccc1 Chemical compound [O-]C(=O)C12CC3CC(CC(C3)C1)C2.CC(C)(C)c1ccc2[SH+]c3ccccc3-c2c1-c1ccccc1 FWYVYMWDETVPRV-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 229940059260 amidate Drugs 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000008027 tertiary esters Chemical class 0.000 description 1
- KOFQUBYAUWJFIT-UHFFFAOYSA-M triphenylsulfanium;hydroxide Chemical compound [OH-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 KOFQUBYAUWJFIT-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462062348P | 2014-10-10 | 2014-10-10 | |
| US62/062,348 | 2014-10-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016095497A JP2016095497A (ja) | 2016-05-26 |
| JP2016095497A5 true JP2016095497A5 (enExample) | 2017-02-02 |
| JP6280529B2 JP6280529B2 (ja) | 2018-02-14 |
Family
ID=55655372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015198573A Active JP6280529B2 (ja) | 2014-10-10 | 2015-10-06 | フォトレジスト組成物及び電子デバイスを形成する関連方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9551930B2 (enExample) |
| JP (1) | JP6280529B2 (enExample) |
| KR (1) | KR101874481B1 (enExample) |
| CN (1) | CN105511228B (enExample) |
| TW (1) | TWI615676B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9606434B2 (en) * | 2014-10-10 | 2017-03-28 | Rohm And Haas Electronic Materials, Llc | Polymer comprising repeat units with photoacid-generating functionality and base-solubility-enhancing functionality, and associated photoresist composition and electronic device forming method |
| US9527936B2 (en) | 2014-10-10 | 2016-12-27 | Rohm And Haas Electronic Materials Llc | Polymer comprising repeat units with photoacid-generating functionality and base-solubility-enhancing functionality, and associated photoresist composition and electronic device forming method |
| US9557642B2 (en) | 2014-10-10 | 2017-01-31 | Rohm And Haas Electronic Materials Llc | Photoresist composition and associated method of forming an electronic device |
| US9551930B2 (en) | 2014-10-10 | 2017-01-24 | Rohm And Haas Electronic Materials Llc | Photoresist composition and associated method of forming an electronic device |
| JP7240301B2 (ja) | 2019-11-07 | 2023-03-15 | 信越化学工業株式会社 | レジスト組成物及びパターン形成方法 |
| US20210200084A1 (en) * | 2019-12-31 | 2021-07-01 | Rohm And Haas Electronic Materials Llc | Polymers and photoresist compositions |
| KR102811047B1 (ko) | 2020-01-20 | 2025-05-22 | 삼성전자주식회사 | 광분해성 화합물 및 이를 포함하는 포토레지스트 조성물과 집적회로 소자의 제조 방법 |
| JP7758480B2 (ja) * | 2020-07-01 | 2025-10-22 | 住友化学株式会社 | 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法 |
| US12050402B2 (en) * | 2021-01-21 | 2024-07-30 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3902115A1 (de) | 1989-01-25 | 1990-08-02 | Basf Ag | Strahlungsempfindliche polymere |
| JP3613491B2 (ja) | 1996-06-04 | 2005-01-26 | 富士写真フイルム株式会社 | 感光性組成物 |
| US7569326B2 (en) * | 2006-10-27 | 2009-08-04 | Shin-Etsu Chemical Co., Ltd. | Sulfonium salt having polymerizable anion, polymer, resist composition, and patterning process |
| EP2101217B1 (en) * | 2008-03-14 | 2011-05-11 | Shin-Etsu Chemical Co., Ltd. | Sulfonium salt-containing polymer, resist compositon, and patterning process |
| JP4998746B2 (ja) * | 2008-04-24 | 2012-08-15 | 信越化学工業株式会社 | スルホニウム塩を含む高分子化合物、レジスト材料及びパターン形成方法 |
| JP5201363B2 (ja) * | 2008-08-28 | 2013-06-05 | 信越化学工業株式会社 | 重合性アニオンを有するスルホニウム塩及び高分子化合物、レジスト材料及びパターン形成方法 |
| TWI400226B (zh) | 2008-10-17 | 2013-07-01 | Shinetsu Chemical Co | 具有聚合性陰離子之鹽及高分子化合物、光阻劑材料及圖案形成方法 |
| JP5401910B2 (ja) | 2008-10-17 | 2014-01-29 | セントラル硝子株式会社 | 重合性アニオンを有する含フッ素スルホン塩類とその製造方法、含フッ素樹脂、レジスト組成物及びそれを用いたパターン形成方法 |
| JP5851688B2 (ja) | 2009-12-31 | 2016-02-03 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | 感光性組成物 |
| JP5216032B2 (ja) * | 2010-02-02 | 2013-06-19 | 信越化学工業株式会社 | 新規スルホニウム塩、高分子化合物、高分子化合物の製造方法、レジスト材料及びパターン形成方法 |
