CN109535011A - Electroluminescent organic material and organic electroluminescence device comprising it - Google Patents
Electroluminescent organic material and organic electroluminescence device comprising it Download PDFInfo
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- CN109535011A CN109535011A CN201811581714.0A CN201811581714A CN109535011A CN 109535011 A CN109535011 A CN 109535011A CN 201811581714 A CN201811581714 A CN 201811581714A CN 109535011 A CN109535011 A CN 109535011A
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 31
- 239000011368 organic material Substances 0.000 title claims abstract description 23
- 239000000463 material Substances 0.000 claims abstract description 19
- 230000005540 biological transmission Effects 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 159
- 150000001721 carbon Chemical group 0.000 claims description 157
- 239000010410 layer Substances 0.000 claims description 67
- -1 dimethyl fluorenyl Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000004450 alkenylene group Chemical group 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 230000004888 barrier function Effects 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 3
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 3
- 150000002790 naphthalenes Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- 150000001875 compounds Chemical class 0.000 abstract description 28
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 abstract description 25
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- 125000005259 triarylamine group Chemical group 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 196
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 38
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- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 14
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
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- 238000001819 mass spectrum Methods 0.000 description 8
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
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- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 6
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- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 6
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- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 4
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 4
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- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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Abstract
The present invention provides electroluminescent organic material and the organic electroluminescence device comprising it, belongs to electroluminescent technology field.Based on the structure of triarylamine, the second core group centered on adamantane is introduced；Wherein triarylamine has excellent hole transporting properties, is the basis that such material can be used as hole transmission layer；And adamantane has biggish steric hindrance, the structure of rigid solid can reduce molecular crystalline, reduce energy loss caused by molecule itself vibration relaxation while improving material filming；The compound of the group of the present invention containing adamantane has excellent hole transport performance, it can be used for making organic electroluminescence device, especially as the hole transport layer material in organic electroluminescence device, the luminous efficiency and service life of organic luminescent device can be effectively improved.
Description
Technical field
The present invention relates to a kind of electroluminescent organic material and its as organic electroluminescence device hole-transporting layer material
The application of material, and in particular to a kind of electroluminescent organic material and the organic electroluminescence device comprising it belong to electroluminescent
Field.
Background technique
Electroluminescent (Electroluminescence), and electroluminescence can be claimed, abbreviation EL is by being added in two electrodes
Voltage generate electric field, by electric field excite electronics hit the centre of luminescence, and be led to electronics transition between energy level, variation, answer
Conjunction leads to a kind of luminous physical phenomenon.In recent years, organic electroluminescence device (OLED:Organic
Electroluminescent device) visual field of people is progressed into as display technology of new generation.OLED is one kind by more
The electroluminescent device that layer organic thin film structure is formed, organic film therein are using vapor deposition, vapor deposition or spin coating proceeding in base
The film of the luminous organic material formed on plate.Compared with traditional display technology, in voltage characteristic, light emission luminance, shine effect
Rate, chromaticness, response speed and appreciative perspective etc. very advantageous, and it is at low cost, therefore possess vast market prospect.
In order to improve brightness, efficiency and the service life of organic electroluminescence device, multilayered structure is usually used in the devices.This
A little multilayered structures include: hole injection layer (hole injection layer), hole transmission layer (hole transport
Layer), electronic barrier layer ((electron-blocking layer), luminescent layer (emitting layer) and electron-transport
Layer (electron transport layer) etc..These organic layers, which have, improves carrier (hole and electronics) in each stratum boundary
Injection efficiency between face, the ability that equilbrium carrier transmits between the layers, to improve the brightness and efficiency of device.
Although the technology is still currently, the electroluminescent organic material of a large amount of function admirables developed successively
There are many problems, how to design the better material of new performance and are adjusted, so that all devices can reach reduction electricity
It presses, improve efficiency effect with the service life, be always those skilled in the art's urgent problem to be solved.
Summary of the invention
The purpose of the present invention is to provide a kind of with high-fire resistance and excellent chemical stability and can be used as sky
The electroluminescent organic material of cave implanted layer, hole transporting layer or electronic blocking layer material etc..
Another object of the present invention is to provide a kind of organic luminescent device comprising the electroluminescent organic material, tools
There are lower driving voltage, higher luminous efficiency and service life.
To achieve the above object, the technical solution of the present invention is as follows:
A kind of electroluminescent organic material, the structure of the material as described in chemical formula 1:
R1、Ar1With Ar2Alkane that is identical or different, being separately 1-40 selected from substituted or unsubstituted carbon atom number
Alkynyl that alkenyl that base, substituted or unsubstituted carbon atom number are 2-40, substituted or unsubstituted carbon atom number are 2-32 replaces
Or unsubstituted carbon atom number be 3-40 naphthenic base, substituted or unsubstituted carbon atom number be 2-40 Heterocyclylalkyl, replace
Or unsubstituted carbon atom number be 7-40 aralkyl, substituted or unsubstituted carbon atom number be 2-40 heteroarylalkyl, replace
Or unsubstituted carbon atom number be 6-40 aryl, substituted or unsubstituted carbon atom number be one of heteroaryl of 1-40；
Ar3Selected from singly-bound, alkylidene, the substituted or unsubstituted carbon atom that substituted or unsubstituted carbon atom number is 1-40
Alkynylene that alkenylene that number is 2-40, substituted or unsubstituted carbon atom number are 2-32, substituted or unsubstituted carbon atom number
For the ring alkylidene of 3-40, substituted or unsubstituted carbon atom number be 2-40 heterocycloalkylene group, substituted or unsubstituted carbon it is former
Heteroarylidene that sub- aralkyl that subnumber is 7-40, substituted or unsubstituted carbon atom number are 1-40, substituted or unsubstituted carbon
It is miscellaneous sub- aralkyl that arlydene that atomicity is 6-40, substituted or unsubstituted carbon atom number are 2-40, substituted or unsubstituted
The ring alkenylene of carbon atom number 3-15, the miscellaneous alkynylene of substituted or unsubstituted carbon atom number 2-32, substituted or unsubstituted carbon
One of miscellaneous alkenylene of atomicity 2-15.
A further improvement of the present invention lies in that the R1、Ar1、Ar2And Ar3Substituent group it is identical or different, and respectively
It does not take independently selected from deuterium, cyano, nitro, halogen, hydroxyl, the alkyl of substituted or unsubstituted carbon atom number 1-40, substitution or
The naphthenic base of the carbon atom number 3-40 in generation, the alkenyl of substituted or unsubstituted carbon atom number 2-40, substituted or unsubstituted carbon are former
The alkynyl of subnumber 2-32, the Heterocyclylalkyl of substituted or unsubstituted carbon atom number 2-40, substituted or unsubstituted carbon atom number 7-
40 aralkyl, the heteroarylalkyl of substituted or unsubstituted carbon atom number 2-40, substituted or unsubstituted carbon atom number 6-40
Aryl, the heteroaryl of substituted or unsubstituted carbon atom number 1-40, substituted or unsubstituted carbon atom number 1-40 alkoxy, take
Generation or the alkylamino of unsubstituted carbon atom number 1-40, substituted or unsubstituted carbon atom number 6-30 fragrant amino, replace or not
Substituted carbon atom number is the alkylthio group of 1-40, the arylalkylamino of substituted or unsubstituted carbon atom number 7-30, substitution or does not take
The heteroaryl amino of the carbon atom number 1-24 in generation, the aIkylsilyl groups that substituted or unsubstituted carbon atom number is 1-45, replace or
Aryloxy group that arylsilyl groups that unsubstituted carbon atom number is 6-50, substituted or unsubstituted carbon atom number are 6-30 takes
Generation or unsubstituted carbon atom number are one of 6-30 arylthio.
A further improvement of the present invention lies in that the R1、Ar1With Ar2It is identical or different, separately selected from replace or
Heteroarylalkyl that aralkyl that unsubstituted carbon atom number is 7-40, substituted or unsubstituted carbon atom number are 2-40, replace or
Aryl that unsubstituted carbon atom number is 6-30, substituted or unsubstituted carbon atom number are one of heteroaryl of 1-40.
A further improvement of the present invention lies in that the Ar3Selected from substituted or unsubstituted phenyl, xenyl, naphthalene, diformazan
One of base fluorenyl, dibenzofuran group, dibenzothiophene.
A further improvement of the present invention lies in that the chemical formula 1 is one of following structural compounds:
A further improvement of the present invention lies in that the Ar3Selected from substituted or unsubstituted phenyl, substituted or unsubstituted
Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted dimethyl fluorenyl, replaces substituted or unsubstituted terphenyl
Or one of unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene.
A kind of organic electroluminescence device, including cathode, anode and one layer or more between the cathode and anode
Organic layer has at least one layer comprising described in claim 1 in one layer or more the organic layer between the cathode and anode
Electroluminescent material.
A further improvement of the present invention lies in that the organic layer is selected from hole injection layer, hole transmission layer, electronic blocking
Layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer.
A further improvement of the present invention lies in that the organic layer comprising electroluminescent organic material described in claim 1 is
Hole transmission layer.
Compared with prior art, the invention has the benefit that the feature and meaning of the compounds of this invention are, with three
Based on the structure of arylamine, the second core group centered on adamantane is introduced；Wherein triarylamine has excellent
Hole transporting properties are the bases that such material can be used as hole transmission layer；And adamantane has biggish steric hindrance, just
Property firm structure, molecular crystalline can reduced, molecule itself vibration relaxation is reduced while improving material filming and is led
The energy loss of cause；
On the basis of above two big core function group, this class formation in introducing another aryl group on adamantane, this
Aryl group effect is main are as follows:
1. being increased between intermolecular triarylamine core group under the premise of not influencing adamantane physical characteristic
Energy transmission path further improves the hole-conductive rate of material；
2. a pair adamantane core group plays a degree of protective effect, inhibit it that isomerization/de- occurs at high temperature
Hydrogen reaction, to improve the purity and device performance of material.
The compound of the group containing adamantane of the invention has excellent hole transport performance, can be used for making organic electroluminescence
Luminescent device can effectively improve organic illuminator especially as the hole transport layer material in organic electroluminescence device
The luminous efficiency and service life of part.
Detailed description of the invention
Fig. 1 is the structural schematic diagram of electroluminescent organic material of the invention.
Specific embodiment
Hereinafter, by embodiment, the present invention is described in more detail.But following embodiments are only examples of the invention
Show, and and the non-limiting present invention.
Referring to Fig. 1, a kind of electroluminescent organic material of the invention, the structure of the material as described in chemical formula 1:
R1、Ar1With Ar2Alkane that is identical or different, being separately 1-40 selected from substituted or unsubstituted carbon atom number
Alkynyl that alkenyl that base, substituted or unsubstituted carbon atom number are 2-40, substituted or unsubstituted carbon atom number are 2-32 replaces
Or unsubstituted carbon atom number be 3-40 naphthenic base, substituted or unsubstituted carbon atom number be 2-40 Heterocyclylalkyl, replace
Or unsubstituted carbon atom number be 7-40 aralkyl, substituted or unsubstituted carbon atom number be 2-40 heteroarylalkyl, replace
Or unsubstituted carbon atom number be 6-40 aryl, substituted or unsubstituted carbon atom number be one of heteroaryl of 1-40；
Ar3Selected from singly-bound, alkylidene, the substituted or unsubstituted carbon atom that substituted or unsubstituted carbon atom number is 1-40
Alkynylene that alkenylene that number is 2-40, substituted or unsubstituted carbon atom number are 2-32, substituted or unsubstituted carbon atom number
For the ring alkylidene of 3-40, substituted or unsubstituted carbon atom number be 2-40 heterocycloalkylene group, substituted or unsubstituted carbon it is former
Heteroarylidene that sub- aralkyl that subnumber is 7-40, substituted or unsubstituted carbon atom number are 1-40, substituted or unsubstituted carbon
It is miscellaneous sub- aralkyl that arlydene that atomicity is 6-40, substituted or unsubstituted carbon atom number are 2-40, substituted or unsubstituted
The ring alkenylene of carbon atom number 3-15, the miscellaneous alkynylene of substituted or unsubstituted carbon atom number 2-32, substituted or unsubstituted carbon
One of miscellaneous alkenylene of atomicity 2-15；
The R1、Ar1、Ar2And Ar3Substituent group it is identical or different, and separately selected from deuterium, cyano, nitro,
Halogen, hydroxyl, the alkyl of substituted or unsubstituted carbon atom number 1-40, substituted or unsubstituted carbon atom number 3-40 cycloalkanes
Base, the alkenyl of substituted or unsubstituted carbon atom number 2-40, substituted or unsubstituted carbon atom number 2-32 alkynyl, replace or not
The aralkyl, substituted or unsubstituted of the Heterocyclylalkyl of substituted carbon atom number 2-40, substituted or unsubstituted carbon atom number 7-40
The heteroarylalkyl of carbon atom number 2-40, the aryl of substituted or unsubstituted carbon atom number 6-40, substituted or unsubstituted carbon it is former
The heteroaryl of subnumber 1-40, the alkoxy of substituted or unsubstituted carbon atom number 1-40, substituted or unsubstituted carbon atom number 1-
40 alkylamino, the fragrant amino of substituted or unsubstituted carbon atom number 6-30, substituted or unsubstituted carbon atom number are 1-40's
The heteroaryl of alkylthio group, the arylalkylamino of substituted or unsubstituted carbon atom number 7-30, substituted or unsubstituted carbon atom number 1-24
AIkylsilyl groups that amino, substituted or unsubstituted carbon atom number are 1-45, substituted or unsubstituted carbon atom number are 6-50
Arylsilyl groups, substituted or unsubstituted carbon atom number be 6-30 aryloxy group, substituted or unsubstituted carbon atom number be
One of 6-30 arylthio.
Specifically, the R1、Ar1With Ar2It is identical or different, separately it is selected from substituted or unsubstituted carbon atom number
For the aralkyl of 7-40, substituted or unsubstituted carbon atom number be 2-40 heteroarylalkyl, substituted or unsubstituted carbon atom number
The heteroaryl for being 1-40 for the aryl of 6-30, substituted or unsubstituted carbon atom number.
Specifically, the Ar3The arlydene, substituted or unsubstituted for being 6-40 selected from substituted or unsubstituted carbon atom number
It is sub- aralkyl that heteroarylidene that carbon atom number is 1-40, substituted or unsubstituted carbon atom number are 7-40, substituted or unsubstituted
Carbon atom number be one of miscellaneous sub- aralkyl of 2-40.
Specifically, the chemical formula 1 is one of following structural compounds:
Heretofore described Ar3It does not take selected from substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substitution or
The terphenyl in generation, substituted or unsubstituted naphthalene, substituted or unsubstituted dimethyl fluorenyl, substituted or unsubstituted dibenzo
One of furyl, substituted or unsubstituted dibenzothiophene.
A kind of organic electroluminescence device based on above-mentioned electroluminescent organic material, including cathode, anode and in institute
Possessed one layer or more organic layer between cathode and anode is stated, includes at least one layer in described one layer or more of organic layer
Above-mentioned electroluminescent organic material.
The organic layer is selected from hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electronics
Transport layer and electron injecting layer.
Organic layer comprising the electroluminescent organic material is hole transmission layer.
Unsubstituted alkyl in the present invention refers to that carbon atom number is the alkyl of the straight chain of 1-40, or includes carbon atom number
For the alkyl of the branch of 1-13.For example, methyl, ethyl, propyl, isobutyl group, sec-butyl, amyl, isopentyl, base etc..Replace
Carbon atom number be 1-40 alkyl refer to that at least one hydrogen atom is taken by D-atom, F, Cl, I, CN, hydroxyl, nitro, amino etc.
Generation.
Unsubstituted alkenyl in the present invention, the carbon atom number referred to are the alkenyl of 2-40, the carbon comprising carbon-carbon double bond
Atomicity is the alkenyl of the straight chain of 2-40, or the alkenyl comprising the branch that carbon atom number is 1-13.Such as: vinyl, acrylic,
Allyl, isopropenyl, 2- cyclobutenyl etc..The alkenyl that substituted carbon atom number is 2-40 refers at least one hydrogen atom by deuterium original
Son, F, Cl, I, CN, hydroxyl, nitro, amino etc. replace.
Unsubstituted alkynyl in the present invention, the carbon atom number referred to are the alkynyl of 2-32, the carbon comprising triple carbon-carbon bonds
Atomicity is the alkynyl of the straight chain of 2-32, or the alkynyl comprising the branch that carbon atom number is 1-10.Such as: acetenyl, 2- propine
Base etc..Substituted carbon atom number is that the alkynyl of 2-32 refers at least one hydrogen atom by D-atom, F, Cl, I, CN, hydroxyl, nitre
Base, amino etc. replace.
Unsubstituted aryl in the present invention, the carbon atom number referred to are the aryl of 6-40.Such as: phenyl, naphthalene, pyrene
Base, dimethyl fluorenyl, anthryl, phenanthryl,Base, camomile ring group, acenaphthenyl, xenyl, benzo anthryl, two fluorenyl of spiral shell, base, indenyl
Deng.Substituted carbon atom number be 6-40 aryl refer at least one hydrogen atom by D-atom, F, Cl, I, CN, hydroxyl, nitro,
Amino etc. replaces.
Unsubstituted aralkyl in the present invention refers to that carbon atom number is the aralkyl of 7-30.Such as: tolyl, diformazan
Base fluorenyl etc..Substituted carbon atom number be 7-30 aralkyl refer at least one hydrogen atom by D-atom, F, Cl, I, CN,
Hydroxyl, nitro, amino etc. replace.
The unsubstituted heteroaryl of the present invention refers to that carbon atom number is the heteroaryl of 2-40.Such as: pyridyl group, pyrazinyl,
Pyrimidine radicals, pyridazinyl, triazine radical, quinolyl, indyl, carbazyl, dibenzofuran group, dibenzothiophene, dibenzo selenium
Pheno base etc..Substituted carbon atom number be 2-40 heteroaryl refer at least one hydrogen atom by D-atom, F, Cl, I, CN, hydroxyl,
Nitro, amino etc. replace.
The unsubstituted naphthenic base of the present invention refers to that carbon atom number is the naphthenic base of 3-40.Such as: cyclopropyl, cyclobutyl,
Cyclopenta, cyclohexyl, norborny, adamantyl etc..Substituted carbon atom number is that the naphthenic base of 3-40 refers at least one
Hydrogen atom is replaced by D-atom, F, Cl, I, CN, hydroxyl, nitro, amino etc..
It is illustrated below by specific embodiment.
The synthesis of compound 1
Bromobenzene (10.0g, 63.7mmol) is dissolved in tetrahydrofuran (20mL), under the conditions of 0 DEG C of nitrogen protection, is slowly dripped
Enter to be placed with magnesium rod (1.9g, 76.2mmol) and 1, in tetrahydrofuran (20mL) solution of 2- Bromofume (0.1g), drips
Reaction nature is warmed to room temperature after finishing, and is kept stirring 3h；Reaction solution is transferred in another container to remove remaining magnesium rod, decompression
Under the conditions of remove tetrahydrofuran, solid is added methylene chloride (30mL) and is diluted；Then under room temperature and nitrogen protection, slowly
Methylene chloride (50mL) solution dissolved with 1- bromine adamantane (13.7g, 76.4mmol) is added dropwise, is heated to flowing back, is kept stirring 2h；
After cooling, reaction solution is poured into 0 DEG C of 2mol/L hydrochloric acid, separate organic phase, water phase is extracted using normal heptane；By having for merging
, filtering dry using magnesium sulfate after machine is mutually washed, is removed under reduced pressure solvent；Using normal heptane as mobile phase, silica gel column chromatography is used
Crude product is purified, colorless oil 8.5g intermediate 1-A-I, yield 58% are obtained.
At 0 DEG C, by intermediate 1-A-I (8.5g, 40.0mmol) be added portionwise dissolved with chromium trioxide (12.0g,
It in acetic acid (60mL) and acetic anhydride (60mL) mixed solution 120.1mmol), is then warmed to room temperature naturally, stirs 12h.To anti-
It answers and water and methylene chloride is added in liquid, stir liquid separation after 0.5h, water phase makes to be extracted with dichloromethane, and merges organic phase, and sulphur is added
Solvent is removed under reduced pressure after drying, filtering in sour magnesium；Obtain yellow oil crude product；It is water-soluble that 2mol/L sodium hydroxide is added into crude product
Liquid (60mL), is stirred at room temperature 8h, the solid being obtained by filtration；Using methylene chloride/normal heptane as mobile phase, silica gel column chromatography is used
Crude product is purified, 4.1g white solid intermediate 1-A-II, yield 45% are obtained.
Intermediate 1-A-II (4.1g, 18.0mmol) and bromobenzene (2.8g, 18.0mmol) are dissolved in methylene chloride (30mL)
In, it under the conditions of subzero 40 DEG C of nitrogen protections, is slowly added dropwise trifluoromethanesulfonic acid (3.2g, 21.5mmol), is risen after insulated and stirred 4h
Temperature 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that reacting liquid pH value=7 to 0 DEG C.Then liquid separation, organic phase
It is dry using magnesium sulfate is added after washing, solvent is removed under reduced pressure；Using normal heptane as mobile phase, using silica gel column chromatography to crude product
It is purified, obtains 4.5g white solid intermediate 1-A, yield 68%.
By bromo- 9, the 9- dimethyl fluorene (10.0g, 36.6mmol) of 2-, 2- amino -9,9- dimethyl fluorene (8.4g,
0.3mmol), tris(dibenzylideneacetone) dipalladium (0.7g, 0.7mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl
(0.7g, 1.5mmol) and sodium tert-butoxide (5.3g, 54.9mmol) are added in toluene (100mL), under nitrogen protection, heating
It to reflux temperature, stirs 2h and is then cooled to room temperature, reaction solution is led to filtrate after being dried, filtered using addition magnesium sulfate after washing
Too short silicagel column, is removed under reduced pressure solvent；Recrystallization purification is carried out to crude product using methylene chloride/n-heptane system, obtains 12.3g
Light yellow solid intermediate 1-B, yield 84%.
By intermediate 1-A (4.5g, 12.3mmol), 1-B (4.9g, 12.3mmol), tris(dibenzylideneacetone) dipalladium
(0.2g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.2g, 0.5mmol) and sodium tert-butoxide (1.8g,
It 18.4mmol) is added in toluene (50mL), is heated to reflux temperature under nitrogen protection, stir 8h；It is then cooled to room temperature, instead
It answers liquid using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column, solvent is removed under reduced pressure；Use dichloromethane
Alkane/n-heptane system carries out recrystallization purification to crude product, obtains 5.8g compound as white solid 1, yield 69%).Mass spectrum: m/
Z=688.4 (M+H+)。
The synthesis of compound 2
Intermediate 1-A-II (5.0g, 21.9mmol) and 4- bromo biphenyl (5.1g, 21.9mmol) are dissolved in methylene chloride
In (35mL), under the conditions of subzero 20 DEG C of nitrogen protections, trifluoromethanesulfonic acid (3.9g, 26.3mmol), insulated and stirred is slowly added dropwise
It is warming up to 0 DEG C after 2h, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that reacting liquid pH value=7.Then liquid separation,
Organic phase is dry using magnesium sulfate is added after washing, and solvent is removed under reduced pressure；Using normal heptane as mobile phase, silica gel column chromatography is used
Crude product is purified, 5.5g white solid intermediate 2-A, yield 57% are obtained.
By 4- bromo biphenyl (10.0g, 42.9mmol), 4- aminobphenyl (8.0g, 47.2mmol), three (dibenzalacetones)
Two palladiums (0.8g, 0.9mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (0.8g, 1.7mmol) and sodium tert-butoxide
(6.2g, 64.3mmol) is added in toluene (100mL), is heated to reflux temperature under nitrogen protection, stirs 1h；Then it is cooled to
Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in room temperature, reaction solution；Make
Recrystallization purification is carried out to crude product with methylene chloride/ethanol system, obtains 10.4g light yellow solid intermediate 2-B, yield is
75%.
By intermediate 2-A (5.5g, 12.4mmol), intermediate 2-B (4.0g, 12.4mmol), three (dibenzalacetones)
Two palladiums (0.2g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.2g, 0.5mmol) and sodium tert-butoxide
(1.8g, 18.6mmol) is added in toluene (60mL), is heated to reflux temperature under nitrogen protection, stirs 6h；Then it is cooled to
Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in room temperature, reaction solution；Make
Recrystallization purification is carried out to crude product with methylene chloride/n-heptane system, obtains 5.1g compound as white solid 2, yield 60%.
Mass spectrum: m/z=684.4 (M+H+)。
The synthesis of compound 3
2- bromonaphthalene (15.0g, 72.4mmol) is dissolved in tetrahydrofuran (30mL), under the conditions of 0 DEG C of nitrogen protection, slowly
Instillation is placed with magnesium rod (2.1g, 87.5mmol) and 1, in tetrahydrofuran (30mL) solution of 2- Bromofume (0.1g), is added dropwise
After react nature be warmed to room temperature, be kept stirring 2h；Reaction solution is transferred in another container to remove remaining magnesium rod, is subtracted
Tetrahydrofuran is removed under the conditions of pressure, methylene chloride (30mL) dilution is added in solid；Then under room temperature and nitrogen protection, slowly drip
Solubilization has methylene chloride (60mL) solution of 1- bromine adamantane (15.6g, 72.4mmol), is heated to flowing back, is kept stirring 3h；Drop
Wen Hou pours into reaction solution in 0 DEG C of 2mol/L hydrochloric acid, separates organic phase, and water phase makes to be extracted with dichloromethane；By having for merging
Machine is dried, filtered after mutually washing using magnesium sulfate, and solvent is removed under reduced pressure；Using methylene chloride/normal heptane as mobile phase, silica gel is used
Column chromatography purifies crude product, obtains 9.7g white solid intermediate 3-A-I, yield 59%.
At 0 DEG C, by intermediate 3-A-I (9.7g, 37.0mmol) be added portionwise dissolved with chromium trioxide (11.1g,
It in acetic acid (60mL) and acetic anhydride (60mL) mixed solution 110.9mmol), is then warmed to room temperature naturally, stirs 10h.To anti-
It answers and water and methylene chloride is added in liquid, stir liquid separation after 0.5h, water phase makes to be extracted with dichloromethane, and merges organic phase, and sulphur is added
Solvent is removed under reduced pressure after drying, filtering in sour magnesium；Obtain yellow solid crude product；2mol/L sodium hydrate aqueous solution is added into crude product
(60mL), stirs 6h at room temperature, and solid is obtained by filtration；Using methylene chloride/normal heptane as mobile phase, silica gel column chromatography pair is used
Crude product is purified, and 5.2g white solid intermediate 3-A-II, yield 51% are obtained.
Intermediate 3-A-II (5.2g, 18.7mmol) and bromobenzene (2.9g, 18.7mmol) are dissolved in methylene chloride (40mL)
In, it under the conditions of subzero 40 DEG C of nitrogen protections, is slowly added dropwise trifluoromethanesulfonic acid (3.4g, 22.4mmol), is risen after insulated and stirred 3h
Temperature 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that reacting liquid pH value=7 to 0 DEG C.Then liquid separation, organic phase
It is dry using magnesium sulfate is added after washing, solvent is removed under reduced pressure；Using methylene chloride/normal heptane as mobile phase, silicagel column color is used
Spectrometry purifies crude product, obtains 4.6g white solid intermediate 3-A, yield 59%.
By bromo- 9, the 9- dimethyl fluorene (10.0g, 36.6mmol) of 2-, 4- aminobphenyl (6.8g, 40.3mmol), three (two Asias
Benzylacetone) two palladiums (0.7g, 0.7mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (0.7g, 1.5mmol) and
Sodium tert-butoxide (5.3g, 54.9mmol) is added in toluene (100mL), is heated to reflux temperature under nitrogen protection, stirs 2h；And
After be cooled to room temperature, reaction solution is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column
Solvent；Recrystallization purification is carried out to crude product using methylene chloride/ethanol system, obtains 9.8g white solid intermediate 3-B, yield
For 83%).
By intermediate 3-A (4.6g, 11.0mmol), 3-B (4.0g, 11.0mmol), tris(dibenzylideneacetone) dipalladium
(0.2g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.2g, 0.4mmol) and sodium tert-butoxide (1.6g,
It 16.5mmol) is added in toluene (50mL), is heated to reflux temperature under nitrogen protection, stir 12h；Then it is cooled to room temperature,
Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro
Methane/ethyl acetate system carries out recrystallization purification to crude product, obtains 4.3g compound as white solid 3, yield 56%.Matter
Spectrum: m/z=698.4 (M+H+)。
The synthesis of compound 4
The bromo- 9,9- dimethyl fluorene (4.8g, 17.5mmol) of intermediate 1-A-II (4.0g, 17.5mmol) and 2- is dissolved in two
It in chloromethanes (30mL), under the conditions of subzero 30 DEG C of nitrogen protections, is slowly added dropwise trifluoromethanesulfonic acid (3.2g, 21.0mmol), protects
It is warming up to 0 DEG C after temperature stirring 4h, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that reacting liquid pH value=7.Then
Liquid separation, organic phase is dry using magnesium sulfate is added after washing, and solvent is removed under reduced pressure；Using methylene chloride/normal heptane as mobile phase, make
Crude product is purified with silica gel column chromatography, obtains 4.8g white solid intermediate 4-A, yield 57%.
By 2- bromonaphthalene (10.0g, 48.3mmol), 4- aminobphenyl (9.0g, 53.1mmol), three (dibenzalacetones) two
Palladium (0.9g, 1.0mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (0.9g, 1.9mmol) and sodium tert-butoxide
(7.0g, 72.4mmol) is added in toluene (100mL), is heated to reflux temperature under nitrogen protection, stirs 1h；Then it is cooled to
Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in room temperature, reaction solution；Make
Recrystallization purification is carried out to crude product with methylene chloride/n-heptane system, obtains 11.9g white solid intermediate 4-B, yield is
77%.
By intermediate 4-A (4.8g, 9.9mmol), 4-B (2.9g, 9.9mmol), tris(dibenzylideneacetone) dipalladium
(0.2g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.2g, 0.4mmol) and sodium tert-butoxide (1.4g,
It 14.9mmol) is added in toluene (50mL), is heated to reflux temperature under nitrogen protection, stir 12h；Then it is cooled to room temperature,
Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro
Methane/n-heptane system carries out recrystallization purification to crude product, obtains 4.7g compound as white solid 4, yield 68%.Mass spectrum:
M/z=698.4 (M+H+)。
The synthesis of compound 5
Intermediate 1-A-II (5.0g, 17.5mmol) and 2- bromonaphthalene (3.6g, 17.5mmol) are dissolved in methylene chloride
In (30mL), under the conditions of subzero 40 DEG C of nitrogen protections, trifluoromethanesulfonic acid (3.2g, 21.0mmol), insulated and stirred is slowly added dropwise
It is warming up to 0 DEG C after 2h, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that reacting liquid pH value=7.Then liquid separation,
Organic phase is dry using magnesium sulfate is added after washing, and solvent is removed under reduced pressure；Using methylene chloride/normal heptane as mobile phase, silicon is used
Rubber column gel column chromatography purifies crude product, obtains 4.5g white solid intermediate 5-A, yield 62%.
By bromo- 9, the 9- dimethyl fluorene (10.0g, 36.6mmol) of 2-, 2- aminobphenyl (6.8g, 40.3mmol), three (two Asias
Benzylacetone) two palladiums (0.7g, 0.7mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (0.7g, 1.5mmol) and
Sodium tert-butoxide (5.3g, 54.9mmol) is added in toluene (100mL), is heated to reflux temperature under nitrogen protection, stirs 3h；And
After be cooled to room temperature, reaction solution is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column
Solvent；Recrystallization purification is carried out to crude product using methylene chloride/ethanol system, obtains 11.0g light yellow solid intermediate 5-B,
Yield is 83%.
By intermediate 5-A (4.5g, 10.8mmol), 5-B (3.9g, 10.8mmol), tris(dibenzylideneacetone) dipalladium
(0.2g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.2g, 0.4mmol) and sodium tert-butoxide (1.6g,
It 16.2mmol) is added in toluene (50mL), is heated to reflux temperature under nitrogen protection, stir 12h；Then it is cooled to room temperature,
Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro
Methane/n-heptane system carries out recrystallization purification to crude product, obtains 5.0g compound as white solid 5, yield 66%.Mass spectrum:
M/z=698.4 (M+H+)。
The synthesis of compound 6
Intermediate 1-A-II (4.0g, 17.5mmol) and 2- bromine dibenzofurans (4.3g, 17.5mmol) are dissolved in dichloro
It in methane (30mL), under the conditions of subzero 40 DEG C of nitrogen protections, is slowly added dropwise trifluoromethanesulfonic acid (3.2g, 21.0mmol), keeps the temperature
0 DEG C is risen to after stirring 4h, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that reacting liquid pH value=7.Then divide
Liquid, organic phase is dry using magnesium sulfate is added after washing, and solvent is removed under reduced pressure；Using normal heptane as mobile phase, silicagel column color is used
Spectrometry purifies crude product, obtains 5.1g white solid intermediate 6-A, yield 64%.
By 4- bromo biphenyl (10.0g, 42.9mmol), aniline (4.4g, 47.2mmol), tris(dibenzylideneacetone) dipalladium
(0.8g, 0.9mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (0.8g, 1.7mmol) and sodium tert-butoxide
(6.2g, 64.3mmol) is added in toluene (100mL), and reflux temperature is heated under nitrogen protection, stirs 1h；Then it is cooled to room
Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in temperature, reaction solution；It uses
Methylene chloride/ethanol system carries out recrystallization purification to crude product, obtains 8.3g pale brownish solid Intermediate 6-B, yield 79%.
By intermediate 6-A (5.1g, 11.1mmol), 6-B (2.7g, 11.1mmol), tris(dibenzylideneacetone) dipalladium
(0.2g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.2g, 0.4mmol) and sodium tert-butoxide (1.6g,
It 16.7mmol) is added in toluene (50mL), is heated to reflux temperature under nitrogen protection, stir 6h；It is then cooled to room temperature, instead
It answers liquid using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column, solvent is removed under reduced pressure；Use dichloromethane
Alkane/n-heptane system carries out recrystallization purification to crude product, obtains 4.2g compound as white solid 6, yield 61%.Mass spectrum: m/z
=622.3 (M+H+)。
The synthesis of compound 7
4- bromo biphenyl (15.0g, 64.3mmol) is dissolved in tetrahydrofuran (35mL), under the conditions of 0 DEG C of nitrogen protection, is delayed
Slow instill is placed with magnesium rod (1.9g, 77.2mmol) and 1, in tetrahydrofuran (30mL) solution of 2- Bromofume (0.1g), drop
Nature is reacted after adding to be warmed to room temperature, and is kept stirring 3h；Reaction solution is transferred in another container to remove remaining magnesium rod,
Tetrahydrofuran is removed under reduced pressure, methylene chloride (30mL) dilution is added in solid；Then under room temperature and nitrogen protection, slowly
Methylene chloride (50mL) solution dissolved with 1- bromine adamantane (13.8g, 64.3mmol) is added dropwise, is heated to flowing back, is kept stirring 3h；
After cooling, reaction solution is poured into 0 DEG C of 2mol/L hydrochloric acid, separate organic phase, water phase makes to be extracted with dichloromethane；By merging
It is dried, filtered after organic phase washing using magnesium sulfate, solvent is removed under reduced pressure；Using normal heptane as mobile phase, silica gel column chromatography is used
Method purifies crude product, obtains 8.0g white solid intermediate 7-A-I, yield 41%.
At 0 DEG C, by intermediate 7-A-I (8.0g, 27.7mmol) be added portionwise dissolved with chromium trioxide (8.3g,
It in acetic acid (50mL) and acetic anhydride (50mL) mixed solution 83.2mmol), is then warmed to room temperature naturally, stirs 10h.To reaction
Water and methylene chloride are added in liquid, stirs liquid separation after 0.5h, water phase makes to be extracted with dichloromethane, and merges organic phase, and sulfuric acid is added
Solvent is removed under reduced pressure after drying, filtering in magnesium；Obtain yellow solid crude product；2mol/L sodium hydrate aqueous solution is added into crude product
(50mL), is stirred at room temperature 8h, and solid is obtained by filtration；Using methylene chloride/normal heptane as mobile phase, silica gel column chromatography is used
Crude product is purified, 4.4g white solid intermediate 7-A-II, yield 52% are obtained.
Intermediate 7-A-II (4.4g, 14.5mmol) and bromobenzene (2.3g, 14.5mmol) are dissolved in methylene chloride (30mL)
In, it under the conditions of subzero 30 DEG C of nitrogen protections, is slowly added dropwise trifluoromethanesulfonic acid (2.6g, 17.3mmol), is risen after insulated and stirred 6h
Temperature 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that reacting liquid pH value=7 to 0 DEG C.Then liquid separation, organic phase
It is dry using magnesium sulfate is added after washing, solvent is removed under reduced pressure；Using normal heptane as mobile phase, using silica gel column chromatography to crude product
It is purified, obtains 4.3g white solid intermediate 7-A, yield 65%.
By 2- bromine dibenzofurans (10.0g, 40.5mmol), 2- amino -9,9- dimethyl fluorene (9.3g, 44.5mmol),
Tris(dibenzylideneacetone) dipalladium (0.7g, 0.8mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (0.8g,
1.6mmol) and sodium tert-butoxide (5.8g, 60.7mmol) is added in toluene (100mL), is heated to reflux temperature under nitrogen protection
Degree stirs 4h；It is then cooled to room temperature, reaction solution after washing using being added filtrate after magnesium sulfate dries, filters through short silicon
Solvent is removed under reduced pressure in rubber column gel column；Recrystallization purification is carried out to crude product using methylene chloride/n-heptane system, it is solid to obtain 12.9g white
Body intermediate 7-B yield is 85%.
By intermediate 7-A (4.3g, 9.7mmol), 7-B (3.6g, 9.7mmol), tris(dibenzylideneacetone) dipalladium
(0.2g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.2g, 0.4mmol) and sodium tert-butoxide (1.4g,
It 14.5mmol) is added in toluene (40mL), is heated to reflux temperature under nitrogen protection, stir 10h；Then it is cooled to room temperature,
Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro
Methane/ethyl acetate system carries out recrystallization purification to crude product, obtains 4.6g compound as white solid 7, yield 64%.Matter
Spectrum: m/z=738.4 (M+H+)
The synthesis of compound 8
3- bromo biphenyl (10.0g, 42.9mmol) is dissolved in tetrahydrofuran (15mL), under the conditions of 0 DEG C of nitrogen protection, is delayed
Slow instill is placed with magnesium rod (1.3g, 54.2mmol) and 1, in tetrahydrofuran (25mL) solution of 2- Bromofume (0.1g), drop
Nature is reacted after adding to be warmed to room temperature, and is kept stirring 3h；Reaction solution is transferred in another container to remove remaining magnesium rod,
Tetrahydrofuran is removed under reduced pressure, methylene chloride (20mL) dilution is added in solid；Then under room temperature and nitrogen protection, slowly
Methylene chloride (40mL) solution dissolved with 1- bromine adamantane (9.2g, 42.9mmol) is added dropwise, is heated to flowing back, is kept stirring 4h；
After cooling, reaction solution is poured into 0 DEG C of 2mol/L hydrochloric acid, separate organic phase, water phase is extracted using normal heptane；By having for merging
Machine is dried, filtered after mutually washing using magnesium sulfate, and solvent is removed under reduced pressure；Using normal heptane as mobile phase, silica gel column chromatography is used
Crude product is purified, 6.5g colorless oil intermediate 8-A-I, yield 66% are obtained.
At 0 DEG C, by intermediate 8-A-I (6.5g, 22.5mmol) be added portionwise dissolved with chromium trioxide (6.8g,
It in acetic acid (40mL) and acetic anhydride (40mL) mixed solution 67.6mmol), is then warmed to room temperature naturally, stirs 16h.To reaction
Water and methylene chloride are added in liquid, stirs liquid separation after 0.5h, water phase makes to be extracted with dichloromethane, and merges organic phase, and sulfuric acid is added
Solvent is removed under reduced pressure after drying, filtering in magnesium；Obtain yellow oil crude product；2mol/L sodium hydrate aqueous solution is added into crude product
(40mL), stirs 10h at room temperature, the solid being obtained by filtration；Using methylene chloride/normal heptane as mobile phase, silica gel column chromatography is used
Method purifies crude product, obtains 4.1g white solid intermediate 8-A-II, yield 60%.
Intermediate 8-A-II (4.1g, 13.5mmol) and bromobenzene (2.1g, 13.5mmol) are dissolved in methylene chloride (30mL)
In, it under the conditions of subzero 30 DEG C of nitrogen protections, is slowly added dropwise trifluoromethanesulfonic acid (2.4g, 16.2mmol), is risen after insulated and stirred 5h
Temperature 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that pH value=7 of reaction solution to 0 DEG C.Then liquid separation, it is organic
It is mutually dry using magnesium sulfate is added after washing, solvent is removed under reduced pressure；Using normal heptane as mobile phase, using silica gel column chromatography to thick
Product are purified, and 3.9g white solid intermediate 8-A, yield 63% are obtained.
By 3- bromine-N-phenylcarbazole (10g, 31.0mmol), 2- amino -9,9- dimethyl fluorene (7.1g, 34.1mmol), three
(dibenzalacetone) two palladium (0.6g, 0.6mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (0.6g,
1.2mmol) and sodium tert-butoxide (4.5g, 46.6mmol) is added in toluene (100mL), is heated to reflux temperature under nitrogen protection
Degree stirs 3h；It is then cooled to room temperature, reaction solution after washing using being added filtrate after magnesium sulfate dries, filters through short silicon
Solvent is removed under reduced pressure in rubber column gel column；Recrystallization purification is carried out to crude product using methylene chloride/n-heptane system, it is solid to obtain 10.4g white
Body intermediate 8-B, yield 74%.
By intermediate 8-A (3.9g, 8.8mmol), 8-B (4.0g, 8.8mmol), tris(dibenzylideneacetone) dipalladium
(0.2g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.1g, 0.4mmol) and sodium tert-butoxide (1.3g,
It 13.2mmol) is added in toluene (40mL), is heated to reflux temperature under nitrogen protection, stir 8h；It is then cooled to room temperature, instead
It answers liquid using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column, solvent is removed under reduced pressure；Use dichloromethane
Alkane/ethyl acetate system carries out recrystallization purification to crude product, obtains 4.1g compound as white solid 8, yield 57%.Mass spectrum:
M/z=813.4 (M+H+)
The synthesis of compound 9
3- bromine-N-phenylcarbazole (20g, 62.1mmol) is dissolved in tetrahydrofuran (35mL), in 0 DEG C of nitrogen protection condition
Under, it is slowly dropped into and is placed with magnesium rod (1.8g, 74.5mmol) and 1, tetrahydrofuran (30mL) solution of 2- Bromofume (0.1g)
In, nature is reacted after being added dropwise and is warmed to room temperature, and 5h is kept stirring；Reaction solution is transferred in another container to remove remnants
Magnesium rod, tetrahydrofuran is removed under reduced pressure, and methylene chloride (40mL) dilution is added in solid；Then in room temperature and nitrogen protection
Under, methylene chloride (40mL) solution dissolved with 1- bromine adamantane (13.4g, 62.3mmol) is slowly added dropwise, is heated to flowing back, keeps
Stir 2h；After cooling, reaction solution is poured into 0 DEG C of 2mol/L hydrochloric acid, separate organic phase, water phase makes to be extracted with dichloromethane；
It is dried, filtered after combined organic phase is washed using magnesium sulfate, solvent is removed under reduced pressure；It is flowing with methylene chloride/normal heptane
Phase purifies crude product using silica gel column chromatography, obtains 7.0g white solid intermediate 9-A-I, yield 49%.
