CN102911212A - 有机金属化合物及包含其之有机电致发光装置 - Google Patents
有机金属化合物及包含其之有机电致发光装置 Download PDFInfo
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- CN102911212A CN102911212A CN2011102386991A CN201110238699A CN102911212A CN 102911212 A CN102911212 A CN 102911212A CN 2011102386991 A CN2011102386991 A CN 2011102386991A CN 201110238699 A CN201110238699 A CN 201110238699A CN 102911212 A CN102911212 A CN 102911212A
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- organometallic compound
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- electroluminescent device
- acetylacetone
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- 150000002902 organometallic compounds Chemical class 0.000 title claims abstract description 26
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 16
- WLSOCBTUHQAHMF-UHFFFAOYSA-N pentane-2,3-dione pentane-2,4-dione Chemical compound CC(C(CC)=O)=O.C(C)(=O)CC(C)=O WLSOCBTUHQAHMF-UHFFFAOYSA-N 0.000 claims description 8
- -1 sec.-propyl Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 238000004020 luminiscence type Methods 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 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 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 5
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 abstract 4
- 239000003446 ligand Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000000463 material Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 4
- 229910009112 xH2O Inorganic materials 0.000 description 4
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000002604 ultrasonography Methods 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- 235000007466 Corylus avellana Nutrition 0.000 description 2
- 240000003211 Corylus maxima Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000003809 water extraction Methods 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229910000611 Zinc aluminium Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- HXFVOUUOTHJFPX-UHFFFAOYSA-N alumane;zinc Chemical compound [AlH3].[Zn] HXFVOUUOTHJFPX-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供一有机金属化合物及包含其之有机电致发光装置。该有机金属化合物具以下所示之化学式，其中，X系为C-H或是N，Y系为CH2或是NH；R1系氢、或C1-8烷基；以及，A1系乙酰丙酮(acetylacetone)配位基、具有苯环之乙酰丙酮(acetylacetone)配位基、或其衍生物。
Description
技术领域
