JP5470058B2 - カラーフィルタ用着色組成物、カラーフィルタ、その製造方法、及びそれを具備する液晶表示装置並びに有機el表示装置 - Google Patents
カラーフィルタ用着色組成物、カラーフィルタ、その製造方法、及びそれを具備する液晶表示装置並びに有機el表示装置 Download PDFInfo
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- JP5470058B2 JP5470058B2 JP2010007130A JP2010007130A JP5470058B2 JP 5470058 B2 JP5470058 B2 JP 5470058B2 JP 2010007130 A JP2010007130 A JP 2010007130A JP 2010007130 A JP2010007130 A JP 2010007130A JP 5470058 B2 JP5470058 B2 JP 5470058B2
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- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- HTPJPKXFBLUBPI-UHFFFAOYSA-I pentasodium 5-[[4-[[4-anilino-6-[[8-hydroxy-7-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]diazenyl]-3,6-disulfonatonaphthalen-1-yl]amino]-1,3,5-triazin-2-yl]amino]phenyl]diazenyl]-2-hydroxybenzoate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].COc1cc(N=Nc2cc(cc3cc(cc(O)c23)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2c(Nc3nc(Nc4ccccc4)nc(Nc4ccc(cc4)N=Nc4ccc(O)c(c4)C([O-])=O)n3)cc(cc2cc1S([O-])(=O)=O)S([O-])(=O)=O HTPJPKXFBLUBPI-UHFFFAOYSA-I 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 125000005412 pyrazyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000011163 secondary particle Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- QTTDXDAWQMDLOF-UHFFFAOYSA-J tetrasodium 3-[[4-[[4-[(6-amino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-6-sulfonatonaphthalen-1-yl]diazenyl]naphthalen-1-yl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].Nc1ccc2c(O)c(N=Nc3ccc(N=Nc4ccc(N=Nc5cc(c6cccc(c6c5)S([O-])(=O)=O)S([O-])(=O)=O)c5ccccc45)c4ccc(cc34)S([O-])(=O)=O)c(cc2c1)S([O-])(=O)=O QTTDXDAWQMDLOF-UHFFFAOYSA-J 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- UGCDBQWJXSAYIL-UHFFFAOYSA-N vat blue 6 Chemical compound O=C1C2=CC=CC=C2C(=O)C(C=C2Cl)=C1C1=C2NC2=C(C(=O)C=3C(=CC=CC=3)C3=O)C3=CC(Cl)=C2N1 UGCDBQWJXSAYIL-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- KOTVVDDZWMCZBT-UHFFFAOYSA-N vat violet 1 Chemical compound C1=CC=C[C]2C(=O)C(C=CC3=C4C=C(C=5C=6C(C([C]7C=CC=CC7=5)=O)=CC=C5C4=6)Cl)=C4C3=C5C=C(Cl)C4=C21 KOTVVDDZWMCZBT-UHFFFAOYSA-N 0.000 description 1
