JP2019109348A - Quantum dot, quantum dot-containing composition and ink jet ink - Google Patents
Quantum dot, quantum dot-containing composition and ink jet ink Download PDFInfo
- Publication number
- JP2019109348A JP2019109348A JP2017241887A JP2017241887A JP2019109348A JP 2019109348 A JP2019109348 A JP 2019109348A JP 2017241887 A JP2017241887 A JP 2017241887A JP 2017241887 A JP2017241887 A JP 2017241887A JP 2019109348 A JP2019109348 A JP 2019109348A
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- Prior art keywords
- quantum dot
- group
- ink
- semiconductor
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- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000010420 shell particle Substances 0.000 description 1
- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical class C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical class C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical class [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Ink Jet (AREA)
- Optical Filters (AREA)
- Luminescent Compositions (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
本発明は、量子ドット、量子ドットを含有する組成物、組成物を含有するインクジェットインキに関する。 The present invention relates to a quantum dot, a composition containing a quantum dot, and an inkjet ink containing the composition.
量子ドットは、量子力学に従う独特な光学特性を発現させるために、電子を微小な空間に閉じ込めるために形成された極小さな粒（ドット）である。１粒の量子ドットの大きさは、直径１ナノメートルから数１０ナノメートルであり、約１万個以下の原子で構成されている。発する蛍光の波長が、粒の大きさで連続的に制御できること、蛍光強度の波長分布が対称性の高いシャープな発光が得られることから近年注目を集めている。
量子ドットは、人体を透過しやすい波長に蛍光を調整でき、体内のあらゆる場所に送達できることより発光材料として生体イメージング用途（非特許文献１）、褪色の恐れがない波長変換材料として太陽電池用途（特許文献１）、鮮明な発光材料、波長変換材料としてエレクトロニクス・フォトニクス用途（特許文献２，３）への展開検討が行われている。
A quantum dot is a very small particle (dot) formed to confine electrons in a minute space in order to express unique optical properties according to quantum mechanics. The size of one quantum dot is 1 nanometer to several tens of nanometers in diameter, and is composed of about 10,000 or less atoms. In recent years, attention has been focused on that the wavelength of the emitted fluorescence can be continuously controlled by the particle size, and sharp emission with high symmetry of the wavelength distribution of the fluorescence intensity can be obtained.
Quantum dots can adjust fluorescence to a wavelength that is easily transmitted through the human body, and can be delivered to any place in the body, so they can be used as a luminescent material for bioimaging applications (Non-Patent Document 1), and as a wavelength conversion material without fear of fading. Patent Document 1), development of a clear light emitting material, and application to electronics and photonics (patent documents 2 and 3) as a wavelength conversion material has been conducted.
これらの用途に展開するときに、必要となる特性として、蛍光の量子収率があげられる。
蛍光収率を向上させるために、非特許文献２には、半導体微粒子をＩｎ−Ｐからなる半導体微粒子に有機脂肪族カルボン酸であるミリスチン酸で被覆する例が開示されている。
最近になり、非特許文献３には、１−ドデカンチオールで被覆する例が開示されている。
When developing for these applications, the required characteristics include the quantum yield of fluorescence.
In order to improve the fluorescence yield, Non-Patent Document 2 discloses an example in which semiconductor fine particles are coated with semiconductor fine particles made of In-P with myristic acid which is an organic aliphatic carboxylic acid.
Recently, Non-Patent Document 3 discloses an example of coating with 1-dodecanethiol.
塗布、印刷するためには、量子ドット単体では困難なため、溶剤やモノマーといった希釈材を用いるが、成形、塗布、印刷後に時間経過により、蛍光量子収率の低下が大きく低下してしまうことが課題となっていた。量子効率低下の抑制のために 量子ドット含有造形物全体をバリア剤で囲う方法があるが、加工性が低下するという欠点があった。 Since application and printing are difficult with quantum dots alone, diluents such as solvents and monomers are used, but the decrease in fluorescence quantum yield may be greatly reduced over time after molding, application, and printing. It was an issue. Although there is a method in which the entire quantum dot-containing shaped object is surrounded with a barrier agent in order to suppress the decrease in quantum efficiency, there is a disadvantage that the processability is lowered.
本発明の目的は、量子ドットの蛍光収率を向上するとともに、量子ドットを用いて造形物への着色、塗布、印刷した際に、蛍光特性を維持可能な耐性の高い量子ドットおよび量子ドットを含有する組成物、インクジェットインキを提供することである。 The object of the present invention is to improve the fluorescence yield of quantum dots and, when colored, coated or printed on a shaped object by using quantum dots, highly resistant quantum dots and quantum dots that can maintain fluorescence characteristics. It is an object of the present invention to provide an ink jet ink containing the composition.
本発明者は、前記課題を解決するために、鋭意検討した結果、特定の構造を有する処理剤で表面処理された半導体微粒子を用いることにより、量子効率を向上させるとともに、耐性を向上できることを見出した。 As a result of intensive studies to solve the above problems, the present inventors have found that quantum efficiency can be improved and resistance can be improved by using semiconductor fine particles surface-treated with a treatment having a specific structure. The
すなわち、本発明は、半導体微粒子が、下記一般式（１）で示される処理剤で表面処理されたことを特徴とする量子ドットに関する。
一般式（1）
式中、Ｘ１、Ｘ２は各々独立に直接結合、−ＣＨ２−、−ＣＨ＜、−Ｏ−、を表し
Ｒ１、Ｒ２は水素原子または、置換基を有していてもよい芳香族残基を表す。ただし、Ｒ１、とＲ２が同時に水素原子になることはない。
ｎ１、ｎ２は各々独立に１または２を表す。
That is, the present invention relates to a quantum dot characterized in that semiconductor fine particles are surface-treated with a treatment agent represented by the following general formula (1).
General formula (1)
In the formula, X 1 and X 2 each independently represent a direct bond, -CH 2- , -CH <, -O-, and R 1 and R 2 each represent a hydrogen atom or an aromatic group which may have a substituent. Represents a family residue. However, R 1 and R 2 can not simultaneously be hydrogen atoms.
n1 and n2 each independently represent 1 or 2.
また、本発明は、半導体微粒子が化合物半導体であることを特徴とする前記の量子ドットに関する。 The present invention also relates to the above-mentioned quantum dot, characterized in that the semiconductor fine particle is a compound semiconductor.
また、本発明は、半導体微粒子がコア・シェル型であり、一般式（１）で表される処理剤でシェル表面が処理されていることを特徴とする前記の量子ドットに関する。 The present invention also relates to the above-mentioned quantum dot, wherein the semiconductor fine particle is a core-shell type, and the shell surface is treated with the treatment agent represented by the general formula (1).
また、本発明は、前記の量子ドットと、さらに溶媒を含有することを特徴とする量子ドット含有組成物に関する。 The present invention also relates to a quantum dot-containing composition comprising the above-described quantum dot and a solvent.
