TW201800496A - Compound, photosensitive resin composition comprising the same and color filter - Google Patents

Compound, photosensitive resin composition comprising the same and color filter Download PDF

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TW201800496A
TW201800496A TW106119655A TW106119655A TW201800496A TW 201800496 A TW201800496 A TW 201800496A TW 106119655 A TW106119655 A TW 106119655A TW 106119655 A TW106119655 A TW 106119655A TW 201800496 A TW201800496 A TW 201800496A
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photosensitive resin
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TWI673325B (en
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馮新惠
趙南植
申先雄
金圭泳
李英
辛明曄
李貞和
徐光源
鄭周昊
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三星Sdi股份有限公司
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Abstract

Provided are a compound represented by Chemical Formula 1, a photosensitive resin composition including the same, and color filter including a photosensitive resin film manufactured using the photosensitive resin composition. [Chemical Formula 1] (In Chemical Formula 1, each substituent is the same as defined in the specification.).

Description

化合物、包含其的感光性樹脂組成物以及彩色濾光片Compound, photosensitive resin composition containing the same, and color filter

本公開涉及一種新穎化合物、包含其的感光性樹脂組成物以及彩色濾光片。The present disclosure relates to a novel compound, a photosensitive resin composition containing the same, and a color filter.

在諸多種類的顯示器中,液晶顯示器裝置具有輕、薄、成本低、操作功耗低、及對積體電路的支持性高的優點,且已更廣泛地用於膝上型電腦、監視器、及電視螢幕。液晶顯示器裝置包括下部基板及上部基板,在下部基板上形成有黑色矩陣、彩色濾光片、及氧化銦錫像素電極,在上部基板上形成有包括液晶層、薄膜電晶體、及電容器層的主動電路部分以及氧化銦錫像素電極。通過按照預定次序依序堆疊多個彩色濾光片(一般來說,由三原色(例如紅色(R)、綠色(G)、及藍色(B))形成)以形成每一像素而在像素區中形成彩色濾光片,且以預定圖案將黑色矩陣層設置在透明基板上以形成各像素之間的邊界。作為形成彩色濾光片的各種方法中的一種方法,顏料分散方法通過重複一系列以下製程來提供經著色薄膜:例如將包含著色劑的感光性樹脂組成物塗布在包括黑色矩陣的透明基板上,將所形成的圖案曝光,用溶劑移除未被曝光的部分,以及對其進行熱固化。用於根據顏料分散方法製造彩色濾光片的感光性樹脂組成物一般包含黏合劑樹脂、光可聚合單體、光聚合引發劑、溶劑、及其他添加劑。具有所述特性的顏料分散方法積極地應用於製造例如手機、膝上型電腦、監視器、及電視等液晶顯示器。然而,用於使用顏料分散方法的彩色濾光片的感光性樹脂組成物具有某些缺點,這是因為難以將顏料粉末精細地粉碎、即使顏料粉末得以分散仍需要各種添加劑來穩定分散液且需要複雜的製程、以及難以進一步地在複雜的儲存條件及運輸條件下維持顏料分散液的最優品質。另外,使用顏料型感光性樹脂組成物製造的彩色濾光片因顏料細微性而在亮度及對比度方面存在限制。因此,需要開發一種具有與顏料的耐熱性及耐化學性類似的耐熱性及耐化學性的染料。Among many types of displays, liquid crystal display devices have the advantages of being light, thin, low in cost, low in operating power consumption, and highly supportive for integrated circuits, and have been more widely used in laptops, monitors, And TV screen. The liquid crystal display device includes a lower substrate and an upper substrate, and a black matrix, a color filter, and an indium tin oxide pixel electrode are formed on the lower substrate, and an active layer including a liquid crystal layer, a thin film transistor, and a capacitor layer is formed on the upper substrate. The circuit portion and the indium tin oxide pixel electrode. By sequentially stacking a plurality of color filters (generally formed of three primary colors (for example, red (R), green (G), and blue (B))) in a predetermined order to form each pixel in the pixel region A color filter is formed in the medium, and a black matrix layer is disposed on the transparent substrate in a predetermined pattern to form a boundary between the pixels. As one of various methods of forming a color filter, the pigment dispersion method provides a colored film by repeating a series of processes: for example, coating a photosensitive resin composition containing a colorant on a transparent substrate including a black matrix, The formed pattern is exposed, the unexposed portion is removed with a solvent, and it is thermally cured. The photosensitive resin composition for producing a color filter according to the pigment dispersion method generally contains a binder resin, a photopolymerizable monomer, a photopolymerization initiator, a solvent, and other additives. The pigment dispersion method having the above characteristics is actively applied to the manufacture of liquid crystal displays such as mobile phones, laptops, monitors, and televisions. However, the photosensitive resin composition for a color filter using a pigment dispersion method has certain disadvantages in that it is difficult to finely pulverize the pigment powder, and even if the pigment powder is dispersed, various additives are required to stabilize the dispersion and it is required Complex processes, and the difficulty of further maintaining the optimum quality of the pigment dispersion under complex storage conditions and transport conditions. Further, a color filter produced using a pigment-type photosensitive resin composition has limitations in brightness and contrast due to pigment fineness. Therefore, there is a need to develop a dye having heat resistance and chemical resistance similar to those of a pigment.

本發明實施例提供一種新穎化合物。Embodiments of the invention provide a novel compound.

另一實施例提供一種包含所述化合物的感光性樹脂組成物。Another embodiment provides a photosensitive resin composition comprising the compound.

再一實施例提供一種彩色濾光片,所述彩色濾光片包括使用所述感光性樹脂組成物製造的感光性樹脂膜。Still another embodiment provides a color filter including a photosensitive resin film produced using the photosensitive resin composition.

本發明的實施例提供一種由化學式1表示的化合物。 [化學式1]

Figure TW201800496AD00001
在化學式1中, R1 為鹵素原子、經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基, R2 為經取代或未經取代的C3至C20脂環族環狀基、或者經取代或未經取代的C6至C20芳基,其限制條件是所述芳基僅具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基, R3 至R5 獨立地為經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基, m及n獨立地為介於1至5範圍內的整數,且 L由化學式2表示, [化學式2]
Figure TW201800496AD00002
其中,在化學式2中, L1 為-O(C=O)-或-S-,且 A為經取代或未經取代的C1至C20烷基、經取代或未經取代的C3至C20脂環族環狀基、經取代或未經取代的C6至C20芳基、或者經取代或未經取代的C2至C20雜芳基。An embodiment of the present invention provides a compound represented by Chemical Formula 1. [Chemical Formula 1]
Figure TW201800496AD00001
In Chemical Formula 1, R 1 is a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aromatic group. And R 2 is a substituted or unsubstituted C 3 to C 20 alicyclic cyclic group, or a substituted or unsubstituted C 6 to C 20 aryl group, with the proviso that the aryl group has only at least one selected from the group consisting of a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 alkylthio group, R 3 to R 5 are independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group, m and n is independently an integer ranging from 1 to 5, and L is represented by Chemical Formula 2, [Chemical Formula 2]
Figure TW201800496AD00002
Wherein, in Chemical Formula 2, L 1 is -O(C=O)- or -S-, and A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 fat. a cyclocyclic group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group.

所述R1 可為經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基。The R 1 may be a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group.

所述R2 可為經取代或未經取代的金剛烷基、或者經取代或未經取代的苯基。所述苯基僅具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基。The R 2 may be a substituted or unsubstituted adamantyl group, or a substituted or unsubstituted phenyl group. The phenyl group has only at least one selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to a substituent in the C10 alkylthio group.

所述R2 可為「所述未經取代的金剛烷基」或者「所述苯基僅具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基」。The R 2 may be "the unsubstituted adamantyl group" or "the phenyl group has only at least one selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, substituted or not Substituted C1 to C10 alkoxy groups, and substituted or unsubstituted substituents in the C1 to C10 alkylthio group.

所述R3 至R5 可獨立地為經取代或未經取代的C1至C20烷基。The R 3 to R 5 may independently be a substituted or unsubstituted C1 to C20 alkyl group.

所述L可由選自化學式3至化學式7中的一者表示。 [化學式3]

Figure TW201800496AD00003
[化學式4]
Figure TW201800496AD00004
[化學式5]
Figure TW201800496AD00005
[化學式6]
Figure TW201800496AD00006
[化學式7]
Figure TW201800496AD00007
在化學式3至化學式7中, R6 為經取代或未經取代的C1至C10烷基、經取代或未經取代的氨基、或者經取代或未經取代的醯基, R7 至R9 獨立地為羥基或者經取代或未經取代的C1至C10烷基,其限制條件是R7 及R8 中的至少一者為羥基, R10 為經取代或未經取代的C1至C10烷基, o及p獨立地為介於1至3範圍內的整數,其限制條件是2 ≤ o + p ≤ 5,且 q為介於0至4範圍內的整數。The L may be represented by one selected from Chemical Formula 3 to Chemical Formula 7. [Chemical Formula 3]
Figure TW201800496AD00003
[Chemical Formula 4]
Figure TW201800496AD00004
[Chemical Formula 5]
Figure TW201800496AD00005
[Chemical Formula 6]
Figure TW201800496AD00006
[Chemical Formula 7]
Figure TW201800496AD00007
In Chemical Formula 3 to Chemical Formula 7, R 6 is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted fluorenyl group, and R 7 to R 9 are independently Is a hydroxy group or a substituted or unsubstituted C1 to C10 alkyl group, with the proviso that at least one of R 7 and R 8 is a hydroxyl group, and R 10 is a substituted or unsubstituted C1 to C10 alkyl group, o and p are independently integers in the range of 1 to 3, with the constraint being 2 ≤ o + p ≤ 5, and q is an integer ranging from 0 to 4.

所述經取代或未經取代的氨基可由化學式8表示。 [化學式8]

Figure TW201800496AD00008
在化學式8中, Rx 為經取代或未經取代的C1至C10烷基,且 z為介於0至5範圍內的整數。The substituted or unsubstituted amino group can be represented by Chemical Formula 8. [Chemical Formula 8]
Figure TW201800496AD00008
In Chemical Formula 8, R x is a substituted or unsubstituted C1 to C10 alkyl group, and z is an integer ranging from 0 to 5.

所述經取代或未經取代的醯基可由化學式9表示。 [化學式9]

Figure TW201800496AD00009
The substituted or unsubstituted fluorenyl group can be represented by Chemical Formula 9. [Chemical Formula 9]
Figure TW201800496AD00009

所述R6 可為叔丁基、所述由化學式8表示的取代基、或所述由化學式9表示的取代基。The R 6 may be a tert-butyl group, the substituent represented by Chemical Formula 8, or the substituent represented by Chemical Formula 9.

所述R7 至R9 可獨立地為羥基或叔丁基,其限制條件是R7 及R8 中的至少一者為羥基。The R 7 to R 9 may independently be a hydroxyl group or a t-butyl group, with the proviso that at least one of R 7 and R 8 is a hydroxyl group.

所述R10 可為經取代或未經取代的甲基、經取代或未經取代的乙基、經取代或未經取代的丙基、經取代或未經取代的丁基、或者經取代或未經取代的戊基。The R 10 may be substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, or substituted or Unsubstituted pentyl.

化學式1可由化學式10-1或化學式10-2表示。 [化學式10-1]

Figure TW201800496AD00010
[化學式10-2]
Figure TW201800496AD00011
在化學式10-1及化學式10-2中, R1 為鹵素原子、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基, R2 為經取代或未經取代的C3至C20脂環族環狀基、或者經取代或未經取代的C6至C20芳基,其限制條件是所述芳基具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基, R3 至R5 獨立地為經取代或未經取代的C1至C20烷基,且 L由化學式2表示, [化學式2]
Figure TW201800496AD00012
其中,在化學式2中, L1 為-O(C=O)-,且 A為經取代或未經取代的C1至C20烷基、經取代或未經取代的C3至C20脂環族環狀基、或者經取代或未經取代的C6至C20芳基。Chemical Formula 1 can be represented by Chemical Formula 10-1 or Chemical Formula 10-2. [Chemical Formula 10-1]
Figure TW201800496AD00010
[Chemical Formula 10-2]
Figure TW201800496AD00011
In Chemical Formula 10-1 and Chemical Formula 10-2, R 1 is a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group, and R 2 is a a substituted or unsubstituted C3 to C20 alicyclic cyclic group, or a substituted or unsubstituted C6 to C20 aryl group, with the proviso that the aryl group has at least one selected from a halogen atom, substituted or not a substituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 alkylthio group, and R 3 to R 5 are independently a substituted or unsubstituted C1 to C20 alkyl group, and L is represented by Chemical Formula 2, [Chemical Formula 2]
Figure TW201800496AD00012
Wherein, in Chemical Formula 2, L 1 is -O(C=O)-, and A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring. A substituted or unsubstituted C6 to C20 aryl group.

化學式1可由選自化學式1-1至化學式1-12中的一者表示。 [化學式1-1]

Figure TW201800496AD00013
[化學式1-2]
Figure TW201800496AD00014
[化學式1-3]
Figure TW201800496AD00015
[化學式1-4]
Figure TW201800496AD00016
[化學式1-5]
Figure TW201800496AD00017
[化學式1-6]
Figure TW201800496AD00018
[化學式1-7]
Figure TW201800496AD00019
[化學式1-8]
Figure TW201800496AD00020
[化學式1-9]
Figure TW201800496AD00021
[化學式1-10]
Figure TW201800496AD00022
[化學式1-11]
Figure TW201800496AD00023
[化學式1-12]
Figure TW201800496AD00024
Chemical Formula 1 can be represented by one selected from Chemical Formula 1-1 to Chemical Formula 1-12. [Chemical Formula 1-1]
Figure TW201800496AD00013
[Chemical Formula 1-2]
Figure TW201800496AD00014
[Chemical Formula 1-3]
Figure TW201800496AD00015
[Chemical Formula 1-4]
Figure TW201800496AD00016
[Chemical Formula 1-5]
Figure TW201800496AD00017
[Chemical Formula 1-6]
Figure TW201800496AD00018
[Chemical Formula 1-7]
Figure TW201800496AD00019
[Chemical Formula 1-8]
Figure TW201800496AD00020
[Chemical Formula 1-9]
Figure TW201800496AD00021
[Chemical Formula 1-10]
Figure TW201800496AD00022
[Chemical Formula 1-11]
Figure TW201800496AD00023
[Chemical Formula 1-12]
Figure TW201800496AD00024

由化學式1表示的化合物可為染料。The compound represented by Chemical Formula 1 may be a dye.

所述染料可在450 nm至600 nm的波長範圍內具有最大吸光度。The dye has a maximum absorbance in the wavelength range from 450 nm to 600 nm.

另一實施例提供一種包含所述化合物作為染料的感光性樹脂組成物。Another embodiment provides a photosensitive resin composition comprising the compound as a dye.

包含所述化合物作為染料的所述感光性樹脂組成物可進一步包含黏合劑樹脂、顏料、光可聚合單體、光聚合引發劑、及溶劑。The photosensitive resin composition containing the compound as a dye may further contain a binder resin, a pigment, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.

以所述感光性樹脂組成物的總量計,可包含5重量%至20重量%的量的所述染料。The dye may be contained in an amount of from 5% by weight to 20% by weight based on the total of the photosensitive resin composition.

以所述感光性樹脂組成物的總量計,可包含10重量%至15重量%的量的所述染料。The dye may be contained in an amount of 10% by weight to 15% by weight based on the total amount of the photosensitive resin composition.

所述顏料可包括藍色顏料。The pigment may comprise a blue pigment.

所述黏合劑樹脂可包括丙烯酸系黏合劑樹脂、卡多系(cardo-based)黏合劑樹脂、或其組合。The binder resin may include an acrylic binder resin, a cardo-based binder resin, or a combination thereof.

以所述感光性樹脂組成物的總量計,所述感光性樹脂組成物可包含:1重量%至10重量%的所述黏合劑樹脂;45重量%至80重量%的包含所述染料及所述顏料的著色劑;1重量%至5重量%的所述光可聚合單體;0.1重量%至3重量%的所述光聚合引發劑;以及餘量為所述溶劑。The photosensitive resin composition may include: 1% by weight to 10% by weight of the binder resin; and 45% by weight to 80% by weight of the dye and the dye, based on the total amount of the photosensitive resin composition a color former of the pigment; 1% by weight to 5% by weight of the photopolymerizable monomer; 0.1% by weight to 3% by weight of the photopolymerization initiator; and the balance being the solvent.

所述感光性樹脂組成物可進一步包含以下添加劑:丙二酸;3-氨基-1,2-丙二醇;矽烷系偶合劑;流平劑;氟系表面活性劑;自由基聚合引發劑;或其組合。The photosensitive resin composition may further comprise the following additives: malonic acid; 3-amino-1,2-propanediol; a decane-based coupling agent; a leveling agent; a fluorine-based surfactant; a radical polymerization initiator; combination.

另一實施例提供一種彩色濾光片,所述彩色濾光片包括使用所述感光性樹脂組成物製造的感光性樹脂膜。Another embodiment provides a color filter including a photosensitive resin film produced using the photosensitive resin composition.

在以下詳細說明中包含本發明的其他實施例。Other embodiments of the invention are included in the detailed description which follows.

根據實施例的所述化合物具有色彩特性,且當使用包含所述化合物的感光性樹脂組成物時,可提供具有改善的亮度、耐熱性、及可加工性的彩色濾光片。The compound according to the embodiment has color characteristics, and when a photosensitive resin composition containing the compound is used, a color filter having improved brightness, heat resistance, and processability can be provided.

