JP2023518246A - 含ホウ素環式放出化合物及びそれを含む色変換フィルム - Google Patents
含ホウ素環式放出化合物及びそれを含む色変換フィルム Download PDFInfo
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- JP2023518246A JP2023518246A JP2022555947A JP2022555947A JP2023518246A JP 2023518246 A JP2023518246 A JP 2023518246A JP 2022555947 A JP2022555947 A JP 2022555947A JP 2022555947 A JP2022555947 A JP 2022555947A JP 2023518246 A JP2023518246 A JP 2023518246A
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 83
- 150000001875 compounds Chemical class 0.000 title claims description 72
- 125000004122 cyclic group Chemical group 0.000 title description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title description 2
- 229910052796 boron Inorganic materials 0.000 title 1
- 150000007980 azole derivatives Chemical class 0.000 claims abstract description 51
- 125000005647 linker group Chemical group 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- 150000002148 esters Chemical class 0.000 claims description 33
- 125000003367 polycyclic group Chemical group 0.000 claims description 29
- 125000002950 monocyclic group Chemical group 0.000 claims description 24
- 229920005989 resin Polymers 0.000 claims description 21
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- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 238000005424 photoluminescence Methods 0.000 claims description 15
- 238000006862 quantum yield reaction Methods 0.000 claims description 14
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- 150000007860 aryl ester derivatives Chemical class 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 238000012546 transfer Methods 0.000 claims description 9
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- 230000005284 excitation Effects 0.000 claims description 8
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
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- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 20
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- 238000000746 purification Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
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- 235000019341 magnesium sulphate Nutrition 0.000 description 13
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
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- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
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- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- OVTCUIZCVUGJHS-UHFFFAOYSA-N dipyrrin Chemical compound C=1C=CNC=1C=C1C=CC=N1 OVTCUIZCVUGJHS-UHFFFAOYSA-N 0.000 description 1
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- KWWOQRSLYPHAMK-UHFFFAOYSA-N ethyl 2-hydroxybutanoate Chemical compound CCOC(=O)C(O)CC KWWOQRSLYPHAMK-UHFFFAOYSA-N 0.000 description 1
- YLHBXVYOVUGHQA-UHFFFAOYSA-N ethyl 3-[(4-bromophenyl)-(3-ethoxycarbonyl-4,5,6,7-tetrahydro-2H-isoindol-1-yl)methyl]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylate Chemical compound BrC1=CC=C(C=C1)C(C=1NC(=C2CCCCC=12)C(=O)OCC)C=1NC(=C2CCCCC=12)C(=O)OCC YLHBXVYOVUGHQA-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- SSLMLMQQFNVQRK-UHFFFAOYSA-N n,n-diphenyl-4-[7-[4-(n-phenylanilino)phenyl]-2h-benzotriazol-4-yl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C2=NNN=C2C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 SSLMLMQQFNVQRK-UHFFFAOYSA-N 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- PKUHENDSMWXUBZ-UHFFFAOYSA-N tert-butyl 2-(hydroxyamino)-3-oxobutanoate Chemical compound CC(=O)C(C(=O)OC(C)(C)C)NO PKUHENDSMWXUBZ-UHFFFAOYSA-N 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