- GFFQNEGBFFGLQG-UHFFFAOYSA-N vat yellow 2 Chemical compound S1C2=C3C(=O)C4=CC=C5N=C(C=6C=CC=CC=6)SC5=C4C(=O)C3=CC=C2N=C1C1=CC=CC=C1 GFFQNEGBFFGLQG-UHFFFAOYSA-N 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940074411 xylene Drugs 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
Images
Landscapes
- Liquid Crystal (AREA)
- Electroluminescent Light Sources (AREA)
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
Description
[製造例1]
下記式(2)のアゾ染料3部、酸化マグネシウム1部、水20部を仕込み、常温で、1時間攪拌した。これに硫酸ジメチル0.5部を加え、50℃で3時間反応させた。反応液に水50部、濃硫酸1部を加え、60℃で1時間攪拌した。引き続いて、DMF10部にトリストリフルオロメタンスルホニウムメチドのセシウム塩3部を溶解させた溶液を滴下し、3時間攪拌した。析出した結晶をろ取、水洗、乾燥し、下記式(3)の黄色染料(DY−1)2部を得た。
[製造例2]
以下に、実施例及び比較例で用いたアクリル樹脂溶液の調製について説明する。樹脂の分子量は、GPC(ゲルパーミエーションクロマトグラフィ)により測定したポリスチレン換算の質量平均分子量である。
赤色用顔料:C.I.Pigment Red 254(チバ・スペシャルティ・ケミカルズ社製「イルガーフォーレッド B−CF」)、およびC.I.Pigment Red 177(チバ・スペシャルティ・ケミカルズ社製「クロモフタールレッド A2B」)
黄色顔料:C.I.Pigment Yellow 150 (バイエル社製「ファンチョンファーストイエロー Y−5688」;Y−1)、およびC.I.Pignment Yellow139 (BASF社製[PALIOTOL Yellow D1819];Y−2)
緑色用顔料:C.I.Pigment Green 58(大日本インキ化学工業(株)「Phthalocyanine Green A110」;G−1)
青色用顔料:C.I.Pigment Blue 15:6(東洋インキ製造(株)製「リオノールブルーES」)
[製造例3]
ジケトピロロピロール系赤色顔料PR254(チバスペシャリティケミカルズ社製「イルガフォアレッドB‐CF」)100部、色素誘導体(D−1)10部、粉砕した食塩1000部、およびジエチレングリコール120部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、60℃で10時間混練した。この混合物を温水2000部に投入し、約80℃に加熱しながらハイスピードミキサーで約1時間攪拌してスラリー状とし、濾過、水洗をくりかえして食塩および溶剤を除いた後、80℃で24時間乾燥し、微細化顔料(R−1)を得た。得られた顔料の平均粒子径は25nmであった。
アントラキノン系赤色顔料PR177(チバスペシャリティケミカルズ社製「クロモフタルレッドA2B」)100部、色素誘導体(D-2)8部、粉砕した食塩700部、およびジエチレングリコール180部をステンレス製1ガロンニーダー(井上製作所製)に仕込み、70℃で4時間混練した。この混合物を温水4000部に投入し、約80℃に加熱しながらハイスピードミキサーで約1時間攪拌してスラリー状とし、濾過、水洗をくりかえして食塩および溶剤を除いた後、80℃で24時間乾燥し、微細化顔料(R-2)を得た。得られた顔料の平均一次粒子径は30nmであった。
青色顔料(C.I.PigmentBlue15:6、東洋インキ製造(株)製「LIONOLBLUEES」)200部、塩化ナトリウム1600部、およびジエチレングリコール(東京化成社製)100部をステンレス製1ガロンニーダー(井上製作所社製)に仕込み、70℃で12時間混練した。次に、この混合物を約5リットルの温水に投入し、約70℃に加熱しながらハイスピードミキサーで約1時間撹拌してスラリー状とした後、濾過し、水洗して塩化ナトリウム及びジエチレングリコールを除き、80℃で24時間乾燥し、198部のソルトミリング処理顔料(青色顔料B−1)を得た。
下記表1に示す組成の混合物を均一に撹拌混合した後、直径0.1mmのジルコニアビーズを用いて、アイガーミルで2時間分散した後、5μmのフィルタで濾過し、顔料分散体を作製した。なお、色素誘導体D−1からD−4の構造を下記表2に記載する。
[実施例1]
下記組成の混合物を均一になるように攪拌混合した後、5μmのフィルターで濾過して着色組成物RR−1を得た。
顔料分散体(PR−2) 22.3質量部
バインダー樹脂(P) 27.0質量部
トリメチロールプロパントリアクリレート 3.4質量部
(東亞合成株式会社製 「アロニックス M402」)
光重合開始剤 0.8質量部
