CN113512043A - 有机化合物、制剂、有机发光器件和显示或照明装置 - Google Patents
有机化合物、制剂、有机发光器件和显示或照明装置 Download PDFInfo
- Publication number
- CN113512043A CN113512043A CN202110942133.0A CN202110942133A CN113512043A CN 113512043 A CN113512043 A CN 113512043A CN 202110942133 A CN202110942133 A CN 202110942133A CN 113512043 A CN113512043 A CN 113512043A
- Authority
- CN
- China
- Prior art keywords
- unsubstituted
- substituted
- organic
- organic compound
- layer
- 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.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 239000010410 layer Substances 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 7
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 230000000903 blocking effect Effects 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 1
- 230000005540 biological transmission Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000005281 excited state Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- -1 iridium metal complex Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
-
- 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
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
技术领域
本发明涉及一种有机化合物,尤其涉及一种有机化合物及包含其的有机发光器件,属于有机发光领域。
背景技术
有机发光器件(例如OLED)发光分为荧光发光和磷光发光两种方式。根据理论推测,由电荷在结合而引起的单重激发态与三重激发态的比例为1:3,使用小分子荧光材料时,能用于发光的仅为全部能量的25%,其余的75%的能量因三重激发态的非发光机制而损失掉,因此,一般认为,荧光材料的内部量子效率极限为25%。1998年Baldo和Forrest教授等人发现三线态磷光可以在室温下利用,并将原来内量子效率的上限提高至100%,三重态磷光体经常均是由重金属原子组成的络合物,利用重原子效应,强烈的自旋轨域耦合作用造成单重激发态和三重激发态的能阶相互混合,使得原本被禁止的三重态能量缓解以磷光的形式发光,量子效率也随之大幅提高。目前有机OLED组件中的发光层几乎全部使用主客体发光体系结构,即在主发光体中掺杂客体发光材料,常用的客体发光材料为铱金属配合物。
因此,有必要开发一种新型的有机化合物,且将其应用于有机发光器件,可提高器件的电流效率、降低器件的操作电压且延长器件的使用寿命。
发明内容
为了克服现有技术中的缺陷,本发明的目的在于提供一种新颖的有机化合物,且该有机化合物用于构建有机发光器件,可显著提高有机发光器件的电流效率、降低器件的操作电压且延长器件的使用寿命。
为了实现本发明的目的,本发明的技术方案如下:
本发明提供了有机化合物,其结构如式I所示:
其中,X1-X5各自独立地选自N或CR4,X1-X4中至少2者为N原子;Y选自O、S、 NR5、C(R5)2或Si(R5)2;
R1-R5各自独立地选自氢、氘、卤素、氰基、取代或未取代的C1-C30的烷基、取代或未取代的C6-C30的芳基、取代或未取代的C2-C30的杂芳基、取代或未取代的C1-C30的硅烷基;或彼此连接以形成单环或者多环的C5-C30的脂肪环或芳环,其中该杂芳基是指其中含有N、O、S、Si或P中至少一杂原子。
m、n和o各自独立地为0到4的整数,其中当m、n和o均≥2时,R1、R2或R3各自可以相同或不同。
优选地,其结构选自由以下组成的群组:
其中,X1-X5各自独立地选自N或CR4,且X1-X4中至少2者为N原子;
Y选自O、S、NR5、C(R5)2或Si(R5)2,其中,R2、R3和R5各自独立地选自氢、氘、卤素、氰基、取代或未取代的C1-C30的烷基、取代或未取代的C6-C30的芳基、取代或未取代的 C2-C30的杂芳基、取代或未取代的C1-C30的硅烷基;或者彼此连接以形成单环或者多环的 C5-C30的脂肪环或芳环;