また、本発明は、前記の量子ドット含有組成物を少なくとも含有し、粘度が３〜５０ｍPsであるインキジェットインキに関する。 The present invention also relates to an ink jet ink containing at least the quantum dot-containing composition described above and having a viscosity of 3 to 50 mPs.
また、本発明は、前記のインクジェットインキを用いて形成される印刷物に関する。 The present invention also relates to a printed material formed using the above-mentioned ink jet ink.
本発明の第１〜３の態様によれば、半導体量子ドットを含み、蛍光特性に優れた高信頼性の量子ドットが提供される。
また、本発明の第４〜５の態様によれば、溶媒やモノマーという希釈材を用いた作業性の良い蛍光特性に優れ、高い信頼性を有する量子ドット組成物が提供される。
According to the first to third aspects of the present invention, a highly reliable quantum dot including a semiconductor quantum dot and having excellent fluorescence characteristics is provided.
Further, according to the fourth to fifth aspects of the present invention, a quantum dot composition having excellent workability and good fluorescence characteristics using a diluent such as a solvent or a monomer and having high reliability is provided.
以下、本発明を詳細に説明する。なお、文中、特段記載のない限り、「部」および「％」は、「重量部」および「重量％」を表す。
本発明の量子ドットは、半導体微粒子が、一般式（１）で示される処理剤で表面処理されたことを特徴とする量子ドットである。
Hereinafter, the present invention will be described in detail. In the following description, “parts” and “%” represent “parts by weight” and “% by weight” unless otherwise specified.
The quantum dot of the present invention is a quantum dot characterized in that semiconductor fine particles are surface-treated with the treatment agent represented by the general formula (1).
＜半導体微粒子＞
本発明の半導体微粒子は、無機物を成分とする半導体であり、単一組成でも、コアシェル型でも、３層以上の複数層になっていてもよい。
本発明の半導体は、２族元素、１０属元素、１１族元素、１２族元素、１３族元素、１４族元素、１５族元素および１６族元素で示される元素の群から選ばれる少なくとも２種以上の元素を含む化合物からなる半導体である。
さらに好ましくは化合物半導体である。化合物半導体は、Ｚｎ、Ｃｄ、Ｂ、Ａｌ、Ｇａ、Ｉｎ、Ｃ、Ｓｉ、Ｇｅ、Ｓｎ、Ｎ、Ｐ、Ａｓ、Ｓｂ、Ｐｂ、Ｓ，Ｓｅ，Ｔｅで示される元素群から選ばれる少なくとも２種の元素を含む化合物からなる半導体である。
さらに好ましくは、人に対する安全性が懸念される元素を除いた、Ｚｎ、Ｂ、Ａｌ、Ｇａ、Ｉｎ、Ｃ、Ｓｉ、Ｇｅ、Ｓｎ、Ｎ、Ｐ、Ｓ，Ｔｅで示される元素群から選ばれる少なくとも２種の元素を含む化合物からなる半導体である。
可視光を発光する用途では、バンドギャップの狭さからＩｎを構成元素として含む半導体が、さらに好ましい。
<Semiconductor particles>
The semiconductor fine particle of the present invention is a semiconductor containing an inorganic substance as a component, and may have a single composition, a core-shell type, or a plurality of layers of three or more layers.
The semiconductor of the present invention is at least two or more selected from the group of elements represented by Group 2 elements, Group 10 elements, Group 11 elements, Group 12 elements, Group 13 elements, Group 14 elements, Group 15 elements and Group 16 elements. A semiconductor comprising a compound containing the elements of
More preferably, they are compound semiconductors. The compound semiconductor is at least two selected from the group of elements represented by Zn, Cd, B, Al, Ga, In, C, Si, Ge, Sn, N, P, As, Sb, Pb, S, Se, and Te. A semiconductor comprising a compound containing the elements of
More preferably, it is selected from the group of elements represented by Zn, B, Al, Ga, In, C, Si, Ge, Sn, N, P, S, and Te except for elements which are of concern for human safety. It is a semiconductor composed of a compound containing at least two elements.
In applications that emit visible light, a semiconductor containing In as a constituent element is more preferable because of the narrow band gap.
コアシェル型の半導体微粒子はコアを形成する半導体と異なる成分からなる半導体でコア構造を被覆された構造となる。外部がバントギャップの大きい半導体をすることで、光励起によって生成された励起子（電子−正孔対）はコア内に閉じ込められる。その結果、半導体微粒子表面での無輻射遷移の確率が減少し、発光の量子収率および半導体量子ドットの蛍光特性の安定性が向上する。 The core-shell type semiconductor fine particles have a structure in which the core structure is covered with a semiconductor composed of components different from the semiconductor forming the core. When the outside is a semiconductor with a large band gap, excitons (electron-hole pairs) generated by light excitation are confined in the core. As a result, the probability of non-radiative transition on the surface of the semiconductor fine particle is reduced, and the quantum yield of light emission and the stability of the fluorescence characteristic of the semiconductor quantum dot are improved.
本発明の半導体微粒子の平均粒径は０．５ｎｍ〜１００ｎｍであることが好ましく、所望の発色が得られる粒径を選択することができる。コアシェル型の場合、一つの半導体微粒子の中に複数のシェル微粒子を含有してもよい。単一半導体組成である場合の半導体微粒子の平均粒径および、コアシェル型のコアの平均粒径は０．５ｎｍ〜１０ｎｍであることが好ましい。平均粒径が０．５ｎｍ未満となる合成は困難であり、また、１０ｎｍを超えると量子閉じ込め効果が得られず、求める蛍光が得られない。 The average particle diameter of the semiconductor fine particles of the present invention is preferably 0.5 nm to 100 nm, and the particle diameter at which desired color development can be obtained can be selected. In the case of the core-shell type, a plurality of shell particles may be contained in one semiconductor particle. The average particle size of the semiconductor particles and the average particle size of the core-shell type core in the case of the single semiconductor composition are preferably 0.5 nm to 10 nm. Synthesis with an average particle size of less than 0.5 nm is difficult, and when it exceeds 10 nm, the quantum confinement effect can not be obtained, and the desired fluorescence can not be obtained.
本発明の量子ドットは、平均粒径が2ｎｍ〜1μｍであることが好ましい。
量子ドットの形状は、球状に限らず、棒状、円盤状、そのほかの形状であっても良い。
The quantum dots of the present invention preferably have an average particle diameter of 2 nm to 1 μm.
The shape of the quantum dot is not limited to spherical, and may be rod-like, disk-like, or any other shape.
＜処理剤＞
本発明の処理剤は、一般式（１）に示す処理剤である。
<Treatment agent>
The treating agent of the present invention is a treating agent represented by the general formula (1).
一般式（1）
式中、Ｘ１、Ｘ２は各々独立に直接結合、−ＣＨ２−、−ＣＨ＜、−Ｏ−、を表し
Ｒ１、Ｒ２は水素原子または、置換基を有していてもよい芳香族残基を表す。ただし、Ｒ１、とＲ２が同時に水素原子になることはない。
ｎ１、ｎ２は各々独立に１または２を表す。
General formula (1)
In the formula, X 1 and X 2 each independently represent a direct bond, -CH 2- , -CH <, -O-, and R 1 and R 2 each represent a hydrogen atom or an aromatic group which may have a substituent. Represents a family residue. However, R 1 and R 2 can not simultaneously be hydrogen atoms.
n1 and n2 each independently represent 1 or 2.