(チバガイギー社製「イルガキュア−OXE02」)
有機溶剤(PGMAc) 44.8質量部
[実施例2乃至6、比較例1乃至6]
染料、顔料分散体に下記表3に記載の染料、顔料分散体を用いた以外は、実施例1と同様にして着色組成物を得た。なお、下記表3では、実施例1に係る着色組成物も併せて示した。
下記組成の混合物を均一になるように攪拌混合した後、5μmのフィルターで濾過して青色着色組成物RB−1を得た。
バインダー樹脂(P) 11.5質量部
トリメチロールプロパントリアクリレート 4.5質量部
(東亞合成株式会社製 「アロニックス M402」)
光重合開始剤 2.3質量部
(チバガイギー社製「イルガキュア−907」)
有機溶剤(PGMAc) 55.7質量部
[色度]
実施例1乃至実施例6、比較例1乃至比較例6、及び製造例6の着色組成物を、硬化後の膜厚が1.8μmとなるように、スピンコート法によりガラス基板に塗布し、乾燥した後、超高圧水銀ランプを用いて紫外線で露光した。その後、この基板を200℃で20分間熱処理して着色膜を得た。
着色膜のコントラスト比を以下に示す方法で測定した。即ち、図4(a)に示すように、試料34の前後に、偏光板32,33を、その偏光軸を互いに平行にして配置した。一方の偏光板33の側からバックライト36を照射して、他方の偏光板32を透過した光37の輝度Lp(平行透過光の輝度)を色彩輝度計BM−5A(トプコン(株)製)31を使用して、2°の視野の条件で測定した(CIE1931表色系)。
[実施例7]
まず、赤色着色組成物としてRR−2をスピンコート法により、予めブラックマトリックスが形成されてあるガラス基板に塗工した後、クリーンオーブン中で、70℃で20分間プリベークした。次いで、この基板を室温に冷却した後、超高圧水銀ランプを用い、フォトマスクを介して紫外線を露光した。その後、この基板を23℃の炭酸ナトリウム水溶液を用いてスプレー現像した後、イオン交換水で洗浄し、風乾した。さらに、クリーンオーブン中で、230℃で30分間ポストベークを行い、基板上にストライプ状の赤色フィルタセグメントを形成した。
着色組成物として、下記表5に示すものを使用したことを除いて、実施例7と同様に実施例8並びに実施例9及び比較例7乃至比較例9のカラーフィルタを得た。これらのカラーフィルタのコントラスト比を同様に測定し、得られた値を下記表5に示す。なお、実施例7についても下記表5に合せて記載した。
[実施例10]
カラーフィルタとしてCF−1を使用し、該カラーフィルタの上に透明ITO電極層を形成し、更にその上にポリイミド配向層を形成した。このガラス基板の他方の表面に偏光板を形成した。他方、別の(第2の)ガラス基板の一方の表面にTFTアレイおよび画素電極を形成し、他方の表面に偏光板を形成した。
[色再現領域とコントラスト比の評価]
作製した液晶表示装置のNTSC比(アメリカNational Television System Committee(NTSC)により定められた標準方式の3原色、赤(0.67, 0.33)、緑(0.21, 0.71)、青(0.14, 0.08)により囲まれる面積に対する比率)で定められたRGB3色の三角形の面積を100として、基準値の面積に対する三角形或いは四角形の面積の比率を測定した。また、全白表示の時の輝度Lwと全黒表示の時の輝度Lbを測定し、Lw/Lbを液晶パネルのコントラスト比として計算した。以上の結果を下記表6に示す。
Claims (10)
- 着色材料としてさらに少なくとも1種の顔料を含むことを特徴とする請求項1に記載のカラーフィルタ用着色組成物。
- 前記顔料として少なくとも、C.I.PigmentYellow 138、139、150、185から選ばれる1種の黄色顔料を含むことを特徴とする請求項2に記載のカラーフィルタ用黄色着色組成物。
- 前記顔料として少なくとも、C.I.PigmentGreen7、36、58から選ばれる少なくとも1種の緑色顔料を含むことを特徴とする請求項2に記載のカラーフィルタ用緑色着色組成物。
- 前記顔料として少なくとも、C.I.PigmentRed177、242、254から選ばれる少なくとも1種の赤色顔料を含むことを特徴とする請求項2に記載のカラーフィルタ用赤色着色組成物。
- 少なくとも1種の光重合開始剤、及び少なくとも1種の重合性化合物を含有することを特徴とする請求項1乃至請求項5のいずれかに記載のカラーフィルタ用着色感光性組成物。
- 請求項1乃至請求項6のいずれかに記載の着色組成物を硬化してなる着色画素を備えることを特徴とするカラーフィルタ。
- 請求項1乃至請求項6のいずれかに記載の着色組成物を透明基板上に塗布し、硬化して着色画素を形成することを特徴とするカラーフィルタの製造方法。
- 請求項7に記載のカラーフィルタを具備することを特徴とする液晶表示装置。
- 請求項7に記載のカラーフィルタを具備することを特徴とする有機EL表示装置。
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