JP2013035822A - 有機金属化合物およびそれを用いた有機エレクトロルミネセンス素子 - Google Patents
有機金属化合物およびそれを用いた有機エレクトロルミネセンス素子 Download PDFInfo
- Publication number
- JP2013035822A JP2013035822A JP2012096010A JP2012096010A JP2013035822A JP 2013035822 A JP2013035822 A JP 2013035822A JP 2012096010 A JP2012096010 A JP 2012096010A JP 2012096010 A JP2012096010 A JP 2012096010A JP 2013035822 A JP2013035822 A JP 2013035822A
- Authority
- JP
- Japan
- Prior art keywords
- organometallic compound
- group
- compound
- electroluminescent device
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002902 organometallic compounds Chemical class 0.000 title claims abstract description 30
- 238000005401 electroluminescence Methods 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052757 nitrogen Chemical group 0.000 claims description 15
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 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 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000012459 cleaning agent Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 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 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- -1 thickness 30 nm) Chemical compound 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 description 2
- IESNTEJIQPLWNT-UHFFFAOYSA-N 4-phenylbenzo[g][1]benzothiole Chemical group C1=C2C=CC=CC2=C2SC=CC2=C1C1=CC=CC=C1 IESNTEJIQPLWNT-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229910000611 Zinc aluminium Inorganic materials 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- HXFVOUUOTHJFPX-UHFFFAOYSA-N alumane;zinc Chemical compound [AlH3].[Zn] HXFVOUUOTHJFPX-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001690 polydopamine Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 230000029663 wound healing Effects 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- 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
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- 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
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
これにより、赤色リン光性OLEDに適する新規の有機化合物を開発して、上述の問題を解決することが必要である。
本発明の別の実施態様では、有機エレクトロルミネセント素子が提供される。装置は、一対の電極および一対の電極間に位置する電界発光要素を含み、該電界発光要素は、上述の有機金属化合物(赤ドーパントとなる)を含む。
本発明は、下記式(I)または式(II)で表される構造を有する有機金属化合物を提供する:
本発明のいくつかの実施態様によると、本発明の有機金属化合物は式(III)、式(IV)または式(V)で表される構造を有する:
化合物 Ir−THQ−acacの製造
初めに、化合物(1)(2−(2−アミノエチル)チオフェン,2.0g,10.0mmol)および50mLトルエンを250mLのボトルに加えた。続いて、化合物(2)(1.29g,10.00mmole)、K2CO3(2M,20mL)、Pd(PPH3)4(0.43g)および(t−Bu)3P(0.23g)を室温下でボトルに加えた。加熱還流後、NaOH水溶液(20%)をボトルに加え、一晩攪拌した。精製後、歩留まりが69%の化合物(3)を得た。合成経路は以下に示される:
1H−NMR(CDCl3,200MHz) δ=8.49(d,J=5.4Hz,2H),8.41(d,J=8.8Hz,2H),8.23(d,J=8.4Hz,2H),8.02(d,J=7.6Hz,2H),7.69(d,J=5.4Hz,2H),7.44(t,J=8.0Hz,2H),7.28(t,J=8.0Hz,2H),7.03(dd,J=8.0,1.8Hz,2H),6.71(d,J=1.8Hz,2H),4.47(s,1H),1.35(s,6H),0.88(s,18H).
化合物 Ir−THQ−phacの製造
初めに、化合物(6)(3.68g,11.60mmol)、IrCl3.xH2O(1.65g)、2−メトキシエタノール(15mL)および水(5mL)を100mLのボトルに加えた。140℃で24時間加熱後、化合物(7)(1.30g)、K2CO3(0.76g)および30mLの2−メトキシエタノールをボトルに加えた。24時間反応後、ボトルを室温まで冷却し、水(50mL)で反応を停止した。生成物を、カラムクロマトグラフィー(n−へキサン/ジクロロメタン(3:1))で精製した後、Ir−THQ−phacを得た。合成経路は以下に示される:
1H−NMR(CDCl3,200MHz) δ=8.51(d,J=5.4Hz,2H),8.45(d,J=8.8Hz,2H),8.28(d,J=8.4Hz,2H),8.08(d,J=7.6Hz,2H),7.71(d,J=5.4Hz,2H),7.66(d,J=8.0Hz,2H),7.46(t,J=8.0Hz,2H),7.41(d,J=1.8Hz,1H),7.28(t,J=8.0Hz,2H),7.13(dd,J=8.0,1.8Hz,2H),7.03(dd,J=8.0,1.8Hz,2H),6.73(d,J=1.8Hz,2H),1.36(s,6H),0.89(s,18H).