在下文中詳細闡述本發明的實施例。然而,這些實施例為示範性的,本發明不限於此並且本發明由權利要求的範圍所界定。Embodiments of the invention are set forth in detail below. However, the embodiments are exemplary, and the invention is not limited thereto and the invention is defined by the scope of the claims.

在本說明書中,當不另外提供特定定義時,術語「經取代」是指至少一個氫經至少一個選自以下的取代基置換:鹵素原子(F、Cl、Br或I)、羥基、硝基、氰基、氨基(NH2 、NH(R200 )或N(R201 )(R202 ),其中R200 、R201 及R202 為相同或不同的,且獨立地為C1至C10烷基或C6至C20芳基)、脒基、肼基、腙基、羧基、經取代或未經取代的烷基、經取代或未經取代的烯基、經取代或未經取代的炔基、經取代或未經取代的脂環族有機基、經取代或未經取代的芳基以及經取代或未經取代的雜環基。In the present specification, the term "substituted" means that at least one hydrogen is substituted with at least one substituent selected from the group consisting of a halogen atom (F, Cl, Br or I), a hydroxyl group, a nitro group, when a specific definition is not additionally provided. a cyano group, an amino group (NH 2 , NH(R 200 ) or N(R 201 )(R 202 ), wherein R 200 , R 201 and R 202 are the same or different and independently a C1 to C10 alkyl group or C6 to C20 aryl), fluorenyl, fluorenyl, fluorenyl, carboxy, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted Or an unsubstituted alicyclic organic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

在本說明書中,當不另外提供特定定義時,「烷基」是指C1至C20烷基且尤其C1至C15烷基,「環烷基」是指C3至C20環烷基且尤其C3至C18環烷基,「烷氧基」是指C1至C20烷氧基且尤其C1至C18烷氧基,「芳基」是指C6至C20芳基且尤其C6至C18芳基,「烯基」是指C2至C20烯基且尤其C2至C18烯基,「伸烷基」是指C1至C20伸烷基且尤其C1至C18伸烷基,且「伸芳基」是指C6至C20伸芳基且尤其C6至C16伸芳基。In the present specification, when a specific definition is not additionally provided, "alkyl" means a C1 to C20 alkyl group and especially a C1 to C15 alkyl group, and "cycloalkyl group" means a C3 to C20 cycloalkyl group and especially C3 to C18. Cycloalkyl, "alkoxy" means C1 to C20 alkoxy and especially C1 to C18 alkoxy, "aryl" means C6 to C20 aryl and especially C6 to C18 aryl, "alkenyl" is Refers to C2 to C20 alkenyl and especially C2 to C18 alkenyl, "alkylene" refers to C1 to C20 alkyl and especially C1 to C18 alkyl, and "extended aryl" refers to C6 to C20 extended aryl And especially C6 to C16 extended aryl.

在本說明書中,當不另外提供特定定義時,「(甲基)丙烯酸酯是指「丙烯酸酯」及「甲基丙烯酸酯」兩者,並且「(甲基)丙烯酸」是指「丙烯酸」及「甲基丙烯酸」。In the present specification, when a specific definition is not provided, "(meth)acrylate means both "acrylate" and "methacrylate", and "(meth)acrylic" means "acrylic acid" and "Methacrylate".

在本說明書中,當不另外提供特定定義時,術語「組合」是指混合或共聚合。另外,「共聚合」是指嵌段共聚合至無規共聚合,且「共聚物」是指嵌段共聚物至無規共聚物。In the present specification, the term "combination" means mixing or copolymerization when a specific definition is not additionally provided. Further, "copolymerization" means block copolymerization to random copolymerization, and "copolymer" means a block copolymer to a random copolymer.

在本說明書的化學式中,除非另外提供特定定義,否則當化學鍵並未繪製在應給出處時,氫原子鍵結在所述位置處。In the chemical formula of the present specification, unless a specific definition is additionally provided, when a chemical bond is not drawn at a position to be given, a hydrogen atom is bonded at the position.

在本說明書中,卡多系樹脂是指在其骨架中包含至少一個選自化學式11-1至化學式11-11中的官能基的樹脂。In the present specification, the card poly-resin refers to a resin containing at least one functional group selected from the chemical formula 11-1 to the chemical formula 11-11 in its skeleton.

在本說明書中,當不另外提供特定定義時,「*」指示連接相同或不同原子或化學式的點。In the present specification, when a specific definition is not additionally provided, "*" indicates a point connecting the same or different atoms or chemical formulas.

本發明實施例提供一種由化學式1表示的化合物。 [化學式1]

Figure TW201800496AD00025
在化學式1中, R1 為鹵素原子、經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基, R2 為經取代或未經取代的C3至C20脂環族環狀基、或者經取代或未經取代的C6至C20芳基,其限制條件是所述芳基僅具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基, R3 至R5 獨立地為經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基, m及n獨立地為介於1至5範圍內的整數,且 L由化學式2表示, [化學式2]
Figure TW201800496AD00026
其中,在化學式2中, L1 為-O(C=O)-或-S-,且 A為經取代或未經取代的C1至C20烷基、經取代或未經取代的C3至C20脂環族環狀基、經取代或未經取代的C6至C20芳基、或者經取代或未經取代的C2至C20雜芳基。An embodiment of the present invention provides a compound represented by Chemical Formula 1. [Chemical Formula 1]
Figure TW201800496AD00025
In Chemical Formula 1, R 1 is a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aromatic group. And R 2 is a substituted or unsubstituted C 3 to C 20 alicyclic cyclic group, or a substituted or unsubstituted C 6 to C 20 aryl group, with the proviso that the aryl group has only at least one selected from the group consisting of a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 alkylthio group, R 3 to R 5 are independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group, m and n is independently an integer ranging from 1 to 5, and L is represented by Chemical Formula 2, [Chemical Formula 2]
Figure TW201800496AD00026
Wherein, in Chemical Formula 2, L 1 is -O(C=O)- or -S-, and A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 fat. a cyclocyclic group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group.

根據實施例的化合物由化學式1表示,且與傳統染料相比具有優異的頻譜特性、高的莫耳消光係數(molar extinction coefficient)、及關於例如環己酮、丙二醇單甲醚乙酸酯等有機溶劑的優異的溶解度。The compound according to the examples is represented by Chemical Formula 1, and has excellent spectral characteristics, a high molar extinction coefficient, and organic substances such as cyclohexanone, propylene glycol monomethyl ether acetate, etc., compared with the conventional dye. Excellent solubility of solvents.

舉例來說,R1 可為經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基。當R1 為鹵素原子時,耐熱性會比當R1 為經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基時劣化。For example, R 1 may be a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group. When R 1 is a halogen atom, the heat resistance may be higher than when R 1 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted group. The C6 to C20 aryl group deteriorates.

R2 可為經取代或未經取代的金剛烷基、或者經取代或未經取代的苯基。苯基可僅具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基。R 2 may be substituted or unsubstituted adamantyl, or substituted or unsubstituted phenyl. The phenyl group may have only at least one C1 to C10 alkyl group selected from a halogen atom, a substituted or unsubstituted group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 group. a substituent in an alkylthio group.

舉例來說,當R2 為經三氟甲基取代的苯基時,耐熱性會比當R2 為經鹵素原子、烷基、烷氧基、或烷硫基取代的苯基時劣化。For example, when R 2 is a triphenylmethyl-substituted phenyl group, heat resistance may be deteriorated when R 2 is a phenyl group substituted with a halogen atom, an alkyl group, an alkoxy group, or an alkylthio group.

舉例來說,R2 可為「未經取代的金剛烷基」或者「所述苯基僅具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基」。For example, R 2 may be "unsubstituted adamantyl group" or "the phenyl group has only at least one selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, substituted or not Substituted C1 to C10 alkoxy groups, and substituted or unsubstituted substituents in the C1 to C10 alkylthio group.

R3 至R5 可獨立地為經取代或未經取代的C1至C20烷基。R 3 to R 5 may independently be a substituted or unsubstituted C1 to C20 alkyl group.

L可由選自化學式3至化學式7中的一者表示。 [化學式3]

Figure TW201800496AD00027
[化學式4]
Figure TW201800496AD00028
[化學式5]
Figure TW201800496AD00029
[化學式6]
Figure TW201800496AD00030
[化學式7]
Figure TW201800496AD00031
在化學式3至化學式7中, R6 為經取代或未經取代的C1至C10烷基、經取代或未經取代的氨基、或者經取代或未經取代的醯基, R7 至R9 獨立地為羥基或者經取代或未經取代的C1至C10烷基,其限制條件是R7 及R8 中的至少一者為羥基, R10 為經取代或未經取代的C1至C10烷基, o及p獨立地為介於1至3範圍內的整數,其限制條件是2 ≤ o + p ≤ 5,且 q為介於0至4範圍內的整數。L may be represented by one selected from Chemical Formula 3 to Chemical Formula 7. [Chemical Formula 3]
Figure TW201800496AD00027
[Chemical Formula 4]
Figure TW201800496AD00028
[Chemical Formula 5]
Figure TW201800496AD00029
[Chemical Formula 6]
Figure TW201800496AD00030
[Chemical Formula 7]
Figure TW201800496AD00031
In Chemical Formula 3 to Chemical Formula 7, R 6 is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted fluorenyl group, and R 7 to R 9 are independently Is a hydroxy group or a substituted or unsubstituted C1 to C10 alkyl group, with the proviso that at least one of R 7 and R 8 is a hydroxyl group, and R 10 is a substituted or unsubstituted C1 to C10 alkyl group, o and p are independently integers in the range of 1 to 3, with the constraint being 2 ≤ o + p ≤ 5, and q is an integer ranging from 0 to 4.

舉例來說,經取代或未經取代的氨基可由化學式8表示。 [化學式8]

Figure TW201800496AD00032
在化學式8中, Rx 為經取代或未經取代的C1至C10烷基,且 z為介於0至5範圍內的整數。For example, a substituted or unsubstituted amino group can be represented by Chemical Formula 8. [Chemical Formula 8]
Figure TW201800496AD00032
In Chemical Formula 8, R x is a substituted or unsubstituted C1 to C10 alkyl group, and z is an integer ranging from 0 to 5.

舉例來說,經取代或未經取代的醯基可由化學式9表示。 [化學式9]

Figure TW201800496AD00033
For example, a substituted or unsubstituted fluorenyl group can be represented by Chemical Formula 9. [Chemical Formula 9]
Figure TW201800496AD00033

舉例來說,R6 可為叔丁基、由化學式8表示的取代基、或由化學式9表示的取代基。For example, R 6 may be a tert-butyl group, a substituent represented by Chemical Formula 8, or a substituent represented by Chemical Formula 9.

舉例來說,R7 至R9 可獨立地為羥基或叔丁基,其限制條件是R7 及R8 中的至少一者為羥基。For example, R 7 to R 9 may independently be a hydroxyl group or a t-butyl group, with the proviso that at least one of R 7 and R 8 is a hydroxyl group.

舉例來說,R10 可為經取代或未經取代的甲基、經取代或未經取代的乙基、經取代或未經取代的丙基、經取代或未經取代的丁基、或者經取代或未經取代的戊基。For example, R 10 may be substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, or Substituted or unsubstituted pentyl.

在化學式1中,R1 的位置可為鄰位、間位、或對位。舉例來說,R1 的位置可為鄰位或對位,例如為鄰位。當R1 按照次序變成間位、對位、及鄰位時,亮度及耐熱性可按照所述次序為優異的。換句話說,在對位具有R1 的化合物可具有比在間位具有R1 的化合物更優異的亮度及耐熱性,且在鄰位具有R1 的化合物可具有比在對位具有R1的化合物更優異的亮度及耐熱性。In Chemical Formula 1, the position of R 1 may be an ortho, meta, or para position. For example, the position of R 1 can be an ortho or para position, such as an ortho position. When R 1 becomes meta, para, and ortho, in order, the brightness and heat resistance can be excellent in the order described. In other words, a compound having in the para position of R 1 can have more excellent than the compound of R 1 has the brightness in the meta and heat resistance, and the compound having a ratio R1 of the compound may have for R 1 in the ortho position with More excellent brightness and heat resistance.

舉例來說,由化學式1表示的化合物可為由化學式10-1表示的化合物或由化學式10-2表示的化合物。 [化學式10-1]

Figure TW201800496AD00034
[化學式10-2]
Figure TW201800496AD00035
在化學式10-1及化學式10-2中, R1 為鹵素原子、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基, R2 為經取代或未經取代的C3至C20脂環族環狀基、或者經取代或未經取代的C6至C20芳基,其限制條件是所述芳基具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基, R3 至R5 獨立地為經取代或未經取代的C1至C20烷基,且 L由化學式2表示, [化學式2]
Figure TW201800496AD00036
其中,在化學式2中, L1 為-O(C=O)-,且 A為經取代或未經取代的C1至C20烷基、經取代或未經取代的C3至C20脂環族環狀基、或者經取代或未經取代的C6至C20芳基。For example, the compound represented by Chemical Formula 1 may be a compound represented by Chemical Formula 10-1 or a compound represented by Chemical Formula 10-2. [Chemical Formula 10-1]
Figure TW201800496AD00034
[Chemical Formula 10-2]
Figure TW201800496AD00035
In Chemical Formula 10-1 and Chemical Formula 10-2, R 1 is a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group, and R 2 is a a substituted or unsubstituted C3 to C20 alicyclic cyclic group, or a substituted or unsubstituted C6 to C20 aryl group, with the proviso that the aryl group has at least one selected from a halogen atom, substituted or not a substituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 alkylthio group, and R 3 to R 5 are independently a substituted or unsubstituted C1 to C20 alkyl group, and L is represented by Chemical Formula 2, [Chemical Formula 2]
Figure TW201800496AD00036
Wherein, in Chemical Formula 2, L 1 is -O(C=O)-, and A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring. A substituted or unsubstituted C6 to C20 aryl group.

由化學式1表示的化合物可由選自化學式1-1至化學式1-12中的一者表示。 [化學式1-1]

Figure TW201800496AD00037
[化學式1-2]
Figure TW201800496AD00038
[化學式1-3]
Figure TW201800496AD00039
[化學式1-4]
Figure TW201800496AD00040
[化學式1-5]
Figure TW201800496AD00041
[化學式1-6]
Figure TW201800496AD00042
[化學式1-7]
Figure TW201800496AD00043
[化學式1-8]
Figure TW201800496AD00044
[化學式1-9]
Figure TW201800496AD00045
[化學式1-10]
Figure TW201800496AD00046
[化學式1-11]
Figure TW201800496AD00047
[化學式1-12]
Figure TW201800496AD00048
The compound represented by Chemical Formula 1 can be represented by one selected from Chemical Formula 1-1 to Chemical Formula 1-12. [Chemical Formula 1-1]
Figure TW201800496AD00037
[Chemical Formula 1-2]
Figure TW201800496AD00038
[Chemical Formula 1-3]
Figure TW201800496AD00039
[Chemical Formula 1-4]
Figure TW201800496AD00040
[Chemical Formula 1-5]
Figure TW201800496AD00041
[Chemical Formula 1-6]
Figure TW201800496AD00042
[Chemical Formula 1-7]
Figure TW201800496AD00043
[Chemical Formula 1-8]
Figure TW201800496AD00044
[Chemical Formula 1-9]
Figure TW201800496AD00045
[Chemical Formula 1-10]
Figure TW201800496AD00046
[Chemical Formula 1-11]
Figure TW201800496AD00047
[Chemical Formula 1-12]
Figure TW201800496AD00048

根據實施例的由化學式1表示的化合物即使為少量情況下仍可表達清晰的色彩,且當用作著色劑時,可製造出具有例如亮度、對比度等優異的色彩特性的顯示器裝置。舉例來說,所述化合物可為著色劑,例如染料,例如藍色或紫色染料,例如在300 nm至600 nm、例如450 nm至600 nm的波長範圍內具有最大吸光度的染料。The compound represented by Chemical Formula 1 according to the embodiment can express a clear color even in a small amount, and when used as a coloring agent, a display device having excellent color characteristics such as brightness, contrast, and the like can be manufactured. For example, the compound can be a colorant, such as a dye, such as a blue or violet dye, such as a dye having a maximum absorbance in the wavelength range from 300 nm to 600 nm, such as from 450 nm to 600 nm.

一般來說,染料為彩色濾光片中所使用的成分中最昂貴的。因此,可能需要昂貴的染料更多地用於實現所期望的效果(例如高亮度、高對比等),且因此,會增加生產的單位成本。然而,當根據實施例的化合物用作著色劑(例如彩色濾光片中的染料)時,所述化合物及/或聚合物即使少量地使用仍可實現改善的色彩特性(例如高亮度或高對比),並降低生產的單位成本。In general, dyes are the most expensive of the components used in color filters. Therefore, expensive dyes may be required to be used more to achieve desired effects (e.g., high brightness, high contrast, etc.) and, therefore, increase the unit cost of production. However, when the compound according to the embodiment is used as a colorant (for example, a dye in a color filter), the compound and/or polymer can achieve improved color characteristics even when used in a small amount (for example, high brightness or high contrast) ) and reduce the unit cost of production.

根據另一實施例,提供一種包含根據實施例的化合物作為染料的感光性樹脂組成物。According to another embodiment, there is provided a photosensitive resin composition comprising the compound according to the embodiment as a dye.

舉例來說,以根據實施例的感光性樹脂組成物的總量計,所述感光性樹脂組成物包含5重量%至20重量%、例如10重量%至15重量%的量的由化學式1表示的化合物,且因此亮度、耐熱性、及耐化學性可顯著改善。即,以感光性樹脂組成物的總量計,可包含5重量%至20重量%、例如10重量%至15重量%的量的染料,且因此亮度、耐熱性、及耐化學性得以改善。For example, the photosensitive resin composition contains the amount of 5% by weight to 20% by weight, for example, 10% by weight to 15% by weight, based on the total amount of the photosensitive resin composition of the embodiment, represented by Chemical Formula 1. The compound, and thus the brightness, heat resistance, and chemical resistance, can be significantly improved. That is, the dye may be contained in an amount of 5 wt% to 20 wt%, for example, 10 wt% to 15 wt%, based on the total amount of the photosensitive resin composition, and thus brightness, heat resistance, and chemical resistance are improved.

