JP2017527849A - 共鳴エネルギ移動を示す高効率の分子 - Google Patents
共鳴エネルギ移動を示す高効率の分子 Download PDFInfo
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- JP2017527849A JP2017527849A JP2017510304A JP2017510304A JP2017527849A JP 2017527849 A JP2017527849 A JP 2017527849A JP 2017510304 A JP2017510304 A JP 2017510304A JP 2017510304 A JP2017510304 A JP 2017510304A JP 2017527849 A JP2017527849 A JP 2017527849A
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- light
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- luminescent material
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- 230000008569 process Effects 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 125000005550 pyrazinylene group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
○ここで、A、B、C、J、及びQの各々は、水素、フッ素、塩素、イソプロピル、t−ブチル、メトキシ、16までの炭素原子を有するアルキル、及び16までの炭素原子を有する酸素含有アルキルから選択される基を個別に含む。
−G2、G3、G4、及びG5は、水素、フッ素、塩素、イソプロピル、t−ブチル、メトキシ、16までの炭素原子を有するアルキル、及び16までの炭素原子を有する酸素含有アルキル、及びXから選択される基を個別に含む。
○ここで、D、E、I、L、及びMの各々は、水素、フッ素、塩素、イソプロピル、t−ブチル、メトキシ、16までの炭素原子を有するアルキル、及び16までの炭素原子を有する酸素含有アルキルから選択される基を個別に含む。
−更に、G2、G3、G4、及びG5から選択される少なくとも2つは少なくともXを含み、個別に、G2、G3、G4、及びG5から選択される前記少なくとも2つのうち少なくとも2つのD、E、I、L、及びMの少なくとも1つは、フッ素及び塩素から選択される基、特にフッ素を含む。
A:2414
2411(1.5g、1.19mモル、Yang等のJ.Am.Chem.Soc.2011、133、9964〜9967に従って調製された)の懸濁液及びDMF(2滴)に、塩化オキサリル(1.2mL、14.28mモル)を0℃で滴下した。懸濁液から透明な溶液にゆっくり変化した混合物を、室温で一晩撹拌し、次いで減圧下で濃縮した。得られた固体をヘプタンで洗浄し、真空乾燥した。化合物2414(1.5g、95%)が赤色の固体として得られた。
1.3−プロパンジオール(1.4mL、20.0mモル)、DMAP(1.5g、12.0mモル)、及びピリジン(1.2mL)のTHF(150mL)に、酸クロリド2522(1.6g、3.8mモル)のTHF(160mL)を0℃で加えた。10分後、DCC(800mg、3.9mモル)を加え、この混合物を室温で一晩撹拌した。次いで混合物をDCMで希釈し、水で洗浄し、乾燥させ(Na2SO4)、濾過し、濃縮した。次いで、化合物2523を、カラムクロマトグラフィ(SiO2)で精製し、DCM/TBME4/1から3/1で溶出させた。化合物2523(1.5g、86%)がオレンジ色の固体として得られた。
化合物2523(1.5g、3.3mモル)のDCM(50mL)、THF(100mL)、及びピリジン(2mL)に、DMAP(417mg、3.4mモル)及びテトラ酸クロリド2414(758mg、0.57mモル)を0℃で加えた。反応混合物を50℃で50時間撹拌し、減圧下で濃縮した。残留物をシリカゲル上にコーティングし、SiO2を含有するカラムの上に注いだ。DCM/TBME40/1の溶出により、完全には純粋でない異なる比の異性体(黄色部分)を含有する化合物2452の2留分を得た。ヘプタン及びMeOHで粉砕し、ガラスフィルタで濾過し(2x)、減圧下で50℃で乾燥させることで、2452が暗赤色の粉末として得られた(175mg及び440mg、36%)。M+Na=3024,1(MALDIで100%ピーク)、λmax(クロロホルム)=468nm、ε=104900及び560nm、ε=44500、λ(em)(クロロホルム)591nm。
A:2521
