JP2016535723A - Oledでの使用のためのホウ素含有化合物 - Google Patents
Oledでの使用のためのホウ素含有化合物 Download PDFInfo
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- JP2016535723A JP2016535723A JP2016519990A JP2016519990A JP2016535723A JP 2016535723 A JP2016535723 A JP 2016535723A JP 2016519990 A JP2016519990 A JP 2016519990A JP 2016519990 A JP2016519990 A JP 2016519990A JP 2016535723 A JP2016535723 A JP 2016535723A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 158
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title abstract description 7
- 229910052796 boron Inorganic materials 0.000 title abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 239000000463 material Substances 0.000 claims description 61
- 239000011159 matrix material Substances 0.000 claims description 58
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 229920000642 polymer Polymers 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 239000000412 dendrimer Substances 0.000 claims description 19
- 229920000736 dendritic polymer Polymers 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 230000000903 blocking effect Effects 0.000 claims description 11
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 9
- 229910052727 yttrium Inorganic materials 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000003367 polycyclic group Polymers 0.000 claims description 3
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- 125000004104 aryloxy group Chemical group 0.000 claims description 2
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- 238000009472 formulation Methods 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 238000007689 inspection Methods 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 93
- -1 poly (p-phenylene) Polymers 0.000 description 52
- 239000002019 doping agent Substances 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 235000019557 luminance Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 229910052788 barium Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- 238000000260 fractional sublimation Methods 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 238000005457 optimization Methods 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 230000008021 deposition Effects 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 238000003077 quantum chemistry computational method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
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- NOTKALFQBCUAKB-UHFFFAOYSA-N 9,9'-spirobi[fluorene]-4'-ylboronic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=C2C=CC=C1B(O)O NOTKALFQBCUAKB-UHFFFAOYSA-N 0.000 description 2
