TWI395804B - 有機金屬化合物及包含其之有機電激發光裝置及組合物 - Google Patents
有機金屬化合物及包含其之有機電激發光裝置及組合物 Download PDFInfo
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- TWI395804B TWI395804B TW099115767A TW99115767A TWI395804B TW I395804 B TWI395804 B TW I395804B TW 099115767 A TW099115767 A TW 099115767A TW 99115767 A TW99115767 A TW 99115767A TW I395804 B TWI395804 B TW I395804B
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- Prior art keywords
- electroluminescent device
- organic electroluminescent
- compound
- organic
- organometallic compound
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 17
- 238000005401 electroluminescence Methods 0.000 title 1
- 150000002736 metal compounds Chemical class 0.000 title 1
- 239000000463 material Substances 0.000 claims description 31
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- 238000000034 method Methods 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
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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 claims description 3
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- 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 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- -1 hydrazine hydrate compound Chemical class 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
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- 238000004528 spin coating Methods 0.000 description 8
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 7
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- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 5
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- 238000003786 synthesis reaction Methods 0.000 description 4
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 229920000144 PEDOT:PSS Polymers 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
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- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 2
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- UEXKIEYHNLJFQH-UHFFFAOYSA-N 4-phenylthieno[3,2-c]pyridine Chemical group N1=CC=C2SC=CC2=C1C1=CC=CC=C1 UEXKIEYHNLJFQH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- 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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
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- 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 1
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- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 1
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- 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
