TW201726885A - Color conversion composition, color conversion film, and light source unit, display and lighting system containing same - Google Patents

Color conversion composition, color conversion film, and light source unit, display and lighting system containing same Download PDF

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TW201726885A
TW201726885A TW105141198A TW105141198A TW201726885A TW 201726885 A TW201726885 A TW 201726885A TW 105141198 A TW105141198 A TW 105141198A TW 105141198 A TW105141198 A TW 105141198A TW 201726885 A TW201726885 A TW 201726885A
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color conversion
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light
formula
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境野裕健
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東麗股份有限公司
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    • C—CHEMISTRY; METALLURGY
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
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    • G02B5/00—Optical elements other than lenses
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    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
    • H01L33/50—Wavelength conversion elements

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Abstract

A color conversion composition that is one aspect of the present invention contains component (A), component (B) and component (C), and converts incident light into light having a longer wavelength than the incident light. This color conversion composition and a color conversion film containing same can be used in a light source unit, a display and a lighting system. Component (A): at least one type of organic light-emitting material. Component (B): a binder resin. Component (C): an amine derivative having a partial structure represented by general formula (1) (R10 to R14 may be the same as, or different from, each other, and are selected from among hydrogen atoms, alkyl groups, cycloalkyl groups, aryl groups and heteroaryl groups. However, at least one of R11 and R12 and at least one of R13 and R14 are not hydrogen atoms).

Description

色變換組成物、色變換膜、含有其的光源單元、顯示器及照明裝置Color conversion composition, color conversion film, light source unit including the same, display and illumination device

本發明是有關於一種色變換組成物、色變換膜、含有其的光源單元、顯示器及照明裝置。The present invention relates to a color conversion composition, a color conversion film, a light source unit including the same, a display, and a lighting device.

將利用色變換方式的多色化技術應用於液晶顯示器或有機電致發光（Electroluminescence，EL）顯示器、照明裝置等正得到積極研究。所謂色變換，是指將來自發光體的發光變換成波長更長的光，例如表示將藍色發光變換成綠色發光或紅色發光。將具有該色變換功能的組成物（以下，稱為「色變換組成物」）加以膜化，並與例如藍色光源進行組合，藉此可自藍色光源取出藍色、綠色、紅色的3原色，即可取出白色光。將此種使藍色光源與具有色變換功能的膜（以下，稱為「色變換膜」）組合而成的白色光源作為背光單元，並將該背光單元與液晶驅動部分及彩色濾光片加以組合，藉此可製作全彩顯示器。另外，若無液晶驅動部分，則可直接用作白色光源，例如可用作發光二極體（Light Emitting Diode，LED）照明等的白色光源。It is actively being studied to apply a multi-coloring technique using a color conversion method to a liquid crystal display, an organic electroluminescence (EL) display, a lighting device, and the like. The color conversion means converting light from the illuminant into light having a longer wavelength, and for example, converting blue luminescence into green luminescence or red luminescence. A composition having the color conversion function (hereinafter referred to as a "color conversion composition") is formed into a film and combined with, for example, a blue light source, whereby blue, green, and red colors can be taken out from the blue light source. The primary color can be used to remove white light. A white light source in which a blue light source and a film having a color conversion function (hereinafter referred to as a "color conversion film") are combined is used as a backlight unit, and the backlight unit, the liquid crystal driving portion, and the color filter are applied. Combine to create a full color display. In addition, if there is no liquid crystal driving portion, it can be directly used as a white light source, for example, a white light source that can be used as a light emitting diode (LED) illumination or the like.

作為利用色變換方式的液晶顯示器的課題，可列舉色彩再現性的提昇。對於提昇色彩再現性，有效的是減小背光單元的藍色、綠色、紅色的各發光光譜的半寬度，並提高藍色、綠色、紅色各色的色純度。As a subject of a liquid crystal display using a color conversion method, improvement in color reproducibility can be cited. For improving color reproducibility, it is effective to reduce the half width of each of the blue, green, and red light-emitting spectra of the backlight unit, and to improve the color purity of each of the blue, green, and red colors.

作為解決該課題的方法，提出有將由無機半導體微粒子所形成的量子點用作色變換組成物的成分的技術（例如，參照專利文獻1）。使用量子點的技術確實綠色、紅色的發光光譜的半寬度狹小，色彩再現性提昇，但量子點不耐熱、空氣中的水分或氧，耐久性並不充分。另外，亦存在含有鎘等課題。As a method for solving this problem, a technique in which a quantum dot formed of inorganic semiconductor fine particles is used as a component of a color conversion composition has been proposed (for example, see Patent Document 1). The technique using quantum dots does have a narrow half-width of the green and red luminescence spectrum, and the color reproducibility is improved, but the quantum dots are not heat-resistant, moisture or oxygen in the air, and durability is not sufficient. In addition, there are also problems such as the inclusion of cadmium.

另外，亦提出有將有機物的發光材料代替量子點來用作色變換組成物的成分的技術。作為將有機發光材料用作色變換組成物的成分的技術的例子，揭示有使用香豆素衍生物者（例如，參照專利文獻2）、使用羅丹明衍生物者（例如，參照專利文獻3）、使用吡咯亞甲基衍生物者（例如，參照專利文獻4）。另外，亦提出有為了防止有機發光材料的劣化、提昇耐久性而添加光穩定劑的技術（例如，參照專利文獻5）。 現有技術文獻 專利文獻Further, a technique of using a luminescent material of an organic substance instead of a quantum dot as a component of a color conversion composition has also been proposed. As an example of a technique of using an organic light-emitting material as a component of a color conversion composition, those who use a coumarin derivative (for example, refer to Patent Document 2) and use a rhodamine derivative (for example, refer to Patent Document 3) A pyrromethylene derivative is used (for example, refer to Patent Document 4). In addition, a technique of adding a light stabilizer to prevent deterioration of the organic light-emitting material and to improve durability has been proposed (for example, refer to Patent Document 5). Prior art literature

專利文獻1：日本專利特開2012-22028號公報 專利文獻2：日本專利特開2007-273440號公報 專利文獻3：日本專利特開2001-164245號公報 專利文獻4：日本專利特開2011-241160號公報 專利文獻5：國際公開第2011/149028號Patent Document 1: Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Patent Document 5: International Publication No. 2011/149028

[發明所欲解決之課題] 但是，即便使用該些有機發光材料或光穩定劑，就色彩再現性與耐久性併存這一觀點而言，仍不充分。[Problems to be Solved by the Invention] However, even if these organic light-emitting materials or light stabilizers are used, it is still insufficient from the viewpoint of coexistence of color reproducibility and durability.

例如，於專利文獻5中揭示有藉由將單重態氧加以鈍化來提昇耐久性的技術，但對於單重態氧以外的劣化因素未實施明確的解決方案，因此，耐久性並不充分。進而，專利文獻5中所記載的光穩定劑於可見區域中具有比較強的吸收，因此會吸收發光材料的發光，故存在發光效率下降這一問題。For example, Patent Document 5 discloses a technique for improving durability by passivating singlet oxygen. However, a clear solution has not been made for deterioration factors other than singlet oxygen, and therefore, durability is not sufficient. Further, since the light stabilizer described in Patent Document 5 has relatively strong absorption in the visible region, it absorbs the light emission of the light-emitting material, so that there is a problem that the light-emitting efficiency is lowered.

如此，將可使高色純度（色彩再現性的提昇）與高耐久性併存的有機發光材料用作色變換組成物的成分的技術仍不充分。Thus, the technique of using an organic light-emitting material having high color purity (increased color reproducibility) and high durability as a component of a color conversion composition is still insufficient.

本發明欲解決的課題是於液晶顯示器等顯示器或LED照明等照明裝置中所使用的色變換組成物中，使色彩再現性的提昇與高耐久性併存，尤其使高色純度的發光與高耐久性併存。 [解決課題之手段]The problem to be solved by the present invention is to enhance the color reproducibility and high durability in a color conversion composition used in a display device such as a liquid crystal display or an illumination device such as LED illumination, in particular, high-color purity illumination and high durability. Sexual coexistence. [Means for solving the problem]

本發明者查明藉由光照射而產生的自由基會引起有機發光材料的劣化。而且，發現藉由將特定的物質用作色變換組成物的成分，可使所生成的自由基鈍化，並提昇有機發光材料的耐久性。The inventors have found that radicals generated by light irradiation cause deterioration of the organic light-emitting material. Moreover, it has been found that by using a specific substance as a component of the color conversion composition, the generated radical can be passivated and the durability of the organic light-emitting material can be improved.

即，為解決所述課題，並達成目的，本發明的色變換組成物是將入射光變換成波長比該入射光長的光的色變換組成物，其特徵在於：包括以下的（A）成分、（B）成分及（C）成分。 （A）成分：至少一種的有機發光材料 （B）成分：黏合劑樹脂 （C）成分：具有由通式（1）所表示的部分結構的胺衍生物In order to solve the above problems, and to achieve the object, the color conversion composition of the present invention is a color conversion composition that converts incident light into light having a longer wavelength than the incident light, and includes the following component (A). , (B) component and (C) component. (A) component: at least one organic light-emitting material (B) component: binder resin (C) component: an amine derivative having a partial structure represented by the general formula (1)

[化1]（R10 ～R14 分別可相同，亦可不同，且自氫原子、烷基、環烷基、芳基、雜芳基中選擇。其中，R11 與R12 的至少一者及R13 與R14 的至少一者不為氫原子）[Chemical 1] (R 10 to R 14 may be the same or different, and may be selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group. Among them, at least one of R 11 and R 12 and R 13 and At least one of R 14 is not a hydrogen atom)

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述（C）成分為具有由通式（2）所表示的哌啶骨架的化合物。Further, in the invention, the color conversion composition of the invention is characterized in that the component (C) is a compound having a piperidine skeleton represented by the formula (2).

[化2]（R10 ～R14 與所述通式（1）相同）[Chemical 2] (R 10 to R 14 are the same as the above formula (1))

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述（C）成分為由通式（3）所表示的化合物。Further, in the invention, the color conversion composition of the invention is characterized in that the component (C) is a compound represented by the formula (3).

[化3]（R10 ～R14 與所述通式（1）相同。m為10以下的自然數。Y自單鍵、鏈狀或環狀的脂肪族烴、脂肪族雜環、芳香族烴環、芳香族雜環、或該些的組合中選擇）[Chemical 3] (R 10 to R 14 are the same as those of the above formula (1). m is a natural number of 10 or less. Y is a single bond, a chain or a cyclic aliphatic hydrocarbon, an aliphatic heterocyclic ring, an aromatic hydrocarbon ring, or a fragrance. Family heterocycle, or a combination of these)

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述通式（3）的Y為鏈狀或環狀的脂肪族烴、苯環、或該些的組合。Further, in the invention, the color conversion composition of the present invention is characterized in that Y of the above formula (3) is a chain or cyclic aliphatic hydrocarbon, a benzene ring, or a combination thereof.

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述R10 為烷基。Further, in the invention, the color conversion composition of the invention is characterized in that the R 10 is an alkyl group.

另外，於所述發明中，本發明的色變換組成物的特徵在於：相對於所述（B）成分的100重量份，所述（C）成分的含量為1.0×10-2 重量份以上、10重量份以下。Further, in the invention, the color conversion composition of the present invention is characterized in that the content of the component (C) is 1.0 × 10 -2 parts by weight or more based on 100 parts by weight of the component (B). 10 parts by weight or less.

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述（A）成分含有由通式（4）所表示的化合物。Further, in the invention, the color conversion composition of the present invention is characterized in that the component (A) contains a compound represented by the formula (4).

[化4]（X為C-R7 或N。R1 ～R9 分別可相同，亦可不同，自氫、烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基、及與鄰接取代基之間所形成的縮合環及脂肪族環中選擇）[Chemical 4] (X is CR 7 or N. R 1 to R 9 may be the same or different, and may be different from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol. , alkoxy, alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecaraki, amine, nitrate a group selected from the group consisting of a condensed ring and an aliphatic ring formed between a sulfonyl group, a decyloxy group, a boroxyl group, a phosphine oxide group, and an adjacent substituent)

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述通式（4）的X為C-R7 ，所述R7 為由通式（5）所表示的基。Further, in the invention, the color conversion composition of the invention is characterized in that X of the formula (4) is CR 7 and the R 7 is a group represented by the formula (5).

[化5]（r選自由氫、烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基所組成的群組。k為1～3的整數。當k為2以上時，r分別可相同，亦可不同）[Chemical 5] (r is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio, aryl ether, aryl sulfide , aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, amine, mercapto, amine, nitro, decyl, decyl, boro, phosphine The group consisting of k is an integer from 1 to 3. When k is 2 or more, r may be the same or different.

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述通式（4）的R1 、R3 、R4 及R6 分別可相同，亦可不同，且為經取代或未經取代的苯基。Further, in the above invention, the color conversion composition of the present invention is characterized in that R 1 , R 3 , R 4 and R 6 of the above formula (4) are respectively the same, different, and substituted. Or unsubstituted phenyl.

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述通式（4）的R1 、R3 、R4 及R6 分別可相同，亦可不同，且為經取代或未經取代的烷基。Further, in the above invention, the color conversion composition of the present invention is characterized in that R 1 , R 3 , R 4 and R 6 of the above formula (4) are respectively the same, different, and substituted. Or unsubstituted alkyl.

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述（A）成分含有藉由使用波長430 nm以上、500 nm以下的範圍的激發光，而呈現於峰值波長為500 nm以上、580 nm以下的區域中所觀測到的發光的發光材料。Further, in the invention described above, the color conversion composition of the present invention is characterized in that the component (A) is contained at a peak wavelength of 500 by using excitation light having a wavelength of 430 nm or more and 500 nm or less. A luminescent material that is observed in a region above nm and below 580 nm.

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述（A）成分含有以下的發光材料（a）及發光材料（b）。 發光材料（a）：藉由使用波長430 nm以上、500 nm以下的範圍的激發光，而呈現於峰值波長為500 nm以上、580 nm以下的區域中所觀測到的發光的發光材料 發光材料（b）：藉由波長430 nm以上，500 nm以下的範圍的激發光及來自所述發光材料（a）的發光的至少一者而得到激發，藉此呈現於峰值波長為580 nm以上、750 nm以下的區域中所觀測到的發光的發光材料Further, in the invention, the color conversion composition of the present invention is characterized in that the component (A) contains the following luminescent material (a) and luminescent material (b). Luminescent material (a): a luminescent material luminescent material which is observed in a region having a peak wavelength of 500 nm or more and 580 nm or less by using excitation light having a wavelength of 430 nm or more and 500 nm or less ( b): excitation is performed by at least one of excitation light having a wavelength of 430 nm or more and 500 nm or less and luminescence from the luminescent material (a), thereby exhibiting a peak wavelength of 580 nm or more and 750 nm. Luminescent luminescent materials observed in the following regions

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述發光材料（a）的含量wa 與所述發光材料（b）的含量wb 為wa ≧wb 的關係。Further, in the invention, the color conversion composition of the present invention is characterized in that the content w a of the luminescent material (a) and the content w b of the luminescent material (b) are w a ≧ w b .

另外，於所述發明中，本發明的色變換組成物的特徵在於：藉由使用波長430 nm以上、500 nm以下的範圍的激發光，而呈現峰值波長為500 nm以上、580 nm以下的發光的所述發光材料為由所述通式（4）所表示的化合物。Further, in the above invention, the color conversion composition of the present invention is characterized in that the excitation light having a wavelength of 430 nm or more and 500 nm or less is used to emit light having a peak wavelength of 500 nm or more and 580 nm or less. The luminescent material is a compound represented by the above formula (4).

另外，於所述發明中，本發明的色變換組成物的特徵在於：所述發光材料（b）為由所述通式（4）所表示的化合物。Further, in the invention, the color conversion composition of the invention is characterized in that the luminescent material (b) is a compound represented by the above formula (4).

另外，本發明的色變換膜的特徵在於：包括所述發明的任一者中所記載的色變換組成物的硬化物層。Further, the color conversion film of the present invention is characterized by comprising a cured layer of the color conversion composition described in any one of the inventions.

另外，本發明的光源單元的特徵在於：包括光源及所述發明中所記載的色變換膜。Further, the light source unit of the present invention is characterized by comprising a light source and the color conversion film described in the invention.

另外，於所述發明中，本發明的光源單元的特徵在於：所述光源為於波長430 nm以上、500 nm以下的範圍內具有最大發光的發光二極體。Further, in the above invention, the light source unit of the present invention is characterized in that the light source is a light-emitting diode having maximum light emission in a wavelength range of 430 nm or more and 500 nm or less.

另外，本發明的顯示器的特徵在於：包括所述發明的任一者中所記載的光源單元。Further, the display of the present invention is characterized by comprising the light source unit described in any one of the inventions.

另外，本發明的照明裝置的特徵在於：包括所述發明的任一者中所記載的光源單元。 [發明的效果]Further, the illumination device of the present invention is characterized by comprising the light source unit described in any one of the inventions. [Effects of the Invention]

本發明的色變換組成物及使用其的色變換膜因使高色純度的發光與高耐久性併存，故取得可使色彩再現性的提昇與高耐久性併存這一效果。本發明的光源單元、顯示器及照明裝置因使用此種色變換膜，故取得可使色彩再現性的提昇與高耐久性併存這一效果。In the color conversion composition of the present invention and the color conversion film using the same, high-color purity luminescence and high durability are coexistence, so that the effect of improving color reproducibility and high durability can be obtained. Since the light source unit, the display, and the illumination device of the present invention use such a color conversion film, it is possible to achieve an effect of improving color reproducibility and high durability.

以下，對本發明的色變換組成物、色變換膜、含有其的光源單元、顯示器及照明裝置的適宜的實施形態進行具體說明，但本發明並不限定於以下的實施形態，可對應於目的或用途而進行各種變更後實施。Hereinafter, a preferred embodiment of the color conversion composition, the color conversion film, the light source unit including the same, the display, and the illumination device of the present invention will be specifically described. However, the present invention is not limited to the following embodiments and may correspond to the purpose or It is implemented after various changes have been made for use.

＜色變換組成物＞ 本發明的實施形態的色變換組成物是將來自光源等發光體的入射光變換成波長比該入射光長的光者，且至少含有（A）成分、（B）成分及（C）成分。於本發明中，（A）成分為至少一種的有機發光材料。（B）成分為黏合劑樹脂。（C）成分為於分子結構中具有由通式（1）所表示的部分結構的胺衍生物。<Color conversion composition> The color conversion composition according to the embodiment of the present invention converts incident light from a light source such as a light source into light having a longer wavelength than the incident light, and contains at least (A) component and (B) component. And (C) ingredients. In the present invention, the component (A) is at least one organic light-emitting material. The component (B) is a binder resin. The component (C) is an amine derivative having a partial structure represented by the formula (1) in a molecular structure.

[化6] [Chemical 6]

通式（1）中，R10 ～R14 分別為選自氫原子、烷基、環烷基、芳基、雜芳基中者。其中，所述R10 ～R14 分別可相同，亦可不同。另外，R11 與R12 的至少一者及R13 與R14 的至少一者不為氫原子。In the formula (1), R 10 to R 14 are each selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group and a heteroaryl group. The R 10 to R 14 may be the same or different. Further, at least one of R 11 and R 12 and at least one of R 13 and R 14 are not a hydrogen atom.

＜（A）成分：有機發光材料＞ 本發明的實施形態的色變換組成物含有至少一種有機發光材料作為（A）成分。此處，本發明中的發光材料是指當照射有某種光時，發出波長與該光不同的光的材料。有機發光材料為有機物的發光材料。<(A) component: organic light-emitting material> The color conversion composition of the embodiment of the present invention contains at least one organic light-emitting material as the component (A). Here, the luminescent material in the present invention means a material that emits light having a wavelength different from the light when a certain kind of light is irradiated. The organic light-emitting material is an organic light-emitting material.

為了達成高效率的色變換，發光材料較佳為顯示出發光量子產率高的發光特性的材料。通常，作為發光材料，可列舉無機螢光體、螢光顏料、螢光染料、量子點等公知的發光材料，但就分散的均勻性、使用量的降低、環境負荷的降低的觀點而言，較佳為有機發光材料。In order to achieve high-efficiency color conversion, the luminescent material is preferably a material exhibiting luminescent properties with high luminescence quantum yield. In general, a known luminescent material such as an inorganic phosphor, a fluorescent pigment, a fluorescent dye, or a quantum dot is used as the luminescent material, but in terms of uniformity of dispersion, reduction in use amount, and reduction in environmental load, It is preferably an organic light-emitting material.

作為有機發光材料，可列舉以下所示者等。例如可列舉萘、蒽、菲、芘、䓛、稠四苯、三伸苯、苝、熒蒽、茀、茚等具有縮合芳基環的化合物或其衍生物等作為適宜的有機發光材料。另外，可列舉呋喃、吡咯、噻吩、噻咯、9-矽茀、9,9'-螺二矽茀、苯并噻吩、苯并呋喃、吲哚、二苯并噻吩、二苯并呋喃、咪唑并吡啶、啡啉、吡啶、吡嗪、萘啶、喹噁啉、吡咯并吡啶等具有雜芳基環的化合物或其衍生物，硼烷衍生物等作為適宜的有機發光材料。Examples of the organic light-emitting material include the following. For example, a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, anthracene, anthracene, fused tetraphenyl, triphenylene, fluorene, fluoranthene, anthracene or anthracene, or a derivative thereof may be mentioned as a suitable organic light-emitting material. Further, there may be mentioned furan, pyrrole, thiophene, thiophene, 9-fluorene, 9,9'-spirobifluorene, benzothiophene, benzofuran, anthracene, dibenzothiophene, dibenzofuran, imidazole And a compound having a heteroaryl ring such as pyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline or pyrrolopyridine or a derivative thereof, a borane derivative or the like is suitable as a suitable organic light-emitting material.

另外，可列舉1,4-二苯乙烯基苯、4,4'-雙(2-(4-二苯基胺基苯基)乙烯基)聯苯、4,4'-雙(N-(二苯乙烯-4-基)-N-苯基胺基)二苯乙烯等二苯乙烯衍生物，芳香族乙炔衍生物，四苯基丁二烯衍生物，醛連氮衍生物，吡咯亞甲基衍生物，二酮吡咯并[3,4-c]吡咯衍生物等作為適宜的有機發光材料。另外，可列舉香豆素6、香豆素7、香豆素153等香豆素衍生物，咪唑、噻唑、噻二唑、咔唑、噁唑、噁二唑、***等唑衍生物及其金屬錯合物，吲哚花青綠等花青系化合物，螢光素、曙紅、羅丹明等呫噸系化合物或噻噸系化合物等作為適宜的有機發光材料。Further, examples thereof include 1,4-distyrylbenzene, 4,4'-bis(2-(4-diphenylaminophenyl)vinyl)biphenyl, and 4,4'-bis(N-( a stilbene derivative such as stilbene-4-yl)-N-phenylamino)stilbene, an aromatic acetylene derivative, a tetraphenylbutadiene derivative, an aldehyde nitrogen derivative, pyrrole A base derivative, a diketopyrrolo[3,4-c]pyrrole derivative or the like is suitable as a suitable organic light-emitting material. Further, examples thereof include coumarin derivatives such as coumarin 6, coumarin 7, and coumarin 153, and azole derivatives such as imidazole, thiazole, thiadiazole, oxazole, oxazole, oxadiazole, and triazole. A metal complex, a cyanine compound such as phthalocyanine, a xanthene compound such as fluorescein, eosin, or rhodamine, or a thioxan compound is used as a suitable organic light-emitting material.

另外，可列舉聚伸苯基系化合物、萘二甲醯亞胺衍生物、酞菁衍生物及其金屬錯合物、卟啉衍生物及其金屬錯合物、尼羅紅或尼羅藍等噁嗪系化合物、螺烯系化合物、N,N'-二苯基-N,N'-二(3-甲基苯基)-4,4'-二苯基-1,1'-二胺等芳香族胺衍生物等作為適宜的有機發光材料。另外，可列舉銥（Ir）、釕（Ru）、銠（Rh）、鈀（Pd）、鉑（Pt）、鋨（Os）及錸（Re）等的有機金屬錯化合物等作為適宜的有機發光材料。但是，本發明中的有機發光材料並不限定於所述的有機發光材料。Further, examples thereof include a polyphenylene compound, a naphthylimine derivative, a phthalocyanine derivative and a metal complex thereof, a porphyrin derivative and a metal complex thereof, Nile Red or Nile Blue, and the like. Oxazine-based compound, spiroene compound, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine An aromatic amine derivative or the like is used as a suitable organic light-emitting material. Further, as the suitable organic light-emitting, an organometallic compound such as iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os) or ruthenium (Re) may be mentioned. material. However, the organic light-emitting material in the present invention is not limited to the organic light-emitting material described above.

有機發光材料可為螢光發光材料，亦可為磷光發光材料，但為了達成高色純度，較佳為螢光發光材料。該些之中，就熱穩定性及光穩定性高而言，較佳為具有縮合芳基環的化合物或其衍生物。The organic light-emitting material may be a fluorescent material or a phosphorescent material, but in order to achieve high color purity, a fluorescent material is preferred. Among these, in terms of high thermal stability and high photostability, a compound having a condensed aryl ring or a derivative thereof is preferred.

