JPWO2010098246A1 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- JPWO2010098246A1 JPWO2010098246A1 JP2011501562A JP2011501562A JPWO2010098246A1 JP WO2010098246 A1 JPWO2010098246 A1 JP WO2010098246A1 JP 2011501562 A JP2011501562 A JP 2011501562A JP 2011501562 A JP2011501562 A JP 2011501562A JP WO2010098246 A1 JPWO2010098246 A1 JP WO2010098246A1
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- 238000005401 electroluminescence Methods 0.000 title claims description 11
- 239000000463 material Substances 0.000 claims abstract description 199
- 239000002019 doping agent Substances 0.000 claims abstract description 18
- 239000010410 layer Substances 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 230000015572 biosynthetic process Effects 0.000 claims description 25
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 23
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 15
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 5
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- 238000002347 injection Methods 0.000 abstract description 11
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- 125000004432 carbon atom Chemical group C* 0.000 description 25
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 8
- 238000003775 Density Functional Theory Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 239000000243 solution Substances 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- 150000001491 aromatic compounds Chemical class 0.000 description 6
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- 239000010409 thin film Substances 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
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- 238000007606 doctor blade method Methods 0.000 description 5
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- 239000000706 filtrate Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- FQKSBRCHLNOAGY-UHFFFAOYSA-N indolo[2,3-a]carbazole Chemical compound C1=CC=C2N=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 FQKSBRCHLNOAGY-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
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- 238000005457 optimization Methods 0.000 description 5
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
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- 239000012043 crude product Substances 0.000 description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
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- 239000000741 silica gel Substances 0.000 description 4
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 4
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
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- 238000004057 DFT-B3LYP calculation Methods 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000005137 deposition process Methods 0.000 description 3
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
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- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
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- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 1
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- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/18—Light sources with substantially two-dimensional radiating surfaces characterised by the nature or concentration of the activator