舉例來說,所述感光性樹脂組成物可包含根據實施例的化合物、顏料、黏合劑樹脂、光可聚合單體、光聚合引發劑、及溶劑。For example, the photosensitive resin composition may include a compound, a pigment, a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent according to the examples.

根據實施例的化合物可在感光性樹脂組成物中充當著色劑(例如,染料,例如藍色染料或紫色染料),且因此可實現優異的色彩特性。The compound according to the embodiment can function as a colorant (for example, a dye such as a blue dye or a violet dye) in the photosensitive resin composition, and thus excellent color characteristics can be achieved.

顏料可包括黃色顏料、綠色顏料、紅色顏料、藍色顏料、紫色顏料、或其組合,但並非僅限於此。舉例來說,顏料可以顏料分散液的形式包含在感光性樹脂組成物中。The pigment may include, but is not limited to, a yellow pigment, a green pigment, a red pigment, a blue pigment, a violet pigment, or a combination thereof. For example, the pigment may be contained in the photosensitive resin composition in the form of a pigment dispersion.

顏料分散液可包含固體顏料、溶劑、及將顏料均勻地分散在溶劑中的分散劑。The pigment dispersion may contain a solid pigment, a solvent, and a dispersant that uniformly disperses the pigment in a solvent.

以顏料分散液的總量計,可包含1重量%至20重量%、例如8重量%至20重量%、例如15重量%至20重量%、例如8重量%至15重量%、例如10重量%至20重量%或例如10重量%至15重量%的量的固體顏料。It may comprise from 1% by weight to 20% by weight, for example from 8% by weight to 20% by weight, for example from 15% by weight to 20% by weight, for example from 8% by weight to 15% by weight, for example 10% by weight, based on the total mass of the pigment dispersion A solid pigment in an amount of up to 20% by weight or such as from 10% to 15% by weight.

分散劑可為非離子分散劑、陰離子分散劑、陽離子分散劑等。分散劑的具體實例可為聚伸烷基二醇及其酯、聚氧化烯、多元醇酯環氧烷加成產物、醇環氧烷加成產物、磺酸酯、磺酸鹽、羧酸酯、羧酸鹽、烷基醯胺環氧烷加成產物、烷基胺等,且這些分散劑可單獨使用或作為兩者或更多者的混合物形式使用。The dispersant may be a nonionic dispersant, an anionic dispersant, a cationic dispersant or the like. Specific examples of the dispersing agent may be a polyalkylene glycol and an ester thereof, a polyoxyalkylene, a polyhydric alcohol ester alkylene oxide addition product, an alcohol alkylene oxide addition product, a sulfonate, a sulfonate, a carboxylate A carboxylate, an alkylguanamine alkylene oxide addition product, an alkylamine or the like, and these dispersants may be used singly or as a mixture of two or more.

分散劑的市售實例可包括畢克化學有限公司(BYK Co., Ltd.)製成的迪斯帕畢克(DISPERBYK)-101、DISPERBYK-130、DISPERBYK-140、DISPERBYK-160、DISPERBYK-161、DISPERBYK-162、DISPERBYK-163、DISPERBYK-164、DISPERBYK-165、DISPERBYK-166、DISPERBYK-170、DISPERBYK-171、DISPERBYK-182、DISPERBYK-2000、DISPERBYK-2001;埃夫卡化學公司(EFKA Chemicals Co.)製造的埃夫卡(EFKA)-47、EFKA-47EA、EFKA-48、EFKA-49、EFKA-100、EFKA-400、EFKA-450;捷利康(Zeneka)公司製造的索思帕(Solsperse)5000、Solsperse 12000、Solsperse 13240、Solsperse 13940、Solsperse 17000、Solsperse 20000、Solsperse 24000GR、Solsperse 27000、Solsperse 28000等;或味之素公司(Ajinomoto Inc.)製造的PB711、PB821等。Commercially available examples of dispersants may include DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161 made by BYK Co., Ltd. , DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK-166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001; EFKA Chemicals Co .) manufactured Efka (EFKA)-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450; Solsperse manufactured by Zeneka 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, etc.; or PB711, PB821, etc. manufactured by Ajinomoto Inc.

以顏料分散液的總量計,可包含1重量%至20重量%的量的分散劑。當包含處於所述範圍內的分散劑時,感光性樹脂組成物的分散性因適當的黏度而得以改善,且因此當將感光性樹脂組成物應用於產品時可維持光學品質、物理品質、及化學品質。The dispersant may be included in an amount of from 1% by weight to 20% by weight based on the total amount of the pigment dispersion. When the dispersant in the above range is contained, the dispersibility of the photosensitive resin composition is improved by an appropriate viscosity, and thus the optical quality, physical quality, and the like can be maintained when the photosensitive resin composition is applied to a product. Chemical quality.

用於形成顏料分散液的溶劑可為乙二醇乙酸酯、乙基溶纖劑、丙二醇單甲醚乙酸酯、乳酸乙酯、聚乙二醇、環己酮、丙二醇甲基醚等。The solvent used to form the pigment dispersion may be ethylene glycol acetate, ethyl cellosolve, propylene glycol monomethyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether or the like.

以感光性樹脂組成物的總量計,可包含40重量%至60重量%、例如45重量%至55重量%的量的顏料分散液。當包含處於所述範圍內的顏料分散液時,可確保製程裕度(process margin),且色彩再現性及對比度得以改善。The pigment dispersion may be contained in an amount of 40% by weight to 60% by weight, for example, 45% by weight to 55% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion in the range is contained, process margin is ensured, and color reproducibility and contrast are improved.

顏料可使用水溶性無機鹽及潤濕劑預處理。當顏料經過預處理後,顏料的最初粒徑可變得更細。The pigment can be pretreated with a water soluble inorganic salt and a wetting agent. When the pigment is pretreated, the initial particle size of the pigment can become finer.

預處理可如下進行:揉捏水溶性無機鹽及潤濕劑與顏料,且然後過濾並洗滌揉捏後的顏料。The pretreatment can be carried out by kneading the water-soluble inorganic salt and the wetting agent and the pigment, and then filtering and washing the kneaded pigment.

揉捏可在40℃至100℃的溫度下執行,且可通過在用水等洗滌掉無機鹽後過濾顏料執行過濾及洗滌。Kneading can be carried out at a temperature of from 40 ° C to 100 ° C, and filtration and washing can be carried out by filtering the pigment after washing off the inorganic salt with water or the like.

水溶性無機鹽的實例可為氯化鈉、氯化鉀等,但並不僅限於此。潤濕劑可使顏料與水溶性無機鹽均勻地混合並粉碎。潤濕劑的實例包括伸烷基二醇單烷基醚(alkylene glycol monoalkyl ether),例如乙二醇單乙醚、丙二醇單甲醚、二乙二醇單甲醚等;以及醇,例如乙醇、異丙醇、丁醇、己醇、環己醇、乙二醇、二乙二醇、聚乙二醇、甘油聚乙二醇等。這些潤濕劑可單獨使用或作為兩者或更多者的混合物形式使用。Examples of the water-soluble inorganic salt may be sodium chloride, potassium chloride or the like, but are not limited thereto. The wetting agent uniformly mixes and pulverizes the pigment with the water-soluble inorganic salt. Examples of the wetting agent include an alkylene glycol monoalkyl ether such as ethylene glycol monoethyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, and the like; and an alcohol such as ethanol or the like. Propanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, polyethylene glycol, glycerol polyethylene glycol, and the like. These wetting agents may be used singly or as a mixture of two or more.

揉捏後的顏料可具有介於30 nm至約100 nm範圍的平均粒徑。當顏料的平均粒徑處於所述範圍內時,耐熱性及耐光性可得以改善,且可有效地形成精細圖案。The kneaded pigment may have an average particle size ranging from 30 nm to about 100 nm. When the average particle diameter of the pigment is within the range, heat resistance and light resistance can be improved, and a fine pattern can be efficiently formed.

感光性樹脂組成物包含含有染料及顏料的著色劑,且以感光性樹脂組成物的總量計,可包含45重量%至80重量%、例如55重量%至70重量%的量的著色劑。當包含處於所述範圍內的著色劑時,亮度、色彩再現性、圖案固化性、耐熱性、及耐化學性得以改善。The photosensitive resin composition contains a coloring agent containing a dye and a pigment, and may include a coloring agent in an amount of 45% by weight to 80% by weight, for example, 55% by weight to 70% by weight based on the total amount of the photosensitive resin composition. When the coloring agent within the range is included, brightness, color reproducibility, pattern curability, heat resistance, and chemical resistance are improved.

黏合劑樹脂可包括丙烯酸系黏合劑樹脂、卡多系黏合劑樹脂、或其組合。The binder resin may include an acrylic binder resin, a cardo binder resin, or a combination thereof.

丙烯酸系黏合劑樹脂為第一烯系不飽和單體及可與其共聚合的第二烯系不飽和單體的共聚物,並且是包含至少一個丙烯酸系重複單元的樹脂。The acrylic adhesive resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing at least one acrylic repeating unit.

第一烯系不飽和單體為包含至少一個羧基的烯系不飽和單體。所述單體的實例包含(甲基)丙烯酸、順丁烯二酸、衣康酸、反丁烯二酸或其組合。The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer comprising at least one carboxyl group. Examples of the monomer include (meth)acrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

以丙烯酸系黏合劑樹脂的總量計,可包含5重量%至50重量%、例如10重量%至40重量%的量的第一烯系不飽和單體。The first ethylenically unsaturated monomer may be included in an amount of from 5% by weight to 50% by weight, for example from 10% by weight to 40% by weight, based on the total of the acrylic binder resin.

第二烯系不飽和單體可為芳族乙烯基化合物,例如苯乙烯、α-甲基苯乙烯、乙烯基甲苯、乙烯基苯甲基甲醚等;不飽和羧酸酯化合物,例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸2-羥乙酯、(甲基)丙烯酸2-羥丁酯、(甲基)丙烯酸苯甲酯、(甲基)丙烯酸環己基酯、(甲基)丙烯酸苯酯等;不飽和氨基烷基羧酸酯化合物,例如(甲基)丙烯酸2-氨基乙酯、(甲基)丙烯酸2-二甲氨基乙酯等;羧酸乙烯基酯化合物,例如乙酸乙烯酯、苯甲酸乙烯酯等;不飽和縮水甘油基羧酸酯化合物,例如(甲基)丙烯酸縮水甘油基酯等;丙烯腈化合物,例如(甲基)丙烯腈等;不飽和醯胺化合物,例如(甲基)丙烯醯胺等;等等,且所述第二烯系不飽和單體可單獨使用或作為兩者或更多者的混合物形式使用。The diene unsaturated monomer may be an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene, vinylbenzyl methyl ether or the like; an unsaturated carboxylic acid ester compound such as (A) Methyl acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzene (meth) acrylate Methyl ester, cyclohexyl (meth) acrylate, phenyl (meth) acrylate, etc.; unsaturated aminoalkyl carboxylate compound, such as 2-aminoethyl (meth)acrylate, 2-(meth)acrylate Dimethylaminoethyl ester or the like; a vinyl carboxylate compound such as vinyl acetate, vinyl benzoate or the like; an unsaturated glycidyl carboxylate compound such as glycidyl (meth)acrylate; an acrylonitrile compound , for example, (meth)acrylonitrile or the like; an unsaturated decylamine compound such as (meth) acrylamide or the like; and the like, and the second ethylenically unsaturated monomer may be used singly or as two or more The mixture is used in the form of a mixture.

丙烯酸系黏合劑樹脂的具體實例可為聚甲基丙烯酸苯甲酯共聚物、(甲基)丙烯酸/甲基丙烯酸苯甲酯共聚物、(甲基)丙烯酸/甲基丙烯酸苯甲酯/苯乙烯共聚物、(甲基)丙烯酸/甲基丙烯酸苯甲酯/甲基丙烯酸2-羥乙酯共聚物、(甲基)丙烯酸/甲基丙烯酸苯甲酯/苯乙烯/甲基丙烯酸2-羥乙酯共聚物等,但並非僅限於此。這些丙烯酸系黏合劑樹脂可單獨使用或作為兩者或更多者的混合物形式使用。Specific examples of the acrylic adhesive resin may be polybenzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene Copolymer, (meth)acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, (meth)acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate Ester copolymers, etc., but are not limited thereto. These acrylic adhesive resins may be used singly or as a mixture of two or more.

丙烯酸系黏合劑樹脂的重量平均分子量可為3,000 g/mol至150,000 g/mol,例如5,000 g/mol至50,000 g/mol,或例如20,000 g/mol至30,000 g/mol。當丙烯酸系黏合劑樹脂的重量平均分子量在所述範圍內時,感光性樹脂組成物在彩色濾光片的製造期間具有良好的物理性質及化學性質、適當的黏度、以及與基板緊密接觸的性質。The acrylic binder resin may have a weight average molecular weight of from 3,000 g/mol to 150,000 g/mol, such as from 5,000 g/mol to 50,000 g/mol, or such as from 20,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the acrylic adhesive resin is within the above range, the photosensitive resin composition has good physical properties and chemical properties, proper viscosity, and close contact with the substrate during the manufacture of the color filter. .

丙烯酸系黏合劑樹脂的酸值可為15 mgKOH/g至60 mgKOH/g,例如20 mgKOH/g至50 mgKOH/g。當丙烯酸系黏合劑樹脂的酸值在所述範圍內時,像素圖案的解析度得以提高。The acrylic binder resin may have an acid value of from 15 mgKOH/g to 60 mgKOH/g, for example from 20 mgKOH/g to 50 mgKOH/g. When the acid value of the acrylic adhesive resin is within the above range, the resolution of the pixel pattern is improved.

卡多系黏合劑樹脂可包含由化學式11表示的重複單元。 [化學式11]

Figure TW201800496AD00049
在化學式11中, R11 及R12 獨立地為氫原子或者經取代或未經取代的(甲基)丙烯醯氧基烷基, R13 及R14 獨立地為氫原子、鹵素原子、或者經取代或未經取代的C1至C20烷基,且 Z1 為單鍵、O、CO、SO2 、CR15 R16 、SiR17 R18 (其中,R15 至R18 獨立地為氫原子或者經取代或未經取代的C1至C20烷基)、或由化學式11-1至化學式11-11表示的連接基中的一者, [化學式11-1]
Figure TW201800496AD00050
[化學式11-2]
Figure TW201800496AD00051
[化學式11-3]
Figure TW201800496AD00052
[化學式11-4]
Figure TW201800496AD00053
[化學式11-5]
Figure TW201800496AD00054
(在化學式11-5中,Ra 為氫原子、乙基、C2 H4 Cl、C2 H4 OH、CH2 CH=CH2 、或苯基) [化學式11-6]
Figure TW201800496AD00055
[化學式11-7]
Figure TW201800496AD00056
[化學式11-8]
Figure TW201800496AD00057
[化學式11-9]
Figure TW201800496AD00058
[化學式11-10]
Figure TW201800496AD00059
[化學式11-11]
Figure TW201800496AD00060
Z2 為酸二酐殘基,且 m1及m2獨立地為介於0至4範圍內的整數。The card multi-adhesive resin may contain a repeating unit represented by Chemical Formula 11. [Chemical Formula 11]
Figure TW201800496AD00049
In Chemical Formula 11, R 11 and R 12 are independently a hydrogen atom or a substituted or unsubstituted (meth) acryloxyalkyl group, and R 13 and R 14 are independently a hydrogen atom, a halogen atom, or a a substituted or unsubstituted C1 to C20 alkyl group, and Z 1 is a single bond, O, CO, SO 2 , CR 15 R 16 , SiR 17 R 18 (wherein R 15 to R 18 are independently a hydrogen atom or a a substituted or unsubstituted C1 to C20 alkyl group, or one of the linking groups represented by Chemical Formula 11-1 to Chemical Formula 11-11, [Chemical Formula 11-1]
Figure TW201800496AD00050
[Chemical Formula 11-2]
Figure TW201800496AD00051
[Chemical Formula 11-3]
Figure TW201800496AD00052
[Chemical Formula 11-4]
Figure TW201800496AD00053
[Chemical Formula 11-5]
Figure TW201800496AD00054
(In Chemical Formula 11-5, R a is a hydrogen atom, an ethyl group, C 2 H 4 Cl, C 2 H 4 OH, CH 2 CH=CH 2 , or a phenyl group) [Chemical Formula 11-6]
Figure TW201800496AD00055
[Chemical Formula 11-7]
Figure TW201800496AD00056
[Chemical Formula 11-8]
Figure TW201800496AD00057
[Chemical Formula 11-9]
Figure TW201800496AD00058
[Chemical Formula 11-10]
Figure TW201800496AD00059
[Chemical Formula 11-11]
Figure TW201800496AD00060
Z 2 is an acid dianhydride residue, and m1 and m2 are independently an integer ranging from 0 to 4.

