JP5801651B2 - 化合物、発光素子および発光装置 - Google Patents
化合物、発光素子および発光装置 Download PDFInfo
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- JP5801651B2 JP5801651B2 JP2011184386A JP2011184386A JP5801651B2 JP 5801651 B2 JP5801651 B2 JP 5801651B2 JP 2011184386 A JP2011184386 A JP 2011184386A JP 2011184386 A JP2011184386 A JP 2011184386A JP 5801651 B2 JP5801651 B2 JP 5801651B2
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- 150000001875 compounds Chemical class 0.000 title claims description 85
- -1 biphenyldiyl group Chemical group 0.000 claims description 164
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 2
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- 238000006243 chemical reaction Methods 0.000 description 55
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- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 42
- 229910052799 carbon Inorganic materials 0.000 description 40
- 238000000034 method Methods 0.000 description 36
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 19
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- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 12
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- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 7
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- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 6
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- 238000000295 emission spectrum Methods 0.000 description 6
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- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 150000003855 acyl compounds Chemical class 0.000 description 5
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- 229910003437 indium oxide Inorganic materials 0.000 description 5
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 5
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- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 5
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- 125000003545 alkoxy group Chemical group 0.000 description 4
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
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- HUPKVQASBZEGJF-UHFFFAOYSA-N 2-[4-[9-(4-bromophenyl)fluoren-9-yl]phenyl]-1-phenylbenzimidazole Chemical compound C1=CC(Br)=CC=C1C1(C=2C=CC(=CC=2)C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 HUPKVQASBZEGJF-UHFFFAOYSA-N 0.000 description 3
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- ONDZNPJPRAIDHK-UHFFFAOYSA-N n-(4-carbazol-9-ylphenyl)-n-phenyl-9,9'-spirobi[fluorene]-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3(C4=CC=CC=C4C4=CC=CC=C43)C3=CC=CC=C3C2=CC=1)C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 ONDZNPJPRAIDHK-UHFFFAOYSA-N 0.000 description 1
