TW201036941A

TW201036941A - Method for producing sulfonamide compound

Info

Publication number: TW201036941A
Application number: TW99107692A
Authority: TW
Inventors: yasuki Tatsumi
Original assignee: Sumitomo Chemical Co
Priority date: 2009-03-30
Filing date: 2010-03-16
Publication date: 2010-10-16
Also published as: JP5732200B2; CN101851224A; KR101668339B1; JP2010254965A; KR20100109437A

Abstract

The invention provides a method for producing a sulfonamide compound. The method comprises the following steps: a first step of sulfonamidating at least one compound selected from a group consisting of - SO.sub.3.sup.- and - SO.sub.3.H; a second step of rinsing the reactant obtained by the first step utilizing at least one selected from a group consisting of acidic aqueous solution and water above 60 degrees Celsius to below 95 degrees Celsius; and a third step of drying the rinsed article obtained by the second step so as to acquire the sulfonamide compound.

Description

201036941 六、發明說明：【發明所屬之技術領域】本發明係關於一種磺醯胺化合物之製造方法。【先前技術】自先前以來，為製造具備所期望之分光特性，較薄且微細之著色圖案，例如製造有各種磺醯胺化合物（例如專利文獻1)。於此種磺醯胺化合物之製造中通常使用水進行主洗。但是，使用包含藉由此種方法所製造之磺醯胺化合物之組合物形成塗膜時，存在所形成之塗膜中產生異物之情形。 [專利文獻1]曰本專利特開2003-2014 13號公報【發明内容】本發明之目的在於提供一種磺醯胺化合物之製造方法，其可用於形成異物之產生減少之塗膜的組合物。即，本發明係提供以下之[丨]〜[6]者。 [1 ]. 一種磺醯胺化合物之製造方法，其包括·· 第1步驟，將具有選自由_8〇3-及_s〇3H所組成群中之至少一種的化合物續醯胺化；第2步驟，至少利用選自由酸性水溶液及6〇。〇以上、 95 C以下之水所組成群中的至少一種清洗第i步驟中所獲得之反應物；及第3步驟，使第2步驟中所獲得之清洗物乾燥而獲得磺醯胺化合物。 146960.doc 201036941 [2] _如Π]之磺醯胺化合物之製造方法，纟中酸性水溶液係pH值為5以下之酸性水溶液。 [3] ·如[1]或[2]之磺醯胺化合物之製造方法，其中酸性水溶液係選自由鹽酸水錢及乙酸水溶液所組成群中之至少一種。 [4] ·如[1]至[3]t任-項之績醯胺化合物之製造方法，1 :具有選自由_S〇3.及·δ〇3Η所組成群中之至少—種基的: 口物係包含咄ρ星骨架之化合物。 [5] ·如⑴至[4]_任—項之績醯胺化合物之製造方法立 :具有選自由-SCV及·S〇3H所組成群中之/匕合物係式⑴所^化合物：種基的化 R1201036941 VI. Description of the Invention: [Technical Field to Which the Invention Is Ascribed] The present invention relates to a method for producing a sulfonamide compound. [Prior Art] For the purpose of producing a thinner and finer colored pattern having desired spectral characteristics, for example, various sulfonamide compounds have been produced (for example, Patent Document 1). In the manufacture of such sulfonamide compounds, water is usually used for main washing. However, when a coating film is formed using a composition containing a sulfonamide compound produced by such a method, foreign matter is generated in the formed coating film. [Patent Document 1] JP-A-2003-2014 13 SUMMARY OF THE INVENTION An object of the present invention is to provide a method for producing a sulfonamide compound which can be used for a composition for forming a coating film having reduced foreign matter generation. That is, the present invention provides the following [丨]~[6]. [1]. A method for producing a sulfonamide compound, comprising: a first step of continuously amidating a compound having at least one selected from the group consisting of _8〇3- and _s〇3H; The second step is at least selected from the group consisting of an acidic aqueous solution and 6 Torr. At least one of the above-mentioned groups of waters of 95 C or less is used to clean the reactant obtained in the i-th step; and in the third step, the washing material obtained in the second step is dried to obtain a sulfonamide compound. 146960.doc 201036941 [2] A method for producing a sulfonamide compound, wherein the acidic aqueous solution of hydrazine is an acidic aqueous solution having a pH of 5 or less. [3] The method for producing a sulfonamide compound according to [1] or [2], wherein the acidic aqueous solution is at least one selected from the group consisting of hydrochloric acid and aqueous acetic acid. [4] The method for producing a guanamine compound as described in [1] to [3] t-, and having at least one selected from the group consisting of _S〇3. and δ〇3Η : The oral system contains a compound of the 星ρ star skeleton. [5] The method for producing a guanamine compound according to (1) to [4] _ any one of the formula: having a compound selected from the group consisting of -SCV and ·S〇3H, and a compound of the formula (1): Kind of R1

(式（丨1)中，Rl〜Rl5分別獨立表示氫原子、Rl6 -〇R、c〇2h、_c〇2R16、s〇原…、，、 -S03H，XRl 丨5 3 ' -S〇3Na ^ -S〇3Ki(In the formula (丨1), R1 to Rl5 independently represent a hydrogen atom, Rl6 - 〇R, c〇2h, _c〇2R16, s〇原...,, -S03H, XRl 丨5 3 ' -S〇3Na ^ -S〇3Ki

Rl6表二〜R中之—者表示_SCV’ 所包含之7^數為1〜1〇之一價之飽和煙基’該餘和烴基寺氧基取代/㈣由_素料、㈣或碳數為1〜1〇之搞、侃或_=飽#嗜基中所包含之偶·亦可取代成-〇 R17表示t 氧原子或碳數為i〜10之—價之飽和烴基）。 146960.doc 201036941 [6]· —種著色組合物之製造方法，其包括：第1步驟’將具有選自由-SO3-及_s〇3h*組成群中之至少一種基的化合物磺醯胺化；第2步驟，至少利用選自由酸性水溶液及6〇t以上、 95°C以下之水所組成群中的至少一種清洗第i步驟中所獲得之反應物；第3步驟，使第2步驟中所獲得之清洗物乾燥而獲得磺醯 ^ 胺化合物；及〇第4步驟’將第3步驟中所獲得之石黃酿胺化合物與選自由顏料或顏料分散液（B)、溶劑（c)、樹脂（D)、光聚合性化合物（E)以及光聚合起始劑所組成群中之至少一種混合。【實施方式】 13 本發明之磺醯胺化合物之製造方法係包括如下步驟而成：第1步驟，將具有選自由-SCV及-S〇3H所組成群中之至 0少-種基的化合物（以下，有時稱為「續酸化合物」）石黃酿胺化；第2步驟，至少利用選自 95°C以下之水所組成群中的得之反應物；及由酸性水溶液及6〇t以上、至少一種清洗第1步驟中所獲中所獲传之清洗物乾燥而獲得續醯第3步驟，使第2步驟胺化合物。 (第1步驟）所謂磺醯胺化係指將化合物所具有之-so3_及-S03H之 146960.doc 201036941 至少一種變成取代胺績醯基的反應。作為本發明之磺醯胺化合物，較好的是具有N-單取代胺績醯基及N，N-二取代胺磺醯基之化合物。首先，為製造磺醯胺化合物，而準備具有-so3·及-so3h 之至少一種之化合物。作為此種化合物，只要為具有-S03·及-S03H之至少一種之化合物則並無特別限定，較好的是包含咄蠖骨架之化合物。其中’較好的是式（1)(以下，有時稱為「磺酸化合物 (1)」或「化合物（1)」）所示之化合物：Rl6 in Table 2~R-- means that _SCV' contains 7^1 饱和1 〇之饱和 ' ' 该该该该该该该该该该 ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' The number of 1~1〇, 侃 or _=满# may be replaced by -〇R17 represents a t-oxygen atom or a saturated hydrocarbon group having a carbon number of i~10. 146960.doc 201036941 [6] The method for producing a coloring composition, comprising: the first step 'sulfonating a compound having at least one selected from the group consisting of -SO3- and _s〇3h* In the second step, at least one of the reactants obtained in the i-th step is cleaned by at least one selected from the group consisting of an acidic aqueous solution and a water of 6 〇t or more and 95 ° C or less; and the third step is performed in the second step. The obtained washing product is dried to obtain a sulfonamide compound; and the fourth step 'the step of obtaining the scutellite compound obtained in the third step from the pigment or pigment dispersion (B), the solvent (c), At least one of the group consisting of the resin (D), the photopolymerizable compound (E), and the photopolymerization initiator is mixed. [Embodiment] 13 The method for producing a sulfonamide compound of the present invention comprises the following steps: In the first step, a compound having a group selected from the group consisting of -SCV and -S〇3H to 0-group is used. (hereinafter, sometimes referred to as "continued acid compound"), alkalization, and a second step, using at least a reactant selected from the group consisting of water below 95 ° C; and an acidic aqueous solution and 6 〇 The above-mentioned, at least one cleaning of the washing material obtained in the first step is dried to obtain the third step, and the second step is the amine compound. (Step 1) The term "sulfonylation" refers to a reaction in which at least one of 146960.doc 201036941 of -so3_ and -S03H of the compound is changed to a substituted amine group. As the sulfonamide compound of the present invention, a compound having an N-monosubstituted amine fluorenyl group and an N,N-disubstituted amine sulfonyl group is preferred. First, a compound having at least one of -so3· and -so3h is prepared for the production of a sulfonamide compound. The compound is not particularly limited as long as it has at least one of -S03· and -S03H, and a compound containing an anthracene skeleton is preferred. Among them, preferred is a compound represented by the formula (1) (hereinafter, sometimes referred to as "sulfonic acid compound (1)" or "compound (1)"):

(式⑴中， RLR15分別獨立表示氫原子、_R16、_〇H、_〇Rl6、_c〇2H、 -co2R16、-so3-、-S〇3Na、_s〇3K或-S03H，且R1〜R15 中之一者表示-S03-; R16表示碳數為1〜10之一價之飽和烴基，該飽和烴基中所包含之氫原子亦可由_素原子、羥基或碳數為丨〜10之烷氧基取代，該飽和烴基中所包含之_CH2_亦可取代成_0_、 -CO-或-NR17-; R17表示氫原子或碳數為i〜1〇之一價之飽和烴基）。 146960.doc 201036941 再者，於式（1)令，化合物中之正（+)電荷數與負㈠電荷數相同。其中，飽和烴基亦可為烷基、環烷基'將該等取代基任 . 意組合而成之具有烷基之環烷基及具有環烷基之烷基。 . 作為烷基，可列舉：甲基、乙基、丙基、異丙基、丁基、異丁基、戊基、己基、庚基、辛基、卜甲基丙基、甲基丙基、1-甲基丁基、2·甲基丁基、3_甲基丁基、2_乙 ◎ 基己基、壬基、癸基、1，1_二甲基丙基、ι，2-二甲基丙基、2,2-二甲基丙基等。作為環烧基，可列舉：環丙基、環丁基、環戊基、環己基、環庚基、環辛基、三環癸基等。作為#素原子’可列舉：氟原子、氯原子、溴原子等。作為烧氧基，可列舉：甲氧基、乙氧基、丙氧基、異丙氧基、丁氧基、1-甲基丙氧基、2_甲基丙氧基、第三丁氧基' 1-甲基丁氧基、2-甲基丁氧基、3_甲基丁氧基、u_ 〇三曱基丙氧基、i，2-二甲基丙氧基、2,2-二甲基丙氧基、正戊氧基、正己氧基、庚氧基、辛氧基、2_乙基己氧基、壬氧基、癸氧基等。作為-OR ’可列舉：上述之院氧基及環丙氧基、環丁氧基、環己基氧基等環烷氧基等。作為-C02R16，可列舉：曱氧基幾基、乙氧基幾基、丙氧基幾基 '異丙氧基㈣、了氧基喊、異丁氧基叛基、戊氧基幾基、異戊氧基幾基、新戍氧基減、環戍氧基羰基、己氧基幾基、環己氧基幾基、庚氧基M基、環庚氧基 146960.doc 201036941 羰基、辛氧基羰基、2-乙基己氧基羰基、環辛氧基羰基、壬氧基羰基、癸氧基羰基、三環癸氧基羰基、甲氧基丙氧基羰基、乙氧基丙氧基羰基、己氧基丙氧基羰基、2_乙基己氧基丙氧基羰基、甲氧基己氧基羰基等。作為飽和烴基中所包含之-CH2-經取代所得之基，可列舉：甲氧基甲基、乙氧基乙基等含烷氧基之烷基；乙醯基、2-氧丁基等含有側氧基之烷基；N_甲基胺基丙基、 N，N-二甲基胺基丙基等含N_取代胺基之烷基等。 =化合物（1)中，Ri〜Ri5較好的是分別獨立為氫原子、 _R 、_S〇3、-S〇3Na、-S〇3K 或-S03H，且 R1 〜R15 中之一者為- SO3。R1〜R15爭β 、更好的疋分別獨立為氫原子、_R!6、_S〇3- 或〇3H 5中之一者為_s〇3-。進而，r1〜r15特別好的疋刀別獨立為氫原子、_r16、-ShUhH，r1〜r15 者為S〇3 ’ _g_Rl〜R15中之一者為_s〇3H。進而，化合物⑴更好的是下式（la)所示之化合物：(In the formula (1), RLR15 independently represents a hydrogen atom, _R16, _〇H, _〇Rl6, _c〇2H, -co2R16, -so3-, -S〇3Na, _s〇3K or -S03H, and R1 to R15 One of them represents -S03-; R16 represents a saturated hydrocarbon group having a carbon number of 1 to 10, and the hydrogen atom contained in the saturated hydrocarbon group may also be an alkoxy group having a 素 atom, a hydroxyl group or a carbon number of 丨10. Alternatively, _CH2_ contained in the saturated hydrocarbon group may be substituted with _0_, -CO- or -NR17-; R17 represents a hydrogen atom or a saturated hydrocarbon group having a carbon number of i~1〇. 146960.doc 201036941 Furthermore, in the formula (1), the number of positive (+) charges in the compound is the same as the number of negative (a) charges. The saturated hydrocarbon group may be an alkyl group or a cycloalkyl group, and the alkyl group having an alkyl group and an alkyl group having a cycloalkyl group. As the alkyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a methyl propyl group, a methyl propyl group, and a 1- Methyl butyl, 2·methyl butyl, 3-methylbutyl, 2-ethylidene, decyl, decyl, 1,1-dimethylpropyl, ι,2-dimethylpropane Base, 2,2-dimethylpropyl, and the like. The cycloalkyl group may, for example, be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group or a tricyclodecyl group. Examples of the #素 atom include a fluorine atom, a chlorine atom, and a bromine atom. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a 1-methylpropoxy group, a 2-methylpropoxy group, and a third butoxy group. '1-Methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, u_〇trimethylpropoxy, i,2-dimethylpropoxy, 2,2-di Methyl propoxy, n-pentyloxy, n-hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, decyloxy, decyloxy and the like. Examples of the -OR' include the above-mentioned alkoxy groups such as alkoxy groups such as a cyclopropoxy group, a cyclobutoxy group and a cyclohexyloxy group. Examples of -C02R16 include an oxiranyl group, an ethoxy group, a propoxy group 'isopropoxy group (tetra), an oxo group, an isobutoxy group, a pentyloxy group, and a different Pentyloxy, neodecyloxy, cyclodecyloxycarbonyl, hexyloxy, cyclohexyloxy, heptyloxy, cycloheptyloxy 146960.doc 201036941 carbonyl, octyloxy Carbonyl, 2-ethylhexyloxycarbonyl, cyclooctyloxycarbonyl, decyloxycarbonyl, decyloxycarbonyl, tricyclodecyloxycarbonyl, methoxypropoxycarbonyl, ethoxypropoxycarbonyl, Hexyloxypropoxycarbonyl, 2-ethylhexyloxypropoxycarbonyl, methoxyhexyloxycarbonyl, and the like. Examples of the group obtained by substituting -CH2- contained in the saturated hydrocarbon group include an alkoxy group-containing alkyl group such as a methoxymethyl group or an ethoxyethyl group; and an ethyl ketone group or a 2-oxobutyl group; An alkyl group having a pendant oxy group; an alkyl group having an N-substituted amino group such as N-methylaminopropyl group, N,N-dimethylaminopropyl group or the like. In the compound (1), Ri~Ri5 are preferably independently a hydrogen atom, _R, _S〇3, -S〇3Na, -S〇3K or -S03H, and one of R1 to R15 is -SO3 . R1 to R15 compete for β, and better 疋 is independently a hydrogen atom, and one of _R!6, _S〇3- or 〇3H 5 is _s〇3-. Further, the rr of the r1 to r15 is particularly preferably a hydrogen atom, _r16, -ShUhH, and r1 to r15 is one of S〇3'_g_R1 to R15, which is _s〇3H. Further, the compound (1) is more preferably a compound represented by the following formula (la):

(式（la)中，(in (la),

Rl分別獨立表示气屌 π2, 4原子或妷數為1〜10之烷基， R分別獨立表示氫片 TT L原子、-S03-、-S03Na、-S03K、 -so3H ’其中，1個2 Λ 表 >F-S〇3-)。作為化合物⑴，例如可列舉以下之化合物： 146960.doc 201036941 mo3s-^Rl independently represents a gas 屌 π 2 , 4 atom or an alkyl group having a number of turns of 1 to 10, and R independently represents a hydrogen sheet TT L atom, -S03-, -S03Na, -S03K, -so3H ', of which 2 Λ Table > FS〇3-). As the compound (1), for example, the following compounds can be mentioned: 146960.doc 201036941 mo3s-^

⑻ so3m(8) so3m

(式⑷及式（b)中，M表示η、Na或K)。 Ο —如以下所示般，將上述磺酸化合物（1)供給至鹵化（例如耩由通常方法將其氯化）而將其轉換成式（1Α)所示之化合物（以下’有時稱為「磺醯鹵化合物（1Α)」或「化合物 (1Α)」），然後使該磺醯鹵化合物（丨Α)與胺化合物反應。藉由該一連串之反應，可獲得式（2)所示之化合物（以下，有時稱為「磺醯胺化合物（2)」或「化合物（2)」）。(In the formulas (4) and (b), M represents η, Na or K). Ο—The sulfonic acid compound (1) described above is supplied to a halogenated group (for example, ruthenium is chlorinated by a usual method), and is converted into a compound represented by the formula (1Α) as follows (hereinafter sometimes referred to as "Sulfolium halogen compound (1)" or "compound (1)"), and then the sulfonium halide compound (丨Α) is reacted with an amine compound. By the series of reactions, a compound represented by the formula (2) (hereinafter sometimes referred to as "sulfonamide compound (2)" or "compound (2)") can be obtained.

❹ (式（1)、式（1Α)及（2)中 146960.doc -9- 201036941 5、R16及 P 17 之含義與上述相同 A 3 .n R1 〜R1 R'A~R13A^ alf '❹ (Formula (1), Formula (1Α) and (2) 146960.doc -9- 201036941 5. The meanings of R16 and P 17 are the same as above. A 3 .n R1 〜R1 R'A~R13A^ alf '

C02H、_c〇2R!6、 ΙΑ t^I5A 蜀立表示氫原子、-R16、-〇H' -OR!6、 ’so3k 或-so3h r1A R〜 SCV、-S〇3Na 中之—者表示_S〇2X。 x表示i素原子。 R21〜R35分別獨立主一，表不 A 原子、-R丨6、_〇H、_〇Rl6、 -co2h、-co2r“ -s〇2n(r-)r19^ 3 ' -s〇3Na' -so3k^so3h> ():或者-so2nhr18，r21〜r、之一者 · ’ R〜R中之至φ — 18 者表〒-S〇2N(R18)R194_s〇2>iHRi8。 σ刀別獨立表示碳數為i〜i〇之烷基、碳數為 3〜3〇之環烷基、磁盔反致為 5 y 數為6〜10之一價之芳香族烴基或碳數為數Γ 香㈣環基，或者亦可相互鍵結而形成碳 1二雜環’該燒基及該環烧基中所包含之氫原子亦可人·、、原+㉟基或苯基取代。該烧基及該環烧基中所包一 H2亦可取代成-〇-、-CO-、-NH-或-NR16-，該芳香族煙基及該芳香旌雜a 、”衣土中所包含之氫原子亦可由鹵素原子、/Rl6、-〇H、侦,6、佩、-CH=CH|CH=CHR，代）弋（）式（1A)及（2)之各化合物中之+電荷數與-電荷數均相同。朴作為方香族烴基，可列舉：芳基、芳烧基、具有烧基之方基等。作為芳基，可列舉：苯基、萘基、聯苯基、蒽基、菲基等。作為具有烷基之芳基，除甲苯基、二甲苯基、異丙苯基、菜基、2,6-二乙基苯基、2_曱基_6_乙基苯基等以外， 146960.doc -10- 201036941 亦可任意組合上述取代基。C02H, _c〇2R!6, ΙΑ t^I5A 蜀 stands for hydrogen atom, -R16, -〇H' -OR!6, 'so3k or -so3h r1A R~ SCV, -S〇3Na - means _ S〇2X. x represents an atom of an atom. R21~R35 are independent of the main one, and represent A atom, -R丨6, _〇H, _〇Rl6, -co2h, -co2r" -s〇2n(r-)r19^ 3 ' -s〇3Na' - So3k^so3h> (): or -so2nhr18, r21~r, one of them, 'R~R to φ-18, the expression 〒-S〇2N(R18)R194_s〇2>iHRi8. An alkyl group having a carbon number of i~i〇, a cycloalkyl group having a carbon number of 3 to 3 Å, or a magnetic olefin having a 5 y number of 6 to 10 or a carbon number of a scent (4) ring a group or a bond may be bonded to each other to form a carbon di-heterocyclic ring. The alkyl group and the hydrogen atom contained in the ring-burning group may be substituted with a human, an original +35 group or a phenyl group. The H2 contained in the cycloalkyl group may also be substituted with -〇-, -CO-, -NH- or -NR16-, and the aromatic nicotine group and the aromatic aza, "the hydrogen atoms contained in the soil" are also The number of + charges and the charge in each compound of the formula (1A) and (2) can be represented by a halogen atom, /Rl6, -〇H, Detect, 6, and -CH=CH|CH=CHR. The numbers are the same. Examples of the porphyrin hydrocarbon group include an aryl group, an aryl group, and a group having a burnt group. The aryl group may, for example, be a phenyl group, a naphthyl group, a biphenyl group, an anthracenyl group or a phenanthryl group. As the aryl group having an alkyl group, in addition to tolyl, xylyl, cumyl, decyl, 2,6-diethylphenyl, 2-fluorenyl-6-ethylphenyl, etc., 146960. Doc -10- 201036941 The above substituents may also be arbitrarily combined.

