JP2008174538A - 複素環含有の有機金属錯体及びそれを利用した有機発光素子 - Google Patents
複素環含有の有機金属錯体及びそれを利用した有機発光素子 Download PDFInfo
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- JP2008174538A JP2008174538A JP2007174236A JP2007174236A JP2008174538A JP 2008174538 A JP2008174538 A JP 2008174538A JP 2007174236 A JP2007174236 A JP 2007174236A JP 2007174236 A JP2007174236 A JP 2007174236A JP 2008174538 A JP2008174538 A JP 2008174538A
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- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 40
- 125000002524 organometallic group Chemical group 0.000 title claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 9
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 229910052790 beryllium Inorganic materials 0.000 claims abstract description 8
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 8
- 229910052802 copper Inorganic materials 0.000 claims abstract description 8
- 229910052742 iron Inorganic materials 0.000 claims abstract description 8
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 8
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 8
- 238000002347 injection Methods 0.000 claims description 32
- 239000007924 injection Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 18
- 230000000903 blocking effect Effects 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 14
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 9
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 8
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- 239000002019 doping agent Substances 0.000 claims description 8
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- 125000001424 substituent group Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 3
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
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- 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 5
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 4
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- 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 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- 0 Cc(cccc1CC2Cc3c-4cc(cccc5)c5c3)c1-c1*2c-4ccc1C=C Chemical compound Cc(cccc1CC2Cc3c-4cc(cccc5)c5c3)c1-c1*2c-4ccc1C=C 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- FMOZIATXSMLFJS-UHFFFAOYSA-N 1-[2-cyclohexyloxy-4-ethoxy-5-(2-methoxyphenoxy)-3-phenoxy-6-propan-2-yloxyphenoxy]naphthalene Chemical group COC1=C(C=CC=C1)OC1=C(C(=C(C(=C1OCC)OC1=CC=CC=C1)OC1CCCCC1)OC1=CC=CC2=CC=CC=C12)OC(C)C FMOZIATXSMLFJS-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 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
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- -1 for example Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 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 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 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 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B31—MAKING ARTICLES OF PAPER, CARDBOARD OR MATERIAL WORKED IN A MANNER ANALOGOUS TO PAPER; WORKING PAPER, CARDBOARD OR MATERIAL WORKED IN A MANNER ANALOGOUS TO PAPER
- B31B—MAKING CONTAINERS OF PAPER, CARDBOARD OR MATERIAL WORKED IN A MANNER ANALOGOUS TO PAPER
- B31B70/00—Making flexible containers, e.g. envelopes or bags
- B31B70/14—Cutting, e.g. perforating, punching, slitting or trimming
- B31B70/146—Cutting, e.g. perforating, punching, slitting or trimming using tools mounted on a drum
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D81/00—Containers, packaging elements, or packages, for contents presenting particular transport or storage problems, or adapted to be used for non-packaging purposes after removal of contents
- B65D81/18—Containers, packaging elements, or packages, for contents presenting particular transport or storage problems, or adapted to be used for non-packaging purposes after removal of contents providing specific environment for contents, e.g. temperature above or below ambient
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D85/00—Containers, packaging elements or packages, specially adapted for particular articles or materials
- B65D85/50—Containers, packaging elements or packages, specially adapted for particular articles or materials for living organisms, articles or materials sensitive to changes of environment or atmospheric conditions, e.g. land animals, birds, fish, water plants, non-aquatic plants, flower bulbs, cut flowers or foliage
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- 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
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
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- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D2205/00—Venting means
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- 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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Abstract
Description
R1〜R11は、それぞれ独立的に、水素原子、シアノ基、ヒドロキシ基、ニトロ基、ハロゲン原子、置換または非置換のC1−C20アルキル基、置換または非置換のC1−C20アルコキシ基、置換または非置換のC6−C20アリール基、置換または非置換のC7−C20アリールアルキル基、置換または非置換のC2−C20アルキルアルコキシ基、置換または非置換のC7−C20アリールアルコキシ基、置換または非置換のC6−C20アリールアミノ基、置換または非置換のC1−C20アルキルアミノ基、置換または非置換のC6−C20アリールアミノ基、または置換または非置換のC2−C20複素環基であり、またはR1〜R11から選択された二つ以上の置換基は相互連結されて飽和または不飽和の炭素環、または飽和または不飽和の複素環を形成可能であり、Mは、Be、Mg、Zn、Ca、Cr、Fe、Co、NiまたはCuであり、Xは、NまたはPであり、Yは、OまたはSである。
R12及びR13は、それぞれ独立的に、水素原子、シアノ基、ヒドロキシ基、ニトロ基、ハロゲン原子、置換または非置換のC1−C20アルキル基、置換または非置換のC1−C20アルコキシ基、置換または非置換のC6−C20アリール基、置換または非置換のC7−C20アリールアルキル基、置換または非置換のC2−C20アルキルアルコキシ基、置換または非置換のC7−C20アリールアルコキシ基、置換または非置換のC6−C20アリールアミノ基、置換または非置換のC1−C20アルキルアミノ基、置換または非置換のC6−C20アリールアミノ基、または置換または非置換のC2−C20複素環基であり、Mは、Be、Mg、Zn、Ca、Cr、Fe、Co、NiまたはCuであり、Xは、NまたはPであり、Yは、OまたはSである。
R14、R15及びR16は、それぞれ独立的に、水素原子、シアノ基、ヒドロキシ基、ニトロ基、ハロゲン原子、置換または非置換のC1−C20アルキル基、置換または非置換のC1−C20アルコキシ基、置換または非置換のC6−C20アリール基、置換または非置換のC7−C20アリールアルキル基、置換または非置換のC2−C20アルキルアルコキシ基、置換または非置換のC7−C20アリールアルコキシ基、置換または非置換のC6−C20アリールアミノ基、置換または非置換のC1−C20アルキルアミノ基、置換または非置換のC6−C20アリールアミノ基、または置換または非置換のC2−C20複素環基であり、Mは、Be、Mg、Zn、Ca、Cr、Fe、Co、NiまたはCuであり、Xは、NまたはPであり、Yは、OまたはSである。