- AJNJGJDDJIBTBP-UHFFFAOYSA-N n-(9,10-diphenylanthracen-2-yl)-n,9-diphenylcarbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C(C=3C=CC=CC=3)=C3C=CC=CC3=C(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 AJNJGJDDJIBTBP-UHFFFAOYSA-N 0.000 description 1
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 1
- VZYZZKOUCVXTOJ-UHFFFAOYSA-N n-[4-[4-(n-(9,9-dimethylfluoren-2-yl)anilino)phenyl]phenyl]-9,9-dimethyl-n-phenylfluoren-2-amine Chemical group C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C2C(C)(C)C3=CC=CC=C3C2=CC=1)C1=CC=CC=C1 VZYZZKOUCVXTOJ-UHFFFAOYSA-N 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
- HCIIFBHDBOCSAF-UHFFFAOYSA-N octaethylporphyrin Chemical compound N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 HCIIFBHDBOCSAF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 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
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 230000000149 penetrating effect Effects 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910001936 tantalum oxide Inorganic materials 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 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
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
- H10K85/611—Charge transfer complexes
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
-
- 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
- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
- H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Description
本実施の形態では、本発明に係る有機化合物として、例えば下記有機半導体材料について説明する。
本実施の形態では、実施の形態1で示した下記一般式(G1)で表される有機半導体材料の合成方法を説明する。実施の形態1で示した有機半導体材料は、フルオレンの9位の炭素に電子輸送性ユニットと、ホール輸送性ユニットを同時に結合する材料である。つまり、非対称の物質である。ところが、無置換フルオレンの9位の炭素に結合する二つの水素はエネルギー的に完全に同一であって、識別ができないため、無置換フルオレンと電子輸送性ユニット及びホール輸送性ユニットのカップリング反応では合成が非常に困難である。そこで、本発明者らは鋭意研究を重ねた結果、以下のような合成方法によって実施の形態1で示した有機半導体材料を得ることができることを見出した。
まず、電子受容ユニットEAのハロゲン化物(化合物1)と、ホール受容ユニットHAのアシル化合物(化合物2)とを反応させることで、ケトン構造を有する化合物3を得る(反応式(A−1−1))。
合成法2では、実施の形態1で示した一般式(G1)で表される有機半導体材料のフルオレン9位に結合しているホール受容ユニットHAを、ホール輸送骨格HA 1とアリーレン基R1を用いてHA 1−R1−基として表す。これにより、一般式(G1)で表される有機半導体材料は、下記一般式(G1−1)の様に表すことができる。
合成法3では、実施の形態1に示した一般式(G1)で表される有機半導体材料のフルオレン9位に結合している電子受容ユニットEAを、電子輸送骨格EA 1とアリーレン基R2を用いてEA 1−R2−基として表す。これにより一般式(G1)で表される有機半導体材料は下記一般式(G1−2)の様に表すことができる。
合成法4では、実施の形態1で示した一般式(G1)で表される有機半導体材料のフルオレン9位に結合しているホール受容ユニットHAを、ホール輸送骨格HA 1とアリーレン基R1を用いてHA 1−R1基として表し、電子受容ユニットEAを、電子輸送骨格EA 1とアリーレン基R2を用いてEA 1−R2基として表す。これにより、一般式(G1)で表される有機半導体材料は、下記一般式(G1−3)の様に表すことができる。
本実施の形態では、実施の形態1で示した有機半導体材料を用いた発光素子の一態様について、図1および図2を用いて説明する。
本実施の形態は、本発明に係る複数の発光ユニットを積層した構成の発光素子(以下、積層型素子という)の態様について、図3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積層型発光素子である。各発光ユニットの構成としては、実施の形態3で示したEL層の構成と同様な構成を用いることができる。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る。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について説明する。
本実施の形態では、本発明の発光素子を有する発光装置について説明する。
本実施の形態では、実施の形態4に示す発光装置をその一部に含む本発明の電子機器について説明する。本発明の電子機器は、実施の形態3又は実施の形態4で示した発光素子を有し、低消費電力の表示部を有する。
本合成例では、実施の形態1に一般式(G1)として示した有機半導体材料の一つである、4−フェニル−4’−{9−[4−(1−フェニル−1H−ベンゾイミダゾール−2−イル)−フェニル]−フルオレン−9−イル}−トリフェニルアミン (略称:F−BPA−Pbim)の合成法について詳しく説明する。F−BPA−Pbimの構造式を以下に示す。
300mL三口フラスコにて、活性マグネシウム410mg(17mmol)を脱水テトラヒドロフラン(THF)5mL中で撹拌し、ここに1,2−ジブロモエタンを約0.2mL加えて発泡、発熱するのを確認した。ここに、4−ブロモフェニル−1−フェニル−1H−ベンゾイミダゾールの5.2g(15mmol)を脱水THF溶液50mLに溶かした溶液を加えた。これを4時間加熱撹拌した後、室温まで冷まし、グリニャール試薬とした。
続いて、500mL三口フラスコに、4−ブロモベンゾイルクロリドを3.7g(17mmol)と、脱水THFを150mL加え、−40℃にて撹拌した。ここに、先程のグリニャール試薬を滴下し、1時間撹拌したのち、約15時間室温にて撹拌した。
反応後、ここに1N−塩酸を酸性になるまで加えた。得られた混合液の有機相を水で洗浄した後、硫酸マグネシウムを加えて水分を吸着させた。この懸濁液をろ過し、得られたろ液を濃縮し、酢酸エチルとトルエンを加えて再結晶を行った。粉末2.5gを得た。上記反応スキームを(A−1)に示す。
200mL三口フラスコにて、脱水THF20mL中に溶かした2−ブロモビフェニルを1.4g(6.0mmol)を−80℃にて撹拌した。ここに、4−ブロモフェニル−4−(1−フェニル−1H−ベンゾイミダゾール−2−イル)−フェニル−メタノン2.5gに脱水THF50mLを加えた懸濁液を滴下して、約15時間撹拌し、アルコール体を形成させた。
反応後、ここに1N−塩酸を酸性になるまで加えた。得られた混合液の有機相を水で洗浄した後、濃縮した。
得られた濃縮物に、氷酢酸30mLと、濃塩酸1mLを加え、135℃で8時間加熱撹拌した。反応後、水にこの反応液を加え、得られた固体を水で洗浄した。ヘキサンを加えて超音波洗浄し、白色粉末100mgを得た。上記反応スキームを(A−2)に示す。
200mL三口フラスコに、2−{4−[9−(4−ブロモフェニル)−フルオレン−9−イル]−フェニル}−1−フェニル−1H−ベンゾイミダゾールを100mg(0.2mmol)、4−ビフェニルフェニルアミンを50mg(0.2mmol)、ナトリウム tert−ブトキシドを500mg(0.5mmol)、ビス(ジベンジリデンアセトン)パラジウム(0)を5.0mg(10μmol)加え、フラスコ内の雰囲気を窒素置換した。この混合物へ、脱水キシレン10mLを加えた。この混合物を、減圧下で攪拌しながら脱気した後、トリ(tert−ブチル)ホスフィン(10wt%ヘキサン溶液)60μL(30μmol)を加えた。この混合物を、窒素雰囲気下、130℃で2.5時間加熱撹拌し、反応させた。
102 第1の電極
103 EL層
104 第2の電極
111 ホール注入層
112 ホール輸送層
113 発光層
114 電子輸送層
115 電子注入層
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 ソース側駆動回路
602 画素部
603 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 EL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
701 本体
702 表示部
703 操作スイッチ
704 操作スイッチ
710 本体
711 表示部
712 メモリ部
713 操作部
714 イヤホン
901 筐体
902 液晶層
903 バックライト
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 EL層
956 電極
1001 筐体
1002 筐体
1101 表示部
1102 スピーカー
1103 マイクロフォン
1104 操作キー
1105 ポインティングデバイス
1106 カメラ用レンズ
1107 外部接続端子
1108 イヤホン端子
1201 キーボード
1202 外部メモリスロット
1203 カメラ用レンズ
1204 ライト
2001 筐体
2002 光源
3001 照明装置
3002 テレビ装置
9101 筐体
9102 支持台
9103 表示部
9104 スピーカー部
9105 ビデオ入力端子
9201 本体
9202 筐体
9203 表示部
9204 キーボード
9205 外部接続ポート
9206 ポインティングデバイス
9301 本体
9302 表示部
9303 筐体
9304 外部接続ポート
9305 リモコン受信部
9306 受像部
9307 バッテリー
9308 音声入力部
9309 操作キー
9310 接眼部
9401 本体
9402 筐体
9403 表示部
9404 音声入力部
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Claims (6)
- 式(G2−1)で表される化合物。
(式中、E1は窒素原子または酸素原子を表し、窒素原子の場合はフェニル基又はビフェニル基が結合している。また、m及びnはそれぞれ独立に0又は1の値を示し、α1又はα2はそれぞれ独立にフェニレン基又はビフェニルジイル基のいずれか一を表す。また、Ar1又はAr2はそれぞれ独立にフェニル基、ナフチル基、フェナントリル基及びトリフェニレニル基のいずれか一を表す。) - 式(G2−2)で表される化合物。
(式中、E1は窒素原子または酸素原子を表し、窒素原子の場合はフェニル基又はビフェニル基が結合している。また、mは0又は1の値を示す。) - 式(G2−3)で表される化合物。
(式中、mは0又は1の値を示す。) - 式(1)で表される化合物。
- 一対の電極間に、請求項1乃至4のいずれか一項に記載の化合物を含む発光素子。
- 請求項5に記載の発光素子と、前記発光素子の発光を制御する制御回路とを有する発光装置。
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