卡多系黏合劑樹脂的末端中的至少一者可包含由化學式12表示的官能基。 [化學式12]

Figure TW201800496AD00061
在化學式12中, Z3 由化學式12-1或化學式12-7表示。 [化學式12-1]
Figure TW201800496AD00062
(在化學式12-1中,Rb 及Rc 獨立地為氫原子、經取代或未經取代的C1至C20烷基、酯基、或醚基) [化學式12-2]
Figure TW201800496AD00063
[化學式12-3]
Figure TW201800496AD00064
[化學式12-4]
Figure TW201800496AD00065
[化學式12-5]
Figure TW201800496AD00066
(在化學式12-5中,Rd 為O、S、NH、經取代或未經取代的C1至C20伸烷基、C1至C20烷基胺基、或C2至C20烯基胺基) [化學式12-6]
Figure TW201800496AD00067
[化學式12-7]
Figure TW201800496AD00068
At least one of the ends of the cardo-based binder resin may include a functional group represented by Chemical Formula 12. [Chemical Formula 12]
Figure TW201800496AD00061
In Chemical Formula 12, Z 3 is represented by Chemical Formula 12-1 or Chemical Formula 12-7. [Chemical Formula 12-1]
Figure TW201800496AD00062
(In Chemical Formula 12-1, R b and R c are independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group, or an ether group) [Chemical Formula 12-2]
Figure TW201800496AD00063
[Chemical Formula 12-3]
Figure TW201800496AD00064
[Chemical Formula 12-4]
Figure TW201800496AD00065
[Chemical Formula 12-5]
Figure TW201800496AD00066
(In Chemical Formula 12-5, R d is O, S, NH, substituted or unsubstituted C1 to C20 alkylene group, C1 to C20 alkylamino group, or C2 to C20 alkenylamino group) [Chemical Formula 12-6]
Figure TW201800496AD00067
[Chemical Formula 12-7]
Figure TW201800496AD00068

卡多系黏合劑樹脂可例如通過混合下列中的至少兩者來製備:含芴化合物,例如9,9-雙(4-環氧乙烷基甲氧基苯基)芴(9,9-bis(4-oxiranylmethoxyphenyl)fluorene);酸酐化合物,例如苯四甲酸二酐、萘四甲酸二酐、聯苯四甲酸二酐、二苯甲酮四甲酸二酐、苯均四酸二酐、環丁烷四甲酸二酐、苝四甲酸二酐、四氫呋喃四甲酸二酐、及四氫鄰苯二甲酸酐;二醇化合物,例如乙二醇、丙二醇、及聚乙二醇;醇化合物,例如甲醇、乙醇、丙醇、正丁醇、環己醇、及苯甲醇;溶劑系化合物,例如丙二醇乙酸甲基乙酯及N-甲基吡咯烷酮;磷化合物,例如三苯基膦;以及胺或銨鹽化合物,例如四甲基氯化銨、四乙基溴化銨、苯甲基二乙胺、三乙胺、三丁胺、及苯甲基三乙基氯化銨。The cardo-based binder resin can be prepared, for example, by mixing at least two of the following: a ruthenium-containing compound such as 9,9-bis(4-oxiranylmethoxyphenyl)anthracene (9,9-bis) (4-oxiranylmethoxyphenyl)fluorene); an acid anhydride compound such as pyromellitic dianhydride, naphthalenetetracarboxylic dianhydride, biphenyltetracarboxylic dianhydride, benzophenone tetracarboxylic dianhydride, pyromellitic dianhydride, cyclobutane Tetracarboxylic acid dianhydride, perylenetetracarboxylic dianhydride, tetrahydrofuran tetracarboxylic dianhydride, and tetrahydrophthalic anhydride; glycol compounds such as ethylene glycol, propylene glycol, and polyethylene glycol; alcohol compounds such as methanol, ethanol , propanol, n-butanol, cyclohexanol, and benzyl alcohol; solvent-based compounds such as propylene glycol methyl ethyl acetate and N-methylpyrrolidone; phosphorus compounds such as triphenylphosphine; and amine or ammonium salt compounds, For example, tetramethylammonium chloride, tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, and benzyltriethylammonium chloride.

卡多系黏合劑樹脂具有低的可顯影性,當彩色濾光片由具有卡多系黏合劑樹脂的感光性樹脂組成物形成時,會難以控制圖案的可顯影性。本文中,可使用丙烯酸系黏合劑樹脂與卡多系黏合劑樹脂一起作為黏合劑樹脂來控制圖案的可顯影性。The card multi-adhesive resin has low developability, and when the color filter is formed of a photosensitive resin composition having a cardo-based adhesive resin, it is difficult to control the developability of the pattern. Herein, an acrylic adhesive resin can be used together with a card-based adhesive resin as a binder resin to control the developability of the pattern.

此外,當卡多系黏合劑樹脂與丙烯酸系黏合劑樹脂一起使用時,可獲得具有高解析度及高亮度特性、以及優異的緊密接觸力的感光性樹脂組成物。Further, when a cardo-based adhesive resin is used together with an acrylic-based adhesive resin, a photosensitive resin composition having high resolution and high brightness characteristics and excellent close contact force can be obtained.

卡多系黏合劑樹脂的重量平均分子量可為500 g/mol至50,000 g/mol,例如3,000 g/mol至30,000 g/mol。當卡多系黏合劑樹脂的重量平均分子量在所述範圍內時,在製造彩色濾光片期間可很好地形成圖案而無殘留,並且在顯影期間膜厚度不會減小。The card multi-adhesive resin may have a weight average molecular weight of from 500 g/mol to 50,000 g/mol, for example from 3,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the card multi-adhesive resin is within the range, a pattern can be well formed without residue during the production of the color filter, and the film thickness does not decrease during development.

卡多系黏合劑樹脂的酸值可為100 mgKOH/g至140 mgKOH/g。The cardo binder resin may have an acid value of from 100 mgKOH/g to 140 mgKOH/g.

以感光性樹脂組成物的總量計,可包含1重量%至10重量%、例如1重量%至5重量%的量的黏合劑樹脂。當包含處於所述範圍內的黏合劑樹脂時,可獲得優異的靈敏度、可顯影性、解析度、及圖案線性度。The binder resin may be contained in an amount of from 1% by weight to 10% by weight, for example, from 1% by weight to 5% by weight based on the total of the photosensitive resin composition. When the binder resin in the range is contained, excellent sensitivity, developability, resolution, and pattern linearity can be obtained.

光可聚合單體可為包含至少一個烯系不飽和雙鍵的(甲基)丙烯酸單官能或多官能酯。The photopolymerizable monomer may be a (meth)acrylic monofunctional or polyfunctional ester containing at least one ethylenically unsaturated double bond.

光可聚合單體具有烯系不飽和雙鍵,且因此,可在圖案形成過程的曝光期間引起足夠的聚合並形成具有優異的耐熱性、耐光性和耐化學性的圖案。The photopolymerizable monomer has an ethylenically unsaturated double bond, and thus, can cause sufficient polymerization during exposure of the pattern forming process and form a pattern having excellent heat resistance, light resistance, and chemical resistance.

光可聚合單體的具體實例可為乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、雙酚A二(甲基)丙烯酸酯、季戊四醇二(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、季異戊四醇六(甲基)丙烯酸酯、二季戊四醇二(甲基)丙烯酸酯、二季戊四醇三(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、雙酚A環氧基(甲基)丙烯酸酯、乙二醇單甲醚(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、磷酸三(甲基)丙烯醯氧基乙酯、酚醛環氧(甲基)丙烯酸酯等。Specific examples of the photopolymerizable monomer may be ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(methyl) Acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A (Meth) acrylate, pentaerythritol di(meth) acrylate, pentaerythritol tri(meth) acrylate, pentaerythritol tetra (meth) acrylate, quaternary pentoxide hexa (meth) acrylate, dipentaerythritol II (meth) acrylate, dipentaerythritol tri(meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, Ethylene glycol monomethyl ether (meth) acrylate, trimethylolpropane tri(meth) acrylate, tris(meth) propylene methoxyethyl phosphate, phenol aldehyde epoxy (meth) acrylate, and the like.

光可聚合單體的市售實例如下。單官能(甲基)丙烯酸酯可包含亞羅尼斯(Aronix)M-101® 、M-111® 、M-114® (東亞合成化工有限公司(Toagosei Chemistry Industry Co., Ltd.));卡亞拉得(KAYARAD)TC-110S® 、TC-120S® (日本化藥有限公司(Nippon Kayaku Co., Ltd.));V-158® 、V-2311® (大阪有機化工有限公司(Osaka Organic Chemical Ind., Ltd.))等。二官能(甲基)丙烯酸酯的實例可包含亞羅尼斯(Aronix)M-210® 、M-240® 、M-6200® (東亞化工有限公司)、卡亞拉得(KAYARAD)HDDA® 、HX-220® 、R-604® (日本化藥有限公司)、V-260® 、V-312® 、V-335 HP® (大阪有機化工有限公司)等。三官能(甲基)丙烯酸酯的實例可包含亞羅尼斯(Aronix)M-309® 、M-400® 、M-405® 、M-450® 、M-7100® 、M-8030® 、M-8060® (東亞化工有限公司)、卡亞拉得(KAYARAD)TMPTA® 、DPCA-20® 、DPCA-30® 、DPCA-60® 、DPCA-120® (日本化藥有限公司)、V-295® 、V-300® 、V-360® 、V-GPT® 、V-3PA® 、V-400® (大阪有機化工有限公司)等。這些光可聚合單體可單獨使用或作為兩者或更多者的混合物形式使用。Commercially available examples of photopolymerizable monomers are as follows. The monofunctional (meth) acrylate may comprise Aronix M-101 ® , M-111 ® , M-114 ® (Toagosei Chemistry Industry Co., Ltd.); Kaya KAYARAD TC-110S ® , TC-120S ® (Nippon Kayaku Co., Ltd.); V-158 ® , V-2311 ® (Osaka Organic Chemical Co., Ltd.) Ind., Ltd.)) and so on. Examples of the difunctional (meth) acrylate may include Aronix M-210 ® , M-240 ® , M-6200 ® (East Asia Chemical Co., Ltd.), KAYARAD HDDA ® , HX -220 ® , R-604 ® (Nippon Chemical Co., Ltd.), V-260 ® , V-312 ® , V-335 HP ® (Osaka Organic Chemical Co., Ltd.), etc. Examples of trifunctional (meth) acrylates may include Aronix M-309 ® , M-400 ® , M-405 ® , M-450 ® , M-7100 ® , M-8030 ® , M- 8060 ® (East Asia Chemical Co., Ltd.), KAYARAD TMPTA ® , DPCA-20 ® , DPCA-30 ® , DPCA-60 ® , DPCA-120 ® (Japan Chemicals Co., Ltd.), V-295 ® , V-300 ® , V-360 ® , V-GPT ® , V-3PA ® , V-400 ® (Osaka Organic Chemical Co., Ltd.), etc. These photopolymerizable monomers may be used singly or as a mixture of two or more.

光可聚合單體可用酸酐處理以改善可顯影性。The photopolymerizable monomer can be treated with an acid anhydride to improve developability.

以感光性樹脂組成物的總量計,可包含1重量%至5重量%、例如1重量%至3重量%的量的光可聚合單體。當包含處於所述範圍內的光可聚合單體時,光可聚合單體可在圖案形成過程期間進行曝光時充分固化且因此可靠性得以提高,並且通過鹼性顯影液進行顯影的可顯影性得以改善。The photopolymerizable monomer may be contained in an amount of from 1% by weight to 5% by weight, for example, from 1% by weight to 3% by weight based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer in the range is contained, the photopolymerizable monomer can be sufficiently cured upon exposure during the pattern forming process and thus reliability is improved, and developability by development with an alkaline developer Improved.

光聚合引發劑為感光性樹脂組成物中常用的引發劑,且可為例如苯乙酮系化合物、二苯甲酮系化合物、噻噸酮系化合物、安息香系化合物、三嗪系化合物、肟系化合物、或其組合。The photopolymerization initiator is a commonly used initiator in the photosensitive resin composition, and may be, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, or an anthraquinone-based compound. a compound, or a combination thereof.

苯乙酮系化合物的實例可為2,2'-二乙氧基苯乙酮、2,2'-二丁氧基苯乙酮、2-羥基-2-甲基苯丙酮、對叔丁基三氯苯乙酮、對叔丁基二氯苯乙酮、4-氯苯乙酮、2,2'-二氯-4-苯氧基苯乙酮、2-甲基-1-(4-(甲硫基)苯基)-2-嗎啉代丙-1-酮、2-苯甲基-2-二甲基氨基-1-(4-嗎啉苯基)-丁-1-酮等。Examples of the acetophenone-based compound may be 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, p-tert-butyl group. Trichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4- (Methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzylmethyl-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, etc. .

二苯甲酮系化合物的實例可為二苯甲酮、苯甲酸苯甲醯基酯、苯甲酸苯甲醯基甲酯、4-苯基二苯甲酮、羥基二苯甲酮、丙烯酸化二苯甲酮、4,4'-雙(二甲基氨基)二苯甲酮、4,4'-雙(二乙基氨基)二苯甲酮、4,4'-二甲基氨基二苯甲酮、4,4'-二氯二苯甲酮、3,3'-二甲基-2-甲氧基二苯甲酮等。Examples of the benzophenone-based compound may be benzophenone, benzhydryl benzoate, benzhydryl methyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated Benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobiphenyl Ketone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone and the like.

噻噸酮系化合物的實例可為噻噸酮、2-甲基噻噸酮、異丙基噻噸酮、2,4-二乙基噻噸酮、2,4-二異丙基噻噸酮、2-氯噻噸酮等。Examples of the thioxanthone-based compound may be thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone , 2-chlorothioxanthone and the like.

安息香系化合物的實例可為安息香、安息香甲醚、安息香乙醚、安息香異丙醚、安息香異丁醚、苯甲基二甲基縮酮等。Examples of the benzoin-based compound may be benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal or the like.

三嗪系化合物的實例可為2,4,6-三氯-s-三嗪、2-苯基4,6-雙(三氯甲基)-s-三嗪、2-(3',4'-二甲氧基苯乙烯基)-4,6-雙(三氯甲基)-s-三嗪、2- (4'-甲氧基萘基)-4,6-雙(三氯甲基)-s-三嗪、2-(對甲氧基苯基)-4,6-雙(三氯甲基)-s-三嗪、2-(對甲苯基)-4,6-雙(三氯甲基)-s-三嗪、2-聯苯基4,6-雙(三氯甲基)-s-三嗪、雙(三氯甲基)-6-苯乙烯基-s-三嗪、2-(萘醯1-基)-4,6-雙(三氯甲基)-s-三嗪、2-(4-甲氧基萘醯1-基)-4,6-雙(三氯甲基)-s-三嗪、2-4-雙(三氯甲基)-6-胡椒基-s-三嗪、2-4-雙(三氯甲基)-6- (4-甲氧基苯乙烯基)-s-三嗪等。Examples of the triazine-based compound may be 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis(trichloromethyl)-s-triazine, 2-(3',4 '-Dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethane) -s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis ( Trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-three Pyrazine, 2-(naphthoquinone-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphthoquinone-1-yl)-4,6-bis ( Trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperidinyl-s-triazine, 2-4-bis(trichloromethyl)-6- (4- Methoxystyryl)-s-triazine and the like.

肟系化合物的實例可為O-醯基肟系化合物、2-(鄰苯甲醯基肟)-1-[4-(苯硫基)苯基]-1,2-辛二酮、1-(鄰乙醯基肟)-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-哢唑-3-基]乙酮、O-乙氧羰基-α-氧氨基-1-苯基丙-1-酮等。O-醯基肟系化合物的實例可為1,2-辛二酮、2-二甲基氨基-2-(4-甲基苯甲基)-1-(4-嗎啉-4-基-苯基)-丁-1-酮、1-(4-苯硫基苯基)-丁-1,2-二酮2-肟-O-苯甲酸酯、1-(4-苯硫基苯基)-辛-1,2-二酮2-肟-O-苯甲酸酯、1-(4-苯硫基苯基)-辛-1-酮肟-O-乙酸酯、及1-(4-苯硫基苯基)-丁-1-酮肟-O-乙酸酯。Examples of the lanthanoid compound may be an O-indenyl lanthanide compound, 2-(o-benzylidene fluorenyl)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1- (o-Ethyl hydrazide)-1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxygen Amino-1-phenylpropan-1-one and the like. An example of the O-mercapto lanthanide compound may be 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl- Phenyl)-butan-1-one, 1-(4-phenylthiophenyl)-butan-1,2-dione 2-indole-O-benzoate, 1-(4-phenylthiobenzene Base)-octane-1,2-dione 2-indole-O-benzoate, 1-(4-phenylthiophenyl)-oct-1-one oxime-O-acetate, and 1- (4-Benzylthiophenyl)-butan-1-one oxime-O-acetate.

除所述化合物之外,光聚合引發劑可進一步包含哢唑系化合物、二酮系化合物、硼酸鋶系化合物、重氮系化合物、咪唑系化合物、聯咪唑系化合物、芴系化合物等。In addition to the above-mentioned compound, the photopolymerization initiator may further contain an oxazole compound, a diketone compound, a lanthanum borate compound, a diazo compound, an imidazole compound, a biimidazole compound, an anthraquinone compound, and the like.

光聚合引發劑可與能夠通過吸收光且被激發並隨後傳輸其能量而引起化學反應的光敏劑一起使用。The photopolymerization initiator can be used together with a photosensitizer capable of causing a chemical reaction by absorbing light and being excited and then transmitting its energy.

光敏劑的實例可為四乙二醇雙-3-巰基丙酸酯、季戊四醇四-3-巰基丙酸酯、二季戊四醇四-3-巰基丙酸酯等。Examples of the photosensitizer may be tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-mercaptopropionate, dipentaerythritol tetrakis-mercaptopropionate or the like.