作為雜環’可為芳香族雜環作為不具有芳香性之雜環基亦可為不具有芳香性者。可列舉：The heterocyclic ring ' may be an aromatic heterocyclic ring as a heterocyclic group having no aromaticity, or may have no aromaticity. Can be listed:

等再者’上述環之結合鍵可為任意之位置及以上所記載之位置之任一者。〇作為-s〇2NHRl8，可列舉：胺續醯基、N_(甲基）胺確酿土 N (乙基）胺磺醯基、N-(丙基）胺磺醯基、N_(異丙基）胺s醯基、N-(丁基）胺磺醯基、N-(異丁基）胺磺醯基、N-- (戊基）胺磺醯基、N_(異戊基）胺磺醯基、N_(新戊基）胺磺 • 醯基、N-(環戊基）胺磺醯基、N_(己基）胺磺醯基' N_(環己基）胺確醯基、N-(庚基）胺磺醯基、N-(環庚基）胺磺醢基、 N_(辛基）胺磺醯基、N-(2-乙基己基）胺磺醯基、N-(l,5-二甲基己基）胺磺醯基、N-(環辛基）胺磺醯基、N-(壬基）胺磺醯基、N-(癸基）胺磺醯基、N-(三環癸基）胺磺醯基、N-(曱 146960.doc 11 201036941 氧基丙基）胺磺醯基、N-(乙氧基丙基）胺磺醯基、N-(丙氧基丙基）胺磺醯基、N-(異丙氧基丙基）胺磺醯基、N-(己氧基丙基）胺磺醯基、N-(2-乙基己氧基丙基）胺磺醯基、N-(曱氧基己基）胺磺醯基、N-(3-苯基-1-甲基丙基）胺磺醯基等。進而，作為-S02NHR18，可列舉下述式所示之基。其中，於以下之式中，X1表示鹵素原子。X3表示碳數為1〜3 之烷基或碳數為1〜3之烷氧基，該烷基及烷氧基之氫原子亦可由鹵素原子取代。X2表示碳數為1〜3之烷基、碳數為 1〜3之烷氧基、鹵素原子或硝基，該烷基及烷氧基之氫原子亦可由鹵素原子取代。作為可由鹵素原子取代之碳數為1〜3之烷基，除上述烷基以外，亦可列舉全氟曱基等。作為可由鹵素原子取代之碳數為1〜3之烷氧基，可列舉上述烷氧基，尤其是甲氧基、乙氧基、丙氧基等。 NHS〇2Further, the combination of the above-mentioned rings may be any of the positions described above and the positions described above. 〇 as -s〇2NHRl8, may be exemplified by: amine sulfhydryl, N_(methyl)amine indeed, soil N (ethyl) sulfonyl, N-(propyl)amine sulfonyl, N_(isopropyl Amine s-mercapto, N-(butyl)amine sulfonyl, N-(isobutyl)amine sulfonyl, N-(pentyl)amine sulfonyl, N-(isopentyl)amine sulfonate Base, N_(neopentyl)amine sulfonate, fluorenyl, N-(cyclopentyl)amine sulfonyl, N-(hexyl)amine sulfonyl 'N_(cyclohexyl)amine thiol, N-(heptyl) Aminesulfonyl, N-(cycloheptyl)aminesulfonyl, N_(octyl)aminesulfonyl, N-(2-ethylhexyl)aminesulfonyl, N-(l,5-di Methylhexyl)amine sulfonyl, N-(cyclooctyl)amine sulfonyl, N-(fluorenyl)amine sulfonyl, N-(fluorenyl)amine sulfonyl, N-(tricyclodecyl) Aminesulfonyl, N-(曱146960.doc 11 201036941 oxypropyl)amine sulfonyl, N-(ethoxypropyl)amine sulfonyl, N-(propoxypropyl)amine sulfonate Sulfhydryl, N-(isopropoxypropyl)amine sulfonyl, N-(hexyloxypropyl)amine sulfonyl, N-(2-ethylhexyloxypropyl)amine sulfonyl, N-(decyloxyhexyl)amine sulfonyl, N-(3-phenyl-1-methylpropyl)amine Sulfonyl and the like. Further, examples of -S02NHR18 include groups represented by the following formulas. Here, in the following formula, X1 represents a halogen atom. X3 represents an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, and the hydrogen atom of the alkyl group and the alkoxy group may be substituted by a halogen atom. X2 represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a halogen atom or a nitro group, and the hydrogen atom of the alkyl group and the alkoxy group may be substituted by a halogen atom. The alkyl group having 1 to 3 carbon atoms which may be substituted by a halogen atom may be a perfluoroindenyl group or the like in addition to the above alkyl group. The alkoxy group having 1 to 3 carbon atoms which may be substituted by a halogen atom may, for example, be an alkoxy group, particularly a methoxy group, an ethoxy group or a propoxy group. NHS〇2

νη!ο2Ηη!ο2

nhso2Nhso2

nhso2 nhso2Nhso2 nhso2

nhso2Nhso2

NHS〇2 NHS〇2 nhso2 nhso2 nhso2 NHSOo I NHS〇2 [MeNHS〇2 NHS〇2 nhso2 nhso2 nhso2 NHSOo I NHS〇2 [Me

146960.doc -12- 201036941146960.doc -12- 201036941

NHS〇2 μο—x^nhso2NHS〇2 μο—x^nhso2

nhso2 NHS〇2 nhso2 ΗσNhso2 NHS〇2 nhso2 Ησ

HO 'nhso2 ho、HO 'nhso2 ho,

HO 、nhso2 NHio2 、nhso2 HO’^Y^NHSC^HO, nhso2 NHio2, nhso2 HO’^Y^NHSC^

OH 、nhs〇2 ho々^n^^nhs〇2OH, nhs〇2 ho々^n^^nhs〇2

Me〇-NHS02 、NHS〇2 'nhso2 、nhso2 、nhso2- \/°'^nhso2 、丄2Me〇-NHS02, NHS〇2 'nhso2, nhso2, nhso2- \/°'^nhso2, 丄2

nhso2 丨〇\ 146960.doc •13· 201036941Nhso2 丨〇\ 146960.doc •13· 201036941

II

I 'n-s/^nhs〇2I 'n-s/^nhs〇2

r^^NHSOz OMer^^NHSOz OMe

H 又 nhso2 O O -^NHS〇2 αν^^ΝΗ8〇2 〇 NHS〇2 〇V1 nc'v-/^nhso2 Me〇· 又 nhso2 NHS〇2H and nhso2 O O -^NHS〇2 αν^^ΝΗ8〇2 〇 NHS〇2 〇V1 nc'v-/^nhso2 Me〇· and nhso2 NHS〇2

I I x1^^NHS。2 x1’^^nhso2I I CF3CH2NHS〇2 cf3(cf2)7ch2nhs〇2I I x1^^NHS. 2 x1’^^nhso2I I CF3CH2NHS〇2 cf3(cf2)7ch2nhs〇2

ClCl

Cl \^J^/Nhs〇2 nhs〇2 [i xp2Cl \^J^/Nhs〇2 nhs〇2 [i xp2

NHS〇2 丁 B「2NHS〇2 D B "2

nhso2 J^OMe V N〇2Nhso2 J^OMe V N〇2

146960.doc 14- 201036941146960.doc 14- 201036941

ο -nhso2Ov -nhso2

NHS〇2 ,NHS〇2 A 、〇〆 ,nhso2 NHS〇2 nhso2 其中，作為-S02NHR18，較好的是R18為碳數1〜10之直鏈或分枝之烧基。〇作為-S02N(R18)R19，可列舉以下之基：NHS〇2 , NHS〇2 A , 〇〆 , nhso2 NHS〇2 nhso2 wherein, as -S02NHR18, it is preferred that R18 is a linear or branched alkyl group having a carbon number of 1 to 10. 〇 As -S02N(R18)R19, the following bases can be cited:

146960.doc 15- 201036941 作為R18及R19相互鍵結示之基：而形成之雜環可列舉下述式所146960.doc 15- 201036941 As the basis for the mutual bond between R18 and R19: The heterocyclic ring formed can be exemplified by the following formula

Ϊ 46960.doc 16- 201036941 其中，作為Rl8及Rl9,較好的是碳數為卜1〇之炫基、碳數為5〜7之環烷基、烯丙基、苯基、碳數為8〜1〇之芳烷基、碳數為2〜8之含經基之絲及芳基、碳數為之含燒氧基之烷基及芳基，更好的是碳數為6〜8之分枝狀烷基，特別好的是2-乙基己基。 1:化合物⑺中，R21〜R35較好的是分別獨立為氫原子、 -R16、-S03·、-S03H、-S03Na、-S〇3K、_s〇 N(Rl8)Rl9 或Ϊ 46960.doc 16- 201036941 wherein, as Rl8 and Rl9, a cyclyl group having a carbon number of 1 〇, a cycloalkyl group having a carbon number of 5 to 7, an allyl group, a phenyl group, and a carbon number of 8 are preferred. ～1〇 aralkyl group, a carbon number of 2 to 8 containing a mercapto group and an aryl group, a carbon number containing an alkoxy group and an aryl group, more preferably a carbon number of 6 to 8 A branched alkyl group is particularly preferably 2-ethylhexyl. In the compound (7), R21 to R35 are preferably independently a hydrogen atom, -R16, -S03., -S03H, -S03Na, -S〇3K, _s〇 N(Rl8)Rl9 or

者-S— w丨〜〜至少一者為或二〇2NHR18。R21〜R”特別好的是分別獨立為氫原子、 R16、-S03-、-so3H、-so2n(r18)r19 或者 _s〇2NHRl8，且 21 3 5 R 〜R 中之至少一者為_s〇2N(Rl8)Rly_s〇2NHRl8。進而，化合物（2)更好的是以下之式（2a)所示之化合物：-S-w丨~~ At least one or 2NHR18. R21 to R" are particularly preferably independently hydrogen atoms, R16, -S03-, -so3H, -so2n(r18)r19 or _s〇2NHRl8, and at least one of 21 3 5 R 〜 R is _s 〇2N(Rl8)Rly_s〇2NHRl8 Further, the compound (2) is more preferably a compound represented by the following formula (2a):

(2a) (式（2a)中， τ> 2 11 R分別獨立表示氫原子或碳數為1〜10之烷基， R22分別獨立表示氫原子、_s〇3-、_s〇3Na、_s〇3K、 _S〇3H、'S〇2N(r18)r19或者-S02NHR18，其中，1個 r22,表不-S03，且至少 1個 R22,表示 _s〇2N(r18)r19 或 _s〇2Nhr18)。作為化合物（2)，可列舉以下之化合物、化合物（2_ 2)以及化合物（2-3)。 146960.doc -17- 201036941 化合物（2-1)為如下之化合物，即於式（2)中，R2丨〜r35八別獨立表示氫原子、_Ri6、_〇H、_〇Rl6、_c〇2H、 -S03、-S03Na、-S03K、-S〇3H或者-S02N(R18)R19 ,並且， R21〜R35中之一者表示_s〇3-，且r21〜r35中之—者表八 -S02NR丨8R丨9的化合物。不化合物（2-1)較好的是為如下之化合物，即於式（？）中 R21〜R35分別獨立表示氫原子、_Rl6、_s〇 ’ 6 bUsNa、 -S03K、-S03H或者-SC^NCR18)!^，並且， R21〜R35中之一者表示_s〇3_，且r21〜尺3 一 ^ ,« 10 T < 一者表示 -so2nr18r19的化合物。化合物（2-2)為如下之化合物，即於式（2)中，別獨立表示氫原子、-R16、_〇H、_〇Ri6、刀 -lu2H、_c〇2r16 -S03、-S03Na、-S03K、-S03H或者-S〇2NHR18，並且 R〜R中之一者表示_S〇3_，且r2 1〜尺35中+ 0 18 T之一者表示 -S02NHR18的化合物。化合物（2-2)較好的是為如下之化合物，即於式 R2丨〜R35分別獨立表示氫原子、_Ri6、工中 ~b〇3 ' -S〇3Na -S03K、-S03H或者-S02NHR18，R21 〜尺35由不 T之一者表 -S03-，且 R21〜R35分 -C〇2R_16、 )R19或者 R21〜R35中之一者表示-S02NHR18的化合物。化合物（2-3)為如下之化合物，即於式（2)中別獨立表示氫原子、-R16、-OH、-〇Ri6、 -SO/、-S03Na、-S〇3K、-S〇3h、_S〇2N(r】8 -S02NHR18，R21 〜R35 中之一者表示 _s〇3-，且 146960.doc -18· 201036941 R〜R中之至少兩者表示-so2n(r18)r19 化合物。或 _S〇2nhri 的較好的是化合物（2_3)為如下之化合物，即於式（2)中， R21〜R35分別獨立表示氫原子、_Rl6、_s〇3_、 -so3K、-S03H、-S02N(R18)R19或者_s〇2NHRl8，且 R21〜R”中之一者表示·s〇3.，r21〜r35中之至少兩者表— -S02N(R18)R19 或 _S〇2NHRi8 的化合物。不〇〇作為化合物（2) ’例如可列舉以下之化合物：(2a) (In the formula (2a), τ> 2 11 R each independently represents a hydrogen atom or an alkyl group having a carbon number of 1 to 10, and R22 independently represents a hydrogen atom, _s〇3-, _s〇3Na, _s〇3K, respectively. , _S〇3H, 'S〇2N(r18)r19 or -S02NHR18, wherein one r22, not -S03, and at least one R22, representing _s〇2N(r18)r19 or _s〇2Nhr18). The compound (2) includes the following compounds, the compound (2-2), and the compound (2-3). 146960.doc -17- 201036941 The compound (2-1) is a compound in which R2丨~r35 independently represents a hydrogen atom, _Ri6, _〇H, _〇Rl6, _c〇2H, in the formula (2). , -S03, -S03Na, -S03K, -S〇3H or -S02N(R18)R19, and one of R21~R35 represents _s〇3-, and r21~r35--Table 8-S02NR丨8R丨9 compound. The compound (2-1) is preferably a compound in which R21 to R35 independently represent a hydrogen atom, _Rl6, _s〇'6 bUsNa, -S03K, -S03H or -SC^NCR18 in the formula (?). !!^, and one of R21 to R35 represents _s〇3_, and r21~3 is a ^, «10 T < One represents a compound of -so2nr18r19. The compound (2-2) is a compound which, in the formula (2), independently represents a hydrogen atom, -R16, _〇H, _〇Ri6, Knife-lu2H, _c〇2r16-S03, -S03Na, - S03K, -S03H or -S〇2NHR18, and one of R~R represents _S〇3_, and one of +0 18 T in r2 1~foot 35 represents a compound of -S02NHR18. The compound (2-2) is preferably a compound in which the hydrogen atom, _Ri6, in-worker ~b〇3'-S〇3Na-S03K, -S03H or -S02NHR18 are independently represented by the formulas R2丨 to R35. R21 to 尺35 are represented by one of the non-T-S03-, and R21 to R35-C〇2R_16, R19 or R21 to R35 represent a compound of -S02NHR18. The compound (2-3) is a compound which independently represents a hydrogen atom, -R16, -OH, -〇Ri6, -SO/, -S03Na, -S〇3K, -S〇3h in the formula (2). , _S〇2N(r)8 - S02NHR18, one of R21 to R35 represents _s〇3-, and 146960.doc -18· 201036941 At least two of R to R represent a compound of -so2n(r18)r19. Or _S〇2nhri is preferably a compound (2_3) which is a compound in which R21 to R35 independently represent a hydrogen atom, _Rl6, _s〇3_, -so3K, -S03H, -S02N, in the formula (2). (R18) R19 or _s〇2NHRl8, and one of R21 to R" represents ·s〇3., at least two of r21 to r35 are -S02N(R18)R19 or _S〇2NHRi8. As the compound (2) ', for example, the following compounds can be cited:

⑼ sr(9) sr

如上所述可較作為用於將續酸化合物（1)鹵化之試南j，好地使用亞硫酸鹵化合物，例如亞硫酿氣。亞硫醯函化合物之使用量較好的是相對於錯酸 W0莫耳倍。其中’於所使用之續酸化合物⑴ 較多的情形等反應系統中導入有水之件β + 3 7量 h形時，較好的是佶用更多量之亞硫醯iS化合物來分解水。 κ 146960.doc -19- 201036941 反應係於溶鈉中進行。作為此種溶劑，例如可列舉：四虱咬喃、二11号烷等醚類，氯仿、二氯甲烷、1，2-二氯乙烧王氯乙稀（perehiQrGethylene)、二氣丙燒、氯戊烧、 1，2-二溴乙烷等_化烴類，乙腈等腈類等。較好的是氣仿或乙腈。作為溶劑之使用量，可列舉相對於磺酸化合物⑴為 3〜10質量倍，較好的是5〜8質量倍。該反應較好的是於N，N_二烷基曱醯胺之存在下進行。作為N，N- 一烷基甲醯胺，例如可列舉·· N，N，_二甲基甲醯胺、N，N,_二乙基甲酿胺等。其使用量相對於亞硫醯鹵化合物為0·05〜1莫耳倍。反應例如，、要於溶劑中將續酸化合物⑴與亞硫酿齒化合物加以混合即可。於使用Ν，Ν-二烧基甲醯胺之情形時，只要於溶劑中將磺酸化合物⑴、亞硫醯齒化合物以及 Ν，Ν-二烷基甲醯胺加以混合即可。具體而S，就可抑制發熱之觀點而言，較好的是於溶劑中將確酸化合物⑴及Ν，Ν_二烧基甲醯胺加以混合後，滴加亞硫5落函。反應溫度為or以上，較好者可列舉3(rc以上且為 70 C以下’較好者可列舉6(rc以下。反應時間為〇 58小時，較好的是3〜5小時。以上述方式所獲得之磺醯自化合物(ia)，可藉由將反應後之反應混合物與水混合後’濾取所析出之結晶的方法而自反應混合物中取出。可對自反應混合物中取出之績酿齒 146960.doc -20- 201036941 化合物（1A)進行水洗。又，可進行乾燥亦可不乾燥而用於與胺化合物之反應。侧化合物UA)例如可藉由於溶劑中將磺醢齒化合物 • (1A)及胺化合物加以混合而進行反應。具體而t，只要於溶劑中加入石黃醯函化合物（1A)，然後滴加胺化合物即可。、作為胺化合物，例如可列舉：正丙胺 '正丁胺、正己胺、二甲基己胺、U，3,3,甲基丁胺、2_乙基己胺、 ❹3 基·1_本基丁烧 '異丙氧基丙胺等。該等可單獨使用、或者組合兩種以上來使用。胺化合物之使用量相對於磺醯幽化合物(ια”較好的是 3〜丨〇莫耳倍，更好的是3〜7莫耳倍以下。該反應較好的是於鹼性觸媒之存在下進行。作為驗性觸媒，例如可列舉：三乙胺、三乙醇胺等脂肪族一、.及⑯派咬等芳香族三級胺等三級胺，二乙胺等脂肪族二級胺，吡啶等芳香族二級胺等二級胺等。其中，較好 ❹&疋使用一級胺’更好的是使用脂肪族三級胺，特別好的是使用三乙胺。㈣觸媒之使用量相對於胺化合物，通常為U〜2莫耳 • 倍左右。 .驗性觸媒可與胺化合物⑽滴加，亦可與胺化合物分開來添加。反應溫度通常為0〜5(rc左右，較好的心赋。反應時間較好的是1〜5小時。 (第2步驟） 146960.doc •21 - 201036941 至少使用酸性水溶液清洗上述第丨步驟中所獲得之反應後之反應物’或者至少使用60t以上、饥以下之水，較、好的是抓以上、9(rc以下之水清洗該反應後之反應物。Λ 反應物之清洗只要包含利用酸性水溶液之丨次清洗或者利用6代以上、95°c以下之水之1次清洗，則亦可包含使用其他溶劑之清洗、使用未達6〇〇c之水之清洗等。作為此處之酸性水溶液，只要為？1€值為5左右以下之水冷液，則亚無特別限定，例如較好的是鹽酸水溶液、乙酸水溶液、硫酸水溶液等。酸性水溶液之清洗時之溫度並無特別限定，可為任何溫度。較好的是0〜80。〇，更好的是 10〜70C ’特別好的是2〇〜6〇。〇。又，60 C以上、951以下之水較好的是使用去離子水。又，較好的是9(TC以下之水，更好的是85r以下之水進而更好的是8 0 °C以下。 (第3步驟）對上述第2步驟中所獲得之清洗物、即磺醯胺化合物進行乾燥。乾燥可利用自然乾燥、熱風乾燥、減壓乾燥等各種方法進行。例如，乾燥時之溫度較好的是4〇〜6〇r。乾燥所需要之時間較好的是8〜24小時，更好的是12〜18小時。較好的是根據所使用之方法，以使磺醯胺化合物中之含水率達到3%以下之方式進行乾燥。以上述方式所獲得之續醢胺化合物可較佳地用作染料，尤其是彩色濾光片陣列之彩色濾光片中所使用之染料。 146960.doc -22- 201036941 即，含有該磺醯胺化合物作為色素之著色感光性樹脂組合物可適且地用作彩色濾光片形成用之感光性樹脂組合物。 (第4步驟） .本务明之著色感光性樹脂組合物之製造方法中，於進行上述第1〜第3步驟之後，作為第4步驟，將磺醯胺化合物與選自由顏料或顏料分散液（B)、溶劑（C)、樹脂（D)、光聚合 I1生化a物（E)以及光聚合起始劑（ρ)所組成群中之至少— _ 混合。〇此處，磺醯胺化合物可直接與上述各成分混合，但較合適的是至少兩階段地通過過濾器而獲得與各成分之混合物。例如，可列舉藉由進行以下所示之第5〜第7步驟而與各成分混合，或者藉由進行第8〜第1〇步驟而與各成分混合之方法。藉由進行該等步驟，可以簡便之方法將微小異物之存在抑制為最小限度，且能夠以膜厚均句之塗膜獲得高精〇細之彩色濾光片。第5步驟：使包含藉由上述磺醯胺化合物之製造方法所獲得之磺醯胺化合物的染料溶液（Α)通過第丨過濾器之步驟；乂、第6步驟：使通過第丨過遽器後之染料溶液（a)通過第2過〉慮之步驟；第7步驟：使通過第2過遽器後之染料溶液（A)與選自由顏料或顏料分散液（B)、溶劑（C)、樹脂（D)、光聚合性化合物（E)以及光聚合起始劑（F)所組成群中之至少一種混合的 146960.doc •23· 201036941 步驟。 —第8步驟.使包含藉由上述確酿胺化合物之製造方法所獲仵之磺醯胺化合物的染料溶液（A)通過第3過濾器之步弟v驟：將通過第3過濾器後之染料溶液（A)與選自由顏料或顏料分散液（B)、溶劑（〇、樹脂（D)、光聚合性化合物（E)以及光聚合起始劑（F)所組成群中之至少一種混合2 獲得混合物的步驟，弟〇步驟.使混合物通過第4過滤器之步驟。 (第5步驟）所谓包含績醯胺化合物之染料溶液（A)，可為僅含有上述續醯胺化合物且上述續醒胺化合物為一種或兩種以上的溶液:亦可為進而含有一種或兩種以上之其他溶劑可溶性之染料的溶液。作為其他溶劑可溶性之染料，只要為可溶解於溶劑之％領域公知之染料則可使用相同者，例如可列舉：日本專利特開昭64-90403號純、日本專利特開昭64 9⑽號公報、日本專利特開平卜9侧號公報、日本專利特開平6 wu號公報、日本專㈣登25922(>7號、美國專利第 4，_，5〇1號、美國專利第5,667,92〇號、美國專利第冰9，·號、日本專利㈣平5_3332()7號純、日本專利特開平6·3测號公報、日本專利特開平6_川15號公報、日本專利特開平6_19彻號公報等所記載之染料/色素中之〜1可冷!·生者’尤其是酸性染料、鹼性染料、直接染料、 146960.doc -24· 201036941 硫化染料、甕染料、萘酚染料、反應性染料、分散染料等。 ’、作為染料之化學結構’可為下述結構中之任—者：吼唾 . 偶氮系、苯胺基偶氮系、芳基偶氮系、吡唑并***偶氮系:、吡啶酮偶氮系、三苯甲烷系、蒽醌系、蒽吡啶酮系、笨亞曱基系、氧嘆系、花青系、聚次曱基系、啡嗟啡系、吡咯：吡唑次甲基偶氮系”山口星系、酞花青系' 喹酞酮〇系、、苯并吡喃系、靛藍系、二哼畊系、香豆素系、方酸菁 (squarylium)系等。用於溶解染料溶液（A)中之染料之溶劑可為水，但較好的是有機溶劑。例如可自以下有機溶劑中選擇使用：酯類（含-COO-之溶劑）、酯類以外之醚類（含之溶劑）、酯類以外之酮類（含 CO-之/合劑）、醇類、芳香族烴類、醯胺類、甲基吡咯啶酮、二曱亞砜等中。〇作為上述酯類，例如可列舉：乳酸曱酯、乳酸乙酯、乳酸丁酯、2-羥基異丁酸甲酯、乙酸乙酯、乙酸_正丁酯、乙酸異丁酯、甲酸戊酯、乙酸異戊酯、丙酸丁酯、丁酸異丙 ' 酯、丁酸乙酯、丁酸丁酯、羥乙酸甲酯、甲氧基乙酸甲 • 酯、曱氧基乙酸乙酯、甲氧基乙酸丁酯、乙氧基乙酸甲酉曰、乙氧基乙酸乙酯、3 -甲氧基丙酸曱酯、3 -甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2_甲氧基丙酸丙酯、2_乙氧基丙酸甲酯、2-乙氧基丙酸乙酯、2-甲氧基-2-甲基丙酸 146960.doc -25- 201036941 甲S曰、2-乙氧基_2_甲基丙酸乙酯、丙酮酸甲酯、丙_酸乙酯、丙酮酸丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、2-側氧丁酸甲醋、2·側氧丁酸乙酯、3_甲氧基乙酸丁酯、3_甲氧基-3-甲基乙酸丁酯、環己醇乙酸酯、γ_丁内酯等。、乙一醇早丁謎、一乙二醇單甲驗作為上述喊類，例如可列舉 ***、乙二醇單丙醚乙醇單***、二乙二醇單丁醚、丙二醇單甲醚、丙二醇單乙_、丙二醇單丙醚、丙二醇單丁醚、醇、3-甲氧基-3·甲基丁醇、乳基丁四氫吱喃、四氫。比喃、Μ〇号烧、二乙二醇二甲喊、 -乙二醇二乙趟、二乙二醇甲基***'二乙二醇二丙謎、二二…、丙二醇單甲趟乙酸醋、丙二醇單乙謎乙 :-知早丙醚乙酸酯、甲基溶纖劑乙酸酯纖劑乙酸酯、乙基卡必醇乙酸醋 θ乙基- 甲謎、苯乙喊、甲基苯甲_等。卡，乙酸醋、苯作為上述酮類’例如可列舉：4，丙酮、2-庚酮、3_庚酮、4_庚二2-戍酮：酉同、環戊嗣、環己_、異佛_等。基I戊作為上述醇類，例如可列舉：醇、己醇、環己醇、乙二醇 _ '丙醇'丁 tt_ 内~醇、丙二醢笙作為上述芳香族烴類，例如可列舉：Γ 。苯、均三曱苯等。 .本、甲笨、二曱胺作為上述醯胺類’例如可列舉：Μ Ν，Ν-二甲基乙醯胺、Ν_甲基^各啶_等： 146960.doc * 26 - 201036941 該等溶劑可單獨使用，亦可組合兩種以上來使用。於染料溶液（增，相對於染料溶液總量，較好的是溶解有1〜30質量％之染料。 .、較好的是於通過m慮器之前，向染料溶液⑷中添加 •，劑。作為此處之過濾劑’例如可列舉：矽藻土、珍珠 '膨/閏土、酸性白土、高嶺土、石夕膠等，其中較好的是矽藻土、酸性白土、矽膠。〇 *使染料溶液⑷通過之第㈤心只要為先前以來過滤用途等中所使用者，則可無特別限定地使用。例如可列舉： =PTFE(P〇lytetraflu〇rethylene，聚四氟乙烯）等氟碳樹月曰聚乙烯、聚丙婦（PP，p〇lypr〇pylene)等聚稀煙樹脂（包含向密度、超高分子量）等形成之過濾器。第1過濾益之孔徑較好的是〇 5〜5 〇，更好的是〇·5 2.5 μηι，進而更好的是(^〜丨5 μιη。藉由設定為該範圍，可去除混入至溶解之染料中的會於後續步驟中阻礙製〇備均勻之著色組合物的微細之異物、或自著色組合物獲得的塗膜上之異物。再者使用第1過遽器之過遽可僅進行1次，亦可進行2 人乂上又’亦可將上述範圍内的不同孔徑之第1過淚器組合。此處之孔徑可參照過濾器製造商之標稱值。作為市售之過遽器，例如可自日本Pall股份有限公司、Advantec 東洋股份有限公司、日本Entegrjs股份有限公司（原曰本 Mykr〇lls股份有限公司）或者Kitz Micro Filter股份有限公司等所提供之各種過濾器中選擇。 146960.doc -27- 201036941 作為使染料溶液（A)通過第丨過濾器之過滤方法，可列舉：自然過遽、減壓過澹（抽氣過遽）、加壓慮等。於加壓過遽之情形時，其壓力較好的是 MPa。 ’ (第6步驟）使通過第丨過濾器後之染料溶液（A)通過第2過據器。第2過濾器可使用由與上述第丄過滤器相同之材料等所形成者。第2過濾器之孔徑較好的是〇〇1〜〇 5 μπι，更好的是叫’進而更好的是〇〇1〜〇」叫。藉由設定為= 粑圍’可去除混入至溶解之染料中的會於後續步驟中阻礙製備均勻之著色組合物的微細之異物、或者自著色組合物獲得的塗膜上之異物。窃尤其是第1過渡器之孔徑與第2過滤器之孔徑的比較好的是設定為1:1〜500:1 ’更好的是2.5:1〜250:1，進而更好的是 5:1 〜150:1 〇使用第2過濾态之過濾可僅進行丨次，亦可進行2次以上。又，亦可將上述範圍内的不同孔徑之第2過濾器組合0 作為使上述混合液通過第2過濾器時之過濾方法，可列舉與通過第1過濾器時之方法相同之方法。其中，就抑制通過過濾器後之染料溶液（Α)中混入水分等之觀點而言，較好的疋於h性氣體環境下，藉由加壓過濾使上述混合浪通過過濾器。該加壓過濾時之壓力與通過第丨過濾器時之壓力相同’較好的是0.0U 〇 MPa。 146960.doc -28 * 201036941 (第7步驟）、將通過弟1及第2過濾器後之染料溶液（A)與選自由顏料或顏料分散液（B)、溶劑（C)、樹脂（D)、光聚合性化合物 (E)以及光聚合起始劑（F)所組成群中之至少一種混合。就減少自著色組合物獲得之塗膜上之異物的觀點而言，較好的是對第7步驟中所獲得之混合物進行第1〇步驟。As described above, it is preferable to use a sulfurous acid halogen compound such as a sulfite gas as a test for halogenating the acid-reducing compound (1). The use of the sulfinium compound is preferably a molar ratio of W0 to the wrong acid. In the case where the amount of the acid-reducing compound (1) used is large, and the amount of the water-inducing member β + 3 7 is introduced into the reaction system, it is preferred to use a larger amount of the sulfite iS compound to decompose the water. . κ 146960.doc -19- 201036941 The reaction is carried out in sodium. Examples of such a solvent include ethers such as tetraterpene and dioxane, chloroform, methylene chloride, 1,2-dichloroethene (perehiQrGethylene), di-propylene-acrylic acid, and chlorine. a hydrocarbon such as pentyl alcohol or 1,2-dibromoethane, or a nitrile such as acetonitrile. Preferred is gas imitation or acetonitrile. The amount of the solvent to be used is 3 to 10 times by mass, preferably 5 to 8 times by mass, based on the sulfonic acid compound (1). This reaction is preferably carried out in the presence of N,N-dialkylguanamine. As the N,N-monoalkylcarbamide, for example, N,N, dimethylformamide, N,N, dimethylethylamine or the like can be mentioned. It is used in an amount of from 0. 05 to 1 mol per mol of the sulfinium halide compound. For example, the acid-requiring compound (1) and the sulfur-containing brewing compound may be mixed in a solvent. In the case of using hydrazine, hydrazine-dialkylcarbamamine, the sulfonic acid compound (1), the sulfinium dentate compound, and the hydrazine-dialkylformamide may be mixed in a solvent. Specifically, from the viewpoint of suppressing heat generation, it is preferred to mix the acid-accurate compound (1) and hydrazine, hydrazine-dicarbocarbamide in a solvent, and then add a sulphur-containing 5 drop function. The reaction temperature is or more, and preferably 3 (rc or more and 70 C or less) is preferably 6 (rc or less. The reaction time is 〇58 hours, preferably 3 to 5 hours. The obtained sulfonium oxime from the compound (ia) can be taken out from the reaction mixture by mixing the reaction mixture after the reaction with water and then filtering out the precipitated crystals. Teeth 146960.doc -20- 201036941 Compound (1A) is washed with water. Further, it can be dried or not dried for reaction with an amine compound. Side compound UA) can be obtained, for example, by a sulfonate compound in a solvent. And the amine compound is mixed and reacted. Specifically, as long as the rhubarb compound (1A) is added to the solvent, the amine compound may be added dropwise. As the amine compound, for example, n-propylamine is used. Amine, n-hexylamine, dimethylhexylamine, U, 3,3, methylbutylamine, 2-ethylhexylamine, ❹3 yl group 1_benyl butyl acetonate, isopropoxy propylamine, etc. Use or combine two or more types. Amine compounds The amount is preferably from 3 to 丨〇 moles, more preferably from 3 to 7 moles, relative to the sulfonate compound (ια). The reaction is preferably carried out in the presence of a basic catalyst. Examples of the test catalyst include a tertiary amine such as an aliphatic monoamine such as triethylamine or triethanolamine, an aromatic tertiary amine such as a 16-bit bite, an aliphatic secondary amine such as diethylamine, and an aromatic pyridine. A secondary amine such as a secondary amine, etc. Among them, it is preferred to use a primary amine, and it is more preferable to use an aliphatic tertiary amine, and it is particularly preferable to use triethylamine. (4) The amount of the catalyst used relative to the amine The compound is usually about U~2 moles. The test catalyst can be added dropwise with the amine compound (10) or added separately from the amine compound. The reaction temperature is usually 0~5 (around rc, better heart) The reaction time is preferably from 1 to 5 hours. (Second step) 146960.doc • 21 - 201036941 At least an acidic aqueous solution is used to clean the reactants obtained after the reaction obtained in the above-mentioned step, or at least 60 t or more, The water below the hunger, the better, the better is to grab the above, 9 (the water below rc clean the The reaction product after the reaction. The cleaning of the reactants may be carried out by washing with an acid aqueous solution or by washing with water of 6 generations or more and 95° C. or less. The cleaning of the water of 6 〇〇c. The acidic aqueous solution herein is not particularly limited as long as it is a water-cooling liquid having a value of about 1 or less, and is preferably a hydrochloric acid aqueous solution, an acetic acid aqueous solution, or a sulfuric acid aqueous solution. The temperature at the time of cleaning the acidic aqueous solution is not particularly limited and may be any temperature, preferably 0 to 80. Preferably, 10 to 70 C' is particularly preferably 2 〇 to 6 〇. For water above 60 C and below 951, deionized water is preferred. Further, it is preferably 9 (water below TC, more preferably water of 85 r or less, more preferably 80 ° C or less. (Step 3) The cleaning product obtained in the above second step, that is, The sulfonamide compound is dried. The drying can be carried out by various methods such as natural drying, hot air drying, and reduced-pressure drying. For example, the temperature at the time of drying is preferably 4 〇 to 6 〇r. The time required for drying is preferably 8 to 24 hours, more preferably 12 to 18 hours. It is preferred to carry out the drying in such a manner that the water content in the sulfonamide compound is 3% or less, depending on the method used. The guanamine compound can be preferably used as a dye, especially a dye used in a color filter of a color filter array. 146960.doc -22- 201036941 That is, the coloring sensitivity of the sulfonamide compound as a pigment The resin composition can be suitably used as a photosensitive resin composition for forming a color filter. (Fourth step) In the method for producing a colored photosensitive resin composition according to the present invention, the first to third aspects are performed. After the step, as the fourth step, The sulfonamide compound is at least selected from the group consisting of pigment or pigment dispersion (B), solvent (C), resin (D), photopolymerization I1 biochemical (E), and photopolymerization initiator (ρ) — _ Mixing. Here, the sulfonamide compound may be directly mixed with the above components, but it is preferred to obtain a mixture with each component through a filter in at least two stages. For example, it can be enumerated by the following The fifth to seventh steps are mixed with the respective components or mixed with the respective components by performing the eighth to first steps. By performing the steps, the presence of the minute foreign matter can be suppressed to a simple method. At the minimum, it is possible to obtain a high-density fine color filter with a film thickness uniform film. Step 5: A dye solution containing a sulfonamide compound obtained by the above-described sulfonamide compound production method (Α) the step of passing through the second filter; 乂, the sixth step: passing the dye solution (a) after passing through the second pass through the second step; the seventh step: making the pass through the second pass Dye solution (A) after the device and selected from 146960.doc • 23· mixed with at least one of a pigment or a pigment dispersion (B), a solvent (C), a resin (D), a photopolymerizable compound (E), and a photopolymerization initiator (F). 201036941 Steps - Step 8. The dye solution (A) containing the sulfonamide compound obtained by the above-described method for producing the amine compound is passed through the third filter step: the third filter is passed The dye solution (A) after the device is selected from the group consisting of pigment or pigment dispersion (B), solvent (〇, resin (D), photopolymerizable compound (E), and photopolymerization initiator (F). At least one step of mixing 2 to obtain a mixture, the step of digesting the step of passing the mixture through the fourth filter. (Fifth Step) The dye solution (A) containing the phthalamide compound may be one or two or more solutions containing only the above-described hydrazine compound and the above-mentioned sevoamine compound: or may further contain one or two A solution of the above other solvent soluble dyes. The dye which is soluble in other solvents may be the same as those which are known to be soluble in the solvent. For example, Japanese Patent Laid-Open No. 64-90403, and Japanese Patent Laid-Open No. 64-9(10), Japanese Patent Laid-Open No. 9 Side Bulletin, Japanese Patent Laid-Open No. 6 wu, Japanese Special (4), No. 25922 (> 7, U.S. Patent No. 4, _, 5-1, U.S. Patent No. 5,667,92) , US Patent No. 9, No., Japanese Patent (4) Ping 5_3332 () No. 7 Pure, Japanese Patent Special Kaiping 6.3 Measurement Bulletin, Japanese Patent Special Kaiping 6_川15 Bulletin, Japanese Patent Special Kaiping 6_19 ～1 of the dyes/pigments described in the Gazette, etc. can be cold! · Bios', especially acid dyes, basic dyes, direct dyes, 146960.doc -24· 201036941 Sulphur dyes, anthraquinone dyes, naphthol dyes, reactivity Dyes, disperse dyes, etc. ', the chemical structure of the dye' can be any of the following structures: 吼 .. Azo system, anilino azo, aryl azo, pyrazolotriazole Nitrogen system: pyridone azo, triphenylmethane, Lanthanide, anthraquinone, anthraquinone, oxet, cyanine, polydecyl, morphine, pyrrole: pyrazole methine azo, Yamaguchi galaxies, eucalyptus a 'quinacridone oxime system, a benzopyranium system, an indigo system, a diterpenoid system, a coumarin system, a squarylium system, etc. A solvent for dissolving a dye in the dye solution (A) It may be water, but is preferably an organic solvent. For example, it can be selected from the following organic solvents: esters (solvents containing -COO-), ethers other than esters (solvents), and ketones other than esters. In the class (CO-containing/mixture), alcohols, aromatic hydrocarbons, guanamines, methylpyrrolidone, disulfoxide, etc. 〇 As the above-mentioned esters, for example, decyl lactate and lactic acid are mentioned. Ethyl ester, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate Ester, ethyl butyrate, butyl butyrate, methyl glycolate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, ethoxylate Formylacetate, ethyl ethoxyacetate, decyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxypropionic acid Ethyl ester, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, 2-ethoxypropionic acid Ethyl ester, 2-methoxy-2-methylpropionic acid 146960.doc -25- 201036941 methyl sulfonium, ethyl 2-ethoxy-2-propanoate, methyl pyruvate, propionic acid Ester, propyl pyruvate, methyl acetate, ethyl acetate, ethyl 2-oxobutyrate, ethyl 2-oxobutanoate, butyl 3-methoxyacetate, 3-methoxy Butyl-3-methylacetate, cyclohexanol acetate, γ-butyrolactone, and the like. As the above-mentioned shouts, the ethyl alcohol, the early riddle and the ethylene glycol monomethyl test can be exemplified by diethyl ether, ethylene glycol monopropyl ether, ethanol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl _, propylene glycol monopropyl ether, propylene glycol monobutyl ether, alcohol, 3-methoxy-3. methyl butanol, lactyl tetrahydrofuran, tetrahydrogen. Bitan, Μ〇烧, diethylene glycol dimethyl shark, - ethylene glycol diacetone, diethylene glycol methyl ether 'diethylene glycol dipropanol, two two..., propylene glycol monomethyl acetonitrile , propylene glycol single-accuracy B: - known as early propyl ether acetate, methyl cellosolve acetate fiber acetate, ethyl carbitol acetate acetate θ ethyl - a mystery, benzene, shout, methyl Benzene _ and so on. Cards, acetic acid vinegar, benzene as the above ketones' can be exemplified by: 4, acetone, 2-heptanone, 3-heptanone, 4-heptan-2-nonanone: bismuth, cyclopentamidine, cyclohexane, and Buddha _ and so on. Examples of the above-mentioned alcohols include, as the above-mentioned alcohols, an alcohol, a hexanol, a cyclohexanol, an ethylene glycol, a 'propanol', a tt, an inner alcohol, and a propylene glycol. Oh. Benzene, mesitylene, and the like. The present invention, the succinylamine and the diamine as the above-mentioned guanamines, for example, may be exemplified by: Μ Ν, Ν-dimethylacetamide, Ν_methyl oxime _, etc.: 146960.doc * 26 - 201036941 The solvent may be used singly or in combination of two or more. In the dye solution (increased, relative to the total amount of the dye solution, it is preferred to dissolve 1 to 30% by mass of the dye. It is preferred to add the agent to the dye solution (4) before passing through the device. Examples of the filter agent herein include diatomaceous earth, pearl 'expanded/alumina, acid white clay, kaolin, and Shiqi gum. Among them, diatomaceous earth, acid clay, and tannin extract are preferred. The (five) core to which the solution (4) has passed may be used without any particular limitation as long as it is used for filtration purposes, etc., for example, fluorocarbon tree such as PTFE (P〇lytetraflu〇rethylene, polytetrafluoroethylene) A filter formed of a polystyrene resin (including density, ultrahigh molecular weight) such as polyethylene or polypropylene (PP, p〇lypr〇pylene). The pore diameter of the first filtration is preferably 〇5~5 〇 More preferably, 〇·5 2.5 μηι, and even more preferably (^~丨5 μιη. By setting this range, the removal of the mixed dye into the dissolved dye will hinder the preparation of the uniform in the subsequent steps. a fine foreign matter or a self-coloring combination of the coloring composition The foreign matter on the coating film obtained by the object. In addition, the first sputum can be used only once, or the second sputum can be used for two people. Combination. The aperture here can refer to the nominal value of the filter manufacturer. As a commercially available filter, for example, from Japan Pall Co., Ltd., Advantec Toyo Co., Ltd., Japan Entegrjs Co., Ltd. (original My本 Mykr 〇lls Co., Ltd.) or various filters provided by Kitz Micro Filter Co., Ltd., etc. 146960.doc -27- 201036941 As a filtration method for passing the dye solution (A) through the 丨 filter, it can be cited as: After simmering, depressurizing and smashing (exhausting), pressure, etc. When the pressure is over, the pressure is preferably MPa. ' (Step 6) After passing through the third filter The dye solution (A) passes through the second passer. The second filter may be formed of the same material as the above-described second filter, etc. The second filter preferably has a pore diameter of 〇〇1 to 〇5 μπι. , better is called 'and thus better It is 〇〇1~〇". By setting it to = 粑', it is possible to remove the fine foreign matter which is mixed into the dissolved dye which hinders the preparation of a uniform coloring composition in the subsequent step, or obtained from the coloring composition. Foreign matter on the coating film. In particular, the aperture of the first transitional device and the aperture of the second filter are preferably set to 1:1 to 500:1 'better 2.5:1 to 250:1, and further More preferably, the filtration of the second filtration state can be carried out only once or twice or more. In addition, the second filter of different apertures in the above range can also be combined. The filtration method in the case where the mixed liquid is passed through the second filter is the same as the method in the case of passing the first filter. Among them, from the viewpoint of suppressing the incorporation of moisture or the like into the dye solution (Α) after passing through the filter, it is preferred that the mixed wave is passed through the filter by pressure filtration in a helium gas atmosphere. The pressure at the time of the pressure filtration is the same as the pressure at the time of passing through the second filter, and is preferably 0.0 U 〇 MPa. 146960.doc -28 * 201036941 (Step 7), the dye solution (A) after passing through the brother 1 and the second filter is selected from the pigment or pigment dispersion (B), the solvent (C), and the resin (D). At least one of the group consisting of the photopolymerizable compound (E) and the photopolymerization initiator (F) is mixed. From the viewpoint of reducing the foreign matter on the coating film obtained from the coloring composition, it is preferred to carry out the first step of the mixture obtained in the seventh step.

