JP6040044B2 - ビピリジン化合物、発光素子用材料、有機半導体材料、発光素子、ディスプレイモジュール、照明モジュール、発光装置、照明装置、表示装置及び電子機器 - Google Patents
ビピリジン化合物、発光素子用材料、有機半導体材料、発光素子、ディスプレイモジュール、照明モジュール、発光装置、照明装置、表示装置及び電子機器 Download PDFInfo
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- JP6040044B2 JP6040044B2 JP2013026256A JP2013026256A JP6040044B2 JP 6040044 B2 JP6040044 B2 JP 6040044B2 JP 2013026256 A JP2013026256 A JP 2013026256A JP 2013026256 A JP2013026256 A JP 2013026256A JP 6040044 B2 JP6040044 B2 JP 6040044B2
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- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- RVHDEFQSXAYURV-UHFFFAOYSA-N n-[4-(9,10-diphenylanthracen-2-yl)phenyl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=C3C(C=4C=CC=CC=4)=C4C=CC=CC4=C(C=4C=CC=CC=4)C3=CC=2)C=C1 RVHDEFQSXAYURV-UHFFFAOYSA-N 0.000 description 1
- KUGSVDXBPQUXKX-UHFFFAOYSA-N n-[9,10-bis(2-phenylphenyl)anthracen-2-yl]-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C(=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 KUGSVDXBPQUXKX-UHFFFAOYSA-N 0.000 description 1
- COVCYOMDZRYBNM-UHFFFAOYSA-N n-naphthalen-1-yl-9-phenyl-n-(9-phenylcarbazol-3-yl)carbazol-3-amine Chemical compound C1=CC=CC=C1N1C2=CC=C(N(C=3C=C4C5=CC=CC=C5N(C=5C=CC=CC=5)C4=CC=3)C=3C4=CC=CC=C4C=CC=3)C=C2C2=CC=CC=C21 COVCYOMDZRYBNM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 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
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- CJGUQZGGEUNPFQ-UHFFFAOYSA-L zinc;2-(1,3-benzothiazol-2-yl)phenolate Chemical compound [Zn+2].[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1.[O-]C1=CC=CC=C1C1=NC2=CC=CC=C2S1 CJGUQZGGEUNPFQ-UHFFFAOYSA-L 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Planar Illumination Modules (AREA)
- Pyridine Compounds (AREA)
Description
本実施の形態では、実施の形態1に記載のビピリジン化合物を有機半導体素子の一種である縦型トランジスタ(SIT)の活性層として用いる形態を例示する。
本実施の形態では実施の形態1に示したビピリジン化合物を用いた発光素子の一態様について図1(A)を用いて以下に説明する。本実施の形態で説明する発光素子では、当該物質をホスト材料、発光材料及び電子輸送材料のいずれか1又は複数に用いていれば良い。
本実施の形態は、複数の発光ユニットを積層した構成の発光素子(以下、積層型素子ともいう)の態様について、図1(B)を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する発光素子である。一つの発光ユニットは、実施の形態3で示した有機化合物を含む層103と同様な構成を有する。つまり、実施の形態3で示した発光素子は、1つの発光ユニットを有する発光素子であり、本実施の形態では、複数の発光ユニットを有する発光素子ということができる。
本実施の形態では、実施の形態1に記載のビピリジン化合物を含む発光素子を用いたディスプレイモジュールについて説明する。
本実施の形態では、実施の形態1に記載のビピリジン化合物を用いた発光素子を照明モジュールに用いる例を図19を参照しながら説明する。図19(B)は照明装置の上面図、図19(A)は図19(B)におけるE−F断面図である。
