JP7193545B2 - レジスト用途の光酸発生剤としての環状スルホン酸エステル化合物 - Google Patents
レジスト用途の光酸発生剤としての環状スルホン酸エステル化合物 Download PDFInfo
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- JP7193545B2 JP7193545B2 JP2020547339A JP2020547339A JP7193545B2 JP 7193545 B2 JP7193545 B2 JP 7193545B2 JP 2020547339 A JP2020547339 A JP 2020547339A JP 2020547339 A JP2020547339 A JP 2020547339A JP 7193545 B2 JP7193545 B2 JP 7193545B2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
- C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2037—Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Description
本願は、2018年3月16日に出願された米国特許仮出願第62/644,288号に基づく優先権を主張する2019年3月14に出願された国際特許出願第PCT/US2019/022252号の国内移行出願であり、参照により、それらの全体が本明細書に援用される。
本開示は、新規な光酸発生剤化合物(「PAG」)、及びそのようなPAG化合物を含む組成物に関するものである。特には、本開示のPAG化合物は、有機溶剤への溶解性に優れ、フォトリソグラフィープロセスにおいて、従来のPAG化合物よりも感度が高く、性能が良い。
別段の記載のない限り、本明細書及び請求項を含め、本願で用いられている以下の用語は、以下に示す定義を有する。本明細書及び添付の請求項で使用する場合、「a」、「an」及び「the」という単数形には、文脈上明らかに別段に解される場合を除き、複数の指示対象が含まれることに留意されたい。
以下でさらに詳細に説明するように、本開示によるスルホン酸誘導体化合物は、光酸発生剤として使用できる。驚くべきことに、本開示のPAG化合物は、溶解性に優れ、電磁放射線、特に、波長が150~500nmの範囲、好ましくは300~450nmの範囲、より好ましくは350~440nmの範囲、より好ましくは波長が365nm(i線)、405(h線)及び436nm(g線)の電磁放射線に対する光反応性に優れることによって特徴付けられることを発見した。
本明細書に開示されているアダマンタン含有スルホン酸エステル化合物の合成方法には、特に制限はなく、これらの化合物の合成には、いずれかの周知のアプローチを使用できる。化合物A1の合成をスキーム1に示した。
本開示の組成物は、(i)式(I)の光酸発生剤を少なくとも1つ、(ii)酸の存在下で、水性溶液への溶解性が変化し得る化合物を少なくとも1つ、(iii)有機溶剤、及び任意に(iv)添加剤を含む。
(i)式(I)の少なくとも1つの光酸発生剤化合物を0.05~15重量%、好ましくは0.1~12.5重量%、最も好ましくは1~10重量%、
(ii)塩基可溶性または塩基不溶性であってよい少なくとも1つのフォトレジストポリマーまたはフォトレジストコポリマーを5~50重量%、好ましくは7.5~45重量%、最も好ましくは10~40重量%、及び
(iv)追加の添加剤を0~10重量%、好ましくは0.01~7.5重量%、最も好ましくは0.1~5重量%含み、その組成物の残部は、有機溶剤(iii)である。
本開示は、基板と、その基板上にパターン化構造で塗布されているコーティングとを含む複合体の作製プロセスであって、
(a)本開示による組成物の層を基板の表面上に塗布し、有機溶剤(iii)を少なくとも部分的に除去する工程、
(b)その層の所定の区域を電磁放射線に露光し、それによって、電磁放射線を露光した区域において、化合物(i)から酸を放出させる工程、
(c)任意に、その層を加熱して、酸が放出された区域に、化合物(ii)をもたらし、水性溶液への溶解性を変化させる工程、及び
(d)任意に、その層を少なくとも部分的に除去する工程、
を含むプロセスを提供する。
Claims (4)
- 前記溶剤が、2-メトキシエチルエーテル(ジグリム)、エチレングリコールモノメチルエーテル及びプロピレングリコールモノメチルエーテルからなる群から選択されているグリコールエーテルである、請求項2に記載の組成物。
- 前記光酸発生剤化合物が、前記組成物中に1~10重量%存在し、前記少なくとも1つのフォトレジストポリマーまたはフォトレジストコポリマーが、10~40重量%存在し、前記組成物の残部が、前記有機溶剤である、請求項2に記載の組成物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2022149007A JP2022184974A (ja) | 2018-03-16 | 2022-09-20 | レジスト用途の光酸発生剤としての環状スルホン酸エステル化合物 |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201862644288P | 2018-03-16 | 2018-03-16 | |
US62/644,288 | 2018-03-16 | ||
PCT/US2019/022252 WO2019178344A1 (en) | 2018-03-16 | 2019-03-14 | Cyclic sulfonate compounds as photoacid generators in resist applications |
Related Child Applications (1)
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JP2022149007A Division JP2022184974A (ja) | 2018-03-16 | 2022-09-20 | レジスト用途の光酸発生剤としての環状スルホン酸エステル化合物 |
Publications (2)
Publication Number | Publication Date |
