TWI311136B - - Google Patents
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- TWI311136B TWI311136B TW091108371A TW91108371A TWI311136B TW I311136 B TWI311136 B TW I311136B TW 091108371 A TW091108371 A TW 091108371A TW 91108371 A TW91108371 A TW 91108371A TW I311136 B TWI311136 B TW I311136B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/16—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Nitrogen Condensed Heterocyclic Rings (AREA)
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Description
1311136 A7 B7 五、發明説明（〇 技術領域 本發明有關薰草素（coumarin)衍生物者，特別是有關 作爲光吸收劑、發光劑有用之新穎之薰草素衍生物者。 技術領域 隨著資訊化時代之來臨，在多種多樣之領域都在採用 光化學性聚合，而至今其用途已超過合成樹脂之領域並擴 及塗料、印刷用刷板、印刷電路、積體電路等之資訊記錄 及電子設備之領域。光化學性聚合，係藉由光照射而使聚 合性化合物進行聚合之技術，可大致分類爲：對聚合性化 合物直接進行光照射使其活性化以引發聚合之光聚合；及 在光敏化劑之共存狀態下進行光照射，產生光敏化劑之激 活種（active seed)以進行聚合性化合物之聚合之光敏化聚 合。任一種光化學性聚合，均係由曝光光源之點熄而可控 制聚合之引發及終止者，而其特徵爲：因選擇曝光光源之 強度或波長而可容易控制聚合度及聚合速度。並且，一般 由於光化學性聚合之聚合引發之能量較低之故，即使在低 溫，仍進fT聚合。在印刷用刷版及全息照相術（ holography )等之資訊記錄之領域中，如此之光化學性聚合 之優點受重視’而急速提昇因照射氬離子雷射、氯氖雷射 、N d (鈸）—Y A G (釔鋁石榴石）雷射之第二高次諧 波等之可視光而能聚合之光聚合性組成物之需要。 光聚合性組成物中所調配之聚合性化合物或聚合引發 劑，由於其多數係僅吸收紫外線之故，如欲使用可視光進 本紙張尺度適用中國國家^TcNS ) A4規格 1 210X297公釐) ' - (請先閱讀背面之注意事項再填寫本頁) 裝-1311136 A7 B7 V. INSTRUCTION DESCRIPTION OF THE INVENTION (Technical Field) The present invention relates to a coumarin derivative, particularly to a novel xanthene derivative useful as a light absorbing agent or a luminescent agent. With the advent of the era of chemistry, photochemical polymerization has been used in a wide variety of fields, and its use has surpassed the field of synthetic resins and expanded into information recording and electronics for coatings, printing brushes, printed circuits, and integrated circuits. In the field of equipment, photochemical polymerization is a technique in which a polymerizable compound is polymerized by light irradiation, and can be roughly classified into a photopolymerization in which a polymerizable compound is directly irradiated with light to be activated to initiate polymerization; The photosensitizer is irradiated with light to generate an active seed of the photosensitizer to perform photopolymerization polymerization of the polymerization of the polymerizable compound. Any photochemical polymerization is performed by the point of exposure light source. The initiation and termination of the polymerization can be controlled, and the characteristic is that the degree of polymerization can be easily controlled by selecting the intensity or wavelength of the exposure light source. In the field of information recording, such as printing and printing, and holography, etc., The advantages of such photochemical polymerization are valued', and the second higher harmonics of the argon ion laser, the chloranium laser, the Nd (钹)-YAG (yttrium aluminum garnet) laser are rapidly increased. The photopolymerizable composition that can be polymerized by light is required. The polymerizable compound or polymerization initiator formulated in the photopolymerizable composition is suitable for use only in the form of visible light. China National ^TcNS ) A4 Size 1 210X297 mm) ' - (Please read the note on the back and fill out this page)
,1T 經濟部智慧財產局員工消費合作社印製 1311136 A7 經濟部智慧財產局員工消費合作社印製 B7五、發明説明（2) 行光聚合性組成物之聚合時’光敏化劑將成爲不可或缺之 技術要素。光敏化劑必備之特性可舉：在可視領域中之分 子吸光係數（以下將分子吸收係數簡記爲「ε」。）較大 ;可敏化各種聚合性化合物及聚合引發劑；敏化效率較高 :對溶劑之溶解性及與其他調配成分之相溶性；以及安定 性佳等。代表性光敏化劑可例舉：日本特開昭5 4 -1 5 1 0 2 4號公報中所揭不之部花菁（merocyanine)色 素、特開昭5 8 - 2 9 8 0 3號公報中所揭示之酞菁（ cyanine)色素、特開昭5 9 — 5 6 4 0 3號公報中所揭示 之二苯二烯（stilbene )色素、特開昭63 - 23901號 公報中所揭示之薰草素衍生物、特開昭6 4 - 3 3 1 0 4 號公報中所掲示之亞甲藍（methylene blue )衍生物、特開 平6 - 3 2 9 6 5 4號公報中所掲示之哌喃（pyran )衍生 物等，惟此等均具有優缺點而至今尙未在由聚合化合物、 粘拉劑樹脂等複數種材料而成之光聚合性組成物中發現能 經常發揮如前述之各特性者。於是，現狀而言，在光化學 性聚合之新應用領域採用例如資訊記錄或電子設備之領域 中，首先選擇聚合性化合物、粘接劑樹脂等按照用途之光 敏化劑以外之材料，接著，從各種各樣之有機化合物中按 試差法_( trial and error method )方式摸索適合於其等聚合 性化合物或聚合引發劑之方法。 鑑於如此情況，本發明之課題在於提供在可視領域具 有吸收極大値（aborption maximum )之新穎的有機化合物 ，藉以當調製光聚合性組成物時，能擴大光敏化劑之選擇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） ； (請先閲讀背面之注意事項再填寫本頁) 1311136 A7 B7 五、發明説明（3) 範圍者。 發明揭示 爲解決此課題，本發明人注意到在分子內含有由薰草 素環、及具有1個或複數個烴基之萘環、及與該萘環縮合 而成並與此等薰草素環及萘環電子進行電子性共振（ resonance )之五員雜環而成之薰草素衍生物並盡心硏究， 摸索之結果，發現特定之薰草素衍生物由於在可視領域中 之分子吸光係數大且能高效率吸收可視光之故，可作爲在 光化學性聚合中作爲聚合性化合物或爲敏化聚合引發劑用 之材料極爲有用之事實。 亦即’本發明係由於提供可以一般式1或一般式2之 任一式所表示之薰草素衍生物，而解決前述課題者。 式 般 (請先閱讀背面之注意事項再填寫本頁) -裝. 訂, 1T Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperative printing 1311136 A7 Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperative printing B7 V. Invention description (2) Photopolymerization agent will become indispensable when polymerizing photopolymerizable composition Technical elements. The necessary characteristics of the photosensitizer are: the molecular absorption coefficient in the visible field (hereinafter, the molecular absorption coefficient is abbreviated as "ε"); the sensitization of various polymerizable compounds and polymerization initiators; sensitization efficiency is high : Solubility to solvents and compatibility with other formulated components; and good stability. The representative photosensitizer can be exemplified by the merocyanine dye disclosed in Japanese Patent Laid-Open Publication No. Sho. No. 5 4 -1 5 1 0 2 4 The cyanine pigment disclosed in the above, the diphenylene dye disclosed in Japanese Laid-Open Patent Publication No. SHO 59-56-103, and the disclosure of Japanese Patent Publication No. SHO 63-23901 The oxalate derivative, the methylene blue derivative shown in Japanese Patent Publication No. Sho 4-4-3 3 0 4, and the meridan shown in JP-A-6- 3 2 9 6 5 (pyran) derivatives, etc., which have advantages and disadvantages, and have not been found in photopolymerizable compositions composed of a plurality of materials such as a polymer compound or a binder resin, and can often exhibit various characteristics as described above. . Therefore, in the field of new fields of application of photochemical polymerization, for example, in the field of information recording or electronic equipment, first, materials other than a photosensitizing agent such as a polymerizable compound or a binder resin are used, and then, Among various organic compounds, a method suitable for a polymerizable compound or a polymerization initiator is explored by a trial and error method. In view of the above circumstances, an object of the present invention is to provide a novel organic compound having an absorption maximum in the visible field, whereby the photosensitive agent can be expanded when the photopolymerizable composition is modulated. Standard (CNS) A4 size (210X297 mm); (Please read the note on the back and fill out this page) 1311136 A7 B7 V. Description of invention (3) Scope. DISCLOSURE OF THE INVENTION In order to solve the problem, the inventors of the present invention have noted that a naphthoquinone ring having one or a plurality of hydrocarbyl groups and a naphthalene ring condensed with the naphthalene ring are contained in the molecule, and such a oxacin ring is formed. And the naphthoquinone electrons were synthesized by a five-membered heterocyclic ring of electronic resonance (resonance), and the results were found. The specific absorption coefficient of the herbicide derivative in the visible field was found. It can be used as a polymerizable compound or a material for sensitizing a polymerization initiator in photochemical polymerization because it is large and absorbs visible light with high efficiency. In other words, the present invention solves the above problems by providing a herbicidal derivative which can be represented by any of the general formula 1 or the general formula 2. As usual (please read the notes on the back and fill out this page) - loading.