〔合成例1〕
下記反応式1の反応経路によって化合物9を合成した:
前記合成例1で合成した化合物9を電子注入層として使用して、次のような構造を有するOLEDを製作した:m−MTDATA(750A)/α−NPD(150A)/DSA(300A):TPBe(3%)/Alq3(200A)/化合物1(50A)/Al(3000A)。
アノードは、コーニング15Ω/cm2(1200Å)ITOガラス基板を50mmX50mmX0.7mmのサイズに切って、イソプロピルアルコール及び純水中で各5分間超音波洗浄した後、30分間UVオゾン洗浄して使用した。前記基板の上部にm−MTDATAを真空蒸着して、正孔注入層を750Åの厚さに形成した。次いで、前記正孔注入層の上部に、α−NPDを150Åの厚さに真空蒸着して、正孔輸送層を形成した。正孔輸送層を形成した後、この正孔輸送層の上部に、DSAをホストとし、ドーパントとしてTPBeを3%使用して、これを真空蒸着して300Åの厚さに発光層を形成した。その後、前記発光層の上部にAlq3を真空蒸着して、200Åの厚さの電子輸送層を形成した。この電子輸送層の上部に、Liq 50Å(電子注入層)及びAl 3000Å(負極電極)を順次に真空蒸着してLiq/Al電極を形成することによって、図1Bに示すような有機電界発光素子を製造した:m−MTDATA(750Å)/α−NPD(150Å)/DSA(300Å):TPBe(3%)/Alq3(200Å)/Liq(50Å)/Al(3000Å)。
前記実施例及び比較例に対して、(電流−電圧特性、輝度特性、効率特性及び消費電力特性)を評価して下記表1に表した。前記電流−電圧特性の評価には、Keithleyを使用し、輝度特性評価、効率特性評価及び消費電力特性の評価には、IVL測定装置(PhotoResearch PR650 Keithley 238)を使用した。
Claims (12)
- 下記化学式1を有することを特徴とするOLED用の複素環含有の有機金属錯体:
R1〜R11は、それぞれ独立的に、水素原子、シアノ基、ヒドロキシ基、ニトロ基、ハロゲン原子、置換または非置換のC1−C20アルキル基、置換または非置換のC1−C20アルコキシ基、置換または非置換のC6−C20アリール基、置換または非置換のC7−C20アリールアルキル基、置換または非置換のC2−C20アルキルアルコキシ基、置換または非置換のC7−C20アリールアルコキシ基、置換または非置換のC6−C20アリールアミノ基、置換または非置換のC1−C20アルキルアミノ基、置換または非置換のC6−C20アリールアミノ基、または置換または非置換のC2−C20複素環基であり、またはR1〜R11から選択された二つ以上の置換基は、相互連結されて飽和または不飽和の炭素環、または飽和または不飽和の複素環を形成可能であり、
Mは、Be、Mg、Zn、Ca、Cr、Fe、Co、NiまたはCuであり、
Xは、NまたはPであり、
Yは、OまたはSである。 - 前記化学式1で表示される化合物は、下記化学式2ないし6で表示される化合物のうち何れか一つを有することを特徴とする請求項1に記載のOLED用の複素環含有の有機金属錯体:
R12及びR13は、それぞれ独立的に、水素原子、シアノ基、ヒドロキシ基、ニトロ基、ハロゲン原子、置換または非置換のC1−C20アルキル基、置換または非置換のC1−C20アルコキシ基、置換または非置換のC6−C20アリール基、置換または非置換のC7−C20アリールアルキル基、置換または非置換のC2−C20アルキルアルコキシ基、置換または非置換のC7−C20アリールアルコキシ基、置換または非置換のC6−C20アリールアミノ基、置換または非置換のC1−C20アルキルアミノ基、置換または非置換のC6−C20アリールアミノ基、または置換または非置換のC2−C20複素環基であり、
Mは、Be、Mg、Zn、Ca、Cr、Fe、Co、NiまたはCuであり、
Xは、NまたはPであり、
Yは、OまたはSである。 - 前記化学式1で表示される化合物は、下記化学式7または8で表示される化合物を有することを特徴とする請求項1に記載のOLED用の複素環含有の有機金属錯体:
R14、R15及びR16は、それぞれ独立的に、水素原子、シアノ基、ヒドロキシ基、ニトロ基、ハロゲン原子、置換または非置換のC1−C20アルキル基、置換または非置換のC1−C20アルコキシ基、置換または非置換のC6−C20アリール基、置換または非置換のC7−C20アリールアルキル基、置換または非置換のC2−C20アルキルアルコキシ基、置換または非置換のC7−C20アリールアルコキシ基、置換または非置換のC6−C20アリールアミノ基、置換または非置換のC1−C20アルキルアミノ基、置換または非置換のC6−C20アリールアミノ基、または置換または非置換のC2−C20複素環基であり、
Mは、Be、Mg、Zn、Ca、Cr、Fe、Co、NiまたはCuであり、
Xは、NまたはPであり、
Yは、OまたはSである。 - R12〜R16は、それぞれ独立的に、水素原子、フェニル基またはメチル基であることを特徴とする請求項2または請求項3に記載のOLED用の複素環含有の有機金属錯体。
- 前記Xは、窒素であり、前記Yは、酸素であることを特徴とする請求項2または請求項3に記載のOLED用の複素環含有の有機金属錯体。
- 第1電極、第2電極及び前記第1電極と前記第2電極との間に少なくとも有機膜を備えるOLEDであって、前記有機膜は、請求項1または請求項2に記載の複素環含有の有機金属錯体を含むことを特徴とするOLED。
- 前記有機膜は、電子輸送層または電子注入層であることを特徴とする請求項7に記載のOLED。
- 前記有機膜は、発光層であることを特徴とする請求項7に記載のOLED。
- 前記発光層は、ホスト及びドーパントの総重量100重量部に対してドーパントである前記複素環含有の有機金属錯体1ないし50重量部を含むことを特徴とする請求項9に記載のOLED。
- 前記有機膜は、正孔注入層、正孔輸送層、電子阻止層、発光層、正孔阻止層、電子輸送層及び電子注入層からなる群から選択された一つ以上の層をさらに備えることを特徴とする請求項7に記載のOLED。
- 前記素子は、第1電極/正孔輸送層/発光層/電子輸送層/第2電極、第1電極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/第2電極または第1電極/正孔注入層/正孔輸送層/発光層/正孔阻止層/電子輸送層/電子注入層/第2電極の構造を有することを特徴とする請求項11に記載のOLED。
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