本发明关于一种有机金属化合物及包含其之有机电致发光装置，特别关于一种有机金属磷光化合物及包含其之磷光有机电致发光装置。
背景技术
有机电致发光装置(organic electroluminescent device)，亦称作有机发光二极管(organic light-emitting diode；OLED)，是以有机层作为主动层的一种发光二极管(LED)。由于有机电致发光装置具有低电压操作、高亮度、重量轻、广视角、以及高对比值等优点，近年来已渐渐使用于平面面板显示器(flat panel display)上。与液晶显示器不同，有机电致发光显示器所包含之有机发光二极管画素数组系具有自发光的特性，因此不需外加背光源。
一般而言，有机发光二极管组件包括一对电极，以及在电极之间的一有机发光介质层。发光是导因于以下的现象。当电场施于两电极时，阴极射出电子到有机发光介质层，阳极射出电洞到有机发光介质层。当电子与电洞在有机发光介质层内结合时，会产生激子(excitons)。电子和电洞的再结合就伴随着发光。
依据电洞和电子的自旋态(spin state)，由电洞和电子之再结合而产生的激子可具有三重态(triplet)或单重态(singlet)之自旋态。由单重态激子(singlet exciton)所产生的发光为荧光(fluorescence)，而由三重态激子(triplet exciton)所产生的发光为磷光(phosphorescence)。磷光的发光效率是荧光的三倍。因此，发展高效率的磷光材料以增进有机发光二极管组件的发光效率是非常重要的。
不过，传统红光有机磷光发光材料的发光效率并不佳，然而制作高CRI白光就必须要用红光、绿光和蓝光等三原色光谱的发光材料，且具有红光光谱区域的有机发光二极管组件照射伤口时对伤口愈合有帮助。因此，开发出红位移的有机磷光发光材料，对于有机发光二极管技术而，是一个很重要的课题。
发明内容
本发明提出一种有机金属化合物，其化学结构具有4-phenylnaphtho[1，2-b]thiophene基团，可使材料光色达到红光光谱。本发明所述之有机金属化合物，可应用在有机电致发光装置，作为发光单元的材料，提升有机电致发光装置的组件效率。
根据本发明一较佳实施例，该有机金属化合物，具有如式(I)或式(II)所示之化学结构：
式(I)
式(II)
其中，
X系为C-H或是N，Y系为CH2或是NH；
R1系氢、或C1-8烷基；以及
A1系乙酰丙酮(acetylacetone)配位基、具有苯环之乙酰丙酮(acetylacetone)配位基、或其衍生物。
根据本发明另一较佳实施例，本发明系提供一种有机电致发光装置，该装置包含一对电极；以及一有机发光单元，配置于该对电极之间，其中该有机发光单元包含上述之有机金属化合物，可作为红光磷光掺杂材料。
以下藉由数个实施例及比较实施例，以更进一步说明本发明之方法、特征及优点，但并非用来限制本发明之范围，本发明之范围应以所附之申请专利范围为准。
附图说明
图1为本发明一较佳实施例所述之有机电致发光装置的剖面结构图。
主要组件符号说明
有机电致发光装置～10；
基底～12；
下电极～14；
有机发光单元～16；以及
上电极～18。
具体实施方式
有机金属化合物
本发明系揭露一种有机金属化合物，系为具有式(I)所示之化学式：
式(I)
式(II)
其中，
X系为C-H或是N，Y系为CH2或是NH；
R1系氢、或C1-8烷基；以及
A1系乙酰丙酮(acetylacetone)配位基、具有苯环之乙酰丙酮(acetylacetone)配位基、或其衍生物。
根据本发明之实施例，A1之另一侧系以氧原子与Ir键合，A1之另一侧同样系以氧原子与Ir键合。
根据本发明其它实施例，该有机金属化合物可具有如式(III)、式(IV)、或式(V)所示之结构：
式(III)
式(IV)
式(V)
其中，R1系氢、或C1-8烷基；R2系为氢、苯基(phenyl)、苯基衍生物、或联苯基(biphenyl)；Y系为CH2或是NH。
表1系列举出本发明一系列较佳实施例所得之具有公式(I)或式(II)之有机金属化合物，其各自之化学结构均详列于表中，因此可清楚辨识其不同取代基所分别代表的官能基。
表1
为进一步说明本发明有机金属化合物的制备方法，以下特别详述实施例1-4所示之化合物其制备流程。
实施例1
化合物Ir-THQ-acac之合成
取化合物1(2.00g，10.00mmole)放入250mL单颈瓶中，加入50.00mL甲苯(toluene)并接上加料漏斗。接着在加料漏斗中加入市售化合物2(1.29g，10.00mmole)、碳酸钾(2M，20mL)、Pd(PPH3)4(0.43g)、及(t-Bu)3P)(0.23g)，于室温下加入反应瓶中，加热回流24小时。反应完成及纯化后，可得化合物3(1.41g，6.90mmole，69％)。上述反应之反应式如下所示：
将化合物3(1.00g，4.90mmole)放入250mL单颈圆底瓶中，加入铁粉(2.17g，38.90mmol)与EtOH∶AcOH∶H2O＝2∶2∶1的混合溶剂50mL。使用机械搅拌，加热回流15分钟，室温下搅拌25分钟，抽气过滤将铁粉等固体滤掉，以NaHCO3中和之，以乙酸乙酯和水萃取，减压浓缩后，可得到淡褐色液体，不需经过管柱层析，就可以得到纯度高化合物4，产率91％。上述反应之反应式如下所示：
