JP2018510127A - 金属錯体およびこれを含む色変換フィルム - Google Patents
金属錯体およびこれを含む色変換フィルム Download PDFInfo
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- JP2018510127A JP2018510127A JP2017534351A JP2017534351A JP2018510127A JP 2018510127 A JP2018510127 A JP 2018510127A JP 2017534351 A JP2017534351 A JP 2017534351A JP 2017534351 A JP2017534351 A JP 2017534351A JP 2018510127 A JP2018510127 A JP 2018510127A
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 88
- 150000004696 coordination complex Chemical class 0.000 title description 6
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- 125000000217 alkyl group Chemical group 0.000 claims description 27
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- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000011159 matrix material Substances 0.000 claims description 17
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
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- ZVHRTJHLSYKEAK-UHFFFAOYSA-N ethyl 2-[5-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-2-oxo-3,4-dihydroquinolin-1-yl]acetate Chemical compound CCOC(=O)CN1C(=O)CCC2=C1C=CC=C2OC1=NC(=CC(CN)=C1)C(F)(F)F ZVHRTJHLSYKEAK-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- VVPGEFWZAXBZHR-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]sulfanyl-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)SC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 VVPGEFWZAXBZHR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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- DSSBJZCMMKRJTF-UHFFFAOYSA-N dibenzofuran-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3OC2=C1 DSSBJZCMMKRJTF-UHFFFAOYSA-N 0.000 description 3
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- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl 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
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000011145 styrene acrylonitrile resin Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 239000008096 xylene Substances 0.000 description 1
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- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
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Abstract
Description
[化学式1]
L1は直接結合;置換もしくは非置換のアルキレン基;または置換もしくは非置換のアリーレン基であり、
X1はCR12R13、NR14、O、またはSであり、
Y1は直接結合、CR15R16、NR17、O、またはSであり、
R1〜R17は互いに同一であるかまたは異なり、各々独立して水素;重水素;ハロゲン基;ニトリル基;ニトロ基;カルボニル基;カルボキシ基;エステル基;イミド基;アミド基;スルホン酸塩基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換の複素環基であるか、前記R7〜R10のうち隣接した2個は互いに連結されて置換もしくは非置換の炭化水素環;または置換もしくは非置換の複素環を形成することができ、
mは1〜3の整数である。
[化学式2]
L1、X1、Y1、R1〜R3、R5〜R11およびmの定義は前記化学式1と同様であり、
L2は直接結合;置換もしくは非置換のアルキレン基;または置換もしくは非置換のアリーレン基であり、
X2はCR23R24、NR25、O、またはSであり、
Y2は直接結合、CR26R27、NR28、O、またはSであり、
R18〜R28は互いに同一であるかまたは異なり、各々独立して水素;重水素;ハロゲン基;ニトリル基;ニトロ基;カルボニル基;カルボキシ基;エステル基;イミド基;アミド基;スルホン酸塩基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換の複素環基であるか、前記R18〜R21のうち隣接した2個は互いに連結されて置換もしくは非置換の炭化水素環;または置換もしくは非置換の複素環を形成することができ、
nは1〜3の整数である。
[化学式3]
L1、X1、R1〜R11およびmの定義は前記化学式1と同様であり、
Y2はCR15R16、NR17、O、またはSであり、
R15〜R17の定義は前記化学式1と同様である。
[化学式4]
L1、X1、R1〜R11およびmの定義は前記化学式1と同様である。
[化学式4−1]
L1、R1〜R14およびmの定義は前記化学式1と同様である。
前記Xは1族元素であり、前記R100は置換もしくは非置換の炭素数1〜30の直鎖もしくは分岐鎖のアルキレン基;または置換もしくは非置換の炭素数6〜30のアリーレン基である。
前記Xは1族元素であり、前記R100は置換もしくは非置換の炭素数1〜20の直鎖もしくは分岐鎖のアルキレン基;または置換もしくは非置換の炭素数6〜20のアリーレン基である。
前記R100は置換もしくは非置換のn−デカニレン基;または置換もしくは非置換のフェニレン基である。
前記R100はn−デカニレン基;またはメチル基で置換もしくは非置換されたフェニレン基である。
前記比較例1の有機蛍光体の代わりに化合物1−60を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
前記比較例1の有機蛍光体の代わりに化合物1−61を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
