CN108503628A - A kind of organic electroluminescent compounds - Google Patents
A kind of organic electroluminescent compounds Download PDFInfo
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- CN108503628A CN108503628A CN201710108850.7A CN201710108850A CN108503628A CN 108503628 A CN108503628 A CN 108503628A CN 201710108850 A CN201710108850 A CN 201710108850A CN 108503628 A CN108503628 A CN 108503628A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 35
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 34
- 239000000463 material Substances 0.000 claims abstract description 32
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- -1 heterocyclic arene Chemical class 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 238000006884 silylation reaction Methods 0.000 claims abstract description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 3
- 238000005401 electroluminescence Methods 0.000 claims description 4
- 230000005611 electricity Effects 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 8
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 8
- 229940126543 compound 14 Drugs 0.000 description 8
- 230000005284 excitation Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 0 *1c(cccc2)c2-c2ccccc12 Chemical compound *1c(cccc2)c2-c2ccccc12 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000004506 ultrasonic cleaning Methods 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000002061 vacuum sublimation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 1
- OYZWEOORLJBPMA-UHFFFAOYSA-N 3,5-difluorobenzoyl chloride Chemical class FC1=CC(F)=CC(C(Cl)=O)=C1 OYZWEOORLJBPMA-UHFFFAOYSA-N 0.000 description 1
- WJNDBVIYUQZIAS-UHFFFAOYSA-N C(C1=CC=CC=C1)#N.C1=CC=CC=2C3=CC=CC=C3NC12 Chemical class C(C1=CC=CC=C1)#N.C1=CC=CC=2C3=CC=CC=C3NC12 WJNDBVIYUQZIAS-UHFFFAOYSA-N 0.000 description 1
- ZISGLVMVAWKGRE-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3NC12.N1=NN=CC=C1 Chemical class C1=CC=CC=2C3=CC=CC=C3NC12.N1=NN=CC=C1 ZISGLVMVAWKGRE-UHFFFAOYSA-N 0.000 description 1
- ZJHLOOMOXBPVCK-UHFFFAOYSA-N Fc1cc(-c2nc3ccccc3[n]2-c2ccccc2)cc(F)c1 Chemical compound Fc1cc(-c2nc3ccccc3[n]2-c2ccccc2)cc(F)c1 ZJHLOOMOXBPVCK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- Chemical & Material Sciences (AREA)
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- Physics & Mathematics (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a kind of organic electroluminescent compounds, with structure shown in lower formula (I)~(IV)： Wherein, R1And R2It is each independently selected from：H, the heterocyclic arene base that the aryl and cyclic carbon number that halogen, cyano, the alkyl group of C1~C20, the halogenated alkane base of C1~C20, the naphthenic base of C3~C20, the halogenated cycloalkyl of C3~C20, the alkoxy of C1~C20, the silylation of C1~C20, cyclic carbon number are 6~30 aryloxy group, cyclic carbon number are 6~30 are 6~30；Z1~Z4It is each independently selected from：The heterocyclic arene base that the aryl and cyclic carbon number that cyclic carbon number is 6~30 are 6~30.It is used as the material of main part of OLED luminescent layers using the compound, the OLED device service life of gained is long, has excellent luminous efficiency.
Description
Technical field
The present invention relates to electroluminescent organic material more particularly to a kind of organic electroluminescent compounds.
Background technology
Organic light emitting diode (Organic Light-Emitting Diodes, hereinafter referred " OLED ") is due to having
Self luminous characteristic has high contrast, wide viewing angle, responds fast, low in energy consumption, color reprodubility compared to LCD technology
Huge advantage that is good and can realizing flexible device is obtained for extensive commercial applications in display and lighting area.
For OLED device, two electrodes are applied a voltage to, hole and electronics are injected into luminescent layer from anode and cathode respectively,
And exciton is compounded to form in luminescent layer.According to electron spin statistical rules, the generation ratio of singlet state and triplet is 1:
3, for traditional fluorescence radiation molecule, due to being that can radiate the light that de excitation hair band comes using singlet excitons,
The limit of the internal quantum efficiency of OLED device is generally 25%.On the other hand, for phosphor material, since it has weight former
Intersystem crossing can efficiently occur for sub- effect, singlet excitons, and internal quantum efficiency maximum value can be close to 100%.
With the development of electroluminescent organic material, red light material and green light material have substantially met the needs of display.