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- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
本出願は、2020年3月20日に出願された米国仮特許出願第62/992,776号の利益を主張し、この開示全体が引用することにより本明細書の一部をなす。
R4及びR5は共に連結して、追加の単環式炭化水素環構造、又は多環式炭化水素環構造を形成してもよく、
R7は、H又はアルキル、例えばC1~6アルキル(例えば、メチル、エチル、プロピル、イソプロピル、C4アルキル、C5アルキル、又はC6アルキル)であり得る。幾つかの実施形態においては、R7はHである。幾つかの実施形態においては、R7はメチル(-CH3)である。
R3及びR4はHとしてもよく、
R5及びR6はともに連結して、追加の単環式炭化水素環構造、又は多環式炭化水素環構造を形成してもよく、
R7及びR8は、独立して、H、メチル、又はエーテル基から選択され、
Lは、置換エステルリンカー基を含むリンカー基を表す)を有するBODIPY部分を含み得る。
実施形態1 フォトルミネッセンス錯体であって、
一般式:
非置換エステル又は置換エステルであるリンカー基と、
ホウ素-ジピロメテン(BODIPY)部分と、
を含み、
リンカー基は、アゾール誘導体とBODIPY部分とを共有結合し、アゾール誘導体は、第1の励起波長の光エネルギーを吸収し、エネルギーをBODIPY部分に移動させ、BODIPY部分は、アゾール誘導体からエネルギーを吸収し、第2のより高い波長の光エネルギーを放出し、フォトルミネッセンス錯体は80%を超える放出量子収率を有する、フォトルミネッセンス錯体。
R3及びR4は、独立して、H又はC1~C2アルキルから選択され、
R2及びR5は、独立して、H、飽和アルキル、不飽和アルキル、シアノ(-CN)、アルキルエステル、又はアリールエステルから選択され、
R2及びR3は、ともに連結して、追加の単環式炭化水素環構造、又は多環式炭化水素環構造を形成してもよく、
R4及びR5は、ともに連結して、追加の単環式炭化水素環構造、又は多環式炭化水素環構造を形成してもよく、
R7及びR8は、独立して、H、メチル基から選択されてもよく、
Lは、置換エステルリンカー基を含むリンカー基を表す)のものである、実施形態1に記載のフォトルミネッセンス錯体。
R3及びR4はメチルであり、
R5及びR6は、ともに連結して、追加の多環式炭化水素環構造を形成し、
R7及びR8は、独立して、H、メチル又はエーテル基から選択することができ、
Lは、置換エステルリンカー基を含むリンカー基を表す)である、実施形態1に記載のフォトルミネッセンス錯体。
透明基材層と、
樹脂マトリックスを含む色変換層と、
樹脂マトリックス内に分散された実施形態1、2、3、4、5、6、7、8、9、10、11、12及び13に記載のフォトルミネッセンス化合物を含む少なくとも1つのフォトルミネッセンス錯体と、
を含む、色変換フィルム。
実施形態1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、及び17に記載のフォトルミネッセンス錯体、及びバインダー樹脂を溶媒中に溶解することと、
透明な基材の対置表面の1つに混合物を塗布することと、
を含む、方法。
工程1:7.6mLの25%HBr/AcOHを、19.76gの固体N-Boc-Gly-N’-メトキシ-N’-メチルアミド(90.4mmol)にゆっくりと加えた。この溶液を室温で45分間撹拌した。次に、この溶液に200mLのジエチルエーテルを加え、白色沈殿を生じた。沈殿物を濾過し、グリシンN’-メトキシ-N’-メチルアミドHBr塩18.03g、収率100%を得た。LCMS(M+H):119。1H NMR(DMSO-d6) δ 8.04(3H,s)、3.9(s,2H)、3.72(s,3H)、3.17(s,3H)。
ガラス基材を、実質的に以下のように作製した。1インチ×1インチの大きさの1.1mm厚のガラス基材をサイズに合わせて切断した。次に、ガラス基材を洗剤及び脱イオン(DI)水で洗浄し、新しいDI水ですすぎ、約1時間超音波処理した。次に、ガラスをイソプロパノール(IPA)中に浸し、約1時間超音波処理した。次に、ガラス基材をアセトン中に浸し、約1時間超音波処理した。次に、ガラスをアセトン浴から取り出し、室温にて窒素ガスで乾燥させた。
Claims (22)
- フォトルミネッセンス錯体であって、
青色光吸収アゾール誘導体と、
非置換エステル又は置換エステルを含むリンカー基と、
を含み、
前記リンカー基は前記青色光吸収アゾール誘導体とホウ素-ジピロメテン(BODIPY)部分とを共有結合させ、
前記青色光吸収アゾール誘導体は、式:
前記アゾール誘導体は、第1の励起波長の光エネルギーを吸収し、エネルギーを前記BODIPY部分に移動させ、前記BODIPY部分は、前記アゾール誘導体からエネルギーを吸収し、第2のより高い波長の光エネルギーを放出する、フォトルミネッセンス錯体。 - 前記BODIPY部分が一般式:
R3及びR4は、独立して、H又はC1~C2アルキルであり、
R2及びR5は、独立して、H、アルキル、アルケニル、アルキニル、-CN、アルキルエステル、又はアリールエステルであり、
R2及びR3はともに連結して、追加の単環式炭化水素環構造、又は多環式炭化水素環構造を形成してもよく、
R4及びR5は、ともに連結して、追加の単環式炭化水素環構造、又は多環式炭化水素環構造を形成してもよく、
R7及びR8は、独立して、H又はメチルであり、
Lはリンカー基である)のものである、請求項1に記載のフォトルミネッセンス錯体。 - ZがSである、請求項1、2、又は3に記載のフォトルミネッセンス錯体。
- ZがNR10であり、R10が置換フェニルである、請求項1、2、又は3に記載のフォトルミネッセンス錯体。
- R7及びR8がメチルである、請求項2、3、4、5、又は6に記載のフォトルミネッセンス錯体。
- R1、R3、R4及びR6がC1~C2アルキルである、請求項2、4、5、6、又は7に記載のフォトルミネッセンス錯体。
- R1、R3、R4及びR6がメチルである、請求項2、4、5、6、7、又は8に記載のフォトルミネッセンス錯体。
- 色変換フィルムであって、
透明基材層と、
樹脂マトリックスを含む色変換層と、
前記樹脂マトリックス内に分散された請求項1、2、3、4、5、6、7、8、9、10、11、12、又は13に記載のフォトルミネッセンス化合物を含むフォトルミネッセンス錯体と、
を含む、色変換フィルム。 - 一重項酸素消光剤を更に含む、請求項14に記載の色変換フィルム。
- 遊離基捕捉剤を更に含む、請求項14又は15に記載の色変換フィルム。
- 前記フィルムが1μmから200μmの間の厚さを有する、請求項14、15又は16に記載の色変換フィルム。
- 約400nm~約480nmの波長範囲の光を吸収し、約510nm~約560nmの波長範囲の光を放出する、請求項14、15、16、又は17に記載の色変換フィルム。
- 約400nm~約480nmの波長範囲の光を吸収し、約575nm~約645nmの波長範囲の光を放出する、請求項14、15、16、又は17に記載の色変換フィルム。
- 前記放出量子収率が70%以上である、請求項14、15、16、17、18又は19に記載の色変換フィルム。
- 請求項14、15、16、17、18、19、又は20に記載の色変換フィルムを備えるバックライトユニット。
- 請求項21に記載のバックライトユニットを備えるディスプレイデバイス。
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