本発明のＸ１、Ｘ２におけて、直接結合とは、リンとＲ１またはＲ２が直接結合することを示す。
Ｒ１、Ｒ２において、置換基を有していてもよい芳香族残基とは、芳香環から形式的に水素を１つ取り除いた残基である。芳香環の例として、ベンゼン環、ナフタレン環、ピレン環、ピリジン環、ピリミジン環、ピリダジン環、ピラジン環、キノリン環、フラン環、ピロール環、チオフェン環、イミダゾール環、ピラゾール環、オキサゾール環、チアゾール環、インドール環、ベンズイミダゾール環、ベンゾフラン環、プリン環、アクリジン環、フェノチアジン環などをあげることができる。
これらの芳香族残基は、置換されていてもよい。置換基としては、アルキル基、アルキル基で置換されていてもよいフェニル基、一般式（２）で表される置換基、または、エーテル基、チオエーテル基、ケトン基、エステル基を介して結合したアルキル基もしくはアルキル基で置換されていてもよいフェニル基が挙げられる。
芳香族残基が有してもよいアルキル基としては、直鎖、分岐、環状のアルキル基である。例えば、メチル、エチル、ヘキシル、ドデシル、エイコシル等の直鎖アルキル基、２−エチルヘキシル等の分岐アルキル基、シクロヘキシル基、３−シクロヘキシルプロピル基等の環状アルキル基があげられる。
In X 1 and X 2 of the present invention, direct bonding means that phosphorus is directly bonded to R 1 or R 2 .
In R 1 and R 2 , the aromatic residue which may have a substituent is a residue in which one hydrogen is formally removed from the aromatic ring. Examples of the aromatic ring include benzene ring, naphthalene ring, pyrene ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, quinoline ring, furan ring, pyrrole ring, thiophene ring, imidazole ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring And indole ring, benzimidazole ring, benzofuran ring, purine ring, acridine ring, phenothiazine ring and the like.
These aromatic residues may be substituted. The substituent is an alkyl group, a phenyl group which may be substituted by an alkyl group, a substituent represented by the general formula (2), or an ether group, a thioether group, a ketone group or an ester group. There may be mentioned an alkyl group or a phenyl group which may be substituted by an alkyl group.
The alkyl group which the aromatic residue may have is a linear, branched or cyclic alkyl group. Examples thereof include linear alkyl groups such as methyl, ethyl, hexyl, dodecyl and eicosyl, branched alkyl groups such as 2-ethylhexyl, and cyclic alkyl groups such as cyclohexyl and 3-cyclohexylpropyl.
一般式（２）
Ｑは−Ｏ−ＣＨ２−ＣＨ２−、−Ｏ−ＣＨ（ＣＨ３）−ＣＨ２−、−Ｏ−ＣＨ２−ＣＨ（ＣＨ３）−、フェニレン基、オキシフェニレン基、チオフェニレン基を
ｎ３は２〜１０の整数を
Ｒ３は水素、炭素数１〜８のアルキル基、炭素数１〜８のアルコキシ基、炭素１〜８のアルキルチオ基を表す。
芳香族残基への置換基の置換数は特に制限はなく、芳香環に結合している水素の数だけ可能である。
General formula (2)
Q is -O-CH 2 -CH 2 -, - O-CH (CH 3) -CH 2 -, - O-CH 2 -CH (CH 3) -, phenylene, oxyphenylene group, a thiophenylene group n3 Represents an integer of 2 to 10, R 3 represents hydrogen, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkylthio group having 1 to 8 carbon atoms.
The number of substituents of the aromatic residue is not particularly limited, and may be as many as the number of hydrogens bonded to the aromatic ring.
処理剤の具体例を以下に示すが、限定されるものではない。
Ａ群
Ｂ群
Ｃ群
Ｄ群
Ｅ群
A group
B group
C group
D group
E group
Ａ群の処理剤は、該当する芳香族化合物を塩化アルミニウム存在下で三塩化リンを作用させ、次いで塩素で処理し、その後水で加水分解することで得るができる。
Ｂ群の処理剤は、該当するメチル化芳香族化合物を亜リン酸エチルと反応させ、その後、塩酸で処理して、酸化と加水分解を行い得ること事ができる。
Ｃ群の処理剤は、オキシ塩化リンと順次当該化合物を反応させた後、加水分解することで得ることができる。
Ｄ群の処理剤は、フェニルフォスホン酸をニトロ化し、還元後、エチル化して得ることができる。
Ｅ群の処理剤は東京化成株式会社より試薬として購入することができる。
A group A treating agent can be obtained by treating the corresponding aromatic compound with phosphorus trichloride in the presence of aluminum chloride, then treating with chlorine and then hydrolyzing with water.
The Group B treating agents can be reacted with the corresponding methylated aromatic compound with ethyl phosphite and then treated with hydrochloric acid to effect oxidation and hydrolysis.
The treating agent of group C can be obtained by reacting phosphorus oxychloride sequentially with the compound and then hydrolyzing it.
The group D treating agent can be obtained by nitrating phenylphosphonic acid, reducing it and then ethylating it.
The treatment agent of group E can be purchased as a reagent from Tokyo Kasei Co., Ltd.
本発明の組成物が含んでもよい溶剤は、着色剤を十分に樹脂中に分散させ、ガラス基板等の基板上に本発明の着色組成物を乾燥膜厚が所望の膜厚になるように塗布することを容易にするために用いられる。
本発明の量子ドットを含む組成物は、溶剤を用いて、粘度を３〜５０ｍＰａ・ｓに調製して、インクジェットインキとして使用することもできる。インクジェットインキには印刷物への要求物性により、樹脂、架橋剤、重合性単量体、光感応性物質、熱感応性物質を添加することができる。
樹脂、架橋剤、重合性単量体、光感応性物質、熱感応性物質の添加物質の添加量としては、所望の量子ドット濃度により、量子ドット１重量部に対し、添加物質を０〜１００重量部添加することができる。１００重量部を超えると量子ドット含有率が低くなり、十分な蛍光強度が得られない。
The solvent which may be contained in the composition of the present invention sufficiently disperses the coloring agent in the resin, and the colored composition of the present invention is coated on a substrate such as a glass substrate so that the dry film thickness becomes a desired film thickness. It is used to make it easy to do.
The composition containing the quantum dot of the present invention can also be used as an inkjet ink by adjusting the viscosity to 3 to 50 mPa · s using a solvent. A resin, a crosslinking agent, a polymerizable monomer, a photosensitive material, and a heat sensitive material can be added to the inkjet ink depending on the physical properties required for the printed matter.