本実施の形態では、実施の形態3又は実施の形態4に示す発光素子をその一部に含む発光装置、表示装置、照明装置及び電子機器について説明する。実施の形態3又は実施の形態4に記載の発光素子は、実施の形態1に記載のビピリジン化合物を含むことから、消費電力が低減された発光素子であり、その結果、本実施の形態に記載の発光装置、表示装置照明装置及び電子機器は、消費電力が低減された表示部を有する発光装置、表示装置、照明装置及び電子機器とすることが可能である。また、実施の形態3又は実施の形態4に記載の発光素子は、駆動電圧の小さい発光素子であるため、駆動電圧の小さい発光装置、表示装置、照明装置及び電子機器とすることが可能である。
<5,6−ビス[4−(10−フェニル−9−アントリル)フェニル]−2,2’−ビピリジン(略称:PAP2BPy)の合成>
容量100mLの3口フラスコに5,6−ビス(4−ブロモフェニル)−2,2’−ビピリジン0.74g(1.6mmol)、10−フェニルアントラセン−9−ボロン酸1.1g(3.7mmol)、炭酸ナトリウム0.79g(7.4mmol)、トルエン20mL、エタノール5mL、水5mLを加えた。この混合物を減圧下で攪拌する事により脱気し、フラスコ内を窒素置換した。この混合物に、テトラキス(トリフェニルホスフィン)パラジウム(0)74mg(0.14mmol)を加え、窒素気流下、120℃で10時間還流した。所定時間経過後、この混合物に水を加え、水層と有機層とを分離した後、水層からトルエンで有機物を抽出した。得られた抽出溶液と有機層とを合わせ、飽和食塩水で洗浄後、水層と有機層とを分離し、有機層を硫酸マグネシウムで乾燥した。この混合物を自然濾過し、濾液を濃縮して油状物を得た。得られた油状物をシリカゲルカラムクロマトグラフィー(トルエン)で精製し、固体を得た。この固体のメタノール懸濁液に超音波を照射し、固体を吸引濾過により回収した。得られた固体をトルエンにより再結晶したところ、目的物の淡黄色粉末を収量0.56g、収率43%で得た。本反応の合成スキームを以下に示す。
1H NMR(CD2Cl2、300MHz):δ=7.15−7.30(m、8H)、7.39−7.43(m、1H)、7.46−7.68(m、20H)、7.77(t、J=8.4Hz、4H)、7.88−7.96(m、3H)、8.20(d、J=8.4Hz、1H)、8.65(d、J=7.8Hz、1H)、8.73(d、J=8.4Hz、1H)、8.76−8.78(m、1H)
<5,6−ビス[4’−(10−フェニル−9−アントリル)ビフェニル−4−イル]−2,2’−ビピリジン(略称:PAPP2BPy)の合成>
容量50mLの3口フラスコに5,6−ビス(4−ブロモフェニル)−2,2’−ビピリジン0.70g(1.5mmol)、4−(10−フェニル−9−アントリル)フェニルボロン酸1.2g(3.3mmol)、炭酸ナトリウム0.79g(7.5mmol)、トルエン15mL、エタノール5mL、水5mLを加えた。この混合物を減圧下で攪拌する事により脱気し、フラスコ内を窒素置換した。この混合物に、テトラキス(トリフェニルホスフィン)パラジウム(0)80mg(69μmol)を加え、窒素気流下、120度で6時間還流した。所定時間経過後、混合物を室温まで降温し、析出した固体を吸引濾過により回収した。得られた固体をクロロホルムに溶解し、水、飽和食塩水の順で洗浄して、有機層を硫酸マグネシウムで乾燥した。得られた混合物を自然濾過し、濾液を濃縮して固体を得た。この固体のメタノール懸濁液に超音波を照射し、固体を吸引濾過により回収した。得られた固体をトルエンで再結晶したところ、淡黄色粉末を収量1.2g、収率84%で得た。本反応の合成スキームを以下に示す。
1H NMR(CDCl3,300MHz):δ=7.29−7.37(m、9H)、7.46−7.63(m、16H)、7.68−7.80(m、14H)、7.84−7.90(m、5H)、8.00(d、J=7.8Hz、1H)、8.53(d、J=8.4Hz、1H)、8.69(d、J=7.8Hz、1H)、8.75(dd、J=3.9Hz、1.2Hz、1H)
まず、ガラス基板上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極101を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。ここで、第1の電極101は、発光素子の陽極として機能する電極である。
102 第2の電極
103 有機化合物を含む層
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
301 基板
302 第1の電極
304 第2の電極
311 電子輸送層
312 発光層
313 正孔輸送層
314 正孔注入層
400 基板
401 第1の電極
402 補助電極
403 有機化合物を含む層
404 第2の電極
405 シール材
406 シール材
407 封止基板
408 空間
412 パッド
420 ICチップ
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 駆動回路部(ソース側駆動回路)
602 画素部
603 駆動回路部(ゲート側駆動回路)