作為顏料或顏料分散液（B)中之顏料，只要為該領域中所使用者則並無特別限定，可使用任意顏料。顏料可為有機顏料及無機顏料之任一者，可列舉染料索 (Color IndexKThe Society of Dyers and Colourists * 中歸類為顏料（Pigment)之化合物。具體而言，可列舉：c. L顏料黃1、3、i2〜i7、2〇、 24、31、53、83、86、93、94、1〇9、no、117、125、 128、 137、 138、 139、 147、 148、 15〇、 153、 154、 166、 173 ' 194、214等黃色顏料； C. I.顏料橙 13、31、36、38、4〇、42、、η ' μ、 59、61、64、65、71、73 等橙色顏料； C. I.顏料紅 9、97、1〇5、122、123、144、149、166、 168 、 176 、 177 、 180 、 192 、 2〇9 、 215 、 216 、 224 、、 254、255、264、265 等紅色顏料； C. I.顏料藍 15、15:3、15:4、15:6、6〇等藍色顏料； C.I.顏料紫卜……^聯紫色顏料； c· I.顏料綠7、36等綠色顏料； C.1.顏料棕23、25等棕色顏料； 146960.doc -29· 201036941 c. I.顏料黑1、7等黑色顏料等。其中，較好者可列舉：c. ι·顏料藍15、15:3、15 4 ' 15:6、60等藍色顏料；c. L顏料紫丨、19、23、n 36、38等紫色顏料等。其中，較好的是含有選自$ 料务、23、C. I·顏料藍15:3、15:6中之至少，〈主v 種顏料，特別好的是含有C. !.顏料藍15:6。該等顏料可單獨使用，亦可混合兩種以上來使用。亦可視需要對該等顏料中之有機顏料實施以下之處理：松香處理，使用導入有酸性基或驗性基之顏料衍生物或顏料分散劑等之表面處理，利用高分子化合物等對顏料表面進打之接枝處理，利用硫酸微粒化法等之微粒化處理或者用：去除雜質之利用有機溶劑或水等之清洗處理，利用離子父換法等去除離子性雜質之處理等。有機顏料較好的是粒徑 —八卫勺q 藉由含有顏料分散劑而進分散、^ 1卩獲得顏料於溶液中均勾分散之狀態之顏料 ❹ 好的疋分散於分散劑+。其原因在於可容易地製傷均勾之分散狀態之著色組合物。作為顏料分散劑離早备則例如可列舉陽離子系、陰離子系、非 fli $ ^ =眭、承酯系、聚胺系、丙烯酸系等之界面活性用。4寺顏料分散劑可單獨使用，亦可組合以便用。具體而言，可列舉. 苯_ in L ⑽基㈣、聚氧乙稀烧基 —s曰類、山梨醇酐脂肪酸酯類、脂肪酸 146960.doc -30. 201036941 改質聚酯類、三級胺改質聚胺基甲酸酯類、聚乙烯亞胺類等，具體之商品名可列舉：kp(信越化學工業（股）製造）、 Polyflow(共榮社化學（股）製造）、Eftop(Mitsubishi Materials Electronic Chemicals(股）製造）、Megaface(DIC(股）製造）、 Fluorad(住友3M(股）製造）' AsahiGuard(旭硝子（股）製造）、 Surflon(AGC Seimi Chemical(股）製造）、Solsperse(Zeneca(股）製造）、EFKA(CIBA公司製造）、Ajisper(味之素（股）製造）、Disperbyk(BYK Chemie公司製造）等。分散劑相對於每1質量份之顏料較好的是1質量份以下，更好的是0.05〜0.5質量份。藉由將分散劑之使用量設定為該範圍内，可獲得均勻之分散狀態之顏料分散液。染料溶液（A)中之染料與顏料或顏料分散液（B)中所含有之顏料的比率以質量基準計較好的是1:99~99:1，更好的是 1:99〜60:40，進而更好的是5:95〜40:60。藉由設定為如此之比率，可獲得容易使透射光譜最合適化，並可形成高對比度、高亮度之塗膜或圖案的著色組合物。並且，包含著色組合物之塗膜或圖案之耐熱性、耐化學品性變得良好。尤其是於使用C· I.顏料藍15:6之情形時，與染料之質量比較好的是97:3〜50:50。作為溶劑（C)，可列舉與作為染料溶液（A)之溶劑而例示的水或有機溶劑相同者。作為樹脂（D)，並非僅指聚合物，亦可包含共聚物、低聚物等以及/或者聚合性或交聯性等之單體（其中，以下之光聚合性化合物（E)除外），只要為可構成樹脂之單元即 146960.doc -31· 201036941 可。作為樹脂（D)，例如較好的是鹼溶性之樹脂。例如’驗溶性樹脂含有源自（？基）丙烯酸之結構單元。此處’（甲基）丙烯酸表示丙烯酸及/或甲基丙稀酸。源自（甲基）丙烯酸之結構單元之含量較好的是於構成驗溶性樹脂之全部結構單元中為i 6莫耳％以上、4 g莫耳％以下’更好的是18莫耳％以上、38莫耳％以下。若源自:甲基）丙締酸之結構單元之含量處於該範圍内，則顯影時非像素部之溶解性良好。X，存在顯影後之非像素部中難以殘留殘渣之傾向，故而較好。作為導入構成鹼溶性樹脂的除源自（甲基）丙烯酸之結構單元以外之結構單元的其他單體，例如可列舉：芳香族乙烯化合物、不飽和羧酸酯類、不飽和羧酸胺基烷基酯類、不飽和羧酸縮水甘油酯類、羧酸乙烯酯類、不飽和醚類、氰乙烯化合物、不飽和醯胺類 '不飽和醯亞胺類、脂肪族共軛二烯類、聚合物分子鏈之末端具有單丙烯醯基或單甲基丙烯醯基之巨單體類、式（II)所示之單元及式（ΙΠ)所示之單元等。The pigment in the pigment or pigment dispersion (B) is not particularly limited as long as it is used in the art, and any pigment can be used. The pigment may be any of an organic pigment and an inorganic pigment, and examples thereof include a dye which is classified as a pigment in Color Index K The Society of Dyers and Colourists *. Specifically, c. L Pigment Yellow 1 , 3, i2~i7, 2〇, 24, 31, 53, 83, 86, 93, 94, 1〇9, no, 117, 125, 128, 137, 138, 139, 147, 148, 15〇, 153 , 154, 166, 173 '194, 214 and other yellow pigments; CI pigment orange 13, 31, 36, 38, 4 〇, 42, η 'μ, 59, 61, 64, 65, 71, 73 and other orange pigment; CI Pigment Red 9,97,1〇5,122,123,144,149,166,168,176,177,180,192,2,9, 215, Red pigment; CI pigment blue 15, 15:3, 15:4, 15:6, 6〇 and other blue pigments; CI pigment purple b... ^ violet pigment; c · I. pigment green 7, 36 and other green pigments ; C.1. Brown pigments such as pigment brown 23, 25; 146960.doc -29· 201036941 c. I. Pigment black 1, 7 and other black pigments, etc. Among them, preferred ones are: c. ι·Pigment blue 15 15:3 , 15 4 '15:6, 60 and other blue pigments; c. L pigment purpura, 19, 23, n 36, 38 and other purple pigments, etc. Among them, it is preferred to contain from the choice of materials, 23, C I. Pigment Blue at least 15:3, 15:6, <Main v kinds of pigments, particularly preferably containing C.!. Pigment Blue 15:6. These pigments may be used alone or in combination of two or more. The organic pigment in the pigments may be subjected to the following treatments as needed: rosin treatment, surface treatment using a pigment derivative or a pigment dispersant introduced with an acid group or an experimental group, using a polymer compound or the like The grafting treatment of the surface of the pigment is carried out by a micronization treatment such as a sulfuric acid micronization method or a cleaning treatment using an organic solvent or water for removing impurities, and the treatment of removing ionic impurities by an ion parent substitution method or the like. The pigment is preferably a particle size-eight-dimensional spoon q which is dispersed in a pigment-dispersing agent to obtain a pigment in which the pigment is dispersed in a solution, and is preferably dispersed in a dispersing agent +. a color group that can easily damage the dispersed state of the hook Thereof. As early as a pigment dispersant prepared from, for example, include the cationic, anionic, non-fli $ ^ = Sui, bearing ester, polyamine, acrylic, etc. with a surfactant. 4 Temple pigment dispersants can be used alone or in combination. Specific examples include benzene_in L (10)-based (tetra), polyoxyethylene-based s-hydrazine, sorbitan fatty acid esters, and fatty acids 146960.doc -30. 201036941 Modified polyesters, tertiary amines Modified polyurethanes, polyethyleneimine, etc., and the specific trade names include kp (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow (manufactured by Kyoeisha Chemical Co., Ltd.), and Eftop (Mitsubishi Materials). Electronic Chemicals (manufactured by Electronic Chemicals), Megaface (manufactured by DIC), Fluorad (manufactured by Sumitomo 3M), AsahiGuard (made by Asahi Glass), Surflon (made by AGC Seimi Chemical), Solsperse (Zeneca) (manufacturing), EFKA (manufactured by CIBA Co., Ltd.), Ajisper (manufactured by Ajinomoto Co., Ltd.), Disperbyk (manufactured by BYK Chemie Co., Ltd.), and the like. The dispersant is preferably 1 part by mass or less, more preferably 0.05 to 0.5 part by mass per 1 part by mass of the pigment. By setting the amount of the dispersant to be within this range, a pigment dispersion liquid in a uniformly dispersed state can be obtained. The ratio of the dye in the dye solution (A) to the pigment contained in the pigment or pigment dispersion (B) is preferably from 1:99 to 99:1, more preferably from 1:99 to 60:40. And then better is 5:95~40:60. By setting such a ratio, a coloring composition which is easy to optimize the transmission spectrum and which can form a coating film or pattern having high contrast and high brightness can be obtained. Further, the heat resistance and chemical resistance of the coating film or pattern including the coloring composition are good. Especially in the case of using C·I. Pigment Blue 15:6, the quality of the dye is preferably 97:3 to 50:50. The solvent (C) is the same as the water or the organic solvent exemplified as the solvent of the dye solution (A). The resin (D) is not limited to a polymer, and may include a copolymer, an oligomer, and the like, and/or a monomer having polymerizability or crosslinkability (excluding the photopolymerizable compound (E) below). As long as it is a unit that can constitute a resin, 146960.doc -31· 201036941 can be used. As the resin (D), for example, an alkali-soluble resin is preferred. For example, the test resin contains a structural unit derived from (?) acrylic acid. Here, '(meth)acrylic acid means acrylic acid and/or methacrylic acid. The content of the structural unit derived from (meth)acrylic acid is preferably i 6 mol% or more and 4 g mol% or less in all the structural units constituting the test resin. More preferably, it is 18 mol% or more. 38% or less. When the content of the structural unit derived from the methyl group of propionic acid is within this range, the solubility in the non-pixel portion at the time of development is good. X is preferable because it tends to have no residue remaining in the non-pixel portion after development. Examples of the other monomer which is a structural unit other than the structural unit derived from (meth)acrylic acid which is an alkali-soluble resin may be an aromatic vinyl compound, an unsaturated carboxylic acid ester or an unsaturated carboxylic acid aminoalkyl group. Base esters, unsaturated carboxylic acid glycidyl esters, vinyl carboxylates, unsaturated ethers, cyanoethylene compounds, unsaturated guanamines, 'unsaturated quinones, aliphatic conjugated dienes, polymerization The terminal of the molecular chain has a monomethicone or a monomethacrylinyl macromonomer, a unit represented by the formula (II), a unit represented by the formula (ΙΠ), and the like.

HO R53HO R53

(H)(H)

R55R55

(III) (、式（II)及式（III)中，R53及R55分別獨立表示氫原子或曱 146960.doc -32- 201036941 基。R54及R56分別獨立表示氫原子或碳數為工—6之烷基）作為驗溶性樹脂，具體而言可列舉：甲基丙烯酸/甲基丙烯酸苄酯共聚物、甲基丙烯酸/甲基丙烯酸苄酯/苯乙烯共聚物、曱基丙烯酸/曱基丙烯酸苄酯/甲基丙烯酸異葙酯共聚物、甲基丙烯酸/苯乙烯/曱基丙烯酸节酯/N_苯基順丁烯二醯亞胺共聚物、甲基丙烯酸/式（11)所示之構成成分（其中，式（II)中R53表示甲基，R54表示氫原子）/甲基丙烯酸苄酯共聚物、式（II)所示之構成成分（其中，式（Π)中R53表示甲基，R54表示氫原子）/曱基丙烯酸苄酯共聚物、曱基丙烯酸/式（ΙΠ)所示之構成成分（其中，式（ΠΙ)中r55表示甲基， R56表示氫原子）/苯乙烯共聚物/甲基丙烯酸三環癸酯共聚物、以及式（IV)所示之鹼溶性樹脂（B)等。(III) (In formula (II) and formula (III), R53 and R55 each independently represent a hydrogen atom or a ruthenium 146960.doc -32- 201036941. R54 and R56 independently represent a hydrogen atom or a carbon number. The alkyl group) Specific examples of the solvent-soluble resin include methacrylic acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene copolymer, and methacrylic acid/benzyl methacrylate. Ester/isodecyl methacrylate copolymer, methacrylic acid/styrene/mercapto butyl acrylate/N-phenyl maleimide copolymer, methacrylic acid/formula (11) a component (wherein R53 represents a methyl group in the formula (II), R54 represents a hydrogen atom) / a benzyl methacrylate copolymer, and a component represented by the formula (II) (wherein R53 represents a methyl group in the formula (Π); R54 represents a hydrogen atom) / benzyl methacrylate copolymer, a mercapto acrylate / a component represented by the formula (wherein, r55 represents a methyl group, and R56 represents a hydrogen atom) / styrene copolymer /tricyclodecyl methacrylate copolymer, and alkali-soluble resin (B) represented by formula (IV)

含有式（II)所示之構成成分之驗溶性樹脂、例如甲基丙烯酸/式（Π)所示之構成成分（其中，式（II)中R53表示甲基）/ 甲基丙烯酸苄酯共聚物可藉由使甲基丙烯酸與曱基丙婦酸苄酯聚合而獲得共聚物’然後使所獲得之共聚物與式（V) 所示之化合物反應而獲得。〇A test resin containing a component represented by the formula (II), for example, a methacrylic acid/component represented by the formula (wherein R53 represents a methyl group in the formula (II)) / a benzyl methacrylate copolymer The copolymer can be obtained by polymerizing methacrylic acid with benzyl mercaptopropyl benzoate and then reacting the obtained copolymer with a compound represented by the formula (V). 〇

(V) 146960.doc -33- 201036941 (式（V)中，R54表示與上述相同之含義） f基丙烯酸/式（ΠΙ)所示之構成成分（其中，式（ni)$R55 表示甲基）/苯乙烯共聚物/曱基丙烯酸三環癸酯共聚物可藉由使甲基丙烯酸苄酯、甲基丙烯酸、單甲基丙烯酸三環癸酯共聚物與式（VI)所示之化合物反應而獲得。 (VI) 八聚通常係使用聚合起始劑於溶劑中進行。作為聚合起始劑，例如可使用：2,2，_偶氮二異丁猜或匕’2 氮雙(2_曱基丙酸甲酯)之類的偶氮化合物，以及過氧化苯甲1敗或第二丁基過氧化物之類的過氧化物等。溶劑只要可溶解各單體即可’例如可使用：乙二醇 _乙酸酯、乙二酿置 * _早***乙酸酯、丙二醇單甲醚乙酸酯' 丙一醇單乙喊乙酿gt + h ^ ⑻而例_ 日之4的二醇㈣類，下述之作為溶劑(V) 146960.doc -33- 201036941 (in the formula (V), R54 represents the same meaning as above) f-based acrylic acid / a compound represented by the formula (ΠΙ) (wherein (ni) $R55 represents a methyl group / styrene copolymer / tridecyl methacrylate copolymer can be reacted with a compound represented by formula (VI) by copolymerizing benzyl methacrylate, methacrylic acid, tricyclodecyl monomethacrylate And get. (VI) Octapolymer is usually carried out in a solvent using a polymerization initiator. As the polymerization initiator, for example, an azo compound such as 2,2,-azobisisobutyl or 匕'2 bis(2-methylpropionate), and benzoyl peroxide 1 can be used. A peroxide or a peroxide such as a second butyl peroxide. The solvent can be used as long as it can dissolve the monomers. For example, ethylene glycol-acetate, ethylene dioxide* _ early ether acetate, propylene glycol monomethyl ether acetate can be used. Gt + h ^ (8) and _ diol 4 (four), the following as a solvent

(E)而例不之溶劑等。片J(E) Solvents and the like. Piece J

反應溫度可I壶取A 沸點等而決1起始劑之分解溫度或溶劑及單體之亦可利用具有聚合性基之化八物對以卜、+. 獲得之共聚物之側鏈、卜化。物對以上迷方式所脂。此時，亦卩改質’而製成感光性之鹼溶性樹媒。 ^用於將聚合性基導人至樹脂中之觸作為觸媒，你丨^ 又，亦可添加用於^防可二舉三（二甲基胺基甲基）苯盼等。副反應之添加劑。作為添加劑，例 146960.doc •34- 201036941 如可列舉對苯二酚等。作為樹脂（D)，例如亦可使用以下之共聚物[Κ1]〜[κ4] 等。 • [κι]將不飽和羧酸及/或不飽和羧酸酐（Β1)(以下，有時 . 間稱為（Β 1 )」）與具有後數為2〜4之環狀鱗結構之單體 (Β2)(以下，有時簡稱為「（Β2)」）聚合而成之共聚物。 [Κ2]將（Bl)、（Β2)及單體（Β3)聚合而成之共聚物。此 ◎ 處，單體⑺3)(以下，有時簡稱為「（Β3)」）係可與（Β1)&/ 或（Β2)共聚合且不為（Bi)及/或（Β2)之單體。 [Κ3]使（Β1)與（Β3)之共聚物中源自（Β1)之羧基之一部分與源自（Β2)之碳數為2〜4之環狀醚結構反應而獲得之共聚物0 [Κ4] (Β1)與（Β3)之共聚物。其中，較好的是將至少（Β1)與（Β2)聚合而成之共聚物。作為（Β 1 )，例如可列舉脂肪族不飽和缓酸及/或脂肪族不〇飽和羧酸酐等。具體而言，可列舉：丙烯酸、曱基丙烯酸、丁烯酸等不飽和單羧酸類；順丁浠一酸、反丁烯二酸、擰康酸、中康酸、衣康酸等 •不飽和二羧酸類；及順丁烯二酸酐、檸康酸酐、衣康酸酐、3_乙烯基鄰苯二甲酸酐、4-乙烯基鄰苯二曱酸酐、3,4,5,6-四氫鄰苯二甲酸酐、1，2,3,6-四氫鄰苯二曱酸酐、二曱基四氫鄰苯二甲酸酐、5,6-二羧基雙環[2.2.1]庚-2-烯酐（雙環庚烯二甲酸酐）等不飽和二羧酸類之酐； 146960.doc -35- 201036941 丁一酸單[2-(甲基）丙浠酸氧基乙基]醋、鄰苯二曱酸單 [2-(甲基）丙烯醯氧基乙基]酯等二元以上之多元羧酸之不飽和單[(甲基）丙烯醯氧基烷基]酯類； 5_羧基雙環[2.2.1]庚-2-烯、5,6-二羧基雙環[2.2.1]庚_2_ 烯、5-羧基-5_甲基雙環[221]庚_2_烯、5_羧基_5_乙基雙環[2.2.1]庚-2-烯、5-羧基-6-甲基雙環[2.2.1]庚-2-烯、5-綾基-6-乙基雙環[^^庚_2_烯等含羧基之雙環[2 2丨]庚_2_ 烯類；以及 α-(羥甲基）丙烯酸等同一分子中含有羥基及羧基之不飽和丙浠酸酯類等。其中，就共聚反應性及鹼溶解性之觀點而言，較好的是丙烯酸、甲基丙烯酸或順丁烯二酸酐等。該等可單獨使用、或者組合兩種以上來使用。再者，於本說明書+，只要無特別說明，則所例示之化合物、成分、化學劑等均可單獨使用或者組合兩種以上來使用。 (Β2)例如只要具有選自由碳數為2〜4之環狀醚結構（例如環氧乙烷基、環氧丙烷基及四氫呋喃基)所組成群中的至少-種基即彳，更好的是具有不飽和鍵之單體。作為 (Β2)’更好的是具有碳數為2〜4之環狀⑽結構及乙婦性碳_ 碳不飽和鍵之單體，特別好的是具有碳數為2〜4之環狀醚結構及（甲基）丙烯醯氧基之單體。作為_，例如可列舉：具有環氧乙燒基之單體、具有環氧丙烧基之單體、具有四氫Π夫喃基之單體等。上述具有環氧乙烷基之單體例如俜指你知具有選自由脂肪族 146960.doc -36- 201036941 %氧乙炫基及腊環式環氧乙烷基所組成群中之至少—種基的聚合性化合物。具有環氧乙燒基之單體較好的是具有選自由脂肪族環氧 • 乙烧基及脂環式環氧乙烷基所組成群中之至少一種基，且具有不飽和鍵的化合物。所謂脂肪族環氧乙烷基，係指具有將鏈式烯烴環氧化而成之結構之基。 ❹ 作為具有脂肪族環氧乙烷基之化合物，具體而言可列舉.（甲基）丙烯酸縮水甘油酯、（曱基）丙烯酸p_甲基縮水甘油酯、（曱基）丙烯酸β_乙基縮水甘油酯、縮水甘油基乙烯醚、曰本專利特開平7_248625號公報中所記載之下述式 (VI)所示之化合物等。The reaction temperature can be I, the boiling point of A, etc., and the decomposition temperature of the initiator, or the solvent and the monomer, and the side chain of the copolymer obtained by using the polymerizable group. Chemical. The thing is fat to the above ways. At this time, it is also modified to produce a photosensitive alkali-soluble medium. ^ Used to introduce the polymerizable group into the touch of the resin. As a catalyst, you can also add it to prevent the tris(dimethylaminomethyl)benzene. Additive for side reactions. As an additive, an example is 146960.doc • 34- 201036941 Examples include hydroquinone and the like. As the resin (D), for example, the following copolymers [Κ1] to [κ4] can be used. • [κι] a monomer having an unsaturated carboxylic acid and/or an unsaturated carboxylic anhydride (Β1) (hereinafter, sometimes referred to as (Β 1 ))) and a cyclic scaly structure having a number of 2 to 4 (Β2) (hereinafter, abbreviated as "(Β2)") a copolymer obtained by polymerization. [Κ2] A copolymer obtained by polymerizing (Bl), (Β2) and a monomer (Β3). Here, the monomer (7) 3) (hereinafter sometimes abbreviated as "(Β3)")) may be copolymerized with (Β1)&/ or (Β2) and is not a single (Bi) and/or (Β2) body. [Κ3] A copolymer obtained by reacting a part of a carboxyl group derived from (Β1) with a cyclic ether structure derived from (Β2) having a carbon number of 2 to 4 in a copolymer of (Β1) and (Β3) [ Κ4] (共聚物1) and (Β3) copolymer. Among them, a copolymer obtained by polymerizing at least (Β1) and (Β2) is preferred. Examples of (Β 1 ) include an aliphatic unsaturated acid and/or an aliphatic unsaturated carboxylic anhydride. Specific examples thereof include unsaturated monocarboxylic acids such as acrylic acid, mercaptoacrylic acid, and crotonic acid; cis-butyric acid, fumaric acid, tococanic acid, mesaconic acid, itaconic acid, etc. • unsaturated Dicarboxylic acids; and maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydroortene Phthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimercaptotetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride (Bicycloheptene dicarboxylic anhydride) and other unsaturated dicarboxylic acid anhydrides; 146960.doc -35- 201036941 butyric acid mono [2-(methyl)propionate oxyethyl] vinegar, phthalic acid Unsaturated mono[(meth)propenyloxyalkyl]esters of dihydric or higher polycarboxylic acids such as mono[2-(methyl)acryloxyethyl]ester; 5-carboxyl bicyclo[2.2. 1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[221]hept-2-ene, 5-carboxyl_5_B Bicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-nonyl-6-ethylbicyclo[^^hept-2-ene Carboxyl group Containing a hydroxyl group and an unsaturated carboxyl and propionic acid esters and the like as well as Hay alpha] (hydroxymethyl) acrylate and the like in the same molecule; bicyclo [22 Shu] hept-based _2_. Among them, acrylic acid, methacrylic acid or maleic anhydride is preferable from the viewpoint of copolymerization reactivity and alkali solubility. These may be used alone or in combination of two or more. In addition, in the present specification, the compound, the component, the chemical agent, and the like which are exemplified may be used singly or in combination of two or more kinds unless otherwise specified. (Β2) For example, it is preferable to have at least one group selected from the group consisting of a cyclic ether structure having a carbon number of 2 to 4 (for example, an oxiranyl group, an oxypropylene group, and a tetrahydrofuranyl group). It is a monomer having an unsaturated bond. More preferably, (Β2)' is a monomer having a ring (10) structure having a carbon number of 2 to 4 and an ethylarene carbon-carbon unsaturated bond, and particularly preferably a cyclic ether having a carbon number of 2 to 4. Structure and monomer of (meth) propylene decyloxy group. The _, for example, a monomer having an ethylene oxide group, a monomer having a propylene oxide group, a monomer having a tetrahydrofuranyl group, and the like. The above monomer having an oxirane group, for example, 你 means that it has at least one selected from the group consisting of aliphatic 146960.doc -36-201036941% oxyethylidene and waxy oxirane group. Polymeric compound. The monomer having an epoxy group is preferably a compound having at least one selected from the group consisting of aliphatic epoxy groups and alicyclic oxiran groups, and having an unsaturated bond. The aliphatic oxiranyl group means a group having a structure in which a chain olefin is epoxidized. ❹ As the compound having an aliphatic oxirane group, specifically, glycidyl (meth)acrylate, p-methylglycidyl (mercapto)acrylate, and β-ethyl of (mercapto)acrylic acid may be mentioned. A compound represented by the following formula (VI), which is described in JP-A-H07-248625, is a glycidyl ester, a glycidyl vinyl ether, and the like.