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/135—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising mobile ions
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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Abstract
Description
式(1)中、環Aは隣接環と任意の位置で縮合する式(1a)で表される芳香環を表し、環Bは隣接環と任意の位置で縮合する式(1b)で表される複素環を表す。式(1)、(1a)中のRは、独立に水素又は1価の置換基であり、隣接する置換基が一体となって環を形成してもよい。式(1b)中のL1は、独立に芳香族炭化水素基又は芳香族複素環基を示す。Lは、n価の芳香族炭化水素基又は芳香族複素環基を示し、nは1〜4である。nが2以上の場合は、環A、Bを含む縮合複素環は同一であっても異なっていても良い。
基板1としては、一般的な有機電界発光素子で使われる基板であれば特に制限はないが、透明性、表面の平滑性、取扱の容易性及び防水性に優れた有機基板又は透明プラスチック基板、ガラス基板を用いることが好ましい。
なお、以下の合成例1〜5で使用するインドロ[2,3−a]カルバゾール、2−クロロ−4,6−ジフェニル−1,3,5−トリアジン、及び実施例1の化合物2−1については、WO08―056746号公報に記載の方法に従い合成した。また、化合物3−1については、WO07―063754号公報に記載の方法に従い合成した。
化合物2−9の合成
脱気窒素置換した1L四ッ口フラスコに、インドロ[2,3−a]カルバゾール28.53g(111.4mmol)、炭酸カリウム21.56g(156.02mmol)、銅粉末35.41g(557.21mmol)、1−ブロモ−3,5−ジ−t−ブチルベンゼン30.00g(111.4mmol)、テトラエチレングリコールジメチルエーテル450gを入れ、内温205℃で24時間攪拌した。室温まで冷却後、ろ過助剤を用いて固形分をろ別し、ろ液を減圧下濃縮した。次いで、シリカゲルカラムにて分画・精製し、白色固体7.42gを得た。この白色固体のFD−MSスペクトルは、445(MH+、base)であった。
化合物2−10の合成
脱気窒素置換した500mL三ッ口フラスコに、インドロ[2,3−a]カルバゾール9.84g(38.4mmol)、炭酸カリウム15.94g(115.33mmol)、銅粉末12.22g(192.22mmol)、4−t−ブチルヨードベンゼン10.00g(38.4mmol)、1,3−ジメチル−2−イミダゾリジノン150gを入れ、内温205℃で20時間攪拌した。室温まで冷却後、ろ過助剤を用いて固形分をろ別し、ろ液を減圧下濃縮した。ろ液を分液ロートに移し、酢酸エチル700ml、10%塩酸を加えて、0.5時間静置し、下層を廃棄した。上層を蒸留水、飽和食塩水で洗浄、硫酸マグネシウムで乾燥後、溶媒を減圧留去し、褐色固体を得た。シリカゲルカラムにて精製後、ジクロロメタン−エタノールで再結晶を行い、白色結晶6.30gを得た。この白色固体のFD−MSスペクトルは、389(MH+、base)であった。
化合物3−4の合成
脱気窒素置換した1L四ツ口フラスコに、インドロ[2,3−a]カルバゾール45.0g(0.176mol)、炭酸カリウム72.9g(0.527mol)、銅粉末55.9g(0.879mol)、1,3−ジヨードベンゼン29.0g(0.088mol)、テトラエチレングリコールジメチルエーテル638gを入れ、内温205℃で18時間攪拌した。室温まで冷却後、ろ過助剤を用いて固形分をろ別した。得られたろ液を分液ロートに移し、10重量%塩酸1400gを加えた後、酢酸エチル2100gで抽出した。酢酸エチル層を蒸留水、飽和食塩水で順に洗浄した後、硫酸マグネシウムで乾燥、吸水した硫酸マグネシウムを吸引ろ過で除去後、溶媒を減圧留去した。残渣をジクロロメタンリスラリー、トルエンリスラリーを順に行い、減圧下80℃で乾燥し、白色固体29.08gを得た。この白色固体のFD−MSスペクトルは、587(MH+、base)であった。
化合物3−9の合成
脱気窒素置換した2L四ッ口フラスコに、1,3−ジヨードベンゼン36.96g(0.112mol)、3−ブロモフェニルボロン酸45.00g(0.224mol)、テトラキス(トリフェニルホスフィン)パラジウム(0)4.27g(3.7mmol)、エタノール225ml、トルエン603mlを入れ、室温で攪拌した。この溶液に、炭酸ナトリウム142.2g(1.342mol)、蒸留水297gを装入し、内温75℃にて19時間攪拌した。室温まで冷却し、水層を抜き出した後、有機層を飽和食塩水で洗浄し、硫酸マグネシウムで乾燥、吸水した硫酸マグネシウムを吸引ろ過で除去後、溶媒を減圧留去した。シリカゲルカラムにて精製し、茶色油状物42.13gを得た。これを0.2kPaの減圧下にて蒸留精製し、留出温度220〜234℃を分画し、無色油状物21.55gを得た。FD−MSスペクトルにて、386、388、390(M+、base、1:2:1強度比)のピークが観測され、1,3−ビス(3−ブロモフェニル)ベンゼンであることを確認した。
化合物3−14の合成
WO07―063754号公報記載の化合物3−1の合成方法において、フェニルボロン酸を(3,5−ジフェニル)フェニルボロン酸に変更した以外は同様にして、化合物3−14を合成した。FD−MSスペクトルを測定したところ、970(M+、base)のピークが観測され、化合物3−14であることを確認した。
化合物Aの合成
特開2005−239703号公報に記載の方法と同様にして、化合物Aを合成した。FD−MSスペクトルを測定したところ、524(M+、base)のピークが観測され、化合物Aであることを確認した。
化合物Cの合成
WO07―063754号公報記載の化合物3−1の合成方法において、フェニルボロン酸をピレンー2-イルボロン酸に変更した以外は同様にして、化合物Cを合成した。FD−MSスペクトルを測定したところ、941(M+、base)のピークが観測され、化合物Cであることを確認した。
前述の合成例で得た化合物2−9、2−10、3−4、3−9、3−14、化合物2−1、3−1、及び化合物A、B、Cについて、IP、EA及びT1値を算出した。
IP、EA、T1値は、分子軌道法プログラムGaussian03rev.C02を使用して、密度汎関数理論(DFT)法を用いた構造最適化計算により計算した。IP値、EA値は、B3LYP/6-31G*レベルの構造最適化計算を行うことにより計算されたHOMOエネルギー、LUMOエネルギーの符号をかえた値(eV単位換算値)とした。T1値は、B3LYP/6-31G*レベルの構造最適化計算を行った後、最適化された構造を基にTD-B3LYP/6-31G*レベルで励起3重項の最も低い励起エネルギーを算出した。各化合物の計算値は、表1に示した。