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 第1の電極
614 絶縁物
616 有機化合物を含む層
617 第2の電極
618 発光素子
623 nチャネル型TFT
624 pチャネル型TFT
901 筐体
902 液晶層
903 バックライトユニット
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 有機化合物を含む層
956 電極
1201 ソース電極
1202 活性層
1203 ドレイン電極
1204 ゲート電極
2001 筐体
2002 光源
3001 照明装置
5000 表示領域
5001 表示領域
5002 表示領域
5003 表示領域
5004 表示領域
5005 表示領域
7101 筐体
7103 表示部
7105 スタンド
7107 表示部
7109 操作キー
7110 リモコン操作機
7201 本体
7202 筐体
7203 表示部
7204 キーボード
7205 外部接続ポート
7206 ポインティングデバイス
7301 筐体
7302 筐体
7303 連結部
7304 表示部
7305 表示部
7306 スピーカ部
7307 記録媒体挿入部
7308 LEDランプ
7309 操作キー
7310 接続端子
7311 センサ
7401 筐体
7402 表示部
7403 操作ボタン
7404 外部接続ポート
7405 スピーカ
7406 マイク
9630 筐体
9631 表示部
9631a 表示部
9631b 表示部
9632a タッチパネル領域
9632b タッチパネル領域
9633 太陽電池
9634 充放電制御回路
9635 バッテリー
9636 DCDCコンバータ
9637 操作キー
9638 コンバータ
9639 キーボード表示切り替えボタン
9033 留め具
9034 表示モード切り替えスイッチ
9035 電源スイッチ
9036 省電力モード切り替えスイッチ
9038 操作スイッチ
Claims (15)
- 下記式(G1)で表されるビピリジン化合物。
(式中、R1乃至R6、R10乃至R17及びR20乃至R27はそれぞれ独立に、水素又は炭素数1乃至4のアルキル基を表す。また、Ar1及びAr2はそれぞれ独立に、炭素数6乃至13のアリーレン基を表す。また、R30及びR40はそれぞれ独立に、水素、炭素数1乃至4のアルキル基及び炭素数6乃至13のアリール基のいずれかを表す。) - 下記式(G2)で表されるビピリジン化合物。
(式中、R10乃至R17及びR20乃至R27はそれぞれ独立に、水素又は炭素数1乃至4のアルキル基を表す。また、Ar1及びAr2はそれぞれ独立に、炭素数6乃至13のアリーレン基を表す。また、R30及びR40はそれぞれ独立に、水素、炭素数1乃至4のアルキル基及び炭素数6乃至13のアリール基のいずれかを表す。) - 下記式(G3)で表されるビピリジン化合物。
(式中、Ar1及びAr2はそれぞれ独立に、炭素数6乃至13のアリーレン基を表す。また、R30及びR40はそれぞれ独立に、水素、炭素数1乃至4のアルキル基及び炭素数6乃至13のアリール基のいずれかを表す。) - 請求項1乃至請求項3のいずれか一項において、
前記Ar 1 及び前記Ar 2 がそれぞれ独立に、置換基を有していてもよいフェニレン基、又は、置換基を有していてもよいビフェニルジイル基であり、
前記R 30 及び前記R 40 がそれぞれ独立に、水素、炭素数1乃至4のアルキル基、置換基を有していてもよいフェニル基、置換基を有していてもよいビフェニル基のいずれかであるビピリジン化合物。 - 下記式(100)で表されるビピリジン化合物。
- 下記式(106)で表されるビピリジン化合物。
- 請求項1乃至請求項6のいずれか一項に記載のビピリジン化合物を含む発光素子用材料。
- 請求項1乃至請求項6のいずれか一項に記載のビピリジン化合物を含む有機半導体材料。
- 第1の電極と、第2の電極との間に、
請求項1乃至請求項6のいずれか一項に記載のビピリジン化合物を含む発光素子。 - 請求項9に記載の発光素子を有するディスプレイモジュール。
- 請求項9に記載の発光素子を有する照明モジュール。
- 請求項9に記載の発光素子と、前記発光素子を制御する手段を備えた発光装置。
- 請求項9に記載の発光素子を表示部に有し、前記発光素子を制御する手段を備えた表示装置。
- 請求項9に記載の発光素子を照明部に有し、前記発光素子を制御する手段を備えた照明装置。
- 請求項9に記載の発光素子を有する電子機器。
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TWI633100B (zh) | 2013-07-19 | 2018-08-21 | 半導體能源研究所股份有限公司 | 有機化合物、發光元件、顯示器模組、照明模組、發光裝置、顯示裝置、照明設備及電子裝置 |
KR102331669B1 (ko) | 2013-11-13 | 2021-11-25 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 디스플레이 모듈, 조명 모듈, 발광 장치, 표시 장치, 전자 기기, 및 조명 장치 |
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