将化合物4(1.00g，5.70mmole)放入250mL单颈圆底瓶中，加入甲苯(100mL)，加热至甲苯回流。反应数小时后，加入1当量TFA及化合物5(0.97g)，并通入氧气，持续加热至甲苯回流。反应完成后，可得化合物6(79％)。上述反应之反应式如下所示：
将化合物6(3.68g，11.60mmol)和水合氯化铱化合物(IrCl3.xH2O，1.65g)放入100mL单颈圆底瓶中，分别加入2-methoxy ethanol(2-甲氧基乙醇，15mL)和水(5mL)，加热至140℃。反应24小时后，分别加入acac(0.72g)、碳酸钠(0.76g)和30mL的2-methoxyethanol，加热至140℃。反应24小时后，回至室温，加入50mL水，过滤，可得红色固体产物。再以管柱层析法纯化(二氯甲烷/正己烷＝1/3)，得到Ir-THQ-acac。上述反应之反应式如下所示：
利用核磁共振光谱分析Ir-THQ-acac，所得之光谱信息如下：
1H NMR(CDCl3，200MHz)δ8.49(d，J＝5.4Hz，2H)，8.41(d，J＝8.8Hz，2H)，8.23(d，J＝8.4Hz，2H)，8.02(d，J＝7.6Hz，2H)，7.69(d，J＝5.4Hz，2H)，7.44(t，J＝8.0Hz，2H)，7.28(t，J＝8.0Hz，2H)，7.03(dd，J＝8.0，1.8Hz，2H)，6.71(d，J＝1.8Hz，2H)，4.47(s，1H)，1.35(s，6H)，0.88(s，18H)。
实施例2
化合物Ir-THQ-ph ac之合成
将化合物6(3.68g，11.60mmol)和水合氯化铱化合物(IrCl3.xH2O，1.65g)放入100mL单颈圆底瓶中，分别加入2-methoxy ethanol(15mL)和水(5mL)，加热至140℃。反应24小时后，分别加入化合物7(1.30g)、碳酸钠(0.76g)和30mL的2-methoxyethanol(2-甲氧基乙醇)，加热至140℃。反应24小时后，回至室温，加入50mL水，过滤，可得红色固体产物。再以管柱层析法纯化(二氯甲烷/正己烷＝1/3)，得到Ir-THQ-phac。上述反应之反应式如下所示：
利用核磁共振光谱分析Ir-THQ-phac，所得之光谱信息如下：
1H NMR(CDCl3，200MHz)δ8.51(d，J＝5.4Hz，2H)，8.45(d，J＝8.8Hz，2H)，8.28(d，J＝8.4Hz，2H)，8.08(d，J＝7.6Hz，2H)，7.71(d，J＝5.4Hz，2H)，7.66(d，J＝8.0Hz，2H)，7.46(t，J＝8.0Hz，2H)，7.41(d，J＝1.8Hz，1H)，7.28(t，J＝8.0Hz，2H)，7.13(dd，J＝8.0，1.8Hz，2H)，7.03(dd，J＝8.0，1.8Hz，2H)，6.73(d，J＝1.8Hz，2H)，1.36(s，6H)，0.89(s，18H)。
实施例3
化合物Ir-THQ-N-acac之合成
取化合物8(2.02g，10.00mmole)放入250mL单颈瓶中，加入50.00mL甲苯(toluene)并接上加料漏斗。接着在加料漏斗中加入市售化合物9(1.29g，10.00mmole)、碳酸钾(2M，20mL)、Pd(PPH3)4(0.43g)、及(t-Bu)3P)(0.23g)，于室温下加入反应瓶中。反应完成及纯化后，可得化合物10。上述反应之反应式如下所示：
将化合物10(1.01g，4.90mmole)放入250mL单颈圆底瓶中，加入铁粉(2.17g，38.90mmol)与EtOH∶AcOH∶H2O＝2∶2∶1的混合溶剂50mL。使用机械搅拌，加热回流15分钟，室温下搅拌25分钟，抽气过滤将铁粉等固体滤掉，以NaHCO3中和之，以乙酸乙酯和水萃取，减压浓缩后，可得到淡褐色液体，不需经过管柱层析，就可以得到纯度高化合物11。上述反应之反应式如下所示：
将化合物11(1.00g，5.70mmole)放入250mL单颈圆底瓶中，加入甲苯(100mL)，加热至甲苯回流。反应数小时后，加入1当量TFA及化合物5(0.97g)，并通入氧气，持续加热至甲苯回流。反应完成后，可得化合物12(72％)。上述反应之反应式如下所示：
将化合物12(3.69g，11.60mmol)和水合氯化铱化合物(IrCl3.xH2O，1.65g)放入100mL单颈圆底瓶中，分别加入2-methoxy ethanol(15mL)和水(5mL)，加热至140℃。反应24小时后，分别加入acac(
0.72g)、碳酸钠(0.76g)和30mL的2-methoxyethanol，加热至140℃。反应24小时后，回至室温，加入50mL水，过滤，可得红色固体产物。再以管柱层析法纯化(二氯甲烷/正己烷＝1/3)，得到Ir-THQ-N-acac。上述反应之反应式如下所示：
实施例4
化合物Ir-THQ-N-phac之合成
将化合物12(3.69g，11.60mmol)和水合氯化铱化合物(IrCl3.xH2O，1.65g)放入100mL单颈圆底瓶中，分别加入2-methoxy ethanol(15mL)和水(5mL)，加热至140℃。反应24小时后，分别加入化合物7(1.30g)、碳酸钠(0.76g)和30mL的2-methoxyethanol，加热至140℃。反应24小时后，回至室温，加入50mL水，过滤，可得红色固体产物。再以管柱层析法纯化(二氯甲烷/正己烷＝1/3)，得到Ir-THQ-N-phac。上述反应之反应式如下所示：