化合物 Ir−THQ−N−acacの製造
初めに、化合物(1)(2−(2−アミノエチル)チオフェン2.02g,10.0mmol)および50mLトルエンを、250mLのボトルに加えた。続いて、化合物(9)(1.29g,10.00mmole)、K2CO3(2M,20mL)、Pd(PPH3)4(0.43g)および(t−Bu)3P(0.23g)室温のボトルに加えた。加熱還流後、NaOH水溶液(20%)をボトルに加え一晩攪拌した。精製後、化合物(10)が得られた。合成経路は以下に示される:
化合物 Ir−THQ−N−phacの製造
化合物(12)(3.68g,11.60mmol)、IrCl3.xH2O(1.65g)、2−メトキシエタノール(15mL)および水(5mL)を100mLのボトルに加えた。140℃で24時間加熱後、化合物(7)(1.30g)、K2CO3(0.76g)および30mLの2−メトキシエタノールをボトルに加えた。24時間反応後、ボトルを室温間冷却し、水(50mL)で反応を停止した。生成物を、カラムクロマトグラフィー(n−へキサン/ジクロロメタン(3:1))で精製後、Ir−THQ−N−phacを得た。合成経路は以下に示される:
図1は、有機エレクトロルミネセント素子10の具体例を示す。図1に示されるように、エレクトロルミネセント素子10は、基板12、底部電極14、エレクトロルミネセンス素子16、頂部電極18を含む。有機エレクトロルミネセント素子は、トップエミッション、ボトムエミッションまたはデュアルエミッション装置である。
エレクトロルミネセンス素子16は少なくとも発光層を含み、さらに、正孔注入層、正孔輸送層、電子輸送層および電子注入層を含む。本発明の好ましい態様中、エレクトロルミネセンス素子16の少なくとも一層は上述の有機金属化合物を含む。
100nmのインジウムスズ酸化物(ITO)薄膜を有するガラス基板を提供して、洗浄剤、アセトンおよびイソプロパノールを用いて、超音波かくはんで洗浄する。窒素フローで乾燥させた後、ITO膜をUV/オゾン処理した。続いて、NPB(N,N’−ジ(ナフタリン−l−イル)−N,N’−ジフェニル−ベンジジン、厚さ40nm)、Ir−THQ−acacをドープしたCBP(4,4’−N,N’−カルバゾール−ビフェニル):
NPB(40nm)/CBP:Ir−THQ−acac(3%)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)
実施例5に示されるエレクトロルミネセント素子(1)の光学特性をPR650(Photo Research Inc.で購入)およびMinolta TS110で測定した。結果を以下に示す:
最適な効率:34.1cd/A,19.5 lm/W;
放射効率:11.9cd/A,4.2 lm/W@1000cd/m2;
エレクトロルミネセンス波長:612nm;
CIE色度座標:(0.63,0.35).
100nmのインジウムスズ酸化物(ITO)薄膜を有するガラス基板を提供して、洗浄剤、アセトンおよびイソプロパノールを用いて、超音波かくはんで洗浄した。窒素フローで乾燥させた後、ITO膜をUV/オゾン処理した。続いて、NPB(N,N’−ジ(ナフタリン−l−イル)−N,N’−ジフェニル−ベンジジン、厚さ40nm)、Ir−THQ−acacをドープしたCBP(4,4’−N,N’−カルバゾール−ビフェニル):
NPB(40nm)/CBP:Ir−THQ−acac(4%)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)
実施例6に示されるエレクトロルミネセント素子(2)の光学特性をPR650(Photo Research Inc.で購入)および Minolta TS110で測定した。結果を以下に示す:
最適な効率:35.9cd/A,28.2 lm/W;
放射効率:11.4cd/A,5.7lm/W @1000 cd/m2;
エレクトロルミネセンス波長:616nm;
CIE色度座標:(0.65,0.34).
