CN114874231A - Organic electroluminescent compound and application thereof - Google Patents
Organic electroluminescent compound and application thereof Download PDFInfo
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- CN114874231A CN114874231A CN202110164584.6A CN202110164584A CN114874231A CN 114874231 A CN114874231 A CN 114874231A CN 202110164584 A CN202110164584 A CN 202110164584A CN 114874231 A CN114874231 A CN 114874231A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 62
- 239000010410 layer Substances 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 230000005525 hole transport Effects 0.000 claims description 16
- 239000002346 layers by function Substances 0.000 claims description 9
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- -1 o-dimethylphenyl Chemical group 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical group [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 1
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- WWPQNEPYSDNRBX-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=CC=CC=C3[S+]2I Chemical compound C1=CC=C2C(=C1)C3=CC=CC=C3[S+]2I WWPQNEPYSDNRBX-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VNBFIQCGIGVCJR-UHFFFAOYSA-N boronooxyboronic acid;2,3-dimethylbutane-2,3-diol Chemical compound OB(O)OB(O)O.CC(C)(O)C(C)(C)O.CC(C)(O)C(C)(C)O VNBFIQCGIGVCJR-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 208000027385 essential tremor 2 Diseases 0.000 description 1
- 208000031534 hereditary essential 2 tremor Diseases 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—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
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
- C09K2211/1077—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with oxygen
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
- C09K2211/1081—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with sulfur
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention provides an organic electroluminescent compound and application thereof, wherein the organic electroluminescent compound has a structure shown in a formula I. The organic electroluminescent compound provided by the invention can provide excellent OLED device performance, so that the OLED device has lower driving voltage and higher efficiency.
Description
Technical Field
The invention belongs to the field of electroluminescent materials, and relates to an organic electroluminescent compound and application thereof.
Background
In OLED devices, a Hole Injection Layer (HIL) and a Hole Transport Layer (HTL) are typically disposed between the anode and the light-emitting layer to achieve hole transport from the anode to the light-emitting layer. In order to achieve low device driving voltage and high efficiency, a hole transport material having a minimum charge injection barrier and suitable hole transport ability is particularly important.
Therefore, in the art, it is desired to develop an organic electroluminescent compound and its application.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an organic electroluminescent compound and application thereof. The organic electroluminescent compound provided by the invention can provide excellent OLED device performance, so that the OLED device has lower driving voltage and higher efficiency.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides an organic electroluminescent compound having a structure represented by formula I below:
wherein X may be O, S, or
Ar 1 And Ar 2 Each independently is an aromatic hydrocarbon group or an aromatic heterocyclic group, L 1 Represents a single bond, a 2-valent aromatic hydrocarbon group or a 2-valent aromatic heterocyclic group, R 1 And R 2 Independently selected from hydrogen atom, heavy hydrogen atom, fluorine atom, chlorine atom, cyano-group, nitro-group, alkyl group with 1-6 carbon atoms, cycloalkyl group with 5-10 carbon atoms, alkenyl group with 2-6 carbon atoms, alkoxy group with 1-6 carbon atoms, cycloalkoxy group with 5-10 carbon atoms, aromatic hydrocarbon group or aromatic heterocyclic group; r 3 、R 4 Each independently selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms or substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms; r 3 And R 4 Optionally linked to form a ring; m and n are each independently 0, 1 or 2.
In the invention, the organic electroluminescent compound contains a thiophene triarylamine structure, and can provide excellent OLED device performance, such as lower driving voltage and higher efficiency.
Preferably, Ar is 1 And Ar 2 Each independently is phenyl, naphthyl, pyridyl or quinolinyl.
Preferably, said L 1 Is phenyl or biphenyl.
Preferably, said R is 3 、R 4 Each independently selected from ethyl or o-dimethylphenyl.