以感光性樹脂組成物的總量計,可包含0.1重量%至3重量%、例如0.1重量%至2重量%的量的光聚合引發劑。當包含處於所述範圍內的光聚合引發劑時,由於在圖案形成過程的曝光期間進行充分固化,因此可確保優異的可靠性,且可防止透射率因非反應引發劑而劣化。The photopolymerization initiator may be contained in an amount of 0.1% by weight to 3% by weight, for example, 0.1% by weight to 2% by weight based on the total amount of the photosensitive resin composition. When the photopolymerization initiator in the range is contained, since sufficient curing is performed during the exposure of the pattern forming process, excellent reliability can be ensured, and the transmittance can be prevented from being deteriorated by the non-reactive initiator.

溶劑為具有與根據實施例的化合物、顏料、黏合劑樹脂、光可聚合單體、及光聚合引發劑的相容性但不與其反應的材料。The solvent is a material having compatibility with, but not reacting with, the compound according to the examples, the pigment, the binder resin, the photopolymerizable monomer, and the photopolymerization initiator.

溶劑的實例可包含醇,例如甲醇、乙醇等;醚,例如二氯乙醚、正丁醚、二異戊醚、苯甲醚、四氫呋喃等;二醇醚,例如乙二醇單甲醚、乙二醇單乙醚等;乙酸溶纖劑,例如乙酸甲基溶纖劑、乙酸乙基溶纖劑、乙酸二乙基溶纖劑等;卡必醇,例如甲基乙基卡必醇、二乙基卡必醇、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇二甲醚、二乙二醇甲乙醚、二乙二醇二乙醚等;丙二醇烷基醚乙酸酯,例如丙二醇甲基醚乙酸酯、丙二醇丙基醚乙酸酯等;芳族烴,例如甲苯、二甲苯等;酮,例如甲乙酮、環己酮、4-羥基-4-甲基-2-戊酮、甲基-正丙基酮、甲基-正丁基酮、甲基-正戊基酮、2-庚酮等;飽和脂肪族單羧酸烷基酯,例如乙酸乙酯、乙酸正丁酯、乙酸異丁酯等;乳酸酯,例如乳酸甲酯、乳酸乙酯等;氧基乙酸烷基酯,例如氧基乙酸甲酯、氧基乙酸乙酯、氧基乙酸丁酯等;烷氧基乙酸烷基酯,例如甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯等;3-氧基丙酸烷基酯,例如3-氧基丙酸甲酯、3-氧基丙酸乙酯等;3-烷氧基丙酸烷基酯,例如3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸甲酯等;2-氧基丙酸烷基酯,例如2-氧基丙酸甲酯、2-氧基丙酸乙酯、2-氧基丙酸丙酯等;2-烷氧基丙酸烷基酯,例如2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-乙氧基丙酸乙酯、2-乙氧基丙酸甲酯等;2-氧基-2-甲基丙酸酯,例如2-氧基-2-甲基丙酸甲酯、2-氧基-2-甲基丙酸乙酯等;2-烷氧基-2-甲基丙酸烷基酯的單氧基單羧酸烷基酯,例如2-甲氧基-2-甲基丙酸甲酯、2-乙氧基-2-甲基丙酸乙酯等;酯,例如2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁酸甲酯等;酮酸酯,例如丙酮酸乙酯等。另外,還可使用高沸點溶劑,例如N-甲基甲醯胺、N,N-二甲基甲醯胺、N-甲基甲醯苯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、N-甲基吡咯烷酮、二甲亞碸、苯甲基乙基醚、二己醚、乙醯丙酮、異佛爾酮、己酸、辛酸、1-辛醇、1-壬醇、苯甲醇、乙酸苯甲酯、苯甲酸乙酯、乙二酸二乙酯、順丁烯二酸二乙酯、γ-丁內酯、碳酸乙二酯、碳酸丙二酯、乙酸苯基溶纖劑等。Examples of the solvent may include an alcohol such as methanol, ethanol, etc.; an ether such as dichloroethyl ether, n-butyl ether, diisoamyl ether, anisole, tetrahydrofuran or the like; a glycol ether such as ethylene glycol monomethyl ether or ethylene Alcohol monoethyl ether, etc.; cellosolve acetate, such as methyl cellosolve acetate, ethyl cellosolve acetate, diethyl cellosolve acetate, etc.; carbitol, such as methyl ethyl carbitol, diethyl Carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, etc.; propylene glycol alkyl ether acetate, For example, propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentyl Ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-pentyl ketone, 2-heptanone, etc.; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate Ester, isobutyl acetate, etc.; lactate, such as methyl lactate, ethyl lactate, etc.; alkyl oxyacetate, such as methyl oxyacetate, ethyl oxyacetate, oxygen Butyl acetate and the like; alkyl alkoxyacetate, such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, etc. An alkyl 3-oxopropionate such as methyl 3-oxypropionate, ethyl 3-oxypropionate or the like; an alkyl 3-alkoxypropionate such as 3-methoxypropionic acid Methyl ester, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, etc.; alkyl 2-oxopropionate, such as 2-oxypropane Methyl ester, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.; alkyl 2-alkoxypropionate, such as methyl 2-methoxypropionate, 2-methoxy Ethyl propionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc.; 2-oxy-2-methylpropionate, such as 2-oxy-2-methylpropane Methyl ester, ethyl 2-oxy-2-methylpropionate, etc.; alkyl monooxymonocarboxylate of alkyl 2-alkoxy-2-methylpropanoate, such as 2-methoxy Methyl 2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc.; esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate , ethyl hydroxyacetate, 2-hydroxy-3-methyl Methyl butyrate or the like; a keto ester such as ethyl pyruvate. In addition, high boiling solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformamide, N-methylacetamide, N,N-di can also be used. Methylacetamide, N-methylpyrrolidone, dimethyl hydrazine, benzyl ethyl ether, dihexyl ether, acetamidine, isophorone, caproic acid, octanoic acid, 1-octanol, 1-indole Alcohol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl acetate Cellulolytic agent, etc.

考慮到混溶性及反應性,可優選地使用二醇醚,例如乙二醇單乙醚等;乙二醇烷基醚乙酸酯,例如乙酸乙基溶纖劑等;酯,例如2-羥基丙酸乙酯等;卡必醇,例如二乙二醇單甲醚等;以及丙二醇烷基醚乙酸酯,例如丙二醇甲基醚乙酸酯、丙二醇丙基醚乙酸酯等。In view of miscibility and reactivity, a glycol ether such as ethylene glycol monoethyl ether or the like; ethylene glycol alkyl ether acetate such as ethyl cellosolve acetate; and the like; an ester such as 2-hydroxypropyl may be preferably used. Ethyl acetate or the like; carbitol, such as diethylene glycol monomethyl ether; and propylene glycol alkyl ether acetate, such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate, and the like.

以感光性樹脂組成物的總量計,可包含餘量(例如15重量%至50重量%、或例如20重量%至40重量%)的溶劑。當包含處於所述範圍內的溶劑時,感光性樹脂組成物可具有適當的黏度,且因此當應用於產品時能改善塗層可加工性。The solvent may be included in the balance (for example, 15% by weight to 50% by weight, or for example, 20% by weight to 40% by weight) based on the total amount of the photosensitive resin composition. When a solvent in the range is contained, the photosensitive resin composition may have an appropriate viscosity, and thus the coating processability can be improved when applied to a product.

根據實施例的感光性樹脂組成物可進一步包含以下其他添加劑以防止在塗布期間產生污點或斑點、調整流平特性、或防止因未被顯影而引起圖案殘留:例如丙二酸;3-氨基-1,2-丙二醇;矽烷系偶合劑;流平劑;氟系表面活性劑;自由基聚合引發劑;或其組合等。The photosensitive resin composition according to the embodiment may further contain other additives to prevent generation of stains or spots during coating, to adjust leveling characteristics, or to prevent pattern residue due to undeveloped: for example, malonic acid; 3-amino- 1,2-propanediol; a decane-based coupling agent; a leveling agent; a fluorine-based surfactant; a radical polymerization initiator; or a combination thereof.

矽烷系偶合劑的實例可為三甲氧基矽烷基苯甲酸、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、乙烯基三乙醯氧基矽烷、乙烯基三甲氧基矽烷、γ-異氰酸酯基丙基三乙氧基矽烷、γ-縮水甘油氧基丙基三甲氧基矽烷、β-(3,4-環氧環己基)乙基三甲氧基矽烷等,且所述矽烷系偶合劑可單獨或以兩者或更多者的混合物形式使用。Examples of the decane coupling agent may be trimethoxydecyl benzoic acid, γ-methyl propylene methoxy propyl trimethoxy decane, vinyl triethoxy decane, vinyl trimethoxy decane, γ-isocyanate. Propyl triethoxy decane, γ-glycidoxypropyl trimethoxy decane, β-(3,4-epoxycyclohexyl)ethyltrimethoxy decane, etc., and the decane coupling agent can be used Used alone or in a mixture of two or more.

氟系表面活性劑的實例可為以下市售氟系表面活性劑:例如BM-1000® 及BM-1100® (BM化學公司(BM Chemie Inc.));MEGAFACE F 142D® 、F 172® 、F 173® 及F 183® (大日本油墨化學工業有限公司(Dainippon Ink Kagaku Kogyo Co., Ltd.));FULORAD FC-135® 、FULORAD FC-170C® 、FULORAD FC-430® 及FULORAD FC-431® (住友3M有限公司(Sumitomo 3M Co., Ltd.));SURFLON S-112® 、SURFLON S-113® 、SURFLON S-131® 、SURFLON S-141® 及SURFLON S-145® (旭硝子有限公司(Asahi Glass Co., Ltd.));以及SH-28PA® 、SH-190® 、SH-193® 、SZ-6032® 及SF-8428® 等(東麗矽有限公司(Toray Silicone Co., Ltd.))。Examples of the fluorine-based surfactant may be the following commercially available fluorine-based surfactants: for example, BM-1000 ® and BM-1100 ® (BM Chemie Inc.); MEGAFACE F 142D ® , F 172 ® , F 173 ® and F 183 ® (Dainippon Ink Kagaku Kogyo Co., Ltd.); FULORAD FC-135 ® , FULORAD FC-170C ® , FULORAD FC-430 ® and FULORAD FC-431 ® (Sumitomo 3M Co., Ltd.); SURFLON S-112 ® , SURFLON S-113 ® , SURFLON S-131 ® , SURFLON S-141 ® and SURFLON S-145 ® (Asahi Glass Co., Ltd. ( Asahi Glass Co., Ltd.); and SH-28PA ® , SH-190 ® , SH-193 ® , SZ-6032 ® and SF-8428 ® (Toray Silicone Co., Ltd.) )).

這些添加劑的量可根據所期望性質來調整。The amount of these additives can be adjusted depending on the desired properties.

所述感光性樹脂組成物可進一步包含環氧化合物以改善與基板的緊密接觸性質。The photosensitive resin composition may further contain an epoxy compound to improve the close contact property with the substrate.

所述環氧化合物可包含苯酚酚醛環氧化合物、四甲基聯苯基環氧化合物、雙酚A環氧化合物、脂環族環氧化合物或其組合。The epoxy compound may comprise a phenol novolac epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol A epoxy compound, an alicyclic epoxy compound, or a combination thereof.

此外,除非其他添加劑使感光性樹脂組成物的性質劣化,否則感光性樹脂組成物可包含預定量的其它添加劑,例如抗氧化劑、穩定劑等。Further, the photosensitive resin composition may contain a predetermined amount of other additives such as an antioxidant, a stabilizer, or the like, unless other additives deteriorate the properties of the photosensitive resin composition.

根據另一實施例,提供一種彩色濾光片,所述彩色濾光片包括使用根據所述實施例的感光性樹脂組成物製造的感光性樹脂膜。According to another embodiment, there is provided a color filter including a photosensitive resin film manufactured using the photosensitive resin composition according to the embodiment.

彩色濾光片的圖案形成過程如下。The pattern forming process of the color filter is as follows.

所述過程包括:以旋塗、狹縫塗布、噴墨印刷等的方法將正型感光性樹脂組成物塗布在支撐基板上;乾燥所塗布的正型感光性樹脂組成物以形成感光性樹脂組成物膜;使正型感光性樹脂組成物膜曝光;使所曝光的正型感光性樹脂組成物膜在鹼性水溶液中顯影以獲得感光性樹脂膜;以及對感光性樹脂膜進行熱處理。圖案化過程的條件為相關領域中所熟知的且將不在本說明書中詳細說明。The process includes: applying a positive photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing, or the like; drying the applied positive photosensitive resin composition to form a photosensitive resin composition The film is exposed; the positive photosensitive resin composition film is exposed; the exposed positive photosensitive resin composition film is developed in an alkaline aqueous solution to obtain a photosensitive resin film; and the photosensitive resin film is heat-treated. The conditions of the patterning process are well known in the relevant art and will not be described in detail in this specification.

在下文中,參考實例更詳細地說明本發明,然而,這些實例在任何意義上均不應解釋為限制本發明的範圍。In the following, the present invention will be described in more detail with reference to examples, however, these examples should not be construed as limiting the scope of the invention in any way.

(化合物的合成)(synthesis of compounds)

合成例1-1:由化學式2-1表示的化合物的合成

Figure TW201800496AD00069
向二甲基甲醯胺(dimethyl formamide,DMF,250 ml)中添加了2-溴-2-甲氧基苯乙酮(1 mol)並與此同時在室溫下進行了攪拌。向反應溶液中添加了鄰苯二甲醯亞胺鉀(0.95 mol),且將混合物攪拌了3小時。當反應完成之後,使用水(2500 ml)獲得了沉澱物,並然後進行了過濾及乾燥以獲得由化學式2-1表示的化合物。(產率:78%)Synthesis Example 1-1: Synthesis of a compound represented by Chemical Formula 2-1
Figure TW201800496AD00069
2-Bromo-2-methoxyacetophenone (1 mol) was added to dimethyl formamide (DMF, 250 ml) and stirred at room temperature. Potassium phthalimide (0.95 mol) was added to the reaction solution, and the mixture was stirred for 3 hours. After completion of the reaction, a precipitate was obtained using water (2500 ml), and then filtered and dried to obtain a compound represented by Chemical Formula 2-1. (Yield: 78%)

合成例1-2:由化學式2-2表示的化合物的合成 [化學式2-2]

Figure TW201800496AD00070
根據與合成例1-1相同的方法使用2-溴-4'-甲氧基苯乙酮作為起始材料合成了由化學式2-2表示的化合物。(產率:75.6 %)Synthesis Example 1-2: Synthesis of Compound represented by Chemical Formula 2-2 [Chemical Formula 2-2]
Figure TW201800496AD00070
The compound represented by Chemical Formula 2-2 was synthesized by the same method as in Synthesis Example 1-1 using 2-bromo-4'-methoxyacetophenone as a starting material. (Yield: 75.6 %)

合成例1-3:由化學式2-3表示的化合物的合成 [化學式2-3]

Figure TW201800496AD00071
根據與合成例1-1相同的方法使用2-溴-2'-氯苯乙酮作為起始材料合成了由化學式2-3表示的化合物。(產率:74.5 %)Synthesis Example 1-3: Synthesis of a compound represented by Chemical Formula 2-3 [Chemical Formula 2-3]
Figure TW201800496AD00071
The compound represented by Chemical Formula 2-3 was synthesized by the same method as in Synthesis Example 1-1 using 2-bromo-2'-chloroacetophenone as a starting material. (Yield: 74.5 %)

合成例1-4:由化學式2-4表示的化合物的合成 [化學式2-4]

Figure TW201800496AD00072
根據與合成例1-1相同的方法使用2-溴-4'-氯苯乙酮作為起始材料合成了由化學式2-4表示的化合物。(產率:78.4 %)Synthesis Example 1-4: Synthesis of a compound represented by Chemical Formula 2-4 [Chemical Formula 2-4]
Figure TW201800496AD00072
The compound represented by Chemical Formula 2-4 was synthesized by the same method as in Synthesis Example 1-1 using 2-bromo-4'-chloroacetophenone as a starting material. (Yield: 78.4%)

合成例1-5:由化學式2-5表示的化合物的合成 [化學式2-5]

Figure TW201800496AD00073
根據與合成例1-1相同的方法使用2-溴-4'-苯基苯乙酮作為起始材料合成了由化學式2-5表示的化合物。(產率:76.8 %)Synthesis Example 1-5: Synthesis of a compound represented by Chemical Formula 2-5 [Chemical Formula 2-5]
Figure TW201800496AD00073
The compound represented by Chemical Formula 2-5 was synthesized by the same method as in Synthesis Example 1-1 using 2-bromo-4'-phenylacetophenone as a starting material. (Yield: 76.8 %)

合成例1-6:由化學式2-6表示的化合物的合成 [化學式2-6]

Figure TW201800496AD00074
根據與合成例1-1相同的方法使用2-溴苯乙酮作為起始材料合成了由化學式2-6表示的化合物。(產率:81.5 %)Synthesis Example 1-6: Synthesis of a compound represented by Chemical Formula 2-6 [Chemical Formula 2-6]
Figure TW201800496AD00074
The compound represented by Chemical Formula 2-6 was synthesized by the same method as in Synthesis Example 1-1 using 2-bromoacetophenone as a starting material. (Yield: 81.5 %)