100nmのインジウムスズ酸化物(ITO)薄膜を有するガラス基板を提供して、洗浄剤、アセトンおよびイソプロパノールを用いて、超音波かくはんで洗浄した。窒素フローで乾燥させた後、ITO膜をUV/オゾン処理した。続いて、NPB(N,N’−ジ(ナフタリン−l−イル)−N,N’−ジフェニル−ベンジジン、厚さ40nm)、Ir−THQ−acacをドープしたCBP(4,4’−N,N’−カルバゾール−ビフェニル):
NPB(40nm)/CBP:Ir−THQ−acac(4%)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)
実施例7に示されるエレクトロルミネセント素子(3)の光学特性をPR650(Photo Research Inc.で購入)およびMinolta TS110で測定した。結果を以下に示す:
最適な効率:18.7cd/A,9.7 lm/W;
放射効率:10.0cd/A,3.5 lm/W@1000cd/m2;
エレクトロルミネセンス波長:616nm;
CIE色度座標:(0.65,0.34).
100nmのインジウムスズ酸化物(ITO)薄膜を有するガラス基板を提供し、洗浄剤、アセトンおよびイソプロパノールを用いて、超音波かくはんで洗浄した。窒素フローで乾燥させた後、ITO膜をUV/オゾン処理.続いて、NPB(N,N’−ジ(ナフタリン−l−イル)−N,N’−ジフェニル−ベンジジン、厚さ40nm)、Ir−THQ−acacをドープしたCBP(4,4’−N,N’−カルバゾール−ビフェニル):
NPB(40nm)/BAlq:Ir−THQ−acac(4%)(30nm)/Bphen(30nm)/LiF(0.5nm)/Al(120nm)
実施例8に示されるエレクトロルミネセント素子(4)の光学特性をPR650(Photo Research Inc.で購入)およびMinolta TS110で測定した。結果を以下に示す:
最適な効率:14.2cd/A,7.4lm/W;
放射効率:11.5cd/A,4.8 lm/W@1000cd/m2;
エレクトロルミネセンス波長:620nm;
CIE色度座標:(0.65,0.35).
実施例を用いて、および、好ましい態様の観点で本発明を前述したが、本発明は決して開示された態様に限定されるものではなく、当該技術を熟知する者なら誰でも、本発明の精神と領域を脱しない範囲内で各種の変形や同様の構成をカバーすることが意図されている。従って本発明の保護範囲は、そのようなすべての変形や同様の構成を包含するように最大限の解釈がなされるべきである。
12 基板
14 底部電極
16 エレクトロルミネセンス素子
18 頂部電極
Claims (7)
- A1は一方の側で酸素原子を介してIrと結合し、他方の側で別の酸素原子を介してIrと結合することを特徴とする請求項1に記載の有機金属化合物。
- R1は、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、tert−ブチル基、ペンチル基またはヘキシル基であることを特徴とする請求項1に記載の有機金属化合物。
- 有機エレクトロルミネセンス素子であって、
一対の電極;および
前記一対の電極間に設置された電界発光要素を含み、
前記電界発光要素は請求項1の前記有機金属化合物を含むことを特徴とする有機エレクトロルミネセンス素子。 - 前記電界発光要素は、バイアス電圧下で、赤色光線を発光することを特徴とする請求項6に記載の有機エレクトロルミネセンス素子。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TW100127917 | 2011-08-05 | ||
TW100127917A TWI429652B (zh) | 2011-08-05 | 2011-08-05 | 有機金屬化合物及包含其之有機電激發光裝置 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013035822A true JP2013035822A (ja) | 2013-02-21 |
JP5544390B2 JP5544390B2 (ja) | 2014-07-09 |
Family
ID=47609813
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012096010A Expired - Fee Related JP5544390B2 (ja) | 2011-08-05 | 2012-04-19 | 有機金属化合物およびそれを用いた有機エレクトロルミネセンス素子 |
Country Status (4)
Country | Link |
---|---|
US (1) | US8871360B2 (ja) |
JP (1) | JP5544390B2 (ja) |
CN (1) | CN102911212B (ja) |
TW (1) | TWI429652B (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015155405A (ja) * | 2014-02-18 | 2015-08-27 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料、及びデバイス |
WO2018066583A1 (ja) * | 2016-10-05 | 2018-04-12 | 三菱ケミカル株式会社 | イリジウム錯体化合物、並びに前記化合物を含有する組成物、有機電界発光素子、表示装置及び照明装置 |
JP2022183135A (ja) * | 2021-05-27 | 2022-12-08 | エルジー ディスプレイ カンパニー リミテッド | 有機金属化合物、及びこれを含む有機電界発光素子 |
Families Citing this family (80)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9831447B2 (en) | 2013-10-08 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
TWI632147B (zh) | 2013-12-26 | 2018-08-11 | 財團法人工業技術研究院 | 有機金屬錯合物及包含其之有機電激發光裝置 |
TWI586672B (zh) | 2014-12-03 | 2017-06-11 | 財團法人工業技術研究院 | 有機金屬化合物及包含其之有機電激發光裝置 |
TWI526448B (zh) | 2014-12-03 | 2016-03-21 | 財團法人工業技術研究院 | 有機金屬化合物、及包含其之有機發光裝置 |
US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