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- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
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- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
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- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
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- 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
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- H—ELECTRICITY
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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
- H10K85/30—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
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- H—ELECTRICITY
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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
- H10K85/658—Organoboranes
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/30—Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
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- H—ELECTRICITY
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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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- 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
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Abstract
Description
(1)基板、
(2)電極、多くは、金属もしくは無機であるが、有機もしくはポリマー伝導性材料からも成る、
(3)電荷注入層(複数)もしくは中間層(複数)、たとえば、電極の不均性の補償用のためであり(「平坦化層」)、多くは、伝導性のドープされたポリマーから成る、
(4)有機半導体、
(5)可能ならば、さらなる電荷輸送層、電荷注入層もしくは電荷ブロック層、
(6)対電極、(2)で特定された材料、
(7)被包。
X1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16は、出現毎に同一か異なり、N、CR2またはC-Zであり、ここで、X1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16基の少なくとも一つは、C-Zであり、2個の隣接するX1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16基は、同時にNではなく;
Y、Y1は、出現毎に同一か異なり、結合またはBR3、O、S、C(R3)2、C(R3)=C(R3)、N(R3)、Si(R3)2、C=O、C=C(R3)2、S=O、SO2、C(R3)2-C(R3)2および1,2-フェニレンから、好ましくは、O、S、C(R3)2、C(R3)=C(R3)、N(R3)、Si(R3)2、C=O、C=C(R3)2、S=O、SO2、C(R3)2-C(R3)2および1,2-フェニレンから、選ばれる2価ブリッジであり;
R1、R2、R3は、出現毎に同一か異なり、H、D、F、Cl、Br、I、CHO、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CN、NO2、Si(R4)3、B(OR4)2、OSO2R4、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上のR4基により置換されてよく、ここで、1以上の隣接しないCH2基は、R4C=CR4、C≡C、Si(R4)2、Ge(R4)2、Sn(R4)2、C=O、C=Se、P(=O)(R4)、SO、SO2、O、SもしくはCONR4で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、夫々、1以上のR4基により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環系、または1以上のR4基で置換されてよい5〜40個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基またはジアリールアミノもしくはジヘテロアリールアミノもしくはアリールヘテロアリールアミノ基またはこれらの系の組み合わせであり;同時に、2個の以上の隣接するR1、R2もしくはR3置換基は、モノあるいはポリ環式の脂肪族もしくは芳香族環系を互いに形成してもよく;