The addition amount of the resin, the crosslinking agent, the polymerizable monomer, the photosensitive substance, and the heat-sensitive substance is 0 to 100 parts by weight of the additive per 1 part by weight of the quantum dot according to the desired quantum dot concentration. It can be added in parts by weight. If it exceeds 100 parts by weight, the quantum dot content is low, and sufficient fluorescence intensity can not be obtained.
本発明の量子ドットを含む組成物を用いて、塗布し、紫外線照射により、フォトリソグラフィー法によりパターニングする際には、光感応性物質、重合性単量体を添加して、ポジ型レジスト、または、ネガ型レジストとすることができる。これらを単独で、または２種以上混合して用いることができる。 When the composition containing the quantum dot of the present invention is applied, and is patterned by photolithography by ultraviolet irradiation, a photosensitive substance, a polymerizable monomer are added to form a positive resist, or And negative resists. These can be used alone or in combination of two or more.
溶剤としては、
トルエン、１,２,３−トリクロロプロパン、１,３-ブチレングリコール、１,３-ブチレングリコールジアセテート、１,４−ジオキサン、２−ヘプタノン、２−メチル−１,３−プロパンジオール、３,５,５-トリメチル-２-シクロヘキセン-１-オン、３,３,５−トリメチルシクロヘキサノン、３−エトキシプロピオン酸エチル、３−メチル−１,３−ブタンジオール、３−メトキシ−３−メチル−１−ブタノール、３−メトキシ−３−メチルブチルアセテート、３-メトキシブタノール、３−メトキシブチルアセテート、４−ヘプタノン、ｍ−キシレン、ｍ−ジエチルベンゼン、ｍ−ジクロロベンゼン、Ｎ，Ｎ−ジメチルアセトアミド、Ｎ，Ｎ−ジメチルホルムアミド、ｎ−ブチルアルコール、ｎ−ブチルベンゼン、ｎ−プロピルアセテート、Ｎ−メチルピロリドン、o−キシレン、o−クロロトルエン、ｏ−ジエチルベンゼン、ｏ−ジクロロベンゼン、Ｐ−クロロトルエン、Ｐ−ジエチルベンゼン、ｓｅｃ−ブチルベンゼン、ｔｅｒｔ−ブチルベンゼン、γ―ブチロラクトン、水、メタノール、エタノール、イソプロピルアルコール、ターシャルターシャルブタノール、イソブチルアルコール、イソホロン、エチレングリコールジエチルエーテル、エチレングリコールジブチルエーテル、エチレングリコールモノイソプロピルエーテル、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エチルエーテルアセテート、エチレングリコールモノターシャリーブチルエーテル、エチレングリコールモノブチルエーテル、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プロピルエーテル、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モノメチルエーテル、エチレングリコールモノメチルエーテルアセテート、ジイソブチルケトン、ジエチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノイソプロピルエーテル、ジエチレングリコールモノエチルエーテルアセテート、ジ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ブチルエーテルアセテート、ジエチレングリコールモノメチルエーテル、シクロヘキサノール、シクロヘキサノールアセテート、シクロヘキサノン、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールメチルエーテルアセテート、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ブチルエーテル、ジプロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノメチルエーテル、ダイアセトンアルコール、トリアセチン、トリプロピレングリコールモノブチルエーテル、トリ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ジアセテート、プロピレングリコールフェニルエーテル、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エチルエーテルアセテート、プロピレングリコールモノブチルエーテル、プロピレングリコールモノプロピルエーテル、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メチルエーテルアセテート、プロピレングリコールモノメチルエーテルプロピオネート、ベンジルアルコール、メチルイソブチルケトン、メチルシクロヘキサノール、酢酸ｎ−アミル、酢酸ｎ−ブチル、酢酸イソアミル、酢酸イソブチル、酢酸プロピル、及び二塩基酸エステル等が挙げられる。
これらの溶剤は、１種を単独で、または必要に応じて任意の比率で２種以上混合して用いることができる。
As a solvent,
Toluene, 1,2,3-trichloropropane, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3, 3, 5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1 -Butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N, N-dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butyl benzene, n-propyl acetate, N-methyl acetate Pyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, P-chlorotoluene, P-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, water, methanol, ethanol, Isopropyl alcohol, tertiary butanol, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene Glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol Recall monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether Acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl Ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene Glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol Le, methyl isobutyl ketone, methyl cyclohexanol, acetic acid n- amyl acetate n- butyl, isoamyl acetate, isobutyl acetate, propyl acetate, and dibasic acid esters.
These solvents may be used alone or in combination of two or more at an arbitrary ratio as needed.
インクジェットインキとする場合には、樹脂に対する溶解性、装置部材に対する膨潤作用、粘度、及びノズルにおけるインキの乾燥性の点から選択され、一般式（３）：Ｒ４−（Ｏ−Ｃ2Ｈ4）m−Ｏ−Ｃ（＝Ｏ）−ＣＨ3［ただし、Ｒ４は炭素原子数１〜８のアルキル基であり、Ｃ2Ｈ4は直鎖若しくは分岐エチレン鎖であり、１≦ｍ≦３である。］で表される溶剤（Ａ−１）、及び一般式（４）：Ｒ５−（Ｏ−Ｃ3Ｈ6）p−Ｏ−Ｃ（＝Ｏ）−ＣＨ3［ただし、Ｒ５は炭素原子数１〜８のアルキル基であり、Ｃ3Ｈ6は直鎖若しくは分岐プロピレン鎖であり、１≦ｎ≦３である。］で表される溶剤（Ａ−２）、及びアセテート構造を２つ以上持つ溶剤（Ａ−３）からなる群から選ばれる７６０ｍｍＨｇでの沸点が１３５℃以上の１種類以上の溶剤を含むことが好ましい。
さらに好ましくは、前記７６０ｍｍＨｇでの沸点が１３５℃以上の溶剤が全溶剤中６０重量％以上含むことが吐出安定性やノズルにおけるインキの乾燥性の点から好ましい。
前記溶剤の具体例としては、例えばジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート、ジプロピレングリコールメチルエーテルアセテート、プロピレングリコールジアセテート、１，３−ブチレングリコールジアセテート、１，６−ヘキサンジオールジアセテート、トリアセチン等を挙げることができるが、必ずしもこれに限定されるものではない。中でも、好ましくはジエチレングリコールモノエチルエーテルアセテート、ジプロピレングリコールメチルエーテルアセテート、プロピレングリコールメチルエーテルアセテート、１，３−ブチレングリコールジアセテートが、吐出安定性の点から好ましい。
In the case of using an inkjet ink, it is selected from the viewpoint of solubility in resin, swelling action on device members, viscosity, and drying property of the ink at the nozzle, and the general formula (3): R 4- (O-C 2 H 4 ) M —O—C (= O) —CH 3 [wherein R 4 is an alkyl group having 1 to 8 carbon atoms, C 2 H 4 is a linear or branched ethylene chain, 1 ≦ m ≦ 3 It is. A solvent represented by Formula (A-1), and General Formula (4): R 5- (O-C 3 H 6 ) pO-C (= O) -CH 3 [wherein, R 5 represents a carbon atom an alkyl group having 1 to 8, C 3 H 6 is straight or branched propylene chain, 1 ≦ n ≦ 3. Containing one or more solvents having a boiling point of 135 ° C. or higher at 760 mmHg selected from the group consisting of a solvent (A-2) and a solvent (A-3) having two or more acetate structures preferable.