m和o各自独立地为0到4的整数,当m和o均≥2时,R2或R3各自可以相同或不同。
更优选地,X5为N原子,且X1-X4各自独立地选自N或CR4,且X1-X4中至少2者为N 原子,其中,R1-R5各自独立地选自氢、氘、卤素、氰基、取代或未取代的C1-C30的烷基、取代或未取代的C6-C30的芳基、取代或未取代的C2-C30的杂芳基、取代或未取代的C1-C30 的硅烷基;或者彼此连接以形成单环或者多环的C5-C30的脂肪环或芳环;
m、n和o各自独立地为0到4的整数,当m、n和o均≥2时,R1、R2或R3各自可以相同或不同,但不代表本发明的保护范围限于此。
更优选地,R1-R5各自独立地选自由以下组成的群组,但不代表本发明的保护范围限于此:
更优选地,本该有机化合物选自由以下组成的群组,但不代表本发明的保护范围限于此:
本发明还提供了制剂,其包含该有机化合物和至少一种溶剂,该溶剂没有特别限制,可以使用本领域技术人员公知的不饱和烃溶剂(例如甲苯、二甲苯、均三甲苯、四氢化萘、十氢萘、双环己烷、正丁基苯、仲丁基苯、叔丁基苯等)、饱和烃溶剂(优选卤化饱和烃溶剂,例如四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、溴戊烷、氯己烷、溴己烷、氯环己烷、溴环己烷等)、醚类溶剂(例如四氢呋喃、四氢吡喃等)、酯类溶剂(例如苯甲酸烷基酯等),其中,该不饱和烃溶剂优选为卤化不饱和烃溶剂,例如氯苯、二氯苯或三氯苯等。
优选地,其还包含铱或铂金属配合物。
本发明还提供了一种半导体器件(优选为有机发光器件),其包括阴极层、阳极层和有机层,该有机层为空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层或电子传输层中至少一层,该有机层中至少一层含有如结构式I的有机化合物。
优选地,该有机化合物中至少一者作为有机发光器件发光层的主体材料,客体材料没有特别的限制。
优选地,该有机发光器件的发光层中还包含铱或铂金属配合物。
更优选地,该主体材料与所述铱或铂金属配合物的体积比为1:99~99:1。
本发明还提供了一种显示或照明装置,其包含该有机化合物。
结构式I所述的有机化合物可以单独使用,或和其他化合物混合使用;如结构式1所述的化合物可以使用其中一种化合物,也可以同时使用结构式I中的两种或两种以上化合物。
进一步的,结构式I所述的有机化合物作为有机发光器件发光层的主体材料,客体材料优选自铱或铂金属配合物。
本发明还要求保护本发明的发光器件在显示或照明装置中的应用。
本发明的有机化合物具有超过140度的玻璃化转变温度,可以有效防止该有机化合物在使用过程中发生晶化等,在将该有机化合物用于制作有机发光器件时,从而提升器件的使用寿命。特别地,用本发明的有机化合物作为有机发光器件中的主体材料或电子传输层材料使用,与现有技术中结构类似的化合物相比,可以明显提高有机发光器件的电流效率且降低操作电压。且由于该化合物的热稳定性好,空穴与电子的传输比较平衡,使得使用本发明的有机化合物可以显著延长有机发光器件的使用寿命。
附图说明
图1为本发明的有机发光器件的结构示意图;
其中,110代表基板,120表示阳极,130表示空穴注入层,140表示空穴传输层,150表示发光层,160表示空穴阻挡层,170表示电子传输层,180表示电子注入层,190表示阴极。
图2为本发明化合物C-22的差示扫描量热(DSC)的曲线图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合具体实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
本发明的有机发光器件(OLED器件)中含有空穴传输层,空穴传输材料可选自本领域公知的材料,特别优选地选自以下结构,但并不代表本发明限于以下结构:
本发明的OLED器件中含有的空穴传输层,其包含一种或多种p型掺杂剂。本发明优选的p 型掺杂剂为以下结构,但并不代表本发明限于以下结构:
本发明的电子传输层可以选自化合物ET-1至ET-13中的至少一种,但并不代表本发明限于以下结构:
电子传输层可以通过该有机化合物与一种或多种n型掺杂剂(如LiQ)共同形成。
本发明的具有式(I)所示的有机化合物的合成例如下:
其中中间体1和中间体2通过本领域公知的方法合成得到。
合成例
实施例1:化合物C-1的合成
在氮气气氛下,将中间体1(10毫摩尔)、中间体2(10毫摩尔)、NaH(20毫摩尔)、DMF(100毫升)加热至130度,反应24小时。反应结束后,将混合物倒入冰水中,过滤,固体粗品用冰水、冷甲醇洗涤,干燥。用二氯甲烷/甲醇(100:1~10:1)过硅胶柱纯化得到本发明的目标有机化合物C-1,产率76%。1H NMR(500MHz,CDCl3):δ7.20-7.28(m,4H),7.35(dd, 1H),7.43(dd,1H),7.51-7.78(m,8H),7.81(d,1H),7.98-8.12(m,6H),8.17(s,1H),8.24-8.41(m,4H),8.80(d,1H),9.07(d,1H),9.53(s,1H);MS(ESI):理论值687.23,实测687.2。
类似地,实施例2至21相关化合物的合成步骤如实施例1类似,其产率、质谱等测试结果如下:
实施例 | 化合物 | 产率 | 实测MS | 理论MS |