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- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- JYMITAMFTJDTAE-UHFFFAOYSA-N aluminum zinc oxygen(2-) Chemical compound [O-2].[Al+3].[Zn+2] JYMITAMFTJDTAE-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000005684 electric field Effects 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
- 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
- 238000007641 inkjet printing Methods 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 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
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 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
- 238000007740 vapor deposition Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Description
本發明關於一種有機金屬化合物及包含其之有機電激發光裝置，特別關於一種有機金屬磷光化合物及包含其之磷光有機電激發光裝置。
有機電致發光裝置(organic electroluminescent device)，亦稱作有機發光二極體(organic light-emitting diode;OLED)，是以有機層作為主動層的一種發光二極體(LED)。由於有機電致發光裝置具有低電壓操作、高亮度、重量輕、廣視角、以及高對比值等優點，近年來已漸漸使用於平面面板顯示器(flat panel display)上。與液晶顯示器不同，有機電激發光顯示器所包含之有機發光二極體畫素陣列係具有自發光的特性，因此不需外加背光源。
一般而言，有機發光二極體元件包括一對電極，以及在電極之間的一有機發光介質層。發光是導因於以下的現象。當電場施於兩電極時，陰極射出電子到有機發光介質層，陽極射出電洞到有機發光介質層。當電子與電洞在有機發光介質層內結合時，會產生激子(excitons)。電子和電洞的再結合就伴隨著發光。
依據電洞和電子的自旋態(spin state)，由電洞和電子之再結合而產生的激子可具有三重態(triplet)或單重態(singlet)之自旋態。由單重態激子(singlet exciton)所產生的發光為螢光(fluorescence)，而由三重態激子(triplet exciton)所產生的發光為磷光(phosphorescence)。磷光的發光效率是螢光的三倍。因此，發展高效率的磷光材料以增進有機發光二極體元件的發光效率是非常重要的。
目前有機發光二極體元件發光單元材料以小分子材料為主，這是因為小分子有機發光二極體元件不管在效率、亮度與壽命等均較高分子有機發光二極體元件(PLED)高出許多。現今小分子有機發光二極體元件製程不像PLED以旋轉塗佈或是噴墨印刷(Inkjet printing)為主，而是以蒸鍍方式為主。然而，用於蒸鍍方式所使用之真空製程設備成本較高，此外只有5%的有機發光材料會鍍在基板上，95%的有機發光材料浪費在腔體壁上，使得有機發光二極體元件的製造成本居高不下。因此，濕式製程(包含旋轉塗佈(spin coating)、或刮刀塗佈(blade coating))被提出用於小分子有機發光二極體元件的製程上，來降低設備成本及大大提升有機發光材料的使用率。
不過，傳統有機磷光發光材料由於溶解度差的關係，並不適合濕式製程。因此，開發出適用於濕式製程的可溶性有機磷光發光材料是最為關鍵的材料(尤其是作為橘黃光摻雜劑)，對於有機發光二極體技術而，是一個很重要的課題。
本發明提出一種有機金屬化合物，係將烷基或環烷基導入4-phenylthieno[3,2-c]pyridine結構，使材料具有好的溶解度。將短碳鏈(短烷基，例如甲基、或乙基)導入本發明所述之有機金屬化合物結構中，所得之有機金屬化合物可以使用蒸鍍與濕式製程來形成有機發光二極體元件；若將長碳鏈(長烷基，例如第三丁基、或環己烷)導入本發明所述之有機金屬化合物結構中，所得之有機金屬化合物可以使用濕式製程來形成有機發光二極體元件。此外，本發明所述之有機金屬化合物，可應用在有機電激發光裝置，作為發光單元的材料，提升有機電激發光裝置的元件效率。
根據本發明一較佳實施例，該有機金屬化合物，具有如公式(I)或(II)所示之化學結構：
(II)，其中，R係為烷基、或環烷基。
根據本發明另一較佳實施例，本發明係提供一種有機電激發光裝置，該裝置包含一對電極；以及一發光單元，配置於該對電極之間，其中該發光單元包含上述之有機金屬化合物，可作為橘黃光磷光摻雜材料。
根據本發明又一較佳實施例，本發明係提供一種組合物，包括：一有機發光二極體主體材料；以及，上述之有機金屬化合物，均勻的分散於一有機溶劑中。該有機發光二極體主體材料可例如為高分子材料(像是：PVK(poly(vinylcarbazole)))，且該組合物可進一步包含一種以上的載子促進劑(carrier promoter)，例如電子促進劑(像是：PBD(2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole))或電洞促進劑(像是：TPD(N,N’-diphenyl-N,N’-(bis(3-methylphenyl)-[1,1-biphenyl]-4,4’diamine)))。
以下藉由數個實施例及比較實施例，以更進一步說明本發明之方法、特徵及優點，但並非用來限制本發明之範圍，本發明之範圍應以所附之申請專利範圍為準。
有機金屬化合物
本發明係揭露一種有機金屬化合物，係為具有公式(I)或(II)所示之結構：