More preferably, the solvent having a boiling point of 135 ° C. or more at 760 mmHg is contained in an amount of 60% by weight or more based on the total solvent, from the viewpoint of discharge stability and ink drying property at the nozzle.
Specific examples of the solvent include, for example, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate, propylene glycol diacetate, 1,3-butylene glycol diacetate, and 1,6-hexanediol diacetate. Although triacetin etc. can be mentioned, it is not necessarily limited to this. Among them, diethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, propylene glycol methyl ether acetate, and 1,3-butylene glycol diacetate are preferable from the viewpoint of discharge stability.
樹脂としては、石油系樹脂、マレイン酸樹脂、ニトロセルロース、セルロースアセテートブチレート、環化ゴム、塩化ゴム、アルキド樹脂、アクリル樹脂、ポリエステル樹脂、アミノ樹脂、ビニル樹脂、又はブチラール樹脂等があげられ、基材により適時選択することができる。
架橋剤としては、架橋剤はメラミン化合物、ベンゾグアナミン化合物、アクリレート系モノマー、カルボジイミド化合物、エポキシ化合物、オキセタン化合物、フェノール化合物、ベンゾオキサジン化合物、ブロック化カルン酸化合物、ブロック化イソシアネート化合物、及びシランカップリング剤からなる群から選ばれる化合物１種若しくは２種以上であることが耐熱耐性を持つ熱架橋性の架橋剤である点から好ましい。
Examples of the resin include petroleum resins, maleic acid resins, nitrocellulose, cellulose acetate butyrate, cyclized rubber, chlorinated rubber, alkyd resins, acrylic resins, polyester resins, amino resins, vinyl resins, butyral resins, etc. It can be selected timely depending on the substrate.
As the crosslinking agent, the crosslinking agent is a melamine compound, a benzoguanamine compound, an acrylate monomer, a carbodiimide compound, an epoxy compound, an oxetane compound, a phenol compound, a benzoxazine compound, a blocked carnic acid compound, a blocked isocyanate compound, and a silane coupling agent It is preferable from the viewpoint of being a thermally crosslinkable crosslinking agent having heat resistance, that one or more compounds selected from the group consisting of
＜重合性単量体＞
本発明に用いる重合性単量体には、紫外線や熱などにより硬化して樹脂を生成するモノマーもしくはオリゴマーが含まれ、これらを単独で、または２種以上混合して用いることができる。
重合性単量体としては、例えば、メチル（メタ）アクリレート、エチル（メタ）アクリレート、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、β−カルボキシエチル（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、１，６−ヘキサンジオールジ（メタ）アクリレート、グリセリンジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレート、トリプロピレングリコールジ（メタ）アクリレート、ネオペンチルグリコール変性トリメチロールプロパンジ（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、ペンタエリスリトールトリ（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、１，６−ヘキサンジオールジグリシジルエーテルジ（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、ネオペンチルグリコールジグリシジルエーテルジ（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、カプロラクトン変性ジペンタエリスリトールヘキサ（メタ）アクリレート、トリシクロデカニル（メタ）アクリレート、エステルアクリレート、メチロール化メラミンの（メタ）アクリル酸エステル、エポキシ（メタ）アクリレート、ウレタンアクリレート等の各種アクリル酸エステル及びメタクリル酸エステル、（メタ）アクリル酸、スチレン、酢酸ビニル、ヒドロキシエチルビニルエーテル、エチレングリコールジビニルエーテル、ペンタエリスリトールトリビニルエーテル、（メタ）アクリルアミド、Ｎ−ヒドロキシメチル（メタ）アクリルアミド、Ｎ−ビニルホルムアミド、アクリロニトリル等を挙げることができるが、必ずしもこれらに限定されるものではない。
これらの重合性化合物は、１種を単独で、または必要に応じて任意の比率で２種以上混合して用いることができる。
<Polymerizable monomer>
The polymerizable monomer used in the present invention includes a monomer or an oligomer which is cured by ultraviolet light or heat to form a resin, and these can be used alone or in combination of two or more.
As the polymerizable monomer, for example, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, β-carboxyethyl (Meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, glycerin di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, Neopentyl glycol modified trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra ( Ta) Acrylate, 1,6-Hexanediol diglycidyl ether di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate Caprolactone-modified dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, ester acrylate, (meth) acrylic acid ester of methylolated melamine, various acrylic acid esters such as epoxy (meth) acrylate, urethane acrylate, Methacrylic acid ester, (meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaeryth Examples include, but are not necessarily limited to, lithol trivinyl ether, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N-vinylformamide, acrylonitrile and the like.
These polymerizable compounds can be used alone or in combination of two or more at an arbitrary ratio as needed.
本発明の組成物が含んでもよい熱感応性物質としては、熱重合開始剤としては、有機過酸化物系開始剤、アゾ系開始剤等を挙げることができる。
本発明の組成物が含んでもよい光感応性物質としては、光重合開始剤、光酸発生剤、光塩基発生剤があげられる。光感応性物質は、１種を単独で、または必要に応じて任意の比率で２種以上混合して用いることができる。
As a heat sensitive material which the composition of this invention may contain, an organic peroxide type initiator, an azo type initiator, etc. can be mentioned as a thermal polymerization initiator.
Examples of the photosensitive substance that may be contained in the composition of the present invention include a photopolymerization initiator, a photoacid generator, and a photobase generator. The photosensitive substance can be used alone or in combination of two or more at an arbitrary ratio as required.
光重合開始剤としては、アセトフェノン系化合物、ベンゾイン系化合物、ベンゾフェノン系化合物、チオキサントン系化合物、トリアジン系化合物、オキシムエステル系化合物、ホスフィン系化合物、キノン系化合物、ボレート系化合物； カルバゾール系化合物；イミダゾール系化合物；あるいは、チタノセン系化合物等が用いられる。
光酸発生剤としては、スルホニウム塩、テトラヒドロチオフェニウム塩、 Ｎ−スルホニルオキシイミド化合物などが挙げられる。
As the photopolymerization initiator, acetophenone compounds, benzoin compounds, benzophenone compounds, thioxanthone compounds, triazine compounds, oxime ester compounds, phosphine compounds, quinone compounds, borate compounds; carbazole compounds; imidazole compounds Compounds; or titanocene compounds and the like are used.
As a photo-acid generator, a sulfonium salt, a tetrahydro thiophenium salt, N- sulfonyl oxyimide compound etc. are mentioned.