US10299752B2 (en) * | 2015-04-27 | 2019-05-28 | Toshiba Medical Systems Corporation | Medical image processing apparatus, X-ray CT apparatus, and image processing method |
US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10181564B2 (en) | 2015-08-26 | 2019-01-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10361381B2 (en) | 2015-09-03 | 2019-07-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN106883270B (zh) | 2015-11-26 | 2019-03-26 | 财团法人工业技术研究院 | 有机金属化合物、包含其的有机发光装置 |
US20170229663A1 (en) | 2016-02-09 | 2017-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862054B2 (en) | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180130956A1 (en) | 2016-11-09 | 2018-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20180370999A1 (en) | 2017-06-23 | 2018-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN107501336A (zh) * | 2017-09-12 | 2017-12-22 | 武汉大学 | 一种有机红色磷光铱配合物及其制备方法和在有机电致发光器件中的应用 |
US11377458B2 (en) * | 2017-10-16 | 2022-07-05 | Samsung Electronics Co., Ltd. | Organometallic compound and organic light-emitting device including the same |
US20190161504A1 (en) | 2017-11-28 | 2019-05-30 | University Of Southern California | Carbene compounds and organic electroluminescent devices |
EP3492480B1 (en) | 2017-11-29 | 2021-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN108276452A (zh) * | 2018-03-20 | 2018-07-13 | 烟台显华光电材料研究院有限公司 | 一类用作磷光材料的过渡金属配合物、其制备方法及应用 |
US20200075870A1 (en) | 2018-08-22 | 2020-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
KR102380561B1 (ko) * | 2019-01-30 | 2022-03-30 | 엘티소재주식회사 | 화합물, 유기 광전자 소자 및 표시 장치 |
US20200251664A1 (en) | 2019-02-01 | 2020-08-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2020158491A (ja) | 2019-03-26 | 2020-10-01 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
US20210032278A1 (en) | 2019-07-30 | 2021-02-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210047354A1 (en) | 2019-08-16 | 2021-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210135130A1 (en) | 2019-11-04 | 2021-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210217969A1 (en) | 2020-01-06 | 2021-07-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
EP4214772A1 (en) | 2020-09-18 | 2023-07-26 | Samsung Display Co., Ltd. | Organic electroluminescent device |
US20220158096A1 (en) | 2020-11-16 | 2022-05-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220162243A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220165967A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220271241A1 (en) | 2021-02-03 | 2022-08-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059915A3 (en) | 2021-02-26 | 2022-12-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A3 (en) | 2021-02-26 | 2023-03-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298192A1 (en) | 2021-03-05 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298190A1 (en) | 2021-03-12 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298193A1 (en) | 2021-03-15 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220340607A1 (en) | 2021-04-05 | 2022-10-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US20220352478A1 (en) | 2021-04-14 | 2022-11-03 | Universal Display Corporation | Organic eletroluminescent materials and devices |