其中，其中，R係為烷基、或環烷基。舉例來說，R可為C1-12
烷基、或C4-12
環烷基，像是甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、異戊基、環戊基、己基、環己基、庚基、辛基、壬基、癸基、十一烷基、或十二烷基。
以下藉由下列實施例來說明本發明所述之有機金屬化合物的合成方式，用以進一步闡明本發明之技術特徵。
實施例1
化合物PO-01-M之合成
將市售之化合物1(2-(2-aminoethyl)thiophene,7.0g,55.1mmole)放入500mL單頸瓶中，加入200mL H2
O並接上加料漏斗。接著在加料漏斗中加入市售化合物2(p-toluoyl chloride,11.0mL,82.7mmole)，於冰水浴環境下滴入反應瓶中，逐漸產生白色固體。滴完後，加入20% NaOH水溶液，攪拌隔夜。以白瓷漏斗過濾，可得化合物3(白色固體產物)，產率為93%)。上述反應之反應式如下所示：
接著，將化合物3(5.0g,20.4mmole)放入250mL單頸圓底瓶中，加入甲苯(toluene,80mL)。冰水浴下，經由加料漏斗將POCl3
(5.7mL,61.2mmole)滴入反應瓶中。滴完後，移除冰水浴，改以油浴加熱至甲苯迴流，反應2小時後，以飽和碳酸氫鈉(NaHCO3
)水溶液中和反應，再以甲苯萃取。收集甲苯溶液，以無水硫酸鎂除水，減壓濃縮抽乾後，靜置數小時，可得結晶產物(化合物4)，產率為50%。上述反應之反應式如下所示：
接著，將化合物4(3.0g,13.2mmole)和10% Pd/C(3.0g)放入250mL單頸圓底瓶中，加入甲苯(100mL)，加熱至甲苯迴流。反應18小時後，以矽藻土(Celite 545)將Pd/C濾掉，濾液以減壓濃縮機抽乾，可得產物5，產率為85%。上述反應之反應式如下所示：
接著，將化合物5(5.0g,22.2mmole)和水合氣化銥化合物(IrCl3
.xH2
O,3.0g,10mmole)放入100mL單頸圓底瓶中，分別加入2-methoxy ethanol(15mL)和水(5mL)，加熱至140℃。反應24小時後，加入大量的水，過濾，可得橘色固體產物(化合物6)，產率為49%。上述反應之反應式如下所示：
將化合物6(3.3g,4.0mmole)、acac(acetyl acetone,1.65g,16mmole)和碳酸鈉固體(Na2
CO3
,1.71g 16mmole)放入100mL單頸圓底瓶中，加入2-methoxy ethanol(40mL)，加熱至迴流。反應24小時後，待回溫至室溫，加入40mL水，攪拌數小時將固體打散。過濾，將固體以管柱層析法分離純化(以純二氯甲烷為沖提液)，可得橘色粉末產物PO-01-M，產率為50%。上述反應之反應式如下所示：
利用核磁共振光譜分析化合物PO-01-M，所得之光譜資訊如下：1
H NMR(CDCl3
,200MHz)δ8.41(d,J=3.4Hz,2H),8.34(d,J=5.6Hz,2H),8.02(d,J=8.0Hz,2H),7.66(d,J=5.6Hz,2H),7.60(d,J=6.2Hz,2H),6.69(d,J=7.6Hz,2H),6.15(s,2H),5.18(s,1H),2.03(s,6H),1.75(s,6H).
實施例2
化合物PO-01-TB之合成
將化合物1(2-(2-aminoethyl)thiophene,7.0g,55.1mmole)放入500mL單頸瓶中，加入200mL H2O並接上加料漏斗。接著在加料漏斗中加入市售化合物7(4-t-butyl benzoyl chloride,16.2g,82.5mmole)，於冰水浴環境下滴入反應瓶中，逐漸產生白色固體。滴完後，加入20% NaOH水溶液，攪拌隔夜。以白瓷漏斗過濾，可得白色固體產物(化合物8、15.4g)，產率為98%。上述反應之反應式如下所示：
接著，將化合物8(2.87g,10mmole)放入250mL單頸圓底瓶中，加入甲苯(toluene,80mL)。冰水浴下，經由加料漏斗將POCl3
(2.8mL,30mmole)滴入反應瓶中。滴完後，移除冰水浴，改以油浴加熱至甲苯迴流，反應2小時後，以飽和碳酸氫鈉(NaHCO3
)水溶液中和反應，再以甲苯萃取。收集甲苯溶液，以無水硫酸鎂除水，減壓濃縮抽乾後，靜置數小時，可得結晶產物(化合物9、1.6g)，產率為60%。上述反應之反應式如下所示：
將化合物9(2.7g,10mmole)和10% Pd/C(0.5g)放入250mL單頸圓底瓶中，加入甲苯(100mL)，加熱至甲苯迴流。反應18小時後，以矽藻土(Celite 545)將Pd/C濾掉，濾液以減壓濃縮機抽乾，再以管柱層析法分離純化(乙酸乙酯/正己烷=1/9)，可得化合物10，產率為79%。上述反應之反應式如下所示：
將化合物10(5.0g,18.7mmole)和水合氯化銥化合物(IrCl3
.xH2
O,2.9g,8.5mmole)放入100mL單頸圓底瓶中，分別加入2-methoxy ethanol(15mL)和水(5mL)，加熱至140℃。反應24小時後，加入大量的水，過濾，可得橘色固體產物(化合物11、4.1g)，產率為49%。上述反應之反應式如下所示：
將化合物11(1.48g,1.5mmole)、acac(acetyl acetone,0.6g,6mmole)和碳酸鈉固體(Na2
CO3
,0.64g,6mmole)放入100mL單頸圓底瓶中，加入2-methoxy ethanol(15mL)，加熱至迴流。反應24小時後，待回溫至室溫，加入40mL水，攪拌數小時將固體打散。過濾，將固體以管柱層析法分離純化(以純二氯甲烷為沖提液)，可得橘色粉末產物，PO-01-TB，產率為89%。上述反應之反應式如下所示：
利用核磁共振光譜分析化合物PO-01-M，所得之光譜資訊如下：1
H NMR(CDCl3
,200MHz)δ8.45(d,J=6.6Hz,2H),8.30(d,J=5.4Hz,2H),7.99(d,J=8.4Hz,2H),7.64(d,J=5.0Hz,4H),6.88(dd,J=8.6,1.8Hz,2H),6.22(d,J=1.8Hz,2H),5.22(s,1H),1.79(s,6H),0.98(s,18H).