另外，作為有機發光材料，就溶解性或分子結構的多樣性的觀點而言，較佳為具有配位鍵的化合物。就半寬度小、可進行高效率的發光的觀點而言，氟化硼錯合物等含有硼的化合物亦較佳。其中，就提供高發光量子產率、且耐久性良好的觀點而言，較佳為吡咯亞甲基衍生物。更佳為由通式（4）所表示的化合物，即吡咯亞甲基化合物。Further, as the organic light-emitting material, a compound having a coordinate bond is preferred from the viewpoint of solubility or molecular structure diversity. From the viewpoint of having a small half width and efficient light emission, a boron-containing compound such as a boron fluoride complex is also preferable. Among them, a pyrrolethymethylene derivative is preferred from the viewpoint of providing high luminescence quantum yield and good durability. More preferably, it is a compound represented by the formula (4), that is, a pyrrolemethylene compound.

[化7] [Chemistry 7]

當（A）成分含有由通式（4）所表示的化合物作為有機發光材料時，於通式（4）中，X為C-R7 或N。R1 ～R9 分別可相同，亦可不同，自氫、烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基、及與鄰接取代基之間所形成的縮合環及脂肪族環中選擇。When the component (A) contains a compound represented by the formula (4) as an organic light-emitting material, in the formula (4), X is CR 7 or N. R 1 to R 9 may be the same or different, and may be different from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio. , aryl ether group, aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, amine methyl group, amine group, nitro group, decyl group, decane oxide The group is selected from the group consisting of a condensed ring and an aliphatic ring formed between a oxyboron group, a phosphine oxide group, and an adjacent substituent.

於所述所有基中，氫亦可為氘。於以下所說明的化合物或其部分結構中亦同樣如此。另外，於以下的說明中，例如所謂碳數6～40的經取代或未經取代的芳基，是指亦包含於芳基取代的取代基中所含有的碳數在內的所有碳數變成6～40的芳基。規定碳數的其他取代基亦同樣如此。Hydrogen may also be ruthenium in all of the groups. The same is true for the compounds described below or their partial structures. In the following description, for example, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms means that all carbon numbers including the carbon number contained in the substituent substituted with the aryl group become 6 to 40 aryl groups. The same is true for other substituents that specify the carbon number.

另外，於所述所有基中，作為被取代時的取代基，較佳為烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基，更佳為於各取代基的說明中作為較佳者的具體的取代基。另外，該些取代基亦可由所述取代基進一步取代。Further, among all the groups, as the substituent at the time of substitution, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group or an alkoxy group is preferred. , alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecarboxamidine, amine, nitro, decyl More preferably, it is a preferred substituent in the description of each substituent. Further, the substituents may be further substituted by the substituent.

「經取代或未經取代的」這一情況下的「未經取代」是指取代有氫原子或氘原子。於以下所說明的化合物或其部分結構中，關於「經取代或未經取代的」這一情況，亦與所述相同。"Unsubstituted" in the case of "substituted or unsubstituted" means substituted with a hydrogen atom or a halogen atom. In the case of the compound described below or a partial structure thereof, the case of "substituted or unsubstituted" is also the same as described above.

於所述所有基之中，所謂烷基，例如表示甲基、乙基、正丙基、異丙基、正丁基、第二丁基、第三丁基等飽和脂肪族烴基，其可具有取代基，亦可不具有取代基。經取代時的追加的取代基並無特別限制，例如可列舉烷基、鹵素、芳基、雜芳基等，此點於以下的記載中亦通用。另外，烷基的碳數並無特別限定，但就獲得的容易性或成本的觀點而言，較佳為1以上、20以下，更佳為1以上、8以下的範圍。Among all the groups, the alkyl group, for example, represents a saturated aliphatic hydrocarbon group such as methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl or t-butyl, which may have The substituent may or may not have a substituent. The additional substituent at the time of substitution is not particularly limited, and examples thereof include an alkyl group, a halogen group, an aryl group, and a heteroaryl group, which are also used in the following description. In addition, the number of carbon atoms of the alkyl group is not particularly limited, but from the viewpoint of availability and cost, it is preferably 1 or more and 20 or less, more preferably 1 or more and 8 or less.

所謂環烷基，例如表示環丙基、環己基、降冰片基、金剛烷基等飽和脂環式烴基，其可具有取代基，亦可不具有取代基。烷基部分的碳數並無特別限定，但較佳為3以上、20以下的範圍。The cycloalkyl group means, for example, a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group or an adamantyl group, and may or may not have a substituent. The carbon number of the alkyl moiety is not particularly limited, but is preferably in the range of 3 or more and 20 or less.

所謂雜環基，例如表示吡喃環、哌啶環、環狀醯胺等在環內具有碳以外的原子的脂肪族環，其可具有取代基，亦可不具有取代基。雜環基的碳數並無特別限定，但較佳為2以上、20以下的範圍。The heterocyclic group is, for example, an aliphatic ring having an atom other than carbon in the ring such as a pyran ring, a piperidine ring or a cyclic decylamine, and may have a substituent or may have no substituent. The carbon number of the heterocyclic group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

所謂烯基，例如表示乙烯基、烯丙基、丁二烯基等含有雙鍵的不飽和脂肪族烴基，其可具有取代基，亦可不具有取代基。烯基的碳數並無特別限定，但較佳為2以上、20以下的範圍。The alkenyl group may, for example, represent a double bond-containing unsaturated aliphatic hydrocarbon group such as a vinyl group, an allyl group or a butadienyl group, and may have a substituent or may have no substituent. The carbon number of the alkenyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

所謂環烯基，例如表示環戊烯基、環戊二烯基、環己烯基等含有雙鍵的不飽和脂環式烴基，其可具有取代基，亦可不具有取代基。The cycloalkenyl group may, for example, represent a double bond-containing unsaturated alicyclic hydrocarbon group such as a cyclopentenyl group, a cyclopentadienyl group or a cyclohexenyl group, and may have a substituent or may have no substituent.

所謂炔基，例如表示乙炔基等含有三鍵的不飽和脂肪族烴基，其可具有取代基，亦可不具有取代基。炔基的碳數並無特別限定，但較佳為2以上、20以下的範圍。The alkynyl group is, for example, an unsaturated aliphatic hydrocarbon group having a triple bond such as an ethynyl group, and may have a substituent or may have no substituent. The carbon number of the alkynyl group is not particularly limited, but is preferably in the range of 2 or more and 20 or less.

所謂烷氧基，例如表示甲氧基、乙氧基、丙氧基等經由醚鍵而鍵結有脂肪族烴基的官能基，該脂肪族烴基可具有取代基，亦可不具有取代基。烷氧基的碳數並無特別限定，但較佳為1以上、20以下的範圍。The alkoxy group may, for example, represent a functional group in which an aliphatic hydrocarbon group is bonded via an ether bond such as a methoxy group, an ethoxy group or a propoxy group, and the aliphatic hydrocarbon group may have a substituent or may have no substituent. The carbon number of the alkoxy group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.

所謂烷硫基，是指烷氧基的醚鍵的氧原子被硫原子取代而成者。烷硫基的烴基可具有取代基，亦可不具有取代基。烷硫基的碳數並無特別限定，但較佳為1以上、20以下的範圍。The alkylthio group means that the oxygen atom of the ether bond of the alkoxy group is substituted by a sulfur atom. The alkylthio group may have a substituent or may have no substituent. The carbon number of the alkylthio group is not particularly limited, but is preferably in the range of 1 or more and 20 or less.

所謂芳醚基，例如表示苯氧基等經由醚鍵而鍵結有芳香族烴基的官能基，芳香族烴基可具有取代基，亦可不具有取代基。芳醚基的碳數並無特別限定，但較佳為6以上、40以下的範圍。The aryl ether group is, for example, a functional group in which an aromatic hydrocarbon group is bonded via an ether bond such as a phenoxy group, and the aromatic hydrocarbon group may have a substituent or may have no substituent. The carbon number of the aryl ether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

所謂芳基硫醚基，是指芳醚基的醚鍵的氧原子被硫原子取代而成者。芳基硫醚基中的芳香族烴基可具有取代基，亦可不具有取代基。芳基硫醚基的碳數並無特別限定，但較佳為6以上、40以下的範圍。The aryl sulfide group refers to an oxygen atom of an ether bond of an aryl ether group which is substituted by a sulfur atom. The aromatic hydrocarbon group in the aryl sulfide group may have a substituent or may have no substituent. The carbon number of the aryl sulfide group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.

所謂芳基，例如表示苯基、聯苯基、聯三苯基、萘基、茀基、苯并茀基、二苯并茀基、菲基、蒽基、苯并菲基、苯并蒽基、䓛基、芘基、丙[二]烯合茀基、三亞苯基、苯并丙[二]烯合茀基、二苯并蒽基、苝基、螺烯基等芳香族烴基。其中，較佳為苯基、聯苯基、聯三苯基、萘基、茀基、菲基、蒽基、芘基、丙[二]烯合茀基、三亞苯基。芳基可具有取代基，亦可不具有取代基。芳基的碳數並無特別限定，但較佳為6以上、40以下，更佳為6以上、30以下的範圍。The aryl group means, for example, a phenyl group, a biphenyl group, a triphenylene group, a naphthyl group, an anthracenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, a fluorenyl group, a benzophenanyl group, a benzindenyl group. An aromatic hydrocarbon group such as an anthracenyl group, a fluorenyl group, a propyl [di] olefin group, a triphenylene group, a benzopropane [di] ene fluorenyl group, a dibenzofluorenyl group, a fluorenyl group or a spiroalkenyl group. Among them, a phenyl group, a biphenyl group, a biphenylene group, a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group, a fluorenyl group, a propyl [di] ene fluorenyl group, and a triphenylene group are preferable. The aryl group may have a substituent or may have no substituent. The carbon number of the aryl group is not particularly limited, but is preferably 6 or more and 40 or less, more preferably 6 or more and 30 or less.

當R1 ～R9 為經取代或未經取代的芳基時，作為芳基，較佳為苯基、聯苯基、聯三苯基、萘基、茀基、菲基、蒽基，更佳為苯基、聯苯基、聯三苯基、萘基。進而更佳為苯基、聯苯基、聯三苯基，特佳為苯基。When R 1 to R 9 are a substituted or unsubstituted aryl group, as the aryl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group, and the like are preferable. Preferred is phenyl, biphenyl, terphenyl, naphthyl. Further, it is more preferably a phenyl group, a biphenyl group or a terphenyl group, and particularly preferably a phenyl group.

當各個取代基由芳基進一步取代時，作為芳基，較佳為苯基、聯苯基、聯三苯基、萘基、茀基、菲基、蒽基，更佳為苯基、聯苯基、聯三苯基、萘基。特佳為苯基。When each substituent is further substituted by an aryl group, as the aryl group, a phenyl group, a biphenyl group, a triphenylene group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group, and more preferably a phenyl group or a biphenyl group is preferred. Base, triphenyl, naphthyl. Particularly preferred is phenyl.

所謂雜芳基，例如表示吡啶基、呋喃基、噻吩基、喹啉基、異喹啉基、吡嗪基、嘧啶基、噠嗪基、三嗪基、萘啶基、噌啉基、呔嗪基、喹噁啉基、喹唑啉基、苯并呋喃基、苯并噻吩基、吲哚基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并咔唑基、咔啉基、吲哚咔唑基、苯并呋喃并咔唑基、苯并噻吩并咔唑基、二氫茚并咔唑基、苯并喹啉基、吖啶基、二苯并吖啶基、苯并咪唑基、咪唑并吡啶基、苯并噁唑基、苯并噻唑基、啡啉基等在環內具有一個或多個碳以外的原子的環狀芳香族基。其中，所謂萘啶基，表示1,5-萘啶基、1,6-萘啶基、1,7-萘啶基、1,8-萘啶基、2,6-萘啶基、2,7-萘啶基的任一者。雜芳基可具有取代基，亦可不具有取代基。雜芳基的碳數並無特別限定，但較佳為2以上、40以下，更佳為2以上、30以下的範圍。By heteroaryl, for example, pyridyl, furyl, thienyl, quinolyl, isoquinolinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, naphthyridinyl, porphyrinyl, pyridazine , quinoxaline, quinazolinyl, benzofuranyl, benzothienyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzoxazolyl, porphyrin Base, carbazolyl, benzofuranoxazolyl, benzothienooxazolyl, indanoxazolyl, benzoquinolyl, acridinyl, dibenzoacridinyl, benzene And a cyclic aromatic group having one or more atoms other than carbon in the ring, such as an imidazolyl group, an imidazopyridyl group, a benzoxazolyl group, a benzothiazolyl group, or a morpholino group. Wherein, the naphthyridinyl group means 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 1,8-naphthyridinyl, 2,6-naphthyridinyl, 2, Any of 7-naphthyridinyl. The heteroaryl group may have a substituent or may have no substituent. The carbon number of the heteroaryl group is not particularly limited, but is preferably 2 or more and 40 or less, and more preferably 2 or more and 30 or less.

當R1 ～R9 為經取代或未經取代的雜芳基時，作為雜芳基，較佳為吡啶基、呋喃基、噻吩基、喹啉基、嘧啶基、三嗪基、苯并呋喃基、苯并噻吩基、吲哚基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并咪唑基、咪唑并吡啶基、苯并噁唑基、苯并噻唑基、啡啉基，更佳為吡啶基、呋喃基、噻吩基、喹啉基。特佳為吡啶基。When R 1 to R 9 are a substituted or unsubstituted heteroaryl group, as the heteroaryl group, a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a pyrimidinyl group, a triazinyl group or a benzofuran is preferred. , benzothienyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, phenanthroline More preferably, it is a pyridyl group, a furyl group, a thienyl group, or a quinolyl group. Particularly preferred is a pyridyl group.

當各個取代基由雜芳基進一步取代時，作為雜芳基，較佳為吡啶基、呋喃基、噻吩基、喹啉基、嘧啶基、三嗪基、苯并呋喃基、苯并噻吩基、吲哚基、二苯并呋喃基、二苯并噻吩基、咔唑基、苯并咪唑基、咪唑并吡啶基、苯并噁唑基、苯并噻唑基、啡啉基，更佳為吡啶基、呋喃基、噻吩基、喹啉基。特佳為吡啶基。When each substituent is further substituted by a heteroaryl group, as the heteroaryl group, a pyridyl group, a furyl group, a thienyl group, a quinolyl group, a pyrimidinyl group, a triazinyl group, a benzofuranyl group, a benzothienyl group, Mercapto, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzimidazolyl, imidazopyridyl, benzoxazolyl, benzothiazolyl, morpholinyl, more preferably pyridyl , furyl, thienyl, quinolyl. Particularly preferred is a pyridyl group.

所謂鹵素，表示選自氟、氯、溴及碘中的原子。另外，羰基、羧基、氧羰基、胺甲醯基可具有取代基，亦可不具有取代基。此處，作為取代基，例如可列舉烷基、環烷基、芳基、雜芳基等，該些取代基可被進一步取代。The halogen means an atom selected from the group consisting of fluorine, chlorine, bromine and iodine. Further, the carbonyl group, the carboxyl group, the oxycarbonyl group or the aminecarbamyl group may have a substituent or may have no substituent. Here, examples of the substituent include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these substituents may be further substituted.

所謂胺基，是指經取代或未經取代的胺基。胺基可具有取代基，亦可不具有取代基，作為進行取代時的取代基，例如可列舉：芳基、雜芳基、直鏈烷基、分支烷基等。作為芳基、雜芳基，較佳為苯基、萘基、吡啶基、喹啉基。該些取代基可被進一步取代。碳數並無特別限定，但較佳為2以上、50以下，更佳為6以上、40以下，特佳為6以上、30以下的範圍。By amine group is meant a substituted or unsubstituted amine group. The amine group may have a substituent or may have no substituent, and examples of the substituent at the time of substitution include an aryl group, a heteroaryl group, a linear alkyl group, and a branched alkyl group. The aryl group and the heteroaryl group are preferably a phenyl group, a naphthyl group, a pyridyl group or a quinolyl group. These substituents may be further substituted. The number of carbon atoms is not particularly limited, but is preferably 2 or more and 50 or less, more preferably 6 or more and 40 or less, and particularly preferably 6 or more and 30 or less.

所謂矽烷基，例如表示三甲基矽烷基、三乙基矽烷基、第三丁基二甲基矽烷基、丙基二甲基矽烷基、乙烯基二甲基矽烷基等烷基矽烷基，或苯基二甲基矽烷基、第三丁基二苯基矽烷基、三苯基矽烷基、三萘基矽烷基等芳基矽烷基。矽上的取代基可被進一步取代。矽烷基的碳數並無特別限定，但較佳為1以上、30以下的範圍。The alkylene group, for example, represents an alkylalkyl group such as a trimethylsulfanyl group, a triethylsulfanyl group, a tert-butyldimethylsilyl group, a propyldimethylmethylalkyl group or a vinyldimethylalkylene group, or An arylalkylalkyl group such as phenyldimethylmethylalkyl, tert-butyldiphenylalkyl, triphenylsulfanyl or trinaphthylalkyl. The substituent on the oxime can be further substituted. The carbon number of the decyl group is not particularly limited, but is preferably in the range of 1 or more and 30 or less.

所謂矽氧烷基，例如表示三甲基矽氧烷基等經由醚鍵的矽化合物基。矽上的取代基可被進一步取代。另外，所謂氧硼基，是指經取代或未經取代的氧硼基。氧硼基可具有取代基，亦可不具有取代基，作為進行取代時的取代基，例如可列舉：芳基、雜芳基、直鏈烷基、分支烷基、芳醚基、烷氧基、羥基等。其中，較佳為芳基、芳醚基。另外，所謂氧化膦基，是指由-P(=O)R10 R11 所表示的基。R10 R11 自與R1 ～R9 相同的群組中選擇。The oxime group is, for example, a fluorene compound group via an ether bond such as a trimethylphosphonium group. The substituent on the oxime can be further substituted. Further, the term "oxyboron group" means a substituted or unsubstituted oxygen boron group. The oxyboron group may have a substituent or may have no substituent, and examples of the substituent at the time of substitution include an aryl group, a heteroaryl group, a linear alkyl group, a branched alkyl group, an aryl ether group, and an alkoxy group. Hydroxyl and the like. Among them, an aryl group or an aryl ether group is preferred. Further, the phosphine oxide group means a group represented by -P(=O)R 10 R 11 . R 10 R 11 is selected from the same group as R 1 to R 9 .

所謂與鄰接取代基之間所形成的縮合環及脂肪族環，是指任意的鄰接的2個取代基（例如通式（4）的R1 與R2 ）相互鍵結，形成共軛或非共軛的環狀骨架。作為此種縮合環及脂肪族環的構成元素，除碳以外，亦可含有選自氮、氧、硫、磷及矽中的元素。另外，該些縮合環及脂肪族環可進一步與其他環進行縮合。The condensed ring and the aliphatic ring formed between the adjacent substituents mean that any two adjacent substituents (for example, R 1 and R 2 of the general formula (4) are bonded to each other to form a conjugate or a non- Conjugated circular skeleton. The constituent elements of such a condensed ring and an aliphatic ring may contain, in addition to carbon, an element selected from the group consisting of nitrogen, oxygen, sulfur, phosphorus, and antimony. Further, the condensed rings and the aliphatic ring may be further condensed with other rings.

由通式（4）所表示的化合物顯示出高發光量子產率、且發光光譜的半寬度小，因此可達成高效率的色變換與高色純度兩者。進而，由通式（4）所表示的化合物藉由將適當的取代基導入至適當的位置上，可調整發光效率、色純度、熱穩定性、光穩定性及分散性等各種特性或物性。例如，與R1 、R3 、R4 及R6 均為氫的情況相比，R1 、R3 、R4 及R6 的至少1個為經取代或未經取代的烷基或者經取代或未經取代的芳基、經取代或未經取代的雜芳基的情況顯示出更良好的熱穩定性及光穩定性。The compound represented by the formula (4) exhibits a high luminescence quantum yield and a small half width of the luminescence spectrum, so that both high-efficiency color conversion and high color purity can be achieved. Further, the compound represented by the formula (4) can be adjusted to various properties or physical properties such as luminous efficiency, color purity, thermal stability, photostability, and dispersibility by introducing an appropriate substituent into an appropriate position. For example, at least one of R 1 , R 3 , R 4 and R 6 is a substituted or unsubstituted alkyl group or substituted as compared with the case where R 1 , R 3 , R 4 and R 6 are both hydrogen. The case of an unsubstituted aryl group, a substituted or unsubstituted heteroaryl group shows better thermal stability and light stability.

當R1 、R3 、R4 及R6 的至少1個為經取代或未經取代的烷基時，作為烷基，較佳為甲基、乙基、正丙基、異丙基、正丁基、第二丁基、第三丁基、戊基、己基等碳數1～6的烷基。進而，作為該烷基，就熱穩定性優異這一觀點而言，較佳為甲基、乙基、正丙基、異丙基、正丁基、第二丁基、第三丁基。另外，就防止濃度淬滅、提昇發光量子產率這一觀點而言，作為該烷基，更佳為立體體積大的第三丁基。另外，就合成的容易性、原料獲得的容易性這一觀點而言，作為該烷基，亦可較佳地使用甲基。When at least one of R 1 , R 3 , R 4 and R 6 is a substituted or unsubstituted alkyl group, as the alkyl group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, and a positive group are preferable. An alkyl group having 1 to 6 carbon atoms such as a butyl group, a second butyl group, a tert-butyl group, a pentyl group or a hexyl group. Further, the alkyl group is preferably a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, a second butyl group or a third butyl group from the viewpoint of excellent thermal stability. Further, from the viewpoint of preventing concentration quenching and improving luminescence quantum yield, the alkyl group is more preferably a tributyl group having a large steric bulk. Further, from the viewpoint of easiness of synthesis and easiness of obtaining raw materials, a methyl group can be preferably used as the alkyl group.

當R1 、R3 、R4 及R6 的至少1個為經取代或未經取代的芳基時，作為芳基，較佳為苯基、聯苯基、聯三苯基、萘基，更佳為苯基、聯苯基。特佳為苯基。When at least one of R 1 , R 3 , R 4 and R 6 is a substituted or unsubstituted aryl group, as the aryl group, a phenyl group, a biphenyl group, a triphenylene group, a naphthyl group is preferable. More preferably, it is a phenyl group or a biphenyl group. Particularly preferred is phenyl.

當R1 、R3 、R4 及R6 的至少1個為經取代或未經取代的雜芳基時，作為雜芳基，較佳為吡啶基、喹啉基、噻吩基，更佳為吡啶基、喹啉基。特佳為吡啶基。When at least one of R 1 , R 3 , R 4 and R 6 is a substituted or unsubstituted heteroaryl group, the heteroaryl group is preferably a pyridyl group, a quinolyl group or a thienyl group, more preferably Pyridyl, quinolyl. Particularly preferred is a pyridyl group.

當R1 、R3 、R4 及R6 均分別可相同，亦可不同，且為經取代或未經取代的烷基時，對於黏合劑樹脂或溶媒的溶解性良好，故較佳。於此情況下，作為烷基，就合成的容易性、原料獲得的容易性這一觀點而言，較佳為甲基。When R 1 , R 3 , R 4 and R 6 are each the same or different and are substituted or unsubstituted alkyl groups, the solubility in the binder resin or the solvent is good, which is preferable. In this case, the alkyl group is preferably a methyl group from the viewpoint of easiness of synthesis and easiness of obtaining a raw material.

當R1 、R3 、R4 及R6 均分別可相同，亦可不同，且為經取代或未經取代的芳基或者經取代或未經取代的雜芳基時，顯示出更良好的熱穩定性及光穩定性，故較佳。於此情況下，更佳為R1 、R3 、R4 及R6 均分別可相同，亦可不同，且為經取代或未經取代的芳基。When R 1 , R 3 , R 4 and R 6 are each the same or different, and are substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, they show better. Thermal stability and light stability are preferred. In this case, it is more preferred that each of R 1 , R 3 , R 4 and R 6 may be the same or different and is a substituted or unsubstituted aryl group.

亦有提昇多種性質的取代基，但於所有性質方面顯示出充分的性能的取代基有限。尤其，難以使高發光效率與高色純度併存。因此，藉由對由通式（4）所表示的化合物導入多種取代基，可獲得發光特性或色純度等取得平衡的化合物。There are also substituents that enhance a variety of properties, but the substituents that exhibit sufficient performance in all properties are limited. In particular, it is difficult to coexist with high luminous efficiency and high color purity. Therefore, by introducing a plurality of substituents to the compound represented by the formula (4), a compound having a balance between luminescent properties and color purity can be obtained.

尤其，當R1 、R3 、R4 及R6 均分別可相同，亦可不同，且為經取代或未經取代的芳基時，較佳為例如如R1 ≠R4 、R3 ≠R6 、R1 ≠R3 或R4 ≠R6 等般，導入多種取代基。此處，「≠」表示不同的結構的基。例如，R1 ≠R4 表示R1 與R4 為不同的結構的基。藉由如所述般導入多種取代基，可同時導入對色純度造成影響的芳基與對發光效率造成影響的芳基，因此可進行細微的調節。In particular, when R 1 , R 3 , R 4 and R 6 are each the same or different and are substituted or unsubstituted aryl groups, it is preferably, for example, R 1 ≠R 4 , R 3 ≠ A variety of substituents are introduced as in R 6 , R 1 ≠R 3 or R 4 ≠R 6 . Here, "≠" indicates the basis of a different structure. For example, R 1 ≠R 4 represents a group in which R 1 and R 4 are different structures. By introducing a plurality of substituents as described above, an aryl group which affects the color purity and an aryl group which affects the light-emitting efficiency can be simultaneously introduced, and thus fine adjustment can be performed.

其中，就平衡性良好地提昇發光效率與色純度這一觀點而言，較佳為R1 ≠R3 或R4 ≠R6 。於此情況下，針對由通式（4）所表示的化合物，可於兩側的吡咯環上分別導入1個以上的對色純度造成影響的芳基，並於其以外的位置上導入對發光效率造成影響的芳基，因此可最大限度地提昇所述兩種性質。另外，當R1 ≠R3 或R4 ≠R6 時，就提昇耐熱性與色純度兩者這一觀點而言，更佳為R1 ＝R4 及R3 ＝R6 。Among them, R 1 ≠R 3 or R 4 ≠R 6 is preferable from the viewpoint of improving the luminous efficiency and the color purity in a well-balanced manner. In this case, for the compound represented by the formula (4), one or more aryl groups which affect the color purity can be introduced into the pyrrole ring on both sides, and the luminescent group can be introduced at a position other than the aryl group. The efficiency affects the aryl group, thus maximizing the two properties. Further, when R 1 ≠R 3 or R 4 ≠R 6 , from the viewpoint of improving both heat resistance and color purity, R 1 = R 4 and R 3 = R 6 are more preferable.

作為主要對色純度造成影響的芳基，較佳為經供電子性基取代的芳基。所謂供電子性基，於有機電子論中，是指藉由誘導效應或共振效應，對經取代的原子團提供電子的原子團。作為供電子性基，可列舉採用負的值作為哈米特方程（hammett equation）的取代基常數（σp（對位））者。哈米特方程的取代基常數（σp（對位））可自化學便覽基礎篇修訂5版（II-380頁）中引用。As the aryl group which mainly affects the color purity, an aryl group substituted with an electron-donating group is preferred. The electron donating group, in organic electron theory, refers to an atomic group that supplies electrons to a substituted atomic group by an inductive effect or a resonance effect. As the electron-donating group, a negative value is used as a substituent constant (σp (para)) of the Hammett equation. The substituent constant (σp (para)) of the Hammett equation can be quoted from the Chemical Review Basics Revision 5 (page II-380).

作為供電子性基的具體例，例如可列舉：烷基（甲基的σp：-0.17）或烷氧基（甲氧基的σp：-0.27）、胺基（-NH2 的σp：-0.66）等。尤其，較佳為碳數1～8的烷基或碳數1～8的烷氧基，更佳為甲基、乙基、第三丁基、甲氧基。就分散性的觀點而言，特佳為第三丁基、甲氧基，當將該些基作為所述供電子性基時，於由通式（4）所表示的化合物中，可防止由分子彼此的凝聚所引起的淬滅。取代基的取代位置並無特別限定，但為了提高由通式（4）所表示的化合物的光穩定性，必須抑制鍵結的扭曲，因此較佳為相對於與吡咯亞甲基骨架的鍵結位置而鍵結於間位或對位上。另一方面，作為主要對發光效率造成影響的芳基，較佳為具有第三丁基、金剛烷基、甲氧基等體積大的取代基的芳基。Specific examples of the electron-donating group include an alkyl group (σp: -0.17 of methyl group) or an alkoxy group (σp: -0.27 of methoxy group), and an amine group (σp: -0.66 of -NH 2 ) )Wait. In particular, an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms is preferred, and a methyl group, an ethyl group, a third butyl group or a methoxy group is more preferred. From the viewpoint of dispersibility, it is particularly preferably a tert-butyl group or a methoxy group, and when these groups are used as the electron-donating group, in the compound represented by the formula (4), it is possible to prevent Quenching caused by the agglomeration of molecules with each other. The substitution position of the substituent is not particularly limited, but in order to improve the photostability of the compound represented by the general formula (4), it is necessary to suppress the distortion of the bond, and therefore it is preferably bonded to the pyrroxyl skeleton. Position and bond to the meta or alignment. On the other hand, as the aryl group which mainly affects the luminous efficiency, an aryl group having a bulky substituent such as a third butyl group, an adamantyl group or a methoxy group is preferable.

當R1 、R3 、R4 及R6 分別可相同，亦可不同，且為經取代或未經取代的芳基時，較佳為R1 、R3 、R4 及R6 分別可相同，亦可不同，且為經取代或未經取代的苯基。此時，R1 、R3 、R4 及R6 更佳為分別自以下的Ar-1～Ar-6中選擇。於此情況下，作為R1 、R3 、R4 及R6 的較佳的組合，可列舉如表1-1～表1-11中所示的組合，但並不限定於該些組合。When R 1 , R 3 , R 4 and R 6 are respectively the same or different and are substituted or unsubstituted aryl groups, preferably R 1 , R 3 , R 4 and R 6 are respectively the same. It may also be different and is a substituted or unsubstituted phenyl group. In this case, R 1 , R 3 , R 4 and R 6 are more preferably selected from the following Ar-1 to Ar-6. In this case, as a preferable combination of R 1 , R 3 , R 4 and R 6 , the combination shown in Table 1-1 to Table 1-11 can be mentioned, but it is not limited to these combinations.

[化8] [化8]

[表1-1] [Table 1-1]

[表1-2] [Table 1-2]

[表1-3] [Table 1-3]

[表1-4] [Table 1-4]

[表1-5] [Table 1-5]

[表1-6] [Table 1-6]

[表1-7] [Table 1-7]

[表1-8] [Table 1-8]

[表1-9] [Table 1-9]

[表1-10] [Table 1-10]

[表1-11] [Table 1-11]

R2 及R5 較佳為氫、烷基、羰基、氧羰基、芳基的任一者。其中，就熱穩定性的觀點而言，較佳為氫或烷基，就於發光光譜中容易獲得狹小的半寬度這一觀點而言，更佳為氫。R 2 and R 5 are preferably any of hydrogen, an alkyl group, a carbonyl group, an oxycarbonyl group, and an aryl group. Among them, from the viewpoint of thermal stability, hydrogen or an alkyl group is preferred, and hydrogen is more preferable from the viewpoint of easily obtaining a narrow half width in the luminescence spectrum.

R8 及R9 較佳為烷基、芳基、雜芳基、氟、含氟烷基、含氟雜芳基或含氟芳基。尤其，就對於激發光穩定，且可獲得更高的發光量子產率而言，R8 及R9 更佳為氟或含氟芳基。進而，就合成的容易性而言，R8 及R9 進而更佳為氟。R 8 and R 9 are preferably an alkyl group, an aryl group, a heteroaryl group, a fluorine, a fluorine-containing alkyl group, a fluorine-containing heteroaryl group or a fluorine-containing aryl group. In particular, R 8 and R 9 are more preferably fluorine or a fluorine-containing aryl group for the stabilization of the excitation light and obtaining a higher luminescence quantum yield. Further, in terms of easiness of synthesis, R 8 and R 9 are more preferably fluorine.

此處，所謂含氟芳基，是指含有氟的芳基，例如可列舉：氟苯基、三氟甲基苯基及五氟苯基等。所謂含氟雜芳基，是指含有氟的雜芳基，例如可列舉：氟吡啶基、三氟甲基吡啶基及三氟吡啶基等。所謂含氟烷基，是指含有氟的烷基，例如可列舉：三氟甲基或五氟乙基等。Here, the fluorine-containing aryl group means a fluorine-containing aryl group, and examples thereof include a fluorophenyl group, a trifluoromethylphenyl group, and a pentafluorophenyl group. The fluorine-containing heteroaryl group means a fluorine-containing heteroaryl group, and examples thereof include a fluoropyridyl group, a trifluoromethylpyridyl group, and a trifluoropyridyl group. The fluorine-containing alkyl group means a fluorine-containing alkyl group, and examples thereof include a trifluoromethyl group and a pentafluoroethyl group.

另外，通式（4）中，就光穩定性的觀點而言，X較佳為C-R7 。當X為C-R7 時，取代基R7 對由通式（4）所表示的化合物的耐久性，即該化合物的發光強度的經時的下降產生大的影響。具體而言，當R7 為氫時，該部位的反應性高，因此該部位與空氣中的水分或氧容易進行反應。該反應會引起由通式（4）所表示的化合物的分解。另外，當R7 例如為如烷基般的分子鏈的運動的自由度大的取代基時，反應性確實下降，但於組成物中化合物彼此經時地凝聚，結果導致由濃度淬滅所引起的發光強度的下降。因此，R7 較佳為剛直、且運動的自由度小並難以引起凝聚的基，具體而言，較佳為經取代或未經取代的芳基、或者經取代或未經取代的雜芳基的任一者。Further, in the general formula (4), X is preferably CR 7 from the viewpoint of photostability. When X is CR 7 , the substituent R 7 has a large influence on the durability of the compound represented by the general formula (4), that is, the decrease in the luminous intensity of the compound over time. Specifically, when R 7 is hydrogen, the reactivity of the site is high, and thus the site is easily reacted with moisture or oxygen in the air. This reaction causes decomposition of the compound represented by the general formula (4). Further, when R 7 is, for example, a substituent having a large degree of freedom in the movement of a molecular chain such as an alkyl group, the reactivity does decrease, but in the composition, the compounds are agglomerated with each other over time, resulting in concentration quenching. The decline in luminous intensity. Therefore, R 7 is preferably a group which is rigid and has a small degree of freedom of movement and is hard to cause aggregation. Specifically, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is preferred. Any of them.

就提供更高的發光量子產率、更難以熱分解的觀點，另外，就光穩定性的觀點而言，較佳為X為C-R7 ，且R7 為經取代或未經取代的芳基。作為芳基，就無損發光波長這一觀點而言，較佳為苯基、聯苯基、聯三苯基、萘基、茀基、菲基、蒽基。In view of providing a higher luminescence quantum yield and more difficult to thermally decompose, in addition, from the viewpoint of photostability, X is preferably CR 7 and R 7 is a substituted or unsubstituted aryl group. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group or a fluorenyl group from the viewpoint of not impairing the emission wavelength.

進而，為了提高由通式（4）所表示的化合物的光穩定性，必須適度地抑制R7 與吡咯亞甲基骨架的碳-碳鍵的扭曲。其原因在於：若扭曲過大，則對於激發光的反應性變高等，光穩定性下降。就此種觀點而言，作為R7 ，較佳為經取代或未經取代的苯基、經取代或未經取代的聯苯基、經取代或未經取代的聯三苯基、經取代或未經取代的萘基，更佳為經取代或未經取代的苯基、經取代或未經取代的聯苯基、經取代或未經取代的聯三苯基。特佳為經取代或未經取代的苯基。Further, in order to improve the photostability of the compound represented by the general formula (4), it is necessary to appropriately suppress the distortion of the carbon-carbon bond between R 7 and the pyrrolethymethylene skeleton. This is because if the distortion is too large, the reactivity with respect to the excitation light becomes high, and the light stability is lowered. In this regard, as R 7 , a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted biphenyl group, a substituted or not The substituted naphthyl group is more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted biphenyl group. Particularly preferred are substituted or unsubstituted phenyl groups.

另外，R7 較佳為體積適度大的取代基。藉由R7 具有某種程度的體積大小，可防止分子的凝聚。其結果，由通式（4）所表示的化合物的發光效率或耐久性進一步提昇。Further, R 7 is preferably a substituent having a moderately large volume. By having a certain volume of R 7 , the aggregation of molecules can be prevented. As a result, the luminous efficiency or durability of the compound represented by the general formula (4) is further improved.

作為此種體積大的取代基的更佳例，可列舉由下述通式（5）所表示的R7 的結構。A more preferable example of such a bulky substituent is a structure of R 7 represented by the following formula (5).

[化9] [Chemistry 9]

通式（5）中，r選自由氫、烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基所組成的群組。k為1～3的整數。當k為2以上時，r分別可相同，亦可不同。In the formula (5), r is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio, aryl ether , aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, amine methyl group, amine group, nitro group, decyl group, decyloxy group, boron boron a group consisting of a phosphine oxide group. k is an integer of 1-3. When k is 2 or more, r may be the same or different.

就可提供更高的發光量子產率這一觀點而言，r較佳為經取代或未經取代的芳基。該芳基之中，尤其可列舉苯基、萘基作為較佳例。當r為芳基時，通式（5）的k較佳為1或2，其中，就進一步防止分子的凝聚這一觀點而言，更佳為2。進而，當k為2以上時，r的至少1個較佳為經烷基取代。作為該情況下的烷基，就熱穩定性的觀點而言，可列舉甲基、乙基及第三丁基作為特佳例。From the standpoint of providing a higher luminescence quantum yield, r is preferably a substituted or unsubstituted aryl group. Among the aryl groups, a phenyl group and a naphthyl group are particularly preferable. When r is an aryl group, k of the formula (5) is preferably 1 or 2, and more preferably 2 from the viewpoint of further preventing aggregation of molecules. Further, when k is 2 or more, at least one of r is preferably substituted with an alkyl group. The alkyl group in this case is a particularly preferable example from the viewpoint of thermal stability, and a methyl group, an ethyl group, and a third butyl group.

另外，就控制螢光波長或吸收波長、或提高與溶媒的相容性這一觀點而言，r較佳為經取代或未經取代的烷基、經取代或未經取代的烷氧基或鹵素，更佳為甲基、乙基、第三丁基、甲氧基。就分散性的觀點而言，特佳為第三丁基、甲氧基。r為第三丁基或甲氧基對於防止由分子彼此的凝聚所引起的淬滅更有效。Further, in terms of controlling the fluorescence wavelength or absorption wavelength, or improving compatibility with a solvent, r is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group or Halogen is more preferably methyl, ethyl, tert-butyl or methoxy. From the viewpoint of dispersibility, it is particularly preferably a tributyl group or a methoxy group. The fact that r is a third butyl group or a methoxy group is more effective for preventing quenching caused by aggregation of molecules with each other.

另外，作為由通式（4）所表示的化合物的其他形態，較佳為R1 ～R7 中的至少1個為拉電子基。尤其，較佳為（1）R1 ～R6 中的至少1個為拉電子基，（2）R7 為拉電子基，或（3）R1 ～R6 中的至少1個為拉電子基、且R7 為拉電子基。藉由如所述般將拉電子基導入至所述化合物的吡咯亞甲基骨架上，可大幅度地降低吡咯亞甲基骨架的電子密度。藉此，所述化合物對於氧的穩定性進一步提昇，其結果，可進一步提昇所述化合物的耐久性。Further, as another aspect of the compound represented by the formula (4), at least one of R 1 to R 7 is preferably an electron-withdrawing group. In particular, it is preferred that at least one of (1) R 1 to R 6 is a pull electron group, (2) R 7 is a pull electron group, or (3) at least one of R 1 to R 6 is a pull electron. And R 7 is a pull electron group. By introducing an electron withdrawing group onto the pyrromethene skeleton of the compound as described above, the electron density of the pyrrolebenzyl skeleton can be drastically reduced. Thereby, the stability of the compound to oxygen is further improved, and as a result, the durability of the compound can be further improved.

所謂拉電子基，亦稱為電子接受性基，於有機電子論中，是指藉由誘導效應或共振效應，自經取代的原子團中吸引電子的原子團。作為拉電子基，可列舉採用正的值作為哈米特方程的取代基常數（σp（對位））者。哈米特方程的取代基常數（σp（對位））可自化學便覽基礎篇修訂5版（II-380頁）中引用。再者，苯基亦有採用如上所述的正的值的例子，但於本發明中，拉電子基中不含苯基。The so-called electron-donating group, also called electron accepting group, refers to an atomic group that attracts electrons from a substituted atomic group by an inductive effect or a resonance effect. As the electron withdrawing group, a positive value is used as a substituent constant (σp (para)) of the Hammett equation. The substituent constant (σp (para)) of the Hammett equation can be quoted from the Chemical Review Basics Revision 5 (page II-380). Further, the phenyl group also has an example in which a positive value as described above is employed, but in the present invention, the electron-withdrawing group does not contain a phenyl group.

作為拉電子基的例子，例如可列舉：-F（σp：＋0.20）、-Cl（σp：＋0.28）、-Br（σp：＋0.30）、-I（σp：＋0.30）、-CO2 R12 （σp：R12 為乙基時＋0.45）、-CONH2 （σp：＋0.38）、-COR12 （σp：R12 為甲基時＋0.49）、-CF3 （σp：＋0.51）、-SO2 R12 （σp：R12 為甲基時＋0.69）、-NO2 （σp：＋0.81）等。R12 分別獨立地表示氫原子、經取代或未經取代的環形成碳數6～30的芳香族烴基、經取代或未經取代的環形成原子數5～30的雜環基、經取代或未經取代的碳數1～30的烷基、經取代或未經取代的碳數1～30的環烷基。作為所述各基的具體例，可列舉與所述相同的例子。Examples of the electron withdrawing group include -F(σp:+0.20), -Cl(σp:+0.28), -Br(σp:+0.30), and -I(σp:+0.30). , -CO 2 R 12 (σp: R = 12 when the ethyl group is +0.45), -CONH 2 (σp: +0.38), -COR 12 (σp: +129 when the R 12 is methyl), -CF 3 (σp: +0.51), -SO 2 R 12 (σp: +129 when R 12 is a methyl group), -NO 2 (σp: +0.81), or the like. R 12 each independently represents a hydrogen atom, a substituted or unsubstituted ring to form an aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted ring to form a heterocyclic group having 5 to 30 atoms, substituted or Unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms. Specific examples of the respective groups include the same examples as described above.

作為較佳的拉電子基，可列舉：氟、含氟芳基、含氟雜芳基、含氟烷基、經取代或未經取代的醯基、經取代或未經取代的酯基、經取代或未經取代的醯胺基、經取代或未經取代的磺醯基或氰基。其原因在於：該些基難以化學分解。Preferred examples of the electron withdrawing group include fluorine, fluorine-containing aryl group, fluorine-containing heteroaryl group, fluorine-containing alkyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted ester group, and Substituted or unsubstituted guanidino, substituted or unsubstituted sulfonyl or cyano. The reason is that the groups are difficult to chemically decompose.

作為更佳的拉電子基，可列舉：含氟烷基、經取代或未經取代的醯基、經取代或未經取代的酯基或氰基。其原因在於：該些基與防止濃度淬滅、提昇發光量子產率的效果相關。特佳的拉電子基為經取代或未經取代的酯基。As a more preferred electron withdrawing group, a fluorine-containing alkyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted ester group or a cyano group can be cited. The reason for this is that the groups are related to the effect of preventing concentration quenching and increasing the quantum yield of luminescence. Particularly preferred electron withdrawing groups are substituted or unsubstituted ester groups.

作為由通式（4）所表示的化合物的特佳例的一者，可列舉：R1 、R3 、R4 及R6 均分別可相同，亦可不同，且為經取代或未經取代的烷基，進而X為C-R7 ，R7 為由通式（5）所表示的基的情況。於此情況下，R7 特佳為由含有r作為經取代或未經取代的苯基的通式（5）所表示的基。As one of the particularly preferable examples of the compound represented by the formula (4), R 1 , R 3 , R 4 and R 6 may be the same or different, and may be substituted or unsubstituted. The alkyl group, and further, X is CR 7 and R 7 is a group represented by the formula (5). In this case, R 7 is particularly preferably a group represented by the formula (5) containing r as a substituted or unsubstituted phenyl group.

另外，作為由通式（4）所表示的化合物的特佳例的另一者，可列舉：R1 、R3 、R4 及R6 均分別可相同，亦可不同，且自所述Ar-1～Ar-6中選擇，進而X為C-R7 ，R7 為由通式（5）所表示的基的情況。於此情況下，R7 更佳為由含有r作為第三丁基、甲氧基的通式（5）所表示的基，特佳為由含有r作為甲氧基的通式（5）所表示的基。Further, as another example of a particularly preferable example of the compound represented by the formula (4), R 1 , R 3 , R 4 and R 6 may be the same or different, and from the Ar It is selected from -1 to Ar-6, and further, X is CR 7 and R 7 is a group represented by the formula (5). In this case, R 7 is more preferably a group represented by the formula (5) containing r as a tributyl group or a methoxy group, and particularly preferably a formula (5) containing r as a methoxy group. The base of the representation.

以下表示由通式（4）所表示的化合物的一例，但該化合物並不限定於該些例子。An example of the compound represented by the formula (4) is shown below, but the compound is not limited to these examples.

[化10] [化10]

[化11] [11]

[化12] [化12]

[化13] [Chemistry 13]

[化14] [Chemistry 14]

[化15] [化15]

[化16] [Chemistry 16]

[化17] [化17]

[化18] [化18]

[化19] [Chemistry 19]

[化20] [Chemistry 20]

[化21] [Chem. 21]

[化22] [化22]

[化23] [化23]

[化24] [Chem. 24]

[化25] [化25]

[化26] [Chem. 26]

[化27] [化27]

[化28] [化28]

[化29] [化29]

[化30] [化30]

[化31] [化31]

[化32] [化32]

[化33] [化33]

[化34] [化34]

由通式（4）所表示的化合物例如可藉由日本專利特表平8-509471號公報或日本專利特開2000-208262號公報中所記載的方法來合成。即，藉由使吡咯亞甲基化合物與金屬鹽在鹼共存下進行反應，可獲得作為目標的吡咯亞甲基系金屬錯合物。The compound represented by the formula (4) can be synthesized, for example, by the method described in JP-A-H08-509471 or JP-A-2000-208262. That is, by reacting a pyrrolemethylene compound and a metal salt in the presence of a base, a target pyrrolethymethylene metal complex can be obtained.

另外，關於吡咯亞甲基-氟化硼錯合物的合成，可參考「有機化學期刊（J. Org. Chem.）」, vol.64, No.21, pp.7813-7819（1999）、「應用化學國際版（英語）（Angew. Chem., Int. Ed. Engl.）」, vol.36, pp.1333-1335（1997）等中所記載的方法，合成由通式（4）所表示的化合物。例如可列舉如下的方法：於***存在下，在1,2-二氯乙烷中對由下述通式（6）所表示的化合物與由通式（7）所表示的化合物進行加熱後，於三乙基胺存在下，在1,2-二氯乙烷中使由下述通式（8）所表示的化合物進行反應，藉此獲得由通式（4）所表示的化合物。但是，本發明並不限定於此。此處，R1 ～R9 與所述說明相同。J表示鹵素。In addition, regarding the synthesis of pyrrolethymethylene-boron fluoride complex, reference may be made to "J. Org. Chem.", vol. 64, No. 21, pp. 7813-7819 (1999), The method described in "Angew. Chem., Int. Ed. Engl.", vol. 36, pp. 1333-1335 (1997), etc., synthesized by the formula (4) The compound represented. For example, a method in which a compound represented by the following formula (6) and a compound represented by the formula (7) are carried out in 1,2-dichloroethane in the presence of phosphorus oxychloride After heating, a compound represented by the following formula (8) is reacted in 1,2-dichloroethane in the presence of triethylamine, whereby a compound represented by the formula (4) is obtained. . However, the present invention is not limited to this. Here, R 1 to R 9 are the same as described above. J represents halogen.

[化35] [化35]

進而，可列舉如下的方法：於導入芳基或雜芳基時，利用鹵化衍生物與硼酸或硼酸酯化衍生物的偶合反應來生成碳-碳鍵，但本發明並不限定於此。同樣地，可列舉如下的方法：於導入胺基或咔唑基時，例如亦利用鈀等金屬觸媒下的鹵化衍生物與胺或咔唑衍生物的偶合反應來生成碳-碳鍵，但本發明並不限定於此。Further, a method of forming a carbon-carbon bond by a coupling reaction of a halogenated derivative with a boronic acid or a boronic acid ester derivative when introducing an aryl group or a heteroaryl group is exemplified, but the present invention is not limited thereto. Similarly, a method of forming a carbon-carbon bond by coupling a halogenated derivative under a metal catalyst such as palladium with an amine or a carbazole derivative, when introducing an amine group or a carbazole group, is exemplified. The present invention is not limited to this.

除由通式（4）所表示的化合物以外，本發明的實施形態的色變換組成物視需要可適宜含有其他化合物。例如，為了進一步提高自激發光朝由通式（4）所表示的化合物的能量移動效率，可含有紅螢烯等輔助摻雜劑。另外，當欲加入由通式（4）所表示的化合物的發光色以外的發光色時，可添加所期望的有機發光材料，例如香豆素系色素、羅丹明系色素等有機發光材料。此外，除該些有機發光材料以外，亦可將無機螢光體、螢光顏料、螢光染料、量子點等公知的發光材料組合來添加。The color conversion composition of the embodiment of the present invention may optionally contain other compounds, in addition to the compound represented by the formula (4). For example, in order to further increase the energy transfer efficiency of the self-excitation light toward the compound represented by the general formula (4), an auxiliary dopant such as red fluorene may be contained. Further, when an illuminating color other than the luminescent color of the compound represented by the general formula (4) is to be added, a desired organic luminescent material such as a coumarin-based dye or a rhodamine-based dye may be added. Further, in addition to the organic light-emitting materials, a known light-emitting material such as an inorganic phosphor, a fluorescent pigment, a fluorescent dye, or a quantum dot may be added in combination.

以下，以下表示由通式（4）所表示的化合物以外的有機發光材料的一例，但本發明並不特別限定於該些例子。Hereinafter, an example of the organic light-emitting material other than the compound represented by the general formula (4) is shown below, but the present invention is not particularly limited to these examples.

[化36] [化36]

本發明的實施形態的色變換組成物較佳為含有藉由使用波長430 nm以上、500 nm以下的範圍的激發光，而呈現於峰值波長為500 nm以上、580 nm以下的區域中所觀測到的發光的發光材料（以下，稱為「發光材料（a）」）。以後，將於峰值波長為500 nm以上、580 nm以下的區域中所觀測到的發光稱為「綠色的發光」。通常，激發光的能量越大，越容易引起材料的分解。但是，波長430 nm以上、500 nm以下的範圍的激發光是激發能量比較小者。因此，不會引起色變換組成物中的發光材料（a）的分解，可獲得色純度良好的綠色的發光。The color conversion composition of the embodiment of the present invention is preferably contained in a region having a peak wavelength of 500 nm or more and 580 nm or less by using excitation light having a wavelength of 430 nm or more and 500 nm or less. A light-emitting luminescent material (hereinafter referred to as "light-emitting material (a)"). In the future, the luminescence observed in a region having a peak wavelength of 500 nm or more and 580 nm or less is referred to as "green luminescence". Generally, the greater the energy of the excitation light, the more likely it is to cause decomposition of the material. However, excitation light having a wavelength of 430 nm or more and 500 nm or less is relatively small in excitation energy. Therefore, decomposition of the luminescent material (a) in the color conversion composition is not caused, and green luminescence with good color purity can be obtained.

本發明的實施形態的色變換組成物較佳為含有以下的發光材料（a）及發光材料（b）。如上所述，發光材料（a）是藉由使用波長430 nm以上、500 nm以下的範圍的激發光，而呈現峰值波長為500 nm以上、580 nm以下的發光的發光材料。發光材料（b）是藉由波長430 nm以上，500 nm以下的範圍的激發光及來自發光材料（a）的發光的至少一者而得到激發，藉此呈現於峰值波長為580 nm以上、750 nm以下的區域中所觀測到的發光的發光材料。以後，將於峰值波長為580 nm以上、750 nm以下的區域中所觀測到的發光稱為「紅色的發光」。The color conversion composition of the embodiment of the present invention preferably contains the following luminescent material (a) and luminescent material (b). As described above, the luminescent material (a) is a luminescent material that emits light having a peak wavelength of 500 nm or more and 580 nm or less by using excitation light having a wavelength of 430 nm or more and 500 nm or less. The luminescent material (b) is excited by at least one of excitation light having a wavelength of 430 nm or more and 500 nm or less and luminescence from the luminescent material (a), thereby exhibiting a peak wavelength of 580 nm or more and 750. Luminescent luminescent material observed in the region below nm. In the future, the luminescence observed in a region having a peak wavelength of 580 nm or more and 750 nm or less is referred to as "red luminescence".

波長430 nm以上、500 nm以下的範圍的激發光的一部分於本發明的實施形態的色變換膜中透過一部分，因此當使用發光峰值尖銳的藍色LED時，於藍色、綠色、紅色的各色中顯示出形狀尖銳的發光光譜，可獲得色純度良好的白色光。其結果，尤其於顯示器中，可有效率地製作色彩更鮮豔且更大的色域。另外，於照明用途中，與目前成為主流的將藍色LED與黃色螢光體組合而成的白色LED相比，尤其改善綠色區域及紅色區域的發光特性，因此可獲得演色性提昇的較佳的白色光源。A part of the excitation light having a wavelength of 430 nm or more and 500 nm or less is partially transmitted through the color conversion film of the embodiment of the present invention. Therefore, when a blue LED having a sharp emission peak is used, the colors of blue, green, and red are used. A sharp luminescence spectrum is shown, and white light with good color purity can be obtained. As a result, especially in the display, it is possible to efficiently produce a color gamut that is more vivid and larger. Further, in the lighting use, the light-emitting characteristics of the green region and the red region are particularly improved as compared with the white LED in which the blue LED and the yellow phosphor are combined, so that the color rendering property can be improved. White light source.

作為發光材料（a），除香豆素6、香豆素7、香豆素153等香豆素衍生物，吲哚花青綠等花青衍生物，螢光素、螢光素異硫氰酸酯、羧基螢光素二乙酸酯等螢光素衍生物，酞菁綠等酞菁衍生物，二異丁基-4,10-二氰基苝-3,9-二羧酸酯等苝衍生物以外，可列舉吡咯亞甲基衍生物、二苯乙烯衍生物、噁嗪衍生物、萘二甲醯亞胺衍生物、吡嗪衍生物、苯并咪唑衍生物、苯并噁唑衍生物、苯并噻唑衍生物、咪唑并吡啶衍生物、唑衍生物、蒽等具有縮合芳基環的化合物或其衍生物，芳香族胺衍生物，有機金屬錯化合物等作為適宜者。但是，發光材料（a）並不特別限定於該些化合物。該些化合物之中，吡咯亞甲基衍生物因提供高發光量子產率，且耐久性良好，故為特別適宜的化合物。吡咯亞甲基衍生物之中，由通式（4）所表示的化合物因顯示出色純度高的發光，故較佳。As the luminescent material (a), coumarin derivatives such as coumarin 6, coumarin 7, coumarin 153, cyanine derivatives such as phthalocyanine, luciferin, luciferin isothiocyanate Fluorescent derivatives such as esters and carboxyfluorescein diacetate, phthalocyanine derivatives such as phthalocyanine green, diisobutyl-4,10-dicyanoindole-3,9-dicarboxylate, etc. Examples of the derivative include a pyrrolethymethylene derivative, a stilbene derivative, an oxazine derivative, a naphthoquinone imine derivative, a pyrazine derivative, a benzimidazole derivative, and a benzoxazole derivative. A benzothiazole derivative, an imidazopyridine derivative, an azole derivative, a compound having a condensed aryl ring such as hydrazine or a derivative thereof, an aromatic amine derivative, an organometallic compound, or the like is suitable. However, the luminescent material (a) is not particularly limited to these compounds. Among these compounds, pyrrolethymethylene derivatives are particularly suitable compounds because they provide high luminescence quantum yield and good durability. Among the pyrrolethymethylene derivatives, the compound represented by the formula (4) is preferred because it exhibits excellent light emission with high purity.

作為發光材料（b），除4-二氰基亞甲基-2-甲基-6-(對二甲基胺基苯乙烯基)-4H-吡喃等花青衍生物，羅丹明B、羅丹明6G、羅丹明101、磺基羅丹明101等羅丹明衍生物，1-乙基-2-(4-(對二甲基胺基苯基)-1,3-丁二烯基)-吡啶鎓-過氯酸鹽等吡啶衍生物，N,N'-雙(2,6-二異丙基苯基)-1,6,7,12-四苯氧基苝-3,4,9,10-雙二碳醯亞胺等苝衍生物以外，可列舉卟啉衍生物、吡咯亞甲基衍生物、噁嗪衍生物、吡嗪衍生物、稠四苯或二苯并二茚并苝等具有縮合芳基環的化合物或其衍生物，有機金屬錯化合物等作為適宜者。但是，發光材料（b）並不特別限定於該些化合物。As the luminescent material (b), except for 4-cyanomethylene-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran, etc., rhodamine B, Rhodamine 6G, Rhodamine 101, sulforhodamine 101 and other rhodamine derivatives, 1-ethyl-2-(4-(p-dimethylaminophenyl)-1,3-butadienyl)- Pyridine derivative such as pyridinium-perchlorate, N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetraphenoxyindole-3,4,9 In addition to an anthracene derivative such as 10-bisbicarbimine, a porphyrin derivative, a pyrromethene derivative, an oxazine derivative, a pyrazine derivative, a condensed tetraphenyl or a dibenzodiazepine may be mentioned. A compound having a condensed aryl ring or a derivative thereof, an organometallic compound or the like is suitable. However, the luminescent material (b) is not particularly limited to these compounds.

該些化合物之中，吡咯亞甲基衍生物因提供高發光量子產率，且耐久性良好，故為特別適宜的化合物。吡咯亞甲基衍生物之中，由通式（4）所表示的化合物因顯示出色純度高的發光，故較佳。Among these compounds, pyrrolethymethylene derivatives are particularly suitable compounds because they provide high luminescence quantum yield and good durability. Among the pyrrolethymethylene derivatives, the compound represented by the formula (4) is preferred because it exhibits excellent light emission with high purity.

本發明的實施形態的色變換組成物中的（A）成分的含量雖然亦取決於化合物的莫耳吸光係數、發光量子產率及激發波長中的吸收強度、以及所製作的膜的厚度或透過率，但通常相對於（B）成分的100重量份為1.0×10-4 重量份～30重量份。相對於（B）成分的100重量份，該（A）成分的含量更佳為1.0×10-3 重量份～10重量份，特佳為1.0×10-2 重量份～5重量份。The content of the component (A) in the color conversion composition of the embodiment of the present invention depends on the molar absorption coefficient, the luminescence quantum yield, and the absorption intensity in the excitation wavelength of the compound, and the thickness or permeation of the produced film. The ratio is usually 1.0 × 10 -4 parts by weight to 30 parts by weight per 100 parts by weight of the component (B). The content of the component (A) is more preferably 1.0 × 10 -3 parts by weight to 10 parts by weight, particularly preferably 1.0 × 10 -2 parts by weight to 5 parts by weight, per 100 parts by weight of the component (B).

另外，當於色變換組成物中含有呈現綠色的發光的發光材料（a）、及呈現紅色的發光的發光材料（b）兩者時，就將綠色的發光的一部分變換成紅色的發光而言，較佳為所述發光材料（a）的含量wa 與發光材料（b）的含量wb 為wa ≧wb 的關係。另外，該些發光材料（a）及發光材料（b）的含有比率為wa ：wb ＝1000：1～1：1，更佳為500：1～2：1，特佳為200：1～3：1。其中，含量wa 及含量wb 是相對於（B）成分的重量的重量百分率。Further, when the color conversion composition contains both the luminescent material (a) that emits green light and the luminescent material (b) that emits red light, a part of the green light is converted into a red light. , preferably the luminescent material (a), the content of w a light emitting material (b) in relation to the content of w b w a ≧ w b of. Further, the content ratio of the luminescent material (a) and the luminescent material (b) is w a : w b = 1000:1 to 1:1, more preferably 500:1 to 2:1, and particularly preferably 200:1. ~3:1. Here, the content w a and the content w b are weight percentages relative to the weight of the component (B).

＜（B）成分：黏合劑樹脂＞ 本發明的實施形態的色變換組成物含有黏合劑樹脂作為（B）成分。黏合劑樹脂為形成連續相者，只要是成型加工性、透明性、耐熱性等優異的材料即可。作為黏合劑樹脂的例子，例如可列舉：丙烯酸系、甲基丙烯酸系、聚桂皮酸乙烯基系、環橡膠系等的具有反應性乙烯基的光硬化型抗蝕劑材料，環氧樹脂，矽酮樹脂（包含矽酮橡膠、矽酮凝膠等有機聚矽氧烷硬化物（交聯物）），脲樹脂，氟樹脂，聚碳酸酯樹脂，丙烯酸樹脂，胺基甲酸酯樹脂，三聚氰胺樹脂，聚乙烯基樹脂，聚醯胺樹脂，酚樹脂，聚乙烯醇樹脂，聚乙烯丁醛樹脂，纖維素樹脂，脂肪族酯樹脂，芳香族酯樹脂，脂肪族聚烯烴樹脂，芳香族聚烯烴樹脂等公知者。另外，作為黏合劑樹脂，亦可使用該些的共聚樹脂。藉由適宜設計該些樹脂，可獲得於本發明的實施形態的色變換組成物及色變換膜中有用的黏合劑樹脂。<Component (B): Binder Resin> The color conversion composition of the embodiment of the present invention contains a binder resin as the component (B). The binder resin may be a material that forms a continuous phase as long as it is excellent in moldability, transparency, heat resistance, and the like. Examples of the binder resin include a photocurable resist material having a reactive vinyl group such as an acrylic resin, a methacrylic resin, a polycinnamic acid vinyl group, or a ring rubber system, and an epoxy resin or an anthracene. Ketone resin (including organic polyoxyalkylene cured product (crosslinking) such as anthrone rubber, anthrone gel), urea resin, fluororesin, polycarbonate resin, acrylic resin, urethane resin, melamine resin , polyvinyl resin, polyamide resin, phenol resin, polyvinyl alcohol resin, polyvinyl butyral resin, cellulose resin, aliphatic ester resin, aromatic ester resin, aliphatic polyolefin resin, aromatic polyolefin resin And other known people. Further, as the binder resin, these copolymer resins can also be used. By suitably designing these resins, a binder resin useful for the color conversion composition and the color conversion film of the embodiment of the present invention can be obtained.

該些樹脂之中，就膜化的製程容易而言，更佳為熱硬化性樹脂。熱硬化性樹脂之中，尤其就透明性、耐熱性等的觀點而言，可適宜地使用環氧樹脂、矽酮樹脂、丙烯酸樹脂、聚酯樹脂或該些的混合物。Among these resins, the film forming process is more preferably a thermosetting resin. Among the thermosetting resins, an epoxy resin, an anthrone resin, an acrylic resin, a polyester resin or a mixture of these may be suitably used from the viewpoint of transparency, heat resistance and the like.

另外，於黏合劑樹脂中，亦可添加用於塗佈膜穩定化的分散劑或調平劑等作為添加劑，且亦可添加矽烷偶合劑等接著助劑等作為膜表面的改質劑。另外，於黏合劑樹脂中，亦可添加二氧化矽粒子或矽酮微粒子等無機粒子作為色變換材沈澱抑制劑。Further, a dispersant or a leveling agent for stabilizing the coating film may be added as an additive to the binder resin, and a bonding aid such as a decane coupling agent may be added as a modifier for the surface of the film. Further, inorganic particles such as cerium oxide particles or fluorenone fine particles may be added to the binder resin as a color conversion material precipitation inhibitor.

另外，就耐熱性的觀點而言，黏合劑樹脂特佳為矽酮樹脂。矽酮樹脂之中，較佳為加成反應硬化型矽酮組成物。加成反應硬化型矽酮組成物於常溫或50℃～200℃的溫度下進行加熱、硬化，且透明性、耐熱性、接著性優異。Further, from the viewpoint of heat resistance, the binder resin is particularly preferably an anthrone resin. Among the fluorenone resins, an addition reaction-curable fluorenone composition is preferred. The addition reaction-curable anthrone composition is heated and hardened at a normal temperature or a temperature of 50 to 200 ° C, and is excellent in transparency, heat resistance, and adhesion.

作為一例，加成反應硬化型矽酮組成物藉由含有鍵結於矽原子上的烯基的化合物與含有鍵結於矽原子上的氫原子的化合物的矽氫化反應來形成。此種材料之中，作為「含有鍵結於矽原子上的烯基的化合物」，例如可列舉：乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、烯丙基三甲氧基矽烷、丙烯基三甲氧基矽烷、降冰片烯基三甲氧基矽烷、辛烯基三甲氧基矽烷等。作為「含有鍵結於矽原子上的氫原子的化合物」，例如可列舉：甲基氫聚矽氧烷、二甲基聚矽氧烷-CO-甲基氫聚矽氧烷、乙基氫聚矽氧烷、甲基氫聚矽氧烷-CO-甲基苯基聚矽氧烷等。另外，作為加成反應硬化型矽酮組成物，除所述以外，例如亦可利用如日本專利特開2010-159411號公報中所記載的公知者。As an example, the addition reaction-curable fluorenone composition is formed by hydrogenation of a compound containing an alkenyl group bonded to a ruthenium atom with a ruthenium containing a hydrogen atom bonded to a ruthenium atom. Among such materials, examples of the "compound containing an alkenyl group bonded to a ruthenium atom" include vinyl trimethoxy decane, vinyl triethoxy decane, allyl trimethoxy decane, and propylene. Trimethoxy decane, norbornene trimethoxy decane, octenyl trimethoxy decane, and the like. Examples of the "compound containing a hydrogen atom bonded to a ruthenium atom" include methyl hydrogen polyoxy siloxane, dimethyl polyoxy siloxane - CO-methyl hydrogen polyoxy siloxane, and ethyl hydrogen polymerization. A halogenated alkane, a methyl hydrogen polyoxyalkylene-CO-methylphenyl polyoxyalkylene or the like. In addition, as an addition reaction-curable fluorene ketone composition, a well-known person as described in Japanese Laid-Open Patent Publication No. 2010-159411, for example, may be used.

另外，作為加成反應硬化型矽酮組成物，亦可使用市售者，例如一般的LED用途的矽酮密封材。作為其具體例，可列舉：東麗・道康寧公司製造的OE-6630A/B、OE-6336A/B或信越化學工業股份有限公司製造的SCR-1012A/B、SCR-1016A/B等。Further, as the addition reaction-curable anthrone composition, a commercially available one, for example, an anthrone sealing material for general LED use can be used. Specific examples thereof include OE-6630A/B manufactured by Toray Dow Corning Corporation, OE-6336A/B, or SCR-1012A/B and SCR-1016A/B manufactured by Shin-Etsu Chemical Co., Ltd.

於本發明的實施形態的色變換膜製作用的色變換組成物中，為了抑制常溫下的硬化並延長適用期，較佳為將乙炔醇等矽氫化反應延遲劑作為其他成分而調配至黏合劑樹脂中。另外，於無損本發明的效果的範圍內，視需要亦可向黏合劑樹脂中調配燻製二氧化矽、玻璃粉末、石英粉末等微粒子，氧化鈦、氧化鋯、鈦酸鋇、氧化鋅等無機填充劑或顏料，阻燃劑，耐熱劑，抗氧化劑，分散劑，溶劑，矽烷偶合劑或鈦偶合劑等接著性賦予劑等。In the color conversion composition for producing a color conversion film according to the embodiment of the present invention, in order to suppress curing at normal temperature and to extend the pot life, it is preferred to prepare a binder for the hydrogenation reaction retardant such as acetylene alcohol as a component. In the resin. Further, in the range in which the effects of the present invention are not impaired, fine particles such as smoked ceria, glass powder, and quartz powder may be blended into the binder resin as needed, and inorganic fillers such as titanium oxide, zirconium oxide, barium titanate, and zinc oxide may be added. An agent or a pigment, a flame retardant, a heat resistant agent, an antioxidant, a dispersant, a solvent, a decane coupling agent or a titanium coupling agent or the like.

尤其，就色變換膜的表面平滑性的觀點而言，較佳為向色變換膜製作用的矽酮樹脂組成物中添加低分子量的聚二甲基矽氧烷成分、矽油等。相對於該矽酮樹脂組成物的整體，此種成分較佳為添加100 ppm～2000 ppm，更佳為添加500 ppm～1000 ppm。In particular, from the viewpoint of surface smoothness of the color conversion film, it is preferred to add a low molecular weight polydimethyl siloxane component, eucalyptus oil, or the like to the fluorenone resin composition for color conversion film production. The component is preferably added in an amount of from 100 ppm to 2,000 ppm, more preferably from 500 ppm to 1,000 ppm, based on the total of the fluorenone resin composition.

＜（C）成分：具有由通式（1）所表示的部分結構的胺衍生物＞ 本發明的實施形態的色變換組成物含有具有由通式（1）所表示的部分結構的胺衍生物作為（C）成分。<(C) component: an amine derivative having a partial structure represented by the general formula (1)> The color conversion composition of the embodiment of the present invention contains an amine derivative having a partial structure represented by the general formula (1) As component (C).

[化37] [化37]

通式（1）中，R10 ～R14 分別可相同，亦可不同，且自氫原子、烷基、環烷基、芳基、雜芳基中選擇。其中，R11 與R12 的至少一者及R13 與R14 的至少一者不為氫原子。In the formula (1), R 10 to R 14 may be the same or different, and may be selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group. Wherein at least one of R 11 and R 12 and at least one of R 13 and R 14 are not a hydrogen atom.

具有由通式（1）所表示的部分結構的胺衍生物防止有機發光材料的劣化，並提昇耐久性。因此，藉由該胺衍生物的作用，（A）成分（一種以上的有機發光材料）的發光強度的經時的下降得到抑制。該效果於作為（A）成分的有機發光材料為由通式（4）所表示的化合物時特別大。The amine derivative having a partial structure represented by the general formula (1) prevents deterioration of the organic light-emitting material and improves durability. Therefore, the decrease in the luminescence intensity of the component (A) (one or more organic luminescent materials) over time is suppressed by the action of the amine derivative. This effect is particularly large when the organic light-emitting material as the component (A) is a compound represented by the general formula (4).

作為有機發光材料的劣化的主要原因，有由因光照射而生成的自由基種所引起的氧化。例如，因光照射而微量生成的烷基自由基（R・）與氧迅速地進行反應，而產生過氧自由基（ROO・）。可認為自該過氧自由基所生成的過氧化物（ROOH）裂解，藉此自由基種加速地增加，而引起有機發光材料的氧化劣化。As a cause of deterioration of the organic light-emitting material, there is oxidation caused by a radical species generated by light irradiation. For example, an alkyl radical (R·) which is minutely generated by light irradiation rapidly reacts with oxygen to generate a peroxy radical (ROO·). It is considered that the peroxide (ROOH) generated from the peroxy radical is cleaved, whereby the radical species are acceleratedly increased to cause oxidative degradation of the organic light-emitting material.

具有由通式（1）所表示的部分結構的胺衍生物藉由與過氧自由基進行反應而生成氮氧自由基。氮氧自由基與烷基自由基進行反應，藉此產生烷氧基胺，但該烷氧基胺與過氧自由基進行反應，藉此再次變化成氮氧自由基。可認為藉由重複產生此種反應，使因光照射而生成的自由基種鈍化，因此可抑制有機發光材料的氧化劣化。The amine derivative having a partial structure represented by the general formula (1) generates a nitroxide radical by reacting with a peroxy radical. The nitroxide radical reacts with the alkyl radical to thereby produce an alkoxyamine, but the alkoxyamine reacts with the peroxy radical, thereby changing again to a nitroxide radical. It is considered that by repeating such a reaction, radical species generated by light irradiation are passivated, and thus oxidative degradation of the organic light-emitting material can be suppressed.

於通式（1）中，R11 與R12 的至少一者及R13 與R14 的至少一者不為氫原子。其原因在於：藉由在氮原子的附近存在取代基，可對氮氧自由基賦予適度的穩定性。In the formula (1), at least one of R 11 and R 12 and at least one of R 13 and R 14 are not a hydrogen atom. The reason for this is that moderate stability can be imparted to the nitroxide radical by the presence of a substituent in the vicinity of the nitrogen atom.

另外，於通式（1）中，就溶解性或合成的容易性的觀點而言，R11 ～R14 更佳為烷基或環烷基。進而更佳為烷基，該烷基之中，較佳為甲基。Further, in the general formula (1), R 11 to R 14 are more preferably an alkyl group or a cycloalkyl group from the viewpoint of solubility or ease of synthesis. Further, it is more preferably an alkyl group, and among the alkyl groups, a methyl group is preferred.

就與過氧自由基的反應性高這一觀點而言，R10 較佳為氫原子、烷基、環烷基，更佳為氫原子或烷基。進而，就因鹼性低，故對於有機發光材料的影響小這一觀點而言，R10 較佳為烷基，該烷基之中，較佳為甲基。From the viewpoint of high reactivity with a peroxy radical, R 10 is preferably a hydrogen atom, an alkyl group or a cycloalkyl group, more preferably a hydrogen atom or an alkyl group. Further, from the viewpoint that the alkalinity is low, the influence on the organic light-emitting material is small, and R 10 is preferably an alkyl group, and among the alkyl groups, a methyl group is preferred.

具有由通式（1）所表示的部分結構的胺衍生物（（C）成分）較佳為具有由下述的通式（2）所表示的哌啶骨架的化合物。其原因在於：氮原子的周圍的自由度適度地變小。藉由氮原子的周圍的自由度適度地變小，氮氧自由基進一步穩定化。進而，於氮原子的周圍確保適度的空間，藉此胺部位與自由基種的反應容易進行。The amine derivative (component (C)) having a partial structure represented by the formula (1) is preferably a compound having a piperidine skeleton represented by the following formula (2). The reason for this is that the degree of freedom around the nitrogen atom is moderately small. The nitroxide radical is further stabilized by the moderate degree of freedom around the nitrogen atom being moderately reduced. Further, an appropriate space is ensured around the nitrogen atom, whereby the reaction between the amine moiety and the radical species proceeds easily.

[化38] [化38]

於具有由通式（2）所表示的哌啶骨架的化合物中，R10 ～R14 與通式（1）的R10 ～R14 相同。In the compound having a piperidine skeleton represented by the formula (2), R 10 to R 14 are the same as R 10 to R 14 of the formula (1).

（C）成分並不特別限定於具有如上所述的哌啶骨架的化合物，就容易合成這一觀點而言，較佳為4-羥基哌啶衍生物或4-胺基哌啶衍生物、4-甲氧基哌啶衍生物等在哌啶的4位上具有取代基。作為該取代基，例如可列舉：烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基等。該些之中，較佳為烷基、羥基、烷氧基、氰基、羰基、羧基、氧羰基、胺甲醯基、胺基。更佳為羥基、烷氧基、氧羰基。The component (C) is not particularly limited to a compound having a piperidine skeleton as described above, and is preferably a 4-hydroxypiperidine derivative or a 4-aminopiperidine derivative, from the viewpoint of easy synthesis. The -methoxypiperidine derivative or the like has a substituent at the 4-position of piperidine. Examples of the substituent include an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, and an aryl group. Thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecardenyl, amine, nitro, decyl, decyloxy, oxo, oxidized Phosphine and the like. Among these, an alkyl group, a hydroxyl group, an alkoxy group, a cyano group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an amine carbaryl group, and an amine group are preferable. More preferably, it is a hydroxyl group, an alkoxy group, or an oxycarbonyl group.

其中，（C）成分較佳為由通式（3）所表示的化合物，其原因在於：哌啶骨架部位的移動的自由度變大，可更有效率地捕捉過氧自由基。Among them, the component (C) is preferably a compound represented by the formula (3) because the degree of freedom of movement of the piperidine skeleton portion is increased, and peroxy radicals can be more efficiently captured.

[化39] [39]

於通式（3）中，R10 ～R14 與通式（1）的R10 ～R14 相同。m為自然數。Y自單鍵、鏈狀或環狀的脂肪族烴、脂肪族雜環、芳香族烴環、芳香族雜環、或該些的組合中選擇。In the general formula (3), the same R R 10 ~ R 14 in the general formula (1) is 10 ~ R 14. m is a natural number. Y is selected from a single bond, a chain or cyclic aliphatic hydrocarbon, an aliphatic heterocyclic ring, an aromatic hydrocarbon ring, an aromatic hetero ring, or a combination thereof.

另外，於通式（3）中，m更佳為2以上的自然數。其原因在於：當由通式（3）所表示的化合物於同一分子內具有多個哌啶骨架時，自由基捕捉的效率提昇。進而，就合成的容易性的觀點而言，m較佳為10以下的自然數，更佳為6以下的自然數。Further, in the general formula (3), m is more preferably a natural number of 2 or more. The reason for this is that when the compound represented by the general formula (3) has a plurality of piperidine skeletons in the same molecule, the efficiency of radical scavenging is improved. Further, from the viewpoint of easiness of synthesis, m is preferably a natural number of 10 or less, and more preferably a natural number of 6 or less.

另外，於通式（3）中，就耐光性的觀點而言，Y較佳為單鍵、鏈狀或環狀的脂肪族烴、芳香族烴環、或該些的組合。進而，就分子的柔軟性的觀點而言，Y更佳為鏈狀的脂肪族烴、環狀的脂肪族烴、苯環、或該些的組合。Further, in the general formula (3), Y is preferably a single bond, a chain or a cyclic aliphatic hydrocarbon, an aromatic hydrocarbon ring, or a combination thereof in terms of light resistance. Further, from the viewpoint of flexibility of the molecule, Y is more preferably a chain aliphatic hydrocarbon, a cyclic aliphatic hydrocarbon, a benzene ring, or a combination thereof.

當Y為所述組合時，作為Y的結構，並不特別限定於以下者，例如可列舉：包含鏈狀的脂肪族烴的結構單元與包含環狀的脂肪族烴的結構單元連結而成的結構、或包含鏈狀的脂肪族烴的結構單元與包含芳香族烴環的結構單元連結而成的結構、包含鏈狀的脂肪族烴的2個以上的結構單元連結而成的結構等。於此種Y的結構中，就合成的容易性的觀點而言，較佳為各個結構單元經由酯鍵或醚鍵而連結。When Y is the combination, the structure of Y is not particularly limited to the following, and examples thereof include a structural unit including a chain aliphatic hydrocarbon and a structural unit containing a cyclic aliphatic hydrocarbon. A structure or a structure in which a structural unit containing a chain aliphatic hydrocarbon is bonded to a structural unit containing an aromatic hydrocarbon ring, or a structure in which two or more structural units including a chain aliphatic hydrocarbon are linked. In the structure of such Y, from the viewpoint of easiness of synthesis, it is preferred that each structural unit is linked via an ester bond or an ether bond.

進而，於通式（3）中，就對於溶媒的溶解性的觀點而言，Y更佳為鏈狀的脂肪族烴或環狀的脂肪族烴，就合成的容易性的觀點而言，Y進而更佳為鏈狀的脂肪族烴。該鏈狀的脂肪族烴特佳為飽和脂肪族烴。Further, in the general formula (3), Y is more preferably a chain aliphatic hydrocarbon or a cyclic aliphatic hydrocarbon from the viewpoint of solubility of the solvent, and from the viewpoint of easiness of synthesis, Y Further, it is more preferably a chain aliphatic hydrocarbon. The chain aliphatic hydrocarbon is particularly preferably a saturated aliphatic hydrocarbon.

但是，所述Y亦可由通式（3）中所示的部分結構以外的取代基取代。作為該取代基，例如可列舉：烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基等。However, the Y may be substituted with a substituent other than the partial structure shown in the formula (3). Examples of the substituent include an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a thiol group, an alkoxy group, an alkylthio group, an aryl ether group, and an aryl group. Thioether, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecardenyl, amine, nitro, decyl, decyloxy, oxo, oxidized Phosphine and the like.

另外，作為通式（3）的Y的例子，可列舉如下者，但並不限定於該些例子。其中，以下的結構式中的鍵結端部的黑圓點與通式（9）中的鍵結端部的黑圓點進行鍵結。另外，於以下的結構式中，n為0以上的整數。當顯示有多個n時，各個n可相同，亦可不同。於以下的例中，表示有未經取代的Y，但Y亦可由所述取代基取代。另外，通式（9）的R10 ～R14 與通式（1）的R10 ～R14 相同。Further, examples of Y as the general formula (3) include the following, but are not limited to these examples. Among them, the black dot of the bonding end portion in the following structural formula is bonded to the black dot of the bonding end portion in the general formula (9). Further, in the following structural formula, n is an integer of 0 or more. When a plurality of n are displayed, each n may be the same or different. In the following examples, unsubstituted Y is shown, but Y may be substituted by the substituent. Further, the same as R of formula (9) 10 ~ R 14 in the general formula (1) is R 10 ~ R 14.

[化40] [化40]

[化41] [化41]

另一方面，作為由通式（1）所表示的化合物的分子量，若分子量過小，則容易產生由熱所引起的擴散或凝聚，因此較佳為100以上，更佳為150以上。進而更佳為200以上。另外，作為該化合物的分子量，若分子量過大，則溶解性下降，因此較佳為1000以下，更佳為900以下。進而更佳為800以下。On the other hand, when the molecular weight of the compound represented by the formula (1) is too small, diffusion or aggregation due to heat is likely to occur, and therefore it is preferably 100 or more, and more preferably 150 or more. More preferably, it is 200 or more. Further, when the molecular weight of the compound is too large, the solubility is lowered. Therefore, the molecular weight is preferably 1,000 or less, more preferably 900 or less. More preferably, it is 800 or less.

另外，就不阻礙來自光源的光或發光材料的發光這一觀點而言，由通式（1）所表示的化合物較佳為於可見區域中的吸光係數小。具體而言，於波長400 nm以上、800 nm以下的波長區域整個區域中，該化合物的莫耳吸光係數ε較佳為1000以下，更佳為500以下。進而更佳為200以下，特佳為100以下。Further, from the viewpoint of not inhibiting light emission from the light source or light emission of the luminescent material, the compound represented by the general formula (1) preferably has a small absorption coefficient in the visible region. Specifically, in the entire region of the wavelength region of the wavelength of 400 nm or more and 800 nm or less, the molar absorption coefficient ε of the compound is preferably 1,000 or less, more preferably 500 or less. Further, it is more preferably 200 or less, and particularly preferably 100 or less.

由通式（1）所表示的化合物可列舉以下所示者作為一例，但並不限定於該些例子。The compound represented by the formula (1) is exemplified by the following examples, but is not limited to these examples.

[化42] [化42]

[化43] [化43]

[化44] [化44]

於本發明的實施形態的色變換組成物中，（C）成分的含量雖然亦取決於化合物的莫耳吸光係數、發光量子產率及激發波長中的吸收強度、以及所製作的色變換膜的厚度或透過率，但相對於（B）成分的100重量份，較佳為1.0×10-3 重量份以上，更佳為1.0×10-2 重量份以上，進而更佳為1.0×10-1 重量份以上。另外，相對於（B）成分的100重量份，（C）成分的含量較佳為30重量份以下，更佳為10重量份以下。In the color conversion composition of the embodiment of the present invention, the content of the component (C) depends on the molar absorption coefficient, the luminescence quantum yield, and the absorption intensity in the excitation wavelength of the compound, and the color conversion film produced. The thickness or the transmittance is preferably 1.0 × 10 -3 parts by weight or more, more preferably 1.0 × 10 -2 parts by weight or more, and still more preferably 1.0 × 10 -1 with respect to 100 parts by weight of the component (B). More than the weight. Further, the content of the component (C) is preferably 30 parts by weight or less, and more preferably 10 parts by weight or less based on 100 parts by weight of the component (B).

＜其他添加劑＞ 除所述（A）成分、（B）成分及（C）成分以外，本發明的實施形態的色變換組成物可含有抗氧化劑、加工及熱穩定劑、紫外線吸收劑等耐光性穩定劑、矽酮微粒子等無機粒子、及矽烷偶合劑等其他添加劑。<Other Additives> The color conversion composition of the embodiment of the present invention may contain light resistance such as an antioxidant, a processing, a heat stabilizer, or an ultraviolet absorber, in addition to the components (A), (B) and (C). Other additives such as stabilizers, inorganic particles such as fluorenone microparticles, and decane coupling agents.

作為抗氧化劑，例如可列舉2,6-二-第三丁基-對甲酚、2,6-二-第三丁基-4-乙基苯酚等酚系抗氧化劑，但並不特別限定於該些抗氧化劑。另外，該些抗氧化劑可單獨使用，亦可併用多種。Examples of the antioxidant include phenolic antioxidants such as 2,6-di-t-butyl-p-cresol and 2,6-di-t-butyl-4-ethylphenol, but are not particularly limited thereto. These antioxidants. Further, the antioxidants may be used singly or in combination of two or more.

作為加工及熱穩定劑，例如可列舉亞磷酸三丁酯、亞磷酸三環己酯、三乙基膦、二苯基丁基膦等磷系穩定劑，但並不特別限定於該些穩定劑。另外，該些穩定劑可單獨使用，亦可併用多種。Examples of the processing and heat stabilizer include phosphorus stabilizers such as tributyl phosphite, tricyclohexyl phosphite, triethylphosphine, and diphenylbutylphosphine, but are not particularly limited to the stabilizers. . Further, the stabilizers may be used singly or in combination of two or more.

作為耐光性穩定劑，例如可列舉2-(5-甲基-2-羥基苯基)苯并***、2-[2-羥基-3,5-雙(α,α-二甲基苄基)苯基]-2H-苯并***等苯并***類，但並不特別限定於該些耐光性穩定劑。另外，該些耐光性穩定劑可單獨使用，亦可併用多種。Examples of the light resistance stabilizer include 2-(5-methyl-2-hydroxyphenyl)benzotriazole and 2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl). Benzene triazole such as phenyl]-2H-benzotriazole, but is not particularly limited to these light resistance stabilizers. Further, these light resistance stabilizers may be used singly or in combination of two or more.

就不阻礙來自光源的光或發光材料的發光這一觀點而言，該些添加劑較佳為於可見區域中的吸光係數小。具體而言，於波長400 nm以上、800 nm以下的波長區域整個區域中，該些添加劑的莫耳吸光係數ε較佳為1000以下，更佳為500以下。進而更佳為200以下，特佳為100以下。The additives preferably have a small absorption coefficient in the visible region from the viewpoint of not hindering the light from the light source or the luminescence of the luminescent material. Specifically, in the entire region of the wavelength region of the wavelength of 400 nm or more and 800 nm or less, the molar absorption coefficient ε of the additives is preferably 1,000 or less, more preferably 500 or less. Further, it is more preferably 200 or less, and particularly preferably 100 or less.

另外，作為耐光性穩定劑，亦可適宜地使用具有作為單重態氧淬滅劑（singlet oxygen quencher）的作用的化合物。單重態氧淬滅劑是捕捉氧分子藉由光的能量而活化所形成的單重態氧並加以鈍化的材料。藉由單重態氧淬滅劑於組成物中共存，可防止發光材料因單重態氧而劣化。Further, as the light resistance stabilizer, a compound having a function as a singlet oxygen quencher can be suitably used. A singlet oxygen quencher is a material that captures the oxygen species and activates the formed singlet oxygen by the energy of light. By the coexistence of the singlet oxygen quencher in the composition, the luminescent material can be prevented from deteriorating due to singlet oxygen.

已知單重態氧藉由在如孟加拉玫瑰紅或亞甲藍般的色素的三重態激發狀態與基底狀態的氧分子之間產生電子與能量的交換而產生。Singlet oxygen is known to be produced by the exchange of electrons and energy between the triplet excited state of a pigment such as rose bengal or methylene blue and the oxygen molecules in the basal state.

本發明的實施形態的色變換組成物藉由所含有的有機發光材料因激發光而得到激發，並發出波長與激發光不同的光而進行光的色變換。因重複該激發-發光的循環，故藉由所產生的激發種與組成物中所含有的氧的相互作用，生成單重態氧的概率變高。因此，有機發光材料與單重態氧的碰撞概率亦變高，有機發光材料的劣化容易推進。In the color conversion composition according to the embodiment of the present invention, the organic light-emitting material contained therein is excited by the excitation light, and emits light having a wavelength different from that of the excitation light to perform color conversion of light. Since the cycle of the excitation-luminescence is repeated, the probability of generating singlet oxygen by the interaction between the generated excited species and the oxygen contained in the composition becomes high. Therefore, the collision probability of the organic light-emitting material and the singlet oxygen also becomes high, and the deterioration of the organic light-emitting material is easily advanced.

與無機發光材料相比，有機發光材料容易受到單重態氧的影響。尤其，與苝等具有縮合芳基環的化合物或其衍生物相比，由通式（4）所表示的化合物與單重態氧的反應性高，由單重態氧所產生的對於耐久性的影響大。因此，利用單重態氧淬滅劑使所產生的單重態氧迅速地鈍化，藉此可提昇發光量子產率及色純度優異的由通式（4）所表示的化合物的耐久性。Compared to inorganic luminescent materials, organic luminescent materials are susceptible to singlet oxygen. In particular, the compound represented by the formula (4) has high reactivity with singlet oxygen, and the effect on durability from singlet oxygen, compared with a compound having a condensed aryl ring such as hydrazine or a derivative thereof. Big. Therefore, the generated singlet oxygen is rapidly passivated by the singlet oxygen quencher, whereby the durability of the compound represented by the general formula (4) excellent in luminescence quantum yield and color purity can be improved.

作為具有作為單重態氧淬滅劑的作用的化合物，例如可列舉特定的三級胺、兒茶酚衍生物及鎳化合物，但並不特別限定於該些化合物。另外，該些化合物（耐光性穩定劑）可單獨使用，亦可併用多種。Examples of the compound having a function as a singlet oxygen quencher include a specific tertiary amine, a catechol derivative, and a nickel compound, but are not particularly limited to these compounds. Further, these compounds (light stabilizers) may be used singly or in combination of two or more.

所謂三級胺，表示具有氨的N-H鍵均被N-C鍵取代的結構的化合物。作為氮原子上的取代基，自烷基、環烷基、雜環基、烯基、環烯基、炔基、芳基、雜芳基、醛基、羰基、羧基、氧羰基、胺甲醯基及與鄰接取代基之間所形成的縮合環及脂肪族環中選擇。另外，該些取代基可由所述取代基進一步取代。The tertiary amine means a compound having a structure in which an N-H bond of ammonia is substituted by an N-C bond. As a substituent on a nitrogen atom, from an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aldehyde group, a carbonyl group, a carboxyl group, an oxycarbonyl group, an amine formazan The condensed ring and the aliphatic ring formed between the group and the adjacent substituent are selected. Further, the substituents may be further substituted by the substituent.

作為所述三級胺的氮原子上的取代基，就光穩定性的觀點而言，較佳為經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、經取代或未經取代的雜芳基。其中，更佳為經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基。As the substituent on the nitrogen atom of the tertiary amine, from the viewpoint of photostability, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, substituted or Unsubstituted aryl, substituted or unsubstituted heteroaryl. Of these, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group is more preferred.

作為該情況下的芳基，為了不阻礙來自光源的光或發光材料的發光，較佳為苯基或萘基，更佳為苯基。另外，若氮原子上的芳基增加，則存在可見區域的光的吸收增加的擔憂，因此氮原子上的3個取代基之中，芳基較佳為2個以下，更佳為1個以下。當氮原子上的3個取代基之中，至少1個為經取代或未經取代的烷基時，可更有效率地捕捉單重態氧，故較佳。其中，較佳為3個取代基中的2個以上為經取代或未經取代的烷基。The aryl group in this case is preferably a phenyl group or a naphthyl group, and more preferably a phenyl group, in order not to hinder light emission from the light source or light emission from the light-emitting material. Further, when the aryl group on the nitrogen atom increases, there is a concern that the absorption of light in the visible region increases. Therefore, among the three substituents on the nitrogen atom, the aryl group is preferably two or less, more preferably one or less. . When at least one of the three substituents on the nitrogen atom is a substituted or unsubstituted alkyl group, singlet oxygen can be more efficiently captured, which is preferable. Among them, it is preferred that two or more of the three substituents are substituted or unsubstituted alkyl groups.

作為較佳的三級胺，可列舉三乙基胺、1,4-二氮雜雙環[2.2.2]辛烷、三-正丁基胺、N,N-二乙基苯胺、2,2,6,6-四甲基哌啶等，但並不特別限定於該些三級胺。As preferred tertiary amines, there may be mentioned triethylamine, 1,4-diazabicyclo[2.2.2]octane, tri-n-butylamine, N,N-diethylaniline, 2,2. 6,6-tetramethylpiperidine or the like, but is not particularly limited to the tertiary amines.

另外，由通式（2）所表示的化合物只要R10 為烷基，則為三級胺。即，該化合物亦具有作為單重態氧淬滅劑的作用。Further, the compound represented by the formula (2) is a tertiary amine as long as R 10 is an alkyl group. That is, the compound also functions as a singlet oxygen quencher.

所謂兒茶酚衍生物，表示含有間苯二酚或對苯二酚等的異構體、且於苯環上具有2個以上的羥基的化合物。與苯環上的羥基為1個的苯酚衍生物相比，該些化合物可更有效率地捕捉單重態氧。The catechol derivative is a compound containing an isomer such as resorcin or hydroquinone, and having two or more hydroxyl groups on the benzene ring. These compounds can capture singlet oxygen more efficiently than phenol derivatives having one hydroxyl group on the phenyl ring.

作為兒茶酚衍生物的苯環上的取代基，除羥基以外，亦自氫、烷基、環烷基、雜環基、烯基、環烯基、炔基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基、及與鄰接取代基之間所形成的縮合環及脂肪族環中選擇。另外，該些取代基可由所述取代基進一步取代。As a substituent on the benzene ring of the catechol derivative, in addition to the hydroxyl group, it is also derived from hydrogen, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a thiol group or an alkoxy group. , alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, aminecarboxamidine, amine, nitro, decyl The oxiranyl group, the boroxyl group, the phosphine oxide group, and the condensed ring formed between the adjacent substituents and the aliphatic ring are selected. Further, the substituents may be further substituted by the substituent.

其中，就光穩定性的觀點而言，較佳為經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、經取代或未經取代的雜芳基、鹵素，更佳為經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、鹵素。就與單重態氧淬滅劑的反應後的變色小而言，進而更佳為經取代或未經取代的烷基、經取代或未經取代的環烷基、鹵素。特佳為經取代或未經取代的烷基。Among them, from the viewpoint of photostability, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, substituted or unsubstituted is preferred. The substituted heteroaryl group, halogen, more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a halogen. In terms of small discoloration after the reaction with the singlet oxygen quencher, it is more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a halogen. Particularly preferred are substituted or unsubstituted alkyl groups.

作為兒茶酚衍生物中的苯環上的羥基的位置，較佳為至少2個羥基鄰接。其原因在於：與間苯二酚（1,3-取代）或對苯二酚（1,4-取代）相比，難以被光氧化。另外，因可見區域的光的吸收於氧化後亦小，故可防止組成物的變色。The position of the hydroxyl group on the benzene ring in the catechol derivative is preferably at least two hydroxyl groups adjacent to each other. The reason for this is that it is difficult to be photooxidized compared to resorcinol (1,3-substituted) or hydroquinone (1,4-substituted). Further, since the absorption of light in the visible region is small after oxidation, discoloration of the composition can be prevented.

作為較佳的兒茶酚衍生物，可列舉4-第三丁基苯-1,2-二醇、3,5-二-第三丁基苯-1,2-二醇等，但並不特別限定於該些兒茶酚衍生物。Preferred examples of the catechol derivative include 4-tert-butylbenzene-1,2-diol and 3,5-di-t-butylbenzene-1,2-diol, but not It is particularly limited to these catechol derivatives.

所謂鎳化合物，是指含有鎳的化合物。作為鎳化合物，例如可列舉氯化鎳等無機鹽或雙乙醯丙酮鎳等錯合物、胺基甲酸鎳鹽等有機酸鹽等，但並不特別限定於該些鎳化合物。此處，所謂有機酸，表示具有羧基、磺醯基、酚性羥基、硫醇基的有機化合物。其中，作為鎳化合物，就於組成物中均勻地分散這一觀點而言，較佳為錯合物及有機酸鹽。The nickel compound refers to a compound containing nickel. The nickel compound may, for example, be an inorganic salt such as nickel chloride or a complex such as acetoacetone nickel or an organic acid salt such as a nickel urinate, but is not particularly limited to these nickel compounds. Here, the organic acid means an organic compound having a carboxyl group, a sulfonyl group, a phenolic hydroxyl group, or a thiol group. Among them, as the nickel compound, a complex compound and an organic acid salt are preferred from the viewpoint of uniformly dispersing the composition.

作為可適宜地用作單重態氧淬滅劑的鎳錯合物及有機酸的鎳鹽，例如可列舉乙醯丙酮系鎳錯合物、雙二硫代-α-二酮系鎳錯合物、二硫醇鹽系鎳錯合物、胺基硫醇鹽系鎳錯合物、硫代兒茶酚系鎳錯合物、水楊醛肟系鎳錯合物、硫代雙酚鹽系鎳錯合物、靛苯胺系鎳化合物、羧酸系鎳鹽、磺酸系鎳鹽、酚系鎳鹽、胺甲酸系鎳鹽、二硫代胺甲酸系鎳鹽等，但並不特別限定於該些化合物。Examples of the nickel complex which can be suitably used as the singlet oxygen quencher and the nickel salt of the organic acid include, for example, an acetonitrile acetone nickel complex and a bisdithio-α-diketone nickel complex. , a dithiolate nickel complex, an amine thiolate nickel complex, a thiocatechol nickel complex, a salicyl hydrazine nickel complex, a thiobisphenolate nickel a substance, an anisidine-based nickel compound, a carboxylic acid-based nickel salt, a sulfonic acid-based nickel salt, a phenol-based nickel salt, a urethane-based nickel salt, a dithiocarbamic acid-based nickel salt, etc., but is not particularly limited to these compounds .

該些之中，作為鎳化合物，較佳為有機酸的鎳鹽、乙醯丙酮系鎳錯合物及硫代雙酚鹽系鎳錯合物中的至少一種。尤其，就合成的容易性及廉價這一觀點而言，較佳為有機酸的鎳鹽。另外，就可見區域中的莫耳吸光係數小、不會吸收光源或發光材料的發光這一觀點而言，較佳為磺酸系鎳鹽。就顯示出更良好的單重態氧淬滅效果這一觀點而言，進而更佳為芳基磺酸的鎳鹽，就對於種類寬廣的溶媒的溶解性的觀點而言，進而較佳為烷基磺酸的鎳鹽。作為芳基磺酸的芳基，較佳為經取代或未經取代的苯基，就對於溶媒的溶解性及分散性的觀點而言，更佳為經烷基取代的苯基。Among these, the nickel compound is preferably at least one of a nickel salt of an organic acid, an acetonitrile acetone nickel complex, and a thiobisphenolate nickel complex. In particular, a nickel salt of an organic acid is preferred from the viewpoint of easiness of synthesis and low cost. Further, from the viewpoint that the molar absorption coefficient in the visible region is small and the light source or the light-emitting material is not absorbed, the sulfonic acid-based nickel salt is preferred. From the viewpoint of exhibiting a more excellent singlet oxygen quenching effect, it is more preferable that the nickel salt of the arylsulfonic acid is more preferably an alkyl group from the viewpoint of solubility of a wide variety of solvents. Nickel salt of sulfonic acid. The aryl group of the arylsulfonic acid is preferably a substituted or unsubstituted phenyl group, and more preferably an alkyl group-substituted phenyl group from the viewpoint of solubility in a solvent and dispersibility.

另外，作為鎳化合物，就對於有機溶劑的溶解性及可見區域中的莫耳吸光係數小這一觀點而言，較佳為乙醯丙酮系鎳錯合物及硫代雙酚鹽系鎳錯合物兩者。該些錯合物中的鎳上的配位體可由烷基、環烷基、雜環基、烯基、環烯基、炔基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基等取代基取代。另外，該些取代基可由所述取代基進一步取代。Further, as the nickel compound, from the viewpoint of solubility in an organic solvent and a molar absorption coefficient in a visible region, it is preferred that the acetonitrile acetone nickel complex and the thiobisphenolate nickel are misaligned. Both. The ligand on the nickel in the complexes may be alkyl, cycloalkyl, heterocyclyl, alkenyl, cycloalkenyl, alkynyl, thiol, alkoxy, alkylthio, aryl ether , aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, amine methyl group, amine group, nitro group, decyl group, decyloxy group, boron boron Substituents such as a phosphine oxide group or the like are substituted. Further, the substituents may be further substituted by the substituent.

其中，就光穩定性的觀點而言，較佳為經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、經取代或未經取代的雜芳基、鹵素，更佳為經取代或未經取代的烷基、經取代或未經取代的環烷基、經取代或未經取代的芳基、鹵素。進而，就與單重態氧淬滅劑的反應後的變色小而言，進而更佳為經取代或未經取代的烷基、經取代或未經取代的環烷基、鹵素。特佳為經取代或未經取代的烷基。Among them, from the viewpoint of photostability, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, substituted or unsubstituted is preferred. The substituted heteroaryl group, halogen, more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a halogen. Further, in terms of small discoloration after the reaction with the singlet oxygen quencher, it is more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group or a halogen. Particularly preferred are substituted or unsubstituted alkyl groups.

作為於波長400 nm以上、800 nm以下的波長區域整個區域中莫耳吸光係數ε為100以下的鎳化合物，例如可列舉：對甲苯甲醯基磺酸的鎳鹽或乙醯丙酮鎳（II）錯合物、六氟乙醯丙酮鎳（II）錯合物、2,2'-硫代雙酚鹽-正丁基胺鎳（II）錯合物、[2,2'-硫代雙(4-第三辛基酚鹽)]-2-乙基己基胺鎳（II）錯合物等。但是，作為鎳化合物，並不限定於該些鎳鹽或鎳錯合物，可適宜地使用所述各種鎳化合物之中，於波長400 nm以上、800 nm以下的波長區域整個區域中莫耳吸光係數ε為100以下者。The nickel compound having a molar absorption coefficient ε of 100 or less in the entire wavelength region of the wavelength range of 400 nm or more and 800 nm or less is, for example, a nickel salt of p-tolylsulfonylsulfonic acid or nickel (II) acetonitrile. Complex, hexafluoroacetone nickel(II) complex, 2,2'-thiobisphenolate-n-butylamine nickel(II) complex, [2,2'-thiobis ( 4-tert-octylphenolate]]-2-ethylhexylamine nickel (II) complex and the like. However, the nickel compound is not limited to the nickel salt or the nickel complex, and among the various nickel compounds, moiré can be used in the entire region of the wavelength region of wavelengths of 400 nm or more and 800 nm or less. The coefficient ε is 100 or less.

於本發明的實施形態的色變換組成物中，該些添加劑的含量雖然亦取決於化合物的莫耳吸光係數、發光量子產率及激發波長中的吸收強度、以及所製作的色變換膜的厚度或透過率，但通常相對於（B）成分的100重量份，較佳為1.0×10-3 重量份以上，更佳為1.0×10-2 重量份以上，進而更佳為1.0×10-1 重量份以上。另外，相對於（B）成分的100重量份，該些添加劑的含量較佳為30重量份以下，更佳為15重量份以下，進而更佳為10重量份以下。In the color conversion composition of the embodiment of the present invention, the content of the additives depends on the molar absorption coefficient of the compound, the luminescence quantum yield, and the absorption intensity in the excitation wavelength, and the thickness of the produced color conversion film. Or the transmittance, but it is usually 1.0 × 10 -3 parts by weight or more, more preferably 1.0 × 10 -2 parts by weight or more, and still more preferably 1.0 × 10 -1 with respect to 100 parts by weight of the component (B). More than the weight. Further, the content of the additives is preferably 30 parts by weight or less, more preferably 15 parts by weight or less, still more preferably 10 parts by weight or less based on 100 parts by weight of the component (B).

＜溶媒＞ 本發明的實施形態的色變換組成物可含有溶媒。溶媒只要是可調整流動狀態的樹脂的黏度，且不對發光物質的發光及耐久性造成過度的影響者，則並無特別限定。作為此種溶媒，例如可列舉：水、2-丙醇、乙醇、甲苯、甲基乙基酮、甲基異丁基酮、環己酮、己烷、丙酮、萜品醇、2,2,4-三甲基-1,3-戊二醇單異丁酸酯（texanol）、甲基溶纖劑、乙基溶纖劑、丁基卡必醇、丁基卡必醇乙酸酯、1-甲氧基-2-丙醇、丙二醇單甲基醚乙酸酯等。亦可將兩種以上的該些溶媒混合使用。該些溶媒之中，尤其就不對由通式（4）所表示的化合物的劣化造成影響，且乾燥後的殘存溶媒少的觀點而言，可適宜地使用甲苯。<Solvent> The color conversion composition of the embodiment of the present invention may contain a solvent. The solvent is not particularly limited as long as it is a viscosity of the resin in a flowable state and does not excessively affect the light emission and durability of the luminescent material. Examples of such a solvent include water, 2-propanol, ethanol, toluene, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, acetone, terpineol, 2, 2, 4-trimethyl-1,3-pentanediol monoisobutyrate (texanol), methyl cellosolve, ethyl cellosolve, butyl carbitol, butyl carbitol acetate, 1 -Methoxy-2-propanol, propylene glycol monomethyl ether acetate, and the like. Two or more of these solvents may also be used in combination. Among these solvents, in particular, toluene is not affected from the viewpoint of deterioration of the compound represented by the general formula (4), and the amount of residual solvent after drying is small.

＜色變換組成物的製作方法＞ 以下，對本發明的實施形態的色變換組成物的製作方法的一例進行說明。於該製作方法中，將規定量的所述有機發光材料（（A）成分）、黏合劑樹脂（（B）成分）、胺衍生物（（C）成分）、溶媒等混合。以變成規定的組成的方式將所述成分混合後，利用均質機、自轉公轉型攪拌機、三輥機、球磨機、行星式球磨機、珠磨機等攪拌・混練機均質地進行混合分散，藉此獲得色變換組成物。於混合分散後、或混合分散的過程中，亦可較佳地於真空或減壓條件下進行消泡。另外，亦可事先混合某種特定的成分、或進行老化等處理。亦可利用蒸發器將溶媒去除來變成所期望的固體成分濃度。<Method for Producing Color Conversion Composition> Hereinafter, an example of a method for producing a color conversion composition according to an embodiment of the present invention will be described. In the production method, a predetermined amount of the organic light-emitting material (component (A)), a binder resin (component (B)), an amine derivative (component (C)), a solvent, and the like are mixed. The components are mixed in a predetermined composition, and then uniformly mixed and dispersed by a stirring and kneading machine such as a homogenizer, a self-rotating mixer, a three-roll mill, a ball mill, a planetary ball mill, or a bead mill. Color conversion composition. Defoaming may also preferably be carried out under vacuum or reduced pressure during mixing or dispersion or during mixing and dispersion. Further, it is also possible to mix a specific component in advance or perform treatment such as aging. The solvent can also be removed using an evaporator to become the desired solids concentration.

＜色變換膜的製作方法＞ 於本發明中，色變換膜只要包含使所述色變換組成物硬化所獲得的層（即，色變換組成物的硬化物層），則其構成並無限定。作為色變換膜的具有代表性的結構例，例如可列舉以下的3個例子。<Method for Producing Color Conversion Film> In the present invention, the color conversion film is not limited as long as it includes a layer obtained by curing the color conversion composition (that is, a cured layer of the color conversion composition). As a typical structural example of a color conversion film, the following three examples are mentioned, for example.

圖1是表示本發明的實施形態的色變換膜的一例的示意剖面圖。圖1中例示的色變換膜1是基材層10與色變換層11的積層體。該色變換層11為所述色變換組成物的硬化物層。於該色變換膜1的結構例中，色變換層11積層於基材層10上。Fig. 1 is a schematic cross-sectional view showing an example of a color conversion film according to an embodiment of the present invention. The color conversion film 1 illustrated in FIG. 1 is a laminate of the base material layer 10 and the color conversion layer 11. The color conversion layer 11 is a cured layer of the color conversion composition. In the configuration example of the color conversion film 1, the color conversion layer 11 is laminated on the base material layer 10.

圖2是表示本發明的實施形態的色變換膜的另一例的示意剖面圖。圖2中例示的色變換膜1是多個基材層10與色變換層11的積層體。於該色變換膜1的結構例中，色變換層11由多個基材層10夾持。Fig. 2 is a schematic cross-sectional view showing another example of the color conversion film according to the embodiment of the present invention. The color conversion film 1 illustrated in FIG. 2 is a laminated body of a plurality of base material layers 10 and color conversion layers 11. In the configuration example of the color conversion film 1, the color conversion layer 11 is sandwiched by a plurality of base material layers 10.

圖3是表示本發明的實施形態的色變換膜的又一例的示意剖面圖。圖3中例示的色變換膜1是多個基材層10、色變換層11及多個阻擋膜12的積層體。於該色變換膜1的結構例中，色變換層11由多個阻擋膜12夾持，進而，所述色變換層11與多個阻擋膜12的積層體由多個基材層10夾持。即，於色變換膜1中，為了防止色變換層11的由氧、水分或熱所引起的劣化，如圖3中所例示般，亦可設置阻擋膜12。3 is a schematic cross-sectional view showing still another example of the color conversion film according to the embodiment of the present invention. The color conversion film 1 illustrated in FIG. 3 is a laminate of a plurality of base material layers 10, a color conversion layer 11, and a plurality of barrier films 12. In the configuration example of the color conversion film 1, the color conversion layer 11 is sandwiched by the plurality of barrier films 12, and further, the laminate of the color conversion layer 11 and the plurality of barrier films 12 is sandwiched by the plurality of substrate layers 10. . That is, in the color conversion film 1, in order to prevent deterioration of the color conversion layer 11 by oxygen, moisture, or heat, the barrier film 12 may be provided as illustrated in FIG.

（基材層） 作為基材層（例如圖1～圖3中所示的基材層10等），可無特別限制地使用公知的金屬、膜、玻璃、陶瓷、紙等。具體而言，作為基材層，可列舉：鋁（亦包含鋁合金）、鋅、銅、鐵等的金屬板或箔，乙酸纖維素、聚對苯二甲酸乙二酯（Polyethylene terephthalate，PET）、聚乙烯、聚酯、聚醯胺、聚醯亞胺、聚苯硫醚、聚苯乙烯、聚丙烯、聚碳酸酯、聚乙烯縮醛、芳族聚醯胺、矽酮、聚烯烴、熱塑性氟樹脂、四氟乙烯與乙烯的共聚物（Ethylene tetrafluoroethylene，ETFE）等塑膠的膜，包含α-聚烯烴樹脂、聚己內酯樹脂、丙烯酸樹脂、矽酮樹脂及該些與乙烯的共聚樹脂的塑膠的膜，層壓有所述塑膠的紙，或藉由所述塑膠來塗佈的紙，層壓或蒸鍍有所述金屬的紙，層壓或蒸鍍有所述金屬的塑膠膜等。另外，當基材層為金屬板時，亦可對其表面實施鉻系或鎳系等的鍍敷處理或陶瓷處理。(Base Material Layer) As the base material layer (for example, the base material layer 10 shown in FIGS. 1 to 3), a known metal, film, glass, ceramic, paper, or the like can be used without particular limitation. Specifically, examples of the substrate layer include aluminum (also including aluminum alloy), metal plates or foils such as zinc, copper, and iron, and cellulose acetate and polyethylene terephthalate (PET). , polyethylene, polyester, polyamide, polyimide, polyphenylene sulfide, polystyrene, polypropylene, polycarbonate, polyvinyl acetal, aromatic polyamine, fluorenone, polyolefin, thermoplastic a film of a plastic such as a fluororesin, an ethylene tetrafluoroethylene (ETFE) or the like, comprising an α-polyolefin resin, a polycaprolactone resin, an acrylic resin, an anthrone resin, and a copolymer resin with the ethylene. a plastic film, a paper laminated with the plastic, or a paper coated with the plastic, a paper laminated or vapor-deposited, a plastic film laminated or vapor-deposited with the metal, or the like . Further, when the base material layer is a metal plate, the surface may be subjected to a plating treatment such as chromium or nickel or a ceramic treatment.

該些之中，就色變換膜的製作的容易性或色變換膜的成形的容易性而言，可較佳地使用玻璃或樹脂膜。另外，為了於對膜狀的基材層進行處理時無斷裂等之虞，較佳為強度高的膜。就該些要求特性或經濟性方面而言，較佳為樹脂膜，該些之中，就經濟性、處理性方面而言，較佳為選自由PET、聚苯硫醚、聚碳酸酯、聚丙烯所組成的群組中的塑膠膜。另外，於使色變換膜乾燥的情況或利用擠出機於200℃以上的高溫下將色變換膜壓接成形的情況下，就耐熱性方面而言，較佳為聚醯亞胺膜。就膜的剝離的容易性而言，亦可事先對基材層的表面進行脫模處理。Among these, a glass or a resin film can be preferably used in terms of easiness in production of a color conversion film or ease of formation of a color conversion film. Further, in order to treat the film-form substrate layer without cracking or the like, a film having high strength is preferable. In terms of such required characteristics or economical efficiency, a resin film is preferred, and among these, in terms of economy and handling, it is preferably selected from the group consisting of PET, polyphenylene sulfide, polycarbonate, and poly. A plastic film in a group consisting of propylene. In the case where the color conversion film is dried or when the color conversion film is pressure-bonded at a high temperature of 200 ° C or higher by an extruder, a polyimide film is preferable in terms of heat resistance. In terms of easiness of peeling off the film, the surface of the base material layer may be subjected to release treatment in advance.

基材層的厚度並無特別限制，但下限較佳為5 μm以上，更佳為25 μm以上，進而更佳為38 μm以上。另外，上限較佳為5000 μm以下，更佳為3000 μm以下。The thickness of the base material layer is not particularly limited, but the lower limit is preferably 5 μm or more, more preferably 25 μm or more, and still more preferably 38 μm or more. Further, the upper limit is preferably 5,000 μm or less, more preferably 3,000 μm or less.

（色變換層） 繼而，對本發明的實施形態的色變換膜的色變換層的製作方法的一例進行說明。於該色變換層的製作方法中，將藉由所述方法所製作的色變換組成物塗佈於基材層或阻擋膜層等基底上，並使其乾燥。如此，製作色變換層（例如圖1～圖3中所示的色變換層11）。塗佈可藉由反向輥塗機（reverse roll coater）、刮刀塗佈機（blade coater）、縫模塗佈機（slit die coator）、直接凹版塗佈機（direct gravure coater）、間接凹版塗佈機（offset gravure coater）、吻合式塗佈機（kiss coater）、自然輥塗佈機（natural roll coater）、氣刀式塗佈機（air knife coater）、輥式刮刀塗佈機（roll blade coater）、反向輥刮刀塗佈機（reverse roll blade coater）、雙流塗佈機（two stream coater）、棒式塗佈機（rod coater）、線棒塗佈機（wire bar coater）、敷料器（applicator）、浸塗機（dip coater）、簾幕式塗佈機（curtain coater）、旋轉塗佈機（spin coater）、刀式塗佈機（knife coater）等來進行。為了獲得色變換層的膜厚均勻性，較佳為藉由縫模塗佈機或浸漬塗佈機來進行塗佈。(Color Conversion Layer) Next, an example of a method of producing a color conversion layer of the color conversion film according to the embodiment of the present invention will be described. In the method for producing the color conversion layer, the color conversion composition produced by the method is applied onto a substrate such as a substrate layer or a barrier film layer, and dried. In this manner, a color conversion layer (for example, the color conversion layer 11 shown in FIGS. 1 to 3) is produced. The coating can be applied by a reverse roll coater, a blade coater, a slit die coater, a direct gravure coater, an indirect gravure coater. Offset gravure coater, kiss coater, natural roll coater, air knife coater, roll blade coater Coater), reverse roll coat coater, two stream coater, rod coater, wire bar coater, applicator (applicator), a dip coater, a curtain coater, a spin coater, a knife coater, or the like. In order to obtain film thickness uniformity of the color conversion layer, coating is preferably carried out by a slot coater or a dip coater.

色變換層的乾燥可使用熱風乾燥機或紅外線乾燥機等一般的加熱裝置來進行。色變換膜的加熱可使用熱風乾燥機或紅外線乾燥機等一般的加熱裝置。於此情況下，加熱條件通常為40℃～250℃、1分鐘～5小時，較佳為60℃～200℃、2分鐘～4小時。另外，亦可進行分步固化等階段性的加熱硬化。The drying of the color conversion layer can be carried out using a general heating device such as a hot air dryer or an infrared dryer. As the heating of the color conversion film, a general heating device such as a hot air dryer or an infrared dryer can be used. In this case, the heating conditions are usually 40 ° C to 250 ° C for 1 minute to 5 hours, preferably 60 ° C to 200 ° C for 2 minutes to 4 hours. Further, stepwise heat curing such as stepwise curing may be performed.

於製作色變換層後，視需要亦可變更基材層。於此情況下，作為簡易的方法，例如可列舉使用加熱板來進行重貼的方法、或使用真空層壓機或乾膜層壓機的方法等，但並不限定於該些方法。After the color conversion layer is formed, the substrate layer may be changed as needed. In this case, as a simple method, for example, a method of re-sticking using a hot plate or a method using a vacuum laminator or a dry film laminator may be mentioned, but the method is not limited thereto.

色變換層的厚度並無特別限制，但較佳為1 μm～1000 μm，更佳為10 μm～1000 μm。若色變換層的厚度小於1 μm，則存在色變換膜的強韌性變小這一問題。若色變換層的厚度超過1000 μm，則容易產生裂紋，且色變換膜難以成形。作為色變換層的厚度，更佳為5 μm～100 μm，進而更佳為10 μm～100 μm，特佳為15 μm～100 μm。The thickness of the color conversion layer is not particularly limited, but is preferably 1 μm to 1000 μm, more preferably 10 μm to 1000 μm. When the thickness of the color conversion layer is less than 1 μm, there is a problem that the strength and toughness of the color conversion film become small. When the thickness of the color conversion layer exceeds 1000 μm, cracks are likely to occur, and the color conversion film is difficult to be formed. The thickness of the color conversion layer is more preferably 5 μm to 100 μm, still more preferably 10 μm to 100 μm, and particularly preferably 15 μm to 100 μm.

本發明中的色變換膜的膜厚是指基於JIS K7130（1999）塑膠-膜及片材-厚度測定方法中的利用機械式掃描的厚度的測定方法A法所測定的膜厚（平均膜厚）。The film thickness of the color conversion film in the present invention refers to the film thickness (average film thickness) measured by the method A for measuring the thickness by mechanical scanning in the plastic-film and sheet-thickness measurement method of JIS K7130 (1999). ).

（阻擋膜） 阻擋膜（例如圖3中所示的阻擋膜12等）可適宜地用於對色變換層提昇阻氣性的情況等。作為該阻擋膜，例如可列舉：氧化矽、氧化鋁、氧化鈦、氧化鉭、氧化鋅、氧化錫、氧化銦、氧化釔、氧化鎂等無機氧化物，或氮化矽、氮化鋁、氮化鈦、碳氮化矽等無機氮化物，或該些的混合物，或向該些中添加其他元素而成的金屬氧化物薄膜或金屬氮化物薄膜，或者包含聚偏二氯乙烯、丙烯酸系樹脂、矽系樹脂、三聚氰胺系樹脂、胺基甲酸酯系樹脂、氟系樹脂、乙酸乙烯酯的皂化物等聚乙烯醇系樹脂等各種樹脂的膜。另外，作為對於水分具有阻擋功能的阻擋膜，例如可列舉：包含聚乙烯、聚丙烯、尼龍、聚偏二氯乙烯、偏二氯乙烯與氯乙烯、偏二氯乙烯與丙烯腈的共聚物、氟系樹脂、乙酸乙烯酯的皂化物等聚乙烯醇系樹脂等各種樹脂的膜。(Barrier Film) The barrier film (for example, the barrier film 12 and the like shown in FIG. 3) can be suitably used for the case where the gas barrier layer is improved in gas barrier properties and the like. Examples of the barrier film include inorganic oxides such as cerium oxide, aluminum oxide, titanium oxide, cerium oxide, zinc oxide, tin oxide, indium oxide, cerium oxide, and magnesium oxide, or cerium nitride, aluminum nitride, and nitrogen. An inorganic nitride such as titanium or niobium carbonitride, or a mixture thereof, or a metal oxide film or a metal nitride film obtained by adding other elements thereto, or comprising polyvinylidene chloride or acrylic resin A film of various resins such as a polyvinyl alcohol-based resin such as a lanthanum resin, a melamine resin, a urethane resin, a fluorine resin, or a saponified product of vinyl acetate. Further, examples of the barrier film having a barrier function against moisture include polyethylene, polypropylene, nylon, polyvinylidene chloride, vinylidene chloride and vinyl chloride, and copolymers of vinylidene chloride and acrylonitrile. A film of various resins such as a polyvinyl alcohol-based resin such as a fluorine resin or a saponified product of vinyl acetate.

阻擋膜可如圖3中所例示的阻擋膜12般設置於色變換層11的兩面上，亦可僅設置於色變換層11的一面上。另外，對應於對色變換膜所要求的功能，可進而設置光擴散層，具有抗反射功能、防眩功能、抗反射防眩功能、硬塗功能（耐摩擦功能）、抗靜電功能、防污功能、電磁波屏蔽功能、紅外線截止功能、紫外線截止功能、偏光功能、調色功能的輔助層。The barrier film may be provided on both faces of the color conversion layer 11 as in the barrier film 12 illustrated in FIG. 3, or may be provided only on one surface of the color conversion layer 11. In addition, corresponding to the function required for the color conversion film, a light diffusion layer may be further provided, and has an anti-reflection function, an anti-glare function, an anti-reflection anti-glare function, a hard coating function (friction resistance function), an antistatic function, and an antifouling function. Function, electromagnetic wave shielding function, infrared cut-off function, ultraviolet cut-off function, polarizing function, auxiliary layer of color grading function.

＜激發光＞ 激發光的種類只要是於由通式（4）所表示的化合物等所混合的發光物質可吸收的波長區域中顯示出發光者，則可使用任一種激發光。例如，不論是熱陰極管或冷陰極管、無機電致發光（EL）元件等螢光性光源、有機EL元件光源、LED光源、白熱光源、或太陽光等任一種激發光，原理上均可利用。尤其，來自LED光源的光是適宜的激發光。於顯示器或照明用途中，就可提高藍色光的色純度的觀點而言，來自具有430 nm～500 nm的波長範圍的激發光的藍色LED光源的光是更適宜的激發光。若激發光的波長範圍處於比其長的波長側，則缺乏藍色光，因此無法形成白色光，另外，若激發光的波長範圍處於比其短的波長側，則由通式（4）所表示的化合物等發光物質或黏合劑樹脂等有機化合物容易光劣化，故不佳。<Excitation Light> Any type of excitation light can be used as long as it emits light in a wavelength region that can be absorbed by a luminescent material mixed with a compound represented by the general formula (4). For example, any of the fluorescent light source such as a hot cathode tube or a cold cathode tube, an inorganic electroluminescence (EL) element, an organic EL element light source, an LED light source, a white heat source, or sunlight can be used in principle. use. In particular, light from an LED source is a suitable excitation light. In the case of display or illumination applications, from the viewpoint of improving the color purity of blue light, light from a blue LED light source having excitation light in a wavelength range of 430 nm to 500 nm is a more suitable excitation light. If the wavelength range of the excitation light is on the longer wavelength side, the blue light is absent, so that white light cannot be formed, and if the wavelength range of the excitation light is on the shorter wavelength side, it is represented by the general formula (4). An organic compound such as a luminescent material such as a compound or a binder resin is easily deteriorated by light, which is not preferable.

激發光可為具有一種發光峰值者，亦可為具有兩種以上的發光峰值者，但為了提高色純度，較佳為具有一種發光峰值者。另外，亦可將發光峰值的種類不同的多個激發光源任意地組合來使用。The excitation light may have one kind of luminescence peak, or may have two or more luminescence peaks, but in order to improve color purity, it is preferable to have one luminescence peak. Further, a plurality of excitation light sources having different types of luminescence peaks may be used arbitrarily in combination.

＜光源單元＞ 本發明的實施形態的光源單元是至少具備光源及所述色變換組成物或色變換膜的構成。當光源單元具備色變換組成物時，光源與色變換組成物的配置方法並無特別限定，可採用將色變換組成物直接塗佈於光源上的構成，亦可採用將色變換組成物塗佈於與光源分離的膜或玻璃等上的構成。當光源單元具備色變換膜時，光源與色變換膜的配置方法並無特別限定，可採用使光源與色變換膜密接的構成，亦可採用將光源與色變換膜分離的遠程螢光粉（Remote Phosphor）形式。另外，為了提高色純度，光源單元亦可採用進而具備彩色濾光片的構成。<Light source unit> The light source unit according to the embodiment of the present invention has at least a light source, a color conversion composition, or a color conversion film. When the light source unit includes the color conversion composition, the method of arranging the light source and the color conversion composition is not particularly limited, and a configuration in which the color conversion composition is directly applied to the light source may be employed, or the color conversion composition may be coated. The structure is formed on a film or glass separated from the light source. When the light source unit includes a color conversion film, the method of arranging the light source and the color conversion film is not particularly limited, and a configuration in which the light source and the color conversion film are adhered to each other may be employed, and a remote fluorescent powder that separates the light source from the color conversion film may be used ( Remote Phosphor) form. Further, in order to improve the color purity, the light source unit may have a configuration in which a color filter is further provided.

如上所述，430 nm～500 nm的波長範圍的激發光是比較小的激發能量，可防止由通式（4）所表示的化合物等發光物質的分解。因此，用於光源單元的光源較佳為於波長430 nm以上、500 nm以下的範圍內具有最大發光的發光二極體。進而，該光源較佳為於波長450 nm以上、470 nm以下的範圍具有最大發光。本發明中的光源單元可用於顯示器、照明、室內裝飾、標識、招牌等用途，可特別適宜地用於顯示器或照明用途。As described above, the excitation light in the wavelength range of 430 nm to 500 nm is a relatively small excitation energy, and decomposition of a light-emitting substance such as a compound represented by the general formula (4) can be prevented. Therefore, the light source used for the light source unit is preferably a light-emitting diode having a maximum light emission in a wavelength range of 430 nm or more and 500 nm or less. Further, the light source preferably has maximum light emission in a range of wavelengths of 450 nm or more and 470 nm or less. The light source unit in the present invention can be used for display, illumination, interior decoration, signage, signboard, etc., and can be particularly suitably used for display or lighting purposes.

＜顯示器、照明裝置＞ 本發明的實施形態的顯示器至少具備如所述般包含光源及色變換膜等的光源單元。例如，於液晶顯示器等顯示器中，使用所述光源單元作為背光單元。另外，本發明的實施形態的照明裝置至少具備如所述般包含光源及色變換膜等的光源單元。例如，該照明裝置以將作為光源單元的藍色LED光源、與使來自該藍色LED光源的藍色光變換成波長比其長的光的色變換膜或色變換組成物組合，並發出白色光的方式構成。 實施例<Display and Illumination Device> The display according to the embodiment of the present invention includes at least a light source unit including a light source, a color conversion film, and the like as described above. For example, in a display such as a liquid crystal display, the light source unit is used as a backlight unit. Further, the illumination device according to the embodiment of the present invention includes at least a light source unit including a light source, a color conversion film, and the like as described above. For example, the illumination device combines a blue LED light source as a light source unit and a color conversion film or a color conversion composition that converts blue light from the blue LED light source into light having a longer wavelength than the light source, and emits white light. The way it is composed. Example

以下，列舉實施例來說明本發明，但本發明並不由下述的實施例限定。於下述的實施例及比較例中，化合物G-1～化合物G-6、化合物R-1～化合物R-3、化合物Q-1～化合物Q-6為以下所示的化合物。Hereinafter, the present invention will be described by way of examples, but the present invention is not limited by the examples described below. In the following examples and comparative examples, the compound G-1 to the compound G-6, the compound R-1 to the compound R-3, and the compound Q-1 to the compound Q-6 are the compounds shown below.

[化45] [化45]

另外，關於實施例及比較例中的結構分析的評價方法如以下所示般。In addition, the evaluation methods of the structural analysis in the examples and the comparative examples are as follows.

＜1 H-核磁共振（Nuclear Magnetic Resonance，NMR）的測定＞ 化合物的1 H-NMR是利用超導FTNMR EX-270（日本電子股份有限公司製造），於氘代氯仿溶液中進行測定。<Measurement 1 H- NMR (Nuclear Magnetic Resonance, NMR) of> 1 H-NMR using compound superconducting FTNMR EX-270 (JEOL Co., Ltd.) was measured in deuterated chloroform solution.

＜吸收光譜的測定＞ 化合物的吸收光譜是利用U-3200形分光光度計（日立製作所股份有限公司製造），使化合物以1×10-6 mol/L的濃度溶解於甲苯中來進行測定。<Measurement of Absorption Spectrum> The absorption spectrum of the compound was measured by dissolving the compound in toluene at a concentration of 1 × 10 -6 mol/L using a U-3200 spectrophotometer (manufactured by Hitachi, Ltd.).

＜螢光光譜的測定＞ 化合物的螢光光譜是利用F-2500形分光螢光光度計（日立製作所股份有限公司製造），測定使化合物以1×10-6 mol/L的濃度溶解於甲苯中，並於波長460 nm中進行激發時的螢光光譜。<Measurement of Fluorescence Spectrum> The fluorescence spectrum of the compound was measured by dissolving the compound in toluene at a concentration of 1 × 10 -6 mol/L using an F-2500 spectrophotometer (manufactured by Hitachi, Ltd.). And the fluorescence spectrum at the time of excitation at a wavelength of 460 nm.

＜色變換特性的測定＞ 於色變換特性的測定中，於搭載有各色變換膜及藍色LED元件（普羅萊特（ProLight）公司製造；型號PM2B-3LBE-SD，發光峰值波長：460 nm）的發光裝置中流入10 mA的電流，而使該藍色LED元件點燈，並使用分光放射亮度計（CS-1000，柯尼卡美能達（Konica Minolta）公司製造）測定發光光譜、峰值波長中的發光強度及色度。再者，將各色變換膜與藍色LED元件的距離設為3 cm。<Measurement of color conversion characteristics> In the measurement of color conversion characteristics, various color conversion films and blue LED elements (manufactured by ProLight, Model No. PM2B-3LBE-SD, emission peak wavelength: 460 nm) were mounted. A current of 10 mA was flowed into the light-emitting device, and the blue LED element was turned on, and the luminescence spectrum and the peak wavelength were measured using a spectroradiometer (CS-1000, manufactured by Konica Minolta Co., Ltd.). Luminous intensity and chromaticity. Further, the distance between each color conversion film and the blue LED element was set to 3 cm.

＜光耐久性的測試＞ 於光耐久性的測試中，於搭載有各色變換膜及藍色LED元件（普羅萊特公司製造；型號PM2B-3LBE-SD，發光峰值波長：460 nm）的發光裝置中流入10 mA的電流，而使該藍色LED元件點燈，並使用分光放射亮度計（CS-1000，柯尼卡美能達公司製造）測定初期亮度。再者，將各色變換膜與藍色LED元件的距離設為3 cm。其後，於室溫下連續照射來自藍色LED元件的光，並觀測至亮度下降固定量為止的時間，藉此評價光耐久性。<Test for Light Durability> In the light durability test, a light-emitting device equipped with a color conversion film and a blue LED element (manufactured by Prolet); model PM2B-3LBE-SD, emission peak wavelength: 460 nm) was used. The current of 10 mA was flowed in, and the blue LED element was turned on, and the initial luminance was measured using a spectroradiometer (CS-1000, manufactured by Konica Minolta Co., Ltd.). Further, the distance between each color conversion film and the blue LED element was set to 3 cm. Thereafter, the light from the blue LED element was continuously irradiated at room temperature, and the time until the luminance decreased by a fixed amount was observed, thereby evaluating the light durability.

（合成例1） 以下，對本發明中的合成例1的化合物G-1的合成方法進行說明。於化合物G-1的合成方法中，將3,5-二溴苯甲醛（3.0 g）、4-第三丁基苯基硼酸（5.3 g）、四(三苯基膦)鈀（0）（0.4 g）、碳酸鉀（2.0 g）加入至燒瓶中，並進行氮氣置換。向其中添加經脫氣的甲苯（30 mL）及經脫氣的水（10 mL），並進行4小時回流。將該反應溶液冷卻至室溫為止，對有機層進行分液後利用飽和食鹽水進行清洗。利用硫酸鎂對該有機層進行乾燥，過濾後，餾去溶媒。利用矽膠層析法對所獲得的反應產物進行精製，而獲得作為白色固體的3,5-雙(4-第三丁基苯基)苯甲醛（3.5 g）。(Synthesis Example 1) Hereinafter, a method for synthesizing the compound G-1 of Synthesis Example 1 in the present invention will be described. In the synthesis method of the compound G-1, 3,5-dibromobenzaldehyde (3.0 g), 4-tert-butylphenylboronic acid (5.3 g), tetrakis(triphenylphosphine)palladium(0) ( 0.4 g), potassium carbonate (2.0 g) was added to the flask and replaced with nitrogen. Degassed toluene (30 mL) and degassed water (10 mL) were added thereto, and refluxed for 4 hours. The reaction solution was cooled to room temperature, and the organic layer was separated and washed with saturated brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The obtained reaction product was purified by silica gel chromatography to obtain 3,5-bis(4-t-butylphenyl)benzaldehyde (3.5 g) as a white solid.

繼而，將3,5-雙(4-第三丁基苯基)苯甲醛（1.5 g）與2,4-二甲基吡咯（0.7 g）加入至反應溶液中，並添加脫水二氯甲烷（200 mL）及三氟乙酸（1滴），於氮氣環境下攪拌4小時。繼而，添加2,3-二氯-5,6-二氰基-1,4-苯醌（0.85 g）的脫水二氯甲烷溶液，進而攪拌1小時。反應結束後，添加三氟化硼二乙基醚錯合物（7.0 mL）及二異丙基乙基胺（7.0 mL），攪拌4小時後，進而添加水（100 mL）並進行攪拌，然後對有機層進行分液。利用硫酸鎂對該有機層進行乾燥，過濾後，餾去溶媒。利用矽膠層析法對所獲得的反應產物進行精製，而獲得化合物（0.4 g）（產率18%）。該所獲得的化合物的1 H-NMR分析結果如下所示，確認其為化合物G-1。1 H-NMR（CDCl3 , ppm）：7.95 (s, 1H), 7.63-7.48 (m, 10H), 6.00 (s, 2H), 2.58 (s, 6H), 1.50 (s, 6H), 1.37 (s, 18H)。Then, 3,5-bis(4-t-butylphenyl)benzaldehyde (1.5 g) and 2,4-dimethylpyrrole (0.7 g) were added to the reaction solution, and dehydrated dichloromethane was added ( 200 mL) and trifluoroacetic acid (1 drop) were stirred under nitrogen for 4 hours. Then, a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.85 g) in dehydrated dichloromethane was added, followed by stirring for 1 hour. After completion of the reaction, boron trifluoride diethyl ether complex (7.0 mL) and diisopropylethylamine (7.0 mL) were added, and after stirring for 4 hours, water (100 mL) was further added and stirred, and then The organic layer was separated. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The obtained reaction product was purified by silica gel chromatography to give Compound (0.4 g) (yield: 18%). The results of 1 H-NMR analysis of the obtained compound were shown below, and it was confirmed to be Compound G-1. 1 H-NMR (CDCl 3 , ppm): 7.95 (s, 1H), 7.63-7.48 (m, 10H), 6.00 (s, 2H), 2.58 (s, 6H), 1.50 (s, 6H), 1.37 ( s, 18H).

再者，該化合物G-1的吸收光譜變成如圖4所示般，於藍色的激發光源（460 nm）中顯示出光的吸收特性。另外，該化合物G-1的螢光光譜變成如圖5所示般，於綠色區域中顯示出尖銳的發光峰值。發光量子產率顯示83%，該化合物G-1為可進行有效率的色變換的化合物。Further, the absorption spectrum of the compound G-1 was as shown in Fig. 4, and the absorption characteristics of light were exhibited in a blue excitation light source (460 nm). Further, the fluorescence spectrum of the compound G-1 became as shown in Fig. 5, and showed a sharp luminescence peak in the green region. The luminescence quantum yield showed 83%, and the compound G-1 was a compound capable of performing efficient color conversion.

（合成例2） 以下，對本發明中的合成例2的化合物R-1的合成方法進行說明。於化合物R-1的合成方法中，在氮氣氣流下，以120℃對4-(4-第三丁基苯基)-2-(4-甲氧基苯基)吡咯（300 mg）、2-甲氧基苯甲醯氯（201 mg）及甲苯（10 mL）的混合溶液進行6小時加熱。將該加熱溶液冷卻至室溫後，進行蒸發。繼而，利用乙醇（20 mL）進行清洗，進行真空乾燥後，獲得2-(2-甲氧基苯甲醯基)-3-(4-第三丁基苯基)-5-(4-甲氧基苯基)吡咯（260 mg）。(Synthesis Example 2) Hereinafter, a method for synthesizing the compound R-1 of Synthesis Example 2 in the present invention will be described. In the synthesis method of the compound R-1, 4-(4-t-butylphenyl)-2-(4-methoxyphenyl)pyrrole (300 mg), 2 at 120 ° C under a nitrogen gas stream. A mixed solution of methoxybenzamide chloride (201 mg) and toluene (10 mL) was heated for 6 hours. After the heated solution was cooled to room temperature, it was evaporated. Then, it was washed with ethanol (20 mL) and vacuum dried to obtain 2-(2-methoxybenzimidyl)-3-(4-t-butylphenyl)-5-(4-methyl Oxyphenyl)pyrrole (260 mg).

繼而，於氮氣氣流下，以125℃對2-(2-甲氧基苯甲醯基)-3-(4-第三丁基苯基)-5-(4-甲氧基苯基)吡咯（260 mg）、4-(4-第三丁基苯基)-2-(4-甲氧基苯基)吡咯（180 mg）、甲磺酸酐（206 mg）及經脫氣的甲苯（10 mL）的混合溶液進行7小時加熱。將該加熱溶液冷卻至室溫後，注入水（20 mL），並利用二氯甲烷（30 mL）對有機層進行萃取。利用水（20 mL）將該有機層清洗2次，進行蒸發，並進行真空乾燥，而獲得吡咯亞甲基體。Then, under a nitrogen gas stream, 2-(2-methoxybenzylidene)-3-(4-t-butylphenyl)-5-(4-methoxyphenyl)pyrrole at 125 °C (260 mg), 4-(4-t-butylphenyl)-2-(4-methoxyphenyl)pyrrole (180 mg), methanesulfonic anhydride (206 mg) and degassed toluene (10) The mixed solution of mL) was heated for 7 hours. After the heated solution was cooled to room temperature, water (20 mL) was poured, and the organic layer was extracted with dichloromethane (30 mL). The organic layer was washed twice with water (20 mL), evaporated, and dried in vacuo to obtain a pyrromethene.

繼而，於氮氣氣流下，向所獲得的吡咯亞甲基體與甲苯（10 mL）的混合溶液中添加二異丙基乙基胺（305 mg）及三氟化硼二乙基醚錯合物（670 mg），並於室溫下攪拌3小時。其後，注入水（20 mL），並利用二氯甲烷（30 mL）對有機層進行萃取。利用水（20 mL）將該有機層清洗2次，利用硫酸鎂進行乾燥後，進行蒸發。繼而，利用矽膠管柱層析法進行精製，進行真空乾燥後，獲得紫紅色粉末（0.27 g）。所獲得的紫紅色粉末的1 H-NMR分析結果如下所示，確認以所述方式獲得的紫紅色粉末為化合物R-1。1 H-NMR（CDCl3 , ppm）：1.19 (s, 18H), 3.42 (s, 3H), 3.85 (s, 6H), 5.72 (d, 1H), 6.20 (t, 1H), 6.42-6.97 (m, 16H), 7.89 (d, 4H)。Then, diisopropylethylamine (305 mg) and boron trifluoride diethyl ether complex were added to a mixed solution of the obtained pyrrolemethylene and toluene (10 mL) under a nitrogen gas stream. (670 mg) and stirred at room temperature for 3 hours. Thereafter, water (20 mL) was poured, and the organic layer was extracted with dichloromethane (30 mL). The organic layer was washed twice with water (20 mL), dried over magnesium sulfate, and evaporated. Then, it was purified by a silica gel column chromatography and vacuum dried to obtain a purple-red powder (0.27 g). The results of 1 H-NMR analysis of the obtained magenta powder were as follows, and it was confirmed that the magenta powder obtained in the above manner was the compound R-1. 1 H-NMR (CDCl 3 , ppm): 1.19 (s, 18H), 3.42 (s, 3H), 3.85 (s, 6H), 5.72 (d, 1H), 6.20 (t, 1H), 6.42-6.97 ( m, 16H), 7.89 (d, 4H).

再者，該化合物R-1的吸收光譜變成如圖6所示般，於藍色及綠色的激發光源中顯示出光的吸收特性。另外，該化合物R-1的螢光光譜變成如圖7所示般，於紅色區域中顯示出尖銳的發光峰值。發光量子產率顯示90%，該化合物R-1為可進行有效率的色變換的化合物。Further, the absorption spectrum of the compound R-1 was as shown in Fig. 6, and the absorption characteristics of light were exhibited in the blue and green excitation light sources. Further, the fluorescence spectrum of the compound R-1 showed a sharp luminescence peak in the red region as shown in Fig. 7 . The luminescence quantum yield showed 90%, and the compound R-1 was a compound capable of performing efficient color conversion.

（實施例1） 於本發明的實施例1中，使用矽酮樹脂「OE-6630A/B」（東麗・道康寧公司製造）作為（B）成分，相對於該（B）成分的100重量份，混合0.20重量份的作為（A）成分的化合物G-1、0.5重量份的硬化劑、1.0重量份的作為（C）成分的化合物Q-1。其後，使用行星式攪拌・脫泡裝置「瑪澤斯塔（Mazerustar）KK-400」（倉敷紡織（Kurabo）製造），以1000 rpm對該些的混合物進行20分鐘攪拌・脫泡，藉此獲得作為膜製作用樹脂液的色變換組成物。(Example 1) In Example 1 of the present invention, an oxime resin "OE-6630A/B" (manufactured by Toray Dow Corning Co., Ltd.) was used as the component (B), and 100 parts by weight of the component (B). 0.20 parts by weight of the compound G-1 as the component (A), 0.5 part by weight of a curing agent, and 1.0 part by weight of the compound Q-1 as the component (C) were mixed. Then, using a planetary stirring/deaerator "Mazerustar KK-400" (manufactured by Kurabo), the mixture was stirred and defoamed at 1000 rpm for 20 minutes. A color conversion composition as a resin liquid for film production was obtained.

繼而，使用縫模塗佈機，將該膜製作用樹脂液塗佈於「賽拉皮爾（Cerapeel）」BLK（東麗膜加工股份有限公司製造）上，並於130℃下進行2小時加熱、乾燥，而獲得膜厚為200 μm的色變換膜。Then, the resin liquid for film production was applied to "Cerapeel" BLK (manufactured by Toray Film Processing Co., Ltd.) using a slot coater, and heated at 130 ° C for 2 hours. Drying was carried out to obtain a color conversion film having a film thickness of 200 μm.

利用該色變換膜來使藍色LED光進行色變換的結果是，若僅選取綠色光的發光區域，則可獲得峰值波長為526 nm、峰值波長中的發光光譜的半寬度為25 nm的高色純度綠色發光。另外，於室溫下連續照射來自藍色LED元件的光的結果是，亮度下降5%的時間為105小時。將實施例1的評價結果、（A）成分及（C）成分示於後述的表2中。As a result of color conversion of the blue LED light by the color conversion film, if only the light-emitting region of the green light is selected, a peak wavelength of 526 nm and a half-width of the emission spectrum in the peak wavelength of 25 nm can be obtained. The color purity is green. Further, as a result of continuously irradiating light from the blue LED element at room temperature, the time during which the luminance was decreased by 5% was 105 hours. The evaluation results of the first embodiment, the components (A) and (C) are shown in Table 2 to be described later.

（實施例2～實施例8及比較例1～比較例6） 於本發明的實施例2～實施例8及相對於本發明的比較例1～比較例6中，使用表2中所記載的有機發光材料（化合物G-1、化合物G-2、化合物G-3、化合物G-4）作為（A）成分，並適宜使用表2中所記載的胺衍生物（化合物Q-1、化合物Q-2、化合物Q-3、化合物Q-4、化合物Q-5、化合物Q-6）作為（C）成分，除此以外，以與實施例1相同的方式製作色變換膜並進行評價。將實施例2～實施例8及比較例1～比較例6的評價結果示於表2中。(Examples 2 to 8 and Comparative Examples 1 to 6) In Examples 2 to 8 of the present invention and Comparative Examples 1 to 6 of the present invention, the conditions described in Table 2 were used. The organic light-emitting material (compound G-1, compound G-2, compound G-3, and compound G-4) is used as the component (A), and the amine derivative (compound Q-1, compound Q) shown in Table 2 is suitably used. A color conversion film was produced and evaluated in the same manner as in Example 1 except that the compound Q-3, the compound Q-4, the compound Q-5, and the compound Q-6) were used as the component (C). The evaluation results of Examples 2 to 8 and Comparative Examples 1 to 6 are shown in Table 2.

（實施例9） 於本發明的實施例9中，使用二液型熱硬化性環氧系丙烯酸樹脂作為（B）成分，相對於該（B）成分的100重量份，混合0.08重量份的作為（A）成分的化合物R-1、0.5重量份的硬化劑、1.0重量份的作為（C）成分的化合物Q-1。其後，以300 rpm對該些的混合物進行1小時攪拌等，而製作色變換組成物。(Example 9) In the ninth embodiment of the present invention, a two-component thermosetting epoxy-based acrylic resin is used as the component (B), and 0.08 parts by weight is mixed with 100 parts by weight of the component (B). The compound R-1 of the component (A), 0.5 part by weight of a curing agent, and 1.0 part by weight of the compound Q-1 as the component (C). Thereafter, the mixture was stirred at 300 rpm for 1 hour to prepare a color conversion composition.

繼而，利用棒塗方式將該色變換組成物塗佈於延伸聚乙烯對苯二甲酸膜（東麗先進材料（Toray Advanced Materials）股份有限公司製造的XG5P1）上後，於120℃下進行5分鐘乾燥。藉此，形成平均膜厚為10 μm的塗佈層。其後，將擴散膜（東麗先進材料股份有限公司製造的「泰克斯賽爾（Texcell）」（註冊商標）TDF127）層壓於該塗佈層上後，於60℃下進行1小時老化，而獲得色變換膜。Then, the color conversion composition was applied to an extended polyethylene terephthalic acid film (XG5P1 manufactured by Toray Advanced Materials Co., Ltd.) by a bar coating method, and then subjected to 5 minutes at 120 ° C. dry. Thereby, a coating layer having an average film thickness of 10 μm was formed. Thereafter, a diffusion film ("Texcell" (registered trademark) TDF127 manufactured by Toray Advanced Materials Co., Ltd.) was laminated on the coating layer, and then aged at 60 ° C for 1 hour. A color conversion film was obtained.

利用該色變換膜來使藍色LED光進行色變換的結果是，若僅選取紅色光的發光區域，則可獲得峰值波長為635 nm、峰值波長中的發光光譜的半寬度為49 nm的高色純度紅色發光。另外，於室溫下連續照射來自藍色LED元件的光的結果是，亮度下降2%的時間為400小時。將實施例9的評價結果、（A）成分及（C）成分示於後述的表3中。As a result of color conversion of the blue LED light by the color conversion film, if only the light-emitting region of the red light is selected, a peak wavelength of 635 nm and a half-width of the emission spectrum in the peak wavelength of 49 nm can be obtained. The color purity is red. Further, as a result of continuously irradiating light from the blue LED element at room temperature, the time during which the luminance was decreased by 2% was 400 hours. The evaluation results of Example 9, the components (A) and (C) are shown in Table 3 which will be described later.

（實施例10～實施例15及比較例7～比較例10） 於本發明的實施例10～實施例15及相對於本發明的比較例7～比較例10中，使用表3中所記載的有機發光材料（化合物R-1、化合物R-2、化合物R-3）作為（A）成分，並適宜使用表3中所記載的胺衍生物（化合物Q-1、化合物Q-2、化合物Q-3、化合物Q-4、化合物Q-5、化合物Q-6）作為（C）成分，除此以外，以與實施例9相同的方式製作色變換膜並進行評價。將實施例10～實施例15及比較例7～比較例10的評價結果示於表3中。(Examples 10 to 15 and Comparative Examples 7 to 10) In Examples 10 to 15 of the present invention and Comparative Examples 7 to 10 of the present invention, the contents described in Table 3 were used. The organic light-emitting material (compound R-1, compound R-2, and compound R-3) is used as the component (A), and the amine derivative described in Table 3 (compound Q-1, compound Q-2, compound Q) is suitably used. A color conversion film was produced and evaluated in the same manner as in Example 9 except that the compound Q-4, the compound Q-5, and the compound Q-6) were used as the component (C). The evaluation results of Examples 10 to 15 and Comparative Examples 7 to 10 are shown in Table 3.

（實施例16） 於本發明的實施例16中，使用二液型熱硬化性環氧系丙烯酸樹脂作為（B）成分，相對於該（B）成分的100重量份，混合0.20重量份的作為（A）成分的發光材料（a）的化合物G-1、0.08重量份的作為（A）成分的發光材料（b）的化合物R-1、0.5重量份的硬化劑、1.0重量份的作為（C）成分的化合物Q-1。其後，以300 rpm對該些的混合物進行1小時攪拌等，而製作色變換組成物。(Example 16) In Example 16 of the present invention, a two-component thermosetting epoxy-based acrylic resin was used as the component (B), and 0.20 part by weight was mixed with 100 parts by weight of the component (B). Compound G-1 of the light-emitting material (a) of the component (A), 0.08 parts by weight of the compound R-1 as the light-emitting material (b) of the component (A), 0.5 part by weight of a curing agent, and 1.0 part by weight of ( Compound Q-1 of component C). Thereafter, the mixture was stirred at 300 rpm for 1 hour to prepare a color conversion composition.

繼而，利用棒塗方式將該色變換組成物塗佈於延伸聚乙烯對苯二甲酸膜（東麗先進材料股份有限公司製造的XG5P1）上後，於120℃下進行5分鐘乾燥。藉此，形成平均膜厚為10 μm的塗佈層。其後，將擴散膜（東麗先進材料股份有限公司製造的「泰克斯賽爾（Texcell）」（註冊商標）TDF127）層壓於該塗佈層上後，於60℃下進行1小時老化，而獲得色變換膜。Then, the color conversion composition was applied onto a stretched polyethylene terephthalate film (XG5P1 manufactured by Toray Advanced Materials Co., Ltd.) by a bar coating method, and then dried at 120 ° C for 5 minutes. Thereby, a coating layer having an average film thickness of 10 μm was formed. Thereafter, a diffusion film ("Texcell" (registered trademark) TDF127 manufactured by Toray Advanced Materials Co., Ltd.) was laminated on the coating layer, and then aged at 60 ° C for 1 hour. A color conversion film was obtained.

利用該色變換膜來使藍色LED光進行色變換的結果是，若僅選綠色光的發光區域，則可獲得峰值波長為527 nm、峰值波長中的發光光譜的半寬度為28 nm的高色純度綠色發光，若僅選紅色光的發光區域，則可獲得峰值波長為635 nm、峰值波長中的發光光譜的半寬度為49 nm的高色純度紅色發光。另外，於室溫下連續照射來自藍色LED元件的光的結果是，亮度下降5%的時間為110小時。將實施例16的評價結果、（A）成分及（C）成分示於後述的表4中。As a result of color conversion of the blue LED light by the color conversion film, if only the light-emitting region of the green light is selected, the peak wavelength is 527 nm, and the half-width of the emission spectrum in the peak wavelength is 28 nm. The color purity is green, and if only the light-emitting region of red light is selected, a high-color purity red light having a peak wavelength of 635 nm and a half-width of the light-emitting spectrum in the peak wavelength of 49 nm can be obtained. Further, as a result of continuously irradiating light from the blue LED element at room temperature, the time during which the luminance was decreased by 5% was 110 hours. The evaluation results of Example 16, the components (A) and (C) are shown in Table 4 which will be described later.

（實施例17～實施例21及比較例11、比較例12） 於本發明的實施例17～實施例21及相對於本發明的比較例11、比較例12中，使用表4中所記載的發光材料（a）（化合物G-1、化合物G-2、化合物G-3、化合物G-4）及發光材料（b）（化合物R-1、化合物R-2、化合物R-3）作為（A）成分，並適宜使用表4中所記載的胺衍生物（化合物Q-1、化合物Q-6）作為（C）成分，除此以外，以與實施例16相同的方式製作色變換膜並進行評價。將實施例17～實施例21及比較例11、比較例12的評價結果示於表4中。(Examples 17 to 21, Comparative Example 11, and Comparative Example 12) In Examples 17 to 21 of the present invention and Comparative Example 11 and Comparative Example 12 of the present invention, the results described in Table 4 were used. The luminescent material (a) (compound G-1, compound G-2, compound G-3, compound G-4) and the luminescent material (b) (compound R-1, compound R-2, compound R-3) are used as A color conversion film was produced in the same manner as in Example 16 except that the amine derivative (Compound Q-1, Compound Q-6) described in Table 4 was used as the component (C). Conduct an evaluation. The evaluation results of Examples 17 to 21, Comparative Example 11, and Comparative Example 12 are shown in Table 4.

（實施例22） 於本發明的實施例22中，使用丙烯酸樹脂「KC-7000」（共榮社化學股份有限公司製造）作為（B）成分，相對於該（B）成分的100重量份，混合0.25重量份的作為（A）成分的化合物G-5、1.0重量份的作為（C）成分的化合物Q-1。其後，以300 rpm對該些的混合物進行1小時攪拌等，而製作色變換組成物。(Example 22) In Example 22 of the present invention, an acrylic resin "KC-7000" (manufactured by Kyoeisha Chemical Co., Ltd.) was used as the component (B), and 100 parts by weight of the component (B) was used. 0.25 parts by weight of the compound G-5 as the component (A) and 1.0 part by weight of the compound Q-1 as the component (C) were mixed. Thereafter, the mixture was stirred at 300 rpm for 1 hour to prepare a color conversion composition.

繼而，利用棒塗方式將該色變換組成物塗佈於聚對苯二甲酸乙二酯膜（東麗股份有限公司製造的U48）上後，於120℃下進行5分鐘乾燥。藉此，形成平均膜厚為16 μm的色變換層。其後，將擴散膜（東麗先進材料股份有限公司製造的「泰克斯賽爾（Texcell）」（註冊商標）TDF127）層壓於該塗佈層上後，於60℃下進行1小時老化，而獲得色變換膜。Then, the color conversion composition was applied onto a polyethylene terephthalate film (U48 manufactured by Toray Industries, Inc.) by a bar coating method, and then dried at 120 ° C for 5 minutes. Thereby, a color conversion layer having an average film thickness of 16 μm was formed. Thereafter, a diffusion film ("Texcell" (registered trademark) TDF127 manufactured by Toray Advanced Materials Co., Ltd.) was laminated on the coating layer, and then aged at 60 ° C for 1 hour. A color conversion film was obtained.

利用該色變換膜來使藍色LED光進行色變換的結果是，若僅選綠色光的發光區域，則可獲得峰值波長為529 nm、峰值波長中的發光光譜的半寬度為26 nm的高色純度綠色發光。實施例22的峰值波長中的發光強度為將後述的比較例13中的發光強度設為1.00時的相對值。具體而言，於實施例22中，峰值波長中的發光強度為1.00，未看見由（C）成分所引起的發光的阻礙。另外，於室溫下連續照射來自藍色LED元件的光的結果是，亮度下降5%的時間為260小時。將實施例22的評價結果、（A）成分及（C）成分示於後述的表5中。As a result of color conversion of the blue LED light by the color conversion film, if only the light-emitting region of the green light is selected, the peak wavelength is 529 nm, and the half-width of the emission spectrum in the peak wavelength is 26 nm. The color purity is green. The luminescence intensity in the peak wavelength of Example 22 is a relative value when the luminescence intensity in Comparative Example 13 to be described later is 1.00. Specifically, in Example 22, the luminescence intensity in the peak wavelength was 1.00, and the hindrance of luminescence caused by the component (C) was not observed. Further, as a result of continuously irradiating light from the blue LED element at room temperature, the time during which the luminance was decreased by 5% was 260 hours. The evaluation results of Example 22, the components (A) and (C) are shown in Table 5 to be described later.

（實施例23～實施例25及比較例13、比較例14） 於本發明的實施例23～實施例25及相對於本發明的比較例13、比較例14中，使用表5中所記載的有機發光材料（化合物G-5、化合物G-6）作為（A）成分，並適宜使用表5中所記載的胺衍生物（化合物Q-1、化合物Q-2）作為（C）成分，除此以外，以與實施例22相同的方式製作色變換膜並進行評價。將實施例23～實施例25及比較例13、比較例14的評價結果示於表5中。但是，表5中的發光強度（相對值）為將比較例13中的發光強度設為1.00時的相對值。(Examples 23 to 25, Comparative Example 13, and Comparative Example 14) In Examples 23 to 25 of the present invention and Comparative Example 13 and Comparative Example 14 of the present invention, the results described in Table 5 were used. The organic light-emitting material (compound G-5, compound G-6) is used as the component (A), and the amine derivative (compound Q-1, compound Q-2) described in Table 5 is suitably used as the component (C). A color conversion film was produced and evaluated in the same manner as in Example 22 except for the above. The evaluation results of Examples 23 to 25, Comparative Example 13, and Comparative Example 14 are shown in Table 5. However, the luminescence intensity (relative value) in Table 5 is a relative value when the luminescence intensity in Comparative Example 13 was 1.00.

[表2] （表2） [Table 2] (Table 2)

[表3] （表3） [Table 3] (Table 3)

[表4] （表4） [Table 4] (Table 4)

[表5] （表5） [產業上之可利用性][Table 5] (Table 5) [Industrial availability]

如以上般，本發明的色變換組成物、色變換膜、含有其的光源單元、顯示器及照明裝置對於色彩再現性的提昇與高耐久性的併存有用，尤其適合於使高色純度的發光與高耐久性併存的色變換組成物、色變換膜、含有其的光源單元、顯示器及照明裝置。As described above, the color conversion composition, the color conversion film, the light source unit including the same, the display, and the illumination device of the present invention are useful for enhancing the color reproducibility and high durability, and are particularly suitable for high-color purity illumination and A color conversion composition, a color conversion film, a light source unit including the same, a display, and a lighting device with high durability.

1‧‧‧色變換膜
10‧‧‧基材層
11‧‧‧色變換層
12‧‧‧阻擋膜1‧‧‧Color conversion film
10‧‧‧Substrate layer
11‧‧‧Color conversion layer
12‧‧‧Block film

圖1是表示本發明的實施形態的色變換膜的一例的示意剖面圖。 圖2是表示本發明的實施形態的色變換膜的另一例的示意剖面圖。 圖3是表示本發明的實施形態的色變換膜的又一例的示意剖面圖。 圖4是例示本發明的實施例中的合成例1的化合物的吸收光譜的圖。 圖5是例示本發明的實施例中的合成例1的化合物的發光光譜的圖。 圖6是例示本發明的實施例中的合成例2的化合物的吸收光譜的圖。 圖7是例示本發明的實施例中的合成例2的化合物的發光光譜的圖。Fig. 1 is a schematic cross-sectional view showing an example of a color conversion film according to an embodiment of the present invention. Fig. 2 is a schematic cross-sectional view showing another example of the color conversion film according to the embodiment of the present invention. 3 is a schematic cross-sectional view showing still another example of the color conversion film according to the embodiment of the present invention. 4 is a view illustrating an absorption spectrum of a compound of Synthesis Example 1 in Examples of the present invention. Fig. 5 is a graph illustrating the luminescence spectrum of the compound of Synthesis Example 1 in the examples of the present invention. Fig. 6 is a graph illustrating the absorption spectrum of the compound of Synthesis Example 2 in the examples of the present invention. Fig. 7 is a view showing the luminescence spectrum of the compound of Synthesis Example 2 in the Example of the present invention.

1‧‧‧色變換膜 1‧‧‧Color conversion film

10‧‧‧基材層 10‧‧‧Substrate layer

11‧‧‧色變換層 11‧‧‧Color conversion layer

Claims (20)

一種色變換組成物，其將入射光變換成波長比所述入射光長的光，其特徵在於： 包括以下的（A）成分、（B）成分及（C）成分， （A）成分：至少一種的有機發光材料 （B）成分：黏合劑樹脂 （C）成分：具有由通式（1）所表示的部分結構的胺衍生物通式（1）中，R10 ～R14 分別可相同，亦可不同，且自氫原子、烷基、環烷基、芳基、雜芳基中選擇；其中，R11 與R12 的至少一者及R13 與R14 的至少一者不為氫原子。A color conversion composition that converts incident light into light having a longer wavelength than the incident light, and includes: (A) component, (B) component, and (C) component, and (A) component: at least Organic light-emitting material (B) component: binder resin (C) component: amine derivative having a partial structure represented by the general formula (1) In the formula (1), R 10 to R 14 may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R 11 and R 12 are at least One and at least one of R 13 and R 14 are not a hydrogen atom. 如申請專利範圍第1項所述的色變換組成物，其中所述（C）成分為具有由通式（2）所表示的哌啶骨架的化合物，通式（2）中，R10 ～R14 與所述通式（1）相同。The color conversion composition according to claim 1, wherein the component (C) is a compound having a piperidine skeleton represented by the formula (2), In the formula (2), R 10 to R 14 are the same as those in the above formula (1). 如申請專利範圍第1項或第2項所述的色變換組成物，其中所述（C）成分為由通式（3）所表示的化合物，通式（3）中，R10 ～R14 與所述通式（1）相同；m為10以下的自然數；Y自單鍵、鏈狀或環狀的脂肪族烴、脂肪族雜環、芳香族烴環、芳香族雜環、或該些的組合中選擇。The color conversion composition according to Item 1 or 2, wherein the component (C) is a compound represented by the formula (3), In the formula (3), R 10 to R 14 are the same as the above formula (1); m is a natural number of 10 or less; Y is a single bond, a chain or a cyclic aliphatic hydrocarbon, or an aliphatic heterocyclic ring; An aromatic hydrocarbon ring, an aromatic hetero ring, or a combination of these is selected. 如申請專利範圍第3項所述的色變換組成物，其中所述通式（3）的Y為鏈狀或環狀的脂肪族烴、苯環、或該些的組合。The color conversion composition according to claim 3, wherein Y of the formula (3) is a chain or cyclic aliphatic hydrocarbon, a benzene ring, or a combination thereof. 如申請專利範圍第1項或第2項所述的色變換組成物，其中所述R10 為烷基。The color conversion composition according to claim 1 or 2, wherein the R 10 is an alkyl group. 如申請專利範圍第1項或第2項所述的色變換組成物，其中相對於所述（B）成分的100重量份，所述（C）成分的含量為1.0×10-2 重量份以上、10重量份以下。The color conversion composition according to Item 1 or 2, wherein the content of the component (C) is 1.0 × 10 -2 parts by weight or more based on 100 parts by weight of the component (B). 10 parts by weight or less. 如申請專利範圍第1項或第2項所述的色變換組成物，其中所述（A）成分含有由通式（4）所表示的化合物，通式（4）中，X為C-R7 或N；R1 ～R9 分別可相同，亦可不同，自氫、烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基、及與鄰接取代基之間所形成的縮合環及脂肪族環中選擇。The color conversion composition according to the first or second aspect of the invention, wherein the component (A) contains a compound represented by the formula (4), In the formula (4), X is CR 7 or N; and R 1 to R 9 may be the same or different, and may be different from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl or alkynyl. , hydroxy, thiol, alkoxy, alkylthio, aryl ether, aryl sulfide, aryl, heteroaryl, halogen, cyano, aldehyde, carbonyl, carboxyl, oxycarbonyl, amine formazan A condensed ring and an aliphatic ring formed between a group, an amine group, a nitro group, a decyl group, a decyloxy group, a boron boron group, a phosphine oxide group, and a contiguous substituent are selected. 如申請專利範圍第7項所述的色變換組成物，其中所述通式（4）的X為C-R7 ，所述R7 為由通式（5）所表示的基，通式（5）中，r選自由氫、烷基、環烷基、雜環基、烯基、環烯基、炔基、羥基、硫醇基、烷氧基、烷硫基、芳醚基、芳基硫醚基、芳基、雜芳基、鹵素、氰基、醛基、羰基、羧基、氧羰基、胺甲醯基、胺基、硝基、矽烷基、矽氧烷基、氧硼基、氧化膦基所組成的群組；k為1～3的整數；當k為2以上時，r分別可相同，亦可不同。The color conversion composition according to claim 7 , wherein X of the general formula (4) is CR 7 , and the R 7 is a group represented by the general formula (5). In the formula (5), r is selected from hydrogen, alkyl, cycloalkyl, heterocyclic, alkenyl, cycloalkenyl, alkynyl, hydroxy, thiol, alkoxy, alkylthio, aryl ether , aryl sulfide group, aryl group, heteroaryl group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl group, oxycarbonyl group, amine methyl group, amine group, nitro group, decyl group, decyloxy group, boron boron a group consisting of a phosphine oxide group; k is an integer of 1-3; and when k is 2 or more, r may be the same or different. 如申請專利範圍第7項所述的色變換組成物，其中所述通式（4）的R1 、R3 、R4 及R6 分別可相同，亦可不同，且為經取代或未經取代的苯基。The color conversion composition according to claim 7, wherein R 1 , R 3 , R 4 and R 6 of the formula (4) are respectively the same or different, and are substituted or not. Substituted phenyl. 如申請專利範圍第7項所述的色變換組成物，其中所述通式（4）的R1 、R3 、R4 及R6 分別可相同，亦可不同，且為經取代或未經取代的烷基。The color conversion composition according to claim 7, wherein R 1 , R 3 , R 4 and R 6 of the formula (4) are respectively the same or different, and are substituted or not. Substituted alkyl. 如申請專利範圍第1項或第2項所述的色變換組成物，其中所述（A）成分含有藉由使用波長430 nm以上、500 nm以下的範圍的激發光，而呈現於峰值波長為500 nm以上、580 nm以下的區域中所觀測到的發光的發光材料。The color conversion composition according to the first or second aspect of the invention, wherein the component (A) contains excitation light in a range of 430 nm or more and 500 nm or less, and the peak wavelength is Luminescent luminescent materials observed in regions above 500 nm and below 580 nm. 如申請專利範圍第1項或第2項所述的色變換組成物，其中所述（A）成分含有以下的發光材料（a）及發光材料（b）， 發光材料（a）：藉由使用波長430 nm以上、500 nm以下的範圍的激發光，而呈現於峰值波長為500 nm以上、580 nm以下的區域中所觀測到的發光的發光材料 發光材料（b）：藉由波長430 nm以上，500 nm以下的範圍的激發光及來自所述發光材料（a）的發光的至少一者而得到激發，藉此呈現於峰值波長為580 nm以上、750 nm以下的區域中所觀測到的發光的發光材料。The color conversion composition according to claim 1 or 2, wherein the component (A) comprises the following luminescent material (a) and luminescent material (b), and the luminescent material (a): by using Luminescent material luminescent material (b) exhibiting luminescence in a region having a peak wavelength of 500 nm or more and 580 nm or less at a wavelength of 430 nm or more and 500 nm or less: by a wavelength of 430 nm or more At least one of excitation light in a range of 500 nm or less and luminescence from the luminescent material (a) is excited, thereby exhibiting luminescence observed in a region having a peak wavelength of 580 nm or more and 750 nm or less. Luminescent material. 如申請專利範圍第12項所述的色變換組成物，其中所述發光材料（a）的含量wa 與所述發光材料（b）的含量wb 為wa ≧wb 的關係。The color conversion composition according to claim 12, wherein the content w a of the luminescent material (a) and the content w b of the luminescent material (b) are w a ≧ w b . 如申請專利範圍第7項所述的色變換組成物，其中所述（A）成分含有藉由使用波長430 nm以上、500 nm以下的範圍的激發光，而呈現峰值波長為500 nm以上、580 nm以下的發光的發光材料，且 所述發光材料為由所述通式（4）所表示的化合物。The color conversion composition according to claim 7, wherein the component (A) contains excitation light having a wavelength of 430 nm or more and 500 nm or less, and exhibits a peak wavelength of 500 nm or more and 580. A light-emitting luminescent material of nm or less, and the luminescent material is a compound represented by the above formula (4). 如申請專利範圍第7項所述的色變換組成物，其中所述（A）成分含有以下的發光材料（a）及發光材料（b），且 所述發光材料（b）為由所述通式（4）所表示的化合物， 發光材料（a）：藉由使用波長430 nm以上、500 nm以下的範圍的激發光，而呈現於峰值波長為500 nm以上、580 nm以下的區域中所觀測到的發光的發光材料 發光材料（b）：藉由波長430 nm以上，500 nm以下的範圍的激發光及來自所述發光材料（a）的發光的至少一者而得到激發，藉此呈現於峰值波長為580 nm以上、750 nm以下的區域中所觀測到的發光的發光材料。The color conversion composition according to claim 7, wherein the component (A) comprises the following luminescent material (a) and luminescent material (b), and the luminescent material (b) is The compound represented by the formula (4), the luminescent material (a): is observed in a region having a peak wavelength of 500 nm or more and 580 nm or less by using excitation light having a wavelength of 430 nm or more and 500 nm or less. The emitted luminescent material luminescent material (b) is excited by at least one of excitation light having a wavelength of 430 nm or more and 500 nm or less and luminescence from the luminescent material (a), thereby being expressed by A luminescent material having a peak wavelength of 580 nm or more and 750 nm or less. 一種色變換膜，其特徵在於包括含有以下的（A）成分、（B）成分及（C）成分，並將入射光變換成波長比所述入射光長的光的色變換組成物的硬化物層， （A）成分：至少一種的有機發光材料 （B）成分：黏合劑樹脂 （C）成分：具有由通式（1）所表示的部分結構的胺衍生物通式（1）中，R10 ～R14 分別可相同，亦可不同，且自氫原子、烷基、環烷基、芳基、雜芳基中選擇；其中，R11 與R12 的至少一者及R13 與R14 的至少一者不為氫原子。A color conversion film comprising a cured product of a color conversion composition containing the following (A) component, (B) component, and (C) component and converting incident light into light having a longer wavelength than the incident light; Layer, component (A): at least one organic light-emitting material (B) component: binder resin (C) component: amine derivative having a partial structure represented by the general formula (1) In the formula (1), R 10 to R 14 may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R 11 and R 12 are at least One and at least one of R 13 and R 14 are not a hydrogen atom. 一種光源單元，其特徵在於包括： 光源；以及 色變換膜，包含含有以下的（A）成分、（B）成分及（C）成分，並將入射光變換成波長比所述入射光長的光的色變換組成物的硬化物層； （A）成分：至少一種的有機發光材料 （B）成分：黏合劑樹脂 （C）成分：具有由通式（1）所表示的部分結構的胺衍生物通式（1）中，R10 ～R14 分別可相同，亦可不同，且自氫原子、烷基、環烷基、芳基、雜芳基中選擇；其中，R11 與R12 的至少一者及R13 與R14 的至少一者不為氫原子。A light source unit comprising: a light source; and a color conversion film including the following components (A), (B), and (C), and converting incident light into light having a longer wavelength than the incident light (A) component: at least one organic light-emitting material (B) component: binder resin (C) component: an amine derivative having a partial structure represented by the general formula (1) In the formula (1), R 10 to R 14 may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R 11 and R 12 are at least One and at least one of R 13 and R 14 are not a hydrogen atom. 如申請專利範圍第17項所述的光源單元，其中所述光源為於波長430 nm以上、500 nm以下的範圍內具有最大發光的發光二極體。The light source unit according to claim 17, wherein the light source is a light-emitting diode having a maximum light emission in a wavelength range of 430 nm or more and 500 nm or less. 一種顯示器，其特徵在於包括光源單元，所述光源單元包括：光源；以及色變換膜，包含含有以下的（A）成分、（B）成分及（C）成分，並將入射光變換成波長比所述入射光長的光的色變換組成物的硬化物層； （A）成分：至少一種的有機發光材料 （B）成分：黏合劑樹脂 （C）成分：具有由通式（1）所表示的部分結構的胺衍生物通式（1）中，R10 ～R14 分別可相同，亦可不同，且自氫原子、烷基、環烷基、芳基、雜芳基中選擇；其中，R11 與R12 的至少一者及R13 與R14 的至少一者不為氫原子。A display comprising a light source unit, the light source unit comprising: a light source; and a color conversion film comprising the following components (A), (B), and (C), and converting the incident light into a wavelength ratio a hardened material layer of the color conversion composition of the light having a long incident light; (A) component: at least one organic light-emitting material (B) component: a binder resin (C) component: having a formula (1) Partial structure of amine derivatives In the formula (1), R 10 to R 14 may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R 11 and R 12 are at least One and at least one of R 13 and R 14 are not a hydrogen atom. 一種照明裝置，其特徵在於包括光源單元，所述光源單元包括：光源；以及色變換膜，包含含有以下的（A）成分、（B）成分及（C）成分，並將入射光變換成波長比所述入射光長的光的色變換組成物的硬化物層； （A）成分：至少一種的有機發光材料 （B）成分：黏合劑樹脂 （C）成分：具有由通式（1）所表示的部分結構的胺衍生物通式（1）中，R10 ～R14 分別可相同，亦可不同，且自氫原子、烷基、環烷基、芳基、雜芳基中選擇；其中，R11 與R12 的至少一者及R13 與R14 的至少一者不為氫原子。A lighting device characterized by comprising a light source unit, the light source unit comprising: a light source; and a color conversion film comprising the following components (A), (B) and (C), and converting the incident light into a wavelength a cured layer of a color conversion composition of light longer than the incident light; (A) component: at least one organic light-emitting material (B) component: binder resin (C) component: having a formula (1) Partial structure of amine derivatives In the formula (1), R 10 to R 14 may be the same or different and selected from a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a heteroaryl group; wherein at least R 11 and R 12 are at least One and at least one of R 13 and R 14 are not a hydrogen atom.
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