ジエステル1(5g、11.05mモル、TCIから得た)の1,4−ジオキサン懸濁液(300mL)、トルエン(100mL)、及び水(2mL)を、透明なオレンジ色の溶液が得られるまで還流した。1,4−ジオキサン(200mL)及び水(3mL)中のKOH(741mg、13.20mモル)を1時間かけて滴下した。この混合物を一晩還流させ、室温まで冷却し、減圧下で濃縮した。残留物をDCMで粉砕し、濾過して、残りのジエステル1を除去した。化合物1が全て除去されたことが1,4−ジオキサン中の固体残留物のTLCによって示されるまで、DCMによる洗浄を繰り返した。オレンジ色の固体を1,4−ジオキサンに溶解し、4N HClの1,4−ジオキサン溶液(80mモル、20mL)を加えた。この混合物を10分間撹拌し、減圧下で濃縮した。残留物を水中で粉砕し、濾過して、塩を除去した。収集した固体を再び水で、次いでヘプタンで洗浄し、真空中で乾燥させて、化合物2521をオレンジ色の固体として得た(1.5g、36%)。
2521(1.5g、4.0mモル)の懸濁液及びDMF(2滴)に、塩化オキサリル(3.4mL、40mモル)を0℃で滴下した。懸濁液から透明なオレンジ色の溶液にゆっくり変化した混合物を、室温で3時間撹拌し、次いで減圧下で濃縮した。得られた固体をヘプタンで洗浄し、真空乾燥した。化合物2522(1.6g、96%)がオレンジ色の固体として得られた。
化合物2354(378g、0.30mモル、Klok等のMacromol.Biosci.2003、3、729〜741に従って調製された)のDCM(50mL)、THF(100mL)、及びピリジン(2mL)溶液に、DMAP(147mg、1.20mモル)、酸クロリド2522(1.0g、0.241mモル)、及びDCC(62mg、0.30mモル)を0℃で加えた。反応混合物を50℃で50時間撹拌し、減圧下で濃縮した。残留物をヘプタン及びMeOHで洗浄して、黄色の不純物を除去した。化合物2455を更に第1のカラムクロマトグラフィによって精製した(SiO2、DCM/TBME30/1で溶出)。第2のカラムクロマトグラフィ(SiO2、DCM/MeOH200/1で溶出)によって、純粋な化合物2455(445mg、53%)が暗赤色の粉末として得られた。M+Na=2792,2(MALDIで100%ピーク)、λmax(クロロホルム)=466nm、ε=99100及び579nm、ε=41600、λ(em)(クロロホルム)607nm。
化合物2326(450mg、0.83mモル、米国特許第2014153247号に従って調製された)のDCM(20mL)、THF(20mL)、及びピリジン(0.5mL)溶液に、DMAP(98mg、0.80mモル)、テトラ酸クロリド2414(213mg、0.16mモル)、及びDCC(132mg、0.64mモル)を0℃で加えた。反応混合物を60℃で50時間撹拌し、減圧下で濃縮した。残留物をシリカゲル上にコーティングし、SiO2を含有するカラムの上に注いだ。DCM/TBME50/1から30/1の溶出により、化合物2517を含有する第1留分を得た。完全には純粋でない化合物2517をヘプタン及び熱いMeCNで粉砕し、ガラスフィルタで濾過し(2x)、減圧下で50℃で乾燥させることで、2517が暗赤色の粉末として得られた(220mg、41%)。M+Na=3364,2(MALDIで100%ピーク)、λmax(酢酸エチル)=504nm、ε=125000及び558nm、ε=40800、λ(em)(酢酸エチル)599nm。
A:2493
無水物2460(1.7g、5.9mモル、Peters等のJ.Soc.Dyes and Colorants 1989、105、29に従って調製された)、アニリン2323(1.7g、7.1mモル、Schrekker等のMacromolecules 2006、39、6341〜6354に従って調製された)、及び酢酸亜鉛二水和物(1.5g、7.1mモル)を、イミダゾール(30g)と共に混合した。反応混合物を160℃で窒素下で3時間撹拌した。室温まで冷却した後、酸性pHが得られるまで、混合物に5Nの塩酸水溶液を加え、水層をDCM(4x)で抽出した。結合した有機層を、1NのHCl水溶液、水で洗浄し、Na2SO4で乾燥させ、濾過し、減圧下で溶剤を除去した。DCM/EtOAc50/1から10/1を用いたカラムクロマトグラフィ(SiO2)によって、化合物2493(2.3g、77%)が黄色い固体として得られた。
化合物2493(2.8g、5.5mモル)のDCM(150mL)、THF(50mL)、及びピリジン(2mL)溶液に、DMAP(677mg、5.5mモル)及びテトラ酸クロリド2414(1.2g、0.9mモル)を0℃で加えた。反応混合物を35℃で50時間撹拌し、減圧下で濃縮した。残留物をシリカゲル上にコーティングし、カラムクロマトグラフィ(SiO2)の上に注いだ。DCM/TBME50/1から30/1の溶出により、化合物2440を含有する第1留分を得た。更に、DCM/TBME20/1の溶出により、化合物2493(800mg)が回収された。固体化合物2440を、ガラスフィルタ上でMeOH及びヘプタン(2x)で洗浄し、減圧下で50℃で乾燥させることで、赤い粉末が得られた(2.2g、76%)。M+Na=3228.3(MALDIで100%ピーク)、λmax(クロロホルム)=427nm、ε=162000及び562nm、ε=61600、λ(em)(クロロホルム)593nm。
Claims (15)
- 青色光成分を有する光源光を与える光源と、前記光源光の少なくとも一部を変換光に変換する光コンバータと、を備える照明デバイスであって、前記光コンバータがルミネッセンス物質を用いたポリマーマトリックスを備え、前記ルミネッセンス物質が、前記青色光成分の少なくとも一部を吸収することができる第1の基と、赤色光成分を有するルミネッセンス分子光を放出することができる第2の基と、を備える有機ルミネッセンス分子を備え、前記第1の基が、前記青色光成分の前記少なくとも一部の前記吸収によって獲得したエネルギの少なくとも一部を、赤色光成分を有する前記ルミネッセンス分子光の発生のために前記第2の基へ移動させ、前記第2の基が、
- 前記第1の基が、前記青色光成分の少なくとも一部を吸収する基を含み、緑色光及び黄色光のうち1つ以上に変換することができ、前記第2の基が前記緑色光及び黄色光のうち1つ以上を吸収し、前記第1の基がフェルスター共鳴エネルギ移動ドナーとして構成され、前記第2の基がフェルスター共鳴エネルギ移動アクセプタとして構成されている、請求項1に記載の照明デバイス。
- 前記ルミネッセンス分子が、第1の基としての1つ以上の黄色ドナー基と、第2の基としての1つ以上の赤色アクセプタ基と、を含む、請求項1又は2に記載の照明デバイス。
- 前記第1の基が、
- 前記ルミネッセンス分子がかさ高い基を更に含み、前記かさ高い基が第3級又は第4級炭素を含む、請求項1乃至4のいずれか1項に記載の照明デバイス。
- 前記かさ高い基が前記第1の基と前記第2の基との間に配置されている、請求項1乃至5のいずれか1項に記載の照明デバイス。
- 前記かさ高い基が、
- 前記第1の基が、
- 前記第1の基及び前記第2の基が、少なくとも4つの化学結合の共有結合鎖によって相互に分離され、前記鎖がC、O、N、及びSi原子のうち1つ以上を含む、請求項1乃至8のいずれか1項に記載の照明デバイス。
- 前記ルミネッセンス分子中の第1の基の数が第2の基の数よりも多い、請求項1乃至9のいずれか1項に記載の照明デバイス。
- 前記ルミネッセンス分子が、
- 前記光源が固体光源を含み、前記マトリックスが、ポリ(メチルメタクリレート)(PMMA)、ポリエチレンテレフタレート(PET)、及びポリエチレンナフタレート(PEN)のうち1つ以上を含み、前記照明デバイスが、緑色光成分及び黄色光成分のうち1つ以上を有する第2のルミネッセンス物質光を与える第2のルミネッセンス物質を更に含む、請求項1乃至11のいずれか1項に記載の照明デバイス。
- 青色光成分の少なくとも一部を吸収することができる第1の基と、赤色光成分を有するルミネッセンス分子光を放出することができる第2の基と、を備える有機ルミネッセンス分子を備えるルミネッセンス物質であって、前記第1の基が、前記青色光成分の前記少なくとも一部の吸収によって獲得した前記エネルギの少なくとも一部を、赤色光成分を有する前記ルミネッセンス分子光の発生のために前記第2の基へ移動させ、前記第2の基が、
-
- 光源光を与える光源と、前記光源光の少なくとも一部をルミネッセンス分子光に変換する、請求項13又は14に記載のルミネッセンス物質と、を備える、照明デバイス。
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JP2019519895A (ja) * | 2016-06-02 | 2019-07-11 | シグニファイ ホールディング ビー ヴィ | Fret結合エミッタに基づくプラズモン白色光源 |
JP2020132887A (ja) * | 2019-02-21 | 2020-08-31 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | 自発光組成物、これを用いて製造された色変換層およびこれを含むカラーフィルタおよび画像表示装置 |
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CN108495898B (zh) * | 2016-01-14 | 2020-10-27 | 巴斯夫欧洲公司 | 具有刚性2,2’-联苯氧基桥接的苝双酰亚胺 |
US11686611B2 (en) | 2017-02-24 | 2023-06-27 | Vestel Elektronik Sanayi Ve Ticaret A.S. | Acousto-optic transducer, array and method |
US20200123314A1 (en) | 2017-03-24 | 2020-04-23 | Basf Se | Poly(ethylene furan-2,5-dicarboxylate) as matrix material for color converters |
EP3673589A1 (en) * | 2017-08-24 | 2020-07-01 | Basf Se | Transmitter for transmitting data and for emitting electromagnetic radiation in the visible spectral range and data transmission system |
CN108485311B (zh) * | 2018-05-10 | 2019-08-30 | 上海贝通色彩科技有限公司 | 一种分散红染料组合物 |
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