CN117069597B - Compound and application thereof - Google Patents
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- CN117069597B CN117069597B CN202311330195.1A CN202311330195A CN117069597B CN 117069597 B CN117069597 B CN 117069597B CN 202311330195 A CN202311330195 A CN 202311330195A CN 117069597 B CN117069597 B CN 117069597B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 36
- 239000000463 material Substances 0.000 claims abstract description 75
- 230000005525 hole transport Effects 0.000 claims abstract description 40
- 239000007787 solid Substances 0.000 abstract description 44
- -1 biaryl amine Chemical class 0.000 abstract description 4
- 230000002349 favourable effect Effects 0.000 abstract description 4
- 238000009825 accumulation Methods 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 230000007704 transition Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 126
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 50
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 32
- 239000000843 powder Substances 0.000 description 32
- 238000002347 injection Methods 0.000 description 29
- 239000007924 injection Substances 0.000 description 29
- 239000007795 chemical reaction product Substances 0.000 description 26
- 238000001953 recrystallisation Methods 0.000 description 26
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 25
- 239000008096 xylene Substances 0.000 description 25
- 238000001704 evaporation Methods 0.000 description 23
- 238000000034 method Methods 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- MYMYVYZLMUEVED-UHFFFAOYSA-N 2-bromo-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1Br MYMYVYZLMUEVED-UHFFFAOYSA-N 0.000 description 4
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 4
- 150000001924 cycloalkanes Chemical class 0.000 description 4
- 229910052805 deuterium Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000005580 triphenylene group Chemical group 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 150000004768 bromobenzenes Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- OMBGOMJNYDJOBM-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one Chemical compound C(C1=CC=CC=C1)=[C-]C(=O)C=CC1=CC=CC=C1 OMBGOMJNYDJOBM-UHFFFAOYSA-N 0.000 description 1
- WTAPZWXVSZMMDG-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WTAPZWXVSZMMDG-UHFFFAOYSA-N 0.000 description 1
- SHLSVXRREHLNCZ-UHFFFAOYSA-N 1-bromo-3-cyclopentyl-5-propan-2-ylbenzene Chemical compound CC(C)C1=CC(Br)=CC(C2CCCC2)=C1 SHLSVXRREHLNCZ-UHFFFAOYSA-N 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- QFUPJXCUNNWZJQ-UHFFFAOYSA-N 2-bromofluoren-1-one Chemical compound C1=CC=C2C3=CC=C(Br)C(=O)C3=CC2=C1 QFUPJXCUNNWZJQ-UHFFFAOYSA-N 0.000 description 1
- GUTJITRKAMCHSD-UHFFFAOYSA-N 9,9-dimethylfluoren-2-amine Chemical compound C1=C(N)C=C2C(C)(C)C3=CC=CC=C3C2=C1 GUTJITRKAMCHSD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 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
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 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
- 238000000605 extraction Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 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
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 238000012545 processing Methods 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
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- 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
- H10K50/15—Hole 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
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
-
- 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
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of organic light-emitting display, in particular to a compound, a hole transport material, an organic electroluminescent device and a display device. The invention provides a compound with a structural general formula shown in a formula (I). The compound has a parent structure of alkyl substituted biaryl amine, has high bond energy among atoms, good thermal stability, is favorable for solid accumulation among molecules, has strong hole transition capability, can effectively reduce the voltage of a device when being used as a hole transport material, and improves the service life of the material. The invention also provides a hole transport material, an organic electroluminescent device and a display device comprising the compound of the general formula (I).
Description
Technical Field
The invention relates to the technical field of organic light-emitting display, in particular to a compound, a hole transport material, an organic electroluminescent device and a display device.
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. Among them, the hole transport material, which is an important functional material, has a direct effect on the mobility of holes and ultimately affects the luminous efficiency of the OLED. However, the hole transport material applied to the OLED at present has low hole migration rate, poor energy level matching with the adjacent layer, and cannot give consideration to efficiency and service life, thus severely restricting the display function and development of the OLED display device.
Disclosure of Invention
The invention aims to provide a hole transport material which can improve the working efficiency and prolong the service life of an organic electroluminescent device.
In a first aspect the present invention provides a compound of formula (I):
（Ⅰ）
wherein,
R 1 ，R 2 independently of one another selected from hydrogen, C 1 -C 4 Alkanes, C 5 -C 30 Cycloalkane, C 6 -C 30 Aromatic groups or C of (2) 3 -C 30 And R is heteroaryl of 1 ，R 2 Can therebetweenCan be connected into a ring;
R 3 -R 7 independently of one another selected from hydrogen, deuterium, C 1 -C 4 Alkanes, C 5 -C 30 Cycloalkanes, and at least two are not hydrogen;
Ar 1 ，Ar 2 independently of one another selected from C 6 -C 30 Aromatic groups or C of (2) 10 -C 30 Heteroaryl of (a);
the heteroatoms on the heteroaryl groups are each independently selected from O, S or N;
the hydrogen atoms on the aryl and heteroaryl groups are each independently substituted with Ra, which Ra are each independently selected from deuterium, C 1 -C 4 Alkyl, C of (2) 5 -C 20 Cycloalkyl, phenyl, biphenyl, terphenyl or naphthyl.
In a second aspect, the present invention provides a hole transport material comprising at least one of the compounds provided in the first aspect of the present invention.
The third aspect of the present invention provides an organic electroluminescent device comprising at least one of the hole transport materials provided in the second aspect of the present invention.
A fourth aspect of the invention provides a display device comprising the organic electroluminescent device of the third aspect of the invention.
Compared with the prior art, the invention has the following technical effects:
the compound has a parent structure of alkyl substituted diarylamine, has high bond energy among atoms, good thermal stability, is favorable for solid accumulation among molecules, has strong hole transition capability, can effectively reduce the voltage of a device when used as a hole transport layer material, and improves the service life of the material.
The compound disclosed by the invention is applied to a hole transport layer, has a proper energy level with adjacent layers, is favorable for hole injection and migration, can effectively reduce driving voltage, has a higher hole migration rate, and can realize good luminous efficiency in a device.
The compound provided by the invention has a larger conjugate plane, is favorable for molecular accumulation, shows good thermodynamic stability, and shows long service life in a device.
Meanwhile, the preparation process of the compound is simple and feasible, raw materials are easy to obtain, and the compound is suitable for industrial production.
Drawings
Fig. 1 shows a schematic structural diagram of a typical organic electroluminescent device;
reference numerals:
1. a substrate; 2. a reflective anode electrode; 3. a hole injection layer; 4. a hole transport layer; 5. a light emitting layer; 6. an electron transport layer; 7. an electron injection layer; 8. and a cathode electrode.
Detailed Description
Further advantages and effects of the present invention will become apparent to those skilled in the art from the disclosure of the present specification, by describing the embodiments of the present invention with specific examples. While the description of the invention will be described in connection with the preferred embodiments, it is not intended to limit the inventive features to the implementation. Rather, the purpose of the invention described in connection with the embodiments is to cover other alternatives or modifications, which may be extended by the claims based on the invention. The following description contains many specific details for the purpose of providing a thorough understanding of the present invention. The invention may be practiced without these specific details. Furthermore, some specific details are omitted from the description in order to avoid obscuring the invention. It should be noted that, without conflict, the embodiments of the present invention and features of the embodiments may be combined with each other.
In a first aspect the present invention provides a compound of formula (I):
（I）
wherein,
R 1 ，R 2 independently of one another selected from hydrogen, C 1 -C 4 Alkanes, C 5 -C 30 Cycloalkane, C 6 -C 30 Aromatic groups or C of (2) 3 -C 30 And R is heteroaryl of 1 ，R 2 Can be connected into a ring;
R 3 -R 7 independently of one another selected from hydrogen, deuterium, C 1 -C 4 Alkanes, C 5 -C 30 Cycloalkanes, and at least two are not hydrogen;
Ar 1 ，Ar 2 independently of one another selected from C 6 -C 30 Aromatic groups or C of (2) 10 -C 30 Heteroaryl of (a);
the heteroatoms on the heteroaryl groups are each independently selected from O, S or N;
the hydrogen atoms on the aryl and heteroaryl groups are each independently substituted with Ra, which Ra are each independently selected from deuterium, C 1 -C 4 Alkyl, C of (2) 5 -C 20 Cycloalkyl, phenyl, biphenyl, terphenyl or naphthyl.
Preferably, said R 1 ，R 2 Independently of each other selected from the following groups unsubstituted or substituted by Ra: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, carbazolyl.
Preferably, the Ar 1 ，Ar 2 Independently of each other selected from the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, and carbazolyl.
Preferably, said R 3 -R 7 Independently of each other selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl.
More preferably, R 1 ，R 2 Independently of one another, from the group methyl, ethyl, isopropyl, the following radicals which are unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl and naphthaleneA group, a phenanthryl group, a triphenylene group, a fluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a9, 9-dimethylfluorenyl group, a spirofluorenyl group, an arylamino group, and a carbazolyl group.
The compound of formula (I) may be selected from the compounds shown in the following A1-A20:
in a second aspect, the present invention provides a hole transport material comprising at least one of the compounds provided in the first aspect of the present invention.
The third aspect of the present invention provides an organic electroluminescent device comprising at least one of the hole transport materials provided in the second aspect of the present invention.
In the present invention, the kind and structure of the organic electroluminescent device are not particularly limited as long as the hole transport material provided by the present invention can be used.
The organic electroluminescent device of the present invention may be a light emitting device of a top emission structure, for example, comprising an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a transparent or semitransparent cathode in this order on a substrate.
The organic electroluminescent device of the present invention may be a light emitting device having a bottom light emitting structure, for example, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode structure are sequentially formed on a substrate.
The organic electroluminescent device of the present invention may be a light emitting device of a double-sided light emitting structure, for example, a transparent or semitransparent anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a transparent or semitransparent cathode structure are sequentially included on a substrate.
In the organic electroluminescent device of the present invention, any material used for the layer in the prior art may be used for the other layers, except that the hole transport layer contains the hole transport material provided by the present invention.
Fig. 1 shows a schematic view of a typical organic electroluminescent device, in which a substrate 1, a reflective anode electrode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode electrode 8 are disposed in this order from bottom to top.
It will be appreciated that fig. 1 schematically illustrates only one typical organic electroluminescent device structure, and the present invention is not limited to this structure, and the hole transport material of the present invention may be used in any type of organic electroluminescent device. For example, the organic electroluminescent device may further include an electron blocking layer, a hole blocking layer, a light extraction layer, etc., and these layers may be added or omitted depending on the specific circumstances in practical applications.
For convenience, the organic electroluminescent device of the present invention will be described below with reference to fig. 1, but this is not meant to limit the scope of the present invention in any way. It is understood that all organic electroluminescent devices capable of using the hole transport material of the present invention are within the scope of the present invention.
In the present invention, the substrate 1 is not particularly limited, and a conventional substrate used in the organic electroluminescent device in the related art, for example, glass, polymer material, glass with TFT devices, polymer material, and the like can be used.
In the present invention, the material of the reflective anode electrode 2 is not particularly limited, and may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) Zinc oxide (ZnO), low Temperature Polysilicon (LTPS), etcThe transparent conductive material may be a metal material such as silver or an alloy thereof, aluminum or an alloy thereof, an organic conductive material such as PEDOT (poly 3, 4-ethylenedioxythiophene), or a multilayer structure of the above materials.
In the present invention, the material of the hole injection layer 3 is not particularly limited, and a hole injection material known in the art or a hole transport material provided by the present invention may be selected as the hole injection material.
For example, the material of the hole injection layer may be selected from at least one of the following HT-1 through HT-31 compounds:
in the present invention, the hole injection layer 3 may further include a p-type dopant, the kind of which is not particularly limited, and various p-type dopants known in the art may be employed, for example, the p-type dopant may be selected from at least one of the following compounds:
。
in the present invention, the amount of the p-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present invention, the hole transport layer 4 contains at least one of the hole transport materials of the present invention. The hole transport layer 4 may also comprise any combination of at least one of the hole transport materials of the present invention with a known hole transport material. The currently known hole transport material may be selected from at least one of the above-mentioned HT-1 through HT-31 compounds, but is not limited to the above-mentioned compounds.
In the present invention, the light emitting material of the light emitting layer 5 is not particularly limited, and any light emitting material known to those skilled in the art may be used, for example, the light emitting material may include a host material and a guest material. For example, the known host material of the light emitting layer may be selected from at least one of the following GPH-1 to GPH-80 compounds:
in a preferred embodiment of the present invention, the light-emitting layer 5 employs a phosphorescent electroluminescence technique. The guest material in its light emitting layer 5 is a phosphorescent dopant which may be selected from, but is not limited to, a combination of one or more of the following compounds:
，
the amount of the phosphorescent dopant is not particularly limited and may be an amount well known in the art.
In the present invention, the material of the electron transport layer 6 is not particularly limited, and may be made of an electron transport material known in the art. For example, the electron transport layer material may be selected from at least one of the following ET-1 to ET-57 compounds:
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in the present invention, the electron transport layer 6 may further include an n-type dopant, the kind of which is not particularly limited, and various n-type dopants known in the art may be employed. For example, the n-type dopant may be a compound represented by the formula:
。
in the present invention, the amount of the n-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present invention, the material of the electron injection layer 7 is not particularly limited, and electron injection materials known in the art may be used, for example, may include, but not limited to, liQ, liF, naCl, csF, li in the prior art 2 O、Cs 2 CO 3 At least one of materials such as BaO, na, li, ca.
In the present invention, the material of the cathode electrode 8 is not particularly limited, and may be selected from, for example, metals such as magnesium-silver mixture, liF/Al, ITO, al, metal mixtures, oxides, and the like.
The fourth aspect of the invention provides a display device comprising the organic electroluminescent device provided by the invention. Including but not limited to displays, televisions, tablet computers, mobile communication terminals, etc.
The method of preparing the organic electroluminescent device of the present invention is not particularly limited, and any method known in the art may be employed, for example, the present invention may be prepared by the following preparation method:
(1) Cleaning a reflective anode electrode 2 on an OLED device substrate 1 for top light emission, respectively performing steps of medicine washing, water washing, hairbrushes, high-pressure water washing, air knives and the like in a cleaning machine, and then performing heating treatment;
(2) Vacuum evaporating a hole injection material on the reflective anode electrode 2 as a hole injection layer 3;
(3) Vacuum evaporating a hole transport material on the hole injection layer 3 as a hole transport layer 4;
(4) Vacuum evaporating a light-emitting layer 5 on the hole transport layer 4, wherein the light-emitting layer 5 comprises a host material and a guest material;
(5) Vacuum evaporating an electron transport material on the light-emitting layer 5 as an electron transport layer 6;
(6) Vacuum evaporating electron injection material selected from LiQ, liF, naCl, csF, li as electron injection layer 7 on electron transport layer 6 2 O、Cs 2 CO 3 One or a combination of a plurality of materials such as BaO, na, li, ca;
(7) A cathode material is vacuum-evaporated on the electron injection layer 7 as a cathode electrode 8.
Only the structure of a typical organic electroluminescent device and a method for manufacturing the same are described above, and it should be understood that the present invention is not limited to such a structure. The hole transport material of the present invention may be used in any structure of organic electroluminescent device, and the organic electroluminescent device may be prepared using any preparation method known in the art.
The method for synthesizing the compound of the present invention is not particularly limited, and may be synthesized by any method known to those skilled in the art. The synthesis of the compounds of the present invention is illustrated below.
Synthesis example 1: synthesis of Compound A1
To the reaction flask were added 100mmol of aniline, 100mmol of 2-bromo-9, 9-dimethylfluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis dibenzylidene acetonate (Pd (dba)). 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 M1. Wherein, the addition amount of Pd (dba) is 1mol% of aniline.
To the reaction flask were added 100mmol of M1, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M2. Wherein, the addition amount of Pd (dba) is 1mol% of M1.
Into a reaction flask were charged 100mmol of M2, 100mmol of pinacol biborate, 41.4g of potassium carbonate (300 mmol), 800ml of toluene, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 120℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M3. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M2.
To the reaction flask were added 100mmol of aniline, 100mmol of 2, 6-dimethylbromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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, the addition amount of Pd (dba) is 1mol% of aniline.
To the reaction flask were added 100mmol of M4, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M5. Wherein, the addition amount of Pd (dba) is 1mol% of M4.
To the reaction flask were added 100mmol of M3, 100mmol of M5, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 A1. Wherein, the addition amount of Pd (dba) is 1mol% of M3.
1 H NMR (400 MHz, Chloroform ) δ 7.92(d,J= 6.8 Hz, 1H), 7.84(d,J= 8.8 Hz, 1H),7.61-7.48 (m, 6H), 7.41-7.30 (m, 5H), 7.29-7.17 (m, 6H), 7.10-6.96 (m, 9H), 2.13 (s, 6H), 1.69 (s, 6H).
M/Z: experimental values, 633.1; theoretical value, 632.3.
Synthesis example 2: synthesis of Compound A5
Into the reaction flask were charged 100mmol of 2-bromofluorenone, 800ml of THF, and 100mmol of methyl magnesium bromide at 0℃were added dropwise. After the dripping is finished, naturally heating to room temperature, and reacting for 12 hours. Stopping the reaction after the reaction, adding water, separating liquid, washing an organic phase with water, concentrating, and recrystallizing and purifying the obtained solid by using toluene to obtain white powder M1.
Into the reaction flask were charged 100mmol of M1, 100mmol of acetic acid and 800ml of benzene, and the mixture was reacted at 120℃for 12 hours. 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 M2.
To the reaction flask were added 100mmol of aniline, 100mmol of M2, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M3. Wherein, the addition amount of Pd (dba) is 1mol% of aniline.
To the reaction flask were added 100mmol of M3, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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, the addition amount of Pd (dba) is 1mol% of M3.
Into a reaction flask were charged 100mmol of M4, 100mmol of pinacol biborate, 41.4g of potassium carbonate (300 mmol), 800ml of toluene, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 120℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M5. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M4.
To the reaction flask were added 100mmol of aniline, 100mmol of 2, 6-dimethylbromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M6. Wherein, the addition amount of Pd (dba) is 1mol% of aniline.
To the reaction flask were added 100mmol of M6, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M7. Wherein, the addition amount of Pd (dba) is 1mol% of M6.
To the reaction flask were added 100mmol of M5, 100mmol of M7, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis dibenzylidene acetonide (Pd (dba)). 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, the addition amount of Pd (dba) is 1mol% of M5.
1 H NMR (400 MHz, Chloroform ) δ 7.94 (d,J= 7.2 Hz, 1H), 7.86 (d,J= 9.2 Hz, 1H), 7.58-7.47 (m, 6H), 7.40-7.32 (m, 5H), 7.29-7.18 (m, 10H), 7.08 (d,J= 6.8 Hz, 6H), 7.01 (t,J= 7.2 Hz, 4H), 2.28 (s, 3H), 2.13 (s, 6H).
M/Z: experimental values, 695.4; theoretical value, 694.3.
Synthesis example 3: synthesis of Compound A9
To the reaction flask were added 100mmol of aniline, 100mmol of 2-bromo-9, 9-dimethylfluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis dibenzylidene acetonate (Pd (dba)). 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 M1. Wherein, the addition amount of Pd (dba) is 1mol% of aniline.
To the reaction flask were added 100mmol of M1, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M2. Wherein, the addition amount of Pd (dba) is 1mol% of M1.
Into a reaction flask were charged 100mmol of M2, 100mmol of pinacol biborate, 41.4g of potassium carbonate (300 mmol), 800ml of toluene, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 120℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M3. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M2.
To the reaction flask were added 100mmol of 2-naphthylamine, 100mmol of 2, 6-dimethylbromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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, the addition amount of Pd (dba) is 1mol% of 2-naphthylamine.
To the reaction flask were added 100mmol of M4, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M5. Wherein, the addition amount of Pd (dba) is 1mol% of M4.
To the reaction flask were added 100mmol of M3, 100mmol of M5, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 A9. Wherein, the addition amount of Pd (dba) is 1mol% of M3.
1 H NMR (400 MHz, Chloroform ) δ 7.92 (d,J= 7.2 Hz, 1H), 7.84 (d,J= 9.2 Hz, 1H),7.70 (d,J= 7.2 Hz, 1H),7.64 (d,J= 7.2 Hz, 1H),7.58-7.50 (m, 7H), 7.47-7.30 (m, 8H), 7.25 (t,J= 7.2 Hz, 3H), 7.15-6.96 (m, 8H), 2.13 (s, 6H), 1.69 (s, 6H).
M/Z: experimental values, 683.3; theoretical value, 682.3.
Synthesis example 4: synthesis of Compound A14
To the reaction flask were added 100mmol of aniline, 100mmol of 2-bromo-9, 9-dimethylfluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis dibenzylidene acetonate (Pd (dba)). 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 M1. Wherein, the addition amount of Pd (dba) is 1mol% of aniline.
To the reaction flask were added 100mmol of M1, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M2. Wherein, the addition amount of Pd (dba) is 1mol% of M1.
Into a reaction flask were charged 100mmol of M2, 100mmol of pinacol biborate, 41.4g of potassium carbonate (300 mmol), 800ml of toluene, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ). The reaction was carried out at 120℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M3. Wherein Pd (PPh) 3 ) 4 The amount of (2) added was 1mol% of M2.
To the reaction flask were added 100mmol of aniline, 100mmol of 3-isopropyl-5-cyclopentyl bromobenzene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of palladium bis dibenzylidene acetonate (Pd (dba)). 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, the addition amount of Pd (dba) is 1mol% of aniline.
To the reaction flask were added 100mmol of M4, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M5. Wherein, the addition amount of Pd (dba) is 1mol% of M4.
To the reaction flask were added 100mmol of M3, 100mmol of M5, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 a14. Wherein, the addition amount of Pd (dba) is 1mol% of M3.
1H NMR (400 MHz, Chloroform ) δ 7.92 (d, J = 6.8 Hz, 1H), 7.86 (d, J = 6.8 Hz, 1H), 7.55 (d, J = 7.6Hz, 4H), 7.50 (t, J = 6.8 Hz, 2H),7.41-7.30 (m, 7H), 7.28-7.20 (m, 6H), 7.08 (d, J = 7.2Hz, 4H), 7.00 (t, J = 7.2 Hz, 2H), 6.80 (s, 1H), 2.92-2.70(m, 2H), 2.10-1.91 (m, 2H), 1.85-1.60 (m, 12H), 1.22 (s, 6H).
M/Z: experimental values, 715.6; theoretical value, 714.4.
Synthesis example 5: synthesis of Compound A15
To the reaction flask were added 100mmol of deuterated bromobenzene, 100mmol of 2-amino-9, 9-dimethylfluorene, 28.83g of sodium tert-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis dibenzylideneacetone palladium (Pd (dba)). 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 M1. Wherein, the addition amount of Pd (dba) is 1mol% of deuterated bromobenzene.
To the reaction flask were added 100mmol of M1, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M2. Wherein, the addition amount of Pd (dba) is 1mol% of M1.
To the reaction flask were added 100mmol of M2, 100mmol of pinacol biborate, 41.4g of potassium carbonate (300 mmol), 800ml of toluene, and 1mol% of tetrakis (triphenylphosphine) palladium (Pd (PPh 3) 4). The reaction was carried out at 120℃for 12h. After the reaction, the reaction is stopped, the reactant is cooled to room temperature, water is added, the organic phase is concentrated to obtain white solid, the white solid is filtered and washed, and the obtained solid is recrystallized and purified by toluene to obtain white powder M3. Wherein, the addition amount of Pd (PPh 3) 4 is 1mol% of M2.
To the reaction flask were added 100mmol of aniline, 100mmol of 2, 6-dimethylbromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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, the addition amount of Pd (dba) is 1mol% of aniline.
To the reaction flask were added 100mmol of M4, 100mmol of p-chlorobromobenzene, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 M5. Wherein, the addition amount of Pd (dba) is 1mol% of M4.
To the reaction flask were added 100mmol of M3, 100mmol of M5, 28.83g of sodium t-butoxide (300 mmol), 800ml of xylene, and 1mol% of bis-dibenzylideneacetone palladium (Pd (dba)). 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 a15. Wherein, the addition amount of Pd (dba) is 1mol% of M3.
1H NMR (400 MHz, Chloroform ) δ 7.90 (d, J = 7.2 Hz, 1H), 7.86 (d, J = 9.6 Hz, 1H),7.55 (d, J = 7.6 Hz, 4H), 7.49 (d, J = 7.2 Hz, 1H), 7.41-7.28 (m, 6H), 7.24 (t, J = 7.2 Hz, 4H), 7.11-7.03 (m, 6H), 2.18 (s, 6H), 1.69 (s, 6H).
M/Z: experimental value, 638.2; theoretical value, 637.3.
Other compounds of the present invention can be synthesized by selecting appropriate raw materials according to the ideas of the above synthesis examples 1 to 5, or by selecting any other appropriate methods and raw materials.
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 A1 material on the hole injection layer to serve as a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 80nm;
vacuum evaporating a light-emitting layer on the hole transmission layer, wherein the light-emitting 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 luminescent layer, wherein a material ET-32 is selected as the electron transport material, the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 30nm;
vacuum evaporating LiF with the thickness of 0.5nm on an Electron Transport Layer (ETL) as an electron injection layer, wherein the evaporation rate is 0.1nm/s;
finally, an aluminum layer with the thickness of 150 nm is evaporated on the electron injection layer to serve as a cathode of the organic electroluminescent device, and the evaporation rate is 0.1nm/s.
Examples 2 to 5
The procedure of example 1 was repeated except that A5, A9, A14 and A15 were used in place of A1. The test results are shown in Table 1.
Comparative example 1
The test results are shown in Table 1, except that HT-7 is used in place of A1, which is the same as in example 1.
HT-7
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.
TABLE 1 organic electroluminescent device Performance results
As can be seen from the data in the table, the compound prepared by the invention is used for the hole transport material of the organic electroluminescent device, can effectively reduce the driving voltage of the organic electroluminescent device, improve the current efficiency, prolong the service life of the device, and is a hole transport material with good performance.
The foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and scope of the invention are intended to be included within the scope of the invention.
Claims (4)
1. A compound selected from the group consisting of the following structural formulas:
。
2. a hole transport material comprising at least one compound of claim 1.
3. An organic electroluminescent device comprising at least one of the hole transport materials of claim 2.
4. A display device characterized by comprising the organic electroluminescent device of claim 3.
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| WO2013002514A2 (en) * | 2011-06-29 | 2013-01-03 | 덕산하이메탈(주) | Organic electroluminescence device using diarylamine derivatives, and novel compound and composition for organic electroluminescence device |
| KR20190124620A (en) * | 2018-04-26 | 2019-11-05 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| CN111094465A (en) * | 2018-05-30 | 2020-05-01 | 株式会社Lg化学 | Coating composition, organic light emitting diode using the same, and method of manufacturing the same |
| KR20210026941A (en) * | 2019-09-02 | 2021-03-10 | 주식회사 엘지화학 | Organic light emitting device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013002514A2 (en) * | 2011-06-29 | 2013-01-03 | 덕산하이메탈(주) | Organic electroluminescence device using diarylamine derivatives, and novel compound and composition for organic electroluminescence device |
| KR20190124620A (en) * | 2018-04-26 | 2019-11-05 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| CN111094465A (en) * | 2018-05-30 | 2020-05-01 | 株式会社Lg化学 | Coating composition, organic light emitting diode using the same, and method of manufacturing the same |
| KR20210026941A (en) * | 2019-09-02 | 2021-03-10 | 주식회사 엘지화학 | Organic light emitting device |
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