❹ (式（VI)中，R61〜R63分別獨立為氫原子或碳原子數丨〜⑺之烷基及環烷基，m1為1〜5之整數）。作為式（VI)所示之化合物，例如可列舉：鄰乙稀基节芙縮水甘油醚、間乙烯基苄基縮水甘油醚、對乙稀基节某縮水甘油醚、a-甲基-鄰乙烯基苄基縮水甘油醚、甲基-間❹ (In the formula (VI), R61 to R63 are each independently a hydrogen atom or an alkyl group having a carbon number of 丨~(7) and a cycloalkyl group, and m1 is an integer of 1 to 5). Examples of the compound represented by the formula (VI) include o-ethendyl glycidyl ether, m-vinylbenzyl glycidyl ether, a glycidyl ether of a vinyl group, and a-methyl-o-ethylene. Glyoxyl glycidyl ether, methyl-inter

鍵' 2,3-二縮水甘油氧基甲基苯乙烯、2,4_二縮水甘油氧基曱基苯乙烯、2,5-二縮水甘油氧基曱基苯乙烯、2,6-二 146960.doc -37- 201036941 縮水甘油氧基曱基苯乙稀、2,3,4_ 乙烯、2,3 5- = & & #择 '、’水甘油氧基甲基苯 —&水甘油軋基甲基苯乙油氧基甲基笨乙烯、3 4 s & 烯2,3,6·二縮水甘歸3,4,5-—縮水甘油氧 2从三縮水甘油氧基f基苯乙稀等。乳基甲基本乙知、所謂脂環式環氧乙院基’係指具有將成之結構之基。，衣式埽烴％氧化而作為具有料式環氧乙㈣之單體脂肪族單環式環备可列舉·具有乙烧基之單體等Γ 體、具有脂肪族多環式環氧有將單環性族單環式環氧乙-基，係指具脂肪族多環式^ = 成之結構之基。又，所謂環氧化而= 基’係指具有將多環性之環式稀烴衣乳化而成之結構之的是具有選自由脂肪族單環/式環氧院基之單體較好基所組成群中之至小一^式衣乳基及月旨肪族多環式環氧妊的H ^種，且具有不飽和鍵的化合物，更氧其戶^成^自由脂肪族單環切氧基及脂肪族多環式環化:物中之至少—種，且具有（甲基）丙烯酿氧基的己性之環式稀煙’例如可列舉:環戊㈣化合物。4辛稀等。其中，較好的是碳數為5〜7之可=具有⑽之單趙，… 乳化乙烯基％己烯（1，2_環氧基 -；--eI1〇xide 2〇〇0,·〇Μ,^Λ)；^：稀U，4—環氧環己基甲峨如，加。而錢〇 ; W祕 146960.doc •38· 201036941 c學項股)製造)、甲基_，4-環氧環己基甲醋(例如，咖〇聽购0;Daicel化學工業（股）製造）等。性之環式婦煙’例如可列舉:二環戊稀、二μ稀、降伯烯、異㈣烯、雙環辛烯、雙環環十一烯、三環十一烯、雙 _ 雙衣十一烯、二環十二烯等。其中，較好的是碳數為8〜12之化合物。 Ο ❹ 作為具有脂肪族多環式環氧W基之單體，例如可列舉選自由丙婦酸3’4_環氧基降宿醋、甲基丙降宿醋、式㈤)所示之化合物以及式(彻)所示之化= 所組成群中之至少一種化合物等。 h2c=c-Key '2,3-diglycidoxymethylstyrene, 2,4-diglycidyloxymercaptostyrene, 2,5-diglycidyloxymercaptostyrene, 2,6-di 146960 .doc -37- 201036941 Glycidyloxymercaptostyrene, 2,3,4_ethylene, 2,3 5- = &&&#择','Glycidoxymethylbenzene-& Rolling methyl phenyl ethoxymethyl acetophenone, 3 4 s & ene 2,3,6 · dimethylglycine 3,4,5--glycidyloxy 2 from triglycidyloxyf-phenyl Ethylene and so on. The urethane methyl group, the so-called alicyclic epoxy group, means a group having a structure to be formed. 5% of the monomeric aliphatic monocyclic ring having the epoxy group of the epoxy group (IV), a monomer having an ethyl group, and an aliphatic polycyclic epoxy. Monocyclic monocyclic epoxy B-group refers to a group having an aliphatic polycyclic ring structure. Further, the term "epoxidation" and "base" means a structure obtained by emulsifying a polycyclic ring-shaped thin hydrocarbon coat having a monomer selected from an aliphatic monocyclic/epoxy group. In the group consisting of the small one-type clothing-based milk base and the moon-shaped aliphatic polycyclic epoxy resin H ^ species, and compounds with unsaturated bonds, more oxygen, their own ^ ^ free aliphatic monocyclic oxygen The cyclopentane (tetra) compound is exemplified by at least one of the aliphatic polycyclic cyclization and the cyclopentanthene having a (meth)acryloyloxy group. 4 rarity and so on. Among them, it is preferred that the carbon number is 5 to 7, and the one having the (10), Zhao Zhao, ... emulsified vinyl % hexene (1, 2_epoxy-; - eI1〇xide 2〇〇0, · 〇 Μ, ^Λ); ^: Dilute U, 4-epoxycyclohexylmethyl hydrazine, for example. And Qian Wei; W secret 146960.doc •38· 201036941 c-study shares), methyl _, 4-epoxy cyclohexyl ketone (for example, curry buy 0; Daicel Chemical Industry Co., Ltd.) Wait. Examples of the ring-type women's cigarettes include: dicyclopentene, di-thin, norbornene, iso(tetra)-ene, bicyclooctene, bicyclocycloundecene, tricycloundecene, bis-double coat eleven Alkene, bicyclododecene, and the like. Among them, preferred are compounds having a carbon number of 8 to 12. Ο ❹ As the monomer having an aliphatic polycyclic epoxy group W, for example, a compound selected from the group consisting of 3'4-epoxy acetonate, methyl propyl vinegar, and formula (5)) And a compound represented by the formula (completely) = at least one compound in the group, and the like. H2c=c-

=c一c一ς 於式（νπ)及式（VIII)中，r7，及r72分別獨立表示氣原子或可由羥基取代之碳數為丨〜4之烷基。 X及X分別獨立表示單鍵、-Χ73_、*_χ73 〇 *-X73-S-X74_、*_χ73_ΝΗ —χ74 73 'Χ X及X表不碳數 6 烷二基。 *表示與0之結合鍵。作為R71及R72 ’具體而言，可列舉：氫原子；甲美、乙基、正丙基、異丙基、正丁基、第二丁基、第三丁基等烷基；土凡羥基曱基、1-羥基乙基' 2-羥基乙基、丨_羥基丙美、2 羥基丙基、3-羥基丙基、1_羥基-1-f基乙基、入羚美〗甲 146960.doc •39- 201036941 2-羥基丁基、3_羥基丁基、扣羥基基乙基、1 -經基丁基、丁基等羥基取代烷基。其中，較好的是氫原子、甲基、經基甲基、i，基乙基、2-羥基乙基。更好的是氫原子、甲基。作為烷二基’可列舉：亞甲基、伸乙基、1，2-丙二基、 1,3_丙二基、M_ 丁二基' 戊二基、1,6-己二基等。作為X71及X72,較好者可列舉：單鍵、亞甲基、伸乙基、*-CH2_0-(*表示與〇之結合鍵）基、*_CH2CH2_〇-基，更好者可列舉：單鍵、*-CH2CH2-〇·^。選自由式（VII)所示之化合物、及式所示之化合物所組成群中的至少一種化合物較好的是選自由下逑式 (Vir)所示之化合物、及式（VIir)所示之化合物所組成群中的至少一種化合物。=c - c - 于 In the formula (νπ) and the formula (VIII), r7, and r72 each independently represent a gas atom or an alkyl group having a carbon number of 丨~4 which may be substituted by a hydroxyl group. X and X respectively represent a single bond, -Χ73_, *_χ73 〇 *-X73-S-X74_, *_χ73_ΝΗ-χ74 73 'Χ X and X are not carbon number 6 alkanediyl. * indicates a bond with 0. Specific examples of R71 and R72' include a hydrogen atom; an alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl or t-butyl; Base, 1-hydroxyethyl '2-hydroxyethyl, hydrazine-hydroxy propyl methacrylate, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-f-ethyl, into the antelope 甲 146960.doc • 39- 201036941 2-hydroxybutyl, 3-hydroxybutyl, hydroxyethyl, 1-hydroxybutyl, butyl, etc., substituted alkyl. Among them, preferred are a hydrogen atom, a methyl group, a methyl group, an i group, a ethyl group, and a 2-hydroxyethyl group. More preferred are hydrogen atoms and methyl groups. The alkanediyl group may, for example, be a methylene group, an ethylidene group, a 1,2-propyldiyl group, a 1,3-propylenediyl group, an M-butylene group, a pentanediyl group or a 1,6-hexanediyl group. Preferred examples of X71 and X72 include a single bond, a methylene group, an ethylidene group, a *-CH2_0- (* represents a bond to a fluorene bond) group, and a *_CH2CH2_〇- group. Single key, *-CH2CH2-〇·^. At least one compound selected from the group consisting of a compound represented by the formula (VII) and a compound represented by the formula is preferably selected from the group consisting of a compound represented by the formula (Vir) and a formula (VIir). At least one compound of the group consisting of the compounds.

於式（VII，）及式（VIII，）中，RW及R72,之含義分別與上述 R71及R72相同。作為式（vii)所示之化合物，例如可列舉式（¥11_〗）〜式 (VII-15)所示之化合物等。較好的是式（VIM)、式（VII_ 3)、式（VII-5)、式（VII-7)、式（VII-9)、式（VII-11)〜式（VII-15)。更好的是式（VII-1)、式（VII-7)、式（VII-9)、式（VII-15)。 146960.doc -40- 201036941 ΟIn the formulae (VII,) and (VIII), RW and R72 have the same meanings as those of R71 and R72, respectively. The compound represented by the formula (vii) may, for example, be a compound represented by the formula (¥11_) to the formula (VII-15). Preferred are the formula (VIM), the formula (VII-3), the formula (VII-5), the formula (VII-7), the formula (VII-9), and the formula (VII-11) to the formula (VII-15). More preferred are formula (VII-1), formula (VII-7), formula (VII-9), and formula (VII-15). 146960.doc -40- 201036941 Ο

H2C:CH-c—〇_c2H4. ^H3 O H2C=C—C-0-CH2?H3 O H2C==C'—C-0-C2H4 ο H2C!CH'C'-o-c2h4-〇 CHjO H2〇=C—.A c—oH2C:CH-c—〇_c2H4. ^H3 O H2C=C—C-0-CH2?H3 O H2C==C'—C-0-C2H4 ο H2C!CH'C'-o-c2h4-〇CHjO H2〇=C—.A c—o

；Vn-7);Vn-7)

h2c=〇· ch3 o -c—0—C2H4-O-H2c=〇·ch3 o -c—0—C2H4-O-

Wn-11) ?H2〇H 〇 H2C=C--- TY V/0 / 人、/(VII-12) /(VII-13) C2H4OH 0 ry° h2c=c-_»_ vy J^y(vn-15) U vn-14) 作為式（VIII)所示之化合物，例l -r L. J 1 列如可列舉式（VIII-1)〜式 (VIII-15)所示之化合物專。較好的是式、式 3)、式（VIII-5)、式（VIII-7)、式（νΙΠ_9)、式（vni_u)〜式 Q (VIII-15)。更好的是式（VIII-1)、式（VIII-7)、式（VIII-9)、式 (VIII-15)。 • 41- 146960.doc 201036941Wn-11) ?H2〇H 〇H2C=C--- TY V/0 / person, /(VII-12) /(VII-13) C2H4OH 0 ry° h2c=c-_»_ vy J^y( Vn-15) U vn-14) As the compound represented by the formula (VIII), the examples l - r L. J 1 are as listed for the compounds represented by the formula (VIII-1) to the formula (VIII-15). Preferred are formula, formula 3), formula (VIII-5), formula (VIII-7), formula (νΙΠ_9), formula (vni_u) to formula Q (VIII-15). More preferred are formula (VIII-1), formula (VIII-7), formula (VIII-9), formula (VIII-15). • 41- 146960.doc 201036941

H2〇=〇H "*〇 **™Q H2C=CH_C*-〇 —ch H2〇=CH-C—〇—C2H4 H2p=CH-C—〇—C2H4—OH2〇=〇H "*〇 **TMQ H2C=CH_C*-〇——ch H2〇=CH-C—〇—C2H4 H2p=CH-C—〇—C2H4—O

H2C=0—*C—〇—CH CH3〇 h2c=c—C—0—c2H4 CH3〇 h2c=c~*c—0—c2H4 選自由式（VII)所示之化合物及式（VIII)所示之化合物所組成群中的至少一種化合物可分別單獨使用。又，亦可以任意之比率混合。於混合之情形時，其混合比率以莫耳比計較好的是式（VII):式（VIII)為5:95〜95:5，更好的是 10:90〜90:1〇’進而更好的是2〇:8〇〜8〇:2〇。所謂具有環氧丙烷基之單體，例如係指具有環氧丙烷基之聚合性化合物。具有環氧丙烷基之單體較好的是具有環氧丙烷基及不飽和鍵之化合物，更好的是具有環氧丙烷基且具有（甲基）丙稀醯氧基之化合物。作為具有環氧丙烷基之單體，具體而言可列舉：弘甲基-3-曱基丙烯醯氧基甲基環氧丙烷、3_曱基_3_丙烯醯氧 146960.doc *42- 201036941 &曱基環氧丙烷、3-乙基-3-甲基丙烯醯氧基甲基環氧丙烷、3-乙基-3-丙烯醯氧基甲基環氧丙烷、3_甲基_3_甲基丙 _氧基乙基環氧丙烷、3-甲基丙烯醯氧基：基㈣丙烷、3-乙基-3-甲基丙烯醯氧基乙基環氧丙烷或者弘乙基-% 丙烯醯氧基乙基環氧丙烷等。所謂具有四氫咬喃基之單體，例如係指具有四氫呋喃基之聚合性化合物。具有四氫呋喃基之單體較好的是具有四 0 氫呋喃基及不飽和鍵之化合物，更好的是具有四氫呋喃基且具有（甲基）丙烯醯氧基之化合物。作為具有四氫°夫喃基之單體，具體而言可列舉：丙烯酸四風糠1旨（例如\^(；〇31;\^#150’大阪有機化學工業（股）製造）、甲基丙烯酸四氫糠酯等。作為可共聚合之單體（B3)，例如可列舉： (甲基）丙烯酸甲酯、（曱基）丙烯酸乙酯、（曱基）丙烯酸正丁酯、（曱基）丙烯酸第二丁酯、（曱基）丙烯酸第三丁酯等 Q (甲基）丙烯酸烷基酯類； (甲基）丙烯酸環己酯、（甲基）丙烯酸2-甲基環己酯、（曱基）丙烯酸三環[5.2.1.02’6]癸-8-基酯（於該技術領域中，慣用名係稱作（甲基）丙烯酸二環戊酯）、（曱基）丙烯酸二環戊氧基乙酯、（甲基）丙烯酸異蓓酯等（甲基）丙烯酸環狀烷基酯類； (甲基）丙烯酸苯酯、（甲基）丙烯酸苄酯等（甲基）丙烯酸芳基酯類；順丁烯二酸二乙酯、反丁烯二酸二乙酯、衣康酸二乙酯 146960.doc -43- 201036941 等二羧酸二酯； (曱基）丙烯酸2-羥基乙酯、（曱基）丙烯酸2_羥基丙酯等羥基烧基醋類；雙環[2.2.1]庚-2-烯、5-甲基雙環[2.2.1]庚·2_烯、5-乙基雙％ [2.2.1]庚-2-稀' 5-經基雙環[2.2.1]庚-2-稀、5-羥曱基 · 雙裱[2.2.1]庚-2-烯、5-(2'-羥乙基）雙環|；2.2.1]庚-2-烯、5- 甲氧基雙環[2.2.1]庚-2-烯、5-乙氧基雙環[2.2.1]庚-2-烯、 5,6-一羥基雙環[2.2.1]庚-2-烯、5,6-二（羥甲基）雙環[2.2_1] 庚-2-烯、5,6-二（2’_羥乙基）雙環[22 ^庚。烯、5,6_二甲 ❹ 氧基雙環[2.2.1]庚-2-烯、5,6-二乙氧基雙環[2 2 ^庚_2_ 烯5_羥基-曱基雙環[2.2.1]庚-2-烯、5-羥基-5 -乙基雙環[2.2.1]庚_2_烯、5_羥曱基_5_甲基雙環[2 2庚_2_烯、5_ =三丁氧錢基雙環[2.2.im_2•烯、5•環己基氧基幾基雙環[2.2.1]庚-2-烯、5_苯氧基幾基雙環[2 21]庚_2_稀、5,6_ (第一丁氧基羰基）雙環[2.2.1]庚_2-烯、5,6-二（環己基氧基羰基）雙環烯等雙環不飽和化合物類； N曱基順丁烯二醯亞胺、N_乙基順丁烯二醯亞胺、N_丙 Q 基順丁烯二醯亞胺等N-烷基順丁烯二醯亞胺； Ν ί衣戊基順丁烯二醯亞胺、N_環己基順丁稀二酿亞胺、 N-環辛基順丁烯二醯亞胺等N_環烧基順丁烯二酿亞胺； - N-金剛院基順丁烯二醯亞胺、n_降福基順丁稀二酿亞胺. 專N父聯碳丨衣式基取代順丁烯二醯亞胺； N-苯基順丁烯二酿亞胺等㈣基順丁烯二酸亞胺； N-节基順丁烯二醯亞胺等沭芳烷基順丁烯二醯亞胺； 146960.doc -44 - 201036941 Ν-丁二醯亞胺基_3.順丁烯二醯亞胺苯甲酸自旨、义丁二醯亞胺基·4·順Τ烯二醯亞胺丁酸§旨、Ν_τ :醯亞胺基: 順丁烯二醯亞胺己酸酯、Ν_ 丁二醯亞胺基_3_順丁烯二醯亞胺丙酸醋、Ν-(9个定基)順丁烯二醯亞胺等二羰基醯亞胺衍生物類；以及 Ο Ο 苯乙烯、α-曱基苯乙烯、帛甲基苯乙烯、董"基苯乙烯、乙烯基曱苯、對甲氧基笨乙烯、丙烯腈、甲基丙烯腈、亂乙稀、偏二氯乙烯、丙稀醯胺、甲基丙稀酿胺、乙酸乙烯酯、1,3-丁二烯、異戊二烯、2,3_二甲基丁二烯等。，一其中，就共聚反應性及鹼溶解性之觀點而言，較好的是苯乙烯、Ν-苯基順丁稀二酸亞胺、Ν_環己基順丁烯二醯亞胺、Ν-苄基順丁烯二醯亞胺、雙環[2 21]庚_2_烯等。共聚物[Κ1]〜[Κ4]例如可參照文獻「高分子合成之實驗法」（大津隆行著，發行所：化學同人（股），第丨版第丨次印刷，1972年3月1日發行）中所記載之方法及該文獻中所記載之引用文獻來製造。具體而言，將構成共聚物之單體（B1)及（B2)、視需要之 (B3)之特定量、聚合起始劑以及溶劑裝入於反應容器中，並藉由氮氣置換氧氣，於不存在氧氣之情況下進行攪拌、加熱 '保溫，藉此獲得聚合物。裝入方法、反應溫度及時間等聚合條件可考慮製造設備、由聚合所產生之發熱量等而適當調整。此處所使用之聚合起始劑及溶劑可使用該領域中通常使 146960.doc •45- 201036941 用的任意之聚合起始劑及溶劑。例如可使用本說明書中所例示之聚合起始劑及溶劑等。曰再者’所獲得之共聚物可直接使収應後之溶液，亦可使用經濃縮或稀釋之溶液，還可使用藉由再沈殿等方法而作為固體（粉體）取出者。尤其是於上述聚合時藉由使用下述之溶劑作為溶劑，可直接使用反應後之料，從而可使製造步驟簡略化。構成共聚物[K1]4單體之比率相對於構成共聚物[K1] 之早體的合計莫耳數較好的是處於以下之範圍内。 (Β1) 5〜95莫耳％，更好的是1〇〜9〇莫耳％ (Β2) 5〜95莫耳％，更好的是10〜90莫耳％。構成八聚物[Κ2]之各單體之比率相對於構成共聚物 [Κ2]之單體的合計莫耳數較好的是處於以下之範圍内。 (Β1) 2〜40莫耳％，更好的是5〜35莫耳％ (Β2) 2〜95莫耳％，更好的是5〜80莫耳％ (Β3) 1〜65莫耳％，更好的是1〜60莫耳％。共聚物[Κ3]可經由兩階段之步驟來製造。 f 方法㈣地使（Bl)與（Β3)共聚合而獲得共聚物。 ;b形f纟單體之比率相對於構成該共聚物之單體的合計莫耳數較好的是處於以下之範圍内。 (B1) 5〜50莫耳％ ’較好的是1〇〜45莫耳％ (B3) 50〜95莫耳％，較好的是55〜％莫耳％。冑原自（Bl)與（B3)之共聚物的（B1)之缓git及/或羧 146960.doc -46 - 201036941 酸野的-部分、與源自（B2)之環狀鱗（環氧乙院基、環氧丙烷基或四氫呋喃基）反應。為此，繼續將燒瓶内環境自氮氣置換成空氣，並將 _、反應觸媒以及聚合抑制劑等裝人燒瓶内，然後於例如60〜贿下繼續反應卜1〇小時。襄入方法、反應溫度及時間等反應條件可考膚製抨μ供+w T把衣& 5又備或由聚合所產生之發熱量等而適當調整。〇此時（B2)之莫耳數相對於_之莫耳數較好的是5〜80莫耳％，更好的是1〇〜75莫耳％，進而更好的是15〜70莫耳 %。反應觸媒例如較好的是用作緩基與環狀醚之反應觸媒者。具體而言，可列舉三（二甲基胺基甲基）苯紛等。反應觸媒之使用量例如相對於（B i)〜(Μ)之合計量較好的是0.001〜5質量％。聚合抑制劑例如可列舉對苯二紛等。〇聚合抑制劑之使用量例如相對於（B1)〜(B3)之合計量較好的是0.001〜5質量％。構成*物[K4]之各單體之比率相對於構成共聚物[κ4] 之單體的合計莫耳數較好的是處於以下之範圍内。 (B1) 2〜40莫耳％，更好的是5~35莫耳％ (B2) 60〜98莫耳％，更好的是65〜95莫耳％。共聚物[K1]〜[K4]之聚苯乙婦換算之重量平均分子量較好的是3,000〜1〇〇,〇〇〇，更好的是5 〇〇〇〜5〇〇〇〇。共聚物[K1]〜[K4]之分散度（分子量分布）、[重量平均分 146960.doc •47· 201036941 子量（Mw)/數平均分子量（Μη)]較好的是hl〜6 〇，更好的是 1.2〜4·0 0 樹脂（D)之聚苯乙烯換算重量平均分子量較好的是 5,000〜35,000，更好的是6,〇〇〇〜3〇,〇〇〇，特別好的= 7，刪〜28，_。若分子量處於上述之範圍心則存在塗= 硬度提昇、殘膜率亦較高、非像素部相對於顯影液之溶解性良好、解像度提昇之傾向。再者，重量平均分子量例如係藉由Gpc法（制Μ刪編H2C=0—*C—〇—CH CH3〇h2c=c—C—0—c2H4 CH3〇h2c=c~*c—0—c2H4 Select the compound represented by formula (VII) and formula (VIII) At least one of the compounds consisting of the compounds may be used alone. Also, it can be mixed at any ratio. In the case of mixing, the mixing ratio is preferably a molar ratio of the formula (VII): the formula (VIII) is 5:95 to 95:5, more preferably 10:90 to 90:1 〇' and further Good is 2〇: 8〇~8〇: 2〇. The monomer having an oxypropylene group means, for example, a polymerizable compound having an oxypropylene group. The monomer having an oxypropylene group is preferably a compound having an epoxy group and an unsaturated bond, more preferably a compound having an oxypropylene group and having a (meth) acryloxy group. Specific examples of the monomer having an oxypropylene group include: m-methyl-3-mercapto propylene methoxymethyl propylene oxide, 3 fluorenyl _3 propylene oxyfluoride 146960.doc *42- 201036941 & mercapto propylene oxide, 3-ethyl-3-methylpropenyloxymethyl propylene oxide, 3-ethyl-3-propenyloxymethyl propylene oxide, 3-methyl _ 3-methylpropoxy-oxyethyl propylene oxide, 3-methylpropenyloxy: yl (tetra)propane, 3-ethyl-3-methylpropenyloxyethyl propylene oxide or hydroxyethyl- % propylene oxiranyl ethyl propylene oxide and the like. The monomer having a tetrahydrofuranyl group means, for example, a polymerizable compound having a tetrahydrofuranyl group. The monomer having a tetrahydrofuranyl group is preferably a compound having a tetrahydrofuranyl group and an unsaturated bond, more preferably a compound having a tetrahydrofuranyl group and having a (meth)acryloxy group. Specific examples of the monomer having a tetrahydrofuranyl group include: acrylic acid tetrapholon 1 (for example, \^(;〇31;\^#150' Osaka Organic Chemical Industry Co., Ltd.), methyl Tetrahydrofurfuryl acrylate, etc. Examples of the copolymerizable monomer (B3) include methyl (meth)acrylate, ethyl (meth)acrylate, and n-butyl (meth)acrylate. a Q (meth)acrylic acid alkyl ester such as a second butyl acrylate or a tert-butyl (meth) acrylate; a cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, (fluorenyl) tricyclo[5.2.1.02'6]non-8-yl ester (in the technical field, the conventional name is called dicyclopentanyl (meth)acrylate), and the (fluorenyl)acrylic acid bicyclic ring (meth)acrylic acid cyclic alkyl esters such as pentyloxyethyl ester and isodecyl (meth)acrylate; (meth)acrylic acid aryl groups such as phenyl (meth)acrylate and benzyl (meth)acrylate Ester; diethyl maleate, diethyl fumarate, diethyl itaconate 146960.doc -43- 201036941 (曱) 2-hydroxyethyl acrylate, 2-hydroxypropyl (meth) acrylate, hydroxyalkyl vinegar; bicyclo [2.2.1] hept-2-ene, 5-methyl bicyclo [2.2.1 Geng·2_ene, 5-ethylbis% [2.2.1]hept-2-diene 5-pyridylbicyclo[2.2.1]hept-2-diene, 5-hydroxyindole·biguanidine [2.2 .1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo]; 2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5 -ethoxybicyclo[2.2.1]hept-2-ene, 5,6-monohydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2_1]g 2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[22^heptene,5,6-dimethylhydrazineoxybicyclo[2.2.1]hept-2-ene, 5,6 -diethoxybicyclo[2 2 ^hept-2-ene 5-hydroxy-indenylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept_2_ Alkene, 5-hydroxyindole-5-methylbicyclo[2 2 hept-2-ene, 5_ = tributoxycarbonylbicyclo[2.2.im_2•ene, 5•cyclohexyloxymethylbicyclo[2.2.1 Hept-2-ene, 5-phenoxycyclobicyclo[2 21]hept-2-di, 5,6-(first butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, 5, Bicyclic unsaturated compounds such as 6-di(cyclohexyloxycarbonyl)bicycloalkenes N-alkyl maleimide, such as N-mercaptobutyleneimine, N-ethylbutyleneimine, N-propyl-butenylimide, and the like; Ν ί N-cycloalkyl succinimide, N-cyclohexyl cis-butyl iodide, N-cyclohexyl succinimide, etc.; - N- King Kong Institute, cis-butenylenediamine, n_norfosine, butadiene di-imine. Special N-parent carbon-based substituted maleimide; N-phenyl-butene a tetraalkyl succinimide such as an imine; an aralkylene maleimide such as N-pyryl succinimide; 146960.doc -44 - 201036941 Ν-丁二醯Imino 3-pyrenediamine benzoic acid, Isobutylene imino-4, cis-decene diimine butyric acid §, Ν_τ: quinone imine: cis-butene Derivatives of dicarbonylimine hexanoic acid esters such as bis-imine hexanoate, hydrazine butyl succinimide glycerol, hydrazine-(9-based) maleimide And Ο 苯乙烯 styrene, α-mercapto styrene, fluorenylmethyl styrene, bromine, styrene, vinyl fluorene, p-methoxy Stupid ethylene, acrylonitrile, methacrylonitrile, vinylidene chloride, vinylidene chloride, acrylamide, methyl propylamine, vinyl acetate, 1,3-butadiene, isoprene, 2 , 3_ dimethyl butadiene, and the like. Among them, from the viewpoints of copolymerization reactivity and alkali solubility, styrene, fluorene-phenyl cis-butyl succinate, Ν-cyclohexyl maleimide, hydrazine- are preferred. Benzyl maleimide, bicyclo[2 21]hept-2-ene, and the like. Copolymers [Κ1]~[Κ4] For example, please refer to the document "Experimental method for polymer synthesis" (Otsu Takayuki, issue: Chemical Tongren (share), Dijon Edition, second print, issued on March 1, 1972 The method described in the above and the cited documents described in the literature are manufactured. Specifically, a monomer (B1) and (B2) constituting the copolymer, a specific amount (B3), a polymerization initiator, and a solvent are charged in a reaction vessel, and oxygen is replaced by nitrogen. The mixture was stirred and heated in the absence of oxygen to obtain a polymer. The polymerization conditions such as the charging method, the reaction temperature, and the like can be appropriately adjusted in consideration of the production equipment, the calorific value generated by the polymerization, and the like. As the polymerization initiator and solvent used herein, any of the polymerization initiators and solvents conventionally used in the field of 146960.doc •45-201036941 can be used. For example, a polymerization initiator, a solvent, and the like exemplified in the present specification can be used. Further, the copolymer obtained by the above can be directly used as a solution after the absorption, or a concentrated or diluted solution, or a solid (powder) extractor by a method such as re-sinking. In particular, in the above polymerization, by using the solvent described below as a solvent, the material after the reaction can be used as it is, so that the production steps can be simplified. The ratio of the ratio of the monomers constituting the copolymer [K1] 4 to the total number of moles of the precursors constituting the copolymer [K1] is preferably in the range of the following. (Β1) 5 to 95% by mole, more preferably 1〇~9〇 Moer% (Β2) 5~95% by mole, and more preferably 10 to 90% by mole. The ratio of the respective monomers constituting the octamer [Κ2] is preferably in the range of the following with respect to the total number of moles of the monomers constituting the copolymer [Κ2]. (Β1) 2~40mol%, more preferably 5~35mol% (Β2) 2~95mol%, more preferably 5~80mol% (Β3) 1~65mol%, More preferably, it is 1 to 60% by mole. The copolymer [Κ3] can be produced via a two-stage process. f Method (4) Copolymerization of (Bl) with (Β3) to obtain a copolymer. The ratio of the b-form monomer to the total of the monomers constituting the copolymer is preferably in the range of the following. (B1) 5 to 50 mol% ‘preferably 1 〇 to 45 mol% (B3) 50 to 95 mol%, preferably 55 to % mol%. ( git and/or carboxy 146960.doc -46 - 201036941 of the copolymer of (Bl) and (B3), the acid-derived part, and the ring-shaped scale derived from (B2) Reaction of a basal, propylene oxide or tetrahydrofuranyl group. To this end, the environment inside the flask was continuously replaced with nitrogen, and the flask, the reaction catalyst, and the polymerization inhibitor were placed in a flask, and then the reaction was continued for 1 hour, for example, under a bribe. The reaction conditions such as the intrusion method, the reaction temperature and the time can be appropriately adjusted by the method of preparing the skin for the wμ supply + w T coat & 5 or by the heat generated by the polymerization. 〇 The number of moles of (B2) at this time is preferably 5 to 80 mol%, more preferably 1 to 75 mol%, and even more preferably 15 to 70 m. %. The reaction catalyst is preferably used, for example, as a reaction catalyst for a slow group and a cyclic ether. Specific examples include tris(dimethylaminomethyl)benzene and the like. The amount of the reaction catalyst used is, for example, preferably 0.001 to 5% by mass based on the total of (B i) to (Μ). Examples of the polymerization inhibitor include p-benzoic acid and the like. The amount of the polymerization inhibitor to be used is, for example, preferably 0.001 to 5% by mass based on the total amount of (B1) to (B3). The ratio of the respective monomers constituting the *[K4] is preferably in the range of the following with respect to the total number of moles of the monomers constituting the copolymer [κ4]. (B1) 2 to 40 mol%, more preferably 5 to 35 mol% (B2) 60 to 98 mol%, and more preferably 65 to 95 mol%. The weight average molecular weight of the polystyrene converted to the copolymer [K1] to [K4] is preferably 3,000 to 1 Torr, 〇〇〇, more preferably 5 〇〇〇 to 5 〇〇〇〇. The dispersion (molecular weight distribution) of the copolymer [K1] to [K4], [weight average of 146960.doc • 47·201036941 sub-quantity (Mw) / number average molecular weight (?η)] is preferably hl~6 〇, More preferably, the polystyrene-equivalent weight average molecular weight of the resin (D) is preferably 5,000 to 35,000, more preferably 6, 〇〇〇~3 〇, 〇〇〇, particularly good. = 7, delete ~ 28, _. When the molecular weight is in the above range, the coating hardness is increased, the residual film ratio is also high, the solubility of the non-pixel portion with respect to the developer is good, and the resolution tends to be improved. Furthermore, the weight average molecular weight is, for example, by the Gpc method.