図1において正孔輸送層を省略し、電子注入層を追加した構成の有機EL素子を作製した。UVオゾン洗浄及び乾燥工程を経た膜厚150nmのITOからなる陽極が形成されたガラス基板上に、正孔注入層として、PEDOT・PSS(Baytron P CH8000)の20重量%エタノール溶液を、回転数3000rpmで60秒間スピンコート製膜し、200℃で60分間乾燥した。このときの膜厚は25nmであった。次に、発光層として、ホスト材料が化合物2−1(38.0重量部)、燐光ドーパント材料がトリス(2−フェニルピリジン)イリジウム(Ir(ppy)3)(2.0重量部)、ジクロロメタン(2840重量部)の混合溶液を、回転数4000rpmで30秒間スピンコート製膜し、120℃にて30分間乾燥した。このときの発光層の膜厚は70nmであった。次に、電子輸送層として、トリス(8−ヒドロキシキノリン)アルミニウム(Alq3)を真空蒸着法にて、蒸着レート0.1nm/secにて35nmの厚さで製膜した。更に電子注入層として、真空蒸着法にてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に電子注入層上に電極として、真空蒸着法にてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作製した。
ホスト材料として、第一のホスト材料と第二のホスト材料を使用し、第一のホスト材料として化合物2−1(17.3重量部)と第二のホスト材料として化合物2−9(20.7重量部)を使用し、70nm膜厚の発光層を得た以外は、実施例1と同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2−1(18.0重量部)と第二のホスト材料が化合物2−10(20.0重量部)を使用し、70nm膜厚の発光層を得た以外は、同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2−1(13.3重量部)と第二のホスト材料として化合物3−4(24.7重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2−1(12.1重量部)と第二のホスト材料として化合物3−9(25.9重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2−1(23.6重量部)と第二のホスト材料として化合物3−4(14.4重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2−1(19.7重量部)と第二のホスト材料として化合物A(18.3重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2−1(16.7重量部)と第二のホスト材料として化合物B(21.3重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物2−1(14.2重量部)と第二のホスト材料として化合物C(23.8重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例1において、ホスト材料として化合物3−1を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。電流効率は10.8cd/A、輝度半減期は48hrであった。
実施例2において、第一のホスト材料として化合物3−1(16.6重量部)と第二のホスト材料として化合物3−4(21.4重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3−1(20.8重量部)と第二のホスト材料として化合物2−9(17.2重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3−1(17.4重量部)と第二のホスト材料として化合物3−14(20.6重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3−1(14.8重量部)と第二のホスト材料として化合物A(23.2重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3−1(20.2重量部)と第二のホスト材料として化合物B(17.8重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
実施例2において、第一のホスト材料として化合物3−1(17.7重量部)と第二のホスト材料として化合物C(20.3重量部)を使用し、70nm膜厚の発光層を得た以外は、全て同様の操作を行って有機EL素子を作製し、素子評価を行った。
Claims (7)
- 陽極及び陰極の間にウェットプロセスにより製膜された発光層を有する有機電界発光素子であって、発光層がりん光ドーパント材料と分子量10,000以下のホスト材料を含有し、前記ホスト材料は第一のホスト材料と第一のホスト材料とは異なる第二のホスト材料からなり、第一のホスト材料と第二のホスト材料の重量比が90:10〜10:90であり、第一のホスト材料と第二のホスト材料のイオン化ポテンシャル(IP)値の差が0.1eV以下、かつ電子親和力(EA)値の差が0.1eV以下、かつ三重項エネルギー(T1)値の差が0.1eV以下であることを特徴とする有機電界発光素子。
- 第一のホスト材料又は第二のホスト材料が、インドロカルバゾール誘導体及びトリアジン誘導体からなる群から選ばれる複素環化合物である請求項1に記載の有機電界発光素子。
- 第一のホスト材料と第二のホスト材料が、式(2)又は(3)で表される複素環化合物から選ばれる2種の複素環化合物である請求項4記載の有機電界発光素子。
- 第一のホスト材料と第二のホスト材料の重量比が75:25〜25:75である請求項1に記載の有機電界発光素子。
- 陽極及び陰極の間に発光層を含む有機層を有し、発光層がりん光ドーパント材料と分子量10,000以下のホスト材料を含有する有機電界発光素子の製造方法であって、ホスト材料とりん光ドーパント材料を用意すること、ここで、ホスト材料が、第一のホスト材料と第一のホスト材料とは異なる第二のホスト材料からなり、第一のホスト材料と第二のホスト材料の重量比が90:10〜10:90であり、第一のホスト材料と第二のホスト材料のイオン化ポテンシャル(IP)値の差が0.1eV以下、かつ電子親和力(EA)値の差が0.1eV以下、かつ三重項エネルギー(T1)値の差が0.1eV以下であること、ホスト材料とりん光ドーパント材料を溶媒に溶解して塗液を形成すること、この塗液を発光層に隣接する有機層上に塗布、乾燥して製膜する工程を含むことを特徴とする有機電界発光素子の製造方法。
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US8795852B2 (en) | 2014-08-05 |
WO2010098246A1 (ja) | 2010-09-02 |
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EP2403028B1 (en) | 2014-11-12 |
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EP2403028A1 (en) | 2012-01-04 |
JP5433677B2 (ja) | 2014-03-05 |
TW201100518A (en) | 2011-01-01 |
TWI471404B (zh) | 2015-02-01 |
US20120001158A1 (en) | 2012-01-05 |
CN102326273A (zh) | 2012-01-18 |
KR101596906B1 (ko) | 2016-03-07 |
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