JP7402979B2 - 白金金属錯体及び有機エレクトロルミネセンスデバイスにおけるその用途 - Google Patents
白金金属錯体及び有機エレクトロルミネセンスデバイスにおけるその用途 Download PDFInfo
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims description 24
- 239000010410 layer Substances 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 239000012044 organic layer Substances 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000013086 organic photovoltaic Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 230000000903 blocking effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 1
- RXNPEQZHMGFNAY-GEALJGNFSA-N (5R)-4-[(1S,6R)-5-[(2S)-2-(4-chlorophenyl)-3-(propan-2-ylamino)propanoyl]-2,5-diazabicyclo[4.1.0]heptan-2-yl]-5-methyl-6,8-dihydro-5H-pyrido[2,3-d]pyrimidin-7-one Chemical compound C[C@@H]1CC(=O)NC2=C1C(=NC=N2)N3CCN([C@H]4[C@@H]3C4)C(=O)[C@H](CNC(C)C)C5=CC=C(C=C5)Cl RXNPEQZHMGFNAY-GEALJGNFSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 101150050192 PIGM gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NPUXORBZRBIOMQ-RUZDIDTESA-N [(2R)-1-[[4-[[3-(benzenesulfonylmethyl)-5-methylphenoxy]methyl]phenyl]methyl]-2-pyrrolidinyl]methanol Chemical compound C=1C(OCC=2C=CC(CN3[C@H](CCC3)CO)=CC=2)=CC(C)=CC=1CS(=O)(=O)C1=CC=CC=C1 NPUXORBZRBIOMQ-RUZDIDTESA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
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- C07—ORGANIC CHEMISTRY
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- C07F15/0086—Platinum compounds
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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Description
ここで、
R1~R32はそれぞれ、独立して、水素、重水素、ハロゲン、1~20個の炭素原子を有する置換又は非置換のアルキル基、3~20個の環炭素原子を有する置換又は非置換のシクロアルキル基、1~20個の炭素原子を有する置換又は非置換のアルコキシ基、6~30個の炭素原子を有する置換又は非置換のアリール基、3~30個の炭素原子を有する置換又は非置換のヘテロアリール基又はシアノ基から選択され、Ar1及びAr2はそれぞれ、独立して、6~14個の炭素原子の芳香族基又は3~12炭素原子のヘテロ芳香族基から選択され、前記ヘテロ芳香族基におけるヘテロ原子は、O、S、Nの1つ又は複数から選択され、前記置換は、重水素、ハロゲン、C1~8アルキル基による置換である。
〈実施例1〉
窒素の保護下で、化合物1a(4.9g、10.0mmol)(文献J. Mater. Chem., 2014, 2, 2028を参照して合成されたもの)をテトラヒドロフラン(50mL)に溶解し、-78℃まで冷却し、n-ブチルリチウムBuLi(2.0M、11mL)を滴下し、30分間撹拌した後、化合物1b(4.2g、25.0mmol)(文献J. Am. Chem. Soc, 2008, 130, 9942を参照して合成されたもの)のテトラヒドロフラン溶液(10mL)を上記の溶液に滴下し、30分間撹拌した後、室温まで加熱し、1時間撹拌し続けた。上記の反応液を希塩酸溶液(1M、100mL)に入れ、30分間撹拌した。混合物をジクロロメタンで3回抽出し、有機相を合わせた。有機相を無水硫酸ナトリウムで乾燥させた後、回転蒸発で溶媒を除去して、淡黄色固体を取得した。残留物をカラムクロマトグラフィーにより分離して、淡黄色油状物を取得した(2.8g、収率51%)。ESI-MS(m/z):543.2(M+1)。