有机电致发光装置
请参照第1图，系显示一符合本发明所述之有机电致发光装置10之剖面结构示意图，该有机电致发光装置10包括一基底12、一下电极14、一有机发光单元16及一上电极18。该有机电致发光装置10可为上发光、下发光、或双面发光有机电致发光装置。该基底可例如为玻璃、塑料基板、或半导体基板。该下电极14及上电极18之材质可例如为锂、镁、钙、铝、银、铟、金、钨、镍、铂、铜、铟锡氧化物(ITO)、铟锌氧化物(IZO)、锌铝氧化物(AZO)、氧化锌(ZnO)或其结合，而其形成方式可为热蒸镀、溅射或电浆强化式化学气相沉积方式。此外，该下电极14及上电极18至少一者需具有透光的性质。
该有机发光单元16至少包含一发光层，可更包含一电洞注入层、一电洞传输层、一电子传输层、一电子注入层或其它膜层。值得注意的是，根据本发明较佳实施例，该有机发光单元16必需包含本发明所述具有公式(I)或式(II)之有机金属化合物。换言之，在该有机发光单元16中，至少有一膜层包含该有机金属化合物。
根据本发明另一较佳实施例，该有机电致发光装置可为一磷光有机电致发光装置，而该磷光发光单元之发光单元包含一主体(host)材料及一磷光掺杂材料，而该磷光掺杂材料材料包含本发明所述具有式(I)或式(II)所示结构之有机金属化合物。熟悉本技术者可视所使用之有机电致发光材料及所需之组件特性，将本发明所述之有机金属化合物与所需的磷光掺杂材料掺杂，并改变所搭配的掺杂物之掺杂量。因此，掺杂物之掺杂量之多寡非关本发明之特征，非为限制本发明范围之依据。
为进一步说明本发明有机电致发光装置，以下实施例系将由实施例1所得之有机金属化合物作为掺杂材料，提供数个有机电致发光装置的实施例，来验证本发明所述之有机金属化合物具有突出的光电特性。
实施例5：
使用中性清洁剂、丙酮、及乙醇以超音波振荡将已制作图样的ITO(厚度为100nm)玻璃基底洗净。
接着，以氮气将基材吹干，然后UV-OZONE 30分钟，接着于10-6torr的压力下依序沉积NPB(N，N′-di(naphthalene-l-yl)-N，N′-diphenyl-benzidine、厚度为40nm)、CBP(4，4′-N，N′-dicarbazole-biphenyl)掺杂Ir-THQ-acac
(CBP与Ir-THQ-acac的比例为100∶3、厚度为30nm)、Bphen(4，7-diphenyl-1，10-phenanthroline、厚度为30nm)、LiF(厚度为0.5nm)、及Al(厚度为120nm)，封装后获致该电致发光装置(1)。该电致发光装置(1)之结构可表示为：
NPB(40nm)/CBP：Ir-THQ-acac(3％)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)
接着，量测该电致发光装置(1)之光学特性，其量测结果如下：
最佳组件发光效率在34.1cd/A，19.5lm/W；
组件效率在11.9cd/A，4.2lm/W1000cd/m2；
电致发光波长(EL)为612nm，CIE坐标为(0.63，0.35)。
实施例6：
使用中性清洁剂、丙酮、及乙醇以超音波振荡将已制作图样的ITO(厚度为100nm)玻璃基底洗净。
接着，以氮气将基材吹干，然后UV-OZONE 30分钟，接着于10-6torr的压力下依序沉积NPB(N，N′-di(naphthalene-l-yl)-N，N′-diphenyl-benzidine、厚度为40nm)、CBP(4，4′-N，N′-dicarbazole-biphenyl)掺杂Ir-THQ-acac
(CBP与Ir-THQ-acac的比例为100∶4、厚度为30nm)、Bphen(4，7-diphenyl-1，10-phenanthroline、厚度为30nm)、LiF(厚度为0.5nm)、及Al(厚度为120nm)，封装后获致该电致发光装置(2)。该电致发光装置(2)之结构可表示为：
NPB(40nm)/CBP：Ir-THQ-acac(4％)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)
接着，量测该电致发光装置(2)之光学特性，其量测结果如下：
最佳组件发光效率在35.9cd/A，28.2lm/W；
组件效率在11.4cd/A，5.7lm/W1000cd/m2；
电致发光波长(EL)为616nm，CIE坐标为(0.65，0.34)。
实施例7：
使用中性清洁剂、丙酮、及乙醇以超音波振荡将已制作图样的ITO(厚度为100nm)玻璃基底洗净。
接着，以氮气将基材吹干，然后UV-OZONE 30分钟，接着于10-6torr的压力下依序沉积NPB(N，N′-di(naphthalene-l-yl)-N，N′-diphenyl-benzidine、厚度为40nm)、CBP(4，4′-N，N′-dicarbazole-biphenyl)掺杂Ir-THQ-acac
(CBP与Ir-THQ-acac的比例为100∶5、厚度为30nm)、Bphen(4，7-diphenyl-1，10-phenanthroline、厚度为30nm)、LiF(厚度为0.5nm)、及Al(厚度为120nm)，封装后获致该电致发光装置(3)。该电致发光装置(3)之结构可表示为：