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JP2021517562A JP2021517562A (ja) | 2021-07-26 |
JP7193545B2 true JP7193545B2 (ja) | 2022-12-20 |
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JP2020547339A Active JP7193545B2 (ja) | 2018-03-16 | 2019-03-14 | レジスト用途の光酸発生剤としての環状スルホン酸エステル化合物 |
JP2022149007A Pending JP2022184974A (ja) | 2018-03-16 | 2022-09-20 | レジスト用途の光酸発生剤としての環状スルホン酸エステル化合物 |
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JP2022149007A Pending JP2022184974A (ja) | 2018-03-16 | 2022-09-20 | レジスト用途の光酸発生剤としての環状スルホン酸エステル化合物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US11292764B2 (ja) |
EP (1) | EP3765902A1 (ja) |
JP (2) | JP7193545B2 (ja) |
KR (2) | KR20230039770A (ja) |
CN (1) | CN111819495B (ja) |
TW (1) | TWI827584B (ja) |
WO (1) | WO2019178344A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20210198468A1 (en) * | 2019-12-31 | 2021-07-01 | Taiwan Semiconductor Manufacturing Co., Ltd. | Photoresist composition and method of manufacturing a semiconductor device |
US20210271164A1 (en) * | 2020-02-27 | 2021-09-02 | Taiwan Semiconductor Manufacturing Co., Ltd. | Photoresist composition and method of manufacturing a semiconductor device |
WO2022272226A1 (en) * | 2021-06-23 | 2022-12-29 | Heraeus Epurio Llc | Oxathianium ion-containing sulfonic acid derivative compound as photoacid generators in resist applications |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005148291A (ja) | 2003-11-13 | 2005-06-09 | Fuji Photo Film Co Ltd | 感光性組成物及びそれを用いたパターン形成方法 |
WO2007124092A3 (en) | 2006-04-21 | 2007-12-13 | Cornell Res Foundation Inc | Photoacid generator compounds and compositions |
US20090258315A1 (en) | 2008-04-09 | 2009-10-15 | Cornell Research Foundation, Inc. | Photoacid generator compounds and compositions |
JP2009294394A (ja) | 2008-06-04 | 2009-12-17 | Tokyo Ohka Kogyo Co Ltd | 化合物、酸発生剤、レジスト組成物およびレジストパターン形成方法 |
JP2013147485A (ja) | 2011-06-09 | 2013-08-01 | Sumitomo Chemical Co Ltd | 塩、レジスト組成物及びレジストパターンの製造方法 |
Family Cites Families (12)
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IE57143B1 (en) | 1984-06-01 | 1992-05-06 | Rohm & Haas | Photosensitive coating compositions,thermally stable coating prepared from them,and the use of such coatings in forming thermally stable polymer images |
US5128232A (en) | 1989-05-22 | 1992-07-07 | Shiply Company Inc. | Photoresist composition with copolymer binder having a major proportion of phenolic units and a minor proportion of non-aromatic cyclic alcoholic units |
US7371503B2 (en) | 2003-01-22 | 2008-05-13 | Jsr Corporation | Sulfonium salt compound, photoacid generator, and positive-tone radiation-sensitive resin composition |
JP5622448B2 (ja) * | 2010-06-15 | 2014-11-12 | 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、化合物 |
JP5542043B2 (ja) * | 2010-06-25 | 2014-07-09 | 富士フイルム株式会社 | パターン形成方法、感活性光線性又は感放射線性樹脂組成物、及びレジスト膜 |