經濟部智慧財產局員工消費合作社印製Ministry of Economic Affairs, Intellectual Property Bureau, employee consumption cooperative, printing
R11R12 本紙張尺度適用中.國國家標準（CNS ) A4規格（210X297公缝） -6- 1311136 A7 B7 五、發明説明（4) 一般式2 :R11R12 This paper size applies to the national standard (CNS) A4 specification (210X297 male seam) -6- 1311136 A7 B7 V. Description of invention (4) General formula 2:
經濟部智慧財產局員工消費合作社印製 (―般式1及一般式2中，X表示碳原子或雜原子。 R 1至1114分別獨立表示氫原子或適當的取代基。但是， R 1及/或112可含有此等所結合之氮原子及尺3或尺4所結 合之碳原子以形成環狀構造，而在此情形，Rs及/或尺4 在表觀上不會存在。又，Rg至Rl4中之任—係烴基而其 烴基可具有取代基。再者，如X爲2價或3價之雜原子時 ’則R 7及/或R 8將不存在。） 再者’本發明係由於提供—種經由使可以具有對應一 般式1或一般式2之R 1至只6之一般式5表示之化合物、 與可以具有對應一般式1或一般式2之X及R 7至R 1 4之 一般式6或一般式7之任1式表示之化合物反應之過程之 薰草素衍生物之製造方法，藉以解決前述課題者。 —般式5 :Printed by the Intellectual Property Office of the Ministry of Economic Affairs, the Consumers' Cooperatives (in the general formula 1 and the general formula 2, X represents a carbon atom or a hetero atom. R 1 to 1114 each independently represent a hydrogen atom or an appropriate substituent. However, R 1 and/ Or 112 may contain such a combined nitrogen atom and a carbon atom bonded by a ruler 3 or a ruler 4 to form a ring structure, and in this case, Rs and/or ruler 4 does not exist apparently. Any of Rl4 is a hydrocarbon group and its hydrocarbon group may have a substituent. Further, if X is a divalent or trivalent hetero atom, then R 7 and/or R 8 will not be present. By providing a compound represented by the general formula 5 which may have R 1 to 6 corresponding to the general formula 1 or the general formula 2, and X and R 7 to R 1 which may have the corresponding general formula 1 or general formula 2 A method for producing a humectin derivative in the process of reacting a compound represented by the general formula 6 or the general formula 7 of 4, in order to solve the above problems. - General 5:
本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） .裝-- (請先閱讀背面之注意事項再-填寫本頁) 訂 1311136 Α7 Β7 五、發明説明（5) 般式6 :This paper scale is applicable to China National Standard (CNS) A4 specification (210X 297 mm). Packing-- (Please read the note on the back and then fill out this page) Order 1311136 Α7 Β7 V. Invention description (5) General 6 :
-Ri。 、R”-Ri. , R"
R|〇 Rl1 (~般式6及一般式7中，如X係2價或3價之雜原 子時，則Η 1及Η 2將不會存在。） 一般式1或一般式2所示之薰草素衍生物均係文獻未 '經記載之新穎的有機化合物。本發明係基於新穎的有機化 合物之創製、及其產業上有用的性質所發現者。 裝-- (請先閱讀背面之注意事項再填寫本頁) 訂 經濟部智慧財產局8工消費合作社印製 發明之最佳實施形態 如就本發明之實施形態加以說明時，本發明有關一般 式1或一般式2所示之薰草素衍生物者。 $紙張尺度適财麵家標準（CNS ) A4規格（210X297公釐) -8- 1311136 A7 B7 五、發明説明（6) 一般式1 :R|〇Rl1 (In the general formula 6 and the general formula 7, if X is a divalent or trivalent hetero atom, then Η 1 and Η 2 will not exist.) General Formula 1 or General Formula 2 The xanthin derivatives are all novel organic compounds not described in the literature. The present invention is based on the discovery of novel organic compounds and their industrially useful properties.装-- (Please read the precautions on the back and fill out this page.) The best embodiment of the invention is printed by the Ministry of Economic Affairs, Intellectual Property Office, and the Consumers' Cooperatives. As described in the embodiments of the present invention, the present invention relates to the general formula. 1 or a herbicide derivative represented by the general formula 2. $ Paper Scale Appropriate Financial Standard (CNS) A4 Specification (210X297 mm) -8- 1311136 A7 B7 V. Description of Invention (6) General Formula 1:
(請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 一般式1及一般式2中，x表示破原子或雜原子。x 中之雜原子通常選擇氮原子、氧原子、硫原子、硒原子、 締原子等周期表中之第1 5族或第1 6.族之原子。此等碳 原子及雜原子之中’由於光特性及容易製造之關係’較佳 爲碳原子、氮原子' 氧原子以及硫原子。 一般式1及一般式2中之Ri至Ri4分別獨立表示氫 原子或適當之取代基。Rl至R 14中之取代基可例舉：甲 基、乙基、丙基、異丙基、異丙烯基、1 一丙烯基、2-丙嫌基、丁基、異丁基、第一丁基、第二丁基、2 - 丁烧 基、1 ，3 -丁二烯基、戊基、異戊基、新戊基、第三戊 基、1 一甲戊基、2_甲戊基、2 —戊烯基、己基、異己 本紙張尺度適用中國國家標隼（CNS ) A4規格（210X 297公釐） 1311136 A7 ._____B7_ 五、發明説明（7) (請先閲讀背面之注意事項再填寫本頁) 基、5 -甲己基、庚基、辛基、壬基、癸基、十一烷基、 十二烷基、十八烷基等之碳數2 0以下之脂肪族烴基、環 丙基、環丁基、環戊基、環己基、環己烯基、環庚基等之 脂環式烴基、苯基、鄰甲苯基、間甲苯基、對甲苯基、二 甲苯基、菜（mesityl)基、鄰異丙基（cumenyl)基、間異 丙苯基、對異丙苯基、苄基、苯乙（phenethyl )基、聯苯 基等之芳香族烴基、甲氧基、乙氧基、丙氧基、異丙氧基 、丁氧基、異丁氧基、第二丁氧基、第三丁氧基、戊氧基 、苯氧基、苄氧基等之醚基、甲氧羰基、乙氧羰基、丙氧 羰基、乙醯氧基、苯醯氧基等之酯基、氟基、氯基、溴基 、碘基等之鹵素基、羥基、羧基、氰基、硝基、再者，由 此等之組合而成之取代基。 經濟部智慧財產局員工消費合作社印製 雖因用途而異，唯只1至只2之取代基較佳爲脂肪族烴 基、脂環式烴基、芳香族烴基以及此等組合而成之烴基、 又，R 6中之取代基較佳爲例如：甲基、乙基、丙基、異丙 基、丁基、異丁基、第二丁基、第三丁基、戊基、異戊基 、新戊基、第三戊基等之短鏈長脂肪族烴基；甲氧基、乙 氧基、丙氧基、異丙氧基、丁氧基、異丁氧基、第三丁氧 基、戊氧基、苯氧基、苄氧基等之醚基；甲氧羰基、乙氧 羰基、丙氧羰基、乙醯氧基、苯醯氧基等之脂基；以及氰 基，在此等取代基中之氫原子之1個或複數個可以氟基等 之鹵素基所取代。R 9至R i 4中之取代基，如已述，係作 成爲其任一係脂肪族烴基、脂環式烴基、芳香族烴基或由 其等組合而成之烴基，此中較佳爲脂肪族烴基，特別是， -10- 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 1311136 A7 B7 經濟部智慧財產局員工消費合作社印製 五、發明説明（8) 異丙基、異丁基、第二丁基、第三丁基、異戊基、新戊基 、第三戊基、1—甲戊基、2 —甲戊基、異己基、5 —甲 己基等具有支鏈之碳數6以下者。R?及R8中之取代基較 佳爲111或尺2中同樣之脂肪族烴基、脂環式烴基、芳香族 烴基或由其等組合而成之烴基。但是，如X係如氮原子等 之3價原子時，則R 7或R 8之任一將不會存在，又，X係 氧原子、硫原子等之2價原子時，則R7、R8均將不會存 在。另外，如尺3及/或R4所結合之碳原子不構成<咯啶 環（julolidine ring)等之環狀構造時，則R3及/或R4作 成氫原子或按照甩途，從上述者中選擇適當者即可。又， Rs而言，因容易製造之關係，作成氫原子或羥基、或考慮 用途之下從上述之醚基及酯基選擇適當者。 如在重視光吸收能或發光能之用途方面，較佳爲 R 2均爲脂肪族烴基而此等將分別結合R 3或R 4所結合之 碳原子以形成《咯啶環而成之以一般式3或一般式4所示 之薰草素衍生物。一般式3及一般式4中，X係具一般式 1或一般式2時同樣，表示氫原子或適當的取代基，而R9 至R i 4之任一係烴基。R i 5至R i 8分別獨立表示氫原子 或脂肪族烴基，此中，較佳爲例如，甲基、乙基、丙基、 丁基、戊基等之短鏈長脂肪族烴基。一般式3或一般式所. 示薰草素衍生物中，R 9至R 1 4之任一如係例如，異丙基 、異丁基、第二丁基、第三丁基、異戊基、新戊基、第三 戊基、1 一甲戊基、2 —甲戊基、異己基、5 —甲己基等 之具有支鏈之脂肪族烴基者，由於不僅在通用之有機溶劑 (請先閲讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -11 - 1311136 A7 B7 五、發明説明（9) 中之溶解度及光吸收能、發光能優異、玻璃化溫度較高， 其結果，由於熱安定性高之故，有在不可避免高溫之環境 下’仍不易減弱光吸收能及發光能之特徵。 一般式3 :(Please read the notes on the back and fill out this page.) Printed by the Ministry of Economic Affairs, Intellectual Property Office, Staff Consumer Cooperatives In general formula 1 and general formula 2, x represents a broken atom or a hetero atom. The hetero atom in x is usually selected from a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, an atom, or the like, or a group of Group 1 or Group 6. Among these carbon atoms and hetero atoms, "the relationship between light characteristics and ease of production" is preferably a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom. Ri to Ri4 in the general formula 1 and the general formula 2 each independently represent a hydrogen atom or a suitable substituent. The substituent in R1 to R 14 may, for example, be methyl, ethyl, propyl, isopropyl, isopropenyl, 1-propenyl, 2-propenyl, butyl, isobutyl or first Base, second butyl, 2-butenyl, 1,3-butadienyl, pentyl, isopentyl, neopentyl, third amyl, 1-methylpentyl, 2-methylpentyl, 2 - Pentenyl, hexyl, and dissimilar papers are applicable to China National Standard (CNS) A4 specification (210X 297 mm) 1311136 A7 ._____B7_ V. Invention description (7) (Please read the notes on the back and fill in the form) An aliphatic hydrocarbon group having a carbon number of 20 or less, a cyclopropyl group, a 5-methylhexyl group, a heptyl group, an octyl group, a decyl group, a decyl group, an undecyl group, a dodecyl group, an octadecyl group or the like An alicyclic hydrocarbon group such as cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl or cycloheptyl, phenyl, o-tolyl, m-tolyl, p-tolyl, xylyl, mesityl An aromatic hydrocarbon group such as a cumenyl group, a m-cumyl group, a p-cumyl group, a benzyl group, a phenethyl group or a biphenyl group, a methoxy group, an ethoxy group, Propoxy, An isopropoxy group, a butoxy group, an isobutoxy group, a second butoxy group, a third butoxy group, a pentyloxy group, a phenoxy group, a benzyloxy group or the like, an oxycarbonyl group, an ethoxycarbonyl group, a halogen group such as a propoxycarbonyl group, an ethoxycarbonyl group or a benzoquinone group; a halogen group such as a fluorine group, a chlorine group, a bromine group or an iodine group; a hydroxyl group, a carboxyl group, a cyano group or a nitro group; a combination of