合成例2:由化學式3-1表示的化合物的合成

Figure TW201800496AD00075
向甲苯(500 ml)中添加了氰基乙酸(1.46 mol)及2,6-二-叔丁基-4-甲基環己醇(1.33 mol),且在室溫下對混合物進行了攪拌。向此反應溶液中添加了吡啶(1.59 mol)並與此同時進行了攪拌。向此溶液中添加了無水乙酸(2.65 mol)並與此同時攪拌了6小時以完成反應。將反應溶液用10%鹽酸水溶液(500 g)洗滌了兩次,並用氯化鈉水溶液(500 g)洗滌了兩次。使用硫酸鎂移除了水,且通過對其進行過濾及乾燥獲得了由化學式3-1表示的化合物。(產率:62.5 %)Synthesis Example 2: Synthesis of a compound represented by Chemical Formula 3-1
Figure TW201800496AD00075
Toluene (500 ml) was added with cyanoacetic acid (1.46 mol) and 2,6-di-tert-butyl-4-methylcyclohexanol (1.33 mol), and the mixture was stirred at room temperature. To the reaction solution, pyridine (1.59 mol) was added and stirred at the same time. Anhydrous acetic acid (2.65 mol) was added to this solution and stirred at the same time for 6 hours to complete the reaction. The reaction solution was washed twice with 10% aqueous hydrochloric acid (500 g) and twice with aqueous sodium chloride (500 g). Water was removed using magnesium sulfate, and the compound represented by Chemical Formula 3-1 was obtained by filtering and drying it. (Yield: 62.5 %)

合成例3-1:由化學式4-1表示的化合物的合成

Figure TW201800496AD00076
向甲醇(10 ml)與水(10 ml)的混合溶液中添加了由化學式2-1表示的化合物(3.8 mol)及由化學式3-1表示的化合物(4.15 mol),並接著與此同時進行了攪拌。向其中滴加了48%的氫氧化鈉水溶液(8.36 mol),且將混合物加熱至70℃並攪拌了3小時。使用薄層色譜法(thin layer chromatography,TLC)對反應進行了監視並接著完成了反應。將所得物冷卻至室溫,用水及己烷進行了洗滌,並進行了乾燥以獲得由化學式4-1表示的化合物。(產率:69 %)Synthesis Example 3-1: Synthesis of a compound represented by Chemical Formula 4-1
Figure TW201800496AD00076
To the mixed solution of methanol (10 ml) and water (10 ml), a compound (3.8 mol) represented by Chemical Formula 2-1 and a compound (4.15 mol) represented by Chemical Formula 3-1 were added, and then simultaneously Stir. A 48% aqueous sodium hydroxide solution (8.36 mol) was added dropwise thereto, and the mixture was heated to 70 ° C and stirred for 3 hours. The reaction was monitored using thin layer chromatography (TLC) and then the reaction was completed. The resultant was cooled to room temperature, washed with water and hexane, and dried to obtain a compound represented by Chemical Formula 4-1. (Yield: 69%)

合成例3-2:由化學式4-2表示的化合物的合成 [化學式4-2]

Figure TW201800496AD00077
根據與合成例3-1相同的方法使用由化學式2-2表示的化合物作為起始材料合成了由化學式4-2表示的化合物。(產率:71.8 %)Synthesis Example 3-2: Synthesis of Compound represented by Chemical Formula 4-2 [Chemical Formula 4-2]
Figure TW201800496AD00077
The compound represented by Chemical Formula 4-2 was synthesized by the same procedure as in Synthesis Example 3-1 using the compound represented by Chemical Formula 2-2 as a starting material. (Yield: 71.8 %)

合成例3-3:由化學式4-3表示的化合物的合成 [化學式4-3]

Figure TW201800496AD00078
根據與合成例3-1相同的方法使用由化學式2-3表示的化合物作為起始材料合成了由化學式4-3表示的化合物。(產率:70.2 %)Synthesis Example 3-3: Synthesis of Compound represented by Chemical Formula 4-3 [Chemical Formula 4-3]
Figure TW201800496AD00078
The compound represented by Chemical Formula 4-3 was synthesized by the same procedure as in Synthesis Example 3-1 using the compound represented by Chemical Formula 2-3 as a starting material. (Yield: 70.2%)

合成例3-4:由化學式4-4表示的化合物的合成 [化學式4-4]

Figure TW201800496AD00079
根據與合成例3-1相同的方法使用由化學式2-4表示的化合物作為起始材料合成了由化學式4-4表示的化合物。(產率:69.2 %)Synthesis Example 3-4: Synthesis of Compound represented by Chemical Formula 4-4 [Chemical Formula 4-4]
Figure TW201800496AD00079
The compound represented by Chemical Formula 4-4 was synthesized by the same procedure as in Synthesis Example 3-1 using the compound represented by Chemical Formula 2-4 as a starting material. (Yield: 69.2%)

合成例3-5:由化學式4-5表示的化合物的合成 [化學式4-5]

Figure TW201800496AD00080
根據與合成例3-1相同的方法使用由化學式2-5表示的化合物作為起始材料合成了由化學式4-5表示的化合物。(產率:70.1 %)Synthesis Example 3-5: Synthesis of a compound represented by Chemical Formula 4-5 [Chemical Formula 4-5]
Figure TW201800496AD00080
The compound represented by Chemical Formula 4-5 was synthesized by the same procedure as in Synthesis Example 3-1 using the compound represented by Chemical Formula 2-5 as a starting material. (Yield: 70.1%)

合成例3-6:由化學式4-6表示的化合物的合成 [化學式4-6]

Figure TW201800496AD00081
根據與合成例3-1相同的方法使用由化學式2-6表示的化合物作為起始材料合成了由化學式4-6表示的化合物。(產率:73.4 %)Synthesis Example 3-6: Synthesis of a compound represented by Chemical Formula 4-6 [Chemical Formula 4-6]
Figure TW201800496AD00081
The compound represented by Chemical Formula 4-6 was synthesized by the same procedure as in Synthesis Example 3-1 using the compound represented by Chemical Formula 2-6 as a starting material. (Yield: 73.4%)

合成例4-1:由化學式5-1表示的化合物的合成

Figure TW201800496AD00082
向乙酸(800 g)中添加了由化學式4-1表示的化合物(0.38 mol),並接著與此同時在室溫下進行了攪拌。向此反應溶液中添加了原甲酸三乙酯(0.23 mol),且將混合物加熱至130℃並攪拌了10小時。當反應完成之後,用乙腈(100 g)對所得物進行了過濾,且向其中添加了乙腈(100 g),並且將混合物進行了攪拌。對此溶液進行了過濾並然後用乙腈(100 g)進行了洗滌,且進行了乾燥以獲得由化學式5-1表示的化合物。(產率:68.7 %)Synthesis Example 4-1: Synthesis of a compound represented by Chemical Formula 5-1
Figure TW201800496AD00082
To the acetic acid (800 g), a compound (0.38 mol) represented by Chemical Formula 4-1 was added, and then stirred at room temperature at the same time. To the reaction solution was added triethyl orthoformate (0.23 mol), and the mixture was heated to 130 ° C and stirred for 10 hours. After the reaction was completed, the resultant was filtered with acetonitrile (100 g), and acetonitrile (100 g) was added thereto, and the mixture was stirred. This solution was filtered and then washed with acetonitrile (100 g) and dried to obtain a compound represented by Chemical Formula 5-1. (Yield: 68.7 %)

合成例4-2:由化學式5-2表示的化合物的合成 [化學式5-2]

Figure TW201800496AD00083
根據與合成例4-1相同的方法使用由化學式4-2表示的化合物作為起始材料合成了由化學式5-2表示的化合物。(產率:70.4 %)Synthesis Example 4-2: Synthesis of Compound represented by Chemical Formula 5-2 [Chemical Formula 5-2]
Figure TW201800496AD00083
The compound represented by Chemical Formula 5-2 was synthesized by the same procedure as in Synthesis Example 4-1 using the compound represented by Chemical Formula 4-2 as a starting material. (Yield: 70.4%)

合成例4-3:由化學式5-3表示的化合物的合成 [化學式5-3]

Figure TW201800496AD00084
根據與合成例4-1相同的方法使用由化學式4-3表示的化合物作為起始材料合成了由化學式5-3表示的化合物。(產率:69.6 %)Synthesis Example 4-3: Synthesis of Compound represented by Chemical Formula 5-3 [Chemical Formula 5-3]
Figure TW201800496AD00084
The compound represented by Chemical Formula 5-3 was synthesized by the same procedure as in Synthesis Example 4-1 using the compound represented by Chemical Formula 4-3 as a starting material. (Yield: 69.6 %)

合成例4-4:由化學式5-4表示的化合物的合成 [化學式5-4]

Figure TW201800496AD00085
根據與合成例4-1相同的方法使用由化學式4-4表示的化合物作為起始材料合成了由化學式5-4表示的化合物。(產率:71.9 %)Synthesis Example 4-4: Synthesis of Compound represented by Chemical Formula 5-4 [Chemical Formula 5-4]
Figure TW201800496AD00085
The compound represented by Chemical Formula 5-4 was synthesized by the same procedure as in Synthesis Example 4-1 using the compound represented by Chemical Formula 4-4 as a starting material. (Yield: 71.9 %)

合成例4-5:由化學式5-5表示的化合物的合成 [化學式5-5]

Figure TW201800496AD00086
根據與合成例4-1相同的方法使用由化學式4-5表示的化合物作為起始材料合成了由化學式5-5表示的化合物。(產率:74.2 %)Synthesis Example 4-5: Synthesis of a compound represented by Chemical Formula 5-5 [Chemical Formula 5-5]
Figure TW201800496AD00086
The compound represented by Chemical Formula 5-5 was synthesized by the same procedure as in Synthesis Example 4-1 using the compound represented by Chemical Formula 4-5 as a starting material. (Yield: 74.2%)

合成例4-6:由化學式5-6表示的化合物的合成 [化學式5-6]

Figure TW201800496AD00087
根據與合成例4-1相同的方法使用由化學式4-6表示的化合物作為起始材料合成了由化學式5-6表示的化合物。(產率:72.8 %)Synthesis Example 4-6: Synthesis of a compound represented by Chemical Formula 5-6 [Chemical Formula 5-6]
Figure TW201800496AD00087
The compound represented by Chemical Formula 5-6 was synthesized by the same procedure as in Synthesis Example 4-1 using the compound represented by Chemical Formula 4-6 as a starting material. (Yield: 72.8 %)

合成例5-1:由化學式6-1表示的化合物的合成

Figure TW201800496AD00088
向甲苯(17 ml)中添加了由化學式5-1表示的化合物,並與此同時進行了攪拌。向此溶液中滴加了氫氧化鈉(40%的水溶液,0.036 mmol)。隨後,在室溫下向其中添加了四丁基溴化銨(tetrabutyl ammonium bromide,TBAB,0.0012 mmol),將混合物攪拌了30分鐘並使用冰浴冷卻至0℃。向反應溶液中添加了1-金剛烷碳醯氯(1-adamantane carbonyl chloride)(0.072 mmol)。在移除冰浴後加熱至室溫的同時將混合物攪拌了2小時以完成反應。用水(100 ml)及乙酸乙酯(100 ml)對所得物進行了洗滌及乾燥以獲得由化學式6-1表示的化合物。(產率:72.5 %)Synthesis Example 5-1: Synthesis of a compound represented by Chemical Formula 6-1
Figure TW201800496AD00088
The compound represented by Chemical Formula 5-1 was added to toluene (17 ml), and stirred at the same time. To the solution was added dropwise sodium hydroxide (40% aqueous solution, 0.036 mmol). Subsequently, tetrabutyl ammonium bromide (TBAB, 0.0012 mmol) was added thereto at room temperature, and the mixture was stirred for 30 minutes and cooled to 0 ° C using an ice bath. 1-adamantane carbonyl chloride (0.072 mmol) was added to the reaction solution. The mixture was stirred for 2 hours while heating to room temperature after removing the ice bath to complete the reaction. The resultant was washed with water (100 ml) and ethyl acetate (100 ml) and dried to give a compound of formula 6-1. (Yield: 72.5 %)

合成例5-2:由化學式6-2表示的化合物的合成 [化學式6-2]

Figure TW201800496AD00089
根據與合成例5-1相同的方法使用由化學式5-1表示的化合物及4-甲氧基-2-甲基苯甲醯氯作為起始材料合成了由化學式6-2表示的化合物。(產率:74.2 %)Synthesis Example 5-2: Synthesis of Compound represented by Chemical Formula 6-2 [Chemical Formula 6-2]
Figure TW201800496AD00089
The compound represented by Chemical Formula 6-2 was synthesized by the same procedure as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-1 and 4-methoxy-2-methylbenzhydrin chloride as a starting material. (Yield: 74.2%)

合成例5-3:由化學式6-3表示的化合物的合成 [化學式6-3]

Figure TW201800496AD00090
根據與合成例5-1相同的方法使用由化學式5-2表示的化合物及1-金剛烷碳醯氯作為起始材料合成了由化學式6-3表示的化合物。(產率:74.5 %)Synthesis Example 5-3: Synthesis of Compound represented by Chemical Formula 6-3 [Chemical Formula 6-3]
Figure TW201800496AD00090
The compound represented by Chemical Formula 6-3 was synthesized by the same method as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-2 and 1-adamantanecarbofluorene as a starting material. (Yield: 74.5 %)

合成例5-4:由化學式6-4表示的化合物的合成 [化學式6-4]

Figure TW201800496AD00091
根據與合成例5-1相同的方法使用由化學式5-2表示的化合物及4-甲氧基-4-甲基苯甲醯氯作為起始材料合成了由化學式6-4表示的化合物。(產率:78.2 %)Synthesis Example 5-4: Synthesis of Compound represented by Chemical Formula 6-4 [Chemical Formula 6-4]
Figure TW201800496AD00091
The compound represented by Chemical Formula 6-4 was synthesized by the same procedure as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-2 and 4-methoxy-4-methylbenzhydrin chloride as a starting material. (Yield: 78.2%)

合成例5-5:由化學式6-5表示的化合物的合成 [化學式6-5]

Figure TW201800496AD00092
根據與合成例5-1相同的方法使用由化學式5-4表示的化合物及1-金剛烷碳醯氯作為起始材料合成了由化學式6-5表示的化合物。(產率:72.6 %)Synthesis Example 5-5: Synthesis of a compound represented by Chemical Formula 6-5 [Chemical Formula 6-5]
Figure TW201800496AD00092
The compound represented by Chemical Formula 6-5 was synthesized by the same method as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-4 and 1-adamantanecarbofluorene as a starting material. (Yield: 72.6 %)

合成例5-6:由化學式6-6表示的化合物的合成 [化學式6-6]

Figure TW201800496AD00093
根據與合成例5-1相同的方法使用由化學式5-5表示的化合物及1-金剛烷碳醯氯作為起始材料合成了由化學式6-6表示的化合物。(產率:70.4 %)Synthesis Example 5-6: Synthesis of a compound represented by Chemical Formula 6-6 [Chemical Formula 6-6]
Figure TW201800496AD00093
The compound represented by Chemical Formula 6-6 was synthesized by the same procedure as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-5 and 1-adamantanecarbofluorene as a starting material. (Yield: 70.4%)

合成例5-7:由化學式6-7表示的化合物的合成 [化學式6-7]

Figure TW201800496AD00094
根據與合成例5-1相同的方法使用由化學式5-5表示的化合物及4-甲氧基-2-甲基苯甲醯氯作為起始材料合成了由化學式6-7表示的化合物。(產率:74.6 %)Synthesis Example 5-7: Synthesis of a compound represented by Chemical Formula 6-7 [Chemical Formula 6-7]
Figure TW201800496AD00094
The compound represented by Chemical Formula 6-7 was synthesized by the same method as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-5 and 4-methoxy-2-methylbenzhydrin chloride as a starting material. (Yield: 74.6 %)

合成例5-8:由化學式6-8表示的化合物的合成 [化學式6-8]

Figure TW201800496AD00095
根據與合成例5-1相同的方法使用由化學式5-5表示的化合物及2-甲氧基苯甲醯氯作為起始材料合成了由化學式6-8表示的化合物。(產率:75.1 %)Synthesis Example 5-8: Synthesis of a compound represented by Chemical Formula 6-8 [Chemical Formula 6-8]
Figure TW201800496AD00095
The compound represented by Chemical Formula 6-8 was synthesized by the same method as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-5 and 2-methoxybenzimid chloride as a starting material. (Yield: 75.1%)

合成例5-9:由化學式6-9表示的化合物的合成 [化學式6-9]

Figure TW201800496AD00096
根據與合成例5-1相同的方法使用由化學式5-5表示的化合物及2-(甲硫基)苯甲醯氯作為起始材料合成了由化學式6-9表示的化合物。(產率:72.3 %)Synthesis Example 5-9: Synthesis of a compound represented by Chemical Formula 6-9 [Chemical Formula 6-9]
Figure TW201800496AD00096
The compound represented by Chemical Formula 6-9 was synthesized by the same procedure as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-5 and 2-(methylthio)benzhydrin chloride as a starting material. (Yield: 72.3 %)

合成例5-10:由化學式6-10表示的化合物的合成 [化學式6-10]

Figure TW201800496AD00097
根據與合成例5-1相同的方法使用由化學式5-6表示的化合物及4-甲氧基-2-甲基苯甲醯氯作為起始材料合成了由化學式6-10表示的化合物。(產率:72.3 %)Synthesis Example 5-10: Synthesis of a compound represented by Chemical Formula 6-10 [Chemical Formula 6-10]
Figure TW201800496AD00097
The compound represented by Chemical Formula 6-10 was synthesized by the same method as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-6 and 4-methoxy-2-methylbenzhydrin chloride as a starting material. (Yield: 72.3 %)

合成例5-11:由化學式6-11表示的化合物的合成 [化學式6-11]

Figure TW201800496AD00098
根據與合成例5-1相同的方法使用由化學式5-2表示的化合物及2-三氟甲基苯甲醯氯作為起始材料合成了由化學式6-11表示的化合物。(產率:78.2 %)Synthesis Example 5-11: Synthesis of a compound represented by Chemical Formula 6-11 [Chemical Formula 6-11]
Figure TW201800496AD00098
The compound represented by Chemical Formula 6-11 was synthesized by the same procedure as in Synthesis Example 5-1 using the compound represented by Chemical Formula 5-2 and 2-trifluoromethylbenzhydrin chloride as a starting material. (Yield: 78.2%)

