JP2014144931A - ベンゾトリアゾール誘導体化合物 - Google Patents
ベンゾトリアゾール誘導体化合物 Download PDFInfo
- Publication number
- JP2014144931A JP2014144931A JP2013014828A JP2013014828A JP2014144931A JP 2014144931 A JP2014144931 A JP 2014144931A JP 2013014828 A JP2013014828 A JP 2013014828A JP 2013014828 A JP2013014828 A JP 2013014828A JP 2014144931 A JP2014144931 A JP 2014144931A
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- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- benzotriazole
- compound
- fluorescent dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 Benzotriazole derivative compound Chemical class 0.000 title claims abstract description 70
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 41
- 239000000463 material Substances 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000005157 alkyl carboxy group Chemical group 0.000 claims abstract description 7
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 25
- 239000011347 resin Substances 0.000 claims description 25
- 239000011342 resin composition Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
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- 229920000573 polyethylene Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
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- 238000004528 spin coating Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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Abstract
【解決手段】下記一般式で示されるベンゾトリアゾール誘導体化合物とする。
式中R1は、Hまたはアルキル基、R2はアルキル基を表す。R3及びR4は水素原子、ハロゲン原子、アルキル基、アルコキシ基、ヒドロキシル基、アミノ基、モノ置換アミノ基、ジ置換アミノ基、ニトロ基、カルボキシル基、アルキルオキシカルボニル基、アルキルカルボキシル基、アルキルカルボキシエステル基、アリール基、アシル基、スルホ基又はシアノ基を表すが、少なくともいずれかはアルコキシ基を表す。
【選択図】なし
Description
一般式(1)
[式中R1は、水素原子又は炭素数1〜8のアルキル基を表し、R2は炭素数1〜8のアルキル基を表す。R3及びR4はそれぞれ独立して、水素原子、ハロゲン原子、炭素数1〜8のアルキル基、炭素数1〜8のアルコキシ基、ヒドロキシル基、アミノ基、炭素数1〜4の直鎖または分鎖のモノ置換アミノ基、炭素数1〜4の直鎖または分鎖のジ置換アミノ基、ニトロ基、カルボキシル基、炭素数1〜8のアルキルオキシカルボニル基、炭素数1〜3のアルキルカルボキシル基、炭素数1〜8のアルキルカルボキシエステル基、アリール基、アシル基、スルホ基又はシアノ基を表すが、少なくともいずれかは炭素数1〜8のアルコキシ基を表す。]
下記(化2〜化4)の−R5COOHで表されるアルキルカルボキシル基; 下記(化5〜化14)の−R6COOR7で表されるアルキルカルボキシエステル基;フェニル基、ベンジル基、トリル基、キシリル基等のアリール基;ホルミル基、アセチル基、プロピオニル基、ブチリル基、ベンゾイル基等のアシル基;スルホ基;シアノ基が挙げられるが、少なくともいずれかはアルコキシ基である。
有機蛍光色素は樹脂中に添加されて使用されることが多く、本発明のベンゾトリアゾール誘導体化合物を有機蛍光色素として使用する場合も同様に樹脂中に添加して蛍光性樹脂組成物として用いられる。本発明のベンゾトリアゾール誘導体化合物を配合可能な樹脂として具体的は、ポリエチレン、ポリプロピレン、ポリブテン、ポリペンテン、ポリ-3−メチルブチレン、ポリメチルペンテンなどのα−オレフィン重合体またはエチレン−酢酸ビニル共重合体、エチレン−プロピレン共重合体などのポリオレフィン、ポリ塩化ビニル、ポリ臭化ビニル、ポリフッ化ビニル、塩素化ポリエチレン、塩素化ポリプロピレン、臭素化ポリエチレン、塩化ゴム、塩化ビニル−酢酸ビニル共重合体、塩化ビニル−エチレン共重合体、塩化ビニル−プロピレン共重合体、塩化ビニル−スチレン共重合体、塩化ビニル−イソブチレン共重合体、塩化ビニル−塩化ビニリデン共重合体、塩化ビニル−スチレン−無水マレイン酸三元共重合体、塩化ビニル−スチレン−アクリロニトリル三元共重合体、塩化ビニル−ブタジエン共重合体、塩化ビニル−イソブチレン共重合体、塩化ビニル−塩素化プロピレン共重合体、塩化ビニル−塩化ビニリデン−酢酸ビニル三元共重合体、塩化ビニル−アクリル酸エステル共重合体、塩化ビニル−マレイン酸エステル共重合体、塩化ビニル−メタクリル酸エステル共重合体、塩化ビニル−アクリロニトリル共重合体、内部可塑性ポリ塩化ビニルなどの含ハロゲン合成樹脂、石油樹脂、クマロン樹脂、ポリスチレン、スチレンと他の単量体(無水マレイン酸、ブタジエン、アクリロニトリルなど)との共重合体、アクリロニトリル−ブタジエン−スチレン樹脂、アクリル酸エステル−ブタジエン−スチレン樹脂、メタクリル酸エステル−ブタジエン−スチレン樹脂などのスチレン系樹脂、ポリ酢酸ビニル、ポリビニルアルコール、ポリビニルホルマール、ポリビニルブチラール、アクリル樹脂、メタクリレート樹脂、ポリアクリロニトリル、ポリフェニレンオキシド、ポリカーボネート、変性ポリフェニレンオキシド、ポリアセタール、フェノール樹脂、尿素樹脂、メラミン樹脂、エポキシ樹脂、シリコン樹脂、ポリエチレンテレフタレート、強化ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリスルホン系樹脂、ポリエーテルスルホン、ポリフェニレンスルフィド、ポリエーテルケトン、ポリエーテルイミド、ポリオキシベンゾイル、ポリイミド、ポリマレイミド、ポリアミドイミド、アルキド樹脂、アミノ樹脂、ビニル樹脂、水溶性樹脂、粉体塗料用樹脂、ポリアミド樹脂、ポリウレタン樹脂、不飽和ポリエステル樹脂を例示することができるが、これらに限定されるものではない。
本発明のベンゾトリアゾール誘導体化合物は、有機電界発光素子の発光材料として利用でき、発光層において、本発明のベンゾトリアゾール誘導体化合物のみ、あるいは他の化合物と組合せて使用できる。本発明のベンゾトリアゾール誘導体化合物以外の発光機能を有する化合物としては、例えば、ペリレン誘導体、クマリン誘導体、有機金属錯体、ピラン誘導体、スチルベン誘導体、アクリドン誘導体、オキサゾン誘導体、キナクリドン誘導体、ベンゾオキサゾール誘導体、ポリ−N−ビニルカルバゾール誘導体、ポリフルオレン誘導体、ポリフェニレンビニレン誘導体等、一般的な低分子蛍光材料、低分子リン光材料、ポリマー発光材料等が用いられる。これらの発光材料は、一種類のみを用いてもよく、また、二種類以上を適宜混合して用いてもよい。
<測定条件>
装置:L−2130((株)日立ハイテクノロジーズ製)
使用カラム:SUMIPAX ODS A−212 6.0×150mm 5μm
カラム温度:40℃
移動相: メタノール/水=95/5
流速:1.0ml/min
<測定結果>
HPLC面百純度:99.9%
なお、以下の実施例2も本実施例と同様の測定条件でHPLC測定を行った。
測定条件は次のとおりである。
<測定条件>
装置:JEOL ECX-400
共振周波数:400MHz(1H−NMR)
溶媒:クロロホルム−d
1H−NMRの内部標準物質として、テトラメチルシランを用い、ケミカルシフト値はδ値(ppm)、カップリング定数はHertzで示した。またsはsinglet、dはdoublet、tはtriplet、ddはdoublet doublet、mはmultipletの略とする。以下の実施例すべてにおいても同様である。
得られたNMRスペクトルの内容は以下のとおりである。なお、以下の実施例2及び4も本実施例と同様の測定条件でNMR測定を行った。
δ=8.83(s,1H,benzotriazol−H),8.13(d,1H,J=9.0Hz,benzotriazol−H),8.00(d,1H,J=9.2Hz,benzotriazol−H),7.67(s,2H,benzene−H),4.06(t,2H,benzene−O−CH2−H),4.01(s,6H,benzene−(O−CH3)2−H),1.79(dd,2H,J=7.6Hz,J=7.2Hz,J=7.2Hz,CH2−H),1.48(m,2H,CH2−H),1.31(m,8H,(CH2)4−H),0.89(t,3H,CH3−H)
δ=8.71(s,1H,benzotriazol−H),8.06(d,1H,J=9.0Hz,benzotriazol−H),7.95(d,1H,J=8.8Hz,benzotriazol−H),7.65(s,2H,benzene−H),4.05(t,2H,benzene−O−CH2−H),4.00(s,6H,benzene−(O−CH3)2−H),3.99(s,3H,CO−O−CH3−H),1.78(dd,2H,J=8.0Hz,J=7.2Hz,J=6.8Hz,CH2−H),1.48(t,2H,CH2−H),1.32(m,8H,(CH2)4−H),0.89(t,3H,CH3−H)
<測定条件>
装置:L−2130((株)日立ハイテクノロジーズ製)
使用カラム:SUMIPAX ODS A−212 6.0×150mm 5μm
カラム温度:40℃
移動相: メタノール/水=99/1
流速:1.0ml/min
<測定結果>
HPLC面百純度:99.0%
なお、以下の実施例4も本実施例と同様の測定条件でHPLC測定を行った。
測定条件は次のとおりである。
<測定条件>
装置:JEOL ECX-400
共振周波数:400MHz(1H−NMR)
溶媒:DMSO−d6
得られたNMRスペクトルの内容は以下のとおりである。
δ=8.61(s,1H,benzotriazol−H),8.10(dd,1H,J=8.4Hz,J=0.8Hz,J=0.8Hz,benzotriazol−H),8.00(dd,1H,J=7.6Hz,J=1.6Hz,J=1.2Hz,benzotriazol−H),7.88(d,1H,J=9.6,benzene−H),7.87(s,1H,benzene−H),7.21(d,1H,J=9.6Hz,benzene−H),4.06(t,2H,benzene−O−CH2−H),3.93(s,3H,−O−CH3−H),1.75(dd,2H,J=8.0Hz,J=6.8Hz,J=6.8Hz,CH2−H),1.43(m,2H,CH2−H),1.28(m,8H,(CH2)4−H),0.87(t,3H,CH3 −H)
δ=8.70(s,1H,benzotriazol−H),8.05(dd,1H,J=7.6Hz,J=1.6Hz,J=1.2Hz,benzotriazol−H),7.94(dd,1H,J=8.0Hz,J=0.8Hz,J=0.8Hz,benzotriazol−H),7.93(m,2H,benzene−H),7.01(d,1H,J=9.6Hz,benzene−H),4.10(t,2H,benzene−O−CH2−H),4.03(s,3H,CO−O−CH3−H),3.99(s,3H,benzene−O−CH3−H),1.90(t,2H,CH2−H),1.49(m,2H,CH2−H),1.33(m,8H,(CH2)4−H),0.89(t,3H,CH3−H)
実施例1〜4で得られた化合物(a)、(b)、(c)、(d)のクロロホルム中の吸収及び発光特性を表1に示す。
同じベンゾトリアゾール誘導体化合物であるが、一般式(1)と異なる構造である、化合物(e);2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール、化合物(f);メチル 2−(4−オクチルオキシフェニル)−2H−ベンゾトリアゾール−5−カルボキシレートについても、上記実施例1〜4と同様に吸収及び発光特性を表1に示す。また、従来の有機蛍光色素である化合物(g);4,4‘−ビス(2−メトキシスチリル)ビフェニル(東京化成工業(株)製)についても上記実施例1〜4と同様に吸収及び発光特性を表1に示す。
装置:UV−2450((株)島津製作所製)
測定波長:250〜 500nm
濃度:10ppm
セル:1cm石英
装置:FP−6600(日本分光(株)製)
測定波長:200〜 600nm
濃度:10ppm
セル:1cm石英
装置:C10027(浜松ホトニクス(株)製)
濃度:10ppm
セル:1cm石英
上記実施例2により得られた化合物(b)のポリメチルメタクリレート(以下、「PMMA」と記す。)フィルム中での吸収及び発光特性を、表2に示す。
PMMA:和光純薬工業(株)製 10mg
有機蛍光色素:0.5mg
トルエン:0.7ml
成膜法:スピンコート
膜厚:120nm
装置:UV−3600((株)島津製作所製)
測定波長:250〜 500nm
装置:FP−6600(日本分光(株)製)
測定波長:200〜 600nm
装置:C10027(浜松ホトニクス(株)製)
実施例2で得られた化合物(b)を用いて、下記の手順で湿式塗布型有機電界発光素子を作製した。
Claims (5)
- 下記の一般式(1)で表されることを特徴とするベンゾトリアゾール誘導体化合物。
[式中R1は、水素原子又は炭素数1〜8のアルキル基を表し、R2は炭素数1〜8のアルキル基を表す。R3及びR4はそれぞれ独立して、水素原子、ハロゲン原子、炭素数1〜8のアルキル基、炭素数1〜8のアルコキシ基、ヒドロキシル基、アミノ基、炭素数1〜4の直鎖または分鎖のモノ置換アミノ基、炭素数1〜4の直鎖または分鎖のジ置換アミノ基、ニトロ基、カルボキシル基、炭素数1〜8のアルキルオキシカルボニル基、炭素数1〜3のアルキルカルボキシル基、炭素数1〜8のアルキルカルボキシエステル基、アリール基、アシル基、スルホ基又はシアノ基を表すが、少なくともいずれかは炭素数1〜8のアルコキシ基を表す。] - 上記一般式(1)におけるR3及びR4がそれぞれ独立して水素原子又はメトキシ基を表すが、少なくともいずれかがメトキシ基である請求項1記載のベンゾトリアゾール誘導体化合物。
- 請求項1,2のいずれかの項に記載のベンゾトリアゾール誘導体化合物を含有する有機蛍光色素。
- 樹脂に、請求項3に記載の有機蛍光色素を配合した蛍光性樹脂組成物。
- 請求項3に記載の有機蛍光色素を含有する有機電界発光素子発光材料。
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