However, feature of the blue light material due to its broad-band gap, charge injection is difficult, luminous efficiency and in terms of the service life relative to feux rouges and
Green light is backward.In addition, the operating voltage of some blue light material in the market is higher, the attainable color value of institute is also undesirable.
However, blue-light-emitting, the performance of especially dark blue light have important influence for carrying high display quality and reducing power consumption.
Blue light one kind important as OLED three primary colours in efficiency and is always to restrict what OLED was moved in terms of the service life
Bottleneck.Although the problem of blue phosphor materials can obtain higher device efficiency, the service life is undecided always；Traditional indigo plant
Although color fluorescent material has a longer life expectancy, relatively inefficient.From such background, if can be all or part of
Using the triplet exciton of fluorescent material, then the efficiency of Nan dian Yao can be increased substantially.
As a kind of important method using triplet exciton, " thermotropic delayed fluorescence " (Thermally Activated
Delayed Fluorescence, TADF) using the small material of singlet state and triplet energy level difference, under the action of ambient heat,
Triplet exciton can occur to the reversed intersystem crossing of singlet excitons, to improve internal quantum efficiency (Nature, 2012,492
(7428):234-238.)。
In terms of blue TADF materials, have based on using sulfone as the compound of core, such as open source literature J.Am.Chem.Soc.2012,
134,14706-14709, however the material is as guest emitting material that efficiency is roll-offed with the increase of current density in the devices
(Roll-off) very fast；Also there is the compound based on triazine-carbazole series, such as open source literature Adv.Mater.2015,27,
2515-2520, but excitation purity in the devices is bad, close to day blue light；Chemical combination for another example based on benzonitrile-carbazole series
Object, such as open source literature DOI：10.1039/c5mh00258c though the report in terms of having the service life, excitation purity and efficiency still need into
One step improves.As it can be seen that above technical solution, need to further improve service life in the devices and the excitation purity of blue light TADF materials.
Therefore, high efficiency, long-life and the high blue emitting material of excitation purity are developed, especially develop high efficiency,
Long-life and the high navy blue luminescent material of excitation purity, for promoting the development of ORGANIC ELECTROLUMINESCENCE DISPLAYS and lighting engineering to have
Great meaning.
Invention content
In view of many disadvantages existing in the prior art and deficiency, the present invention is intended to provide a kind of suitable organic compound
Object, as organic electroluminescence blue emitting material.Therefore, the first aspect of the present invention provides a kind of organic electroluminescent chemical combination
Object, the organic electroluminescent compounds have structure shown in lower formula (I)~(IV)：
Wherein, R1And R2It is each independently selected from：H, the halogenated chain of halogen, cyano, the alkyl group of C1~C20, C1~C20
Alkyl, the naphthenic base of C3~C20, the halogenated cycloalkyl of C3~C20, the alkoxy of C1~C20, C1~C20 silylation, take
Generation or unsubstituted cyclic carbon number be 6~30 aryloxy group, substituted or unsubstituted cyclic carbon number be 6~30 aryl and
The heterocyclic arene base that substituted or unsubstituted cyclic carbon number is 6~30；
Z1~Z4It is each independently selected from：Substituted or unsubstituted cyclic carbon number be 6~30 aryl and it is substituted or
The heterocyclic arene base that unsubstituted cyclic carbon number is 6~30.
Preferably, in above-mentioned organic electroluminescent compounds, R1And R2It is each independently selected from：H, the alkane of C1~C20
Base, the alkoxy of C1~C20, the aryloxy group that substituted or unsubstituted cyclic carbon number is 6~30, has the naphthenic base of C3~C20
The heterocycle that the aryl and substituted or unsubstituted cyclic carbon number that substituted or unsubstituted cyclic carbon number is 6~30 are 6~30
Aryl.
It is further preferred that in above-mentioned organic electroluminescent compounds, R1And R2It is each independently selected from：H, substituted
Or unsubstituted cyclic carbon number be 6~30 aryl and substituted or unsubstituted cyclic carbon number be 6~30 heterocyclic arene
Base.
It is further preferred that in above-mentioned organic electroluminescent compounds, R2For H.
It is further preferred that in above-mentioned organic electroluminescent compounds, R1Selected from following any group：
Most preferably, in above-mentioned organic electroluminescent compounds, R1Selected from following any group：
Preferably, in above-mentioned organic electroluminescent compounds, Z1~Z4It is each independently selected from following any group：
Specifically, the organic electroluminescent compounds preferably are selected from following any：
The second aspect of the present invention provides a kind of material of main part for OLED luminescent layers, contains the present invention first
Organic electroluminescent compounds described in aspect.