前記比較例1の有機蛍光体の代わりに化合物1−62を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
前記比較例1の有機蛍光体の代わりに化合物1−65を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
前記比較例1の有機蛍光体の代わりに化合物1−66を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
前記比較例1の有機蛍光体の代わりに化合物1−68を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
前記比較例1の有機蛍光体の代わりに化合物1−69を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
前記比較例1の有機蛍光体の代わりに化合物1−78を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
前記比較例1の有機蛍光体の代わりに化合物1−82を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
前記比較例1の有機蛍光体の代わりに化合物1−85を用いたことを除いては、前記比較例1と同様に色変換フィルムを製造した。
102 ・・・反射板
103 ・・・導光板
104 ・・・反射層
105 ・・・色変換フィルム
106 ・・・光分散パターン
Claims (13)
- 下記化学式1で表される化合物:
[化学式1]
L1は直接結合;置換もしくは非置換のアルキレン基;または置換もしくは非置換のアリーレン基であり、
X1はCR12R13、NR14、O、またはSであり、
Y1は直接結合、CR15R16、NR17、O、またはSであり、
R1〜R17は互いに同一であるかまたは異なり、各々独立して水素;重水素;ハロゲン基;ニトリル基;ニトロ基;カルボニル基;カルボキシ基;エステル基;イミド基;アミド基;スルホン酸塩基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換の複素環基であるか、前記R7〜R10のうち隣接した2個は互いに連結されて置換もしくは非置換の炭化水素環;または置換もしくは非置換の複素環を形成することができ、
mは1〜3の整数である。 - 前記化学式1で表される化合物は下記化学式2で表される、請求項1に記載の化合物:
[化学式2]
L1、X1、Y1、R1〜R3、R5〜R11およびmの定義は前記化学式1と同様であり、
L2は直接結合;置換もしくは非置換のアルキレン基;または置換もしくは非置換のアリーレン基であり、
X2はCR23R24、NR25、O、またはSであり、
Y2は直接結合、CR26R27、NR28、O、またはSであり、
R18〜R28は互いに同一であるかまたは異なり、各々独立して水素;重水素;ハロゲン基;ニトリル基;ニトロ基;カルボニル基;カルボキシ基;エステル基;イミド基;アミド基;スルホン酸塩基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のアリールオキシ基;置換もしくは非置換のアルキルチオキシ基;置換もしくは非置換のアリールチオキシ基;置換もしくは非置換のアルキルスルホキシ基;置換もしくは非置換のアリールスルホキシ基;置換もしくは非置換のアルケニル基;置換もしくは非置換のシリル基;置換もしくは非置換のホウ素基;置換もしくは非置換のアリールホスフィン基;置換もしくは非置換のホスフィンオキシド基;置換もしくは非置換のアミン基;置換もしくは非置換のアリール基;または置換もしくは非置換の複素環基であるか、前記R18〜R21のうち隣接した2個は互いに連結されて置換もしくは非置換の炭化水素環;または置換もしくは非置換の複素環を形成することができ、
nは1〜3の整数である。 - 前記化学式1で表される化合物は、フィルム状態で最大発光ピークが520nm〜550nm内に存在する、請求項1に記載の化合物。
- 前記化学式1で表される化合物は、フィルム状態で最大発光ピークが610nm〜650nm内に存在する、請求項1に記載の化合物。
- 前記化学式1で表される化合物は、フィルム状態で最大発光ピークが610nm〜650nm内に存在し、発光ピークの半値幅が60nm以下である、請求項1に記載の化合物。
- 前記化学式1で表される化合物の量子効率は0.9以上である、請求項1に記載の化合物。
- 最大発光波長が450nmの青色バックライトであり、青色LED光の明るさが600nitにおいて輝度スペクトルの測定時、前記化学式1で表される化合物は、フィルム状態で青色蛍光の減少分と赤色蛍光の増加分の比率が0.96以上である、請求項1に記載の化合物。
- 前記R1〜R6は互いに同一であるかまたは異なり、各々独立して水素;ハロゲン基;ニトリル基;スルホン酸塩基;カルボキシ基;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換の複素環基である、請求項1に記載の化合物。
- 前記R7〜R10のうち隣接した2個は互いに連結されて置換もしくは非置換の炭化水素環を形成する、請求項1に記載の化合物。
- 前記化学式1で表される化合物は下記化合物1−1〜1−111の中から選択されるいずれか1つである、請求項1に記載の化合物:
- 樹脂マトリックス、および前記樹脂マトリックス内に分散した請求項1〜10のいずれか1項に記載の化合物を含む色変換フィルム。
- 請求項11に記載の色変換フィルムを含むバックライトユニット。
- 請求項12に記載のバックライトユニットを含むディスプレイ装置。
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JP2020072270A (ja) * | 2018-10-31 | 2020-05-07 | 三星電子株式会社Samsung Electronics Co.,Ltd. | 有機化合物とそれを含む有機光電素子、イメージセンサ、及び電子素子 |
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WO2021085460A1 (ja) * | 2019-10-28 | 2021-05-06 | 東レ株式会社 | ピロメテンホウ素錯体を含む発光素子材料、発光素子、表示装置および照明装置 |
WO2021149510A1 (ja) * | 2020-01-24 | 2021-07-29 | 東レ株式会社 | ピロメテンホウ素錯体、それを含有する発光素子、表示装置および照明装置 |
KR20220131901A (ko) * | 2020-01-24 | 2022-09-29 | 도레이 카부시키가이샤 | 피로메텐붕소 착체, 그것을 함유하는 발광 소자, 표시 장치 및 조명 장치 |
KR102650329B1 (ko) | 2020-01-24 | 2024-03-25 | 도레이 카부시키가이샤 | 피로메텐붕소 착체, 그것을 함유하는 발광 소자, 표시 장치 및 조명 장치 |
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EP3252060A1 (en) | 2017-12-06 |
WO2016122117A1 (ko) | 2016-08-04 |
EP3252060A4 (en) | 2018-07-18 |
US10150911B2 (en) | 2018-12-11 |
EP3252060B1 (en) | 2019-07-17 |
US20170349822A1 (en) | 2017-12-07 |
TW201629073A (zh) | 2016-08-16 |
KR101590299B1 (ko) | 2016-02-01 |
JP6517348B2 (ja) | 2019-05-22 |
CN107207539A (zh) | 2017-09-26 |
TWI591071B (zh) | 2017-07-11 |
CN107207539B (zh) | 2020-06-19 |
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