JP2023151257A - Phosphor dispersion, and phosphor photosensitive composition using the same - Google Patents
Phosphor dispersion, and phosphor photosensitive composition using the same Download PDFInfo
- Publication number
- JP2023151257A JP2023151257A JP2022060772A JP2022060772A JP2023151257A JP 2023151257 A JP2023151257 A JP 2023151257A JP 2022060772 A JP2022060772 A JP 2022060772A JP 2022060772 A JP2022060772 A JP 2022060772A JP 2023151257 A JP2023151257 A JP 2023151257A
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- Japan
- Prior art keywords
- phosphor
- modified silicone
- dispersion
- photosensitive composition
- dispersant
- Prior art date
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 164
- 239000000203 mixture Substances 0.000 title claims abstract description 102
- 239000006185 dispersion Substances 0.000 title claims abstract description 65
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 77
- 239000003960 organic solvent Substances 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000003999 initiator Substances 0.000 claims abstract description 16
- 239000002270 dispersing agent Substances 0.000 claims description 58
- 229920002050 silicone resin Polymers 0.000 claims description 35
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229920005989 resin Polymers 0.000 abstract description 10
- 239000011347 resin Substances 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 27
- 230000000052 comparative effect Effects 0.000 description 20
- 150000002430 hydrocarbons Chemical group 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- 239000002245 particle Substances 0.000 description 18
- 229920000178 Acrylic resin Polymers 0.000 description 15
- 239000004925 Acrylic resin Substances 0.000 description 15
- -1 acrylate ester Chemical class 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
Abstract
Description
本発明は、蛍光体感光性組成物に関するものである。より詳しくは、有機ＥＬディスプレイ、マイクロＬＥＤディスプレイにおける波長変換層に使用するための蛍光体感光性組成物に関するものである。 The present invention relates to a phosphor photosensitive composition. More specifically, the present invention relates to a phosphor photosensitive composition for use in a wavelength conversion layer in an organic EL display or a micro LED display.
近年、発光ダイオード（ＬＥＤ）が急速に普及している。ＬＥＤは、テレビ、パソコン、タブレット、スマートフォン等のディスプレイや照明等に利用される。ＬＥＤを利用した画像表示装置は、光の透過、非透過を切り替える液晶を用いずに表示を行うことができる。このため、ＬＥＤを利用した画像表示装置は、黒表示時に光漏れが生じることが課題であった液晶表示装置と比較して、暗所での視認性に特に優れる。 In recent years, light emitting diodes (LEDs) have rapidly become popular. LEDs are used in displays and lighting for televisions, computers, tablets, smartphones, etc. An image display device using LEDs can perform display without using a liquid crystal that switches between light transmission and non-transmission. For this reason, image display devices using LEDs are particularly superior in visibility in dark places, compared to liquid crystal display devices that suffer from light leakage when displaying black.
マイクロＬＥＤディスプレイは、およそ２μｍから５０μｍサイズのＬＥＤチップがマトリクス状に配列した構造を有し、複数のＬＥＤの各々を個別駆動することによって表示を行う画像表示装置である。このようなマイクロＬＥＤディスプレイは、液晶を用いずに表示を行うことができる。 A micro LED display is an image display device that has a structure in which LED chips with a size of about 2 μm to 50 μm are arranged in a matrix, and displays by individually driving each of a plurality of LEDs. Such a micro LED display can perform display without using liquid crystal.
マイクロＬＥＤディスプレイは、赤色発光、緑色発光、青色発光の３種類のＬＥＤ素子を用いる方式と、青色から近紫外の波長域の光を発する発光ＬＥＤチップ等の単色発光ＬＥＤ素子のみを用いる方式とに大別される。マイクロＬＥＤディスプレイにおいては、個々のＬＥＤ素子が表示機能層の役割を果たす。赤色発光、緑色発光、青色発光の３種類のＬＥＤ素子を用いる方式では、輝度や寿命に優れる長所を有する一方で、発光色の異なるＬＥＤ素子を実装するプロセスが多く、コストがかかるという欠点や、ＬＥＤ素子の発光特性ばらつきがあり、その制御が困難であるという欠点等、がある。 There are two types of micro LED displays: one uses three types of LED elements that emit red light, green light, and blue light, and the other uses only monochromatic light emitting LED elements such as light emitting LED chips that emit light in the wavelength range from blue to near ultraviolet. Broadly classified. In micro LED displays, individual LED elements play the role of a display functional layer. The method using three types of LED elements, emitting red light, green light, and blue light, has the advantage of excellent brightness and long life, but has the drawback that it requires many processes to mount LED elements with different light emission colors, which increases cost. There are drawbacks such as the fact that the light emitting characteristics of the LED elements vary and it is difficult to control them.
単色発光ＬＥＤ素子を用いる方式では、複数の単色発光ＬＥＤ素子の各々に、発光波長を赤色、緑色、及び青色のいずれかへ波長を変換する波長変換層（例えば、量子ドットや無機蛍光体等の分散体）を積層することで、カラー表示を実現している。
前記波長変換層用の感光性樹脂組成物として、少なくとも、ｈ線の吸光係数が１００ｍＬ／ｇ・ｃｍ以上である光重合開始剤、ピロメテン誘導体、光重合性化合物及びアルカリ可溶性樹脂を含有することを特徴とする感光性樹脂組成物が提案されている（特許文献１）。前記感光性樹脂組成物では、前記アルカリ可溶性樹脂としてアクリル樹脂が使用されている。
In a method using monochromatic LED elements, each of a plurality of monochromatic LED elements is provided with a wavelength conversion layer (for example, quantum dots, inorganic phosphors, etc.) that converts the emission wavelength to red, green, or blue. Color display is achieved by layering dispersions).
The photosensitive resin composition for the wavelength conversion layer contains at least a photopolymerization initiator having an extinction coefficient of 100 mL/g cm or more for h-line, a pyrromethene derivative, a photopolymerizable compound, and an alkali-soluble resin. A photosensitive resin composition with characteristics has been proposed (Patent Document 1). In the photosensitive resin composition, an acrylic resin is used as the alkali-soluble resin.
有機ＥＬディスプレイ、マイクロＬＥＤディスプレイの波長変換層を形成する場合、段階的に加熱硬化させる手法は公知である。しかしながら、従来品であるアクリル樹脂やウレタン樹脂を含有した感光性樹脂組成物を加熱硬化させると硬化膜の発光維持率が低下するという、耐熱性の問題が存在する。
また、短時間で現像した場合に、現像性の点で十分でない問題も存在する。
そこで、本発明の課題は、耐熱性に優れた蛍光体分散体を提供することにある。また本発明の他の課題は、耐熱性及び現像性に優れた蛍光体感光性組成物を提供することにある。
When forming a wavelength conversion layer for an organic EL display or a micro LED display, a method of heating and curing in stages is known. However, when a conventional photosensitive resin composition containing an acrylic resin or a urethane resin is cured by heating, there is a problem in heat resistance in that the luminescence retention rate of the cured film decreases.
Furthermore, there is a problem in that the developability is not sufficient when developing in a short time.
Therefore, an object of the present invention is to provide a phosphor dispersion with excellent heat resistance. Another object of the present invention is to provide a phosphor photosensitive composition with excellent heat resistance and developability.
本発明に係る第１の態様は、赤色系蛍光、緑色系蛍光又は青色系蛍光を放出する無機蛍光体と、変性シリコーン系分散剤と、シリコーン系樹脂と、光重合性化合物と、光重合開始剤と、有機溶剤とを含有することを特徴とする、蛍光体感光性組成物に関する。 A first aspect of the present invention includes an inorganic phosphor that emits red fluorescence, green fluorescence, or blue fluorescence, a modified silicone dispersant, a silicone resin, a photopolymerizable compound, and a photopolymerization initiator. The present invention relates to a phosphor photosensitive composition characterized by containing an organic solvent and an organic solvent.
前記蛍光体感光性組成物では、前記変性シリコーン系分散剤は、脂肪族変性シリコーンであってもよい。 In the phosphor photosensitive composition, the modified silicone-based dispersant may be an aliphatic modified silicone.
前記蛍光体感光性組成物は、前記無機蛍光体、前記変性シリコーン系分散剤及び前記有機溶剤を含有する蛍光体分散体と、前記シリコーン系樹脂、前記光重合性化合物、前記光重合開始剤及び前記有機溶剤との混合物であってもよい。 The phosphor photosensitive composition includes a phosphor dispersion containing the inorganic phosphor, the modified silicone dispersant, and the organic solvent, the silicone resin, the photopolymerizable compound, the photopolymerization initiator, and It may also be a mixture with the above organic solvent.
前記蛍光体感光性組成物は、前記無機蛍光体１０～３５重量％、変性シリコーン分散剤１～１６重量％、シリコーン系樹脂５～２０重量％、光重合性化合物１～１５重量％、光重合開始剤０．１～３重量％、及び有機溶剤１３～７４重量％を含有してもよい。 The phosphor photosensitive composition contains 10 to 35% by weight of the inorganic phosphor, 1 to 16% by weight of a modified silicone dispersant, 5 to 20% by weight of a silicone resin, 1 to 15% by weight of a photopolymerizable compound, and 1 to 15% by weight of a photopolymerizable compound. It may contain 0.1 to 3% by weight of an initiator and 13 to 74% by weight of an organic solvent.
前記蛍光体感光性組成物は、波長変換層用であってもよい。 The phosphor photosensitive composition may be used for a wavelength conversion layer.
本発明に係る第２の態様は、赤色系蛍光、緑色系蛍光又は青色系蛍光を放出する無機蛍光体と、変性シリコーン系分散剤と、有機溶剤とを含有することを特徴とする、蛍光体分散体に関する。 A second aspect of the present invention is a phosphor containing an inorganic phosphor that emits red fluorescence, green fluorescence, or blue fluorescence, a modified silicone dispersant, and an organic solvent. Regarding dispersions.
前記蛍光体分散体では、前記変性シリコーン系分散剤が脂肪族変性シリコーンであってもよい。 In the phosphor dispersion, the modified silicone-based dispersant may be an aliphatic modified silicone.
前記蛍光体分散体は、さらにシリコーン系樹脂を含有してもよい。 The phosphor dispersion may further contain a silicone resin.