实施例2 | C-2 | 73% | 762.2 | 762.28 |
实施例3 | C-4 | 76% | 762.3 | 762.28 |
实施例4 | C-9 | 80% | 762.3 | 762.28 |
实施例5 | C-10 | 70% | 762.3 | 762.28 |
实施例6 | C-11 | 82% | 687.2 | 687.23 |
实施例7 | C-12 | 73% | 762.2 | 762.28 |
实施例8 | C-14 | 74% | 762.3 | 762.28 |
实施例9 | C-20 | 67% | 762.2 | 762.28 |
实施例10 | C-22 | 65% | 812.3 | 812.29 |
实施例11 | C-24 | 63% | 812.3 | 812.29 |
实施例12 | C-32 | 80% | 767.3 | 767.31 |
实施例13 | C-52 | 71% | 878.3 | 878.34 |
实施例14 | C-79 | 61% | 917.3 | 917.33 |
实施例15 | C-95 | 63% | 840.3 | 840.30 |
实施例16 | C-101 | 74% | 812.3 | 812.29 |
实施例17 | C-103 | 70% | 812.2 | 812.29 |
实施例18 | C-111 | 72% | 838.3 | 838.31 |
实施例19 | C-116 | 73% | 852.3 | 852.29 |
实施例20 | C-126 | 78% | 777.4 | 777.37 |
实施例21 | C-127 | 72% | 822.4 | 822.36 |
OLED器件制备与测试通用步骤包括:
a.清洗透明的OLED顶发光玻璃基板分别用去离子水、丙酮、异丙醇超声清洗15min, 80℃烘干1h,投入蒸镀腔,等离子处理阳极表面;
b.在阳极表面通过热蒸镀的方式蒸镀空穴注入层材料HT-1:P-3(97:3),厚度为10纳米;空穴传输层为HT-1,厚度为90纳米;电子阻挡层为HT-8,厚度为10纳米,发光层为本发明的有机化合物或RH-1~RH-4:RD-1(97:3v/v%),厚度为35纳米,电子传输层为ET-13:LiQ(50:50v/v%),厚度为35纳米,然后蒸镀阴极Yb为1纳米,Ag为14纳米,CPL层70纳米;
c.按照上述步骤完成OLED器件器件后,测量器件的电流效率和寿命,器件的电流-亮度-电压特性是由带有校正过的硅光电二极管的Keithley源测量系统(Keithley 2400Sourcemeter、Keithley 2000Currentmeter)完成的,电致发光光谱是由法国JY公司SPEXCCD3000光谱仪测量的,所有测量均在室温大气中完成。依据上述实施例和对比例电流效率、电压和寿命等特性显示在下表1中。
对比的主体材料RH-1~RH-4和RD-1结构式如下:
所得电致发光器件的检测数据见表1。
表1
从表1的结果可以看出,本发明所述的有机化合物与对比化合物RH-1~RH-4在结构上十分接近,区别是吸电子基团与稠环并吲哚的N相连的位置有明显的差异,RH-1、RH-2、RH-3 主要的连接方式是稠环并吲哚的N与吸电子的N处于邻位,相隔一个碳原子,而本发明采用的是喹啉等基团与稠环并吲哚的N相隔1个苯环,结构上十分相近,但是将其用到有机发光器件中,器件的综合性能出现了显著的差异,绝大部分器件结果显示出具有更高的电流效率和更长的操作寿命。以器件实施例11为例,与对比器件2相比,寿命提升了66%,效率更是提升了28%,同时器件的操作电压得到显著降低。器件实施例16和17则得到了更加显著的综合性能提升。以上结果充分说明,本发明的连接方式可以显著提升此类有机化合物在有机发光器件中的综合性能,得到了意想不到的效果,具有商业应用的前景。
以上所述,仅为本发明较佳的具体实施方式,但本发明的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明揭露的技术范围内,根据本发明的技术方案及其发明构思加以等同替换或改变,都应涵盖在本发明的保护范围之内。
Claims (12)
3.根据权利要求1或2所述的有机化合物,其中,X5为N原子且X1-X4各自独立地选自N或CR4,且X1-X4中至少2者为N原子,其中R1-R5各自独立地选自氢、氘、卤素、氰基、取代或未取代的C1-C30的烷基、取代或未取代的C6-C30的芳基、取代或未取代的C2-C30的杂芳基、取代或未取代的C1-C30的硅烷基;或者彼此连接以形成单环或者多环的C5-C30的脂肪环或芳环;
m、n和o各自独立地为0到4的整数,当m、n和o均≥2时,R1、R2或R3各自可以相同或不同。
6.制剂,其包含权利要求1或2所述的有机化合物和至少一种溶剂,其中所述溶剂为不饱和烃溶剂、饱和烃溶剂、醚类溶剂或酯类溶剂。
7.根据权利要求6所述的制剂,其中,其还包含铱或铂金属配合物。
8.有机发光器件,其包括阴极层、阳极层和有机层,所述有机层为空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层或电子传输层中至少一层,所述有机层中至少一层含有权利要求1或2所述的有机化合物。