合成例6-1:由化學式7-1表示的化合物的合成

Figure TW201800496AD00099
向水(60 ml)/甲醇(90 ml)的混合溶液中添加了4-叔丁基苯甲酸(0.14 mol)及甲醇鈉(30%的甲醇溶液,0.14 mol)。向此溶液中添加了硫酸鋅7水合物(0.06 mol)。在室溫下將混合物攪拌了1小時以完成反應。當反應完成之後,對所得物進行了過濾,用水(1000 ml)及甲醇(1000 ml)進行洗滌以獲得由化學式7-1表示的化合物。(產率:90.1 %)Synthesis Example 6-1: Synthesis of a compound represented by Chemical Formula 7-1
Figure TW201800496AD00099
To a mixed solution of water (60 ml) / methanol (90 ml) was added 4-tert-butylbenzoic acid (0.14 mol) and sodium methoxide (30% methanol solution, 0.14 mol). To this solution was added zinc sulfate 7 hydrate (0.06 mol). The mixture was stirred at room temperature for 1 hour to complete the reaction. After the reaction was completed, the resultant was filtered, washed with water (1000 ml) and methanol (1000 ml) to obtain a compound represented by the formula 7-1. (Yield: 90.1%)

合成例6-2:由化學式7-2表示的化合物的合成 [化學式7-2]

Figure TW201800496AD00100
根據與合成例6-1相同的方法使用2-(2,3-二甲基苯基氨基)苯甲酸作為起始材料合成了由化學式7-2表示的化合物。(產率:93.3 %)Synthesis Example 6-2: Synthesis of Compound represented by Chemical Formula 7-2 [Chemical Formula 7-2]
Figure TW201800496AD00100
The compound represented by Chemical Formula 7-2 was synthesized by the same method as in Synthesis Example 6-1 using 2-(2,3-dimethylphenylamino)benzoic acid as a starting material. (Yield: 93.3%)

合成例7-1:由化學式1-1表示的化合物(染料)的合成

Figure TW201800496AD00101
向乙醇(10 ml)中添加了由化學式6-1表示的化合物(0.642 mmol)及由化學式7-1表示的化合物(0.835 mmol),並與此同時在室溫下進行了攪拌。用薄層色譜法對反應進行了檢查並完成了反應。在對反應溶液的乙醇進行乾燥之後用亞甲基氯(100 ml)及水(100 ml)對所得物進行了洗滌,以獲得由化學式1-1表示的化合物。(產率:81.7%,基質輔助雷射脫吸離子化飛行時間質譜(matrix-assisted laser desorption/ionization time-of-flight mass spectrometry,Maldi tof Mass):1454.8)Synthesis Example 7-1: Synthesis of Compound (Dye) represented by Chemical Formula 1-1
Figure TW201800496AD00101
A compound (0.642 mmol) represented by Chemical Formula 6-1 and a compound (0.835 mmol) represented by Chemical Formula 7-1 were added to ethanol (10 ml), and stirred at room temperature. The reaction was examined by thin layer chromatography and the reaction was completed. After drying the ethanol of the reaction solution, the resultant was washed with methylene chloride (100 ml) and water (100 ml) to obtain a compound represented by Chemical Formula 1-1. (Yield: 81.7%, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, Maldi tof Mass: 1454.8)

合成例7-2:由化學式1-2表示的化合物(染料)的合成 [化學式1-2]

Figure TW201800496AD00102
基質輔助雷射脫吸離子化飛行時間質譜:1426.7 根據與合成例7-1相同的方法使用由化學式6-4表示的化合物及由化學式7-1表示的化合物作為起始材料合成了由化學式1-2表示的化合物。(產率:82.8%)Synthesis Example 7-2: Synthesis of Compound (Dye) represented by Chemical Formula 1-2 [Chemical Formula 1-2]
Figure TW201800496AD00102
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1426.7 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-4 and the compound represented by Chemical Formula 7-1 as a starting material. a compound represented by -2. (Yield: 82.8%)

合成例7-3:由化學式1-3表示的化合物(染料)的合成 [化學式1-3]

Figure TW201800496AD00103
基質輔助雷射脫吸離子化飛行時間質譜:1465.7 根據與合成例7-1相同的方法使用由化學式6-5表示的化合物及由化學式7-1表示的化合物作為起始材料合成了由化學式1-3表示的化合物。(產率:84.1%)Synthesis Example 7-3: Synthesis of Compound (Dye) Represented by Chemical Formula 1-3 [Chemical Formula 1-3]
Figure TW201800496AD00103
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1465.7 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-5 and the compound represented by Chemical Formula 7-1 as a starting material. a compound represented by -3. (Yield: 84.1%)

合成例7-4:由化學式1-4表示的化合物(染料)的合成 [化學式1-4]

Figure TW201800496AD00104
基質輔助雷射脫吸離子化飛行時間質譜:1547.9 根據與合成例7-1相同的方法使用由化學式6-6表示的化合物及由化學式7-1表示的化合物作為起始材料合成了由化學式1-4表示的化合物。(產率:87.2 %)Synthesis Example 7-4: Synthesis of Compound (Dye) Represented by Chemical Formula 1-4 [Chemical Formula 1-4]
Figure TW201800496AD00104
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1547.9 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-6 and the compound represented by Chemical Formula 7-1 as a starting material. a compound represented by -4. (Yield: 87.2%)

合成例7-5:由化學式1-5表示的化合物(染料)的合成 [化學式1-5]

Figure TW201800496AD00105
基質輔助雷射脫吸離子化飛行時間質譜:1491.7 根據與合成例7-1相同的方法使用由化學式7-1表示的化合物作為起始材料合成了由化學式1-5表示的化合物。(產率:82.2 %)Synthesis Example 7-5: Synthesis of Compound (Dye) represented by Chemical Formula 1-5 [Chemical Formula 1-5]
Figure TW201800496AD00105
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1491.7 The compound represented by Chemical Formula 1-5 was synthesized by the same procedure as in Synthesis Example 7-1 using the compound represented by Chemical Formula 7-1 as a starting material. (Yield: 82.2%)

合成例7-6:由化學式1-6表示的化合物(染料)的合成 [化學式1-6]

Figure TW201800496AD00106
基質輔助雷射脫吸離子化飛行時間質譜:1522.67 根據與合成例7-1相同的方法使用由化學式6-9表示的化合物及由化學式7-1表示的化合物作為起始材料合成了由化學式1-6表示的化合物。(產率:81.8 %)Synthesis Example 7-6: Synthesis of Compound (Dye) Represented by Chemical Formula 1-6 [Chemical Formula 1-6]
Figure TW201800496AD00106
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1522.67 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-9 and the compound represented by Chemical Formula 7-1 as a starting material. a compound represented by -6. (Yield: 81.8 %)

合成例7-7:由化學式1-7表示的化合物(染料)的合成 [化學式1-7]

Figure TW201800496AD00107
基質輔助雷射脫吸離子化飛行時間質譜:1489.72 根據與合成例7-1相同的方法使用由化學式6-2表示的化合物及由化學式7-2表示的化合物作為起始材料合成了由化學式1-7表示的化合物。(產率:85.8 %)Synthesis Example 7-7: Synthesis of Compound (Dye) represented by Chemical Formula 1-7 [Chemical Formula 1-7]
Figure TW201800496AD00107
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1498.72 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-2 and the compound represented by Chemical Formula 7-2 as a starting material. a compound represented by -7. (Yield: 85.8 %)

合成例7-8:由化學式1-8表示的化合物(染料)的合成 [化學式1-8]

Figure TW201800496AD00108
基質輔助雷射脫吸離子化飛行時間質譜:1454.81 根據與合成例7-1相同的方法使用由化學式6-3表示的化合物及由化學式7-2表示的化合物作為起始材料合成了由化學式1-8表示的化合物。(產率:82.3 %)Synthesis Example 7-8: Synthesis of Compound (Dye) represented by Chemical Formula 1-8 [Chemical Formula 1-8]
Figure TW201800496AD00108
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1454.81 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-3 and the compound represented by Chemical Formula 7-2 as a starting material. a compound represented by -8. (Yield: 82.3 %)

合成例7-9:由化學式1-9表示的化合物(染料)的合成 [化學式1-9]

Figure TW201800496AD00109
基質輔助雷射脫吸離子化飛行時間質譜:1541.49 根據與合成例7-1相同的方法使用由化學式6-7表示的化合物及由化學式7-2表示的化合物作為起始材料合成了由化學式1-9表示的化合物。(產率:84.3 %)Synthesis Example 7-9: Synthesis of Compound (Dye) represented by Chemical Formula 1-9 [Chemical Formula 1-9]
Figure TW201800496AD00109
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1541.19 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-7 and the compound represented by Chemical Formula 7-2 as a starting material. a compound represented by -9. (Yield: 84.3 %)

合成例7-10:由化學式1-10表示的化合物(染料)的合成 [化學式1-10]

Figure TW201800496AD00110
基質輔助雷射脫吸離子化飛行時間質譜:1569.52 根據與合成例7-1相同的方法使用由化學式6-8表示的化合物及由化學式7-2表示的化合物作為起始材料合成了由化學式1-10表示的化合物。(產率:80.6 %)Synthesis Example 7-10: Synthesis of Compound (Dye) represented by Chemical Formula 1-10 [Chemical Formula 1-10]
Figure TW201800496AD00110
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1659.52 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-8 and the compound represented by Chemical Formula 7-2 as a starting material. a compound represented by -10. (Yield: 80.6 %)

合成例7-11:由化學式1-11表示的化合物(染料)的合成 [化學式1-11]

Figure TW201800496AD00111
基質輔助雷射脫吸離子化飛行時間質譜:1429.17 根據與合成例7-1相同的方法使用由化學式6-2表示的化合物及由化學式7-1表示的化合物作為起始材料合成了由化學式1-11表示的化合物(染料)。(產率:85.8 %)Synthesis Example 7-11: Synthesis of Compound (Dye) represented by Chemical Formula 1-11 [Chemical Formula 1-11]
Figure TW201800496AD00111
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1429.17 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-2 and the compound represented by Chemical Formula 7-1 as a starting material. Compound (dye) represented by -11. (Yield: 85.8 %)

合成例7-12:由化學式1-12表示的化合物(染料)的合成 [化學式1-12]

Figure TW201800496AD00112
基質輔助雷射脫吸離子化飛行時間質譜:1401.11 根據與合成例7-1相同的方法使用由化學式6-11表示的化合物及由化學式7-2表示的化合物作為起始材料合成了由化學式1-12表示的化合物(染料)。(產率:85.8 %)Synthesis Example 7-12: Synthesis of Compound (Dye) represented by Chemical Formula 1-12 [Chemical Formula 1-12]
Figure TW201800496AD00112
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1401.11 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-11 and the compound represented by Chemical Formula 7-2 as a starting material. Compound (dye) represented by -12. (Yield: 85.8 %)

比較合成例1:由化學式C-1表示的化合物的合成 [化學式C-1]

Figure TW201800496AD00113
基質輔助雷射脫吸離子化飛行時間質譜:1366.69 根據與合成例7-1相同的方法使用由化學式6-10表示的化合物及由化學式7-1表示的化合物作為起始材料合成了由化學式C-1表示的化合物。(產率:78.6 %)Comparative Synthesis Example 1: Synthesis of a compound represented by Chemical Formula C-1 [Chemical Formula C-1]
Figure TW201800496AD00113
Matrix-assisted laser desorption ionization time-of-flight mass spectrometry: 1366.69 was synthesized according to the same method as in Synthesis Example 7-1 using the compound represented by Chemical Formula 6-10 and the compound represented by Chemical Formula 7-1 as a starting material. a compound represented by -1. (Yield: 78.6 %)

評估1:溶解度測量Assessment 1: Solubility Measurement

分別向0.5 g在合成例7-1至合成例7-12以及比較合成例1中合成的每一化合物中添加了稀釋溶劑(Anone),用旋轉混合機(米克斯羅塔(MIXROTAR)VMR-5,路馳公司(Luchi Inc.))在25℃及100 rpm下將每一種溶液攪拌了1小時,然後對每一化合物的溶解度進行了確認且結果示於表1中。(Anone指代環己酮(cyclohexanone)。)A dilution solvent (Anone) was added to each of 0.5 g of each compound synthesized in Synthesis Example 7-1 to Synthesis Example 7-12 and Comparative Synthesis Example 1, respectively, using a rotary mixer (MIXROTAR VMR) -5, Luchi Inc.) Each solution was stirred at 25 ° C and 100 rpm for 1 hour, and then the solubility of each compound was confirmed and the results are shown in Table 1. (Anone refers to cyclohexanone.)

溶解度評估參考 基於稀釋溶劑的總量,化合物(溶質)大於或等於2.5重量%:○ 基於稀釋溶劑的總量,化合物(溶質)小於2.5重量%:×Solubility Evaluation Reference The compound (solute) is greater than or equal to 2.5% by weight based on the total amount of the diluent solvent: ○ The compound (solute) is less than 2.5% by weight based on the total amount of the diluent solvent: ×

[表1] (單位:重量%)

Figure TW201800496AD00114
[Table 1] (Unit: % by weight)
Figure TW201800496AD00114

參考表1,根據實例7-1至實例7-12的化合物(根據實施例的化合物)與根據比較合成例1的化合物相比具有關於有機溶劑的優異的溶解度,且因此當用於感光性樹脂組成物等時顯示出了優異的色彩特性。Referring to Table 1, the compounds according to Examples 7-1 to 7-12 (compounds according to the examples) have excellent solubility with respect to an organic solvent as compared with the compound according to Comparative Synthesis Example 1, and thus when used for a photosensitive resin The composition and the like exhibit excellent color characteristics.

(感光性樹脂組成物的合成)(Synthesis of photosensitive resin composition)

實例1至實例14以及比較例1至比較例4Example 1 to Example 14 and Comparative Example 1 to Comparative Example 4

使用表2及表3中所示的以下成分將根據實例1至實例14以及比較例1至比較例4的感光性樹脂組成物製備成具有每一種組成。The photosensitive resin compositions according to Examples 1 to 14 and Comparative Examples 1 to 4 were prepared to have each composition using the following components shown in Table 2 and Table 3.

具體來說,將光聚合引發劑溶解在溶劑中,在室溫下將溶液攪拌了2小時,向其中添加了黏合劑樹脂及光可聚合化合物,且在室溫下將混合物攪拌了2小時。隨後,向所獲得的反應物中添加了染料及顏料分散液作為著色劑,且在室溫下將所獲得的混合物攪拌了一小時。然後,將由此得到的產物過濾了3次以移除雜質從而製備感光性樹脂組成物。Specifically, the photopolymerization initiator was dissolved in a solvent, and the solution was stirred at room temperature for 2 hours, and a binder resin and a photopolymerizable compound were added thereto, and the mixture was stirred at room temperature for 2 hours. Subsequently, a dye and a pigment dispersion were added as a colorant to the obtained reactant, and the obtained mixture was stirred at room temperature for one hour. Then, the product thus obtained was filtered 3 times to remove impurities to prepare a photosensitive resin composition.

(A)黏合劑樹脂 丙烯酸系黏合劑樹脂(OH-139,三星SDI有限公司(Samsung SDI Co., Ltd.))(A) Adhesive Resin Acrylic Adhesive Resin (OH-139, Samsung SDI Co., Ltd.)

(B)著色劑 染料 (B-1)合成例7-1的化合物(由化學式1-1表示的化合物) (B-2)合成例7-2的化合物(由化學式1-2表示的化合物) (B-3)合成例7-3的化合物(由化學式1-3表示的化合物) (B-4)合成例7-4的化合物(由化學式1-4表示的化合物) (B-5)合成例7-5的化合物(由化學式1-5表示的化合物) (B-6)合成例7-6的化合物(由化學式1-6表示的化合物) (B-7)合成例7-7的化合物(由化學式1-7表示的化合物) (B-8)合成例7-8的化合物(由化學式1-8表示的化合物) (B-9)合成例7-9的化合物(由化學式1-9表示的化合物) (B-10)合成例7-10的化合物(由化學式1-10表示的化合物) (B-11)合成例7-11的化合物(由化學式1-11表示的化合物) (B-12)合成例7-12的化合物(由化學式1-12表示的化合物) (B-13)比較合成例1的化合物(由化學式C-1表示的化合物) 顏料分散液 (B-14)C.I.顏料藍15:6分散液(GC1679,三洋公司(Sanyo)) (B-15)「藍15:6+紫色染料」共分散液(GC1207,三洋公司)(B) Colorant Dye (B-1) Compound of Synthesis Example 7-1 (Compound represented by Chemical Formula 1-1) (B-2) Compound of Synthesis Example 7-2 (Compound represented by Chemical Formula 1-2) (B-3) Compound of Synthesis Example 7-3 (Compound represented by Chemical Formula 1-3) (B-4) Synthesis of Compound of Example 7-4 (Compound represented by Chemical Formula 1-4) (B-5) Synthesis Compound of Example 7-5 (compound represented by Chemical Formula 1-5) (B-6) Synthesis of Compound of Example 7-6 (Compound represented by Chemical Formula 1-6) (B-7) Synthesis of Compound of Example 7-7 (Compound represented by Chemical Formula 1-7) (B-8) The compound of Synthesis Example 7-8 (compound represented by Chemical Formula 1-8) (B-9) The compound of Synthesis Example 7-9 (Chemical Formula 1-9) (B-10) Compound of Synthesis Example 7-10 (Compound represented by Chemical Formula 1-10) (B-11) Compound of Synthesis Example 7-11 (Compound represented by Chemical Formula 1-11) (B) -12) Compound of Synthesis Example 7-12 (compound represented by Chemical Formula 1-12) (B-13) Comparative Compound of Synthesis Example 1 (Compound represented by Chemical Formula C-1) Pigment Dispersion (B-14) C.I Pigment Blue 15: 6 dispersion (GC1679, Sanyo (Sanyo)) (B-15) "blue 15: violet dye 6+" co-dispersing liquid (GC1207, Sanyo)

(C)光可聚合單體 DPHA(日本化藥有限公司)(C) Photopolymerizable monomer DPHA (Japan Chemicals Co., Ltd.)