US20220407020A1 (en) | 2021-04-23 | 2022-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230006149A1 (en) | 2021-04-23 | 2023-01-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230133787A1 (en) | 2021-06-08 | 2023-05-04 | University Of Southern California | Molecular Alignment of Homoleptic Iridium Phosphors |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4231804A3 (en) | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230292592A1 (en) | 2022-03-09 | 2023-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230337516A1 (en) | 2022-04-18 | 2023-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230389421A1 (en) | 2022-05-24 | 2023-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240016051A1 (en) | 2022-06-28 | 2024-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240188419A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240180025A1 (en) | 2022-10-27 | 2024-05-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240196730A1 (en) | 2022-10-27 | 2024-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240188319A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240188316A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240247017A1 (en) | 2022-12-14 | 2024-07-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003234192A (ja) * | 2001-12-06 | 2003-08-22 | Konica Corp | 有機エレクトロルミネッセンス素子および表示装置 |
JP2005276799A (ja) * | 2004-02-27 | 2005-10-06 | Fuji Photo Film Co Ltd | 発光素子 |
WO2010033550A1 (en) * | 2008-09-16 | 2010-03-25 | Universal Display Corporation | Phosphorescent materials |
WO2010118029A1 (en) * | 2009-04-06 | 2010-10-14 | Universal Display Corporation | Metal complex comprising novel ligand structures |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL276942A (ja) * | 1961-04-08 | 1900-01-01 | ||
US5846982A (en) | 1996-06-14 | 1998-12-08 | Eli Lilly And Company | Inhibition of serotonin reuptake |
JP4154138B2 (ja) | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子、表示装置及び金属配位化合物 |
CN1285601C (zh) * | 2000-11-30 | 2006-11-22 | 佳能株式会社 | 发光器件和显示器 |
JP5135660B2 (ja) | 2001-09-27 | 2013-02-06 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
TWI242999B (en) * | 2004-12-22 | 2005-11-01 | Ind Tech Res Inst | Organometallic compound and organic electroluminescent device including the same |
CN101166745A (zh) | 2005-03-02 | 2008-04-23 | 菲布罗根有限公司 | 噻吩并吡啶化合物和其使用方法 |
JP2009046435A (ja) | 2007-08-21 | 2009-03-05 | Mitsubishi Tanabe Pharma Corp | グルココルチコイド受容体モジュレーター |
-
2011
- 2011-08-05 TW TW100127917A patent/TWI429652B/zh not_active IP Right Cessation
- 2011-08-18 CN CN201110238699.1A patent/CN102911212B/zh not_active Expired - Fee Related
-
2012
- 2012-01-27 US US13/360,217 patent/US8871360B2/en not_active Expired - Fee Related
- 2012-04-19 JP JP2012096010A patent/JP5544390B2/ja not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003234192A (ja) * | 2001-12-06 | 2003-08-22 | Konica Corp | 有機エレクトロルミネッセンス素子および表示装置 |
JP2005276799A (ja) * | 2004-02-27 | 2005-10-06 | Fuji Photo Film Co Ltd | 発光素子 |