substituents. Although the printing of the Intellectual Property Office of the Ministry of Economic Affairs is different for the purpose of use, only the substituents of 1 to 2 are preferably aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and the combination of these hydrocarbon groups. The substituent in R 6 is preferably, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, t-butyl, pentyl, isopentyl, new a short chain long aliphatic hydrocarbon group of a pentyl group, a third pentyl group or the like; a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a third butoxy group, a pentyloxy group An ether group of a benzyl group, a phenoxy group, a benzyloxy group or the like; an aliphatic group such as a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an ethoxylated group or a phenoxy group; and a cyano group in which the substituent is One or a plurality of hydrogen atoms may be substituted with a halogen group such as a fluorine group. The substituents in R 9 to R i 4 are as described above, and are any aliphatic hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group or a hydrocarbon group thereof, which is preferably a fat. Group of hydrocarbons, in particular, -10- This paper scale applies to China National Standard (CNS) A4 specification (210X297 mm) 1311136 A7 B7 Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperative printing 5, invention description (8) isopropyl, Isobutyl, t-butyl, tert-butyl, isopentyl, neopentyl, third amyl, 1-methylpentyl, 2-methylpentyl, isohexyl, 5-methylhexyl, etc. The number of carbons is less than or equal to 6. The substituent in R? and R8 is preferably an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group or a hydrocarbon group obtained by the combination of the same in 111 or 2. However, when X is a trivalent atom such as a nitrogen atom, either R 7 or R 8 will not be present, and when a divalent atom such as an X-based oxygen atom or a sulfur atom, R7 and R8 are both Will not exist. Further, when the carbon atom to which the caliper 3 and/or R4 are bonded does not constitute a ring structure such as a jullolidine ring, R3 and/or R4 may be a hydrogen atom or may be formed as described above. Just choose the right one. Further, Rs is preferably a hydrogen atom or a hydroxyl group due to ease of production, or is selected from the above-mentioned ether group and ester group in consideration of the use. For example, in the application of light absorption energy or luminescence energy, it is preferred that R 2 is an aliphatic hydrocarbon group and these will be bonded to the carbon atom to which R 3 or R 4 is bonded to form a "rhro ring". A xanthine derivative of the formula 3 or the general formula 4. In the general formula 3 and the general formula 4, the X system has a hydrogen atom or a suitable substituent in the same manner as in the general formula 1 or the general formula 2, and any one of R9 to R i 4 is a hydrocarbon group. R i 5 to R i 8 each independently represent a hydrogen atom or an aliphatic hydrocarbon group, and among them, a short-chain long aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, a butyl group or a pentyl group is preferable. In the case of the herbicide derivative, any one of R 9 to R 1 4 is, for example, an isopropyl group, an isobutyl group, a second butyl group, a tert-butyl group or an isopentyl group. , a neopentyl group, a third amyl group, a 1-methylpentyl group, a 2-methylpentyl group, an isohexyl group, a 5-methylhexyl group, etc., having a branched aliphatic hydrocarbon group, because not only in a general organic solvent (please Read the precautions on the back page and fill in this page. This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) -11 - 1311136 A7 B7 V. Solubility and light absorption energy, luminescence energy in the invention description (9) Excellent, high glass transition temperature, as a result of high thermal stability, it is not easy to reduce the characteristics of light absorption energy and luminescence energy in an environment of unavoidable high temperature. General formula 3:
(請先閱讀背面之注意事項再填寫本頁) -訂 經濟部智慧財產局g(工消費合作社印製 本發明之薰草素衍生物之具體例可例舉化學式1至化 學式2 7所示者。由於此等均在可視領域，詳細而言，波 長5 3 0 nm附近，通常4 5 Onm至6 0 0 nm具有吸 收極大値，且分子吸光係數亦大到1 X 1 〇 4以上，較佳爲 5 X 1 0 4以上之故，會高效率吸收如此波長域之可視光。 又，其多數在可視領域，詳細而言，波長5 8 Ο n m附近 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -12- 1311136 A7 _B7五、發明説明（1(J ，通常5 0 0 nm至6 5 0 nm具有螢光極大値等之發光 極大値，如予以激勵時，將發光綠黃色至赤色域之可視光 。以一般式1或一般式2所示之一群薰草素衍生物，如與 在來周知之類似化合物比較時，其玻璃化溫度係顯著性地 高，其多數爲超過1 3 Ot，如例如，化學式1 8所示之 薰草素衍生物可知，視取代基之情況而可達1 5 0 °C以上 。在此，本發明之薰草素衍生物之玻璃化溫度可依例如， 後述之通用之差示掃瞄熱量分析（以下簡稱「D S C分析 」）決定。 化學式1 : (請先閱讀背面之注意事項再填寫本頁)(Please read the precautions on the back and then fill out this page.) - The Ministry of Economic Affairs and Intellectual Property Office g (the industrial consumption cooperatives print the specific examples of the herbicide derivatives of the present invention, and the chemical formula 1 to the chemical formula 27 can be exemplified. Since these are all in the field of vision, in detail, near the wavelength of 530 nm, usually 4 5 Onm to 600 nm has an absorption maximum, and the molecular absorption coefficient is as large as 1 X 1 〇 4 or more, preferably. For more than 5 X 1 0 4, it will absorb the visible light in such a wavelength range with high efficiency. Moreover, most of them are in the field of vision. In detail, the paper scale is applicable to the Chinese National Standard (CNS) A4 near the wavelength of 5 8 Ο nm. Specification (210X297 mm) -12- 1311136 A7 _B7 V. Inventive Note (1 (J, usually 50,000 nm to 65 50 nm has a maximum luminescence of fluorescene, etc., if excited, it will illuminate green Visible light from the yellow to the red color range. The group of the oxaloquinone derivatives represented by the general formula 1 or the general formula 2 has a significantly higher glass transition temperature when compared with a similar compound which is conventionally known, and most of them are More than 1 3 Ot, such as, for example, the scented grass shown in Chemical Formula 18. The derivative of the present invention can be found to have a temperature of more than 150 ° C depending on the substituent. Here, the glass transition temperature of the herbicidal derivative of the present invention can be analyzed, for example, by a differential scanning calorimetry described later ( The following is referred to as "DSC Analysis".) Chemical Formula 1: (Please read the notes on the back and fill out this page)
經濟部智慧財產局員工消費合作社印製 化學式2 :Ministry of Economic Affairs, Intellectual Property Bureau, Staff Consumer Cooperative, Printing Chemical Formula 2:
本纸張尺度適用中國國家標準（CNS ) A4規格（2丨0X297公釐） -13- 1311136 A7 B7 五、發明説明（d 式 Φ- 化This paper scale applies to China National Standard (CNS) A4 specification (2丨0X297 mm) -13- 1311136 A7 B7 V. Invention description (d formula Φ-
H3CH3C
H2I 3C(H2I 3C (
-3 C (請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -14- 1311136 A7 B7 五、發明説明（〇 化學式5 :-3 C (Please read the note on the back and then fill out this page) Ministry of Economic Affairs Intellectual Property Bureau Staff Consumer Cooperative Printed Paper Size Applicable to China National Standard (CNS) A4 Specification (210X 297 mm) -14- 1311136 A7 B7 V. Description of the invention (〇Chemical Formula 5:
化學式6 :Chemical formula 6:
化學式7 : (請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製Chemical Formula 7: (Please read the notes on the back and fill out this page) Printed by the Ministry of Economic Affairs, Intellectual Property Bureau, Staff Consumer Cooperative
丨化學式8 : 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -15- 1311136 A7 B7 五、發明説明（j丨Chemical formula 8 : This paper scale applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) -15- 1311136 A7 B7 V. Invention description (j