Preferably, the organic electroluminescent compound is any one of the following compounds:
in the present invention, the organic electroluminescent compounds are exemplarily prepared using the following preparation methods:
step 1: reacting a compound shown as a formula 1 with a compound shown as a formula 2 to generate a compound shown as a formula 3; the specific reaction operation can be as follows: a compound of formula 1 (30.0mmol), a compound of formula 2 (45.0mmol), a reaction catalyst sodium t-butoxide (80.0mmol), chlorine (2-dicyclohexylphosphino-2, 6-dimethoxy-1, 1-biphenyl) -2-amino-1, 1-biphenyl (Sphos) (3.0mmol), palladium acetate (1.5mmol), and a solvent toluene (150mL) were added under nitrogen in a 500mL dry two-necked flask, and the resulting mixture was heated to 90-120 ℃ for 18-36 hours. After cooling to room temperature, water was added and the mixture was extracted with DCM/water. The combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated. The residue was purified by silica gel column chromatography to give the compound of formula 3.
Step 2: the compound shown in the formula 4 and the compound shown in the formula 5 are reacted to generate the compound shown in the formula 6, and the specific reaction operation can be as follows: a compound of formula 4, an iodo aromatic ring or an iodo heteroaromatic ring (i.e., a compound of formula 5) are added to a 500mL dry two-necked flask under nitrogen in a molar ratio of 1:1.5, the reaction catalyst is sodium t-butoxide, Sphos, palladium acetate, and the solvent is toluene (150mL), and the resulting mixture is heated to 110 ℃ and 120 ℃ for reaction for 24-48 hours. After cooling to room temperature, water was added and the mixture was extracted with DCM/water. The combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated. The residue was purified by silica gel column chromatography to give the compound of formula 6.
And step 3: the compound of formula 3 is reacted with bis pinacol diborate to generate the compound of formula 7, and the specific reaction operation can be as follows: a100 mL dry two-neck flask was charged with compound of formula 3, diprenyl diboronate in a 1:1.8 molar ratio under nitrogen and 1, 4-dioxane. After evaporation of the mixture at 105 ℃ to remove the solvent, the residue was extracted with DCM/water. The combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated. The crude product is purified by column chromatography on silica gel (eluent PE: EA,2:1) followed by recrystallization from toluene to give the compound of formula 7.
Wherein Ar is Ar as defined above 1 。
And 4, step 4: the compound shown in the formula 4 is reacted with the compound shown in the formula 7 to obtain the compound shown in the formula 8, and the specific reaction operation can be as follows: a100 mL two-necked flask containing a mixture of the compound of formula 4, the compound of formula 7 (molar ratio 1:1), potassium phosphate, Sphos and palladium acetate was charged with dry toluene, 1, 4-dioxane and water (volume ratio 3:1:1) under nitrogen. The mixture is refluxed at 100-120 ℃ for 12-24 hours. After cooling to room temperature, the mixture was extracted with DCM/water. The combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated. The residue was purified by silica gel column chromatography and then recrystallized from toluene to give the compound of formula I.
In another aspect, the present invention provides a hole transport material comprising any one of or a combination of at least two of the organic electroluminescent compounds as described above.
In another aspect, the present invention provides a hole transport layer comprising any one or a combination of at least two of the organic electroluminescent compounds as described above.
In another aspect, the present invention provides an organic electroluminescent device comprising a substrate, an anode layer, a cathode layer, and organic functional layers interposed between the anode layer and the cathode layer, at least one of the organic functional layers comprising an organic electroluminescent compound as described above.
Preferably, the organic functional layer comprises a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer, and the hole transport layer comprises any one of the organic electroluminescent compounds described above or a combination of at least two of the organic electroluminescent compounds.
Compared with the prior art, the invention has the following beneficial effects:
the organic electroluminescent compound provided by the invention can provide excellent OLED device performance, so that the OLED device has lower driving voltage and higher efficiency.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Preparation example 1
Synthesis of Compound 1:
in a 500mL dry two-necked flask, raw material A (30.0mmol), 1-bromo-3-iodobenzene (45.0mmol) and sodium tert-butoxide (80.0mmol), Sphos (3.0mmol), palladium acetate (1.5mmol) and toluene (150mL) were added under nitrogen, and the resulting mixture was heated to 90 ℃ for 18 hours. After cooling to room temperature, 50mL of water were added and the mixture was extracted with DCM/water. The combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated. The residue was purified by column chromatography on silica gel (eluent PE: DCM,5:1) to yield intermediate B as a white solid (yield 64%).