The third aspect of the present invention provides a kind of OLED luminescent layers, containing organic described in first aspect present invention
Electroluminescent compounds.
The fourth aspect of the present invention provides a kind of OLED device, contains the Organic Electricity described in first aspect present invention
Electro luminescent compounds.
In short, using main body material of the organic electroluminescent compounds as OLED luminescent layers shown in formula (I)~(IV) is led to
The OLED device service life of material, gained is long and has higher luminous efficiency and excitation purity.Therefore, provided by the present invention to have
Organic electro luminescent compounds are with a wide range of applications and outstanding market potential；The organic electroluminescent compounds are especially suitable
Together in as high efficiency, long-life and the high navy blue luminescent material of excitation purity, organic electroluminescence hair is promoted to a certain extent
Light is shown and the development of lighting engineering.
Specific implementation mode
The first aspect of the present invention provides a kind of organic electroluminescent compounds, the organic electroluminescent compounds
With structure shown in lower formula (I)~(IV)：
Wherein, R1And R2It is each independently selected from：H, the halogenated chain of halogen, cyano, the alkyl group of C1~C20, C1~C20
Alkyl, the naphthenic base of C3~C20, the halogenated cycloalkyl of C3~C20, the alkoxy of C1~C20, C1~C20 silylation, take
Generation or unsubstituted cyclic carbon number be 6~30 aryloxy group, substituted or unsubstituted cyclic carbon number be 6~30 aryl and
The heterocyclic arene base that substituted or unsubstituted cyclic carbon number is 6~30；
Z1~Z4It is each independently selected from：Substituted or unsubstituted cyclic carbon number be 6~30 aryl and it is substituted or
The heterocyclic arene base that unsubstituted cyclic carbon number is 6~30.
In a preferred embodiment, R1And R2It is each independently selected from：H, the ring of the alkyl group of C1~C20, C3~C20
Alkyl, the alkoxy of C1~C20, the aryloxy group, substituted or unsubstituted that substituted or unsubstituted cyclic carbon number is 6~30
The heterocyclic arene base that the aryl and substituted or unsubstituted cyclic carbon number that cyclic carbon number is 6~30 are 6~30.
In a further preferred embodiment, R1And R2It is each independently selected from：H, substituted or unsubstituted cyclization
The heterocyclic arene base that the aryl and substituted or unsubstituted cyclic carbon number that carbon number is 6~30 are 6~30.
In an embodiment still more preferably, R2For H.
In an embodiment still more preferably, R1Selected from following any group：
In a most preferred embodiment, R1Selected from following any group：
In a preferred embodiment, Z1~Z4It is each independently selected from following any group：
In a further preferred embodiment, the organic electroluminescent compounds are selected from following any：
The second aspect of the present invention provides a kind of material of main part for OLED luminescent layers, contains the present invention first
Organic electroluminescent compounds described in aspect.
The third aspect of the present invention provides a kind of OLED luminescent layers, containing organic described in first aspect present invention
Electroluminescent compounds.
The fourth aspect of the present invention provides a kind of OLED device, contains the Organic Electricity described in first aspect present invention
Electro luminescent compounds.
The present invention is further elaborated With reference to embodiment, but the present invention is not limited to following embodiments.
The method is conventional method unless otherwise specified；The raw material can obtain unless otherwise specified from open commercial sources.
The preparation of 1 compound 1 of embodiment
Step 1：Synthetic intermediate 1
3,5- difluoro benzoyl chlorides (15.3g, 90.0mmol) are dissolved in anhydrous methylene chloride (100mL), are then delayed
It is slow to be added to the triethylamine (25.4mL) and N- phenyl o-phenylenediamine (18.2g, 99.0mmol) for being dissolved in dichloromethane (200mL)
In solution.Under anaerobic, after reaction solution carries out reaction 24 hours, water (100mL) and sodium bicarbonate aqueous solution are used respectively
(100mL) is washed, and is finally neutralized with dilute hydrochloric acid, is extracted organic phase, is then dried with anhydrous magnesium sulfate.At reduced pressure conditions, it removes
Solvent is removed, obtained crude product purified by silica gel column chromatography purification, eluant, eluent is dichloromethane, finally obtains pure white powder
(21.5g, 76%), as intermediate 1.
The high resolution mass spec m/z [M+H] of intermediate 1+Theoretical value 307.1047, test value 307.1011.Step 2：It closes
At compound 1
By cesium carbonate (22.5g, 69.0mmol), carbazole (8.0g, 48.0mmol) and intermediate 1 (7.0g, 23.0mmol)
It is dissolved in DMSO (100mL), after removing air with argon gas, is heated to 160 DEG C, react 48 hours, be cooled to this condition
Room temperature, mixture are diluted with chloroform, and filtrate is obtained by filtration.After removing solvent at reduced pressure conditions, filtrate is dissolved in again
In chloroform, and washed twice respectively with saturated aqueous ammonium chloride and sodium hydrate aqueous solution；Organic phase is obtained by extraction in merging,
It is dried with anhydrous magnesium sulfate, is concentrated to give crude product, again with methanol/ether washing, then, from dichloromethane/ethanol solution
Recrystallization twice, obtain purer compound 1, the vacuum sublimation of compound 1 is purified twice, obtain pure compound 1 (8.7g,
63%).
The high resolution mass spec m/z [M+H] of compound 1+：Theoretical value 600.2314, test value 600.2287.
The preparation of 2 compound 14 of embodiment
Step 1：Synthetic intermediate 1, specific steps are identical as the step one in embodiment 1；
Step 2：Synthesize compound 14
By cesium carbonate (22.5g, 69.0mmol), raw material 1 (13.6g, 48.0mmol) and intermediate 1 (7.0g,
It 23.0mmol) is dissolved in DMSO (100mL), after removing air with argon gas, is heated to 160 DEG C, it is small to react 52 with this condition
When, it is cooled to room temperature, reaction solution is diluted with chloroform, and filtrate is obtained by filtration.After removing solvent at reduced pressure conditions, again by filtrate
It is secondary to be dissolved in chloroform, and washed twice respectively with saturated aqueous ammonium chloride and sodium hydrate aqueous solution；Merging extracts
It to organic phase, is dried with anhydrous magnesium sulfate, is concentrated to give crude product, again with methanol/ether washing, then from dichloromethane/ethyl alcohol
It is recrystallized in solution and obtains purer compound 14 twice, the vacuum sublimation of compound 14 is purified twice, pure chemical combination is obtained
Object 14 (11.1g, 58%).
The high resolution mass spec m/z [M+H] of compound 14+：Theoretical value 832.3566, test value 832.3587.
The preparation of 3 compound 54 of embodiment
Step 1：Synthetic intermediate 1, specific steps are identical as the step one in embodiment 1；
Step 2：Synthesize compound 54
By cesium carbonate (22.5g, 69.0mmol), raw material 2 (12.3g, 48.0mmol) and intermediate 1 (7.0g,
It 23.0mmol) is dissolved in DMSO (100mL), after removing air with argon gas, is heated to 160 DEG C, it is small to react 52 with this condition
When, it is cooled to room temperature, reaction solution is diluted with chloroform, and filtrate is obtained by filtration.Solvent is removed at reduced pressure conditions, again by filtrate
It is secondary to be dissolved in chloroform, and washed twice respectively with saturated aqueous ammonium chloride and sodium hydrate aqueous solution；Merging extracts
It to organic phase, is dried with anhydrous magnesium sulfate, is concentrated to give crude product, again with methanol/ether washing, then from dichloromethane/second
It is recrystallized in alcoholic solution and obtains purer compound 54 twice, the vacuum sublimation of compound 54 is purified twice, and pure chemical combination is obtained
Object 54 (10.0g, 56%).
The high resolution mass spec m/z [M+H] of compound 54+：Theoretical value 780.2525, test value 780.2538.
The preparation of OLED device of the embodiment 4 containing compound 1
Be arranged on the glass substrate of 25mm x75mm x1.1mm sizes film thickness be 120nm, be made of tin indium oxide
Transparent electrode, and ultrasonic cleaning in 10 minutes is carried out in isopropanol, and then carry out 30 minutes UV ozone cleans.
After cleaning, this glass substrate with transparent electrode is installed on the substrate holder of vacuum deposition apparatus：
First, compound HI-1 is deposited on the glass substrate to cover above-mentioned transparent electrode, to form 80nm thickness
HI-1 layers；Then, HI-2 is deposited on HI-1 layers, obtains the HI-2 layers that thickness is 5nm；
Then, aromatic compound HT-1 is deposited, the hole transmission layer of 10nm thickness is made；
It is deposited altogether using the thickness of 40nm on above-mentioned hole transmission layer as the compound 1 of material of main part and as object material
The compound R D of material forms luminescent layer with film forming；Wherein, the mass concentration of compound R D is 3%.