Chr〇matography，凝膠滲透層析法）所測定之值，1體而言’可列舉藉由實施例中所記載之測定條件所敎之值等。樹脂⑼之酸值較好的是50〜15〇，更好的是6〇〜135,特別好的是7G〜135。此處之酸值的值係測定中和丨g驗溶性樹:_需要之氯氧化卸之量(mg)，通常可藉由使用氮氧化鉀水溶液進行滴定而求得。樹脂⑼之含量相對於著色感光性樹心合物之固形物成純好的是7〜65質量％，更好的是〜㈣量％，特別好 :疋17〜55質量％。若驗溶性樹脂⑻之含量處於該範園 ’則存在可形成圖案，且解像度及殘膜率提昇之傾向。作為光聚合性化合物⑻，可列舉能夠利用藉由對下述 2聚合起始卿）照射光而產生之活性自由基、酸等而 =的化合物’例如具有聚合性之碳-碳不飽和鍵之化合光聚合性化合物⑻較好的是三官能以上之多官能之光 146960.doc •48· 201036941 .K合性化合物。作為三官能以上之多官能之光聚合性化合 Ή如可列舉.季戊四醇四丙稀酸酯、季戊四醇四甲基丙烯日、一季戊四醇五丙稀酸酯、二季戊四醇五曱基丙 _ 婦酸自曰—季戊四醇六丙稀酸酉旨、二季戊四醇六甲基丙浠 I S曰等。該等可單獨使用，亦可組合兩種以上來使用。光聚合性化合物（E)之含量相對於著色組合物之固形物成分較好的是7〜65質量％，更好的是13〜6〇質量％，進而更〇好的疋17〜55質量％。若光聚合性化合物（E)之含量處於該範圍内則製造彩色濾光片時，存在硬化得以充分地進仃、顯影W後之膜厚比率提昇、難以將圖案底切而密著性良好之傾向。作為光聚合起始劑（F)，可列舉活性自由基產生劑、酸產生劑等。活性自由基產生劑係藉由照射光（g線、i線、h 線等紫外線等）而產生活性自由基。又，酸產生劑係藉由照射光而產生酸。〇作為上述活性自由基產生劑，例如可列舉：苯乙酮系化合物、安息香系化合物、二苯曱酮系化合物、9_氧硫咄嗟系化合物、三畊系化合物、肟系化合物等。作為苯乙酮系化合物，例如可列舉：二乙氧基苯乙酮、甲基2-味琳基_1_(4_甲基硫燒基苯基）丙烧酮、二甲基胺基-1-(4-味啉基苯基）_2-苄基丁烷_丨_酮、2_羥基_2_甲基-1-笨基丙烷-1-酮、苯偶醯二曱縮酮、2_羥基_2_曱基 [4-(2-羥基乙氧基）苯基]丙烷酮、丨_羥基環己基苯基酮、2-羥基_2_甲基基乙烯基）苯基]丙烷_丨_酮之 146960.doc -49· 201036941 低聚物等’較好的是可列舉烷基苯基）丙烷嗣等。土味啉基-1-(4-甲基硫作為安息香系化合物，例如可列…自醚、安息香***、安自夭s 牛文心香、安息曰曱文息香異丙醚、作為二苯甲酮系化合物，例心香異丁鍵等。甲醯基苯曱酸曱酯、4 〜列舉：二苯甲酮、鄰苯二笨护_ 土一本甲_、4-苯曱醯基_4丨-曱基本爪帖、3,3，4,4，-四（；第三 €) 认6-三甲基二笨甲_等。基過氧化《)二苯甲鋼、作為9-氧硫咄P星系化合 #、例如可列舉：2-異丙基-9-氧 &、4-異丙基·9_氧硫，山哇、2 -% c ^ ^ ，-—乙基-9-氧硫咄ρ星、2,4- -亂，氧基9_氧硫·星等。作為二畊系化合物，例如 (4-甲氧基苯基Η，〗，%三，：.’心雙(三氣曱基)_6_ «... —升2,4-雙（三氯甲基）_6_(4_甲氧基奈基）-1，3,5-三畊、2 4-雔隹 ’又（―氣甲基）-6-(4-甲氧基苯乙烯土，3,5 一井、2,4_雙（三氯曱基）-6-[2-(5-曱基吱喃-2-基） Ο 乙烯基]-1，3,5-三_、2,4_雙（三氯甲基）6_[2十夫喃-2_基）乙烯基]-1，3,5-三_、2,4-雙（三氯甲基）_6_[2_(4-二乙基胺基_ 2_甲基苯基）乙烯基Η，W井、2,4-雙（三氯甲基）冬[2_ (3,4-二甲氧基苯基）乙烯基μι，3,5-三畊等。料肟系化合物，例如可列舉〇_醯基肟系化合物。具體而。，可列舉.Ν-苯甲酿氧基]_(4_苯基硫烧基苯基）丁院_ 1 亞胺、N_苯甲酿氧基^-(4•苯基硫烧基苯基）辛烷小酮2_亞胺、N-乙醯氧基乙基_6_(2_曱基苯甲醯基）_ 9H卡唑-3-基]乙烷-1-亞胺、N_乙酸氧基叩-乙基_6_{2_ 146960.doc •50、 201036941 甲基_4-(3,3-一甲基-2,4-二氧雜環戍基甲氧基）苯甲酿基） 9H-咔唑-3_基]乙烷_丨_亞胺等。一進而，作為活性自由基產生劑，例如亦可使用：2,4,6 .:甲基苯甲醯基二苯基氧化膦、2,2'-雙（鄰氯苯基）. M’，5,5，-四苯基-1，2，·聯咪唾、10-丁基-2_氯。丫㈣、2_乙土二醌苯偶醯、9,1 〇-菲酉昆、棒腦西昆、笨基乙駿酸甲醋、一戊鈦化合物等。〇 “料❹生劑，例如可料：4•减苯m錄對甲苯滅Μ 4-輕基苯基二甲基鎮六就録酸鹽、乙酿氧基苯基—甲基錄對甲苯確酸鹽、4_乙酿氧基苯基-甲基-节基銃六氟録酸鹽、三苯基鎮對甲苯石黃酸鹽、三苯基疏六氣^ 酸鹽、二苯基錤對甲苯石黃酸鹽、二苯基鎭六說錄酸鹽等鑽鹽類’硝基苄基甲苯磺酸酯類’安息香甲苯磺酸酯類等。作為活性自由基產生劑而列舉如上之化合物中亦存在產生活性自由基之同時產生酸之化合物，例如三畊系光聚〇合起始劑亦可用作酸產生劑。光聚合起始劑（F)之含量相對於樹脂（D)及光聚合性化合物（E)之合計量較好的是〇卜3〇質量％，更好的是卜汕質量 %。若光聚合起始劑之含量處於該範圍内，則可提高感光度’使得曝光時間縮短從而提昇生產性。本發明之著色組合物亦可進一步含有光聚合起始助劑。光聚合起始助劑係通常與光聚合起始劑（F)組合使用，以促進藉由光聚合起始劑而產生聚合之光聚合性化合物之聚合、或者藉由提高感光度而提昇光聚合起始劑之分解效 146960.doc •51· 201036941 率的化合物。作為光聚合起始助劑，儿人… j 了列舉胺系化合物、烷氧基蒽系化&物、9-氧硫,山嗟系化合物等。作為胺系化合物，你丨心π，一可列舉：三乙醇胺、曱基二乙醇胺、三異丙醇胺、4二一 f暴胺基笨甲酸曱酯、4-二曱基胺基本曱酸乙醋、4- ~~ ψ ^ u —基笨甲酸異戊酯、苯曱酸2_二曱基胺基乙酯、4-二甲基脸其 τ丞胺基笨甲酸2-乙基己酯、N，N-二曱基對曱苯胺、4,4丨-簪田w 笑^一曱基胺基）二苯曱酮（俗稱為米其勒酮）、4,4’-雙（-7 冀 (―乙基月女基）二苯曱酮、4,4，-雙（乙基曱基胺基）二苯甲_等。发中一甲車父好的是4,4，-雙（二乙基胺基）二苯曱酮。作為烷氧基蒽系化合物， σ物例如可列舉9，ι〇-二曱氧基蒽、 2_乙基-9,10 -二甲氧其窗 0 土 - ' 9，1〇_二乙氧基蒽、2_乙基_9,1〇· 一乙氧基复、、9,10 -二丁急其贫丁乳基惠、2-乙基-9,10-二丁氧基蒽等。作為9'氧硫命星系化合物’例如可列舉：2-異丙基冬氧硫♦星、4_異丙基_9_氧硫·星、2,4_二乙基冬氧杨星、 2,4-—氯冬氧硫·星、卜氯冰丙氧基_9_氧心μ。光聚合起始助劑可單獨你用倒便用亦可組合兩種以上來使用。作為光聚合起始助劑，例如亦可使用商品名「隱F」 (保土穀化學工業（股）製造）等市售者。光聚合起始助劑較好的是相對於莫耳之光聚合起始劑⑺以〜莫耳使用’更好的是則別，莫耳制，特別好 146960.doc •52- 201036941 的是以0.01〜5莫耳使用。 (第8步驟）代替第5步驟之使包含磺醯胺化合物之染料溶液（A)通過第1過濾崙的步驟，而使該染料溶液（A)首先通過第3過濾器。 j 第3過濾器係使用由與上述第2過濾器相同之材料等所形成者，且可以相同之方式使該染料溶液（A)通過該第3過濾 ❽ 器。第3過濾器之孔徑較好的是0.1〜2.5 μηι，更好的是〇. 1〜1·〇 μιη ’進而更好的是0.^0.5 μιη。 (第9步驟）將通過第3過濾器後之染料溶液（Α)與選自由顏料或顏料分散液（Β)、溶劑（C)、樹脂（D)、光聚合性化合物（Ε)以及光聚合起始劑（F)所組成群中之至少一種混合。該等各成分可列舉與上述相同者，並可以相同之方式混合〇 Q (第1〇步驟）使通過第3過濾器後之染料溶液（Α)與各成分之混合物通過第4過濾器。第4過濾器係使用與上述第1過濾器相同者（即，孔徑為〇.5〜5.0 μπι之過濾器等）’並能夠以相同之方式使該混合物通過。再者’第3過濾器之孔徑與第4過濾器之孔徑之比較合適的是0.02:1〜5:1 ，較好的是0.04:1〜2:1，更好的是 0.07:1〜1:1 〇 146960.doc -53- 201036941 作為使上述混合物通過第4過濾器之過濾方法，可列舉與通：第1過濾器之方法相同之方法。其中，就抑制通過過濾器後之染料溶液（A)中混入水分等之觀點而言，較好的是於惰性氣體環境下，藉由加壓過濾而使上述混合物通過過慮器。該加壓過濾時之壓力較好的是〇〇1〜1〇 Mb。實施例以下’藉由實施例更詳細地說明本發明。例中之「％」及「份」若無特別說明，則為重量％及質量份。實施例1 :染料A1之合成 (第1步驟）於具備冷卻管及攪拌裝置之容器中混合氯仿410份及二甲基曱醯胺28份。於1〇。(：下歷時20分鐘向混合溶液中滴加亞硫醯氯3 7份。滴加結束後’於保溫下反應3 0分鐘。歷時 15分鐘向反應混合物中添加Acid Red 289(中外化成（股）製造）57份，並於35。(：下反應3小時。進而向反應混合物中添加亞硫醯氣4份並於35°C下反應1.5小時。冷卻反應混合物’於1(TC下滴加2-乙基己胺34份，繼而滴加三乙胺89 份。滴加後，於室溫下反應15小時。濃縮反應混合物，並加入曱醇200份後，再次濃縮直至液量變成約一半為止。進而添加曱醇290份及乙酸20份並反應30分鐘。將反應物注入至離子交換水306份中而使其結晶化，然後過濾並取出。 (第2步，驟）利用50%甲醇水溶液300份、70。(：之去離子水1000份、 146960.doc • 54- 201036941 20°C之去離子水3 〇〇份依序清洗所取出之反應物。 (第3步驟）於60°C下將所獲得之清洗物減壓乾燥1日，獲得5 1份作為紫紅色之固體之染料A1。實施例2 :染料A2之合成 (第1步驟）於具備冷卻管及攪拌裝置之容器中混合氯仿410份及二 0 甲基甲醯胺28份。於1〇。〇下歷時20分鐘向混合溶液中滴加亞硫醯氣37份。滴加結束後，於保溫下反應3〇分鐘。歷時 15分鐘向反應混合物中添加Acid Red 289(中外化成（股）製造）57份，並於35。(：下反應3小時。進而向反應混合物中添加亞硫醯氯4份並於3 5 °C下反應1小時。冷卻反應混合物，於1 〇 C下滴加2-乙基己胺34份’繼而滴加三乙胺89份。滴加後’於室溫下反應1 5小時。濃縮反應混合物，並加入甲醇200份後，再次濃縮直至液量變成約一半為止。進而添〇加甲醇260份及乙酸25份並反應30分鐘。將反應物注入至離子交換水396份中而使其結晶化，然後過濾並取出。 (第2步驟）利用50%甲醇水溶液300份、7(rc之去離子水1〇〇〇份、 20 C之去離子水300份依序清洗所取出之反應物。 (第3步驟）於6〇t下將所獲得之清洗物減壓乾燥丨日，獲得65份作為紫紅色之固體之染料A2。實施例3 :染料A3之合成 146960.doc -55- 201036941 (第1步驟）於具備冷卻管及攪拌裝置之容器中混合乙腈220份及二曱基甲醯胺28份。於1〇。〇下歷時2〇分鐘向混合溶液中滴加亞硫醯氣35份。滴加結束後，於保溫下反應3〇分鐘。歷時 15分鐘向反應混合物中添加Acid Red 289(中外化成（股）製造）57份，並於35°C下反應3小時。冷卻反應混合物，於 1 〇°C下滴加2-乙基己胺34份，繼而滴加三乙胺69份。滴加後’於至溫下反應1 5小時。濃縮反應混合物，並加入甲醇 200份後’再次濃縮直至液量變成約一半為止。進而添加甲醇290份及乙酸16份並反應3〇分鐘。將反應物注入至離子交換水306份中而使其結晶化，然後過濾並取出。 (第2步驟）利用50〇/〇甲醇水溶液3〇〇份、5%鹽酸水溶液8〇〇份、去離子水3 0 0份依序清洗所取出之反應物。 (第3步驟）於60°C下將所獲得之清洗物減壓乾燥1日，獲得44份作為紫紅色之固體之染料A3。實施例4 ·_染料A4之合成 (第1步驟）於具備冷卻管及攪拌裝置之容器中混合氯仿41〇份及二曱基甲S&胺28份。於1 〇°c下歷時20分鐘向混合溶液中滴加亞硫醯氣37份。滴加結束後，於保溫下反應30分鐘。歷時 15分鐘向反應混合物中添加Acid Red 289(中外化成（股）製造）57份，並於35t下反應3小時。其後，進而追加亞硫醯 146960.doc -56- 201036941 氣4份並於35°C下繼續反應！小時。其後，冷卻反應混合物，於10C下滴加2-乙基己胺34份，繼而滴加三乙胺89 份。滴加後，於室溫下反應15小時。濃縮反應混合物，並加入甲醇200份後，再次濃縮直至液量變成約一半為止。進而添加甲醇260份及乙酸25份並反應3〇分鐘。將反應物注入至離子交換水415份中而使其結晶化，然後過濾並取出。 (第2步驟） ❹ 利用50%甲醇水溶液3〇〇份、5%鹽酸水溶液8〇〇份、去離子水300份依序清洗所取出之反應物。 (第3步驟）於60 C下將所獲得之清洗物減壓乾燥1日，獲得42份作為紫紅色之固體之染料A4。實施例5 :染料A5之合成 (第1步驟）〇於具備冷卻管及攪拌裝置之容器中混合乙腈220份及 N，N-二曱基曱醯胺28份。於i〇t下歷時20分鐘向混合溶液中滴加亞硫醯氣3 5份。滴加結束後，於保溫下反應3 〇分鐘。歷時15分鐘向反應混合物中添加Acid Red 289(中外化成（股）製造）5 7份，並於3 5 °C下反應3小時。冷卻反應混合物’於10 C下滴加2 -乙基己胺3 4份’繼而滴加三乙胺8 9 份。滴加後，於室溫下反應15小時。濃縮反應混合物，並加入甲醇200份後，再次濃縮直至液量變成約一半為止。進而添加曱醇306份及乙酸80份並反應30分鐘。將反應物 146960.doc -57- 201036941 注入至離子交換水400份中而使其結晶化，然後過濾並取出。 (第2步驟）利用50%曱醇水溶液300份、5%乙酸水溶液800份、去離子水500份依序清洗所取出之反應物。 (第3步驟）於60°C下將所獲得之清洗物減壓乾燥1日，獲得44份作為紫紅色之固體之染料A5。藉由 LC-MS(liquid chromatography-mass spectrometry，液相層析-質譜法）進行染料A1~A5之化學鑑定，結果可知染料A1〜A5均為包含下述化合物（1)〜（5)之組合物。The value measured by Chr〇matography, gel permeation chromatography, and the like can be exemplified by the measurement conditions described in the examples. The acid value of the resin (9) is preferably from 50 to 15 Torr, more preferably from 6 to 135, particularly preferably from 7 to 135. Here, the value of the acid value is determined by neutralizing the 丨g test solubility tree: _ the required amount of chlorination (mg), which can usually be determined by titration with an aqueous solution of potassium hydride. The content of the resin (9) is preferably 7 to 65 mass%, more preferably 〜4% by weight, particularly preferably 疋17 to 55 mass%, based on the solid content of the colored photosensitive dendrimer. If the content of the test-soluble resin (8) is in this range, there is a tendency to form a pattern, and the resolution and the residual film ratio tend to increase. Examples of the photopolymerizable compound (8) include a compound which can be activated by irradiation of light with the following two polymerization initiators, and the like, for example, a polymerizable carbon-carbon unsaturated bond. The compound photopolymerizable compound (8) is preferably a trifunctional or higher polyfunctional light 146960.doc • 48· 201036941 .K compound. Examples of the trifunctional or higher polyfunctional photopolymerizable compound include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate day, pentaerythritol pentapropionate, and dipentaerythritol pentadecyl propyl group. - pentaerythritol hexaacrylate acid, dipentaerythritol hexamethyl propyl hydrazine IS hydrazine, and the like. These may be used alone or in combination of two or more. The content of the photopolymerizable compound (E) is preferably from 7 to 65% by mass, more preferably from 13 to 6 % by mass, and still more preferably from 17 to 55% by mass based on the solid content of the coloring composition. . When the content of the photopolymerizable compound (E) is within this range, when the color filter is produced, the film thickness ratio after the curing is sufficiently increased and the development of W is improved, and it is difficult to undercut the pattern and the adhesion is good. tendency. The photopolymerization initiator (F) may, for example, be a living radical generator or an acid generator. The living radical generating agent generates active radicals by irradiating light (such as ultraviolet rays such as g-line, i-line or h-line). Further, the acid generator generates an acid by irradiating light. 〇 Examples of the above-mentioned living radical generating agent include an acetophenone-based compound, a benzoin-based compound, a benzophenone-based compound, a 9-oxosulfonium-based compound, a tri-grain-based compound, and an anthraquinone-based compound. Examples of the acetophenone-based compound include diethoxyacetophenone, methyl 2-isoline-1-(4-methylsulfanylphenyl)propanone, and dimethylamino-1. -(4-morpholinylphenyl)_2-benzylbutane-indole-ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzoin-2, ketal, 2_ Hydroxy_2_mercapto[4-(2-hydroxyethoxy)phenyl]propanone, hydrazine-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methylvinyl)phenyl]propane 丨_ketone 146960.doc -49· 201036941 The oligomer or the like is preferably an alkylphenyl)propane oxime or the like. As a benzoin-based compound, it can be listed as a benzoin-based compound, for example, from ether, benzoin ethyl ether, amphibious snail, scent of scent, benzoin, benzophenone, as benzophenone a compound, such as a heart-like butyl bond, etc. decyl benzoyl phthalate, 4 ~ enumeration: benzophenone, ortho-phenyl benzoate _ soil a _, 4-phenyl fluorenyl _4 丨- 曱 basic claws, 3, 3, 4, 4, - four (; third €) recognize 6-trimethyl bismuth _, etc. based on oxidation of ") benzoic steel, as 9-oxopurine P galaxy compound #, for example, 2-isopropyl-9-oxy&, 4-isopropyl-9-oxysulfide, sulphate, 2 -% c ^ ^, -ethyl-9-oxygen Thiopurine, 2,4-disorder, oxy 9-oxo-sulfur, etc. As a two-tillage compound, for example, (4-methoxyphenyl hydrazine, 〗〖% three,: ''heart double (three gas sulfhydryl) _6_ «... - liter 2,4-bis(trichloromethyl) )_6_(4_methoxynyl)-1,3,5-three tillage, 2 4-雔隹' ((gas methyl)-6-(4-methoxystyrene soil, 3,5 One well, 2,4_bis(trichloroindenyl)-6-[2-(5-fluorenyl-2-yl) fluorene vinyl]-1,3,5-tri-, 2,4_ Bis(trichloromethyl)6_[2-deca-am-2-yl)vinyl]-1,3,5-tri-, 2,4-bis(trichloromethyl)_6_[2_(4-di-B Amino group 2 - methylphenyl) vinyl fluorene, W well, 2,4-bis(trichloromethyl) winter [2_(3,4-dimethoxyphenyl)vinyl ι, 3, 5-three-tillage, etc. The oxime-based compound may, for example, be a ruthenium-based ruthenium-based compound. Specific examples thereof include ruthenium-benzoyloxy]-(4-phenylthioalkyl) butyl院_1 Imine, N_Benzeneoxyl^-(4•phenylsulfanylphenyl)octane ketone 2_imine, N-acetoxyethyl _6_(2_fluorenyl Benzyl hydrazino)_ 9H-carzol-3-yl]ethane-1-imine, N-acetoxy oxime-ethyl _6_{2_ 146960.doc •50, 201036941 methyl _4-(3, 3-monomethyl-2,4- Oxetanyl Shu-ylmethoxy) benzyl stuffed yl) 9H-carbazol--3_ yl] ethane _ _ Shu imine. Further, as the living radical generating agent, for example, 2,4,6 .: methylbenzimidyldiphenylphosphine oxide, 2,2'-bis(o-chlorophenyl). M', 5,5,-Tetraphenyl-1,2,·Limi, 10-butyl-2_chloro.丫(4), 2_B, bismuth benzophenone, 9,1 〇-phenanthrenequinone, rod brain Xikun, stupid base methyl vinegar, monopenta titanium compound. 〇 “Materials, for example, can be: 4 • benzene-reduced benzene, p-toluene, 4-light phenyl dimethyl dimethyl hexahydrate, acid phenyl phenyl-methyl-p-toluene Acid salt, 4_ethyloxyphenyl-methyl-peptidyl hexafluoroantimonate, triphenyl-p-toluene salt, triphenyl sulfonate, diphenyl hydrazine a toluene salt, a diphenyl sulfonium salt, a salt, a nitrobenzyl tosylate, a benzoin tosylate, etc. As a living radical generator, the above compounds are listed. There is also a compound which generates an acid while generating an active radical. For example, a tri-grain photopolymerization initiator can also be used as an acid generator. The content of the photopolymerization initiator (F) is relative to the resin (D) and light. The total amount of the polymerizable compound (E) is preferably 3% by mass, more preferably 汕 by mass%. If the content of the photopolymerization initiator is within this range, the sensitivity can be increased to make the exposure The time is shortened to improve productivity. The coloring composition of the present invention may further contain a photopolymerization initiation aid. It is often used in combination with a photopolymerization initiator (F) to promote polymerization of a photopolymerizable compound which is polymerized by a photopolymerization initiator, or to enhance the decomposition efficiency of a photopolymerization initiator by increasing sensitivity 146960 .doc • 51· 201036941 rate of compound. As a photopolymerization initiation aid, children... J lists amine compounds, alkoxy oxime systems & substances, 9-oxosulfur, hawthorn compounds, etc. Amine compounds, you 丨 π, one can be cited: triethanolamine, decyl diethanolamine, triisopropanolamine, 4 一暴胺胺胺胺、、、、、、、 4- 4- 4- 4- 4- 4- , 4- ~~ ψ ^ u - isoamyl formate, 2-didecylaminoethyl benzoate, 2-ethylhexyl benzoic acid 2-ethylhexyl, N , N-dimercapto-p-aniline, 4,4丨-簪田 w 笑^曱-ylamino)diphenyl fluorenone (commonly known as muscarinone), 4,4'-bis(-7 冀( ―Ethyl sulfanyl) diphenyl fluorenone, 4,4,-bis(ethyl decylamino) benzophenone _, etc. The hair of a car is good, 4,4,-double (two Alkyl) diphenyl fluorenone The ruthenium-based compound, for example, -9, ι〇-dimethoxy oxime, 2-ethyl-9,10-dimethoxy, 0-[9,1〇-diethoxy oxime, 2_Ethyl_9,1〇·1-ethoxy complex, 9,10-dibutan, its depleted butyl ketone, 2-ethyl-9,10-dibutoxy fluorene, etc. as 9' Examples of the oxasulfide compound can be exemplified by 2-isopropoxysulfuroxone, 4-isopropylidene-9-oxosulfanyl, 2,4-diethyloxetine, 2,4- —chlorooxosulfide·star, chloropreneoxy _9_oxygen μ. The photopolymerization start-up additive can be used alone or in combination of two or more. For example, a commercial item such as the product name "Hidden F" (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used. The photopolymerization start-up aid is preferably used in comparison with the photopolymerization initiator (7) of Moer. The better is the case, the Moer system, especially the 146960.doc • 52-201036941 0.01 to 5 moles to use. (8th step) Instead of the step 5, the dye solution (A) containing the sulfonamide compound is passed through the first filter, and the dye solution (A) is first passed through the third filter. j The third filter is formed of the same material as that of the second filter described above, and the dye solution (A) can be passed through the third filter in the same manner. The pore diameter of the third filter is preferably 0.1 to 2.5 μηι, more preferably 〇. 1 to 1·〇 μιη ‘ and further preferably 0.^0.5 μιη. (9th step) The dye solution (Α) after passing through the third filter is selected from a pigment or pigment dispersion (Β), a solvent (C), a resin (D), a photopolymerizable compound (Ε), and photopolymerization. At least one of the groups consisting of the initiator (F) is mixed. The components may be the same as described above, and 〇Q may be mixed in the same manner (Step 1) The mixture of the dye solution (Α) passing through the third filter and each component is passed through the fourth filter. The fourth filter is the same as the above-described first filter (i.e., a filter having a pore diameter of 〇.5 to 5.0 μm), and the mixture can be passed in the same manner. Further, the comparison between the aperture of the third filter and the aperture of the fourth filter is suitably 0.02:1 to 5:1, preferably 0.04:1 to 2:1, more preferably 0.07:1 to 1 :1 〇146960.doc -53- 201036941 As a filtration method for passing the above-mentioned mixture through the fourth filter, the same method as that of the first filter can be mentioned. Among them, from the viewpoint of suppressing the incorporation of moisture or the like into the dye solution (A) after passing through the filter, it is preferred to pass the mixture through a filter under pressure in an inert gas atmosphere by pressure filtration. The pressure at the time of pressure filtration is preferably 〇1~1〇 Mb. EXAMPLES Hereinafter, the present invention will be described in more detail by way of examples. In the examples, "%" and "parts" are % by weight and parts by mass unless otherwise specified. Example 1: Synthesis of Dye A1 (Step 1) 410 parts of chloroform and 28 parts of dimethyl decylamine were mixed in a vessel equipped with a cooling tube and a stirring device. At 1〇. (: 7 parts of sulfite chloride was added dropwise to the mixed solution for 20 minutes. After the completion of the dropwise addition, the reaction was carried out for 30 minutes under heat retention. Acid Red 289 was added to the reaction mixture over 15 minutes (Chinese-Chinese chemical conversion) Manufactured) 57 parts, and at 35. (: 3 hours of reaction. Further, 4 parts of sulfite gas was added to the reaction mixture and reacted at 35 ° C for 1.5 hours. The reaction mixture was cooled at 1 (2 drops under TC) -ethylhexylamine 34 parts, followed by dropwise addition of 89 parts of triethylamine. After the dropwise addition, the reaction was carried out for 15 hours at room temperature. The reaction mixture was concentrated, and after adding 200 parts of decyl alcohol, it was concentrated again until the amount of liquid became about half. Further, 290 parts of decyl alcohol and 20 parts of acetic acid were added and reacted for 30 minutes. The reactant was poured into 306 parts of ion-exchanged water to be crystallized, and then filtered and taken out. (Step 2, step) Using a 50% aqueous methanol solution 300 parts, 70. (: 1000 parts of deionized water, 146960.doc • 54- 201036941 20 °C deionized water 3 依 parts of the removed reactants. (Step 3) at 60 ° C The obtained washing material was dried under reduced pressure for 1 day to obtain 51 parts as a purple-red solid. Dye A1. Example 2: Synthesis of Dye A2 (Step 1) In a vessel equipped with a cooling tube and a stirring device, 410 parts of chloroform and 28 parts of dimethylformamide were mixed at 1 Torr. 37 parts of sulfite gas was added dropwise to the mixed solution at the end of the mixture. After the completion of the dropwise addition, the reaction was carried out for 3 minutes under heat retention, and 57 parts of Acid Red 289 (manufactured by Sino-foreign Chemicals Co., Ltd.) was added to the reaction mixture over 15 minutes. At 35. (: the next reaction for 3 hours. Further, 4 parts of sulfinium chloride was added to the reaction mixture and reacted at 35 ° C for 1 hour. The reaction mixture was cooled, and 2-ethylhexylamine was added dropwise at 1 ° C. 34 parts 'then 89 parts of triethylamine was added dropwise. After the dropwise addition, the reaction was carried out for 15 hours at room temperature. The reaction mixture was concentrated, and after adding 200 parts of methanol, it was concentrated again until the amount of liquid became about half. 260 parts of methanol and 25 parts of acetic acid were reacted for 30 minutes. The reactant was injected into 396 parts of ion-exchanged water to be crystallized, and then filtered and taken out. (Step 2) 300 parts of a 50% methanol aqueous solution, 7 (rc) 1 part of deionized water, 300 parts of 20 C of deionized water The removed reaction product was washed. (Step 3) The obtained washing material was dried under reduced pressure at 6 Torr for 65 days to obtain 65 parts of a dye A2 as a purple-red solid. Example 3: Synthesis of Dye A3 146960 .doc -55- 201036941 (Step 1) Mix 220 parts of acetonitrile and 28 parts of dimethyl carbamide in a container equipped with a cooling tube and a stirring device at 1 Torr. The mixture is dropped into the mixed solution for 2 minutes. 35 parts of sulphur gas. After the completion of the dropwise addition, the reaction was carried out for 3 minutes under heat. 57 parts of Acid Red 289 (manufactured by Sino-foreign Chemicals Co., Ltd.) was added to the reaction mixture over 15 minutes, and reacted at 35 ° C for 3 hours. The reaction mixture was cooled, and 34 parts of 2-ethylhexylamine was added dropwise at 1 ° C, followed by dropwise addition of 69 parts of triethylamine. After the dropwise addition, the reaction was allowed to proceed for 15 hours at a temperature. The reaction mixture was concentrated, and after adding 200 parts of methanol, it was again concentrated until the amount of liquid became about half. Further, 290 parts of methanol and 16 parts of acetic acid were added and reacted for 3 minutes. The reactant was poured into 306 parts of ion exchange water to be crystallized, and then filtered and taken out. (2nd step) The taken-out reaction product was washed sequentially with 3 parts of a 50 〇/〇 methanol aqueous solution, 8 parts of a 5% hydrochloric acid aqueous solution, and 300 parts of deionized water. (3rd step) The obtained washing material was dried under reduced pressure at 60 ° C for 1 day to obtain 44 parts of a dye A3 as a purple-red solid. Example 4 - Synthesis of Dye A4 (Step 1) In a vessel equipped with a cooling tube and a stirring device, 41 parts of chloroform and 28 parts of dimercapto S & amine were mixed. 37 parts of sulphur sulphur gas was added dropwise to the mixed solution at 20 ° C for 20 minutes. After the completion of the dropwise addition, the reaction was carried out for 30 minutes under heat retention. 57 parts of Acid Red 289 (manufactured by Sino-foreign Chemicals Co., Ltd.) was added to the reaction mixture over 15 minutes, and reacted at 35 tons for 3 hours. Thereafter, 4 parts of sulphur 146960.doc -56-201036941 gas was further added and the reaction was continued at 35 °C! hour. Thereafter, the reaction mixture was cooled, and 34 parts of 2-ethylhexylamine was added dropwise thereto at 10 C, followed by dropwise addition of 89 parts of triethylamine. After the dropwise addition, the reaction was carried out at room temperature for 15 hours. The reaction mixture was concentrated, and after adding 200 parts of methanol, it was concentrated again until the liquid amount became about half. Further, 260 parts of methanol and 25 parts of acetic acid were added and reacted for 3 minutes. The reactant was poured into 415 parts of ion-exchanged water to be crystallized, and then filtered and taken out. (Second step) 所 The taken-out reaction product was washed sequentially with 3 parts of a 50% aqueous methanol solution, 8 parts of a 5% aqueous hydrochloric acid solution, and 300 parts of deionized water. (3rd step) The obtained washing material was dried under reduced pressure at 60 C for 1 day to obtain 42 parts of a dye A4 as a purplish solid. Example 5: Synthesis of Dye A5 (Step 1) 220 220 parts of acetonitrile and 28 parts of N,N-didecylguanamine were mixed in a vessel equipped with a cooling tube and a stirring device. To the mixed solution, 35 parts of arsenite gas was added dropwise over 10 minutes at i〇t. After the completion of the dropwise addition, the reaction was carried out for 3 〇 minutes under heat retention. Five 7 parts of Acid Red 289 (manufactured by Chinese or Foreign Chemical Co., Ltd.) was added to the reaction mixture over 15 minutes, and reacted at 35 ° C for 3 hours. The reaction mixture was cooled, and 3 parts of 2-ethylhexylamine was added dropwise at 10 C, followed by dropwise addition of 8 9 portions of triethylamine. After the dropwise addition, the reaction was carried out at room temperature for 15 hours. The reaction mixture was concentrated, and after adding 200 parts of methanol, it was concentrated again until the liquid amount became about half. Further, 306 parts of decyl alcohol and 80 parts of acetic acid were added and reacted for 30 minutes. The reactant 146960.doc -57 - 201036941 was injected into 400 parts of ion-exchanged water to be crystallized, and then filtered and taken out. (Second step) The taken-out reaction product was washed sequentially with 300 parts of a 50% aqueous methanol solution, 800 parts of a 5% aqueous acetic acid solution, and 500 parts of deionized water. (3rd step) The obtained washing material was dried under reduced pressure at 60 ° C for 1 day to obtain 44 parts of a dye A5 as a purplish solid. The chemical identification of the dyes A1 to A5 was carried out by LC-MS (liquid chromatography-mass spectrometry), and it was found that the dyes A1 to A5 all contained the combination of the following compounds (1) to (5). Things.