實施例3
化合物PO-01-HEX之合成
將化合物1(2-(2-aminoethyl)thiophene,9.4g,74.1mmole)放入500mL單頸瓶中，加入200mL H2
O並接上加料漏斗。接著在加料漏斗中加入市售化合物12(4-n-hexyl benzoyl chloride,25.0g,111.2mmole)，於冰水浴環境下滴入反應瓶中，逐漸產生白色固體。滴完後，加入20% NaOH水溶液，攪拌隔夜。以白瓷漏斗過濾，可得白色固體產物(化合物13、20.6g)，產率為88%。上述反應之反應式如下所示：
將化合物13(5.0g,15.9mmole)放入250mL單頸圓底瓶中，加入甲苯(toluene,80mL)。冰水浴下，經由加料漏斗將POCl3
(4.4mL,47.6mmole)滴入反應瓶中。滴完後，移除冰水浴，改以油浴加熱至甲苯迴流，反應2小時後，以飽和碳酸氫鈉(NaHCO3
)水溶液中和反應，再以甲苯萃取。收集甲苯溶液，以無水硫酸鎂除水，減壓濃縮抽乾後，靜置數小時，可得結晶產物(化合物14、2.6g)，產率為55%。上述反應之反應式如下所示：
將化合物14(3.0g,13.2mmole)和10% Pd/C(3.0g)放入250mL單頸圓底瓶中，加入甲苯(100mL)，加熱至甲苯迴流。反應18小時後，以矽藻土(Celite 545)將Pd/C濾掉，濾液以減壓濃縮機抽乾，再以管柱層析法分離純化(乙酸乙酯/正己烷=1/9)，可得化合物15，產率為75%。上述反應之反應式如下所示：
將化合物15(3.8g,12.88mmole)和水合氣化銥化合物(IrCl3
.xH2
O,1.7g,5.85mmole)放入100mL單頸圓底瓶中，分別加入2-methoxy ethanol(15mL)和水(5mL)，加熱至140℃。反應24小時後，加入大量的水，過濾，可得橘色固體產物(化合物16)，產率為40%。上述反應之反應式如下所示：
將化合物16(5.0g,4.0mmole)、acac(acetyl acetone,1.23g,12.26mmole)和碳酸鈉固體(Na2
CO3
,1.30g,12.26mmole)放入100mL單頸圓底瓶中，加入2-methoxy ethanol(30mL)，加熱至迴流。反應24小時後，待回溫至室溫，加入40mL水，攪拌數小時將固體打散。過濾，將固體以管柱層析法分離純化(以二氯甲烷/正己烷=1/3為沖提液)，可得橘色粉末產物(PO-01-HEX)，產率為63%。上述反應之反應式如下所示：
利用核磁共振光譜分析化合物PO-01-M，所得之光譜資訊如下：1
H NMR(CDCl3
,200MHz)δ8.42(d,J=3.4Hz,2H),8.32(d,J=5.0Hz,2H),8.01(d,J=5.0Hz,2H),7.65(d,J=5.4Hz,2H),7.42(d,J=4.8Hz,2H),6.69(d,J=7.6Hz,2H),6.10(s,2H),5.19(s,1H),2.26(t,J=6.6Hz,4H),1.76(s,6H),1.55(s,4H),1.10(br,12H),0.80(t,J=7.2Hz,6H).