Then, the ET-1 of 30nm is deposited altogether on above-mentioned luminescent layer:EI-1 (mass ratioes 1:1) it is used as electron transfer layer,
The ET-1 of 2nm thickness is deposited again as electron injecting layer；
Finally, the aluminium of vapor deposition 120nm thickness is as cathode.
Skeleton symbol according to OLED device made from above step is：
ITO/HI-1 (80nm)/HI-2 (5nm)/HT-1 (10)/compound 1:RD (40nm, 3%wt)/ET-1:EI-1
(30nm,1:1)/ET-1(2nm)/Al(120nm)。
Compound HI-1, HI-2, HT-1, RD, ET-1 and EI-1 involved in above-mentioned OLED device preparation process are respectively
The compound of structure as follows：
The preparation of OLED device of the embodiment 5 containing compound 14
Be arranged on the glass substrate of 25mm x75mm x1.1mm sizes film thickness be 120nm, be made of tin indium oxide
Transparent electrode, and ultrasonic cleaning in 10 minutes is carried out in isopropanol, and then carry out 30 minutes UV ozone cleans.
After cleaning, this glass substrate with transparent electrode is installed on the substrate holder of vacuum deposition apparatus：
First, compound HI-1 is deposited on the glass substrate to cover above-mentioned transparent electrode, to form 80nm thickness
HI-1 layers；Then, HI-2 is deposited on HI-1 layers, obtains the HI-2 layers that thickness is 5nm；
Then, aromatic compound HT-1 is deposited, the hole transmission layer of 10nm thickness is made；
It is deposited altogether using the thickness of 40nm on above-mentioned hole transmission layer as the compound 14 of material of main part and as object
The compound R D of material forms luminescent layer with film forming；Wherein, the mass concentration of compound R D is 3%.
Then, the ET-1 of 30nm is deposited altogether on above-mentioned luminescent layer:EI-1 (mass ratioes 1:1) it is used as electron transfer layer,
The ET-1 of 2nm thickness is deposited again as electron injecting layer；
Finally, the aluminium of vapor deposition 120nm thickness is as cathode.
Skeleton symbol according to OLED device made from above step is：
ITO/HI-1 (80nm)/HI-2 (5nm)/HT-1 (10)/compound 14:RD (40nm, 3%wt)/ET-1:EI-1
(30nm,1:1)/ET-1(2nm)/Al(120nm)。
The preparation of OLED device of the embodiment 6 containing compound 54
Be arranged on the glass substrate of 25mm x75mm x1.1mm sizes film thickness be 120nm, be made of tin indium oxide
Transparent electrode, and ultrasonic cleaning in 10 minutes is carried out in isopropanol, and then carry out 30 minutes UV ozone cleans.
After cleaning, this glass substrate with transparent electrode is installed on the substrate holder of vacuum deposition apparatus：
First, compound HI-1 is deposited on the glass substrate to cover above-mentioned transparent electrode, to form 80nm thickness
HI-1 layers；Then, HI-2 is deposited on HI-1 layers, obtains the HI-2 layers that thickness is 5nm；
Then, aromatic compound HT-1 is deposited, the hole transmission layer of 10nm thickness is made；
It is deposited altogether using the thickness of 40nm on above-mentioned hole transmission layer as the compound 54 of material of main part and as object
The compound R D of material forms luminescent layer with film forming；Wherein, the mass concentration of compound R D is 3%.
Then, the ET-1 of 30nm is deposited altogether on above-mentioned luminescent layer:EI-1 (mass ratioes 1:1) it is used as electron transfer layer,
The ET-1 of 2nm thickness is deposited again as electron injecting layer；
Finally, the aluminium of vapor deposition 120nm thickness is as cathode.