化學式9 ··Chemical formula 9 ··
化學式10: (請先閱讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製Chemical Formula 10: (Please read the notes on the back and fill out this page) Printed by the Intellectual Property Office of the Ministry of Economic Affairs
化學式1 1 : 本纸張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） -16- 1311136 A7 B7 五、發明説明（4Chemical Formula 1 1 : This paper scale applies to Chinese National Standard (CNS) A4 specification (210 X 297 mm) -16- 1311136 A7 B7 V. Description of invention (4
(ch2)17ch3 化學式1 2 :(ch2)17ch3 Chemical Formula 1 2 :
(ch2)17ch3 (請先閱讀背面之注意事項再填寫本頁) 一裝·(ch2)17ch3 (Please read the notes on the back and fill out this page)
，1T 經濟部智慧財產局員工消費合作社印製 化學式1 3 : 本紙張尺度適用中國國家標準（CNS ) Α4規格（210 X 297公釐） -17- 1311136 A7 B7 五、發明説明（β, 1T Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperative printing Chemical formula 1 3 : This paper scale applies to China National Standard (CNS) Α 4 specifications (210 X 297 mm) -17- 1311136 A7 B7 V. Invention description (β
(請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 化學式1 4 :(Please read the notes on the back and fill out this page.) Printed by the Consumer Intellectual Property Office of the Ministry of Economic Affairs. Chemical Formula 1 4 :
化學式1 5 : 訂 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 1311136 A7 B7 五、發明説明（4Chemical Formula 1 5: The size of the paper is applicable to the Chinese National Standard (CNS) Α4 Specification (210X 297 mm) 1311136 A7 B7 V. Invention Description (4
本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 19- 1311136 A7 B7 五、發明説明（〇 經濟部智慧財產局員工消費合作社印製This paper scale applies to China National Standard (CNS) A4 specification (210X297 mm) 19- 1311136 A7 B7 V. Invention description (〇 Printed by the Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperative
—-------裝— (讀先閱讀背面之注意事項再填寫本頁) 訂 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -20- 1311136 A7 B7 五、發明説明（j 化學式2 0 :—-------Installation — (Read the first note on the back and fill out this page) The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) -20- 1311136 A7 B7 V. Invention Description (j Chemical Formula 2 0:
化學式Chemical formula
H3CH3C
CT (請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 化學式：2 本紙張尺度適用中國國家標準（CNS ) A4規格（210><297公釐） -21 - 1311136 A7 B7CT (please read the note on the back and then fill out this page) Ministry of Economic Affairs Intellectual Property Bureau Staff Consumer Cooperative Printed Chemical Formula: 2 This paper scale applies to China National Standard (CNS) A4 Specification (210><297 mm) -21 - 1311136 A7 B7
五、發明説明（JV. Description of the invention (J
化學式2 3 :Chemical formula 2 3 :
(請先閲讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 化學式2 4 : 式 ®·子 化(Please read the notes on the back and fill out this page.) Ministry of Economic Affairs, Intellectual Property Bureau, Staff Consumer Cooperatives, Printed Chemical Formula 2 4: Formula ®
本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） -22- 1311136 Μ Β7 五、發明説明（4This paper scale applies to China National Standard (CNS) A4 specification (210X 297 mm) -22- 1311136 Μ Β7 V. Invention description (4
化學式2 6:Chemical formula 2 6:
(ch2)3ch. 7 2 式 經濟部智慧財產局員工消費合作社印製 Η(ch2)3ch. 7 2 Type Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperative printing Η
(請先閱讀背面之注意事項再填寫本頁)(Please read the notes on the back and fill out this page)
本紙張尺度適用中國國家標準（CNS ) Α4規格（210 X 297公釐） -23- 1311136 A7 B7 五、發明説明（2) 本發明之薰草素衍生物’雖可以種種方法調製，惟如 注重經濟面時，則較佳爲經過使可以具有對應—般式1或 (請先閲讀背面之注意事項再填寫本頁) 一般式2之Ri至Re之一般式5表示之化合物、與可以具 有對應一般式1或一般式2之X及R7至Ri4之一般式6 或一般式7之任一式表示之化合物反應之過程之方法。在 此，一般式6及一般式7中，如X係2價或3價之雜原子 時，則Η 1及Η 2將不會存在。 一般式5 :This paper scale applies to China National Standard (CNS) Α4 specification (210 X 297 mm) -23- 1311136 A7 B7 V. Description of invention (2) The xanthene derivative of the present invention can be prepared by various methods, but In the case of an economical aspect, it is preferable to have a compound corresponding to the general formula 1 or (please read the back of the front and then fill in the page). The compound represented by the general formula 5 of Ri to Re of the general formula 2 may have a corresponding The method of the reaction of the compound of the general formula 1 or the general formula 2 and the general formula 6 of R7 to Ri4 or the formula of the general formula 7 is shown. Here, in the general formula 6 and the general formula 7, when X is a divalent or trivalent hetero atom, Η 1 and Η 2 will not be present. General formula 5:
一般式6 : R' /Re XH' R9General formula 6 : R' /Re XH' R9
經濟部智慧財產局員工消費合作社印製 亦即，反應容器中分別適量置入（通常等莫耳左右） 一般式5所示化合物’及一般式6或一般式7所示化合物 ’必要時溶解在適當溶劑中，添加例如，氫氧化鈉、氫氧 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -24- 1311136 A7 B7 五、發明説明（2么 (請先閲讀背面之注意事項再填寫本頁) 化鉀、碳酸鈉、碳酸鉀、碳酸氫鈉、乙酸鈉、氨、三乙胺 、口底陡、D比陡、11比略B定、苯胺、N，N _二甲苯胺、N ’ N —二乙苯胺等之鹽基性化合物；鹽酸、硫酸、硝酸、乙 酸、乙酸酐、三氟乙酸、對甲苯磺酸、甲磺酸、三氟甲磺 酸等之酸性化合物；氧化鋁、氯化鋅、四氯化錫' 四氯化 鈦等之路以士（ Lewis)酸性化合物等後，依加熱回流並在 加熱•攪拌中在周圍溫度下或較周圍溫度爲高的溫度下使 其反應。 溶劑可例舉：戊烷、己烷、環己烷、辛烷、苯、甲苯 、二甲苯等等烴類；四氯化碳、氯仿、1 ，2_二氯乙烷 、1 ，2 —二溴乙烷、三氯乙烯、四氯乙烯、氯苯、溴苯 、α -二氯苯等之鹵化物、甲醇、乙醇.、1 一丙醇、2-丙醇、1 一 丁醇、2 -丁醇、異丁醇、異戊醇、環己醇、 乙二醇、丙二醇、2 —甲氧乙醇、2 —乙氧乙醇、苯酚、 苄醇、甲酚、二乙二醇、三乙二醇、甘油等之醇類及酚類 ;二乙醚、二異丙醚、四氫呋喃、四氫吡喃、1 ，4 一二 嚼院、甲氧苯（anisole ) 、1 ，2 —二甲氧乙焼、1 ，2 經濟部智慧財產局員工消費合作社印製 一二甲氧基甲烷、二乙二醇二甲醚、二環己基_1 8 —冠 (crown ) - 6、甲基卡必醇、乙基卡必醇等之醚類；乙酸 、乙酸酐、二氯乙酸、三氟乙酸、無水丙酸、乙酸乙酯、 碳酸丁酯 '碳酸乙烯酯、碳酸丙烯酯 '甲醯胺、N 一甲基 甲醯胺、N，N —二甲基甲醯胺、N -甲基乙醯胺、n， N —•甲基乙釀肢、/、甲憐酸二|女醋' 碟酸三甲酯等之酸 及酸衍生物 '乙腈、丙腈、玻珀腈 '苄腈等之腈類；硝基 本紙張尺度適用中.國國家標準（CNS ) A4規格（210X 297公釐） -25- 經濟部智慧財產局員工消費合作社印製 1311136 A7 _ B7五、發明説明（2$ 甲烷、硝基苯等之硝基化合物；二甲亞硕、環丁硕等之含 硫化合物；水等，而必要時，可將此等適當組合使用。 如使用溶劑時’ ~般而言，溶劑量多時反應效率會下 降’反之’溶劑量少時將不易均勻加熱•攪拌而容易進行 副反應。因而，將溶劑量按重量比作成原料化合物全體之 1 0 0倍止’通常較佳爲5至5 0倍。難因原料化合物種 類或反應條件而有所不同，反應在1 〇小時以內，通常將 在0 · 5至5小時兀成。反應之進彳了可依例如，薄層色譜 法、氣相色譜法、高速液相色譜法等通用之方法監視。本 發明之薰草素衍生物可依本方法或準照本方法製造所需量 。在此，一般式5至一般式7所示化合物均可依調製類似 化合物用之通用之方法製得。 如此所得之薰草素衍生物，雖視用途而可直接反應混 合物使用，惟通常在使用之前可依例如，溶解、分液、傾 斜、過濾、萃取 '濃縮、薄層色譜法、氣相色譜法、高速 液相色譜法、蒸餾、昇華、結晶化等類似化合物之精製用 之方法精製’必要時，可採用組合此等方法。如將本發明 之薰草素衍生物作爲例如，色素雷射時之雷射作用物質使 用時，較佳爲在使用之前，依例如，蒸餾、結晶化及/或 昇華等方法予以高度精製。 此中，昇華係由於1次操作即可容易製得高純度之結 晶之外，因操作所發生之薰草素衍生物之損失少，且溶劑 不致於含雜在結晶中之故特別優異。所採用之昇華方法可 爲常壓昇華法亦可爲減壓昇華法，惟通常採用後者之減壓 (請先閲讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -26- 經濟部智慧財產局8工消費合作社印製 1311136 A7 B7五、發明説明（ 昇華法。爲減壓昇華本發明之薰草素衍生物時，例如，將 適量之薰草素衍生物裝入昇華精製裝置內，在保持裝置內 爲1 0 - 2托（Τ 〇 r r )以下之減壓，較佳爲1 〇 - 3托以 下中，按注意不使薰草素衍生物之方式，以融點以下之儘 量低之溫度加熱。供爲昇華精製之薰草素衍生物之純度較 低時，按注意不使不純物混入之方式，調整減壓度及加熱 溫度以控制昇華速度，又，薰草素衍生物不易昇華時，對 昇華精製裝置內通入稀有氣體等之情性氣體以促進昇華。 因昇華所得之結晶之大小可由昇華精製裝置內之凝縮面之 溫度之調整而可調節，如將凝縮面保持在較加熱溫度稍低 之溫度，並徐徐使其結晶化，則可獲較大之結晶。 如就本發明之薰草素衍生物之用途加以說明時，本發 明之薰草素衍生物，如已述，係由於在可視領域具有吸收 極大値且分子吸光係數亦大之故，由於使聚合性化合物曝 光在可視光，即可具有作爲進行聚合用之材料，使太陽電 池敏化用之材料、光學濾光器中之光吸收材料，再者，爲 染色各種衣服用之材料之多種多樣之用途。特別是，本發 明之多種薰草素衍生物，由於其吸收極大値波長，係接近 包括例如，氬離子雷射、氪離子雷射等之氣體雷射； c d S (硫化鎘）系雷射等之半導體雷射、分佈歸還型或 者布雷格（Brag )反射型ND — YAG雷射等在內之固體 雷射之波長5 0 0 nm附近，詳細而言，在4 5 0 nm至 5 5 0 n m具有振盪線之通用可視雷射光之振盪波長之故 ，由於對以如此可視雷射作爲曝光光源之光聚合性組成物 (請先閲讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -27- 1311136 Μ Β7 經濟部智慧財產局員工消費合作社印製 五、發明説明（2¾ 中作爲光敏化劑調配，即在傳真、影印機、印表機等之資 訊記錄之領域、及苯胺製版、凹版製版等之印刷之領域， 再者，在光阻（photo-resist)等之印刷電路之領域方面極 爲有利使用。 又，將本發明之薰草素衍生物，視必要，與吸收紫外 領域，可視領域及/或赤外領域之光之其他材料之1種或 複數種一起，用爲一般衣料或衣料以外之例如，摺綴裙、 緞帶、窗扉、印花布、威尼斯百葉簾、捲紗門、快閃門、 垂簾布、毛毯、綿被、綿被布、綿被蓋、床單、座墊、枕 頭、枕頭布、軟墊、墊子、地毯、睡袋、帳蓬 '汽車之內 裝材料、窗玻璃、窗戶玻璃等之建材寢室裝用品、鞋子之 中墊片、鞋子之內裝布、皮包布、包巾布、雨傘布、日傘 布、布娃娃、使用照明裝置或布老恩（Braun )管顯示器、 液晶顯示器'電漿顯示器等之資訊顯示裝置用之濾光器類 及螢幕類、太陽眼鏡、敞蓬車頂、微波爐、烤箱等之視窗 ，再者，包裝此等物品、塡充或收容用之包裝用材料、塡 充用材料、容器等時，不僅能防止或減少生物或物品方面 因自然光或人工光等之環境光所引起之障礙或不妥當事宜 ’尙有能調整物品之色度、色調、色彩、風味等，並調節 從物品所反射或所穿透之光爲所需之色平衡之實際利益。 再者，本發明之薰草素衍生物，係由於在可視領域具 有螢光極大値等之發光極大値，如予以激勵即會發出可視 光之故，作爲需要具備此種性質之有機化合物之例如，色 素雷射中之雷射作用物質方面亦有用。如將本發明之薰草 (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) Α4規格（210 X 2打公釐） -28- 1311136 A7 ______ B7__ 五、發明説明（d (請先閱讀背面之注意事項再填寫本頁) 素衍生物用爲色素雷射時，則按與構建周知之色素系雷射 振盪裝置時同樣方式進行精製，適當溶解在溶解中，必要 時’調整溶液之pH爲適當水準後封入雷射振盪裝置中之 色素室中。