9.根据权利要求8所述的有机发光器件,其中,权利要求1或2所述的有机化合物中至少一者作为所述有机发光器件发光层的主体材料。
10.根据权利要求9所述的有机发光器件,其中,所述有机发光器件的发光层中还包含铱或铂金属配合物。
11.根据权利要求10所述的有机发光器件,其中,所述主体材料与所述铱或铂金属配合物的体积比为1:99~99:1。
12.显示或照明装置,其包含权利要求1或2所述的有机化合物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110942133.0A CN113512043A (zh) | 2021-08-17 | 2021-08-17 | 有机化合物、制剂、有机发光器件和显示或照明装置 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110942133.0A CN113512043A (zh) | 2021-08-17 | 2021-08-17 | 有机化合物、制剂、有机发光器件和显示或照明装置 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN113512043A true CN113512043A (zh) | 2021-10-19 |
Family
ID=78069068
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202110942133.0A Pending CN113512043A (zh) | 2021-08-17 | 2021-08-17 | 有机化合物、制剂、有机发光器件和显示或照明装置 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113512043A (zh) |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20160103488A (ko) * | 2015-02-24 | 2016-09-01 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR20170077806A (ko) * | 2015-12-28 | 2017-07-06 | 에스에프씨 주식회사 | 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN107629068A (zh) * | 2017-04-28 | 2018-01-26 | 机光科技股份有限公司 | 有机电致发光材料及其应用 |
CN110526857A (zh) * | 2018-05-25 | 2019-12-03 | 北京鼎材科技有限公司 | 一种有机发光材料及其制备有机电致发光器件的应用 |
CN111004168A (zh) * | 2018-10-08 | 2020-04-14 | 机光科技股份有限公司 | 有机化合物及使用其的有机电激发光组件 |
CN112334463A (zh) * | 2018-11-02 | 2021-02-05 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
CN112533912A (zh) * | 2018-11-02 | 2021-03-19 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
CN113248485A (zh) * | 2020-08-06 | 2021-08-13 | 浙江华显光电科技有限公司 | 一种有机发光主体组合物及使用该组合物的有机发光器件 |
-
2021
- 2021-08-17 CN CN202110942133.0A patent/CN113512043A/zh active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20160103488A (ko) * | 2015-02-24 | 2016-09-01 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
KR20170077806A (ko) * | 2015-12-28 | 2017-07-06 | 에스에프씨 주식회사 | 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN107629068A (zh) * | 2017-04-28 | 2018-01-26 | 机光科技股份有限公司 | 有机电致发光材料及其应用 |
CN110526857A (zh) * | 2018-05-25 | 2019-12-03 | 北京鼎材科技有限公司 | 一种有机发光材料及其制备有机电致发光器件的应用 |
CN111004168A (zh) * | 2018-10-08 | 2020-04-14 | 机光科技股份有限公司 | 有机化合物及使用其的有机电激发光组件 |
CN112334463A (zh) * | 2018-11-02 | 2021-02-05 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