光重合開始剤および／または光酸発生剤は光硬化性接着剤に含まれる樹脂成分（本発明の飽和脂環式エポキシエステル化合物、および、必要に応じて含まれる他の活性エネルギー重合性化合物から構成される樹脂成分）１００部に対して、０．０１部〜２０部であることが好ましい。０．０１部未満であると硬化が不十分であり、２０部より多い場合、光酸発生剤由来の着色や他の諸物性の低下を招く。 The photopolymerization initiator and / or the photoacid generator may be selected from the resin component contained in the photocurable adhesive (the saturated alicyclic epoxy ester compound of the present invention and the other active energy polymerizable compound optionally contained) It is preferable that it is 0.01 part-20 parts with respect to 100 parts of resin components comprised. If the amount is less than 0.01 part, curing is insufficient, and if it is more than 20 parts, coloring due to the photoacid generator and deterioration of other various physical properties are caused.
光塩基発生剤としては、複素環基含有光塩基発生剤、２−ニトロベンジルシクロヘキシルカルバメート、［［（２，６−ジニトロベンジル）オキシ］カルボニル］シクロヘキシルアミン、ビス［［（２−ニトロベンジル）オキシ］カルボニル］ヘキサン−１，６−ジアミン、トリフェニルメタノール、ｏ−カルバモイルヒドロキシルアミド、ｏ−カルバモイルオキシム、ヘキサアンミンコバルト（ＩＩＩ）トリス（トリフェニルメチルボレート）などが挙げられる。 As a photobase generator, a heterocyclic group-containing photobase generator, 2-nitrobenzyl cyclohexylcarbamate, [[(2,6-dinitrobenzyl) oxy] carbonyl] cyclohexylamine, bis [[(2-nitrobenzyl) oxy] And the like] carbonyl] hexane-1, 6-diamine, triphenylmethanol, o-carbamoyl hydroxylamide, o-carbamoyl oxime, hexaamminecobalt (III) tris (triphenyl methyl borate) and the like.
＜増感剤＞
さらに、本発明の組成物には、増感剤を含有させることができる。
増感剤としては、カルコン誘導体、ジベンザルアセトン等に代表される不飽和ケトン類、ベンジルやカンファーキノン等に代表される１，２−ジケトン誘導体、ベンゾイン誘導体、フルオレン誘導体、ナフトキノン誘導体、アントラキノン誘導体、キサンテン誘導体、チオキサンテン誘導体、キサントン誘導体、チオキサントン誘導体、クマリン誘導体、ケトクマリン誘導体、シアニン誘導体、メロシアニン誘導体、オキソノ−ル誘導体等のポリメチン色素、アクリジン誘導体、アジン誘導体、チアジン誘導体、オキサジン誘導体、インドリン誘導体、アズレン誘導体、アズレニウム誘導体、スクアリリウム誘導体、ポルフィリン誘導体、テトラフェニルポルフィリン誘導体、トリアリールメタン誘導体、テトラベンゾポルフィリン誘導体、テトラピラジノポルフィラジン誘導体、フタロシアニン誘導体、テトラアザポルフィラジン誘導体、テトラキノキサリロポルフィラジン誘導体、ナフタロシアニン誘導体、サブフタロシアニン誘導体、ピリリウム誘導体、チオピリリウム誘導体、テトラフィリン誘導体、アヌレン誘導体、スピロピラン誘導体、スピロオキサジン誘導体、チオスピロピラン誘導体、金属アレーン錯体、有機ルテニウム錯体、又はミヒラーケトン誘導体、α−アシロキシエステル、アシルフォスフィンオキサイド、メチルフェニルグリオキシレート、ベンジル、９，１０−フェナンスレンキノン、カンファーキノン、エチルアンスラキノン、４，４’−ジエチルイソフタロフェノン、３，３’，又は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、４，４’−ジエチルアミノベンゾフェノン等が挙げられる。
これらの増感剤は、１種を単独で、または必要に応じて任意の比率で２種以上混合して用いることができる。
<Sensitizer>
Furthermore, the composition of the present invention can contain a sensitizer.
As sensitizers, unsaturated ketones represented by chalcone derivatives, dibenzalacetone etc., 1,2-diketone derivatives represented by benzyl and camphorquinone etc., benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, polymethine dyes such as oxonol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, Trapyrazino porphyrazine derivative, phthalocyanine derivative, tetraazaporphyrazine derivative, tetraquinoxalylo porphyrazine derivative, naphthalocyanine derivative, subphthalocyanine derivative, pyrylium derivative, thiopyrilium derivative, tetraphyrin derivative, anurene derivative, spiropyran derivative, spirooxazine Derivative, thiospiropyran derivative, metal arene complex, organic ruthenium complex, or Michler's ketone derivative, α-acyloxy ester, acyl phosphine oxide, methylphenyl glyoxylate, benzyl, 9, 10-phenanthrenequinone, camphorquinone, ethyl Anthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, or 4,4′-tetra (t-butylperoxycarbonyl) benzopheno And 4,4'-diethylaminobenzophenone and the like.
These sensitizers can be used alone or in combination of two or more at an arbitrary ratio as required.
＜樹脂溶液１の調製＞
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けた反応容器にキシレン７０．０部を仕込み、８０℃に昇温し、反応容器内を窒素置換した後、滴下管よりｎ−ブチルメタクリレート１８．０部、メタクリル酸メチル１２．０部、２，２’−アゾビスイソブチロニトリル０．４部の混合物を２時間かけて滴下した。滴下終了後、更に３時間反応を継続し、重量平均分子量（Ｍｗ）２６０００のアクリル樹脂の溶液を得た。室温まで冷却した後、樹脂溶液約２ｇをサンプリングして１８０℃、２０分加熱乾燥して不揮発分を測定し、先に合成した樹脂溶液に不揮発分が２０重量％になるようにキシレンを添加してアクリル樹脂溶液１を調製した。
Preparation of Resin Solution 1
70.0 parts of xylene is charged into a reaction vessel in which a thermometer, a cooling pipe, a nitrogen gas introduction pipe, and a stirrer are attached to a separable four-necked flask, the temperature is raised to 80 ° C., the inside of the reaction vessel is purged with nitrogen, and then a dropping pipe A mixture of 18.0 parts of n-butyl methacrylate, 12.0 parts of methyl methacrylate and 0.4 parts of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a solution of an acrylic resin having a weight average molecular weight (Mw) of 26000. After cooling to room temperature, approximately 2 g of the resin solution is sampled, dried by heating at 180 ° C. for 20 minutes, non-volatile content is measured, and xylene is added to the resin solution synthesized above so that the non-volatile content is 20% by weight. Thus, an acrylic resin solution 1 was prepared.