本發明之薰草素衍生物，如與周知之類似化合 物比較時，係不僅在可視領域中在極廣泛之波長域能獲得 放大增益，並且其耐熱性及耐光性高，而有即使長時間使 用’仍不易劣化之特徵。 本發明之薰草素衍生物之多數，如已述，係由於其玻 璃化溫度高，其結果，耐熱性高，即使在不可避免高溫之 環境中其光吸收能或發光能不易減弱之故，在所有之用途 中’因熱所引起之不妥當事宜較少而可極爲有利地使用。 以下，就本發明之實施形態，依據實施例加以說明。 實施例1 薰草素衍生物 經濟部智慧財產局員工消費合作社印製 取適量二甲基甲醯胺在反應容器中，添加化學式2 8 所示化合物〇 . 2 1 g及化學式29所示化合物0 . 2 1 g，在加熱回流下反應2小時後，冷卻反應混合物爲室溫 ，適當添加甲醇。採取所析出之結晶並使用氯仿/乙酸乙 酯混合液作爲展開溶液之柱色譜精製結果，製得化學式 1 8所示薰草素衍生物之橙色結晶〇 . 2 g。 化學式2 8 :Printed by the Intellectual Property Office of the Ministry of Economic Affairs, the consumer cooperatives, that is, the appropriate amount of the reaction container (usually waiting for the molars). The compound of the general formula 5 and the compound of the general formula 6 or the general formula 7 are dissolved in the In the appropriate solvent, add, for example, sodium hydroxide, hydrogen and oxygen. The paper scale applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) -24-1311136 A7 B7 V. Invention Description (2 (Please read the back of the note first) Please fill in this page again. Potassium, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium acetate, ammonia, triethylamine, steep bottom, D ratio steep, 11 ratio B, aniline, N, N dimethyl a salt-based compound such as aniline or N'N-diethylaniline; an acidic compound such as hydrochloric acid, sulfuric acid, nitric acid, acetic acid, acetic anhydride, trifluoroacetic acid, p-toluenesulfonic acid, methanesulfonic acid or trifluoromethanesulfonic acid; Alumina, zinc chloride, tin tetrachloride, titanium tetrachloride, etc., followed by a Lewis acid compound, etc., followed by heating under reflux and heating or stirring at ambient temperature or higher than ambient temperature Let it react. The solvent can be exemplified by: Hydrocarbons such as pentane, hexane, cyclohexane, octane, benzene, toluene, xylene, etc.; carbon tetrachloride, chloroform, 1,2-dichloroethane, 1,2-dibromoethane, three Halides of vinyl chloride, tetrachloroethylene, chlorobenzene, bromobenzene, α-dichlorobenzene, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, isobutylene Alcohol, isoamyl alcohol, cyclohexanol, ethylene glycol, propylene glycol, 2-methoxyethanol, 2-ethoxyethanol, phenol, benzyl alcohol, cresol, diethylene glycol, triethylene glycol, glycerol, etc. And phenols; diethyl ether, diisopropyl ether, tetrahydrofuran, tetrahydropyran, 1-4 chewing, anisole, 1-2 dimethoxine, 1, 2 Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperative printed monomethoxymethane, diethylene glycol dimethyl ether, dicyclohexyl_1 8 - crown - 6, methyl carbitol, ethyl carbitol, etc. Ethers; acetic acid, acetic anhydride, dichloroacetic acid, trifluoroacetic acid, anhydrous propionic acid, ethyl acetate, butyl carbonate 'ethylene carbonate, propylene carbonate 'formamide, N-methylformamide, N, N-dimethyl Acid and acid derivatives such as acetonitrile and N, methyl N-methyl acetamide, n, N - methyl ethyl broth, /, methyl dibenzoate | Nitrile, carbonitrile nitrile and other nitriles; nitro paper size applicable to national standard (CNS) A4 specification (210X 297 mm) -25- Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperative printing 1311136 A7 _ B7 V. Description of the invention (2$ nitro compounds such as methane and nitrobenzene; sulfur compounds such as dimethyl sulfoxide and cycline; water, etc., and if necessary, may be used in appropriate combination. In the case of a solvent, the reaction efficiency is lowered when the amount of the solvent is large. On the contrary, when the amount of the solvent is small, it is difficult to uniformly heat and stir, and the side reaction is easy. Therefore, the amount of the solvent is made to be 100% by weight of the total amount of the raw material compound, and usually 5 to 50 times. It is difficult to vary depending on the type of the starting compound or the reaction conditions, and the reaction is within 1 hour, usually at 0 to 5 to 5 hours. The progress of the reaction can be monitored by a general method such as thin layer chromatography, gas chromatography, or high performance liquid chromatography. The herbicidal derivatives of the present invention can be produced in the desired amount by this method or by the method. Here, the compounds of the general formula 5 to the general formula 7 can be produced by a general method for preparing a similar compound. The solanin derivative thus obtained may be directly used as a reaction mixture depending on the use, but usually, for example, dissolved, liquid, tilted, filtered, extracted, concentrated, thin-layer chromatography, gas chromatography, before use. , high-speed liquid chromatography, distillation, sublimation, crystallization, and the like are refined by a method of purification. When necessary, a combination of these methods may be employed. When the herbicide derivative of the present invention is used as, for example, a laser-acting substance for a pigment laser, it is preferably highly purified by, for example, distillation, crystallization, and/or sublimation before use. Among them, sublimation is easy to produce high-purity crystals by one operation, and the loss of the xanthin derivative due to the operation is small, and the solvent is not particularly excellent in containing impurities in the crystal. The sublimation method used may be the atmospheric pressure sublimation method or the decompression sublimation method, but the latter is usually decompressed (please read the back note and fill out this page). The paper scale applies to the Chinese National Standard (CNS) A4. Specification (210X297 mm) -26- Ministry of Economic Affairs Intellectual Property Bureau 8 Workers Consumption Cooperative Printed 1311136 A7 B7 V. Invention Description (Sublimation Law. For decompression and sublimation of the herbicide derivative of the present invention, for example, an appropriate amount The xanthanin derivative is charged into the sublimation refining device, and is decompressed to a pressure of 10 Torr to 2 Torr in the holding device, preferably 1 〇 - 3 Torr or less, according to the note that the oxacin is not taken. The method of derivatization is heated at a temperature as low as possible below the melting point. When the purity of the receptor derivative refined for sublimation is low, the degree of decompression and heating temperature are adjusted to control the manner in which impurities are not mixed. The speed of sublimation, in addition, when the xanthan derivatives are not easy to sublimate, the inert gas such as rare gas is introduced into the sublimation refining device to promote sublimation. The crystal obtained by sublimation can be condensed by the condensation surface in the sublimation refining device. It can be adjusted by adjusting the temperature. If the condensation surface is kept at a temperature slightly lower than the heating temperature and slowly crystallized, a larger crystal can be obtained. For the purpose of the use of the herbicidal derivative of the present invention In the case of the present, the xanthene derivative of the present invention has an absorption maximum in the visible field and a large molecular absorption coefficient, and since the polymerizable compound is exposed to visible light, it can be used for polymerization. The material, the material for sensitizing the solar cell, the light absorbing material in the optical filter, and the use of materials for dyeing various clothes. In particular, the various herbicidal derivatives of the present invention Because it absorbs the maximum erbium wavelength, it is close to a gas laser including, for example, an argon ion laser or a