實施例4
溶解度測試
分別將實施例2-3所得之PO-01-TB與PO-01-HEX材料，以及PO-01(結構為，作為對照組)，以0.5%、0.8%、1%、1.5%、2%、及3%(材料與溶劑的重量比)的比但溶於chlorobenzene中，進行溶解度的測試。結果如表1所示：
由表1可知，藉由將烷基或環烷基導入4-phenylthieno[3,2-c]pyridine結構所得之PO-01-TB和PO-01-HEX材料，具有好的溶解度，於chlorobenzene溶劑中，溶解度可達到1.5%或以上，而未經改質的PO-01只有0.5%。
有機電激發光裝置
請參照第1圖，係顯示一符合本發明所述之有機電激發光裝置10之剖面結構示意圖，該有機電激發光裝置10包括一基底12、一下電極14、一發光單元16及一上電極18。該有機電激發光裝置10可為上發光、下發光、或雙面發光有機電激發光裝置。該基底可例如為玻璃、塑膠基板、或半導體基板。該下電極14及上電極18之材質可例如為鋰、鎂、鈣、鋁、銀、銦、金、鎢、鎳、鉑、銅、銦錫氧化物(ITO)、銦鋅氧化物(IZO)、鋅鋁氧化物(AZO)、氧化鋅(ZnO)或其結合，而其形成方式可為熱蒸鍍、濺射或電漿強化式化學氣相沉積方式。此外，該下電極14及上電極18至少一者需具有透光的性質。
該發光單元16至少包含一發光層，可更包含一電洞注入層、一電洞傳輸層、一電子傳輸層、一電子注入層或其他膜層。值得注意的是，根據本發明較佳實施例，該發光單元16必需包含本發明所述具有公式(I)之有機金屬化合物。換言之，在該發光單元16中，至少有一膜層包含該有機金屬化合物。
根據本發明另一較佳實施例，該有機電激發光裝置可為一磷光有機電激發光裝置，而該磷光發光單元之發光單元包含一主體(host)材料及一磷光摻雜材料，而該磷光摻雜材料材料包含本發明所述具有公式(I)或(II)所示結構之有機金屬化合物。熟悉本技術者可視所使用之有機電激發光材料及所需之元件特性，將本發明所述之有機金屬化合物與所需的磷光摻雜材料摻雜，並改變所搭配的摻雜物之摻雜量。因此，摻雜物之摻雜量之多寡非關本發明之特徵，非為限制本發明範圍之依據。
為進一步說明本發明有機電激發光裝置，以下實施例係將由實施例1-3所得之有機金屬化合物作為摻雜材料，提供數個有機電激發光裝置的實施例(分別以蒸鍍(乾式製程)或塗佈(溼式製程)方式來形成)，來與比較實施例進行比對(以PO-01作為摻雜物)，來驗證本發明所述之有機金屬化合物具有與習知材料相確實具有較高的光電特性。
乾式製程
比較實施例1:
使用中性清潔劑、丙酮、及乙醇以超音波振盪將已製作圖樣的ITO(厚度為120nm)玻璃基底洗淨。以氮氣將基材吹乾，然後UV-OZONE 30分鐘，接著於10-6
torr的壓力下依序沉積NPB(N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine、厚度為30nm)、CBP(4,4'-N,N'-dicarbazole-biphenyl)摻雜PO-01()(CBP與PO-01的比例為100:6、厚度為30nm)、BCP(2,9-dimethyl-4,7diphenyl-1,10-phenanthroline、厚度為10nm)、Alq3
(tris(8-hydroxyquinoline) aluminum、厚度為20nm)、LiF(厚度為0.5nm)、及Al(厚度為120nm)，封裝後獲致該電激發光裝置(1)。該電激發光裝置(1)之結構可表示為：ITO/NPB/CBP: PO-01(6%)/BCP/Alq3
/LiF/Al。
接著，量測該電激發光裝置(1)之光學特性，其量測結果請參照表2。
實施例5：
使用中性清潔劑、丙酮、及乙醇以超音波振盪將已製作圖樣的ITO(厚度為120nm)玻璃基底洗淨。以氮氣將基材吹乾，然後UV-OZONE 30分鐘，接著於10-6
torr的壓力下依序沉積NPB(N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine、厚度為30nm)、CBP(4,4'-N,N'-dicarbazole-biphenyl)摻雜PO-01-TB(CBP與PO-01-TB的比例為100:6、厚度為30nm)、BCP(2,9-dimethyl-4,7diphenyl-1,10-phenanthroline、厚度為10nm)、Alq3
(tris(8-hydroxyquinoline)aluminum、厚度為20nm)、LiF(厚度為0.5nm)、及Al(厚度為120nm)，封裝後獲致該電激發光裝置(2)。該電激發光裝置(2)之結構可表示為：ITO/NPB/CBP: PO-01-TB(6%)/BCP/Alq3
/LiF/Al。
接著，量測該電激發光裝置(2)之光學特性，其量測結果請參照表2。