NPB(40nm)/CBP：Ir-THQ-acac(4％)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)
接着，量测该电致发光装置(3)之光学特性，其量测结果如下：
最佳组件发光效率在18.7cd/A，9.7lm/W；
组件效率在10.0cd/A，3.5lm/W1000cd/m2；
电致发光波长(EL)为616nm，CIE坐标为(0.65，0.34)。
虽然本发明已以较佳实施例揭露如上，然其并非用以限定本发明，任何熟习此技艺者，在不脱离本发明之精神和范围内，当可作些许之更动与润饰，因此本发明之保护范围当视后附之申请专利范围所界定者为准。
Claims (7)
1.一种有机金属化合物，其系具有如式(I)或式(II)所示之结构：
式(I)
式(II)
其中，
X系为C-H或是N，Y系为CH2或是NH；
R1系氢、或C1-8烷基；以及
A1系乙酰丙酮(acetylacetone)配位基、具有苯环之乙酰丙酮(acetylacetone)配位基、或其衍生物。
2.根据权利要求1所述的有机金属化合物，其中A1之一侧系以氧原子与Ir键合，A1之另一侧系以氧原子与Ir键合。
3.根据权利要求1所述的有机金属化合物，其中R1系包含甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、或己基。
4.根据权利要求2所述的有机金属化合物，其系具有如式(III)、式(IV)、或式(V)所示之结构：
式(III)
式(IV)
式(V)
其中，R1系氢、或C1-8烷基；R2系为氢、苯基(phenyl)、苯基衍生物、或联苯基(biphenyl)；Y系为CH2或是NH。
5.根据权利要求4所述的有机金属化合物，其中该有机金属化合物系为
6.一种有机电致发光装置，包括：
一对电极；以及
有机发光单元，配置于该对电极之间，其中该有机发光单元包含具有式(I)或式(II)所示结构之化合物：
式(I)
式(II)
其中，
X系为C-H或是N，Y系为CH2或是NH；
R1系氢、或C1-8烷基；以及
A1系乙酰丙酮(acetylacetone)配位基、具有苯环之乙酰丙酮(acetylacetone)配位基、或其衍生物。
7.根据权利要求6所述的有机电致发光装置，其中该发光单元系发出红光。
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| TW100127917 | 2011-08-05 | ||
| TW100127917A TWI429652B (zh) | 2011-08-05 | 2011-08-05 | 有機金屬化合物及包含其之有機電激發光裝置 |
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| US (1) | US8871360B2 (zh) |
| JP (1) | JP5544390B2 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9954189B2 (en) | 2014-12-03 | 2018-04-24 | Industrial Technology Research Institute | Organic metal compound and organic light-emitting device employing the same |
| CN109790195A (zh) * | 2016-10-05 | 2019-05-21 | 三菱化学株式会社 | 铱配位化合物以及含有上述化合物的组合物、有机场致发光元件、显示装置和照明装置 |
| CN107501336A (zh) * | 2017-09-12 | 2017-12-22 | 武汉大学 | 一种有机红色磷光铱配合物及其制备方法和在有机电致发光器件中的应用 |
| CN108276452A (zh) * | 2018-03-20 | 2018-07-13 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
| CN113366001A (zh) * | 2019-01-30 | 2021-09-07 | Lt素材株式会社 | 组合物、有机光电装置以及显示装置 |
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| Publication number | Publication date |
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| JP5544390B2 (ja) | 2014-07-09 |
| CN102911212B (zh) | 2015-09-30 |
| JP2013035822A (ja) | 2013-02-21 |
| US20130033172A1 (en) | 2013-02-07 |
| TWI429652B (zh) | 2014-03-11 |
| US8871360B2 (en) | 2014-10-28 |
| TW201307364A (zh) | 2013-02-16 |
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