JP5961363B2 (ja) | 2010-11-15 | 2016-08-02 | 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 | ラクトン光酸発生剤、これを含む樹脂およびフォトレジスト |
JP5715852B2 (ja) * | 2011-02-28 | 2015-05-13 | 富士フイルム株式会社 | パターン形成方法、感活性光線性又は感放射線性樹脂組成物及びレジスト膜 |
EP2527918A2 (en) | 2011-05-27 | 2012-11-28 | Rohm and Haas Electronic Materials LLC | Photoresist composition |
JP5816543B2 (ja) | 2011-12-27 | 2015-11-18 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、並びに、該組成物を用いたレジスト膜、パターン形成方法、及び電子デバイスの製造方法 |
JP6038284B2 (ja) * | 2012-04-19 | 2016-12-07 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | スルホニウム化合物、それらの製造および使用 |
JP6126878B2 (ja) | 2013-03-15 | 2017-05-10 | 富士フイルム株式会社 | パターン形成方法、感活性光線性又は感放射線性樹脂組成物、感活性光線性又は感放射線性膜及び電子デバイスの製造方法 |
JP6695203B2 (ja) | 2015-04-24 | 2020-05-20 | 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 |
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2019
- 2019-03-14 KR KR1020237008622A patent/KR20230039770A/ko not_active Application Discontinuation
- 2019-03-14 EP EP19713997.5A patent/EP3765902A1/en active Pending
- 2019-03-14 WO PCT/US2019/022252 patent/WO2019178344A1/en active Application Filing
- 2019-03-14 US US16/495,719 patent/US11292764B2/en active Active
- 2019-03-14 CN CN201980018154.4A patent/CN111819495B/zh active Active
- 2019-03-14 TW TW108108711A patent/TWI827584B/zh active
- 2019-03-14 KR KR1020207026212A patent/KR102546299B1/ko active IP Right Grant
- 2019-03-14 JP JP2020547339A patent/JP7193545B2/ja active Active
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2022
- 2022-09-20 JP JP2022149007A patent/JP2022184974A/ja active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2005148291A (ja) | 2003-11-13 | 2005-06-09 | Fuji Photo Film Co Ltd | 感光性組成物及びそれを用いたパターン形成方法 |
WO2007124092A3 (en) | 2006-04-21 | 2007-12-13 | Cornell Res Foundation Inc | Photoacid generator compounds and compositions |
US20090258315A1 (en) | 2008-04-09 | 2009-10-15 | Cornell Research Foundation, Inc. | Photoacid generator compounds and compositions |
JP2009294394A (ja) | 2008-06-04 | 2009-12-17 | Tokyo Ohka Kogyo Co Ltd | 化合物、酸発生剤、レジスト組成物およびレジストパターン形成方法 |
JP2013147485A (ja) | 2011-06-09 | 2013-08-01 | Sumitomo Chemical Co Ltd | 塩、レジスト組成物及びレジストパターンの製造方法 |
Also Published As
Publication number | Publication date |
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KR20200120696A (ko) | 2020-10-21 |
CN111819495B (zh) | 2023-07-18 |
TW201940465A (zh) | 2019-10-16 |
US11292764B2 (en) | 2022-04-05 |
WO2019178344A1 (en) | 2019-09-19 |
US20210002213A9 (en) | 2021-01-07 |
CN111819495A (zh) | 2020-10-23 |
EP3765902A1 (en) | 2021-01-20 |
KR20230039770A (ko) | 2023-03-21 |
US20200017441A1 (en) | 2020-01-16 |
KR102546299B1 (ko) | 2023-06-21 |
TWI827584B (zh) | 2024-01-01 |
JP2021517562A (ja) | 2021-07-26 |
JP2022184974A (ja) | 2022-12-13 |
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