In a 500mL dry two-necked flask, raw material C (30.0mmol), 5-iododibenzothiophene (45.0mmol) and sodium tert-butoxide (80.0mmol), Sphos (3.0mmol), palladium acetate (1.5mmol) and toluene (150mL) were added under nitrogen, and the resulting mixture was heated to 110 ℃ for 24 hours. After cooling to room temperature, 50mL of water were added and the mixture was extracted with DCM/water. The combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated.
The residue was purified by silica gel column chromatography (eluent PE: DCM,5:1) to give intermediate D.
To a 100mL dry two-neck flask was added intermediate B (8.82mmol), dianilinoborate (13.23mmol) under nitrogen and 1, 4-dioxane (40 mL). After evaporation of the mixture at 105 ℃ to remove the solvent, the residue was extracted with DCM/water. The combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated. The crude product was purified by silica gel column chromatography (eluent PE: EA,2:1) and then recrystallized from toluene to give intermediate E.
To a 100mL two-necked flask containing a mixture of intermediate D (5.0mmol), intermediate E (5.0mmol), potassium phosphate (10.0mmol), Sphos (0.5mmol) and palladium acetate (0.25mmol) was added dry toluene (20mL), 1, 4-dioxane (5mL) and water (5mL) under a nitrogen atmosphere. The mixture was refluxed at 100 ℃ for 12 hours. After cooling to room temperature, the mixture was extracted with DCM/water. The combined organic layers were dried over magnesium sulfate, filtered and rotary evaporated. The residue was purified by silica gel column chromatography (eluent PE: DCM, 2:1) followed by recrystallization from toluene to give compound 1 (yield 70%).
Mass spectrometry and elemental analysis were performed on compound 1 and the other compounds prepared according to this example, respectively, with the following results:
compound 1: MS (EI) m/z 936.37; [ M ] A] + calcd for 937.21；C 84.58,O 3.41,N 2.99，S 3.42，H 5.99；
Compound 2: MS (EI) m/z 896.34; [ M ] A] + calcd for 896.15；C 84.34,O 3.57,N 3.12，S 3.57H 5.39；
Compound 5: MS (EI) m/z 916.17; [ M ] A] + calcd for 916.23；C 78.57,O 3.49,N 3.05，S 10.49，H 4.40；
Compound 6: MS (EI) m/z 886.27; [ M ] A] + calcd for 886.13；C 81.24,O 3.61,N 3.16，S 7.23H 4.77；
Compound 9: MS (EI) m/z 884.27; [ M ] A] + calcd for 884.05；C 81.43,O 7.23,N 3.17，S,3.62H 4.56；
Compound 12: MS (EI) m/z 933.09; [ M ] A] + calcd for 932.27；C 82.38,O 6.86, N 3.00，S 3.44，H 4.32；
Compound 26: MS (EI) m/z 809.01; [ M ] A] + calcd for 809.22；C 80.17,O 3.96,N 3.46，S 7.93，H 4.46。
Device examples D1-D6 and comparative example 1
An electroluminescent device, comprising the steps of:
step S1, forming an anode on the substrate by adopting an ITO material, and respectively ultrasonically cleaning the anode for 15 minutes by using deionized water, acetone and ethanol;
step S2, forming a hole injection layer with the thickness of 20nm on the anode in a vacuum evaporation mode, wherein the hole injection layer is formed by evaporation of a compound PD with the material of 2% doped with hexanitrile Hexaazatriphenylene (HI);
step S3, forming a hole transport layer with the thickness of 40nm on the hole injection layer by a vacuum evaporation mode, wherein the material adopted by the evaporation of the hole transport layer is the compound of the invention or the compound HT of the comparative example (see Table 1);
step S4, forming an electron blocking layer 14 with the thickness of 5nm on the hole transport layer in a vacuum evaporation mode, wherein EB is used as a main material of the electron blocking layer;
step S5, forming a light-emitting functional layer with the thickness of 40nm on the hole transport layer in a vacuum evaporation mode, wherein the light-emitting functional layer adopts RH as a main body material and RD as a doping material, and the mass ratio of the main body material to the doping material is 97: 3;
step S6, forming an electron transport layer with a thickness of 30nm on the light emitting functional layer by vacuum evaporation, where the electron transport layer 16 is evaporated from a material ET: ETM2(Liq) (50%: 50%);
the material structure used in the device is as follows:
TABLE 1