R4は、出現毎に同一か異なり、H、D、F、Cl、Br、I、CHO、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CN、NO2、Si(R5)3、B(OR5)2、OSO2R5、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上のR5基により置換されてよく、ここで、1以上の隣接しないCH2基は、C≡C、Si(R5)2、Ge(R5)2、Sn(R5)2、C=O、C=Se、P(=O)(R5)、SO、SO2、O、SもしくはCONR5で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。またはこれらの系の組み合わせであり;同時に、2個の以上の隣接するR4置換基は、モノあるいはポリ環式の脂肪族もしくは芳香族環系を互いに形成してもよく;
Ar1は、出現毎に同一か異なり、1以上のR3基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環系であり;同時に、同じ燐原子に結合する2個のAr1基は、単結合またはB(R5)、C(R5)2、Si(R5)2、C=O、C=NR5、C=C(R5)2、O、S、S=O、SO2、N(R5)、P(R5)およびP(=O)R5から選ばれるブリッジにより互いに結合してよく;
R5は、出現毎に同一か異なり、H、D、Fまたは1〜20個の炭素原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基(ここで、水素原子は、Fで置き代えられてもよい。)であり;同時に、2個以上の隣接するR5置換基は、モノあるいはポリ環式の脂肪族もしくは芳香族環系を一緒に形成してもよく;
Zは、式(III)の基であり
Ar2、Ar3は、出現毎に同一か異なり、1以上のR3基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環系であり;同時に、Ar2およびAr3基は、単結合またはB(R5)、C(R5)2、Si(R5)2、C=O、C=NR5、C=C(R5)2、O、S、S=O、SO2、N(R5)、P(R5)およびP(=O)R5から選ばれるブリッジにより互いに結合してもよく;
qは、0または1であり;および
Ar4は、出現毎に同一か異なり、夫々、1以上のR3基により置換されてよい6〜40個の炭素原子を有するアリール基もしくは3〜40個の炭素原子を有するヘテロアリール基であり;ここで、
破線は、芳香族もしくは複素環式芳香族環の炭素原子へのZ基の結合であり、
ただし、YとY1の両者が結合である場合には、X2とX7は、同時に式C-Zの基でなくてよいか、またはX11とX14は、同時に式C-Zの基でなくてよい。
意味するものと解される。アルキニル基は、たとえば、エチニル、プロピニル、ブチニル、ペンチニル、ヘキシニル、ヘプチニルまたはオクチニルを意味するものと解される。C1〜C40-アルコキシ基は、たとえば、メトキシ、トリフルオロメトキシ、エトキシ、n-プロポキシ、i-プロポキシ、n-ブトキシ、i-ブトキシ、s-ブトキシ、t-ブトキシまたは2-メチルブトキシを意味するものと解される。
HOMO(eV)=((HEh*27.212)−0.9899)/1.1206
LUMO(eV)=((LEh*27.212)−2.0041)/1.385
これらの値は、本出願の文脈で、材料のHOMOおよびLUMOエネルギー準位とみなすべきである。
以下の合成は、他に断らない限り、保護ガス雰囲気下、無水溶媒中で行われる。金属錯体を遮光して、または黄色光下で、追加的な処理をする。溶媒および試薬を、たとえばSigma-ALDRICHまたはABCRから購入することができる。角括弧内の夫々の番号または個々の化合物について示された番号は、文献から知られた化合物のCAS番号である。
A:シントンSの合成:
例S1: 4-ブロモスピロ-9,9’-ビフルオレン
変形1:
1000mLのTHF中、−78℃に冷却した100ミリモルの一臭化物または50ミリモルの二臭化物または33ミリモルの三臭化物または25ミリモルの四臭化物のよく撹拌した溶液または懸濁液に対して、n−ヘキサン中の105mLのn−BuLiの2.5Mを、温度が−55℃を超えない速度で滴下する。添加の終了後、その混合物をさらに2時間撹拌し、次いで、200mLのTHF中の110ミリモルのフルオロボランの溶液を、温度が−55℃を超えない速度で滴下する。その混合物をさらに−78℃で1時間撹拌し、次いで、徐々に室温まで温めておく。50mLのメタノールの添加後、溶媒を実質的に減圧下で除去し、残留物を500mLのジクロロメタンに取込み、有機相を、その度毎に200mLの水で五度、200mLの飽和塩化ナトリウム溶液で一度、洗浄し、次いで硫酸マグネシウムで脱水させる。溶媒の除去後に得られた残留物を(たとえば、メタノール、エタノール、イソプロパノール等のアルコールと組み合わせて、トルエン、アセトン、酢酸エチルから)反復して再結晶化することにより精製し、最後に高真空(p=約10―5〜10−6mbar、T約250〜400℃)で、二度、分別昇華させる。
100ミリモルの臭化物と、110ミリモルのボロン酸と、300ミリモルの炭酸水素ナトリウムと、2ミリモルのS−Phosと、1ミリモルの酢酸パラジウム(II)と、300mLのトルエンと、200mLのジオキサンと、300mLの水との混合物を還流下で16時間加熱する。冷却後、水相を除去し、有機相を、その度毎に300mLの水で三度、300mLの塩化ナトリウム溶液で一度、洗浄し、硫酸マグネシウムで脱水させ、乾燥剤をセライト床を使用して濾過する。溶媒の除去後に得られた残留物を(たとえば、メタノール、エタノール、イソプロパノール等のアルコールと組み合わせて、トルエン、アセトン、酢酸エチルから)反復して再結晶化することにより精製し、最後に高真空(p=約10―5〜10−6mbar、T約250〜400℃)で、二度、分別昇華させる。
1)真空処理された素子:
本発明のOLEDおよび先行技術のOLEDは、WO 2004/058911による一般的な方法により製造されるが、ここに記載される状況(層の厚さの変化、使用する材料)に適合される。