krypton ion laser; a semiconductor laser such as a cd S (cadmium sulfide)-based laser, a distributed reversion type, or a Breg ( Brag) Reflective ND—YAG laser and other solid lasers near the wavelength of 500 nm, in detail, the oscillation wavelength of the universal visible laser light with oscillating lines at 4500 to 550 nm For this reason, due to the photopolymerizable composition of such a visible laser as an exposure light source (please read the back of the page and then fill out this page). This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) - 27- 1311136 Μ Β7 Ministry of Economic Affairs, Intellectual Property Bureau, Staff Consumer Cooperatives, Printing 5, Invention Description (23⁄4 as a photosensitizer, ie in the field of information recording of fax, photocopying machine, printer, etc., and aniline plate making, gravure In the field of printing such as plate making, it is extremely advantageous in the field of printed circuits such as photo-resist, etc. Further, the xanthene derivative of the present invention can be visualized as needed, in the field of absorption ultraviolet rays. One or more of the other materials of the field and/or the light of the red field, used in addition to general clothing or clothing, for example, folded skirts, ribbons, window sills, printed fabrics, Venetian blinds, and shutter doors , flash door, curtain fabric, blanket, cotton quilt, cotton cloth, cotton cover, bed sheets, cushions, pillows, pillows, cushions, mats, carpets, sleeping bags, tents, interiors for cars Materials, window glass, window glass, etc., building materials, bedroom supplies, shoes, gaskets, shoes, cloth, cloth, towel, umbrella, umbrella, cloth doll, lighting device or cloth Braun) Filters for information display devices such as tube displays and liquid crystal displays, such as filters, screens for sunglasses, sunglasses, open tops, microwave ovens, ovens, etc., and packaging of such items, When packaging or containing packaging materials, filling materials, containers, etc., it can not only prevent or reduce obstacles or improper matters caused by ambient light such as natural light or artificial light in biological or articles. Chroma, hue, color, flavor, etc., and adjust the actual benefit of the desired color balance from the light reflected or penetrated by the item. Further, the xanthophyllin derivative of the present invention has a large amount of luminescence, such as a fluorescent luminescence in the visible field, and emits visible light when excited, for example, as an organic compound requiring such a property, for example. It is also useful for laser-acting substances in pigment lasers. If you are going to read the mowing grass of the present invention (please read the following notes on the back of the page) This paper scale applies to the Chinese National Standard (CNS) Α4 specification (210 X 2 mm) -28- 1311136 A7 ______ B7__ V. Invention (d (Please read the precautions on the back and fill in the page). When the pigment derivative is used as a pigment laser, it is purified in the same manner as in the construction of a well-known dye-based laser oscillating device, and is dissolved in the solution. If necessary, 'adjust the pH of the solution to a suitable level and then enclose it in the dye chamber in the laser oscillating device. The herbicide derivative of the present invention, when compared with a well-known compound, is not only widely used in the field of vision. The wavelength range can obtain an amplification gain, and its heat resistance and light resistance are high, and there is a feature that it is not easily deteriorated even if it is used for a long time. The majority of the xanthene derivatives of the present invention, as already described, are due to their glass transition temperature. High, as a result, the heat resistance is high, and even in the environment where the high temperature is unavoidable, the light absorption energy or the luminescence energy is not easily weakened, and it is inappropriate in all uses due to heat. It is preferable to use it in an extremely advantageous manner. Hereinafter, embodiments of the present invention will be described based on examples. Example 1 Kaempferol Derivatives Ministry of Economic Affairs Intellectual Property Bureau Staff Consumer Cooperative Printed an appropriate amount of dimethylformamidine The amine was added to a reaction vessel, and a compound of the formula 28 was added, 2 1 g of the compound of the formula 29, and 0.11 g of the compound of the formula 29, and the reaction mixture was cooled to reflux at room temperature for 2 hours, and methanol was appropriately added thereto. The precipitated crystal was used and the result of column chromatography purification using a chloroform/ethyl acetate mixture as a developing solution was used to obtain an orange crystal ruthenium of the oxacillin derivative represented by Chemical Formula 18. 2 g. Chemical Formula 2 8:
-29- 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 1311136 A7 B7 五、發明説明（2) 化學式2 9 :-29- This paper scale applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) 1311136 A7 B7 V. Invention description (2) Chemical formula 2 9 :
--------裝-- (請先閱讀背面之注意事項再填寫本頁) 採取結晶之一部分，依常法測定之結果，本例之薰草 素衍生物之融點爲3 4 5至3 5 1。(：。又，依常法測定氯 化乙烯溶液中之可視吸收色譜及螢光色譜之結果，分別在 波長4 9 1 nm及5 1 8 nm觀察到吸收極大値（ε = 5 · 8 X 1 〇 4 )及螢光極大値。再者，依常法測定氯仿一 d溶液中之1 Η -核磁共振譜之結果，化學位移 5 (Ppm，TMS)爲 1 · 37 (6Η， s)， 1 · 5 6 ( 9 Η > s )，1.62(6H，s)， 1.77乃至1.87(4H，m)， 3 · 3 Ο ( 2 Η > t ) > 3 . 3 9 ( 2 Η > s )， 7.40(1H，s)，7.67(lH，dd)， 7.73(lH，d)，7.90(lH，d)， 經濟部智慧財產局員工消費合作社印製 7·91 (lH，d) ，8.91 (lH，d)以及在 9 · 0 2 ( 1 H，s )之位置觀察到峰値。 在可視領域具有吸收極大値及螢光極大値之本例之薰 草素衍生物，係作爲光吸收劑、發光劑、在包括光化學性 聚合、太陽電池、光學濾光器、染色、色素雷射在內之各 種領域中有用者。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -30- 1311136 Α7 Β7 五、發明説明（2έ 實施例2 薰草素衍生物 除不用化學式2 8所示化合物而使用化學式3 0所示 者以外，其餘則準照實施例1之方法進行反應之結果，製 得化學式2 4所示之本發明之薰草素衍生物。 化學式3 0 :--------装-- (Please read the note on the back and then fill out this page) Take one part of the crystallization, according to the results of the usual method, the melting point of the herbicidal derivative of this example is 3 4 5 to 3 5 1. (:. Further, the results of visible absorption chromatography and fluorescence chromatography in the ethylene chloride solution were determined by the usual method, and the absorption maximum was observed at wavelengths of 4 1 1 nm and 5 18 nm, respectively (ε = 5 · 8 X 1 〇4) and the fluorescence is extremely large. Furthermore, the results of 1 Η-NMR of the chloroform-d solution are determined by the usual method, and the chemical shift 5 (Ppm, TMS) is 1 · 37 (6Η, s), 1 · 5 6 ( 9 Η > s ), 1.62 (6H, s), 1.77 or even 1.87 (4H, m), 3 · 3 Ο ( 2 Η > t ) > 3 . 3 9 ( 2 Η > s ), 7.40 (1H, s), 7.67 (lH, dd), 7.73 (lH, d), 7.90 (lH, d), Ministry of Economic Affairs, Intellectual Property Office, Staff Consumer Cooperative, Printed 7.91 (lH, d), 8.91 (lH,d) and peak 値 observed at the position of 9 · 0 2 ( 1 H, s ). In the visible field, there is a superabsorbent derivative of this example that absorbs extremely large 萤 and fluorescent ,, as light absorption. Agents, illuminants, useful in various fields including photochemical polymerization, solar cells, optical filters, dyeing, pigment lasers. This paper scale applies to China National Standard (CNS) A4 specification (210X297 mm) ) -30- 13111 36 Α7 Β7 V. DESCRIPTION OF THE INVENTION (2) Example 2 The carnosin derivative is obtained by the method of the first embodiment except that the compound of the formula 28 is not used, and the reaction is carried out according to the method of the first embodiment. The herbicidal derivative of the present invention represented by Chemical Formula 24 is obtained.