LC 裝置：Agilent 1100 管柱：Wakosil-II 3C18HG 3 ux3.0 mmxl50 mm 流動相A:水/乙腈=9/l(10mMNH4OH) 流動相8:水/乙腈=1/9(1〇111]^]^114011) 流動相 B% : 10%-(3 5 min)-100%(3 0 min)LC unit: Agilent 1100 Column: Wakosil-II 3C18HG 3 ux 3.0 mmxl50 mm Mobile phase A: water/acetonitrile = 9/l (10 mM NH4OH) Mobile phase 8: water/acetonitrile = 1/9 (1〇111]^] ^114011) Mobile phase B%: 10%-(3 5 min)-100% (30 min)

流速：0.5 mL/min UV檢測：254 nm MASS 裝置：HP LC/MSD 離子化：ESI +Flow rate: 0.5 mL/min UV detection: 254 nm MASS Device: HP LC/MSD Ionization: ESI +

掃描範圍：1〇〇~1500 碎裂電壓（Fragmentor) : 120 V 146960.doc -58- 201036941Scanning range: 1〇〇~1500 Fragmentor: 120 V 146960.doc -58- 201036941

乾燥氣體：350°C 化合物（1) 實測值（[M+H] + ) : 655_2 計算值（Exact Mass): 654.2Dry gas: 350 ° C Compound (1) Found ([M+H] + ) : 655_2 Calculated (Exact Mass): 654.2

化合物（2) 實測值（[Μ + Η]+ ): 682.2 計算值（Exact Mass) : 68 1.2Compound (2) Found ([Μ + Η]+ ): 682.2 Calculated (Exact Mass) : 68 1.2

化合物（3) 實測值（[M+H] + ): 766.3 計算值（Exact Mass): 765.3Compound (3) Found ([M+H] + ): 766.3 Calculated (Exact Mass): 765.3

化合物（4) 實測值（[M+H]+) : 957.4 計算值（Exact Mass) : 956.4Compound (4) Found ([M+H]+): 957.4 Calculated (Exact Mass) : 956.4

146960.doc -59- 201036941 化合物（5)實測值（M+) : 877.5 計算值（Exact Mass) : 877.4146960.doc -59- 201036941 Compound (5) Found (M+): 877.5 Calculated (Exact Mass) : 877.4

合成例1 :樹脂B丨之合成之燒航内流入氮氣而形成氮氣環境， 220份’一面擦挑一而‘敲；ρ 达丨以〇.〇2L/min向具有回流冷卻器、滴液漏斗及攪拌機之工l 然後加入乳酸乙酯。繼而，將其溶解 —面攪拌一面加熱至7〇。(：為止。於甲基丙烯酸84份、丙烯酸3,4-環氧基三環[5 2〗〇26]癸酯 (將式（I)所示之化合物與式（„)所示之化合物以5〇:5〇之莫耳比而混合）336份及乳酸乙酯140份中而製成溶液。使用滴液漏斗，歷時4小時將該溶解液滴加至保持為7〇t：之溫度之燒瓶内。另一方面，使用其它滴液漏斗，歷時4小時將使聚合起始劑2,2’-偶氮雙（2,4-二甲基戊腈）30份溶解於乳酸乙酯％份而成之溶液滴加至燒瓶内。於聚合起始劑之溶液之滴加結束後，於70°C下保持4小時，其後冷卻至室溫為止，從而獲得重量平均分子量Mw為8.〇χ1〇3，分子量分布為2 5，固形物成分為48%，酸值為50 mg-KOH/g之樹脂溶液BI。Synthesis Example 1: The synthesis of the resin B 流入 was carried out into the nitrogen gas to form a nitrogen atmosphere, 220 parts of the 'one side wiped one' and knocked; ρ reached 〇〇 2 L / min to the reflux cooler, the dropping funnel And the work of the mixer l then add ethyl lactate. Then, it was heated to 7 Torr while being stirred and stirred on the surface. (: up to 84 parts of methacrylic acid, 3,4-epoxytricyclo[5 2 〇 26] decyl acrylate (the compound represented by the formula (I) and the compound represented by the formula („) 5〇: 5〇 molar ratio mixed) 336 parts and 140 parts of ethyl lactate to make a solution. Using a dropping funnel, the dissolved droplets were added to a temperature of 7 〇t: for 4 hours. On the other hand, using another dropping funnel, 30 parts of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in % ethyl lactate for 4 hours. The resulting solution was added dropwise to the flask, and after completion of the dropwise addition of the solution of the polymerization initiator, it was kept at 70 ° C for 4 hours, and then cooled to room temperature to obtain a weight average molecular weight Mw of 8. Χ1〇3, a resin solution BI having a molecular weight distribution of 25, a solid content of 48%, and an acid value of 50 mg-KOH/g.