Skeleton symbol according to OLED device made from above step is：
ITO/HI-1 (80nm)/HI-2 (5nm)/HT-1 (10)/compound 54:RD (40nm, 3%wt)/ET-1:EI-1
(30nm,1:1)/ET-1(2nm)/Al(120nm)。
OLED device prepares comparative example
In this comparative example, the making step of OLED device is identical as the making step in embodiment 4-6, and unique difference exists
Select compound CBP, structural formula as follows in material of main part therein：
In order to characterize the performance of above each OLED device, inventor has carried out correlated performance test：In various electric currents and
Electroluminescent spectrum is recorded under voltage, from current/voltage/luminous density characteristic curve (IUL spies that Lambert transmitting features are presented
Sign line) it is calculated as the current efficiency (cd/A calculating) of luminous density function, and determine the service life of OLED device；In addition,
15mA/cm2Current density under record electroluminescent spectrum, and voluntarily calculate the color coordinates of CIE1931x and y.
15mA/cm2Under service life LT95 indicate current density be 15mA/cm2Corresponding starting brightness (cd/m2) declined 5% and passed through
The time crossed.Specifically, it is shown in Table 1 under above-mentioned the performance test results：
| Maximum current efficiency (cd/A) | CIE(x,y) | LT95 (hour) | |
| Embodiment 4 | 32.4 | (0.66,0.32) | 152 |
| Embodiment 5 | 35.6 | (0.66,0.33) | 147 |
| Embodiment 6 | 31.7 | (0.65,0.33) | 167 |
| Comparative example | 23.9 | (0.67,0.32) | 106 |
Table 1
By upper table 1 it is found that the OLED device prepared as material of main part using compound of the present invention, with comparative example
It compares, shows higher luminous efficiency and longer service life.
Specific embodiments of the present invention are described in detail above, but it is intended only as example, the present invention is simultaneously unlimited
In particular embodiments described above.To those skilled in the art, any to the equivalent modifications that carry out of the present invention and to replace
In generation, is also all among scope of the invention.Therefore, without departing from the spirit and scope of the invention made by impartial conversion and repair
Change, all should be contained within the scope of the invention.
Claims (11)
1. a kind of organic electroluminescent compounds, which is characterized in that the organic electroluminescent compounds have lower formula (I)~
(IV) structure shown in：
Wherein, R1And R2It is each independently selected from：H, halogen, cyano, the alkyl group of C1~C20, C1~C20 halogenated alkane base,
The naphthenic base of C3~C20, the halogenated cycloalkyl of C3~C20, the alkoxy of C1~C20, C1~C20 silylation, it is substituted or
The aryl and take that aryloxy group that unsubstituted cyclic carbon number is 6~30, substituted or unsubstituted cyclic carbon number are 6~30
The heterocyclic arene base that generation or unsubstituted cyclic carbon number are 6~30；
Z1~Z4It is each independently selected from：The aryl and substituted or nothing that substituted or unsubstituted cyclic carbon number is 6~30 take
The heterocyclic arene base that the cyclic carbon number in generation is 6~30.
2. organic electroluminescent compounds according to claim 1, which is characterized in that R1And R2It is each independently selected from：H、
The alkyl group of C1~C20, the naphthenic base of C3~C20, the alkoxy of C1~C20, substituted or unsubstituted cyclic carbon number be 6~
30 aryloxy group, the aryl that substituted or unsubstituted cyclic carbon number is 6~30 and substituted or unsubstituted cyclic carbon number
For 6~30 heterocyclic arene base.
3. organic electroluminescent compounds according to claim 2, which is characterized in that R1And R2It is each independently selected from：H、
The aryl and substituted or unsubstituted cyclic carbon number that substituted or unsubstituted cyclic carbon number is 6~30 be 6~30 it is miscellaneous
Cyclophane alkyl.
4. organic electroluminescent compounds according to claim 3, which is characterized in that R2For H.
5. organic electroluminescent compounds according to claim 3, which is characterized in that R1Selected from following any group：
6. organic electroluminescent compounds according to claim 5, which is characterized in that R1Selected from following any group：
7. organic electroluminescent compounds according to claim 1, which is characterized in that Z1~Z4Be each independently selected from
Under any group：
8. organic electroluminescent compounds according to any one of claims 1 to 7, which is characterized in that the Organic Electricity
Electro luminescent compounds are selected from following any：
9. a kind of material of main part for OLED luminescent layers, which is characterized in that it contains as described in any one of claim 1-8
Organic electroluminescent compounds.
10. a kind of OLED luminescent layers, which is characterized in that it contains the hair of the organic electroluminescence as described in any one of claim 1-8
Optical compounds.
11. a kind of OLED device, which is characterized in that it contains the organic electroluminescent as described in any one of claim 1-8
Compound.
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