WO2010033550A1 (en) * | 2008-09-16 | 2010-03-25 | Universal Display Corporation | Phosphorescent materials |
WO2010118029A1 (en) * | 2009-04-06 | 2010-10-14 | Universal Display Corporation | Metal complex comprising novel ligand structures |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015155405A (ja) * | 2014-02-18 | 2015-08-27 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料、及びデバイス |
US11024816B2 (en) | 2014-02-18 | 2021-06-01 | Universal Display Corporation | Organic electroluminescent materials and devices |
WO2018066583A1 (ja) * | 2016-10-05 | 2018-04-12 | 三菱ケミカル株式会社 | イリジウム錯体化合物、並びに前記化合物を含有する組成物、有機電界発光素子、表示装置及び照明装置 |
JPWO2018066583A1 (ja) * | 2016-10-05 | 2019-07-18 | 三菱ケミカル株式会社 | イリジウム錯体化合物、並びに前記化合物を含有する組成物、有機電界発光素子、表示装置及び照明装置 |
JP7074064B2 (ja) | 2016-10-05 | 2022-05-24 | 三菱ケミカル株式会社 | イリジウム錯体化合物、並びに前記化合物を含有する組成物、有機電界発光素子、表示装置及び照明装置 |
JP2022183135A (ja) * | 2021-05-27 | 2022-12-08 | エルジー ディスプレイ カンパニー リミテッド | 有機金属化合物、及びこれを含む有機電界発光素子 |
JP7366194B2 (ja) | 2021-05-27 | 2023-10-20 | エルジー ディスプレイ カンパニー リミテッド | 有機金属化合物、及びこれを含む有機電界発光素子 |
Also Published As
Publication number | Publication date |
---|---|
TWI429652B (zh) | 2014-03-11 |
CN102911212B (zh) | 2015-09-30 |
US8871360B2 (en) | 2014-10-28 |
JP5544390B2 (ja) | 2014-07-09 |
TW201307364A (zh) | 2013-02-16 |
CN102911212A (zh) | 2013-02-06 |
US20130033172A1 (en) | 2013-02-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5544390B2 (ja) | 有機金属化合物およびそれを用いた有機エレクトロルミネセンス素子 | |
JP7015353B2 (ja) | カルバゾール含有化合物 | |
TWI580666B (zh) | Aromatic amine derivatives, organic electroluminescent elements and electronic machines | |
JP5432147B2 (ja) | 有機金属錯体誘導体およびこれを用いた有機発光素子 | |
CN107325089B (zh) | 用于有机发光二极管的2-氮杂三亚苯材料 | |
JP2019206546A (ja) | ヘテロレプティックイリジウムカルベン錯体及びそれを用いた発光デバイス | |
TWI601715B (zh) | 基於茚並三亞苯的銥金屬錯合物及使用其的有機電激發光裝置 | |
TWI421255B (zh) | 有機金屬化合物及包含其之有機電激發光裝置 | |
KR102637435B1 (ko) | 유기 전계발광 물질 및 디바이스 | |
TW201100432A (en) | Metal complex comprising novel ligand structures | |
JP2005197262A (ja) | 有機電界発光素子 | |
TW201634473A (zh) | 銥金屬錯合物及使用其的有機電激發光裝置 | |
JP7458483B2 (ja) | 金属錯体及びその用途 | |
JP5391427B2 (ja) | 白色有機電界発光素子及びその製造方法 | |
TW201700472A (zh) | 化合物及使用其的有機電激發光元件 | |
CN110563746A (zh) | 一种新型含so2螺环结构化合物及其在oled器件中的应用 | |
CN109776396A (zh) | 一种具有螺二芴结构的有机化合物及其制备方法与应用 | |
CN109776395A (zh) | 一种含氟螺二芴结构的空穴材料及其制备方法与应用 | |
JP6007491B2 (ja) | 1,2,4,5−置換フェニル誘導体とその製造方法、及び有機電界発光素子 | |
US11380848B2 (en) | Organic compound and organic electroluminescence device using the same | |
TW201525102A (zh) | 有機金屬化合物、包含其之有機發光裝置、及其製備方法 | |
CN111116673A (zh) | 红色磷光化合物和使用该化合物的有机电致发光器件 | |
JP2018518841A (ja) | 有機エレクトロルミネッセンス素子 | |
KR101145684B1 (ko) | 이미드기를 갖는 이리듐 복합체 및 이를 포함하는 전기인광소자 | |
KR101641351B1 (ko) | 아이소퀴놀린 유도체 화합물 및 이를 이용한 유기전계 발광소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130719 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130731 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131030 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140430 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140512 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5544390 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |