CN111303187B - Organic luminescent material and organic electroluminescent device - Google Patents
Organic luminescent material and organic electroluminescent device Download PDFInfo
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- CN111303187B CN111303187B CN202010219338.1A CN202010219338A CN111303187B CN 111303187 B CN111303187 B CN 111303187B CN 202010219338 A CN202010219338 A CN 202010219338A CN 111303187 B CN111303187 B CN 111303187B
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- organic electroluminescent
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- electroluminescent device
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- 239000000463 material Substances 0.000 title claims abstract description 69
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 abstract description 2
- 229960005544 indolocarbazole Drugs 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- -1 C 1 -C 4 Alkyl Chemical group 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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- 238000004809 thin layer chromatography Methods 0.000 description 13
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- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 5
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- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 125000002098 pyridazinyl group Chemical group 0.000 description 5
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- XEFCWBLINXJUIV-UHFFFAOYSA-N acetic acid;iodobenzene Chemical compound CC(O)=O.CC(O)=O.IC1=CC=CC=C1 XEFCWBLINXJUIV-UHFFFAOYSA-N 0.000 description 4
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- VWMQXAYLHOSRKA-UHFFFAOYSA-N 5-chloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC=NC2=C1 VWMQXAYLHOSRKA-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
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- 238000005516 engineering process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 239000012074 organic phase Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 1
- XHWREMMBFABHIJ-UHFFFAOYSA-N 2H-triazolo[4,5-f]quinazoline Chemical compound N1N=NC=2C1=C1C=NC=NC1=CC=2 XHWREMMBFABHIJ-UHFFFAOYSA-N 0.000 description 1
- SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
- 102100024049 A-kinase anchor protein 13 Human genes 0.000 description 1
- 101100269519 Homo sapiens AKAP13 gene Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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Abstract
The application provides a novel organic luminescent material, which has a structure shown in a general formula (I) and can be used for organic electroluminescent devices and electron transport layer materials. The present application also provides an organic electroluminescent device comprising the novel organic luminescent material of the present application. The organic luminescent material disclosed by the application has a parent structure of indolocarbazole, has high bond energy among atoms, has good thermal stability, is favorable for solid accumulation among molecules, and can effectively prolong the service life of the material when being used as a luminescent layer material. Meanwhile, the preparation process of the derivative is simple and feasible, raw materials are easy to obtain, and the derivative is suitable for industrial production.
Description
Technical Field
The present application relates to a novel organic compound, and in particular to an organic light emitting material and an organic electroluminescent device using the same.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light under the excitation of electric current and electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (OLED) has the advantages of self-luminescence, low voltage DC drive, full solidification, wide viewing angle, light weight, simple composition and process, etc., compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, has large viewing angle and low power, the response speed can reach 1000 times of the liquid crystal display, and the manufacturing cost is lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advancement of OLED technology in the two fields of illumination and display, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is usually the result of the optimized collocation of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, film can be formed on any substrate by a vapor deposition or spin coating method, and flexible display and large-area display can be realized; the optical property, the electrical property, the stability and the like of the material can be adjusted by changing the structure of the molecule, and the material has a large space to select. In the most common OLED device structures, the following classes of organic materials are typically included: a hole injection material, a hole transport material, an electron transport material, a light emitting material (dye or doped guest material) of each color, a corresponding host material, and the like. Phosphorescent host materials currently used tend to have a single carrier transporting capability, such as a hole-type transporting host and an electron-type transporting host, but the single carrier transporting capability can cause electron and hole mismatch in the light-emitting layer, resulting in severe efficiency roll-off and reduced lifetime.
CN109824672a discloses a structure of quinazolinotriazole as an electron transport material, and the electron mobility of the material has room for improvement.
Disclosure of Invention
To this end, an object of the present application is to provide an organic light emitting material, and an organic electroluminescent device using the same.
A first aspect of the present application provides an organic light-emitting material, characterized by having a structure represented by the following general formula (i):
L-Ar 2
(II)
wherein,,
Ar 1 selected from C unsubstituted or substituted by Ra 6 -C 30 C, unsubstituted or substituted by Ra 3 -C 30 Heteroaryl of (a);
R 1 -R 4 are identical to or different from each other and are independently selected from hydrogen, deuterium, C 1 -C 10 Alkyl, C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl, and R 1 Is linked to a compound of formula (II) wherein adjacent R 1 -R 4 Can be connected into a ring;
l is selected from chemical bond, C 6 -C 30 Or C 3 -C 30 Is a heteroarylene group;
Ar 2 selected from C5-C20 nitrogen-containing heteroaryl groups;
x is selected from O, S, CR 5 R 6 、NR 7 ；R 5 、R 6 Independently selected from C 1 -C 10 Alkyl, C 1 -C 6 Cycloalkyl, C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl; r is R 7 Selected from C unsubstituted or substituted by Ra 6 -C 30 Aryl, C unsubstituted or substituted by Ra 3 -C 30 Heteroaryl;
the substituents Ra of the individual radicals, which may be identical or different, are independently of one another selected from hydrogen, halogenPlain, nitro, cyano, C 1 -C 4 Alkyl, phenyl, biphenyl, terphenyl or naphthyl.
Preferably Ar 1 Selected from the following substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazolyl.
Preferably, said R 1 -R 4 Independently of each other, selected from hydrogen, deuterium, methyl, ethyl, the following groups, unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
Preferably, R 5 And R is 6 Independently of one another, from the group methyl, ethyl, cyclopentyl, cyclohexyl, the following radicals, which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
Preferably, R 7 Selected from the group consisting of unsubstituted or Ra-substituted radicals: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazole groups.
Preferably Ar 2 Independently of each other, selected from pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl.
Preferably, L is selected from a bond, or a subunit of the following compounds, unsubstituted or substituted with Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, carbazole.
More preferably, the organic luminescent material is selected from the group consisting of compounds represented by A1-a 36:
the second aspect of the present application also provides an organic electroluminescent device comprising the organic luminescent material of the present application.
The organic luminescent material can be used as an electron transport material in an organic electroluminescent device.
The organic luminescent material disclosed by the application has a parent structure of indolocarbazole, has high bond energy among atoms, has good thermal stability, is favorable for solid accumulation among molecules, and can effectively prolong the service life of the material when being used as a luminescent layer material.
The aromatic amine substituted indolo heterocyclic derivative is applied to a light-emitting layer, has a proper energy level with adjacent layers, is favorable for injection of holes and electrons, can effectively reduce the starting voltage, and meanwhile has higher exciton migration rate, so that good light-emitting efficiency can be realized in a device. The compound has a larger conjugation plane, is favorable for molecular accumulation, shows good thermodynamic stability, and shows long service life in a device.
Meanwhile, the preparation process of the derivative is simple and feasible, raw materials are easy to obtain, and the derivative is suitable for industrial production.
Detailed Description
The organic luminescent material can be used as an electron transport material in an organic electroluminescent device.
In the present application, the kind and structure of the organic electroluminescent device are not particularly limited as long as the organic luminescent material provided in the present application can be used. For convenience, the present application will be described with respect to an organic light emitting diode, but this is not meant to limit the scope of the present application in any way. It is understood that all organic electroluminescent devices capable of using the organic luminescent materials of the present application are within the scope of the present application.
In general, an organic light emitting diode includes first and second electrodes on a substrate, and an organic material layer between the electrodes, and the organic material layer may have a multi-layered structure. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
In the present application, the substrate is not particularly limited, and conventional substrates used in the organic electroluminescent device in the related art, for example, glass, polymer materials, glass with TFT devices, polymer materials, and the like can be used.
In the present application, the anode material is not particularly limited, and may be Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) Transparent conductive material such as zinc oxide (ZnO)The material may be silver or an alloy thereof, aluminum or an alloy thereof, or an organic conductive material such as PEDOT, a multilayer structure of the above materials, or the like.
In the present application, the cathode material is not particularly limited, and may be selected from, for example, materials such as magnesium silver mixture, liF/Al, ITO, etc., metal mixtures, oxides, etc.
In this application, the organic electroluminescent diode (OLED) may further include a hole injection layer, a hole transport layer, etc. between the light emitting layer and the anode, and these layers may be used, but are not limited to, at least one of HT1 to HT31 listed below, and these materials may be used singly or in combination of two or more.
In the present application, the device light-emitting layer may comprise a host material and a light-emitting dye, wherein the host material includes, but is not limited to, a combination of one or more of the conventional materials shown in GPH1-GPH80, below.
In a preferred embodiment of the present application, the light-emitting layer employs phosphorescent electroluminescence technology. The light emitting layer thereof is doped with a phosphorescent dopant which may be selected from, but is not limited to, one or more combinations of the below listed RPD-1 through RPD-28.
Electron transport materials include, but are not limited to, combinations of one or more of the ET1-ET57 materials listed below. The electron transport materials of the present application may be used in combination with one or more of these materials.
In addition, the OLED device may further include an electron injection layer between the electron transport layer and the cathode, the material of the electron injection layer is not particularly limited, and may include, for example, liQ, liF, naCl, csF, li in the prior art 2 O、Cs 2 CO 3 BaO, na, li, ca, etc. or a combination of several materials.
In the present application, the following materials were used for comparison experiments with the organic light emitting materials of the present application.
The method for synthesizing the compound of the present application is not particularly limited, and may be synthesized by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present application.
Synthetic examples
Synthesis example 1: synthesis of Compound A2
100mmol of 5-chlorobenzoxazole is dissolved in 300ml of dichloromethane, 100mmol of bromine is added dropwise at the temperature of 0 ℃ for 3 hours, water is added after the reaction is finished, and an organic phase is washed with water and concentrated to obtain an intermediate M1.
M1 (1000 mmol,1.0 eq) and methylene chloride (2000 ml) were added to a 10L three-necked flask, and the solution was stirred. The reaction was completed by pouring triethylamine 416mL (3000 mmol,3.0 eq) at a controlled temperature below 10deg.C, dropping hydrazine hydrate 93.75g (1500 mmol,1.5 eq) and then naturally warming to room temperature for 1 hour, and monitoring the reaction by Thin Layer Chromatography (TLC). Adding 4000ml of pure water, stirring for 30 minutes, and then carrying out suction filtration; the obtained solid was added to a 4000ml beaker containing 2000ml of pure water, stirred for 10 minutes, suction-filtered and dried to obtain a white solid M2.
Benzaldehyde (175.8 mmol,1.1 eq), intermediate M2 (159.8 mmol,1.0 eq) and 1000ml ethanol were added to a single vial, stirred until the solution was clear and stirring continued for 30 minutes, TLC monitored for disappearance of starting material. 57g (175.8 mmol,1.1 eq) of iodobenzene diacetic acid are added in portions, then stirred for 1 hour, the solid gradually separates out, after the TLC monitoring reaction is finished, the filter cake is filtered, the filter cake is rinsed with ethanol, and the filter cake is washed until the filtrate is colorless clear liquid, thus obtaining brown solid M3.
Into a reaction flask were charged 100mmol of M3, 100mmol of M4, 40g of potassium carbonate (300 mmol), 800ml DMF and 200ml water, and 1mol% Pd (PPh) 3 ) 4 . The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder A2. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% of M3 and M4.
1 H NMR(400MHz,Chloroform)δ8.50–8.34(m,6H),8.28(s,1H),7.79(d,J＝12.0Hz,4H),7.70(s,1H),7.59(d,J＝13.2Hz,4H),7.50(m,6H).
Synthesis example 2: synthesis of Compound A5
100mmol of 5-chlorobenzoxazole is dissolved in 300ml of dichloromethane, 100mmol of bromine is added dropwise at the temperature of 0 ℃ for 3 hours, water is added after the reaction is finished, and an organic phase is washed with water and concentrated to obtain an intermediate M1.
M1 (1000 mmol,1.0 eq) and methylene chloride (2000 ml) were added to a 10L three-necked flask, and the solution was stirred. Controlling the temperature below 10 ℃, pouring 416mL (3000 mmol,3.0 eq) of triethylamine, controlling the temperature below 10 ℃, dropwise adding 93.75g (1500 mmol,1.5 eq) of hydrazine hydrate, naturally heating to room temperature after the dropwise adding, reacting for 1 hour, and monitoring the reaction by TLC. Adding 4000ml of pure water, stirring for 30 minutes, and then carrying out suction filtration; adding the obtained solid into 4000ml beaker containing 2000ml pure water, stirring for 10 min, suction filtering, and oven drying to obtain white solid M2
Benzaldehyde (175.8 mmol,1.1 eq), M2 (159.8 mmol,1.0 eq) and 1000ml ethanol were added to a single vial, stirred until the solution was clear and stirring continued for 30 minutes, TLC monitoring the disappearance of starting material. 57g (175.8 mmol,1.1 eq) of iodobenzene diacetic acid are added in portions, after the addition is completed, the mixture is stirred for 1 hour, the solid is gradually separated out, after the TLC monitoring reaction is finished, the mixture is filtered, the filter cake is leached by ethanol, and the filter cake is washed until the filtrate is colorless clear liquid, thus obtaining brown solid M3.
Into a reaction flask were charged 100mmol of intermediate M3, 120mmol of pinacol biborate, 300mmol of potassium acetate, 800ml of DMF, followed byInto 1mol% Pd (dppf) Cl 2 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder M4. Wherein Pd (dppf) Cl 2 The amount of (2) added was 1mol% of M3.
Into a reaction flask were charged 100mmol of M4, 100mmol of 2-chloro-4-phenylquinazoline, 40g of potassium carbonate (300 mmol), 800ml of DMF and 200ml of water, followed by 1% Pd (PPh 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder A5. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M4.
1 H NMR(CDCl3,400MHz)δ8.35(s,1H),8.28(s,1H),8.11(d,J＝10.0Hz,2H),7.78(d,J＝8.4Hz,2H),7.57(dd,J＝10.0,8.4Hz,4H),7.49(m,6H).
Synthesis example 3: synthesis of Compound A16
Into a 10L three-necked flask, 2-bromo-5-chloro-3, 3-dimethylindole (1000 mmol,1.0 eq) and methylene chloride (2000 ml) were charged, and the solution was stirred. Controlling the temperature to be lower than 10 ℃, pouring 416mL (3000 mmol,3.0 eq) of triethylamine, controlling the temperature to be lower than 10 ℃, dropwise adding 93.75g (1500 mmol,1.5 eq) of hydrazine hydrate, naturally heating to room temperature after the dropwise adding, reacting for 1 hour, and monitoring the reaction by TLC. Adding 4000ml of pure water, stirring for 30 minutes, and then carrying out suction filtration; the obtained solid was added to a 4000ml beaker containing 2000ml of pure water, stirred for 10 minutes, suction-filtered and dried to obtain a white solid M1.
Benzaldehyde (175.8 mmol,1.1 eq), M1 (159.8 mmol,1.0 eq) and 1000ml ethanol were added to a single vial, stirred until the solution was clear and stirring continued for 30 minutes, TLC monitoring the disappearance of starting material. 57g (175.8 mmol,1.1 eq) of iodobenzene diacetic acid are added in portions, after the addition is completed, the mixture is stirred for 1 hour, the solid is gradually separated out, after the TLC monitoring reaction is finished, the mixture is filtered, the filter cake is leached by ethanol, and the filter cake is washed until the filtrate is colorless clear liquid, thus obtaining brown solid M2.
Into a reaction flask were charged 100mmol of M2, 100mmol of M3, 40g (300 mmol) of potassium carbonate, 800ml of DMF, 200ml of water, followed by 1mol% of Pd (PPh) 3 ) 4 The reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder a16. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M2.
1 H NMR(CDCl3,400MHz)δ8.36(m,4H),8.28(s,2H),,7.50(m,10H),7.24(s,2H),1.74(s,6H).
Synthesis example 4: synthesis of Compound A25
A10L three-necked flask was charged with the starting material M (1000 mmol,1.0 eq) and 2000ml of methylene chloride, and the solution was stirred. Controlling the temperature to be lower than 10 ℃, pouring 416mL (3000 mmol,3.0 eq) of triethylamine, controlling the temperature to be lower than 10 ℃, dropwise adding 93.75g (1500 mmol,1.5 eq) of hydrazine hydrate, naturally heating to room temperature after the dropwise adding, reacting for 1 hour, and monitoring the reaction by TLC. Adding 4000ml of pure water, stirring for 30 minutes, and then carrying out suction filtration; the obtained solid was added to a 4000ml beaker containing 2000M pure water, stirred for 10 minutes, suction-filtered and dried to obtain a white solid M1.
Benzaldehyde (175.8 mmol,1.1 eq), M1 (159.8 mmol,1.0 eq) and 1000ml ethanol were added to a single vial, stirred until the solution was clear and stirring continued for 30 minutes, TLC monitoring the disappearance of starting material. 57g (175.8 mmol,1.1 eq) of iodobenzene diacetic acid are added in portions, after the addition is completed, the mixture is stirred for 1 hour, the solid is gradually separated out, after the TLC monitoring reaction is finished, the mixture is filtered, the filter cake is leached by ethanol, and the filter cake is washed until the filtrate is colorless clear liquid, thus obtaining brown solid M2.
In a reaction flask, 100mmol of M2, 100mmol of M3, 40g (300 mmol) of potassium carbonate, 800ml of DMF, 200ml of water and 1% of Pd (PPh) were added 3 ) 4 In the followingThe reaction was carried out at 120℃for 12h. After the reaction, the reaction was stopped, and the reaction product was cooled to room temperature, water was added, filtered, and washed with water, and the obtained solid was purified by recrystallization with toluene to obtain white powder a25. Wherein Pd (PPh) 3 ) 4 The amount of (C) added was 1mol% of M2 and M3.
1 H NMR(CDCl3,400MHz)δ.8.40–8.33(m,6H),8.28(s,2H),8.18(s,1H),8.07(d,J＝12.0Hz,2H),7.78(s,1H),7.69(d,J＝11.6Hz,2H),7.61(s,1H),7.50(m,9H),1.69(s,6H).
Other compounds of the present application can be synthesized by selecting appropriate starting materials according to the concepts of examples 1-4, and any other appropriate methods and starting materials can be selected for synthesis.
The second aspect of the present application also provides an organic electroluminescent device comprising the organic luminescent material provided herein.
In the present application, the method of manufacturing the OLED device is not particularly limited, and may be manufactured using any method known in the art.
Example 1
Ultrasonic treating the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in an acetone-ethanol mixed solvent, baking in a clean environment until water is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam;
placing the above glass substrate with anode in vacuum cavity, and vacuumizing to less than 10 -5 Vacuum evaporating HT-11 on the anode layer film as a hole injection layer at an evaporation rate of 0.1nm/s and an evaporation film thickness of 10nm;
vacuum evaporating HT-5 material on the hole injection layer as a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80nm;
vacuum evaporating a luminescent layer of the device on the hole transport layer, wherein the luminescent layer comprises a main material GHP-16 and a dye material RPD-1, evaporating by utilizing a multi-source co-evaporation method, adjusting the evaporation rate of the main material GHP-16 to be 0.1nm/s, wherein the evaporation rate of the dye RPD-1 is 3% of the evaporation rate of the main material, and the total evaporation film thickness is 30nm;
vacuum evaporating an electron transport layer on the light-emitting layer, wherein a material A2 is selected as the electron transport material, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
LiF with the thickness of 0.5nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent devices prepared in examples and comparative examples were measured using a digital source meter and a luminance meter at the same luminance, specifically, the luminance of the organic electroluminescent devices was measured to be 5000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; the lifetime test of LT95 is as follows: at 5000cd/m using a luminance meter 2 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 4750cd/m 2 Time in hours.
Examples 2 to 6
The organic light-emitting materials A5, a13, a25, a27 and a35 of the present application were used as electron-transporting materials, respectively, and the rest was the same as in example 1. The test results are shown in Table 1.
Comparative example
The remainder was the same as in example 1, except that R1 was used as the electron transporting material, and the test results are shown in Table 1.
TABLE 1 organic electroluminescent device Performance results
From the data in the table, the novel organic material prepared by the application is used for the electron transport material of the organic electroluminescent device, can effectively reduce the voltage at take off and land, improve the current efficiency, prolong the service life of the device and is an electron transport material with good performance.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While nevertheless, obvious variations or modifications may be made to the embodiments described herein without departing from the scope of the invention.
Claims (3)
1. An organic light emitting material, wherein the organic light emitting material is selected from the group consisting of compounds shown below:
2. an organic electroluminescent device comprising the organic luminescent material according to claim 1.
3. The organic electroluminescent device according to claim 2, wherein the organic luminescent material is used as an electron transport material.
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