＜樹脂溶液２の調製＞
セパラブル４口フラスコに温度計、冷却管、窒素ガス導入管、撹拌装置を取り付けた反応容器にキシレン７０．０部を仕込み、８０℃に昇温し、反応容器内を窒素置換した後、滴下管よりｎ−ブチルメタクリレート１４．０部、メタクリル酸メチル１０．０部、スチレン６．０部、２，２’−アゾビスイソブチロニトリル０．４部の混合物を２時間かけて滴下した。滴下終了後、更に３時間反応を継続し、重量平均分子量（Ｍｗ）２６０００のアクリル樹脂の溶液を得た。室温まで冷却した後、樹脂溶液約２ｇをサンプリングして１８０℃、２０分加熱乾燥して不揮発分を測定し、先に合成した樹脂溶液に不揮発分が２０重量％になるようにキシレンを添加してアクリル樹脂溶液２を調製した。
<Preparation of Resin Solution 2>
70.0 parts of xylene is charged into a reaction vessel in which a thermometer, a cooling pipe, a nitrogen gas introduction pipe, and a stirrer are attached to a separable four-necked flask, the temperature is raised to 80 ° C., the inside of the reaction vessel is purged with nitrogen, and then a dropping pipe A mixture of 14.0 parts of n-butyl methacrylate, 10.0 parts of methyl methacrylate, 6.0 parts of styrene, and 0.4 parts of 2,2'-azobisisobutyronitrile was dropped over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a solution of an acrylic resin having a weight average molecular weight (Mw) of 26000. After cooling to room temperature, approximately 2 g of the resin solution is sampled, dried by heating at 180 ° C. for 20 minutes, non-volatile content is measured, and xylene is added to the resin solution synthesized above so that the non-volatile content is 20% by weight. Thus, an acrylic resin solution 2 was prepared.
＜樹脂溶液３の調製＞
ブチラール樹脂エスレックBL-S（積水化学製）をNV１０％となるようにトルエンに溶解した。
Preparation of Resin Solution 3
Butyral resin SLEC BL-S (manufactured by Sekisui Chemical Co., Ltd.) was dissolved in toluene so as to have an NV of 10%.
＜樹脂溶液４の調製＞
ノルボルネン２００部、シクロペンテン５０部、１−ヘキセン１８０部およびトルエン７５０部を、窒素置換した反応容器に仕込み、６０℃に加熱した。これに、トリエチルアルミニウム（１．５モル／ｌ）のトルエン溶液０．６２部、ｔｅｒｔ−Ｃ４Ｈ５ＯＨ／ＣＨ３ＯＨで変性（ｔｅｒｔ−Ｃ４Ｈ９ＯＨ／ＣＨ３ＯＨ／Ｗ＝０．３５／０．３／１；モル比）したＷＣｌ６溶液（濃度０．０５モル／ｌ）３．７部を加え、８０℃で３時間加熱攪拌して、開環重合反応、水素添加反応を行い、次いでトリメチルベンゼンを用いてNVを１０％に調製して樹脂溶液4を得た。
<Preparation of Resin Solution 4>
200 parts of norbornene, 50 parts of cyclopentene, 180 parts of 1-hexene and 750 parts of toluene were charged in a nitrogen-purged reaction vessel and heated to 60.degree. In this, 0.62 parts of a toluene solution of triethylaluminum (1.5 mol / l) and modified with tert-C 4 H 5 OH / CH 3 OH (tert-C 4 H 9 OH / CH 3 OH / W = 0 .35 / 0.3 / 1; molar ratio) 3.7 parts of WCl 6 solution (concentration 0.05 mol / l) is added, and the mixture is heated and stirred at 80 ° C. for 3 hours for ring-opening polymerization reaction, hydrogenation reaction And then adjust the NV to 10% using trimethylbenzene to obtain a resin solution 4.
［比較例１］
（量子ドット０の合成）
無水酢酸亜鉛０．５５部、ドデカンチオール７．０部、オレイルアミン５．０部を加熱溶解し添加液を作成した。
塩化インジウム０．２２部、オクチルアミン８．２５部を反応容器に入れ、窒素バブリングを行いながら、１６５℃に加熱した。塩化インジウムが溶解した後、ジエチルアミノホスフィン０．８６部を短時間で注入し、２０分間１６５℃に制御した。その後、急冷し、４０℃に冷却した。上記添加液を注入し、２４０℃２時間加熱した後に、室温まで放冷した。放冷後、ヘキサンとエタノールを用いて再沈殿法で精製を行った。トルエンを用いて、固形分濃度１０％に調製し、ドデカンチオールで表面処理された量子ドットを含む比較分散液１を得た。
Comparative Example 1
(Composition of quantum dot 0)
An additive solution was prepared by heating and dissolving 0.55 parts of anhydrous zinc acetate, 7.0 parts of dodecanethiol and 5.0 parts of oleylamine.
0.22 parts of indium chloride and 8.25 parts of octylamine were charged in a reaction vessel and heated to 165 ° C. while nitrogen bubbling was performed. After the indium chloride was dissolved, 0.86 parts of diethylaminophosphine was injected in a short time and controlled at 165 ° C. for 20 minutes. It was then quenched and cooled to 40.degree. The above addition solution was injected, heated at 240 ° C. for 2 hours, and allowed to cool to room temperature. After leaving to cool, purification was performed by reprecipitation using hexane and ethanol. Comparative dispersion 1 containing a quantum dot which was prepared to a solid concentration of 10% and surface-treated with dodecanethiol was obtained using toluene.
［実施例１］
（量子ドット１の合成）
量子ドット０を、トルエンを用いて固形分濃度１％に希釈した。同量の５％処理剤１のトルエン溶液を添加し、１２時間撹拌した。トルエンとエタノールを用いて再沈殿法で精製を行った。トルエンを用いて、固形分濃度１０％に調製し、処理剤１で表面処理された量子ドット１を含有する分散液（組成物）を得た。
Example 1
(Composition of quantum dot 1)
Quantum dot 0 was diluted to a solid concentration of 1% with toluene. The same amount of 5% treatment agent 1 in toluene was added and stirred for 12 hours. Purification was performed by reprecipitation using toluene and ethanol. The solid content concentration was adjusted to 10% using toluene, and a dispersion (composition) containing the quantum dots 1 surface-treated with the treating agent 1 was obtained.
［実施例２〜８］
（量子ドット２〜８）
同様に処理剤を表１記載の処理剤に変更して、量子ドット希釈溶媒とエタノールを用いて精製することにより、表１の処理剤で表面処理された量子ドット２〜８の１０％分散液（組成物）を合成した。
[Examples 2 to 8]
(Quantum dots 2 to 8)
Similarly, 10% dispersion liquid of quantum dots 2 to 8 surface-treated with the treating agent of Table 1 by changing the treating agent to the treating agent described in Table 1 and purifying it using a quantum dot dilution solvent and ethanol. (Composition) was synthesized.
＜組成物評価方法＞
以下の評価方法によって得られた評価結果を表２に示す。
（自然乾燥法）
直径１２ｍｍ基板丸カバーガラス（松浪ガラス工業製）の上に、１０％分散液（組成物）の２０μＬを静かに載せて、その後６時間の間、自然乾燥した。
（ＱＹ維持率）
QY（量子収率）維持率は印刷初期のQYを１として、２週間後の比率を示した。１に近い方が好ましいが、0.6以上であれば実用上使用可能である。
<Composition evaluation method>
The evaluation results obtained by the following evaluation methods are shown in Table 2.
(Natural drying method)
20 μL of a 10% dispersion (composition) was gently placed on a 12 mm substrate round cover glass (manufactured by Matsunami Glass Industry Co., Ltd.), and then naturally dried for 6 hours.