本発明の化合物の使用は、蛍光および燐光OLEDにおけるTMM、ETM、HBMとしての使用を含んでいる。
A:可溶性機能的材料から
本発明の化合物は、溶液から処理することもでき、プロセス技術に関して、真空処理されたOLEDと比較すると著しく単純であるにもかかわらず良好な特性を有するOLEDが得られる。このような素子の製造は、既に何度も文献(たとえばWO 2004/037887)に記載されているポリマー発光ダイオード(PLED)の製造に基づく。
化合物の三重項レベルT1を、量子化学計算によって決定する。この目的のために、「ガウシアン03W」(Gaussian Inc.)ソフトウエアパッケージを使用する。有機物質を計算するために、「基底状態/準実験的/デフォルトスピン/AM1/(電荷0/一重項スピン)」法によって、第一に、幾何学的な最適化を実行する。続いて幾何学的な最適化を基準にしてエネルギー計算を実行する。これを、「6−31G(d)」ベースセット(電荷0/一重項スピン)を用いる「TD−SCF/DFT/デフォルトスピン/B3PW91」法を使用して実施する。エネルギー計算は、eVでT1状態のエネルギーを与え、これを表1では2つの化合物である参照1と例18について報告している。
Claims (25)
- 式(I)および/または(II)の少なくとも一つの構造を含む臭素含有化合物;
X1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16は、出現毎に同一か異なり、N、CR2またはC-Zであり、ここでX1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16基の少なくとも一つは、C-Zであり、2個の隣接するX1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16基は、同時にNではなく;
Y、Y1は、出現毎に同一か異なり、結合またはBR3、O、S、C(R3)2、C(R3)=C(R3)、N(R3)、Si(R3)2、C=O、C=C(R3)2、S=O、SO2、C(R3)2-C(R3)2および1,2-フェニレンから選ばれる2価ブリッジであり;
R1、R2、R3は、出現毎に同一か異なり、H、D、F、Cl、Br、I、CHO、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CN、NO2、Si(R4)3、B(OR4)2、OSO2R4、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上のR4基により置換されてよく、ここで、1以上の隣接しないCH2基は、R4C=CR4、C≡C、Si(R4)2、Ge(R4)2、Sn(R4)2、C=O、C=Se、P(=O)(R4)、SO、SO2、O、SもしくはCONR4で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)または、夫々、1以上のR4基により置換されてよい5〜40個の芳香族環原子を有する芳香族もしくは複素環式芳香族環系、または1以上のR4基で置換されてよい5〜40個の芳香族環原子を有するアリールオキシもしくはヘテロアリールオキシ基またはこれらの構造の組み合わせであり;同時に、2個の以上の隣接するR1、R2もしくはR3置換基は、モノあるいはポリ環式の脂肪族もしくは芳香族環系を互いに形成してもよく;
R4は、出現毎に同一か異なり、H、D、F、Cl、Br、I、CHO、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CN、NO2、Si(R5)3、B(OR5)2、OSO2R5、1〜40個の炭素原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個の炭素原子を有する分岐あるいは環式アルキル、アルコキシもしくはチオアルコキシ基(夫々は、1以上のR5基により置換されてよく、ここで、1以上の隣接しないCH2基は、C≡C、Si(R5)2、Ge(R5)2、Sn(R5)2、C=O、C=Se、P(=O)(R5)、SO、SO2、O、SもしくはCONR5で置き代えられてよく、ここで、1以上の水素原子は、D、F、Cl、Br、I、CNもしくはNO2で置き代えられてよい。)またはこれらの系の組み合わせであり;同時に、2個の以上の隣接するR4置換基は、モノあるいはポリ環式の脂肪族もしくは芳香族環系を互いに形成してもよく;
Ar1は、出現毎に同一か異なり、1以上のR3基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環系であり;同時に、同じ燐原子に結合する2個のAr1基は、単結合またはB(R5)、C(R5)2、Si(R5)2、C=O、C=NR5、C=C(R5)2、O、S、S=O、SO2、N(R5)、P(R5)およびP(=O)R5から選ばれるブリッジにより互いに結合してよく;
R5は、出現毎に同一か異なり、H、D、Fまたは1〜20個の炭素原子を有する脂肪族、芳香族および/または複素環式芳香族炭化水素基(ここで、水素原子は、Fで置き代えられてもよい。)であり;同時に、2個以上の隣接するR5置換基は、モノあるいはポリ環式の脂肪族もしくは芳香族環系を一緒に形成してもよく;
Zは、式(III)の基であり
Ar2、Ar3は、出現毎に同一か異なり、1以上のR3基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環系であり;同時に、Ar2およびAr3基は、単結合またはB(R5)、C(R5)2、Si(R5)2、C=O、C=NR5、C=C(R5)2、O、S、S=O、SO2、N(R5)、P(R5)およびP(=O)R5から選ばれるブリッジにより互いに結合してもよく;
qは、0または1であり;および
Ar4は、出現毎に同一か異なり、夫々、1以上のR3基により置換されてよい6〜40個の炭素原子を有するアリール基もしくは3〜40個の炭素原子を有するヘテロアリール基であり;ここで、