(錆先閱讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 在可視領域具有吸收極大値及螢光極大値之本例之薰 草素衍生物，係作爲光吸收劑、發光劑，在包括光化學性 聚合、太陽電池、光學濾光器、染色、色素雷射在內之各 種領域中有用者。 實施例3 薰草素衍生物 除不用化學2 8及化學式2 9所示化合物，而分別使 用化學式3 1及化學式3 2所示者以外，其餘則準照實施 例1之方法進行反應之結果，製得化學式1 2所示之本發 明之薰草素衍生物。 化學式3 1 :(Please read the note on the back and then fill out this page.) The Ministry of Economic Affairs, the Intellectual Property Office, and the Consumer Cooperatives, which prints the xanthine derivative in this field, which has great absorption and great fluorescence, is used as a light absorber. A luminescent agent is useful in various fields including photochemical polymerization, solar cells, optical filters, dyeing, and pigment lasers. Example 3 The xanthanin derivative was subjected to the reaction of the method of Example 1 except that the compound represented by Chemical Formula 2 and Chemical Formula 29 was not used, and the chemical formula 3 1 and the chemical formula 32 were respectively used. The herbicidal derivative of the present invention represented by Chemical Formula 1 is obtained. Chemical formula 3 1 :
本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公f ) -31 - [311136五、發明説明（y 化學式3 2 : A7 B7This paper scale applies to the Chinese National Standard (CNS) Α4 specification (210Χ297 public f) -31 - [311136 V. Invention Description (y Chemical Formula 3 2 : A7 B7
conh2 在可視領域具有吸收極大値及螢光極大値之本例之薰 草素衍生物，係作爲光吸收劑、發光劑，在包括光化學性 聚合、太陽電池、光學瀘光器、染色、色素雷射在內之各 種領域中有用者。 實施例4 薰草素衍生物 除不用化學式2 8及化學式2 9所示化合物，而分別 使用化學式3 3及化學式3 2所示者以外，其餘則準照實 施例1之方法進行反應之結果，製得化學式1 1所示之本 發明之薰草素衍生物。 化學式3 3 : (請先閱讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製Conh2 is a photoreceptor, a luminescent agent, which is a light absorbing agent, a luminescent agent, and includes a photochemical polymerization, a solar cell, an optical calender, a dye, and a pigment. Useful in various fields including lasers. Example 4 The xanthanin derivative was subjected to the reaction of the method of Example 1 except that the compound represented by the chemical formula 28 and the chemical formula 29 was not used, and the chemical formula 3 3 and the chemical formula 32 were respectively used. The herbicidal derivative of the present invention represented by Chemical Formula 1 is obtained. Chemical Formula 3 3 : (Please read the notes on the back and fill out this page) Printed by the Intellectual Property Office of the Ministry of Economic Affairs
在可視領域具有吸收極大値及螢光極大値之本例之薰 草素衍生物，係作爲光吸收劑、發光劑，在包括光化學性 聚合、太陽電池、光學濾光器、染色、色素雷射在內之各 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） -32 - 1311136 A7 ___—_B7 五、發明説明（ 種領域中有用者。 實施例5 薰草素衍生物 除不用化學式2 8及化學式2 9所示化合物，而分別 使用化學式3 4及化學式3 5所示者以外，其餘則準照實 施例1之方法進行反應之結果’製得化學式2所示之本發 明之薰草素衍生物。 化學式3 4 :In this field of vision, the herbicidal derivative of this example, which absorbs extremely large amounts of strontium and fluorescence, is used as a light absorbing agent and luminescent agent, including photochemical polymerization, solar cells, optical filters, dyeing, and dye thunder. The size of each paper used in the shot is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) -32 - 1311136 A7 _____B7 V. Description of the invention (useful in the field. Example 5: The present invention, which is represented by the chemical formula 2, is obtained by using the compound of the chemical formula 28 and the chemical formula 29, and the results of the reaction of the method of the first embodiment are carried out except that the chemical formula 34 and the chemical formula 35 are respectively used. The herbicide derivative. Chemical formula 3 4 :
化學式3 5 :Chemical formula 3 5 :
ch2ch3 C〇NH2 經濟部智慧財產局員工消費合作社印製 在可視領域具有吸收極大値及螢光極大値之本例之薰 草素衍生物，係作爲光吸收劑、發光劑，在包括光化學性 聚合、太陽電池、光學濾光器、染色、色素雷射在內之各 種領域中有用者。 實施例6 薰草素衍生物 將依實施例1至實施例5之方法所得之5種薰草素衍 -33- (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） 1311136 A7 ____B7 五、發明説明（3) 生物中之一種裝入水冷式昇華精製裝置內，依常法在保持 裝置內爲減壓之下加熱，以分別進行昇華精製。 (請先閲讀背面之注意事項再填寫本頁) 本例之薰草素衍生物均可在需要具有光吸收能、發光 能之高純度之有機化合物之各種領域中有利使用。 在此，本發明之薰草素衍生物，係雖因構造而給飼條 件或收率有若干差異，惟包括例如，上述以外之化學式1 至化學式2 7所示者在內，均可依實施例1至實施例6之 方法、或者準照其等方法製造所需量。 其次，就關於本發明之薰草素衍生物之玻璃化溫度、 光敏化能所進行之實驗加以說明。 實驗例1 薰草素衍生物之玻璃化溫度 經濟部智慧財產局員工消費合作社印製 就實施例1之方法所得之化學式1 8所示薰草素衍生 物’使用市售之DSC分析裝置（商品名「DSC220 U型」，精工儀器<股>製造），依常法進行DSC分析 之結果，在1 5 1 °C觀察到玻璃化溫度。同時並行就在萘 噻唑環中不具有烴基之化學式3 6所示周知之類似化合物 ’同樣方式測定玻璃化溫度之結果，爲1 2 9 t。另外， 化學式3 6所示之周知之類似化合物，如與化學式1 8所 示之本發明之薰草素衍生物比較時，係雖在丙酮、氯仿等 之有機溶劑中之溶解度顯著性地小，惟在化學式1 8所示 之與本發明之薰草素衍生物同樣之波長域顯示有吸收極大 値及發光極大値。 -34- 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 1311136 A7 ____ B7 五、發明説明（d 化學式3 6 :Ch2ch3 C〇NH2 Ministry of Economic Affairs, Intellectual Property Bureau, Staff and Consumers Cooperative, printed in this field of view, has a great absorption of sputum and fluorescent sputum. This is a light absorbing agent and a luminescent agent, including photochemical properties. It is useful in various fields such as polymerization, solar cells, optical filters, dyeing, and pigment lasers. Example 6 Kaempferol Derivatives The five kinds of Kaempferol-L-33 obtained by the methods of Examples 1 to 5 (please read the back of the note first and then fill in this page) This paper scale applies to Chinese national standards. (CNS) A4 size (210 X 297 mm) 1311136 A7 ____B7 V. Description of invention (3) One of the organisms is placed in a water-cooled sublimation refining device, which is heated under reduced pressure in the holding device according to the usual method. Sublimation purification is carried out separately. (Please read the precautions on the back and fill out this page.) The xanthene derivatives of this example can be advantageously used in various fields where high purity organic compounds having light absorbing energy and luminescent energy are required. Here, the kaempferol derivative of the present invention may have a slight difference in feeding conditions or yield due to the structure, and may include, for example, those represented by Chemical Formula 1 to Chemical Formula 27 other than the above. The required amounts were produced by the methods of Examples 1 to 6, or by the methods thereof. Next, an experiment conducted on the glass transition temperature and photosensitization energy of the kaempferol derivative of the present invention will be described. Experimental Example 1 Glassy Temperature of Kaempferol Derivatives Ministry of Commerce, Intellectual Property Office, Employees' Consumption Co., Ltd. Printed on the method of Example 1, the chemical derivative of the formula 1 is shown using a commercially available DSC analyzer (commodity The name "DSC220 U type", Seiko Instruments & Co., Ltd.) was subjected to DSC analysis according to the usual method, and the glass transition temperature was observed at 15 ° C. Simultaneously, in the same manner as in the case where the similar compound shown by the chemical formula 36 having no hydrocarbon group in the naphthothiazole ring was used, the glass transition temperature was measured, and it was 1 2 9 t. Further, a well-known compound represented by Chemical Formula 36 is significantly less soluble in an organic solvent such as acetone or chloroform when compared with the herbicidal derivative of the present invention represented by Chemical Formula 18. However, the wavelength range shown in Chemical Formula 18 which is the same as the herbicide derivative of the present invention shows an absorption maximum and a maximum luminescence. -34- This paper scale applies to Chinese National Standard (CNS) A4 specification (210X297 mm) 1311136 A7 ____ B7 V. Description of invention (d Chemical Formula 3 6 :
(請先閲讀背面之注意事項再填寫本頁) 如所周知，玻璃化溫度係推測有機化合物之熱安定性 用之重要指標之一，而如係玻璃化溫度愈高，則被認爲熱 安定性較佳者。上述之實驗結果表示，在分子內具有結合 1個或複數個烴基而成之縮合莱環之本發明之薰草素衍生 物，係不致於實質上影響周知之類似化合物之良好光特性 之下，能顯著改善耐熱性者。 實驗例2 薰草素衍生物之光敏化能 經濟部智慧財產局員工消費合作社印製 依常法，對乙基溶纖劑9 0 0重量份中，分別調配作 爲光聚合性單體之異戊四醇丙烯酸酯1 0 0重量份，作爲 粘合劑樹脂之丙烯酸-甲基丙烯酸共聚物1 0 0重量份， 作爲聚合引發劑之3，3’ ，4，4， 一四（第三丁基過 羰基）二苯甲酮8重量份，再者，作爲光敏化劑調配依實 施例1之方法所得之化學式1 8所示之本發明之薰草素衍 生物6重量份，以調製光聚合性組成物。 依常法，將此組成物均勻塗佈在經表面處理之糙面鋁 板上以形成感光層後，爲防止因氧氣所引起之聚合阻礙而 -35- 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇χ 297公釐） 1311136 A7 B7 五、發明説明（ (請先閱讀背面之注意事項再填寫本頁) 在感光層表面形成聚乙烯醇層。對此感光層密貼灰度測試 卡（gray scale )以設置3 K W超高壓水銀燈，並照射組合 銳截止式濾波器（sharp cut off filter )(商品名「Y 4 7」 及「Y 5 2」，東芝玻璃 < 股 > 製），干涉濾光片（ interference filter)(商品名「KL49」及「KL54」 ’東芝玻璃 < 股 > 製）及熱線截止濾光器（商品名「 HA3 0」保谷 <股> 製）所得之波長5 32 nm (相當 於N d - Y A G雷射之第二高次諧波）之可視光。然後， 依常法使用鹼系顯像液進行顯像後，對「數1」所示之數 式中分別代入步驟標示（step tablet )第η段之穿透率Tn 、曝光時間t及曝光強度I。，並從經光固化之段數計算敏 感度之結果，供爲試驗之光聚合性組成物之敏感度爲 0 · 1 m J / c m 2。作爲對照，就除經省略薰草素衍生物 以外其餘則與上述者同樣方式所調製之組成物，同樣進行 光照射，惟因聚合所引起之固化，則完全未被觀察到。 化學式3 7 : 〔數1〕 經濟部智慧財產局員工消費合作杜印製 E(mJ/cm2)=l〇(mJ/cm2 ♦ s)x Tnx t(s) 此等實驗結果，係在表示在光化學性聚合中，本發明 之薰草素衍生物可作爲能敏化聚合性化合物或聚合引發劑 之材料而有用之事實。 產業上利用之可能性 如上所說明，本發明係基於新穎的有機化合物之創製 -36- 本紙張尺度適用中國國家標準（CNS ) Μ規格（210X297公釐） 1311136 A7 B7 五、發明説明（3) 、及其產業上有用的性質之發現者。本發明之薰草素衍生 物，係由於在可視領域具有吸收極大値’且其分子吸光係 數亦大之故，可作爲光吸收劑而在光化學性聚合' 太陽電 池、光學濾光器、染色等之領域有利使用。再者’本發明 之薰草素衍生物，係由於在可視領域具有發光極大値，如 被激勵時會發出可視光之故，可作爲發光劑而在色素雷射 等之領域有利使用。本發明之薰草素衍生物之多數，係玻 璃化溫度高，其結果，耐熱性較高之故，即使在不可避免 高溫之環境下仍然不易減弱光吸收能、發光能。 如此有用之薰草素衍生物，係可由經過使具有特定之 原子團之苯酚化合物、與具有特定之原子團之萘胺化合物 反應之過程之本發明之製造方法而製得所需量。 可發揮如此顯著的效果之本發明，係可謂對業界之貢 獻極大且爲有意義的發明。 (請先閲讀背面之注意事項再填寫本頁) _裝-(Please read the notes on the back and fill out this page.) As is known, the glass transition temperature is one of the important indicators for predicting the thermal stability of organic compounds. If the glass transition temperature is higher, it is considered to be heat stable. Better sex. The above experimental results show that the herbicidal derivative of the present invention having a condensed ring which is bonded to one or a plurality of hydrocarbon groups in the molecule does not substantially affect the good light characteristics of a well-known compound. Can significantly improve heat resistance. Experimental Example 2 Photosensitive Energy of the Kaempferol Derivatives The Department of Intellectual Property of the Intellectual Property Office of the Ministry of Economic Affairs printed the usual method, and prepared the isoflavone as a photopolymerizable monomer in 900 parts by weight of ethyl cellosolve. 100 parts by weight of tetraol acrylate, 100 parts by weight of an acrylic acid-methacrylic acid copolymer as a binder resin, 3,3', 4, 4, and a tetrabutyl group as a polymerization initiator 8 parts by weight of carbonyl)benzophenone, and 6 parts by weight of the herbicidal derivative of the present invention represented by Chemical Formula 18 obtained by the method of Example 1 as a photosensitizer to prepare photopolymerizability Composition. According to the usual method, the composition is uniformly coated on the surface-treated matte aluminum plate to form a photosensitive layer, in order to prevent polymerization inhibition caused by oxygen. -35- The paper scale is applicable to the Chinese National Standard (CNS) A4. Specifications (21〇χ 297 mm) 1311136 A7 B7 V. Description of the invention ((Please read the note on the back and fill out this page) Form a layer of polyvinyl alcohol on the surface of the photosensitive layer. (gray scale) to set a 3 KW ultra-high pressure mercury lamp, and to illuminate a combination of sharp cut off filters (trade names "Y 4 7" and "Y 5 2", Toshiba Glass < Shares>) , interference filter (trade name "KL49" and "KL54" 'Toshiba glass < stock>) and hot line cut-off filter (trade name "HA3 0" Baogu < stock> system) The visible light of the wavelength of 5 32 nm (corresponding to the second harmonic of the N d -YAG laser) is then visualized by the usual method using an alkali-based developing solution, as shown by "number 1" Substituting the step number (step tablet) into the nth paragraph The transmittance Tn, the exposure time t, and the exposure intensity I, and the sensitivity of the photopolymerizable composition from the photocured segment was 0. 1 m J / cm 2 as a result of the sensitivity calculation. In the same manner, the composition prepared in the same manner as the above was subjected to light irradiation except for the ophedrine derivative, but the curing due to polymerization was not observed at all. Chemical Formula 3 7 : Number 1] Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperation Du printing E (mJ/cm2) = l〇 (mJ/cm2 ♦ s) x Tnx t(s) These experimental results are expressed in photochemical polymerization The present invention is useful as a material capable of sensitizing a polymerizable compound or a polymerization initiator. The possibility of industrial use is as described above, and the present invention is based on the creation of a novel organic compound-36 - This paper scale applies to Chinese National Standard (CNS) Μ Specifications (210X297 mm) 1311136 A7 B7 V. Inventive Note (3), and discoverers of its industrially useful properties. The herbicidal derivatives of the present invention are Due to the suction in the visual field It is extremely large and has a large molecular absorption coefficient. It can be used as a light absorber in the field of photochemical polymerization, such as solar cells, optical filters, dyeing, etc. Further, the present invention is derived from the herbicidal agent. The object has a great luminescence in the visible field, and emits visible light when excited. It can be used as a luminescent agent in the field of dye laser or the like. Most of the xanthin derivatives of the present invention have a high glass transition temperature, and as a result, the heat resistance is high, and the light absorption energy and the luminescence energy are not easily attenuated even in an environment where high temperature is unavoidable. Such a useful herbicide derivative can be obtained by a production method of the present invention which is a process of reacting a phenol compound having a specific atomic group with a naphthylamine compound having a specific atomic group. The present invention, which can exert such remarkable effects, is an invention that is of great interest to the industry. (Please read the notes on the back and fill out this page) _装-
、1T 經濟部智慧財產局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS )八4規格（210X297公釐） -37 -1T Ministry of Economic Affairs Intellectual Property Bureau employee consumption cooperative printing This paper scale applies China National Standard (CNS) eight 4 specifications (210X297 mm) -37 -
Claims (1)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001124524 | 2001-04-23 | ||
| JP2002018418A JP4202025B2 (en) | 2001-04-23 | 2002-01-28 | Coumarin derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI311136B true TWI311136B (en) | 2009-06-21 |
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ID=26614008
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| Application Number | Title | Priority Date | Filing Date |
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| TW091108371A TWI311136B (en) | 2001-04-23 | 2002-04-23 |
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| Country | Link |
|---|---|
| JP (1) | JP4202025B2 (en) |
| KR (1) | KR100951788B1 (en) |
| TW (1) | TWI311136B (en) |
| WO (1) | WO2002088116A1 (en) |
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| CN104128116B (en) * | 2014-08-08 | 2016-08-24 | 长兴华强电子有限公司 | A kind of vapour-pressure type lifting device of vacuum stirring bucket |
| CN114133387B (en) * | 2021-11-29 | 2023-04-07 | 郑州大学 | Fluorescent probe with viscosity sensing property and capable of targeting multiple organelles |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2411969A1 (en) * | 1974-03-13 | 1975-09-25 | Bayer Ag | DYE LASER |
| KR0131427B1 (en) * | 1994-06-30 | 1998-04-11 | 성재갑 | Cosmetic cases indicating uv intensity for user |
| JPH08334898A (en) * | 1995-04-07 | 1996-12-17 | Konica Corp | Photopolymerizable composition and image forming method using the same |
| JPH1010714A (en) * | 1996-06-21 | 1998-01-16 | Konica Corp | Photosensitive composition |
| US6573380B2 (en) * | 1999-03-09 | 2003-06-03 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | 4-cyanocoumarin derivatives and uses thereof |
-
2002
- 2002-01-28 JP JP2002018418A patent/JP4202025B2/en not_active Expired - Fee Related
- 2002-04-23 TW TW091108371A patent/TWI311136B/zh not_active IP Right Cessation
- 2002-04-23 WO PCT/JP2002/004043 patent/WO2002088116A1/en active Application Filing
- 2002-04-23 KR KR1020027017582A patent/KR100951788B1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002088116A1 (en) | 2002-11-07 |
| KR100951788B1 (en) | 2010-04-07 |
| JP4202025B2 (en) | 2008-12-24 |
| JP2003012669A (en) | 2003-01-15 |
| KR20040000300A (en) | 2004-01-03 |
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