如表2所示，在搭配相同主體材料的條件下，本發明所述之有機金屬化合物PO-01-TB與PO-01相比，可降低驅動電壓且有比較好的元件效率。
溼式製程
比較實施例2：
使用中性清潔劑、丙酮、及乙醇以超音波振盪將已製作圖樣的ITO(厚度為120nm)玻璃基底洗淨。以氮氣將基材吹乾，然後UV-OZONE 30分鐘。接著，選用PEDOT(poly(3,4)-ethylendioxythiophen):PSS(e-polystyre nesulfonate)當作電洞注入層(hole-inject layer)，以刮刀及旋轉塗佈方式(轉速4000rpm)形成膜層(厚度為50nm)，然後加熱100℃持續40分鐘。接著，在PEDOT:PSS層上以刮刀塗佈方式形成TFB(poly[99,9-dioctylfluorenyl-2,7-diyl)-co-(4,4’-(N-(4-s-butylphenyl))diphenylamine)])層(厚度為20nm)，然後在真空下加熱到180℃持續40分鐘，TFB係當作電洞傳遞層(hole-transport layer)材料。接著，在TFB層上以塗佈方式形成一發光層(厚度約為30nm)，用來形成發光層的塗佈組合物包含：PVK(poly(vinylcarbazole))、PBD(2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole)、TPD(N,N’-diphenyl-N,N’-(bis(3-methylphenyl)-[1,1-biphenyl]-4,4’diamine))、及PO-01，重量比例(PVK:PBD:TPD:PO-01為(55:34:9:6)，溶於chlorobenzene溶劑中。接著，在發光層上以刮刀及旋轉塗佈方式形成電洞阻隔兼電子傳輸層(hole-block/electron-transport layer)TPBI(1,3,5-tris(phenyl-2-benzimidazolyl)-benzene)，厚度約為20nm。接著，沉積LiF(厚度為0.5nm)、及Al(厚度為120nm)，封裝後獲致該電激發光裝置(3)。該電激發光裝置(3)之結構可表示為：ITO/PEDOT(CH8000)/TFB/PVK:PBD:TPD:PO-01/TPBI/LiF/Al。
接著，量測該電激發光裝置(3)之光學特性，其量測結果請參照表3。
實施例6:
使用中性清潔劑、丙酮、及乙醇以超音波振盪將已製作圖樣的ITO(厚度為120nm)玻璃基底洗淨。以氮氣將基材吹乾，然後UV-OZONE 30分鐘。接著，選用PEDOT(poly(3,4)-ethylendioxythiophen):PSS(e-polystyre nesulfonate)當作電洞注入層(hole-inject layer)，以刮刀及旋轉塗佈方式(轉速4000rpm)形成膜層(厚度為50nm)，然後加熱100℃持續40分鐘。接著，在PEDOT:PSS層上以刮刀塗佈方式形成TFB(poly[99,9-dioctylfluorenyl-2,7-diyl)-co-(4,4’-(N-(4-s-butylphenyl))diphenylamine)])層(厚度為20nm)，然後在真空下加熱到180℃持續40分鐘，TFB係當作電洞傳遞層(hole-transport layer)材料。接著，在TFB層上以塗佈方式形成一發光層(厚度約為30nm)，用來形成發光層的塗佈組合物包含：PVK(poly(vinylcarbazole))、PBD(2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole)、TPD(N,N’-diphenyl-N,N’-(bis(3-methylphenyl)-[1,1-biphenyl]-4,4’diamine))、及PO-01-TB，重量比例(PVK:PBD:TPD:PO-01-TB為(61:24:9:6)，溶於chlorobenzene溶劑中。接著，在發光層上以刮刀及旋轉塗佈方式形成電洞阻隔兼電子傳輸層(hole-block/electron-transport layer)TPBI(1,3,5-tris(phenyl-2-benzimidazolyl)-benzene)，厚度約為20nm。接著，沉積LiF(厚度為0.5nm)、及Al(厚度為120nm)，封裝後獲致該電激發光裝置(4)。該電激發光裝置(4)之結構可表示為：ITO/PEDOT(CH8000)/TFB/PVK:PBD:TPD:PO-01-TB/TP BI/LiF/Al。
接著，量測該電激發光裝置(4)之光學特性，其量測結果請參照表3。
實施例7:
使用中性清潔劑、丙酮、及乙醇以超音波振盪將已製作圖樣的ITO(厚度為120nm)玻璃基底洗淨。以氮氣將基材吹乾，然後UV-OZONE 30分鐘。接著，選用PEDOT(poly(3,4)-ethylendioxythiophen):PSS(e-polystyre nesulfonate)當作電洞注入層(hole-inject layer)，以刮刀及旋轉塗佈方式(轉速4000rpm)形成膜層(厚度為50nm)，然後加熱100℃持續40分鐘。接著，在PEDOT:PSS層上以刮刀塗佈方式形成TFB(poly[99,9-dioctylfluorenyl-2,7-diyl)-co-(4,4’-(N-(4-s-butylphenyl))diphenylamine)])層(厚度為20nm)，然後在真空下加熱到180℃持續40分鐘，TFB係當作電洞傳遞層(hole-transport layer)材料。接著，在TFB層上以塗佈方式形成一發光層(厚度約為30nm)，用來形成發光層的塗佈組合物包含：PVK(poly(vinylcarbazole))、PBD(2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole)、TPD(N,N’-diphenyl-N,N’-(bis(3-methylphenyl)-[1,1-biphenyl]-4,4’diamine))、及PO-01-HEX，重量比例(PVK:PBD:TPD:PO-01-HEX為(61:24:9:6)，溶於chlorobenzene溶劑中。接著，在發光層上以刮刀及旋轉塗佈方式形成電洞阻隔兼電子傳輸層(hole-block/electron-transport layer)TPBI(1,3,5-tris(phenyl-2-benzimidazolyl)-benzene)，厚度約為20nm。接著，沉積LiF(厚度為0.5nm)、及Al(厚度為120nm)，封裝後獲致該電激發光裝置(5)。該電激發光裝置(5)之結構可表示為：ITO/PEDOT(CH8000)/TFB/PVK:PBD:TPD:PO-01-HEX/T PBI/LiF/Al。
接著，量測該電激發光裝置(5)之光學特性，其量測結果請參照表3。
如表3所示，在搭配相同主體材料的條件下，改質後的PO-01-TB和PO-01-HEX由於具有較佳的溶解度，所以所得之濕式製程元件效率較PO-01分別高出12倍和7倍以上。
雖然本發明已以較佳實施例揭露如上，然其並非用以限定本發明，任何熟習此技藝者，在不脫離本發明之精神和範圍內，當可作些許之更動與潤飾，因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。
10．．．有機電激發光裝置
12．．．基底
14．．．下電極
16．．．發光單元
以及
18．．．上電極
第1圖係為本發明一較佳實施例所述之有機電激發光裝置的剖面結構圖。
10．．．有機電激發光裝置
12．．．基底
14．．．下電極
16．．．發光單元
18．．．上電極
Claims (10)
- 一種有機金屬化合物，其係具有如公式(I)或公式(II)所示之化學式：
- 如申請專利範圍第1項所述之有機金屬化合物，其中該R係為C1-12 烷基、或C4-12 環烷基。
- 如申請專利範圍第1項所述之有機金屬化合物，其中該R係為甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、異戊基、環戊基、己基、環己基、庚基、辛基、壬基、癸基、十一烷基、或十二烷基。
- 一種有機電激發光裝置，包括：一對電極；以及一發光單元，配置於該對電極之間，其中，該發光單元包含具有公式(I)或(II)所示結構之有機金屬化合物：
- 如申請專利範圍第4項所述之有機電激發光裝置，其中該R係為C1-12 烷基、或C4-12 環烷基。
- 如申請專利範圍第4項所述之有機電激發光裝置，其中該R係為甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、異戊基、環戊基、己基、環己基、庚基、辛基、壬基、癸基、十一烷基、或十二烷基。
- 如申請專利範圍第4項所述之有機電激發光裝置，其中該發光單元係以蒸鍍方式所製備而得。
- 如申請專利範圍第4項所述之有機電激發光裝置，其中該發光單元係以溼式製程方式所製備而得。
- 如申請專利範圍第4項所述之有機電激發光裝置，其中該發光單元係發出橘黃光。
- 一種組合物，包括：一有機發光二極體主體材料；以及一有機金屬化合物，其係具有如公式(I)或公式(II)所示之化學式：
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| US20110285275A1 (en) | 2011-11-24 |
| TW201141987A (en) | 2011-12-01 |
| US8722207B2 (en) | 2014-05-13 |
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