OLEDs are characterized in a standard manner. For this purpose, the electroluminescence spectrum, the power efficiency (measured in cd/a) and the voltage (measured at 1000cd/in2 in V) were determined from the current-voltage-luminance characteristics (JUL characteristics). For selected tests, the lifetime was determined. The lifetime is defined as the time after which the brightness has decreased from a certain starting brightness to a certain proportion. The numeral T95 indicates that the specified lifetime is that the luminance has dropped to 95% of the starting luminance, i.e. for example from 1000cd/m 2 Down to 950cd/m 2 The time of day. Different initial brightness is selected according to the light emission color. The lifetime value can be converted into other values of the starting brightness by means of conversion formulas known to the person skilled in the art. In this context, the starting luminance is 1000cd/m 2 The life of (A) is a standard value, and the performance characterization data is shown in the table2, respectively.
TABLE 2
As can be seen from Table 2, examples D1-D6, which used the compounds of the present invention as HTL materials, performed substantially equally well as the comparative examples, which used HTL materials representative in the art, indicating that the thiophene-containing triarylamine compounds of the present invention also provided superior OLED device performance, such as lower drive voltage and higher efficiency. Even at substantially comparable voltages, current efficiency (LE) and Power Efficiency (PE) are improved. The above results show that the structural compound disclosed by the invention has good prospects in the aspect of being used as a hole transport material.
The applicant states that the present invention is illustrated by the above examples of the organic electroluminescent compounds and their applications, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention must be implemented by means of the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (8)
1. An organic electroluminescent compound, wherein the organic electroluminescent compound has a structure represented by formula I:
wherein X may be O, S, or
Ar 1 And Ar 2 Each independently is an aromatic hydrocarbon group or an aromatic heterocyclic group, L 1 Represents a single bond, a 2-valent aromatic hydrocarbon group or a 2-valent aromatic heterocyclic group, R 1 And R 2 Independently selected from hydrogen atom, heavy hydrogen atom, fluorine atom, chlorine atom, cyano-group, nitro-group, alkyl group with 1-6 carbon atoms, cycloalkyl group with 5-10 carbon atoms, alkenyl group with 2-6 carbon atoms, alkoxy group with 1-6 carbon atoms, cycloalkoxy group with 5-10 carbon atoms, aromatic hydrocarbon group or aromatic heterocyclic group; r 3 、R 4 Each independently selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms or substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms; r 3 And R 4 Optionally linked to form a ring; m and n are each independently 0, 1 or 2.
2. The organic electroluminescent compound according to claim 1, wherein Ar is Ar 1 And Ar 2 Each independently is phenyl, naphthyl, pyridyl or quinolinyl.
3. The organic electroluminescent compound according to claim 1 or 2, wherein L is 1 Is phenyl or biphenyl.
4. The organic electroluminescent compound according to any one of claims 1 to 3, wherein R is 3 、R 4 Each independently selected from ethyl or o-dimethylphenyl.
5. The organic electroluminescent compound according to any one of claims 1 to 4, wherein the organic electroluminescent compound is any one of the following compounds:
6. a hole transport layer comprising any one of the organic electroluminescent compounds according to any one of claims 1 to 5 or a combination of at least two thereof.
7. An organic electroluminescent device comprising a substrate, an anode layer, a cathode layer, and organic functional layers interposed between the anode layer and the cathode layer, at least one of the organic functional layers comprising the organic electroluminescent compound according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 7, wherein the organic functional layer comprises a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer, and the hole transport layer comprises any one of the organic electroluminescent compounds according to any one of claims 1 to 5 or a combination of at least two thereof.
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