(QY maintenance rate)
The QY (quantum yield) retention rate is a ratio of two weeks after setting QY at the initial stage of printing to 1. Although it is preferable to be close to 1, if it is 0.6 or more, it can be practically used.
（量子収率測定）
測定機 絶対ＰＬ量子収率測定装置Ｃ９９２０−０２
励起波長 ４００ｎｍ積分範囲 ３７５〜４２５ｎｍ
蛍光積分範囲 ４３０〜８００ｎｍ
(Quantum yield measurement)
Measuring machine Absolute PL quantum yield measuring device C9920-02
Excitation wavelength 400 nm integration range 375-425 nm
Fluorescence integration range 430-800 nm
本発明の処理剤を使用すると、ＱＹの経時低下を抑制できることが示された。 It has been shown that the use of the treatment agent of the present invention can suppress the decrease in QY with time.
＜インクジェットインキの作成＞
（実施例９〜１６、比較例１〜４）
表３に示したインキ組成にて、密閉できる容器に、量子ドット溶液、樹脂溶液、溶剤、重合性単量体、感応性物質の順番で計量し、その後、密閉して、３分間、浸透してインクジェットインキを作成した。
<Creation of inkjet ink>
(Examples 9 to 16, Comparative Examples 1 to 4)
With the ink composition shown in Table 3, measure the quantum dot solution, resin solution, solvent, polymerizable monomer, sensitive substance in this order in a sealable container, and then seal and penetrate for 3 minutes. Ink jet ink was prepared.
ＤＢＣＡ：ジエチレングリコールモノブチルエーテルアセテート
ＰＧＭＡｃ：プロピレングリコールメチルエーテルアセテート
DBCA: diethylene glycol monobutyl ether acetate PGMAc: propylene glycol methyl ether acetate
＜インクジェットインキ評価方法＞
以下の評価方法によって得られた評価結果を表４に示す。
（粘度測定）
２５℃にて、振動式粘度計ビスコメイトＶＭ−１０Ａ−Ｌ（SEKONIC社製）を用いて、測定した。
<Inkjet ink evaluation method>
The evaluation results obtained by the following evaluation methods are shown in Table 4.
(Viscosity measurement)
It measured at 25 degreeC using vibration-type viscometer Viscomate VM-10A-L (made by SEKONIC).
下記のインクジェット吐出条件で、インクジェット印刷を行い、ＩＪ印刷継続可能時間、ＩＪ印刷再印刷性試験を行った。
（ＩＪ印刷 継続可能時間）
印刷ができない場合を×、印刷を３０以上継続できない場合を△、３０分以上継続できた場合を〇とした。実用上、３０分以上継続して印刷できることが必要である。
（ＩＪ印刷 再印刷性）
ＩＪ吐出後１時間印刷を中止して、再印刷を行った。その際、そのまま印刷できた場合を◎、ヘッド吐出部を、溶剤を含んだ綿棒で掃除すれば印刷できた場合を〇、掃除しても印刷できない場合を×とした。実用上、◎、〇であることが必要である。
・インクジェット吐出試験条件
印刷機ＤｉｍａｔｉｘＭａｔｅｒｉａｌｓＰｒｉｎｔｅｒ
カートリッジ１０ＤｉｍａｔｉｘＭａｔｅｒｉａｌｓＣａｒｔｒｉｇｅｓ、１０ｐＬ
印刷パターン１ｍｍ間隔の格子模様
基板丸カバーガラス・松浪ガラス工業製
基板温度３０℃
印刷後乾燥４０℃２０分
The ink jet printing was performed under the following ink jet discharge conditions, and the IJ printing continued printability test was performed for the IJ printable continuation time.
(IJ printing can be continued)
The case where printing can not be performed is x, the case where printing can not be continued for 30 or more is Δ, and the case where it can be continued for 30 minutes or more is o. Practically, it is necessary to be able to print continuously for 30 minutes or more.
(IJ printing reprintability)
Printing was stopped for 1 hour after IJ ejection, and reprinting was performed. At that time, the case where printing could be carried out as it was ◎, the case where the printing was possible if the head discharge part was cleaned with a cotton swab containing a solvent was made 〇, and the case where printing could not be carried out even after cleaning was made x. For practical use, ◎ and 〇 are required.
・ Ink jet discharge test condition printing machine DimatixMaterialsPrinter
Cartridge 10DimatixMaterialsCartriges, 10pL
Printed pattern 1 mm interval grid pattern substrate round cover glass · made by Matsunami Glass Industrial substrate temperature 30 ° C
Drying after printing 40 ° C 20 minutes
（ＱＹ維持率）
QY維持率は印刷初期のQYを１として、２週間後の比率を示した。１に近い方が好ましいが、0.6以上であれば実用上使用可能である。
(QY maintenance rate)
The QY maintenance rate is 2 weeks after setting QY at the initial stage of printing to 1. Although it is preferable to be close to 1, if it is 0.6 or more, it can be practically used.
（量子収率測定）
測定機 絶対ＰＬ量子収率測定装置Ｃ９９２０−０２
励起波長 ４００ｎｍ積分範囲 ３７５〜４２５ｎｍ
蛍光積分範囲 ４３０〜８００ｎｍ
(Quantum yield measurement)
Measuring machine Absolute PL quantum yield measuring device C9920-02
Excitation wavelength 400 nm integration range 375-425 nm
Fluorescence integration range 430-800 nm
適切な粘度に調製することでＩＪ印刷を行うことができ、本発明の処理剤を用いると、ＱＹ維持率が高いことが証明された。
IJ printing can be performed by adjusting the viscosity to an appropriate viscosity, and it has been proved that the QY retention rate is high using the treatment agent of the present invention.
Claims (6)
一般式（1）
式中、Ｘ１、Ｘ２は各々独立に直接結合、−ＣＨ２−、−ＣＨ＜、−Ｏ−、を表し
Ｒ１、Ｒ２は水素原子または、置換基を有していてもよい芳香族残基を表す。ただし、Ｒ１、とＲ２が同時に水素原子になることはない。
ｎ１、ｎ２は各々独立に１または２を表す。 A quantum dot, characterized in that semiconductor fine particles are surface-treated with a treatment agent represented by the following general formula (1).
General formula (1)
In the formula, X 1 and X 2 each independently represent a direct bond, -CH 2- , -CH <, -O-, and R 1 and R 2 each represent a hydrogen atom or an aromatic group which may have a substituent. Represents a family residue. However, R 1 and R 2 can not simultaneously be hydrogen atoms.
n1 and n2 each independently represent 1 or 2.
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| JP2014505744A (en) * | 2010-12-02 | 2014-03-06 | インテマティックス・コーポレーション | Solid-state light emitting device and signage comprising photoluminescence wavelength conversion and photoluminescent composition therefor |
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| WO2022039179A1 (en) * | 2020-08-21 | 2022-02-24 | 国立大学法人山形大学 | Resin ink and electronic device |
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