(II) .0 146960.doc -60- 201036941 關於上述樹脂之聚苯乙烯換算重量平均分子量之測定，係使用GPC法以如下之條件進行。裝置：HLC-8120GPC(東曹（股）製造）(II) .0 146960.doc -60- 201036941 The measurement of the polystyrene-equivalent weight average molecular weight of the above resin was carried out under the following conditions using a GPC method. Device: HLC-8120GPC (made by Tosoh Co., Ltd.)

管柱：TSK-GELG2000HXL 管柱溫度：40°C % 溶劑：THF(tetrahydrofuran，四氫α夫喃）流速：1 ·〇 mL/min 被檢測液固形物成分濃度：0.001〜0.01質量％ Ο θColumn: TSK-GELG2000HXL Column temperature: 40 ° C % Solvent: THF (tetrahydrofuran, tetrahydrofuran) Flow rate: 1 · 〇 mL / min The concentration of the solid content of the detected liquid: 0.001~0.01% by mass Ο θ

注入罝：5 0 pL 檢測器：RI(refractive index detector，折射率檢測器）校正用標準物質··TSKSTANDARDPOLYSTYRENEF-4〇、F-4、F-l、A-2500、A-500(東曹（股）製造）實施例6 (第4步驟） [著色組合物之製備] 〇將（B)著色劑：C. I.顏料藍15:6 20份 (B)丙烯酸系顏料分散劑 5份 (C)丙二醇單甲醚乙酸酯 137份混合，使用珠磨機將顏料充分分散： 1繼而，將 (A)著色劑：染料A1 3份 (D)樹脂：樹脂溶液B1 65份 (E)光聚合性化合物：二季戊四醇六丙烯酸酯（KAYARAD DPHA ;日本化藥（股）製造） 31份 (F)光聚合起始劑：N-苯甲醯氧基 -1-(4 -苯基硫烧基苯基） 146960.doc -61 - 201036941 辛烧-1-酮-2-亞胺（Irgacure OXE-Ol ; Ciba Japan公司製造） 9份 (C)溶劑：4-羥基-4-甲基-2-戊酮 229份混合而獲得著色組合物。實施例6A (第5步驟） [著色組合物之製備] 將（A)著色劑：染料A1 3份 (C)溶劑：4-羥基-4-曱基-2-戊酮 229份混合，然後於氮氣壓（0.3 MPa)下使其通過第1過濾器 (φ4·5 μηι，Pall公司製造，型號：HDCII J045047100，材質：聚丙烯）而獲得染料溶液。 (第6步驟）繼而，於氮氣壓（0.3 MPa)下使所獲得之染料溶液通過第 2過濾器（φθ.1 μιη，Mykrolis公司製造，型號：PTVW04700，材質：聚乙烯）。 (第7步驟）將（B)著色劑：C_ I.顏料藍15:6 20份 (B) 丙烯酸系顏料分散劑 5份 (C) 丙二醇單曱醚乙酸酯 137份混合，使用珠磨機將顏料充分分散而獲得顏料分散液。繼而，將（A)上述中所獲得之染料溶液 232份 (B)上述中所獲得之顏料分散液 162份 146960.doc -62- 201036941 (D) 樹脂：樹脂溶液B 1 65份Injection 罝: 5 0 pL Detector: RI (refractive index detector) Standard material for calibration ··TSKSTANDARDPOLYSTYRENEF-4〇, F-4, Fl, A-2500, A-500 (Dongcao (share) Manufacture) Example 6 (Step 4) [Preparation of coloring composition] ( (B) Colorant: CI Pigment Blue 15: 6 20 parts (B) Acrylic pigment dispersant 5 parts (C) Propylene glycol monomethyl ether 137 parts of acetate were mixed, and the pigment was sufficiently dispersed using a bead mill: 1 Next, (A) colorant: dye A1 3 parts (D) Resin: resin solution B1 65 parts (E) Photopolymerizable compound: dipentaerythritol Hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.) 31 parts (F) Photopolymerization initiator: N-benzylideneoxy-1-(4-phenylsulfanylphenyl) 146960.doc -61 - 201036941 octyl-1-keto-2-imine (Irgacure OXE-Ol; manufactured by Ciba Japan Co., Ltd.) 9 parts (C) solvent: 229 parts of 4-hydroxy-4-methyl-2-pentanone mixed A coloring composition is obtained. Example 6A (Step 5) [Preparation of coloring composition] (A) Coloring agent: Dye A1 3 parts (C) Solvent: 4-hydroxy-4-mercapto-2-pentanone 229 parts, and then A dye solution was obtained by passing a nitrogen gas (0.3 MPa) through a first filter (φ4·5 μηι, manufactured by Pall Corporation, model: HDCII J045047100, material: polypropylene). (Step 6) Then, the obtained dye solution was passed through a second filter (φθ.1 μηη, manufactured by Mykrolis Co., Ltd., model: PTVW04700, material: polyethylene) under a nitrogen pressure (0.3 MPa). (Step 7) (B) Colorant: C I. Pigment Blue 15: 6 20 parts (B) Acrylic Pigment Dispersant 5 parts (C) propylene glycol monoterpene ether acetate 137 parts, using a bead mill The pigment is sufficiently dispersed to obtain a pigment dispersion. Then, (A) 232 parts of the dye solution obtained in the above (B) 162 parts of the pigment dispersion obtained in the above 146960.doc -62- 201036941 (D) Resin: Resin solution B 1 65 parts

(E) 光聚合性化合物：二季戊四醇六丙烯酸酯（KAYARAD DPHA ;日本化藥（股）製造） 31份 (F) 光聚合起始劑：N-苯甲醯氧基_ι_(4-苯基硫烷基苯基）辛烷-1-酮 _2_亞胺（Irgacure OXE-01 ; Ciba Japan公司製造） 9份混合而獲得著色組合物。(E) Photopolymerizable compound: dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.) 31 parts (F) Photopolymerization initiator: N-benzylideneoxy_ι_(4-phenyl Sulfur-alkylphenyl)octane-1-one-2-imine (Irgacure OXE-01; manufactured by Ciba Japan Co., Ltd.) 9 parts were mixed to obtain a coloring composition.

❹ 實施例6B (第8步驟） [著色組合物之製備] 將（A)著色劑：染料A1 3份 (C)溶劑：4 -輕基-4-曱基-2-戊嗣 229份混合’並於乳氣壓（0.3 MPa)下使其通過第3過渡器（φ〇.ι μιη ’ Mykrolis公司製造，型號：PTVW04700，材質：聚乙烯）而獲得染料溶液。 (第9步驟） 20份 5份 137份將（B)著色劑：C. I.顏料藍15:6 (B) 丙稀酸系顏料分散劑 (C) 丙二醇單曱醚乙酸酯混合，使用珠磨機將顏料充分分散而獲得顏料分散液。繼而， 232份 162份 65份將（A)上述中所獲得之染料溶液 (B)上述中所獲得之顏料分散液 (D)樹脂：樹脂溶液B1 146960.doc -63- 201036941 (E) 光聚合性化合物：二季戊四醇六丙烯酸酯 (KAYARAD DPHA ；曰本化藥（股）製造） 31份 (F) 光聚合起始劑：N-苯甲醯氧基-1-(4-苯基硫烷基苯基）辛院-1-酮-2-亞胺（Irgacure OXE-01 ; Ciba Japan公司製造） 9份混合。 (第10步驟）繼而，於氮氣壓（0.3 MPa)下使所獲得之著色組合物通過第 4過濾器（φ4.5 μιη，Pall公司製造，型號：HDCII J045047100，材質：聚丙烯），從而獲得著色組合物。實施例6C (第5步驟） [著色組合物之製備] 將（A)著色劑：染料A1 3份 (C)溶劑：4-羥基-4-甲基-2-戊酮 229份混合，進而加入矽膠1份，然後於氮氣壓（0.3 MPa)下使其通過第1過濾器（φ4.5 μιη，Pall公司製造，型號：HDCII J045 047100，材質：聚丙烯）而獲得染料溶液。 (第6步驟）繼而，於氮氣壓（0.3 MPa)下使所獲得之染料溶液通過第 2過濾器（φθ.1 μιη，Mykrolis公司製造，型號：PTVW04700，材質：聚乙烯）。 (第7步驟）將（B)著色劑：C. I.顏料藍15··6 20份 146960.doc -64- 201036941 (B) 丙烯酸系顏料分散劑 5份 (C) 丙二醇單曱醚乙酸酯 137份混合，使用珠磨機將顏料充分分散而獲得顏料分散液。繼而，將（A)上述中所獲得之染料溶液 232份 (B)上述中所獲得之顏料分散液 162份 (D) 樹脂：樹脂溶液B1 65份实施 Example 6B (Step 8) [Preparation of coloring composition] (A) Colorant: Dye A1 3 parts (C) Solvent: 4 - Light-based 4-mercapto-2-pentanyl 229 parts mixed ' The dye solution was obtained by a third reactor (φ〇.ι μιη 'Mykrolis Co., Ltd., model: PTVW04700, material: polyethylene) under a milk pressure (0.3 MPa). (9th step) 20 parts 5 parts 137 parts (B) Colorant: CI Pigment Blue 15:6 (B) Acrylic acid pigment dispersant (C) Propylene glycol monoterpene ether acetate mixed, using a bead mill The pigment is sufficiently dispersed to obtain a pigment dispersion. Then, 232 parts of 162 parts of 65 parts of (A) the dye solution obtained in the above (B) The pigment dispersion liquid (D) obtained in the above: Resin solution B1 146960.doc -63 - 201036941 (E) Photopolymerization Compound: dipentaerythritol hexaacrylate (KAYARAD DPHA; manufactured by Sakamoto Chemical Co., Ltd.) 31 parts (F) Photopolymerization initiator: N-benzylideneoxy-1-(4-phenylsulfanyl) Phenyl) xinyuan-1-keto-2-imine (Irgacure OXE-01; manufactured by Ciba Japan Co., Ltd.) 9 parts mixed. (10th step) Then, the obtained coloring composition was passed through a 4th filter (φ4.5 μm, manufactured by Pall Co., Ltd., model: HDCII J045047100, material: polypropylene) under a nitrogen pressure (0.3 MPa). Coloring composition. Example 6C (5th step) [Preparation of coloring composition] (A) Colorant: Dye A1 3 parts (C) Solvent: 229 parts of 4-hydroxy-4-methyl-2-pentanone, and then added One part of the silicone rubber was passed through a first filter (φ 4.5 μm, manufactured by Pall Co., Ltd., model: HDCII J045 047100, material: polypropylene) under a nitrogen pressure (0.3 MPa) to obtain a dye solution. (Step 6) Then, the obtained dye solution was passed through a second filter (φθ.1 μηη, manufactured by Mykrolis Co., Ltd., model: PTVW04700, material: polyethylene) under a nitrogen pressure (0.3 MPa). (Step 7) (B) Colorant: CI Pigment Blue 15··6 20 parts 146960.doc -64- 201036941 (B) Acrylic pigment dispersant 5 parts (C) Propylene glycol monoterpene ether acetate 137 parts The mixture was mixed, and the pigment was sufficiently dispersed using a bead mill to obtain a pigment dispersion. Then, (A) 232 parts of the dye solution obtained in the above (B) 162 parts of the pigment dispersion obtained in the above (D) Resin: Resin solution B1 65 parts

(E) 光聚合性化合物：二季戊四醇六丙烯酸酯（KAYARAD 〇 DPHA ;曰本化藥（股）製造） 31份 (F)光聚合起始劑；N-苯甲醯氧基-1-(4-苯基硫烷基苯基）辛烧-1 -酮-2-亞胺（Irgacure OXE-O 1 ; Ciba Japan公司製造） 9份混合而獲得著色組合物。 [圖案之形成] 藉由旋塗法，將著色組合物塗佈於2英吋見方之玻璃基板（Eagle 2000 ;康寧（Corning)公司製造）上後，於100°C下預烘烤3分鐘。冷卻後，使該塗佈有著色組合物之基板與具有圖案之石英玻璃製光罩間隔100 μιη，然後大氣環境下，使用曝光機（TME-150RSK ; Topcon(股）製造）以150 mJ/cm2之曝光量（以365 nm為基準）而照射光。照射光之後，使上述塗膜於包含非離子系界面活性劑〇· 12%與氫氧化鉀0.04%之水系顯影液中、23°C下浸潰顯影80秒，水洗後，於烘箱中、220°C下進行20分鐘之後烘烤。放置冷卻後，使用膜厚測定裝置（DEKTAK3 ;日本真空技術（股）製 146960.doc -65- 201036941 造）測定所獲得之硬化圖案之膜厚，結果為2.2 μηι。實施例7〜1〇除將染料Α1變更為表1中所示之染料以外，以與實施例6 相同之方式獲得著色組合物及塗膜。(E) Photopolymerizable compound: dipentaerythritol hexaacrylate (KAYARAD 〇DPHA; manufactured by 曰本化制药(股)) 31 parts (F) photopolymerization initiator; N-benzylidene oxy-1-(4) -Phenylthioalkylphenyl)octane-1 -keto-2-imine (Irgacure OXE-O 1 ; manufactured by Ciba Japan Co., Ltd.) 9 parts were mixed to obtain a colored composition. [Formation of Pattern] The colored composition was applied onto a 2 inch square glass substrate (Eagle 2000; manufactured by Corning) by spin coating, and then prebaked at 100 ° C for 3 minutes. After cooling, the substrate coated with the colored composition was placed at a distance of 100 μm from the patterned quartz glass mask, and then exposed to an exposure machine (TME-150RSK; Topcon) at 150 mJ/cm 2 in an atmosphere. The amount of exposure (based on 365 nm) illuminates the light. After the light was irradiated, the coating film was immersed and developed in an aqueous developing solution containing a nonionic surfactant 〇·12% and potassium hydroxide 0.04% at 23° C. for 80 seconds, washed with water, and then placed in an oven at 220°C. Bake after 20 minutes at °C. After the film was allowed to stand for cooling, the film thickness of the obtained hardened pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd., 146960.doc -65-201036941), and it was 2.2 μm. Example 7 to 1 A coloring composition and a coating film were obtained in the same manner as in Example 6 except that the dye oxime 1 was changed to the dye shown in Table 1.

實施例 7Α〜1〇Α、7Β〜10Β、7C~10C 除將染料A1變更為表1中所示之染料以外，分別以與實施例6A、實施例6B以及實施例6C相同之方式獲得著色組合物及塗膜。 [異物評價] 使用表面形狀測定顯微鏡（VF-75 10 ;基恩斯（Keyence)製造）’以250倍之倍率觀察所獲得之圖案，將視野内之黑點狀或白點狀之異物個數為20個以下之情形判定為〇。將其結果示於表1。 [表1] 染料異物例 6 實施例7 實施例8 實施例9 實施例10 A1 —------ A2 A3 A4 A5 〇〇〇〇〇又，只施例7A〜實施例10C中亦均獲得分別與實施例 6〜10相同之結果。 [產業上之可利用性] 根據本發明之磺醯胺化合物之製造方法，可減少異物之 ^生’且可廣泛地利用於使用含有複數種成分，例如染料顏料等溶解性或非溶解性成分之著色組合物之各種膜或膜等的製造方法。 146960.doc -66 - 201036941 根據本發明，可製造一種磺醯胺化合物，於使用含有該石頁酿胺化合物之組合物形成塗膜時，可減少異物之產生。又，藉由使用以此種方法所獲得之確驢胺化合物，可製造此夠形成更南精度之著色圖案之著色組合物。 ΟExample 7 Α~1〇Α, 7Β~10Β, 7C~10C A coloring combination was obtained in the same manner as in Example 6A, Example 6B, and Example 6C except that the dye A1 was changed to the dye shown in Table 1. Matter and film. [Foreign object evaluation] The obtained pattern was observed at a magnification of 250 times using a surface shape measuring microscope (VF-75 10; manufactured by Keyence), and the number of black spots or white spots in the field of view was 20. The following cases are judged as 〇. The results are shown in Table 1. [Table 1] Dye foreign matter Example 6 Example 7 Example 8 Example 9 Example 10 A1 ------- A2 A3 A4 A5 Further, only Example 7A to Example 10C are also The same results as in Examples 6 to 10 were obtained, respectively. [Industrial Applicability] According to the method for producing a sulfonamide compound of the present invention, it is possible to reduce the occurrence of foreign matter and to be widely used for the use of a soluble or insoluble component containing a plurality of components such as dye pigments. A method of producing various films, films, and the like of the coloring composition. 146960.doc -66 - 201036941 According to the present invention, a sulfonamide compound can be produced, and when a coating film is formed using the composition containing the ceramide compound, the generation of foreign matter can be reduced. Further, by using the decylamine compound obtained by such a method, the coloring composition capable of forming a more southerly colored pattern can be produced. Ο

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Claims

201036941 七、申請專利範圍： 1 · 一種磺醯胺化合物之製造方法，其包括：第1步驟，將具有選自由-S〇3·及-S03H所組成群中之至少一種的化合物磺醯胺化；第2步驟，至少利用選自由酸性水溶液及6〇。〇以上、 951以下之水所組成群中的至少一種清洗第丨步驟中所獲得之反應物；及第3步驟，使第2步驟中所獲得之清洗物乾燥而獲得磺 ^ 醯胺化合物。 2.如請求項1之磺醯胺化合物之製造方法，其中酸性水溶液係pH值為5以下之酸性水溶液。 3·如請求項1之磺醯胺化合物之製造方法，其中酸性水溶液係選自由鹽酸水溶液及乙酸水溶液所組成群中之至少 —種。 4.如睛求項1之磺醯胺化合物之製造方法，其中具有選自 Ο 由-s〇3_及-s〇3H所組成群中之至少一種基的化合物係包合％p星骨架之化合物。如明泉項1之磺醯胺化合物之製造方法，其中具有選自 * 由-S〇3.及-S〇3H所組成群中之至少一種基的化合物係式 (1)所示之化合物：201036941 VII. Patent Application Range: 1 . A method for producing a sulfonamide compound, comprising: a first step of sulfonating a compound having at least one selected from the group consisting of -S〇3· and -S03H The second step is at least selected from the group consisting of an acidic aqueous solution and 6 Å. At least one of the above-mentioned groups of waters of 951 or less is used to clean the reactants obtained in the second step; and in the third step, the washings obtained in the second step are dried to obtain a sulfonamide compound. 2. The method for producing a sulfonamide compound according to claim 1, wherein the acidic aqueous solution is an acidic aqueous solution having a pH of 5 or less. 3. The method for producing a sulfonamide compound according to claim 1, wherein the acidic aqueous solution is at least one selected from the group consisting of aqueous hydrochloric acid solution and aqueous acetic acid solution. 4. The method for producing a sulfonamide compound according to item 1, wherein the compound having at least one selected from the group consisting of -s-s〇3_ and -s〇3H is included in the %p star skeleton. Compound. A method for producing a sulfonamide compound according to the item 1, wherein the compound having at least one selected from the group consisting of -S〇3. and -S〇3H is a compound represented by the formula (1):

146960.doc 201036941 (式（1)中，R1〜R15分別獨立表示氫原子、_Rle、_〇h -OR16 ' -C02H -S03-、-S03Na、-s〇3K或 -C02R1 -S03H，且R1〜R15中之一者表示_s〇3_， R16表示碳數為1〜10之一價飽和烴基，該飽和烴基中所包含之氫原子亦可由鹵素原子、經基或碳數為卜ι〇之烧氧基取代，該飽和烴基中所包含之_CH^亦可取代成_〇_ 、-CO-或-NR17-, R表示氫原子或碳數為之一價飽和烴基）。 6. 一種著色組合物之製造方法，其包括：第1步驟，將具有選自由_s〇3_&_s〇3Hm組成群中之至少一種基的化合物磺醯胺化；第2步驟，至少利用選自由酸性水溶液及6(TC以上、 95°C以下之水所組成群中的至少—種清洗^步驟中所獲得之反應物； '步驟使第2步驟中所獲得之清洗物乾燥而獲得石黃醯胺化合物；及第4步驟，⑯第3步驟中所獲得之績醯胺化合物與選自由顏料或顏料分散液（B)、溶劑（〇、樹脂⑼、光聚合性化口物（E)以及光聚合起始劑所組成群中之至混合。 146960.doc 201036941 四、指定代表圖： (一) 本案指定代表圖為：（無） (二) 本代表圖之元件符號簡單說明：五、本案若有化學式時，請揭示最能顯示發明特徵的化學式：146960.doc 201036941 (In the formula (1), R1 to R15 independently represent a hydrogen atom, _Rle, _〇h -OR16 ' -C02H -S03-, -S03Na, -s〇3K or -C02R1 -S03H, and R1~ One of R15 represents _s〇3_, and R16 represents a monovalent saturated hydrocarbon group having a carbon number of 1 to 10, and the hydrogen atom contained in the saturated hydrocarbon group may also be a halogen atom, a trans group or a carbon number. The oxy group is substituted, and the _CH^ contained in the saturated hydrocarbon group may be substituted with _〇_, -CO- or -NR17-, and R represents a hydrogen atom or a monovalent saturated hydrocarbon group. A method for producing a coloring composition, comprising: a first step of sulfonating a compound having at least one selected from the group consisting of _s〇3_&_s〇3Hm; the second step, at least using a free acidic aqueous solution and a reactant obtained in at least one of the steps of the group consisting of 6 (TC or more and 95 ° C or less); the step of drying the washing material obtained in the second step to obtain the sallow a guanamine compound; and the guanamine compound obtained in the third step, 16th step 3, and a pigment- or pigment dispersion (B), a solvent (〇, a resin (9), a photopolymerizable mouth (E), and Photopolymerization initiators are grouped into a mixture. 146960.doc 201036941 IV. Designation of representative drawings: (1) The representative representative of the case is: (none) (2) The symbol of the symbol of the representative figure is simple: 5. If there is a chemical formula, please reveal the chemical formula that best shows the characteristics of the invention:

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