CN112533912A (zh) * | 2018-11-02 | 2021-03-19 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
CN113248485A (zh) * | 2020-08-06 | 2021-08-13 | 浙江华显光电科技有限公司 | 一种有机发光主体组合物及使用该组合物的有机发光器件 |
Non-Patent Citations (4)
Title |
---|
QIANG YANG: "Potential Safety Hazards Associated with Using N,N‑Dimethylformamide in Chemical Reactions", 《ORG. PROCESS RES. DEV.》 * |
孔令义: "《复杂天然产物波谱解析》", 30 September 2012, 中国医药科技出版社 * |
方起程: "《天然药物化学研究》", 30 September 2006, 中国协和医科大学出版社 * |
林锦明: "《化学实验室工作手册》", 31 January 2016, 第二军医大学出版社 * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Li et al. | Dendronized delayed fluorescence emitters for non-doped, solution-processed organic light-emitting diodes with high efficiency and low efficiency roll-off simultaneously: two parallel emissive channels | |
Wang et al. | Efficient deep-blue electrofluorescence with an external quantum efficiency beyond 10% | |
Deng et al. | Simple bipolar host materials incorporating CN group for highly efficient blue electrophosphorescence with slow efficiency roll-off | |
CN106467542B (zh) | 一种以蒽酮为核心的化合物及其应用 | |
WO2020134138A1 (zh) | 有机电致发光化合物及其制备方法和有机电致发光器件 | |
EP4276103A1 (en) | Spiro compound, preparation, organic electroluminescent diode, and display device | |
CN111675701B (zh) | 一种基于三苯胺结构的有机电致发光化合物及有机电致发光器件 | |
CN108250214B (zh) | 氧杂螺芴三苯胺衍生物、制备方法及其用途 | |
CN111320612A (zh) | 化合物及有机电致发光器件 | |
CN112552282B (zh) | 一种有机化合物和使用该化合物的有机光电元件 | |
CN113563253A (zh) | 一种以三芳胺为核心的有机化合物及其应用 | |
CN113501810B (zh) | 一种有机化合物和含其的有机光电元件 | |
CN116514859B (zh) | 一种窄发射发光化合物及在电子器件中的应用 | |
WO2022161453A1 (zh) | 一种有机金属配合物及含有该化合物的有机光电元件 | |
CN114644660A (zh) | 有机金属配合物、制剂、有机光电器件及显示或照明装置 | |
CN112479903A (zh) | 一种以均苯为核心的有机化合物及其应用 | |
CN110577508B (zh) | 一种以三芳胺为核心的化合物及其应用 | |
WO2019196950A1 (zh) | 一种以氧杂蒽酮为核心的化合物、其制备方法及其在oled上的应用 | |
CN110734444B (zh) | 一种以氮杂螺芴为核心的化合物及其应用 | |
CN114621296B (zh) | 有机金属配合物、制剂、有机光电器件及显示或照明装置 | |
CN114573594B (zh) | 一种二咔唑类化合物、有机电致发光器件和显示装置 | |
CN113416164B (zh) | 一种含咔唑的有机化合物及其应用 | |
CN113512043A (zh) | 有机化合物、制剂、有机发光器件和显示或照明装置 | |
CN113461548B (zh) | 一种芳香族胺类衍生物及其应用 | |
CN113563316A (zh) | 一种芳香族胺类衍生物及其应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20211019 |
|
RJ01 | Rejection of invention patent application after publication |