窒素の保護下で、2-ブロモビフェニル(2.3g、10.0mmol)をテトラヒドロフラン(30mL)に溶解し、-78℃まで冷却し、n-ブチルリチウムBuLi(2.0M、11mL)を滴下し、30分間撹拌した後、化合物1c(2.6g、4.8mmol)のテトラヒドロフラン溶液(10mL)を上記の溶液に滴下した。30分間撹拌した後、室温まで加熱し、1時間撹拌し続けた。上記の反応液を水に入れ、ジクロロメタン3回抽出し、有機相を合わせた。有機相を無水硫酸ナトリウムで乾燥させた後、回転蒸発で溶媒を除去して、淡黄色固体を取得した。上記の固体を酢酸(50mL)に溶解し、濃硫酸(4mL)を添加し、窒素の保護下で、一晩還流した。室温に冷却した後、上記の反応液を水に入れ、ジクロロメタンで3回抽出し、有機相を合わせた。有機相を無水硫酸ナトリウムで乾燥させた後、回転蒸発で溶媒を除去し、残留物をカラムクロマトグラフィーにより分離して、淡黄色固体を取得した(2.8g、収率71%)。ESI-MS(m/z):815.3(M+1)。
化合物1d(2.5g、3.1mmol)、テトラクロリド白金(II)酸カリウム(1.5g、3.6mmol)及び250mL酢酸をフラスコに入れ、窒素の保護下で、48時間還流撹拌した。室温に冷却した後、上記の反応液を水に入れ、濾過して粗生成物を取得し、再結晶して黄色固体を取得した(2.5g、収率80%)。ESI-MS(m/z):1008.3(M+1)。
〈実施例2〉
2-ブロモビフェニルを化合物22a(文献Dyes Pigm., 2015, 121, 7を参照して合成されたもの)に置き換え、化合物1dの調製方法を参照して中間体22bを合成し、淡黄色固体2.9gを取得し、収率が69%であった。ESI-MS(m/z):1039.6(M+1)。
1dを化合物22bに置き換え、錯体1の調製方法を参照して錯体22を合成し、黄色固体2.1gを取得し、収率が73%であった。ESI-MS(m/z):1232.5(M+1)。
〈実施例3〉
次に、ITO上に厚さ10nmのHATCNを正孔注入層30として蒸着した。
次に、化合物HTを蒸着して、厚さ40nmの正孔輸送層40を形成した。
次に、正孔輸送層上に厚さ20nmの発光層50を蒸着した。発光層は、錯体1(20%)とCBP(80%)の混合ドーピングからなった。
次に、発光層上に厚さ40nmのAlQ3を電子輸送層60として蒸着した。
最後に、1nmのLiFを電子注入層70として、及び100nmのAlをデバイスの陰極80として蒸着した。
〈実施例4〉
〈比較例〉
表1
〈実施例5〉
表2
Claims (12)
- 式(I)の構造を有する白金金属錯体であって、
式(I)中、
R1~R32はそれぞれ、独立して、水素、重水素、ハロゲン、1~20個の炭素原子を有する置換もしくは非置換のアルキル基、3~20個の環炭素原子を有する置換もしくは非置換のシクロアルキル基、1~20個の炭素原子を有する置換もしくは非置換のアルコキシ基、6~30個の炭素原子を有する置換もしくは非置換のアリール基、3~30個の炭素原子を有する置換もしくは非置換のヘテロアリール基、又はシアノ基から選択され、Ar1~Ar2はそれぞれ、独立して、6~14個の炭素原子の芳香族基から選択され、前記置換は、重水素、ハロゲン又はC1~8アルキル基による置換である、ことを特徴とする白金金属錯体。 - R1~R32はそれぞれ、独立して、水素、重水素、ハロゲン、1~6個の炭素原子を有する置換もしくは非置換のアルキル基、3~6個の環炭素原子を有する置換もしくは非置換のシクロアルキル基、6~12個の炭素原子を有する置換もしくは非置換のアリール基、又は3~6個の炭素原子を有する置換もしくは非置換のヘテロアリール基から選択され、Ar1及びAr2はいずれも、フェニル基である、ことを特徴とする請求項1に記載の白金金属錯体。
- R1~R32はそれぞれ、独立して、水素、重水素、1~4個の炭素原子を有する置換もしくは非置換のアルキル基、3~6個の環炭素原子を有する置換もしくは非置換のシクロアルキル基、フェニル基、トリル基又はピリジン基から選択され、Ar1とAr2は同じである、ことを特徴とする請求項2に記載の白金金属錯体。
- R1~R32はそれぞれ、独立して、水素、メチル、イソプロピル基又はtert-ブチル基から選択される、ことを特徴とする請求項3に記載の白金金属錯体。
- R1~R32のうち、R1~R3、R12~R17及びR26~R30は水素であり、その他は水素、メチル、イソプロピル基又はtert-ブチル基である、ことを特徴とする請求項4に記載の白金金属錯体。
- 以下のうちのいずれかの構造を有する、ことを特徴とする請求項1に記載の白金金属錯体。
- 以下のいずれかの構造を有する、ことを特徴とする請求項6に記載の白金金属錯体。
- 以下の構造を有する、ことを特徴とする請求項1~7のいずれか一項に記載の白金金属錯体のリガンド。
- 有機エレクトロルミネセンスデバイス、有機薄膜トランジスタ、有機光起電力デバイス、発光電気化学セル又は化学センサにおける請求項1~7のいずれか一項に記載の白金金属錯体の使用。
- 陰極、陽極及び有機層を含み、前記有機層は、正孔注入層、正孔輸送層、発光層、正孔阻止層、電子注入層及び電子輸送層のうちの1又は複数の層を有し、前記有機層は、請求項1~7のいずれか一項に記載の白金金属錯体を含む、ことを特徴とする有機エレクトロルミネセンスデバイス。
- 請求項1~7のいずれか一項に記載の白金金属錯体を含む層は、発光層である、ことを特徴とする請求項10に記載の有機エレクトロルミネセンスデバイス。
- 前記有機層の総厚さは1~1000nmである、ことを特徴とする請求項10に記載の有機エレクトロルミネセンスデバイス。
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