(D)光聚合引發劑 肟系引發劑(OXE01,巴斯夫公司(BASF))(D) Photopolymerization initiator Lanthanide initiator (OXE01, BASF)

(E)溶劑 丙二醇單甲醚乙酸酯(PGMEA,共和有限公司(Kyowa Co., Ltd.))(E) Solvent propylene glycol monomethyl ether acetate (PGMEA, Kyowa Co., Ltd.)

(F)其他添加劑 氟系表面活性劑(F-554,迪愛生有限公司(DIC Co., Ltd.))(F) Other additives Fluoride-based surfactant (F-554, DIC Co., Ltd.)

[表2] (單位:重量%)

Figure TW201800496AD00115
[Table 2] (Unit: % by weight)
Figure TW201800496AD00115

[表3] (單位:重量%)

Figure TW201800496AD00116
[Table 3] (Unit: % by weight)
Figure TW201800496AD00116

評估2:亮度、耐熱性、及耐化學性的測量Assessment 2: Measurement of brightness, heat resistance, and chemical resistance

在1 mm厚的脫脂玻璃(degreased glass)基板上分別將根據實例1至實例14以及比較例1至比較例4的感光性樹脂組成物塗布為1 μm至3 μm厚,並接著在90℃的加熱板上乾燥了2分鐘以獲得膜(250 rpm至350 rpm)。使用具有365 nm的主要波長的高壓汞燈(曝光條件:50 mJ/cm2 )將膜曝光,並使用經111倍稀釋的KOH顯影溶液(洗滌溶液/顯影溶液=1/0.8)在顯影劑中顯影了60秒。隨後,將膜在230℃的強制對流乾燥爐中乾燥了20分鐘以獲得彩色樣本。The photosensitive resin compositions according to Examples 1 to 14 and Comparative Examples 1 to 4 were respectively coated to a thickness of 1 μm to 3 μm on a 1 mm thick degresed glass substrate, and then at 90 ° C. The plate was dried for 2 minutes to obtain a film (250 rpm to 350 rpm). The film was exposed using a high pressure mercury lamp (exposure condition: 50 mJ/cm 2 ) having a main wavelength of 365 nm, and a 111-fold diluted KOH developing solution (washing solution/developing solution = 1/0.8) was used in the developer. Developed for 60 seconds. Subsequently, the film was dried in a forced convection drying oven at 230 ° C for 20 minutes to obtain a color sample.

使用分光光度計(MCPD3000,大塚電子有限公司(Otsuka Electronics Co., Ltd.))(基於C光源)測量了彩色樣本的亮度(基於0.1065),且結果示於表4中。The luminance of the color sample (based on 0.1065) was measured using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.) (based on C light source), and the results are shown in Table 4.

將彩色樣本在230℃下在對流烘箱中又乾燥了60分鐘,且使用分光光度計(MCPD3000,大塚電子有限公司)(基於C光源)測量了彩色樣本在乾燥之前與乾燥之後的色彩差異,且接著測量了樣本的耐熱性(DEab*),並且結果示於表4中。The color samples were dried again in a convection oven at 230 ° C for 60 minutes, and the color difference of the color samples before and after drying was measured using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.) based on the C light source, and The heat resistance (DEab*) of the sample was then measured, and the results are shown in Table 4.

將彩色樣本在80℃的甲基吡咯烷酮(methyl pyrrolidone,NMP)溶液中沉澱了1分鐘,使用紫外-可見光譜儀(UV-VIS)對彩色樣本的甲基吡咯烷酮溶液的吸光度進行了分析以測量其耐化學性(耐洗脫性),且結果示於表4中。The color samples were precipitated in a methyl pyrrolidone (NMP) solution at 80 ° C for 1 minute, and the absorbance of the color sample of the methylpyrrolidone solution was analyzed using an ultraviolet-visible spectrometer (UV-VIS) to measure the resistance. Chemical (elution resistance), and the results are shown in Table 4.

[表4]

Figure TW201800496AD00117
[Table 4]
Figure TW201800496AD00117

參考表4,與不包含由化學式1表示的化合物作為染料或包含超出以下所述範圍的化合物的感光性樹脂組成物相比,以感光性樹脂組成物的總量計包含5重量%至20重量%、例如10重量%至15重量%的量的由化學式1表示的化合物作為染料的感光性樹脂組成物顯示出了優異的色彩特性、耐熱性、及耐化學性。Referring to Table 4, the photosensitive resin composition containing the chemical formula 1 as a dye or a photosensitive resin composition containing a compound exceeding the range described below is contained in an amount of 5 to 20% by weight based on the total amount of the photosensitive resin composition. The photosensitive resin composition of the compound represented by Chemical Formula 1 as a dye in an amount of, for example, 10% by weight to 15% by weight, exhibits excellent color characteristics, heat resistance, and chemical resistance.

雖然已結合目前被認為是實用的示例性實施例對本發明進行了闡述,但是應理解,本發明並不僅限於所公開的實施例,而是相反地,本發明旨在涵蓋包含在隨附申請專利範圍的精神及範圍內的各種修改形式及等效佈置。While the present invention has been described in connection with the exemplary embodiments of the present invention, it is understood that the invention is not limited to the disclosed embodiments, but rather, the invention is intended to cover Various modifications and equivalent arrangements within the spirit and scope of the scope.

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Claims (20)

一種化合物,由化學式1表示: [化學式1]其中,在化學式1中, R1 為鹵素原子、經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基, R2 為經取代或未經取代的C3至C20脂環族環狀基、或者經取代或未經取代的C6至C20芳基,其限制條件是所述芳基僅具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基, R3 至R5 獨立地為經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基, m及n獨立地為介於1至5範圍內的整數,且 L由化學式2表示, [化學式2]其中,在化學式2中, L1 為-O(C=O)-或-S-,且 A為經取代或未經取代的C1至C20烷基、經取代或未經取代的C3至C20脂環族環狀基、經取代或未經取代的C6至C20芳基、或者經取代或未經取代的C2至C20雜芳基。A compound represented by Chemical Formula 1: [Chemical Formula 1] Wherein, in Chemical Formula 1, R 1 is a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to a C20 aryl group, R 2 is a substituted or unsubstituted C 3 to C 20 alicyclic cyclic group, or a substituted or unsubstituted C 6 to C 20 aryl group, with the proviso that the aryl group has only at least one a substituent selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 alkylthio group R 3 to R 5 are independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group, m and n are independently an integer ranging from 1 to 5, and L is represented by Chemical Formula 2, [Chemical Formula 2] Wherein, in Chemical Formula 2, L 1 is -O(C=O)- or -S-, and A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 fat. a cyclocyclic group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group. 如申請專利範圍第1項所述的化合物,其中R1 為經取代或未經取代的C1至C20烷基、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基。The compound of claim 1, wherein R 1 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted group. C6 to C20 aryl. 如申請專利範圍第1項所述的化合物,其中R2 為經取代或未經取代的金剛烷基、或者經取代或未經取代的苯基,其限制條件是所述苯基僅具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基的取代基。The compound of claim 1, wherein R 2 is a substituted or unsubstituted adamantyl group, or a substituted or unsubstituted phenyl group, with the proviso that the phenyl group has only at least one a substituent selected from a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 alkylthio group. 如申請專利範圍第3項所述的化合物,其中R2 為所述未經取代的金剛烷基或者僅具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基的所述苯基。The compound of claim 3, wherein R 2 is the unsubstituted adamantyl group or has at least one selected from the group consisting of a halogen atom, a substituted or unsubstituted C1 to C10 alkyl group, and substituted Or the unsubstituted C1 to C10 alkoxy group, and the substituted or unsubstituted C1 to C10 alkylthio group of the phenyl group. 如申請專利範圍第1項所述的化合物,其中R3 至R5 獨立地為經取代或未經取代的C1至C20烷基。The compound of claim 1, wherein R 3 to R 5 are independently a substituted or unsubstituted C1 to C20 alkyl group. 如申請專利範圍第1項所述的化合物,其中L由選自化學式3至化學式7中的一者表示: [化學式3][化學式4][化學式5][化學式6][化學式7]其中,在化學式3至化學式7中, R6 為經取代或未經取代的C1至C10烷基、經取代或未經取代的氨基、或者經取代或未經取代的醯基, R7 至R9 獨立地為羥基或者經取代或未經取代的C1至C10烷基,其限制條件是R7 及R8 中的至少一者為羥基, R10 為經取代或未經取代的C1至C10烷基, o及p獨立地為介於1至3範圍內的整數,其限制條件是2 ≤ o + p ≤ 5,且 q為介於0至4範圍內的整數。The compound according to claim 1, wherein L is represented by one selected from Chemical Formula 3 to Chemical Formula 7: [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] Wherein, in Chemical Formula 3 to Chemical Formula 7, R 6 is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted fluorenyl group, R 7 to R 9 independently of a hydroxy group or a substituted or unsubstituted C1 to C10 alkyl group, with the proviso that at least one of R 7 and R 8 is a hydroxyl group, and R 10 is a substituted or unsubstituted C1 to C10 alkane The bases, o and p are independently integers ranging from 1 to 3, with the constraint being 2 ≤ o + p ≤ 5, and q being an integer ranging from 0 to 4. 如申請專利範圍第6項所述的化合物,其中所述經取代或未經取代的氨基由化學式8表示,且所述經取代或未經取代的醯基由化學式9表示: [化學式8][化學式9]其中,在化學式8中, Rx 為經取代或未經取代的C1至C10烷基,且 z為介於0至5範圍內的整數。The compound according to claim 6, wherein the substituted or unsubstituted amino group is represented by Chemical Formula 8, and the substituted or unsubstituted fluorenyl group is represented by Chemical Formula 9: [Chemical Formula 8] [Chemical Formula 9] Wherein, in Chemical Formula 8, R x is a substituted or unsubstituted C1 to C10 alkyl group, and z is an integer ranging from 0 to 5. 如申請專利範圍第6項所述的化合物,其中R6為叔丁基、由化學式8表示的取代基、或由化學式9表示的取代基, R7 至R9 獨立地為羥基或叔丁基,其限制條件是R7 及R8 中的至少一者為羥基, R10 為經取代或未經取代的甲基、經取代或未經取代的乙基、經取代或未經取代的丙基、經取代或未經取代的丁基、或者經取代或未經取代的戊基: [化學式8][化學式9]其中,在化學式8中, Rx 為經取代或未經取代的C1至C10烷基,且 z為介於0至5範圍內的整數。The compound according to claim 6, wherein R6 is a tert-butyl group, a substituent represented by Chemical Formula 8, or a substituent represented by Chemical Formula 9, and R 7 to R 9 are independently a hydroxyl group or a t-butyl group. The limitation is that at least one of R 7 and R 8 is a hydroxyl group, and R 10 is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, Substituted or unsubstituted butyl group, or substituted or unsubstituted pentyl group: [Chemical Formula 8] [Chemical Formula 9] Wherein, in Chemical Formula 8, R x is a substituted or unsubstituted C1 to C10 alkyl group, and z is an integer ranging from 0 to 5. 如申請專利範圍第1項所述的化合物,其中化學式1由化學式10-1或化學式10-2表示: [化學式10-1][化學式10-2]其中,在化學式10-1及化學式10-2中, R1 為鹵素原子、經取代或未經取代的C1至C20烷氧基、或者經取代或未經取代的C6至C20芳基, R2 為經取代或未經取代的C3至C20脂環族環狀基、或者經取代或未經取代的C6至C20芳基,其限制條件是所述芳基具有至少一個選自鹵素原子、經取代或未經取代的C1至C10烷基、經取代或未經取代的C1至C10烷氧基、及經取代或未經取代的C1至C10烷硫基中的取代基, R3 至R5 獨立地為經取代或未經取代的C1至C20烷基,且 L由化學式2表示, [化學式2]其中,在化學式2中, L1 為-O(C=O)-,且 A為經取代或未經取代的C1至C20烷基、經取代或未經取代的C3至C20脂環族環狀基、或者經取代或未經取代的C6至C20芳基。The compound according to claim 1, wherein the chemical formula 1 is represented by Chemical Formula 10-1 or Chemical Formula 10-2: [Chemical Formula 10-1] [Chemical Formula 10-2] Wherein, in Chemical Formula 10-1 and Chemical Formula 10-2, R 1 is a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group, or a substituted or unsubstituted C6 to C20 aryl group, R 2 a substituted or unsubstituted C3 to C20 alicyclic cyclic group, or a substituted or unsubstituted C6 to C20 aryl group, with the proviso that the aryl group has at least one selected from a halogen atom and substituted Or an unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, and a substituted or unsubstituted C1 to C10 alkylthio group, R 3 to R 5 independently The ground is a substituted or unsubstituted C1 to C20 alkyl group, and L is represented by Chemical Formula 2, [Chemical Formula 2] Wherein, in Chemical Formula 2, L 1 is -O(C=O)-, and A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring. A substituted or unsubstituted C6 to C20 aryl group. 如申請專利範圍第1項所述的化合物,其中化學式1由選自化學式1-1至化學式1-12中的一者表示: [化學式1-1][化學式1-2][化學式1-3][化學式1-4][化學式1-5][化學式1-6][化學式1-7][化學式1-8][化學式1-9][化學式1-10][化學式1-11][化學式1-12]The compound according to claim 1, wherein the chemical formula 1 is represented by one selected from the group consisting of Chemical Formula 1-1 to Chemical Formula 1-12: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] . 如申請專利範圍第1項所述的化合物,其中由化學式1表示的化合物在450 nm至600 nm的波長範圍內具有最大吸光度。The compound according to claim 1, wherein the compound represented by Chemical Formula 1 has a maximum absorbance in a wavelength range of 450 nm to 600 nm. 一種感光性樹脂組成物,包含如申請專利範圍第1項至第11項中任一項所述的化合物作為染料。A photosensitive resin composition comprising the compound according to any one of claims 1 to 11 as a dye. 如申請專利範圍第12項所述的感光性樹脂組成物,其中所述感光性樹脂組成物更包含黏合劑樹脂、顏料、光可聚合單體、光聚合引發劑、及溶劑。The photosensitive resin composition according to claim 12, wherein the photosensitive resin composition further comprises a binder resin, a pigment, a photopolymerizable monomer, a photopolymerization initiator, and a solvent. 如申請專利範圍第12項所述的感光性樹脂組成物,其中以所述感光性樹脂組成物的總量計,包含5重量%至20重量%的量的所述染料。The photosensitive resin composition according to claim 12, wherein the dye is contained in an amount of from 5% by weight to 20% by weight based on the total of the photosensitive resin composition. 如申請專利範圍第14項所述的感光性樹脂組成物,其中以所述感光性樹脂組成物的總量計,包含10重量%至15重量%的量的所述染料。The photosensitive resin composition according to claim 14, wherein the dye is contained in an amount of 10% by weight to 15% by weight based on the total of the photosensitive resin composition. 如申請專利範圍第13項所述的感光性樹脂組成物,其中所述顏料為藍色顏料。The photosensitive resin composition according to claim 13, wherein the pigment is a blue pigment. 如申請專利範圍第13項所述的感光性樹脂組成物,其中所述黏合劑樹脂包括丙烯酸系黏合劑樹脂、卡多系黏合劑樹脂、或其組合。The photosensitive resin composition according to claim 13, wherein the binder resin comprises an acrylic binder resin, a cardo binder resin, or a combination thereof. 如申請專利範圍第13項所述的感光性樹脂組成物,其中以所述感光性樹脂組成物的總量計,所述感光性樹脂組成物包含 1重量%至10重量%的所述黏合劑樹脂; 45重量%至80重量%的包含所述染料及所述顏料的著色劑; 1重量%至5重量%的所述光可聚合單體; 0.1重量%至3重量%的所述光聚合引發劑;以及 餘量的所述溶劑。The photosensitive resin composition according to claim 13, wherein the photosensitive resin composition contains 1% by weight to 10% by weight of the binder based on the total amount of the photosensitive resin composition. Resin; 45% by weight to 80% by weight of a coloring agent comprising the dye and the pigment; 1% by weight to 5% by weight of the photopolymerizable monomer; 0.1% by weight to 3% by weight of the photopolymerizable An initiator; and the balance of the solvent. 如申請專利範圍第12項所述的感光性樹脂組成物,其中所述感光性樹脂組成物更包含以下添加劑:丙二酸;3-氨基-1,2-丙二醇;矽烷系偶合劑;流平劑;氟系表面活性劑;自由基聚合引發劑;或其組合。The photosensitive resin composition according to claim 12, wherein the photosensitive resin composition further comprises the following additives: malonic acid; 3-amino-1,2-propanediol; decane-based coupling agent; a fluorine-based surfactant; a radical polymerization initiator; or a combination thereof. 一種彩色濾光片,包括使用如申請專利範圍第12項所述的感光性樹脂組成物製造的感光性樹脂膜。A color filter comprising a photosensitive resin film produced by using the photosensitive resin composition according to claim 12 of the patent application.
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