| US9182664B2 (en) * | 2010-10-13 | 2015-11-10 | Central Glass Company, Limited | Polymerizable fluorine-containing sulfonate, fluorine-containing sulfonate resin, resist composition and pattern-forming method using same |
| JP5521996B2 (ja) * | 2010-11-19 | 2014-06-18 | 信越化学工業株式会社 | スルホニウム塩を含む高分子化合物、レジスト材料及びパターン形成方法、並びにスルホニウム塩単量体及びその製造方法 |
| JP5802394B2 (ja) | 2011-01-17 | 2015-10-28 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法及び高分子化合物 |
| JP5677135B2 (ja) | 2011-02-23 | 2015-02-25 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法および高分子化合物 |
| JP5715890B2 (ja) | 2011-06-10 | 2015-05-13 | 東京応化工業株式会社 | 高分子化合物の製造方法 |
| US20120322006A1 (en) | 2011-06-20 | 2012-12-20 | Central Glass Company, Limited | Fluorine-Containing Sulfonate Resin, Resist Composition and Pattern Formation Method |
| JP2013227466A (ja) * | 2011-06-20 | 2013-11-07 | Central Glass Co Ltd | 含フッ素スルホン酸塩樹脂、含フッ素ｎ−スルホニルオキシイミド樹脂、レジスト組成物及びそれを用いたパターン形成方法 |
| JP6019849B2 (ja) * | 2011-09-08 | 2016-11-02 | セントラル硝子株式会社 | 含フッ素スルホン酸塩類、含フッ素スルホン酸塩樹脂、レジスト組成物及びそれを用いたパターン形成方法 |
| JP6006928B2 (ja) | 2011-11-02 | 2016-10-12 | 東京応化工業株式会社 | 高分子化合物の製造方法 |
| KR101663122B1 (ko) * | 2012-01-23 | 2016-10-06 | 샌트랄 글래스 컴퍼니 리미티드 | 함불소 술폰산염류, 함불소 술폰산염 수지, 레지스트 조성물 및 그것을 사용한 패턴 형성 방법 |
| US8795948B2 (en) | 2012-03-22 | 2014-08-05 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern and polymeric compound |
| JP5783137B2 (ja) * | 2012-06-15 | 2015-09-24 | 信越化学工業株式会社 | スルホニウム塩、高分子化合物、レジスト材料及びパターン形成方法 |
| JP5913241B2 (ja) * | 2012-09-15 | 2016-04-27 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | 複数の酸発生剤化合物を含むフォトレジスト |
| TWI498675B (zh) | 2012-09-15 | 2015-09-01 | 羅門哈斯電子材料有限公司 | 酸產生劑化合物及含該化合物之光阻劑 |
| US8945814B2 (en) | 2012-09-15 | 2015-02-03 | Rohm And Haas Electronic Materials Llc | Acid generators and photoresists comprising same |
| JP6106432B2 (ja) * | 2012-12-28 | 2017-03-29 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、高分子化合物 |
| JP6571912B2 (ja) | 2012-12-31 | 2019-09-04 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | 樹状化合物、フォトレジスト組成物、および電子デバイスを作製する方法 |
| US10179778B2 (en) | 2013-09-27 | 2019-01-15 | Rohm And Haas Electronic Materials Llc | Substituted aryl onium materials |
| US9581901B2 (en) | 2013-12-19 | 2017-02-28 | Rohm And Haas Electronic Materials Llc | Photoacid-generating copolymer and associated photoresist composition, coated substrate, and method of forming an electronic device |
| US10345700B2 (en) | 2014-09-08 | 2019-07-09 | International Business Machines Corporation | Negative-tone resist compositions and multifunctional polymers therein |
| US9557642B2 (en) | 2014-10-10 | 2017-01-31 | Rohm And Haas Electronic Materials Llc | Photoresist composition and associated method of forming an electronic device |
| US9527936B2 (en) | 2014-10-10 | 2016-12-27 | Rohm And Haas Electronic Materials Llc | Polymer comprising repeat units with photoacid-generating functionality and base-solubility-enhancing functionality, and associated photoresist composition and electronic device forming method |
| US9606434B2 (en) | 2014-10-10 | 2017-03-28 | Rohm And Haas Electronic Materials, Llc | Polymer comprising repeat units with photoacid-generating functionality and base-solubility-enhancing functionality, and associated photoresist composition and electronic device forming method |
| US9551930B2 (en) | 2014-10-10 | 2017-01-24 | Rohm And Haas Electronic Materials Llc | Photoresist composition and associated method of forming an electronic device |
-
2015
- 2015-08-24 US US14/833,278 patent/US9551930B2/en active Active
- 2015-10-05 TW TW104132736A patent/TWI615676B/zh active
- 2015-10-06 JP JP2015198573A patent/JP6280529B2/ja active Active
- 2015-10-06 KR KR1020150140570A patent/KR101874481B1/ko active Active
- 2015-10-09 CN CN201510649917.9A patent/CN105511228B/zh active Active
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