破線は、芳香族もしくは複素環式芳香族環の炭素原子へのZ基の結合であり、
ただし、YとY1の両者が結合である場合には、X2とX7は、同時に式C-Zの基でなくてよいか、またはX11とX14は、同時に式C-Zの基でなくてよい。 - 2個を超えないX1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16基は、Nであることを特徴とする、請求項1記載の化合物。
- 2個を超えず、好ましくは、丁度1個のX1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15およびX16基は、C-Zであることを特徴とする、請求項1または2記載の化合物。
- X5、X6、X7、X8、X9、X10、X11およびX12基は、CR2であることを特徴とする、請求項1〜3何れか1項記載の化合物。
- X2、X7、X11およびX14基は、式CR2の基であることを特徴とする、請求項1〜4何れか1項記載の化合物。
- X2、X7、X11およびX14基の少なくとも2個、および好ましくは、少なくとも3個は、式C-Hの基であることを特徴とする、請求項1〜5何れか1項記載の化合物。
- qは0であり、それで、Z基の臭素原子は、フルオレンもしくはスピロ基に直接結合していることを特徴とする、請求項1〜6何れか1項記載の化合物。
- 式(I)において、X1、X2、X3、X4、X5、X6、X7およびX8基の少なくとも4個は、C-Hであり、および/または式(II)において、X1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15およびX16基の少なくとも8個、および好ましくは、少なくとも12個は、C-Hであることを特徴とする、請求項1〜7何れか1項記載の化合物。
- 式(I)において、X1、X4、X5およびX8基の少なくとも1個は、C-Zであり、および/または式(II)において、X1、X4、X5、X8、X9、X12、X13およびX16基の少なくとも1個は、C-Zであることを特徴とする、請求項1〜8何れか1項記載の化合物。
- 式(I)において、R1基の少なくとも1個は、好ましくは、2個のR1基は、3個までのR4基により置換されてよい1〜10個の炭素原子を有するアルキル基または6〜10個の炭素原子を有するアリール基であることを特徴とする、請求項1〜9何れか1項記載の化合物。
- Yが、Oまたは結合、好ましくは、結合であることを特徴とする、請求項12記載の化合物。
- Yは、Oまたは結合、好ましくは、結合であり、Y1は、結合、O、S、C=OまたはN(R3)、好ましくは、結合、OまたはN(Ar1)であり、使用される記号は、請求項1での所与の定義を有することを特徴とする、請求項1〜12何れか1項記載の化合物。
- Ar2およびAr3基は、3個までのR3基により置換されてよい6個の炭素原子を有するアリール基であり;同時に、A2およびA3基は、単結合またはB(R5)、C(R5)2、Si(R5)2、C=O、C=NR5、C=C(R5)2、O、S、S=O、SO2、N(R5)、P(R5)およびP(=O)R5から選ばれる2価ブリッジにより互いに結合してよいことを特徴とする、請求項1〜18何れか1項記載の化合物。
- 化合物が、オリゴマー、ポリマーまたはデンドリマーであることを特徴とする、請求項1〜19何れか1項記載の化合物。
- 請求項1〜20何れか1項記載の少なくとも一つの化合物と、蛍光エミッター、燐光エミッター、ホスト材料、マトリックス材料、電子輸送材料、電子注入材料、正孔伝導材料、正孔注入材料、電子ブロック材料および正孔ブロック材料より成る群から選ばれる少なくとも一つのさらなる化合物とを含む組成物。
- 請求項1〜20何れか1項記載の少なくとも一つの化合物または請求項21記載の少なくとも一つの組成物と少なくとも一つの溶媒とを含む調合物。
- 少なくとも一つのアリールリチウム化合物を、少なくとも一つのハロボランおよび/または少なくともボリン酸エステルと反応させることによる、請求項1〜20何れか1項記載の化合物の製造方法。
- 請求項1〜20何れか1項記載の化合物の、正孔ブロック材料、電子注入材料および/または電子輸送材料としての電子素子での使用。
- 請求項1〜20何れか1項記載の少なくとも一つの化合物または請求項21記載の組成物を含む電子素子であって、電子素子は、好ましくは、有機エレクトロルミッセンス素子、有機集積回路、有機電界効果トランジスタ、有機薄膜トランジスタ、有機発光トランジスタ、有機太陽電池、有機光学検査素子、有機光受容器、有機電場消光素子、発光電子化学電池および有機レーザーダイオードより成る群から選ばれる電子素子。
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US20160248015A1 (en) | 2016-08-25 |
WO2015049030A3 (de) | 2015-05-28 |
EP3904361A3 (de) | 2022-04-20 |
EP3052505A2 (de) | 2016-08-10 |
CN111909187A (zh) | 2020-11-10 |
WO2015049030A2 (de) | 2015-04-09 |
JP6576915B2 (ja) | 2019-09-18 |
CN111848659A (zh) | 2020-10-30 |
EP3904361A2 (de) | 2021-11-03 |
US10224493B2 (en) | 2019-03-05 |
KR102310370B1 (ko) | 2021-10-07 |
CN105612164A (zh) | 2016-05-25 |
EP3052505B1 (de) | 2021-06-23 |
KR20160065157A (ko) | 2016-06-08 |
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