本発明に係る蛍光体感光性組成物は、耐熱性に優れるために加熱硬化させた場合でも発光維持率が高く、現像性にも優れる。そのため、この蛍光体感光性組成物を用いて作製した波長変換層を有する表示装置用基板は、単位面積あたり従来より少ない蛍光体量でも、必要な発光輝度を保つことができる。
また、本発明に係る蛍光体感光性組成物は発光維持率が高いため、従来品に比べて表示装置用基板を効率よく低コストで製造することができる。
本発明に係る蛍光体感光性組成物は、現像性にも優れる。
前記蛍光体感光性組成物は、本発明に係る蛍光体分散体を用いることで効率よく製造することができる。
The phosphor photosensitive composition according to the present invention has excellent heat resistance, so even when it is heated and cured, it has a high luminescence retention rate and has excellent developability. Therefore, a display device substrate having a wavelength conversion layer produced using this phosphor photosensitive composition can maintain the required luminance even with a smaller amount of phosphor per unit area than conventional ones.
Further, since the phosphor photosensitive composition according to the present invention has a high luminescence maintenance rate, it is possible to manufacture a display device substrate more efficiently and at lower cost than conventional products.
The phosphor photosensitive composition according to the present invention also has excellent developability.
The phosphor photosensitive composition can be efficiently produced by using the phosphor dispersion according to the present invention.
以下、本発明に係る蛍光体感光性組成物及び蛍光体分散体の実施形態について説明する。 Embodiments of the phosphor photosensitive composition and phosphor dispersion according to the present invention will be described below.
（蛍光体感光性組成物）
本発明の実施形態に係る蛍光体感光性組成物（以下、本発明の組成物ともいう）は、赤色系蛍光、緑色系蛍光又は青色系蛍光を放出する無機蛍光体と、変性シリコーン系分散剤と、シリコーン系樹脂と、光重合性化合物と、光重合開始剤と、有機溶剤とを含有することを特徴とする。
(Phosphor photosensitive composition)
A phosphor photosensitive composition according to an embodiment of the present invention (hereinafter also referred to as a composition of the present invention) includes an inorganic phosphor that emits red fluorescence, green fluorescence, or blue fluorescence, and a modified silicone dispersant. It is characterized by containing a silicone resin, a photopolymerizable compound, a photopolymerization initiator, and an organic solvent.
本発明の組成物では、変性シリコーン系分散剤と、シリコーン系樹脂とを併用することで、組成物中における赤色系蛍光、緑色系蛍光又は青色系蛍光を放出する無機蛍光体の分散性が向上し、かつ耐熱性及び現像性が優れたものとなる。 In the composition of the present invention, the combined use of a modified silicone dispersant and a silicone resin improves the dispersibility of the inorganic phosphor that emits red fluorescence, green fluorescence, or blue fluorescence in the composition. Moreover, it has excellent heat resistance and developability.
［無機蛍光体］
前記無機蛍光体とは、無機化合物からなり、かつ紫外線を吸収して赤色光、緑色光又は青色光を放出する蛍光体であり、従来から種々のものが知られている。
本発明において、市販されている前記無機蛍光体であれば、その粒径等に関わらず、使用することができる。
本発明では、前記無機蛍光体を、１種単独で又は異なる２種以上の組み合わせで使用することができる。
[Inorganic phosphor]
The inorganic phosphor is a phosphor that is made of an inorganic compound and that absorbs ultraviolet light and emits red, green, or blue light, and various types have been known.
In the present invention, any commercially available inorganic phosphor can be used regardless of its particle size.
In the present invention, the inorganic phosphors can be used alone or in combination of two or more different types.
無機蛍光体は、有機溶剤に分散させた分散体として使用する。
無機蛍光体の分散粒子径は、前記無機蛍光体の作用効果を十分に発揮する観点から、０．５～３０μｍが好ましく、１～２０μｍがより好ましい。
本明細書において、無機蛍光体の分散粒子径は、蛍光体を樹脂組成物に分散させた後の平均粒子径のことを指し、光子相関法によって求めた粒度分布における積算値５０％での粒子径を意味する。
The inorganic phosphor is used as a dispersion in an organic solvent.
The dispersed particle diameter of the inorganic phosphor is preferably 0.5 to 30 μm, more preferably 1 to 20 μm, from the viewpoint of fully exhibiting the effects of the inorganic phosphor.
In this specification, the dispersed particle size of an inorganic phosphor refers to the average particle size after dispersing the phosphor in a resin composition, and refers to the average particle size of particles at 50% of the integrated value in the particle size distribution determined by the photon correlation method. means diameter.
本発明の組成物中における前記無機蛍光体の含有量としては、前記無機蛍光体の作用効果を十分に発揮する観点から、１０～３５重量％が好まく、１５～３０重量％がより好ましい。 The content of the inorganic phosphor in the composition of the present invention is preferably 10 to 35% by weight, more preferably 15 to 30% by weight, from the viewpoint of fully exhibiting the effects of the inorganic phosphor.
［変性シリコーン系分散剤］
前記無機蛍光体と共に必須成分として用いられる変性シリコーン系分散剤は、蛍光体層において無機蛍光体を保持するマトリックス樹脂になる。さらに、前記無機蛍光体を高温から保護し、高温に晒されても、前記無機蛍光体の熱による変質や劣化を抑制する。
[Modified silicone dispersant]
The modified silicone dispersant used as an essential component together with the inorganic phosphor becomes a matrix resin that holds the inorganic phosphor in the phosphor layer. Furthermore, the inorganic phosphor is protected from high temperatures, and even when exposed to high temperatures, alteration and deterioration of the inorganic phosphor due to heat is suppressed.
変性シリコーン系分散剤は、ケイ素と酸素が化学結合により交互に連なったシロキサン結合を主骨格に持つシリコーンの一部に置換基が導入された構造をもつ変性シリコーン系化合物を主成分とするものである。
前記変性シリコーン系分散剤としては、脂肪族変性シリコーン及び芳香族変性シリコーンが挙げられる。
Modified silicone-based dispersants are mainly composed of modified silicone-based compounds that have a structure in which a substituent has been introduced into a part of silicone, which has a siloxane bond in its main skeleton in which silicon and oxygen are linked alternately through chemical bonds. be.
Examples of the modified silicone-based dispersant include aliphatic modified silicones and aromatic modified silicones.
前記脂肪族変性シリコーンとしては、ポリエステル、ポリエーテル等の側鎖を有する脂肪族ポリエステル変性シリコーンが挙げられる。
前記脂肪族ポリエステル変性シリコーンにおける側鎖を構成する炭素数としては、特に限定はないが、本発明の効果が奏されやすい観点から、１～１０であることが好ましい。
また、前記脂肪族変性シリコーンの主鎖は、直鎖型、分岐型、環状型のいずれでもよい。
前記脂肪族変性シリコーンとしては、市販品を使用することができ、例えば、
ＫＲ－５２３０、ＫＲ－５２３４、ＫＲ－５２３５（いずれも商品名、信越化学工業（株）製）、ＢＹＫ（登録商標）－３１３、ＢＹＫ－３０２（いずれも商品名、ＢＹＫ－Ｃｈｅｍｉｅ社製）、ＴＳＲ１８０、（いずれも商品名、モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社製）
等が挙げられる。
Examples of the aliphatic modified silicone include aliphatic polyester modified silicones having side chains such as polyester and polyether.
The number of carbon atoms constituting the side chain in the aliphatic polyester-modified silicone is not particularly limited, but is preferably from 1 to 10 from the viewpoint of easily achieving the effects of the present invention.
Further, the main chain of the aliphatic modified silicone may be linear, branched, or cyclic.
As the aliphatic modified silicone, commercially available products can be used, for example,
KR-5230, KR-5234, KR-5235 (all product names, manufactured by Shin-Etsu Chemical Co., Ltd.), BYK (registered trademark)-313, BYK-302 (all product names, manufactured by BYK-Chemie), TSR180, (both product names, manufactured by Momentive Performance Materials Japan LLC)
etc.
前記芳香族変性シリコーンとしては、芳香族ポリエステル変性シリコーン、半芳香族ポリエステル変性シリコーン等が挙げられる。 Examples of the aromatic modified silicone include aromatic polyester modified silicone, semi-aromatic polyester modified silicone, and the like.
前記芳香族変性シリコーンとしては、市販品を使用することができ、例えば、ＢＹＫ-３２２、ＢＹＫ-３２３（いずれも商品名、ＢＹＫ－Ｃｈｅｍｉｅ社製）
ＫＲ－１１２、ＫＲ－２１１、ＫＲ－２１２、ＫＲ－２５５、ＫＲ－２７１、ＫＲ－２８２、ＫＲ－３００、ＫＲ－３１１、ＫＲ－２６２１－１、Ｘ－４０－２６６７Ａ、ＫＲ－４８０（いずれも商品名、信越化学工業（株）製）、
ＳＩＬＩＫＯＦＴＡＬ（登録商標） ＨＴＴ（商品名、エボニック社製）、ＴＳＲｌ１６、ＴＳＲｌ１７、ＴＳＲ１４４、ＹＲ４７（いずれも商品名、モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社製）
等を用いてもよい。
As the aromatic modified silicone, commercially available products can be used, such as BYK-322 and BYK-323 (both trade names, manufactured by BYK-Chemie).
KR-112, KR-211, KR-212, KR-255, KR-271, KR-282, KR-300, KR-311, KR-2621-1, X-40-2667A, KR-480 (all Product name (manufactured by Shin-Etsu Chemical Co., Ltd.),
SILIKOFTAL (registered trademark) HTT (product name, manufactured by Evonik), TSRl16, TSRl17, TSR144, YR47 (all product names, manufactured by Momentive Performance Materials Japan LLC)
etc. may also be used.
本発明では、本発明の効果が奏されやすい観点から、前記脂肪族変性シリコーンが好ましい。 In the present invention, the aliphatic modified silicone is preferable from the viewpoint of easily achieving the effects of the present invention.
前記変性シリコーン系分散剤として使用される前記樹脂の分子量は、無機蛍光体の種類や含有量、本発明の組成物の用途等に応じて広い範囲から適宜選択できる。 The molecular weight of the resin used as the modified silicone dispersant can be appropriately selected from a wide range depending on the type and content of the inorganic phosphor, the use of the composition of the present invention, and the like.
本発明の組成物においては、前記変性シリコーン系分散剤が存在することにより前記無機蛍光体の熱による劣化や変質が顕著に抑制される。前記変性シリコーン系分散剤の配合量は特に制限されず、使用する前記無機蛍光体の種類や粒径、前記変性シリコーン系分散剤の種類、本発明の組成物の用途等に応じ、その保存安定性、塗工性、ハンドリング性や、硬化後の蛍光体層の機械強度や耐久性、等を考慮して、適した範囲を適宜選択すればよい。 In the composition of the present invention, the presence of the modified silicone dispersant significantly suppresses deterioration and deterioration of the inorganic phosphor due to heat. The amount of the modified silicone dispersant is not particularly limited, and depends on the type and particle size of the inorganic phosphor used, the type of the modified silicone dispersant, the use of the composition of the present invention, etc. An appropriate range may be selected as appropriate, taking into consideration properties, coating properties, handling properties, mechanical strength and durability of the phosphor layer after curing, and the like.
本発明の組成物中における前記変性シリコーン系分散剤の含有量としては、前記無機蛍光体の熱による劣化又は変質を抑制又は防止する観点から、１～１６重量％が好ましく、１～１０重量％がより好ましい。 The content of the modified silicone dispersant in the composition of the present invention is preferably 1 to 16% by weight, and 1 to 10% by weight from the viewpoint of suppressing or preventing heat-induced deterioration or alteration of the inorganic phosphor. is more preferable.
なお、前記変性シリコーン系分散剤ではなく、アクリル樹脂等の他の樹脂系分散剤を用いた場合には、耐熱性及び現像性が共に優れた蛍光体感光性組成物とはならない。 Note that, if another resin-based dispersant such as an acrylic resin is used instead of the modified silicone-based dispersant, a phosphor photosensitive composition having excellent heat resistance and developability cannot be obtained.
［シリコーン系樹脂］
本発明における「シリコーン系樹脂」は、前記無機蛍光体の分散媒として作用する成分である。なお、シリコーン系樹脂には、前記変性シリコーン系分散剤として使用される樹脂は含まれない。
[Silicone resin]
The "silicone resin" in the present invention is a component that acts as a dispersion medium for the inorganic phosphor. Note that the silicone resin does not include the resin used as the modified silicone dispersant.
前記シリコーン系樹脂は、シロキサン結合（Ｓｉ－Ｏ－Ｓｉ結合）を主鎖とする樹脂である。
本実施形態のシリコーン系樹脂は、下記式（ｉａ）で表される繰り返し単位を含有する。
The silicone resin is a resin having a siloxane bond (Si--O--Si bond) as its main chain.
The silicone resin of this embodiment contains a repeating unit represented by the following formula (ia).
式（ｉａ）中、Ｒは、水素原子又は炭素数１～３０かつ１価～３価の炭化水素基である。炭化水素基は、脂肪族でも芳香族でもよく、飽和でも不飽和でもよく、直鎖状でも分岐状でも環状でもよい。炭化水素基の炭素数が２以上の場合、炭化水素基における１つ以上のメチレン基は非置換であってもよく、酸素、イミド基又はカルボニル基で置換されていてもよい。炭化水素基の炭素数が２以上の場合、炭化水素基における１つ以上の水素は非置換であってもよく、フッ素、水酸基又は炭素数１～２０のアルコキシ基で置換されていてもよい。炭化水素基の炭素数が２以上の場合、炭化水素基における１つ以上の炭素は非置換であってもよく、ケイ素で置換されていてもよい。炭化水素基が２価又は３価の場合、炭化水素基は、複数の繰り返し単位に含まれるＳｉ同士を連結していてもよい。 In formula (ia), R is a hydrogen atom or a monovalent to trivalent hydrocarbon group having 1 to 30 carbon atoms. The hydrocarbon group may be aliphatic or aromatic, saturated or unsaturated, and linear, branched, or cyclic. When the hydrocarbon group has two or more carbon atoms, one or more methylene groups in the hydrocarbon group may be unsubstituted or substituted with oxygen, an imide group, or a carbonyl group. When the hydrocarbon group has 2 or more carbon atoms, one or more hydrogen atoms in the hydrocarbon group may be unsubstituted or substituted with fluorine, a hydroxyl group, or an alkoxy group having 1 to 20 carbon atoms. When the hydrocarbon group has two or more carbon atoms, one or more carbons in the hydrocarbon group may be unsubstituted or substituted with silicon. When the hydrocarbon group is divalent or trivalent, the hydrocarbon group may connect Si contained in a plurality of repeating units.
式（ｉａ）中、Ｒは、アルキル基が好ましい。
Ｒが炭化水素基の場合、炭化水素基の炭素数は、１～１０が好ましく、１～６がより好ましい。炭化水素基の価数は、２価又は３価が好ましく、３価がより好ましい。炭化水素基は、脂肪族が好ましい。炭化水素基は、飽和が好ましい。炭化水素基は、分岐状が好ましい。
In formula (ia), R is preferably an alkyl group.
When R is a hydrocarbon group, the number of carbon atoms in the hydrocarbon group is preferably 1 to 10, more preferably 1 to 6. The valence of the hydrocarbon group is preferably divalent or trivalent, more preferably trivalent. The hydrocarbon group is preferably aliphatic. The hydrocarbon group is preferably saturated. The hydrocarbon group is preferably branched.
炭化水素基における水素がアルコキシ基で置換されている場合、アルコキシ基の炭素数は、１～２０が好ましく、１～６がより好ましい。 When hydrogen in the hydrocarbon group is substituted with an alkoxy group, the number of carbon atoms in the alkoxy group is preferably 1 to 20, more preferably 1 to 6.
式（ｉａ）で表される繰り返し単位は、シルセスキオキサン構造単位である。
シルセスキオキサンは、３官能性シランを加水分解することで得られる（ＲＳｉＯ１．５）ｎ（ｎは自然数）の構造を有するネットワーク型ポリマー又は多面体クラスターである。各ケイ素原子は、平均１．５個の酸素原子と、１つの炭化水素基と結合している。最大８個の有機官能基と、Ｓｉ－Ｏ結合とでできたカゴ状骨格を有する無機化合物である。シルセスキオキサンは、シリカ（ＳｉＯ２）とシリコーン（Ｒ２ＳｉＯ）の中間の量論的化合物であり、有機物に親和性を有する無機物である。
シリコーン系樹脂は、シルセスキオキサン構造単位を有することで、耐熱性及び耐黄変性により優れる。
The repeating unit represented by formula (ia) is a silsesquioxane structural unit.
Silsesquioxane is a network polymer or polyhedral cluster having a structure of (RSiO1.5)n (n is a natural number) obtained by hydrolyzing trifunctional silane. Each silicon atom is bonded to an average of 1.5 oxygen atoms and one hydrocarbon group. It is an inorganic compound that has a cage-like skeleton made up of up to eight organic functional groups and Si--O bonds. Silsesquioxane is a stoichiometric compound between silica (SiO2) and silicone (R2SiO), and is an inorganic substance that has an affinity for organic substances.
Silicone resin has excellent heat resistance and yellowing resistance because it has a silsesquioxane structural unit.
シルセスキオキサン構造単位の含有量は、シリコーン系樹脂を構成する繰り返し単位の総数に対して、４０～８０モル％であり、４５～７５モル％が好ましく、５０～７０モル％がより好ましい。シルセスキオキサン構造単位の含有量が上記下限値以上であると、蛍光体感光性組成物の耐熱性及び耐黄変性をより高められる。シルセスキオキサン構造単位の含有量が上記上限値以下であると、蛍光体感光性組成物の透明性をより高められる。 The content of the silsesquioxane structural unit is 40 to 80 mol%, preferably 45 to 75 mol%, and more preferably 50 to 70 mol%, based on the total number of repeating units constituting the silicone resin. When the content of the silsesquioxane structural unit is at least the above lower limit, the heat resistance and yellowing resistance of the phosphor photosensitive composition can be further improved. When the content of the silsesquioxane structural unit is below the above upper limit, the transparency of the phosphor photosensitive composition can be further improved.
シリコーン系樹脂は、下記式（ｉｂ）で表される繰り返し単位を含有してもよい。 The silicone resin may contain a repeating unit represented by the following formula (ib).
式（ｉｂ）で表される繰り返し単位の含有量は、シリコーン系樹脂を構成する繰り返し単位の総数に対して、４０モル％以下が好ましく、１０～２０モル％がより好ましい。式（ｉｂ）で表される繰り返し単位の含有量が上記下限値以上であると、蛍光体感光性組成物の耐熱性及び耐黄変性をより高められる。式（ｉｂ）で表される繰り返し単位の含有量が上記上限値以下であると、蛍光体感光性組成物の透明性をより高められる。
式（ｉｂ）で表される繰り返し単位の含有量は、例えば、ガスクロマトグラフィー（ＧＣ）により求めることができる。
The content of the repeating unit represented by formula (ib) is preferably 40 mol% or less, more preferably 10 to 20 mol%, based on the total number of repeating units constituting the silicone resin. When the content of the repeating unit represented by formula (ib) is at least the above lower limit, the heat resistance and yellowing resistance of the phosphor photosensitive composition can be further improved. When the content of the repeating unit represented by formula (ib) is below the above upper limit, the transparency of the phosphor photosensitive composition can be further improved.
The content of the repeating unit represented by formula (ib) can be determined, for example, by gas chromatography (GC).
シリコーン系樹脂は、式（ｉａ）で表される繰り返し単位及び式（ｉｂ）で表される繰り返し単位以外の繰り返し単位（以下、「他の繰り返し単位」ともいう。）を含有してもよい。他の繰り返し単位としては、例えば、ビニル化合物に由来する繰り返し単位、アクリル化合物に由来する繰り返し単位、ポリエステル化合物に由来する繰り返し単位等が挙げられる。他の繰り返し単位の含有量は、シリコーン系樹脂を構成する繰り返し単位の総数に対して、１モル％以下が好ましく、０モル％がより好ましい。他の繰り返し単位の含有量が上記上限値以下であると、蛍光体感光性組成物の有機物含有率を低減でき、蛍光体感光性組成物の耐熱性及び耐黄変性をより高められる。
他の繰り返し単位の含有量は、例えば、ガスクロマトグラフィーにより求めることができる。
The silicone resin may contain repeating units other than the repeating unit represented by formula (ia) and the repeating unit represented by formula (ib) (hereinafter also referred to as "other repeating units"). Examples of other repeating units include repeating units derived from vinyl compounds, repeating units derived from acrylic compounds, repeating units derived from polyester compounds, and the like. The content of other repeating units is preferably 1 mol% or less, more preferably 0 mol%, based on the total number of repeating units constituting the silicone resin. When the content of other repeating units is below the above upper limit, the organic matter content of the phosphor photosensitive composition can be reduced, and the heat resistance and yellowing resistance of the phosphor photosensitive composition can be further improved.
The content of other repeating units can be determined, for example, by gas chromatography.
シリコーン系樹脂の質量平均分子量は、５００～２５，０００が好ましく、１，０００～２０，０００がより好ましい。シリコーン系樹脂の質量平均分子量が上記下限値以上であると、蛍光体感光性組成物の耐熱性及び耐黄変性をより高められる。シリコーン系樹脂の質量平均分子量が上記上限値以下であると、蛍光体感光性組成物の透明性をより高められる。
本明細書において、質量平均分子量は、ポリスチレン換算の質量平均分子量を意味し、ポリスチレンを基準物質として、ゲル浸透クロマトグラフィー（ＧＰＣ）により求められる。
The weight average molecular weight of the silicone resin is preferably 500 to 25,000, more preferably 1,000 to 20,000. When the mass average molecular weight of the silicone resin is at least the above lower limit, the heat resistance and yellowing resistance of the phosphor photosensitive composition can be further improved. When the mass average molecular weight of the silicone resin is at most the above upper limit, the transparency of the phosphor photosensitive composition can be further improved.
In this specification, the mass average molecular weight means the mass average molecular weight in terms of polystyrene, and is determined by gel permeation chromatography (GPC) using polystyrene as a reference material.
本発明の組成物中における前記シリコーン系樹脂の含有量としては、フォトレジストの現像性の観点から、５～２０重量％が好ましい。 The content of the silicone resin in the composition of the present invention is preferably 5 to 20% by weight from the viewpoint of photoresist developability.
［光重合性化合物］
本発明における「光重合性化合物」とは、エチレン性不飽和基を有する化合物をいう。光重合性化合物としては、例えば、ビスフェノールＡジ（メタ）アクリレート、変性ビスフェノールＡジ（メタ）アクリレート、ジプロピレングリコールジ（メタ）アクリレート、変性ネオペンチルグリコールジ（メタ）アクリレート、ＰＥＧ４００ジ（メタ）アクリレート、ＰＥＧ６００ジ（メタ）アクリレート、ビスフェノールＡジグリシジルエーテル（メタ）アクリレート、変性ビスフェノールＡエポキシ（メタ）アクリレート、ポリ（メタ）アクリレートカルバメート、アジピン酸１，６－ヘキサンジオール（メタ）アクリル酸エステル、無水フタル酸プロピレンオキサイド（メタ）アクリル酸エステル、トリメリット酸ジエチレングリコール（メタ）アクリル酸エステル、ロジン変性エポキシジ（メタ）アクリレート、アルキッド変性（メタ）アクリレートなどのオリゴマー、トリプロピレングリコールジ（メタ）アクリレート、１，６－ヘキサンジオールジ（メタ）アクリレート、ビスフェノールＡジグリシジルエーテルジ（メタ）アクリレート、トリシクロデカンジメタノールジ（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、トリメチロールプロパンエトキシトリ（メタ）アクリレート、グリセリンプロポキシトリ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、トリアクリルホルマール、トリス［２－（アクリロイルオキシ）エチル］イソシアヌラート、ジトリメチロールプロパンテトラ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート、ジペンタエリスリトールペンタ（メタ）アクリレート、ジペンタエリスリトールポリアクリレート、ビスフェノキシエタノールフルオレンジアクリレート、ジシクロペンタンジエニルジアクリレート、イソボルニル（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、これらのアルキル変性物、アルキルエーテル変性物やアルキルエステル変性物などが挙げられる。本発明の組成物では、光重合性化合物として、これらを２種以上含有してもよい。
[Photopolymerizable compound]
The "photopolymerizable compound" in the present invention refers to a compound having an ethylenically unsaturated group. Examples of photopolymerizable compounds include bisphenol A di(meth)acrylate, modified bisphenol A di(meth)acrylate, dipropylene glycol di(meth)acrylate, modified neopentyl glycol di(meth)acrylate, and PEG400 di(meth)acrylate. Acrylate, PEG600 di(meth)acrylate, bisphenol A diglycidyl ether (meth)acrylate, modified bisphenol A epoxy (meth)acrylate, poly (meth)acrylate carbamate, adipic acid 1,6-hexanediol (meth)acrylate ester , phthalic anhydride propylene oxide (meth)acrylate, trimellitic acid diethylene glycol (meth)acrylate, rosin-modified epoxy di(meth)acrylate, alkyd-modified (meth)acrylate, and other oligomers, tripropylene glycol di(meth)acrylate , 1,6-hexanediol di(meth)acrylate, bisphenol A diglycidyl ether di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolpropane ethoxytri( meth)acrylate, glycerin propoxytri(meth)acrylate, pentaerythritol tri(meth)acrylate, triacryl formal, tris[2-(acryloyloxy)ethyl]isocyanurate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tetra (meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol polyacrylate, bisphenoxyethanol fluorene diacrylate, dicyclopentanedienyl diacrylate, isobornyl (meth)acrylate, polyethylene Examples include glycol di(meth)acrylate, alkyl-modified products, alkyl ether-modified products, and alkyl ester-modified products thereof. The composition of the present invention may contain two or more of these as photopolymerizable compounds.
本発明の組成物中における光重合性化合物の含有量としては、硬化させた塗膜の強度の観点から、１～１５重量％が好ましい。 The content of the photopolymerizable compound in the composition of the present invention is preferably 1 to 15% by weight from the viewpoint of the strength of the cured coating film.
［光重合開始剤］
本発明における「光重合開始剤」とは、光（紫外線、電子線を含む）により分解及び／又は反応し、前記光重合性化合物の重合を開始するための化合物であればよい。例えば、２－メチル－［４－（メチルチオ）フェニル］－２－モルフォリノプロパン－１－オン、２－ジメチルアミノ－２－（４－メチルベンジル）－１－（４－モルフォリン－４－イル－フェニル）－ブタン－１－オン、２－ベンジル－２－ジメチルアミノ－１－（４－モルフォリノフェニル）－ブタノン－１などのα－アミノアルキルフェノン化合物；２，４，６－トリメチルベンゾイルフェニルホスフィンオキサイド、ビス（２，４，６－トリメチルベンゾイル)－フェニルホスフィンオキサイド、ビス（２，６－ジメトキシベンゾイル）－（２，４，４－トリメチルペンチル）－ホスフィンオキサイドなどのアシルホスフィンオキサイド化合物；１－フェニル－１，２－プロパンジオン－２－（Ｏ－エトキシカルボニル）オキシム、１，２－オクタンジオン,１－［４－（フェニルチオ）－２－（Ｏ－ベンゾイルオキシム）］、１，２－オクタンジオン,１－［４－（フェニルチオ）フェニル］－,２－（Ｏ－ベンゾイルオキシム）、１－フェニル－１，２－ブタジオン－２－（Ｏ－メトキシカルボニル）オキシム、１，３－ジフェニルプロパントリオン－２－（Ｏ－エトキシカルボニル）オキシム、エタノン，１－［９－エチル－６－（２－メチルベンゾイル）－９Ｈ－カルバゾール－３－イル］－，１－（Ｏ－アセチルオキシム）などのオキシムエステル化合物；ベンジルジメチルケタールなどのベンジルケタール化合物；２－ヒドロキシ－２－メチル－１－フェニルプロパン－１－オン、１－（４－イソプロピルフェニル）－２－ヒドロキシ－２－メチルプロパン－１－オン、４－（２－ヒドロキシエトキシ）フェニル－（２－ヒドロキシ－２－プロピル）ケトン、１－ヒドロキシシクロヘキシル－フェニルケトンなどのα－ヒドロキシケトン化合物；ベンゾフェノン、４，４－ビス（ジメチルアミノ）ベンゾフェノン、４，４－ビス（ジエチルアミノ）ベンゾフェノン、Ｏ－ベンゾイル安息香酸メチル、４－フェニルベンゾフェノン、４，４－ジクロロベンゾフェノン、ヒドロキシベンゾフェノン、４－ベンゾイル－４’－メチル－ジフェニルサルファイド、アルキル化ベンゾフェノン、３，３’，４，４’－テトラ（ｔ－ブチルパーオキシカルボニル）ベンゾフェノンなどのベンゾフェノン化合物；２，２－ジエトキシアセトフェノン、２，３－ジエトキシアセトフェノン、４－ｔ－ブチルジクロロアセトフェノン、ベンザルアセトフェノン、４－アジドベンザルアセトフェノンなどのアセトフェノン化合物；２－フェニル－２－オキシ酢酸メチルなどの芳香族ケトエステル化合物；４－ジメチルアミノ安息香酸エチル、４－ジメチルアミノ安息香酸（２－エチル）ヘキシル、４－ジエチルアミノ安息香酸エチル、２－ベンゾイル安息香酸メチルなどの安息香酸エステル化合物などが挙げられる。これらを２種以上含有してもよい。
[Photopolymerization initiator]
The "photopolymerization initiator" in the present invention may be any compound that decomposes and/or reacts with light (including ultraviolet rays and electron beams) and initiates polymerization of the photopolymerizable compound. For example, 2-methyl-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl α-aminoalkylphenone compounds such as -phenyl)-butan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1; 2,4,6-trimethylbenzoylphenyl Acyl phosphine oxide compounds such as phosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)-phosphine oxide; 1 -Phenyl-1,2-propanedione-2-(O-ethoxycarbonyl)oxime, 1,2-octanedione,1-[4-(phenylthio)-2-(O-benzoyloxime)], 1,2- Octanedione, 1-[4-(phenylthio)phenyl]-,2-(O-benzoyloxime), 1-phenyl-1,2-butadione-2-(O-methoxycarbonyl)oxime, 1,3-diphenylpropane Trion-2-(O-ethoxycarbonyl)oxime, ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,1-(O-acetyloxime), etc. Oxime ester compounds; benzyl ketal compounds such as benzyl dimethyl ketal; 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1- α-hydroxyketone compounds such as 1, 4-(2-hydroxyethoxy)phenyl-(2-hydroxy-2-propyl)ketone, and 1-hydroxycyclohexyl-phenylketone; benzophenone, 4,4-bis(dimethylamino)benzophenone , 4,4-bis(diethylamino)benzophenone, methyl O-benzoylbenzoate, 4-phenylbenzophenone, 4,4-dichlorobenzophenone, hydroxybenzophenone, 4-benzoyl-4'-methyl-diphenyl sulfide, alkylated benzophenone, 3 , 3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone; 2,2-diethoxyacetophenone, 2,3-diethoxyacetophenone, 4-t-butyldichloroacetophenone, benzal Acetophenone compounds such as acetophenone and 4-azidobenzalacetophenone; aromatic ketoester compounds such as methyl 2-phenyl-2-oxyacetate; ethyl 4-dimethylaminobenzoate, (2-ethyl)hexyl 4-dimethylaminobenzoate, Examples include benzoic acid ester compounds such as ethyl 4-diethylaminobenzoate and methyl 2-benzoylbenzoate. Two or more types of these may be contained.
本発明の組成物中における光重合開始剤の含有量としては、重合速度と塗膜の物性との観点から、０．１～３重量％が好ましい。 The content of the photopolymerization initiator in the composition of the present invention is preferably 0.1 to 3% by weight from the viewpoint of polymerization rate and physical properties of the coating film.
［有機溶剤］
本発明の組成物で使用する有機溶剤は、前記無機蛍光体及び前記変性シリコーン系分散剤の分散性や保存安定性（特に前記無機蛍光体の凝集や沈殿の防止）、蛍光体層における前記無機蛍光体の均一分散性、本発明の組成物のハンドリング性、塗工性等を向上させるのに有用である。
[Organic solvent]
The organic solvent used in the composition of the present invention is used to improve the dispersibility and storage stability of the inorganic phosphor and the modified silicone dispersant (especially prevention of aggregation and precipitation of the inorganic phosphor), It is useful for improving the uniform dispersibility of the phosphor and the handling and coating properties of the composition of the present invention.
有機溶剤としては、前記無機蛍光体や前記変性シリコーン系分散剤の種類、これらの配合量、得られる本発明の組成物の用途等、種々の条件に応じて適宜選択される。例えば、芳香族系溶剤、脂肪族系溶剤、ケトン系溶剤、エステル系溶剤、グリコールエーテル系溶剤、アルコール系溶剤等が挙げられる。これらの中でも、シリコーン系樹脂との相溶性等を観点からは、芳香族系溶剤、ケトン系溶剤、エステル系溶剤、グリコールエーテル系剤等が好ましい。有機溶剤は、１種を単独で又は可能であれば２種以上組み合わせて用いてもよい。 The organic solvent is appropriately selected depending on various conditions such as the type of the inorganic phosphor and the modified silicone dispersant, their blending amount, and the intended use of the resulting composition of the present invention. Examples include aromatic solvents, aliphatic solvents, ketone solvents, ester solvents, glycol ether solvents, alcohol solvents, and the like. Among these, aromatic solvents, ketone solvents, ester solvents, glycol ether agents, and the like are preferred from the viewpoint of compatibility with silicone resins. The organic solvents may be used alone or in combination of two or more if possible.
芳香族系溶剤としては、トルエン、キシレン、エチルベンゼン等の芳香族炭化水素類が挙げられる。
脂肪族系溶剤としては、ｎ－ペンタン、ｎ－ヘキサン、ｎ－ヘプタン等の脂肪族炭化水素等が挙げられる。
ケトン系溶剤としては、メチルエチルケトン、メチルインブチルケトン、ジインブチルケトン、アセトン、アセチルアセトン、イソホロン、アセトフェノン、シクロヘキサノン等が挙げられる。
Examples of aromatic solvents include aromatic hydrocarbons such as toluene, xylene, and ethylbenzene.
Examples of aliphatic solvents include aliphatic hydrocarbons such as n-pentane, n-hexane, and n-heptane.
Examples of the ketone solvent include methyl ethyl ketone, methyl imbutyl ketone, diim butyl ketone, acetone, acetylacetone, isophorone, acetophenone, and cyclohexanone.
エステル系溶剤としては、例えば、酢酸エチル、酢酸－ｎ－ブチル、酢酸イソブチル、酢酸インプロピル、プロピオン酸メチル、酢酸－３－メトキシブチル、エチルグリコールアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、３－メチル－３－メトキシブチルアセテート、モノクロロ酢酸メチル、モノクロロ酢酸エチル、モノクロロ酢酸ブチル、アセト酢酸メチル、アセト酢酸エチル、ブチルカルビトールアセテート、乳酸ブチル、エチル－３－エトキシプロピオネート、エチレングリコールモノブチルエーテルアセテート、エチレングリコールモノメチルエーテルアセテート、酢酸プロピル、１，３－ブチレングリコールジアセテート等が挙げられる。 Examples of ester solvents include ethyl acetate, n-butyl acetate, isobutyl acetate, impropyl acetate, methyl propionate, 3-methoxybutyl acetate, ethyl glycol acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether Acetate, 3-methyl-3-methoxybutyl acetate, methyl monochloroacetate, ethyl monochloroacetate, butyl monochloroacetate, methyl acetoacetate, ethyl acetoacetate, butyl carbitol acetate, butyl lactate, ethyl-3-ethoxypropionate, ethylene Examples include glycol monobutyl ether acetate, ethylene glycol monomethyl ether acetate, propyl acetate, and 1,3-butylene glycol diacetate.
グリコールエーテル系溶剤としては、例えば、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノ－ｎ－プロピルエーテル、エチレングリコールモノ－ｉｓｏ－プロピルエーテル、ジエチレングリコールモノ－ｉｓｏ－プロピルエーテル、エチレングリコールモノ－ｎ－ブチルエーテル、ジエチレングリコールモノ－ｎ－ブチルエーテル、トリエチレングリコールモノ－ｎ－ブチルエーテル、エチレングリコールモノ－ｔｅｒｔ－ブチルエーテル、ジエチレングリコールモノ－ｔｅｒｔ－ブチルエーテル、１－メチル－１－メトキシブタノール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノ－ｔｅｒｔ－ブチルエーテル、プロピレングリコールモノ－ｎ－プロピルエーテル、プロピレングリコールモノ－ｉｓｏ－プロピルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノ－ｎ－プロピルエーテル、ジプロピレングリコールモノ－ｉｓｏ－プロピルエーテル、プロピレングリコールモノ－ｎ－ブチルエーテル、ジプロピレングリコールモノ－ｎ－ブチルエーテル等の水溶性のグリコールエーテル類、エチレングリコールモノヘキシルエーテル、エチレングリコール－２－エチルヘキシルエーテル、エチレングリコールフェニルエーテル、ジエチレングリコール－ｎ－ヘキシルエーテル、ジエチレングリコール－２－エチルヘキシルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノブチルエーテル、ジプロピレングリコールプロピルエーテル、プロピレングリコールメチルエーテルプロピオネート等の非水溶性のグリコールエーテル類等が挙げられる。 Examples of glycol ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, and ethylene glycol mono-iso-propyl ether. , diethylene glycol mono-iso-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol mono-n-butyl ether, ethylene glycol mono-tert-butyl ether, diethylene glycol mono-tert-butyl ether, 1- Methyl-1-methoxybutanol, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-tert-butyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-iso-propyl ether, dipropylene glycol monomethyl ether, Water-soluble glycol ethers such as dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-iso-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol mono-n-butyl ether, etc. , ethylene glycol monohexyl ether, ethylene glycol-2-ethylhexyl ether, ethylene glycol phenyl ether, diethylene glycol-n-hexyl ether, diethylene glycol-2-ethylhexyl ether, propylene glycol monobutyl ether, dipropylene glycol monobutyl ether, dipropylene glycol propyl Examples include ether and water-insoluble glycol ethers such as propylene glycol methyl ether propionate.
アルコール系溶剤としては、例えば、エタノール、メタノール、ｎ－ブタノール、ｎ－プロパノール、インプロパノール等の炭素数１～４のアルキルアルコール類、エチレングリコール、プロピレングリコール、ジエチレングリコール、ペンタメチレングリコール、 トリメチレングリコール、２－ブテンー１，４－ジオール、２－エチル－１，３－ヘキサンジオール、２－メチル－２，４－ペンタンジオール、トリプロピレングリコール、分子量２０００以下のポリエチレングリコール、１，３－プロピレングリコール、インプロピレングリコール、インブチレングリコール、１，４－ブタンジオール、１，３－ブタンジオール、１，５－ペンタンジオール、１，６－ヘキサンジオール、グリセリン、メノエリスリトール、ペンタエリスリトール等が挙げられる。 Examples of alcoholic solvents include alkyl alcohols having 1 to 4 carbon atoms such as ethanol, methanol, n-butanol, n-propanol, and impropanol, ethylene glycol, propylene glycol, diethylene glycol, pentamethylene glycol, trimethylene glycol, 2-butene-1,4-diol, 2-ethyl-1,3-hexanediol, 2-methyl-2,4-pentanediol, tripropylene glycol, polyethylene glycol with a molecular weight of 2000 or less, 1,3-propylene glycol, in Examples include propylene glycol, imbutylene glycol, 1,4-butanediol, 1,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, glycerin, menoerythritol, and pentaerythritol.
本発明の組成物中における有機溶剤の含有量としては、塗膜作製時のハンドリングを考慮して、１３～７４重量％が好ましく、５０～６５重量％がより好ましい。 The content of the organic solvent in the composition of the present invention is preferably 13 to 74% by weight, more preferably 50 to 65% by weight, taking into account handling during coating film production.
本発明の組成物は、前述成分の他に、必要に応じて、感光性組成物に用いられる任意の添加剤を含むことができる。該添加剤としては、例えば、増粘剤、分散助剤、ｐＨ調整剤、酸化防止剤、防腐剤、防カビ剤、界面活性剤、密着促進剤、表面調整剤、等が挙げられる。
前記増粘剤として、シリカ粒子ＡＣＥＭＡＴＴ（登録商標） ３６００（エボニック社製）、ＮＩＰＳＩＬ（登録商標） ＳＳ－５０Ｆ（東ソー・シリカ社製）等が挙げられる。
本発明の組成物における添加剤の含有量は、本発明の組成物中の０．０１～１０重量％の範囲から適宜選択される。
In addition to the above-mentioned components, the composition of the present invention can optionally contain any additives used in photosensitive compositions. Examples of the additives include thickeners, dispersion aids, pH adjusters, antioxidants, preservatives, antifungal agents, surfactants, adhesion promoters, surface conditioners, and the like.
Examples of the thickener include silica particles ACEMATT (registered trademark) 3600 (manufactured by Evonik), NIPSIL (registered trademark) SS-50F (manufactured by Tosoh Silica), and the like.
The content of the additive in the composition of the present invention is appropriately selected from the range of 0.01 to 10% by weight of the composition of the present invention.
本発明の組成物は、各成分を任意の順番で混合することにより製造してもよい。
中でも、効率よく本発明の組成物を製造できる観点から、前記無機蛍光体、前記変性シリコーン系分散剤及び前記有機溶剤を含有する蛍光体分散体を予め作製し、この蛍光体分散体、前記シリコーン系樹脂、前記光重合性化合物、前記光重合開始剤及び前記有機溶剤を混合することで本発明の組成物を製造することが好ましい。
The composition of the present invention may be manufactured by mixing the components in any order.
Among these, from the viewpoint of efficiently producing the composition of the present invention, a phosphor dispersion containing the inorganic phosphor, the modified silicone dispersant, and the organic solvent is prepared in advance, and this phosphor dispersion and the silicone It is preferable to manufacture the composition of the present invention by mixing the resin, the photopolymerizable compound, the photopolymerization initiator, and the organic solvent.
前記蛍光体分散体と混合するための、前記シリコーン系樹脂、前記光重合性化合物、前記光重合開始剤及び前記有機溶剤については、これらの成分を混合したレジスト溶液としてもよい。この場合、蛍光体分散体とレジスト溶液との混合比率（重量比）は３：７～７：３の範囲で好ましく選択できる。 The silicone resin, the photopolymerizable compound, the photopolymerization initiator, and the organic solvent to be mixed with the phosphor dispersion may be a resist solution in which these components are mixed. In this case, the mixing ratio (weight ratio) of the phosphor dispersion and the resist solution can be preferably selected within the range of 3:7 to 7:3.
前記蛍光体分散体、前記シリコーン系樹脂、前記光重合性化合物、前記光重合開始剤及び前記有機溶剤を混合する方法としては、公知の混合方法を利用できる。 A known mixing method can be used to mix the phosphor dispersion, the silicone resin, the photopolymerizable compound, the photopolymerization initiator, and the organic solvent.
（蛍光体分散体）
本発明に係る蛍光体分散体（以下、本発明の分散体ともいう）に含有される前記無機蛍光体、前記変性シリコーン系分散剤及び前記有機溶剤は、いずれも本発明の組成物に使用できるものであればよい。
(phosphor dispersion)
The inorganic phosphor, the modified silicone dispersant, and the organic solvent contained in the phosphor dispersion of the present invention (hereinafter also referred to as the dispersion of the present invention) can all be used in the composition of the present invention. It is fine as long as it is something.
中でも、本発明の分散体では、本発明の効果が奏されやすい観点から、前記変性シリコーン系分散剤が脂肪族変性シリコーンであることが好ましい。 Among these, in the dispersion of the present invention, it is preferable that the modified silicone-based dispersant is an aliphatic modified silicone from the viewpoint of easily achieving the effects of the present invention.
また、本発明の分散体は、本発明の効果が奏されやすい観点から、さらにシリコーン系樹脂を含有していることが好ましい。前記シリコーン系樹脂としては、本発明の組成物に使用できるものであればよい。 Moreover, it is preferable that the dispersion of the present invention further contains a silicone resin from the viewpoint of easily achieving the effects of the present invention. The silicone resin may be any silicone resin as long as it can be used in the composition of the present invention.
前記蛍光体分散体は、前記無機蛍光体、前記変性シリコーン系分散剤、前記有機溶剤、及び必要に応じて前記シリコーン系樹脂を混合することにより製造できる。前記無機蛍光体の分散性を高める等の目的で、前記無機蛍光体及び有機溶剤を含む分散体と、前記変性シリコーン系分散剤又はその有機溶剤溶液と、必要に応じてシリコーン系樹脂等とを混合することにより蛍光体分散体を製造してもよい。
また、前記無機蛍光体の有機溶剤への分散には、微細粒子の有機溶剤への分散に利用される種々の分散方法を利用できる。
The phosphor dispersion can be produced by mixing the inorganic phosphor, the modified silicone dispersant, the organic solvent, and, if necessary, the silicone resin. For the purpose of increasing the dispersibility of the inorganic phosphor, a dispersion containing the inorganic phosphor and an organic solvent, the modified silicone dispersant or its organic solvent solution, and, if necessary, a silicone resin etc. A phosphor dispersion may be manufactured by mixing.
Furthermore, various dispersion methods used for dispersing fine particles in an organic solvent can be used to disperse the inorganic phosphor in an organic solvent.
前記蛍光体分散体における各成分の含有量としては、例えば、
前記無機蛍光体２０～７０重量％、
前記変性シリコーン系分散剤２～３２重量％、
前記有機溶剤２０～７８重量％、
前記シリコーン系樹脂０～２０重量％
の範囲に調整されていればよい。
The content of each component in the phosphor dispersion is, for example,
20 to 70% by weight of the inorganic phosphor,
2 to 32% by weight of the modified silicone dispersant,
20 to 78% by weight of the organic solvent,
The silicone resin 0 to 20% by weight
It is sufficient if it is adjusted within the range of .
本発明の分散体は、本発明の組成物を作製する原料として使用できる以外に、波長変換の必要な場所に使用することもできる。 The dispersion of the present invention can be used not only as a raw material for producing the composition of the present invention, but also in places where wavelength conversion is required.
（波長変換層）
以上のようにして得られる本発明の分散体及び組成物は、自発光型ディスプレイの発光素子を構成する表示装置用基板の表面に形成される波長変換層の材料として使用することができる。
(wavelength conversion layer)
The dispersion and composition of the present invention obtained as described above can be used as a material for a wavelength conversion layer formed on the surface of a display device substrate constituting a light emitting element of a self-luminous display.
前記波長変換層は、本発明の分散体を表示装置用基板表面の所定領域にインクジェット塗布又はノズル塗布し、自然硬化又は加熱硬化させて、硬化層とすることにより形成される。
また、本発明の組成物を表示装置用基板表面の所定領域に塗布し、自然硬化又は加熱硬化させて、硬化層とすることにより形成される。
本発明の組成物の塗布方法としては公知の塗布（又は印刷）方法をいずれも採用できる。例えば、ロールコーティング、スピンコーティング、スロットコーティング、スクリーン印刷等の手法を利用できる。
The wavelength conversion layer is formed by inkjet coating or nozzle coating of the dispersion of the present invention on a predetermined region of the surface of a display device substrate, and by natural curing or heat curing to form a cured layer.
Moreover, the composition of the present invention is applied to a predetermined area on the surface of a display device substrate, and is naturally cured or heated to be cured to form a cured layer.
Any known coating (or printing) method can be employed as a method for applying the composition of the present invention. For example, techniques such as roll coating, spin coating, slot coating, and screen printing can be used.
表示装置用基板表面に塗布された本発明の組成物の塗膜は、例えば加熱や光照射により硬化される。該塗膜の加熱硬化において、加熱温度及び加熱時間は本発明の組成物に含まれる前記変性シリコーン系分散剤や有機溶剤の種類等に応じて適宜選択される。例えば８０～１２０℃程度の温度下で、１分～３０分程度でプリベーク加熱を行い、次いで２００～２５０℃程度の温度下に行なわれ、２０分～６０分程度で本加熱を行う。前記波長変換層の厚みは、有機ＥＬディスプレイの場合には、好ましくは０．５～１０μｍ程度、マイクロＬＥＤディスプレイの場合には、好ましくは１０～３０μｍ程度である。 The coating film of the composition of the present invention applied to the surface of the display device substrate is cured, for example, by heating or light irradiation. In heating and curing the coating film, the heating temperature and heating time are appropriately selected depending on the type of the modified silicone dispersant and organic solvent contained in the composition of the present invention. For example, prebake heating is performed at a temperature of about 80 to 120° C. for about 1 minute to 30 minutes, followed by main heating at a temperature of about 200 to 250° C. for about 20 to 60 minutes. The thickness of the wavelength conversion layer is preferably about 0.5 to 10 μm in the case of an organic EL display, and preferably about 10 to 30 μm in the case of a micro LED display.
以下に実施例及び比較例を挙げ、本発明を具体的に説明する。 EXAMPLES The present invention will be specifically described below with reference to Examples and Comparative Examples.
（製造例１：赤色系の蛍光体分散体１の製造）
表１に示す組成のように、赤色系無機蛍光体（以下、赤色蛍光体）と、変性シリコーン系分散剤Ａ（市販の脂肪族変性シリコーン）と、有機溶剤（プロピレングリコールモノメチルエーテルアセテート（ＰＧＭＡｃ））とを混合して赤色系の蛍光体分散体１を製造した（無機蛍光体の分散粒径３．８μｍ）。
前記蛍光分散体１は、その組成が無機蛍光体／変性シリコーン系分散剤／有機溶剤＝３６／７．２／５６．８（重量％）となるように調整した。
(Production Example 1: Production of red phosphor dispersion 1)
As shown in Table 1, the composition includes a red inorganic phosphor (hereinafter referred to as red phosphor), a modified silicone dispersant A (commercially available aliphatic modified silicone), and an organic solvent (propylene glycol monomethyl ether acetate (PGMAc)). ) to produce a red phosphor dispersion 1 (dispersed particle size of inorganic phosphor: 3.8 μm).
The composition of the fluorescent dispersion 1 was adjusted to be inorganic fluorescent substance/modified silicone dispersant/organic solvent=36/7.2/56.8 (wt%).
（製造例２：緑色系の蛍光体分散体２の製造）
表１に示す組成のように、赤色蛍光体に変えて緑色系無機蛍光体（以下、緑色蛍光体）を用いた以外は、製造例１と同様にして、緑色系の蛍光体分散体２を製造した（無機蛍光体の分散粒径３．７μｍ）。
前記蛍光分散体２は、その組成が無機蛍光体／変性シリコーン系分散剤／有機溶剤＝２８／５．６／６６．４（重量％）となるように調整した。
(Production Example 2: Production of green phosphor dispersion 2)
As shown in Table 1, green phosphor dispersion 2 was prepared in the same manner as in Production Example 1, except that a green inorganic phosphor (hereinafter referred to as green phosphor) was used instead of the red phosphor. (dispersed particle size of inorganic phosphor: 3.7 μm).
The composition of the fluorescent dispersion 2 was adjusted to be inorganic fluorescent substance/modified silicone dispersant/organic solvent=28/5.6/66.4 (wt%).
（製造例３：緑色系の蛍光体分散体３の製造）
表１に示す組成のように、変性シリコーン系分散剤として、変性シリコーン系分散剤Ｂ（市販の脂肪族変性シリコーン）を用いた以外は、製造例２と同様にして、緑色系の蛍光体分散体３を製造した（無機蛍光体の分散粒径３．９μｍ）。
前記蛍光分散体３は、その組成が無機蛍光体／変性シリコーン系分散剤／有機溶剤＝２８／５．６／６６．４（重量％）となるように調整した。
(Production Example 3: Production of green phosphor dispersion 3)
As shown in Table 1, green phosphor dispersion was carried out in the same manner as in Production Example 2, except that modified silicone dispersant B (commercially available aliphatic modified silicone) was used as the modified silicone dispersant. Sample 3 was produced (dispersed particle size of inorganic phosphor: 3.9 μm).
The composition of the fluorescent dispersion 3 was adjusted to be inorganic fluorescent substance/modified silicone dispersant/organic solvent=28/5.6/66.4 (wt%).
（製造例４：青色系の蛍光体分散体４の製造）
表１に示す組成のように、青色系無機蛍光体（以下、青色蛍光体）と、変性シリコーン系分散剤Ａと、有機溶剤（ＰＧＭＡｃ）とを混合して青色系の蛍光体分散体４を製造した（無機蛍光体の分散粒径４．９μｍ）。
前記蛍光体分散体４は、その組成が無機蛍光体／変性シリコーン系分散剤／有機溶剤＝３５／３．５／６１．５（重量％）となるように調整した。
前記蛍光分散体４は、その組成が無機蛍光体／変性シリコーン系分散剤／有機溶剤＝４２／４．２／５３．８（重量％）となるように調整した。
(Production Example 4: Production of blue phosphor dispersion 4)
As shown in Table 1, a blue inorganic phosphor (hereinafter referred to as blue phosphor), a modified silicone dispersant A, and an organic solvent (PGMAc) are mixed to form a blue phosphor dispersion 4. (dispersed particle size of inorganic phosphor: 4.9 μm).
The composition of the phosphor dispersion 4 was adjusted to be inorganic phosphor/modified silicone dispersant/organic solvent=35/3.5/61.5 (wt%).
The composition of the fluorescent dispersion 4 was adjusted to be inorganic fluorescent substance/modified silicone dispersant/organic solvent=42/4.2/53.8 (wt%).
（製造例５：赤色系の蛍光体分散体５の製造）
変性シリコーン系分散剤Ｃ（芳香族変性シリコーン）を用いた以外は、製造例１と同様にして、赤色系の蛍光体分散体５を製造した（無機蛍光体の分散粒径３．６μｍ）。
(Production Example 5: Production of red phosphor dispersion 5)
A red phosphor dispersion 5 was produced in the same manner as in Production Example 1, except that modified silicone-based dispersant C (aromatically modified silicone) was used (inorganic phosphor dispersed particle size: 3.6 μm).
（比較製造例１：赤色系の蛍光体分散体６の製造）
変性シリコーン系分散剤Ａを市販のアクリル樹脂Ａに変えた以外は、製造例１と同様にして赤色系の蛍光体分散体６を製造した（無機蛍光体の分散粒径３．２μｍ）。
(Comparative production example 1: Production of red phosphor dispersion 6)
A red phosphor dispersion 6 was produced in the same manner as Production Example 1 except that the modified silicone dispersant A was replaced with a commercially available acrylic resin A (inorganic phosphor dispersed particle size: 3.2 μm).
（比較製造例２：青色系の蛍光体分散体７の製造）
変性シリコーン系分散剤Ａを市販のアクリル樹脂Ａに変えた以外は、製造例４と同様にして青色系の蛍光体分散体７を製造した（無機蛍光体の分散粒径４．１μｍ）。
(Comparative Production Example 2: Production of Blue Phosphor Dispersion 7)
A blue phosphor dispersion 7 was produced in the same manner as Production Example 4, except that the modified silicone dispersant A was replaced with a commercially available acrylic resin A (inorganic phosphor dispersed particle size: 4.1 μm).
（比較製造例３：赤色系の蛍光体分散体８の製造）
変性シリコーン系分散剤Ａを市販のアクリル樹脂Ｂに変えた以外は、製造例１と同様にして赤色系の蛍光体分散体８を製造した（無機蛍光体の分散粒径３．１μｍ）。
(Comparative Production Example 3: Production of red phosphor dispersion 8)
A red phosphor dispersion 8 was produced in the same manner as in Production Example 1, except that the modified silicone dispersant A was replaced with a commercially available acrylic resin B (the dispersed particle size of the inorganic phosphor was 3.1 μm).
（比較製造例４：緑色系の蛍光体分散体９の製造）
変性シリコーン系分散剤Ａを市販のアクリル樹脂Ｂに変えた以外は、製造例２と同様にして緑色系の蛍光体分散体９を製造した（無機蛍光体の分散粒径３．６μｍ）。
(Comparative Production Example 4: Production of Green Phosphor Dispersion 9)
A green phosphor dispersion 9 was produced in the same manner as in Production Example 2, except that the modified silicone dispersant A was replaced with a commercially available acrylic resin B (the dispersed particle size of the inorganic phosphor was 3.6 μm).
（比較製造例５：青色系の蛍光体分散体１０の製造）
変性シリコーン系分散剤Ａを市販のアクリル樹脂Ｂに変えた以外は、製造例４と同様にして青色系の蛍光体分散体１０を製造した（無機蛍光体の分散粒径４．３μｍ）。
(Comparative Production Example 5: Production of blue-colored phosphor dispersion 10)
A blue phosphor dispersion 10 was produced in the same manner as in Production Example 4, except that the modified silicone dispersant A was replaced with a commercially available acrylic resin B (the dispersed particle size of the inorganic phosphor was 4.3 μm).
（実施例１：赤色系の蛍光体感光性組成物１の製造）
表１に示す組成となるように、製造例１で作製した蛍光体分散体１に対して、樹脂組成物の母材としてシリコーン系樹脂（光硬化型シロキサン樹脂Ｄ）、光重合性化合物Ｅ、光重合開始剤Ｆ及び有機溶剤を添加し、均一になるように混合して赤色系の蛍光体感光性組成物１（固形分中の蛍光体濃度４０重量％）を製造した。
(Example 1: Production of red phosphor photosensitive composition 1)
In order to obtain the composition shown in Table 1, for the phosphor dispersion 1 produced in Production Example 1, silicone resin (photocurable siloxane resin D), photopolymerizable compound E, Photopolymerization initiator F and an organic solvent were added and mixed uniformly to produce red phosphor photosensitive composition 1 (phosphor concentration 40% by weight in solid content).
（実施例２、３：緑色系の蛍光体感光性組成物２、３の製造）
表１に示す組成となるように、実施例１と同様にして、緑色系の蛍光体感光性組成物２、３を作製した。
(Examples 2 and 3: Production of green phosphor photosensitive compositions 2 and 3)
Green phosphor photosensitive compositions 2 and 3 were prepared in the same manner as in Example 1 so as to have the compositions shown in Table 1.
（実施例４：青色系の蛍光体感光性組成物４の製造）
表１に示す組成となるように、実施例１と同様にして青色系の蛍光体感光性組成物４を作製した。
(Example 4: Production of blue-based phosphor photosensitive composition 4)
A blue phosphor photosensitive composition 4 was prepared in the same manner as in Example 1 so as to have the composition shown in Table 1.
（実施例５：赤色系の蛍光体感光性組成物５の製造）
表１に示す組成となるように、実施例１と同様にして赤色系の蛍光体感光性組成物５を作製した。
(Example 5: Production of red phosphor photosensitive composition 5)
A red phosphor photosensitive composition 5 was prepared in the same manner as in Example 1 so as to have the composition shown in Table 1.
（比較例１：赤色系の蛍光体感光性組成物６の製造）
表１に示す組成となるように、実施例１と同様にして赤色系の蛍光体感光性組成物６を作製した。
(Comparative Example 1: Production of red phosphor photosensitive composition 6)
A red phosphor photosensitive composition 6 was prepared in the same manner as in Example 1 so as to have the composition shown in Table 1.
（比較例２：青色系の蛍光体感光性組成物７の製造）
表１に示す組成となるように、実施例１と同様にして青色系の蛍光体感光性組成物７を作製した。
(Comparative Example 2: Production of blue-based phosphor photosensitive composition 7)
Blue phosphor photosensitive composition 7 was prepared in the same manner as in Example 1 so as to have the composition shown in Table 1.
（比較例３：赤色系の蛍光体感光性組成物８の製造）
表１に示す組成となるように、実施例１と同様にして赤色系の蛍光体感光性組成物８を作製した。
(Comparative Example 3: Production of red phosphor photosensitive composition 8)
A red phosphor photosensitive composition 8 was prepared in the same manner as in Example 1 so as to have the composition shown in Table 1.
（比較例４：緑色系の蛍光体感光性組成物９の製造）
表１に示す組成となるように、実施例１と同様にして緑色系の蛍光体感光性組成物９を作製した。
(Comparative Example 4: Production of green phosphor photosensitive composition 9)
A green phosphor photosensitive composition 9 was prepared in the same manner as in Example 1 so as to have the composition shown in Table 1.
（比較例５：青色系の蛍光体感光性組成物１０の製造）
表１に示す組成となるように、実施例１と同様にして青色系の蛍光体感光性組成物１０を作製した。
(Comparative Example 5: Production of blue-based phosphor photosensitive composition 10)
A blue phosphor photosensitive composition 10 was prepared in the same manner as in Example 1 so as to have the composition shown in Table 1.
（試験例１：現像性評価）
スピンコーター（ミカサ（株）製）を用いて、実施例１～５、比較例１～５で作製した感光性組成物を１０ｃｍ角の無アルカリガラス基板上に、キュア後の膜厚が１５μｍとなるように塗布し、ホットプレート（アズワン（株）製）を用いて温度１００℃で３分間プリベークし、プリベーク膜を形成した。作製したプリベーク膜を、パラレルライトマスクアライナー（（株）トプコン製）を用いて、超高圧水銀灯を光源とし、マスクを介さず、露光量２００ｍＪ／ｃｍ２（ｇｈｉ線）で、１００μｍのギャップで露光した。その後、自動現像装置（ミカサ（株）製「ＡＤ－１２００（商品名）」）を用いて、０．５重量％水酸化ナトリウム水溶液を用いてシャワー現像し、次いで水を用いて１５秒間リンスした。リンス後の基板を２３０℃で３０分間乾燥して、波長変換層を得た。
シャワー現像に要した現像時間及び現像状態の結果を表２に示す。
前記現像状態については、溶解現象が良好な結果であり、一方、剥離現像であるとうまく像（パターン）が現れないことを示す。
(Test Example 1: Developability evaluation)
Using a spin coater (manufactured by Mikasa Co., Ltd.), the photosensitive compositions prepared in Examples 1 to 5 and Comparative Examples 1 to 5 were coated onto a 10 cm square alkali-free glass substrate so that the film thickness after curing was 15 μm. The film was coated so as to be coated and prebaked for 3 minutes at a temperature of 100° C. using a hot plate (manufactured by As One Co., Ltd.) to form a prebaked film. The prepared prebaked film was exposed to light using a parallel light mask aligner (manufactured by Topcon Corporation) using an ultra-high pressure mercury lamp as a light source, without using a mask, at an exposure dose of 200 mJ/cm2 (ghi line) with a gap of 100 μm. . Thereafter, using an automatic developing device ("AD-1200 (trade name)" manufactured by Mikasa Co., Ltd.), shower development was performed using a 0.5% by weight sodium hydroxide aqueous solution, and then rinsed with water for 15 seconds. . The rinsed substrate was dried at 230° C. for 30 minutes to obtain a wavelength conversion layer.
Table 2 shows the results of the development time and development conditions required for shower development.
Regarding the development state, the dissolution phenomenon is a good result, whereas the peeling development shows that the image (pattern) does not appear well.
表２に示すように、本発明を適用した実施例１は、分散剤としてアクリル樹脂Ｂを用いた比較例３に比べて、短時間でシャワー現像ができることから、良好なアルカリ溶解性を有し、現像性が優れることが分かった。
本発明を適用した実施例２及び実施例３は、分散剤としてアクリル樹脂Ｂを用いた比較例４に比べて、短時間でシャワー現像ができることから、良好なアルカリ溶解性を有し、現像性が優れることが分かった。
本発明を適用した実施例４は、分散剤としてアクリル樹脂Ｂを用いた比較例５に比べて、短時間でシャワー現像ができることから、良好なアルカリ溶解性を有し、現像性が優れることが分かった。
なお、本発明を適用した実施例１は、分散剤として変性部位が芳香族系である変性シリコーン系分散剤Ｃを用いた比較例５に比べて、短時間でシャワー現像ができ、良好なアルカリ溶解性を有し、現像性が優れることが分かった。
As shown in Table 2, Example 1 to which the present invention is applied can perform shower development in a shorter time than Comparative Example 3, which uses acrylic resin B as a dispersant, and has good alkali solubility. It was found that the developability was excellent.
Examples 2 and 3 to which the present invention is applied can perform shower development in a shorter time than Comparative Example 4 in which acrylic resin B was used as a dispersant, so they have good alkali solubility and developability. was found to be superior.
Example 4 to which the present invention is applied can perform shower development in a shorter time than Comparative Example 5 in which acrylic resin B was used as a dispersant, indicating that it has good alkali solubility and excellent developability. Do you get it.
In addition, in Example 1 to which the present invention is applied, compared to Comparative Example 5 in which a modified silicone-based dispersant C having an aromatic modified moiety was used as a dispersant, shower development can be performed in a shorter time and a good alkali property is obtained. It was found that it has solubility and excellent developability.
［試験例２：耐湿熱性評価］
試験例１で得られた波長変換層について、１ｃｍ角に切り出し、絶対量子収率測定装置（浜松ホトニクス（株）製「C１１３４７（商品名）」）にて３８５ｎｍの励起光における量子収率、吸収率、発光強度、半値幅を測定した。また、波長変換層を３８５ｎｍの光を発するＬＥＤ素子の上に配置し、ＬＥＤ素子を発光させて、正面輝度計（コニカミノルタ（株）製「ＣＳ－１０００（商品名）」）にて発光スペクトルを測定した（初期）。
次いで、波長変換層が形成された基板を恒温恒湿槽（エスペック（株）製）に入れ、温度８５℃、湿度８５％で５００時間加熱した。上記基板を室温（１５～２５℃）で一晩静置後、上記の量子収率測定装置及び正面輝度計を用いて測定した（加熱後）。得られたスペクトルから、量子収率の変化率（ΔＰＬＱＹ）、発光強度の変化率（Δピーク強度）、光学濃度の変化率（ΔＯＤ）をそれぞれ計算し、結果を表２に示す。
[Test Example 2: Moisture heat resistance evaluation]
The wavelength conversion layer obtained in Test Example 1 was cut into 1 cm square pieces, and the quantum yield and absorption at 385 nm excitation light were measured using an absolute quantum yield measurement device (“C11347 (trade name)” manufactured by Hamamatsu Photonics Co., Ltd.). The rate, luminescence intensity, and half-width were measured. In addition, the wavelength conversion layer was placed on top of an LED element that emits light of 385 nm, the LED element was made to emit light, and the emission spectrum was measured using a front luminance meter ("CS-1000 (trade name)" manufactured by Konica Minolta, Inc.). was measured (initial stage).
Next, the substrate on which the wavelength conversion layer was formed was placed in a constant temperature and humidity chamber (manufactured by ESPEC Co., Ltd.) and heated at a temperature of 85° C. and a humidity of 85% for 500 hours. The above-mentioned substrate was left standing at room temperature (15 to 25°C) overnight, and then measured using the above-mentioned quantum yield measuring device and front luminance meter (after heating). From the obtained spectrum, the rate of change in quantum yield (ΔPLQY), the rate of change in emission intensity (Δpeak intensity), and the rate of change in optical density (ΔOD) were calculated, and the results are shown in Table 2.
表２に示すように、本発明を適用した実施例１は、分散剤としてアクリル樹脂Ａを用いた比較例１に比べて、発光強度の変化率が小さく、耐湿熱性が優れることが分かった。
本発明を適用した実施例２及び実施例３は、分散剤としてアクリル樹脂Ｂを用いた比較例４に比べて、発光強度の変化率が小さく、耐湿熱性が優れることが分かった。
本発明を適用した実施例４は、分散剤としてアクリル樹脂Ａを用いた比較例２、及びアクリル樹脂Ｂを用いた比較例５に比べて、発光強度の変化率が小さく、耐湿熱性が優れることが分かった。
以上のことから、製造例１～５で作製した分散体１～５、及び実施例１～５で作製した感光性組成物１～５はいずれも耐熱性及び現像性に優れたものであることがわかった。
As shown in Table 2, it was found that Example 1 to which the present invention was applied had a smaller rate of change in luminescence intensity and superior moist heat resistance than Comparative Example 1 in which acrylic resin A was used as a dispersant.
It was found that Examples 2 and 3 to which the present invention was applied had a smaller rate of change in luminescence intensity and superior moist heat resistance than Comparative Example 4 in which acrylic resin B was used as a dispersant.
Example 4 to which the present invention was applied had a smaller rate of change in luminescence intensity and superior moist heat resistance than Comparative Example 2, which used acrylic resin A as a dispersant, and Comparative Example 5, which used acrylic resin B. I understand.
From the above, dispersions 1 to 5 prepared in Production Examples 1 to 5 and photosensitive compositions 1 to 5 prepared in Examples 1 to 5 are all excellent in heat resistance and developability. I understand.
Claims (8)
変性シリコーン系分散剤と、
シリコーン系樹脂と、
光重合性化合物と、
光重合開始剤と、
有機溶剤と
を含有することを特徴とする、蛍光体感光性組成物。 an inorganic phosphor that emits red fluorescence, green fluorescence or blue fluorescence;
A modified silicone dispersant,
silicone resin,
a photopolymerizable compound;
a photopolymerization initiator;
A phosphor photosensitive composition characterized by containing an organic solvent.
変性シリコーン系分散剤１～１６重量％、
シリコーン系樹脂５～２０重量％、
光重合性化合物１～１５重量％、
光重合開始剤０．１～３重量％、及び
有機溶剤１３～７４重量％を含有する、請求項１～３のいずれかに記載の蛍光体感光性組成物。 10 to 35% by weight of the inorganic phosphor,
Modified silicone dispersant 1 to 16% by weight,
silicone resin 5-20% by weight,
1 to 15% by weight of a photopolymerizable compound,
The phosphor photosensitive composition according to any one of claims 1 to 3, containing 0.1 to 3% by weight of a photopolymerization initiator and 13 to 74% by weight of an organic solvent.
変性シリコーン系分散剤と、
有機溶剤と
を含有することを特徴とする、蛍光体分散体。 an inorganic phosphor that emits red fluorescence, green fluorescence or blue fluorescence;
A modified silicone dispersant,
A phosphor dispersion characterized by containing an organic solvent.
分散体。 The phosphor dispersion according to claim 6, wherein the modified silicone-based dispersant is an aliphatic modified silicone.
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| JP2022060772A JP2023151257A (en) | 2022-03-31 | 2022-03-31 | Phosphor dispersion, and phosphor photosensitive composition using the same |
| CN202310268632.5A CN116893570A (en) | 2022-03-31 | 2023-03-20 | Phosphor dispersion and phosphor photosensitive composition using the same |
| KR1020230037486A KR20230141511A (en) | 2022-03-31 | 2023-03-22 | Phosphor dispersion and phosphor photosensitive composition using the same |
| TW112110976A TWI842450B (en) | 2022-03-31 | 2023-03-23 | Fluorescent dispersion and fluorescent photosensitive composition using the same |
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