At 0 DEG C, by intermediate 9-A-I (7.0g, 18.5mmol) be added portionwise dissolved with chromium trioxide (5.6g,
It in acetic acid (50mL) and acetic anhydride (50mL) mixed solution 55.6mmol), is then warmed to room temperature naturally, stirs 12h.To reaction
Water and methylene chloride are added in liquid, stirs liquid separation after 0.5h, water phase makes to be extracted with dichloromethane, and merges organic phase, and sulfuric acid is added
Solvent is removed under reduced pressure after drying, filtering in magnesium；Obtain yellow solid crude product；2mol/L sodium hydrate aqueous solution is added into crude product
(50mL), is stirred at room temperature 8h, and solid is obtained by filtration；Using methylene chloride/normal heptane as mobile phase, using silica gel column chromatography to thick
Product are purified, and 4.7g white solid intermediate 9-A-II, yield 64% are obtained.
Intermediate 9-A-II (4.7g, 11.9mmol) and bromobenzene (1.9g, 11.9mmol) are dissolved in methylene chloride (30mL)
In, it under the conditions of subzero 30 DEG C of nitrogen protections, is slowly added dropwise trifluoromethanesulfonic acid (2.2g, 14.3mmol), is risen after insulated and stirred 5h
Temperature 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that reacting liquid pH value=7 to 0 DEG C.Then liquid separation, organic phase
It is dry using magnesium sulfate is added after washing, solvent is removed under reduced pressure；Using methylene chloride/normal heptane as mobile phase, silicagel column color is used
Spectrometry purifies crude product, obtains 4.0g white solid intermediate 9-A, yield 63%.
By intermediate 9-A (4.0g, 7.5mmol), diphenylamines (1.3g, 7.5mmol), tris(dibenzylideneacetone) dipalladium
(0.1g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.1g, 0.3mmol) and sodium tert-butoxide (1.1g,
It 11.3mmol) is added in toluene (40mL), is heated to reflux temperature under nitrogen protection, stir 8h；It is then cooled to room temperature, instead
It answers liquid using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column, solvent is removed under reduced pressure；Use dichloromethane
Alkane/n-heptane system carries out recrystallization purification to crude product, obtains 3.3g compound as white solid 9, yield 71%.Mass spectrum: m/z
=621.3 (M+H+)
The synthesis of compound 10
Bromo- 9, the 9- dimethyl fluorene (15.0g, 54.9mmol) of 2- is dissolved in tetrahydrofuran (25mL), in 0 DEG C of nitrogen protection
Under the conditions of, it is slowly dropped into and is placed with magnesium rod (1.6g, 65.9mmol) and 1, the tetrahydrofuran (25mL) of 2- Bromofume (0.1g)
Nature is reacted in solution, after being added dropwise to be warmed to room temperature, and is kept stirring 4h；Reaction solution is transferred in another container to remove
Remaining magnesium rod, tetrahydrofuran is removed under reduced pressure, and methylene chloride (30mL) dilution is added in solid；Then protected in room temperature and nitrogen
Under shield, methylene chloride (40mL) solution dissolved with 1- bromine adamantane (11.8g, 54.9mmol) is slowly added dropwise, is heated to flowing back, protects
Hold stirring 3h；After cooling, reaction solution is poured into 0 DEG C of 2mol/L hydrochloric acid, separate organic phase, water phase is extracted using normal heptane；
It is dried, filtered after combined organic phase is washed using magnesium sulfate, solvent is removed under reduced pressure；Using normal heptane as mobile phase, silicon is used
Rubber column gel column chromatography purifies crude product, obtains 5.9g White waxy object intermediate 10-A-I, yield 47%.
At 0 DEG C, by intermediate 10-A-I (5.9g, 18.0mmol) be added portionwise dissolved with chromium trioxide (5.4g,
It in acetic acid (40mL) and acetic anhydride (40mL) mixed solution 53.9mmol), is then warmed to room temperature naturally, stirs 10h.To reaction
Water and methylene chloride are added in liquid, stirs liquid separation after 0.5h, water phase makes to be extracted with dichloromethane, and merges organic phase, and sulfuric acid is added
Solvent is removed under reduced pressure after drying, filtering in magnesium；Obtain yellow solid crude product；2mol/L sodium hydrate aqueous solution is added into crude product
(40mL), is stirred at room temperature 6h, the solid being obtained by filtration；Using methylene chloride/normal heptane as mobile phase, silica gel column chromatography pair is used
Crude product is purified, and 3.9g white solid intermediate 10-A-II, yield 63% are obtained.
Intermediate 10-A-II (3.9g, 11.3mmol) and bromobenzene (1.8g, 11.3mmol) are dissolved in methylene chloride (30mL)
In, it under the conditions of subzero 30 DEG C of nitrogen protections, is slowly added dropwise trifluoromethanesulfonic acid (2.0g, 13.6mmol), is risen after insulated and stirred 6h
To 0 DEG C, 2mol/L sodium hydrate aqueous solution is added dropwise into reaction solution, so that pH value=7 of reaction solution.Then liquid separation, organic phase
It is dry using magnesium sulfate is added after washing, solvent is removed under reduced pressure；Using methylene chloride/normal heptane as mobile phase, silicagel column color is used
Spectrometry purifies crude product, obtains 4.1g white solid intermediate 10-A, yield 75%.
By 2- bromonaphthalene (10g, 48.3mmol), aniline (4.9g, 53.1mmol), tris(dibenzylideneacetone) dipalladium (0.9g,
1.0mmol), 2- dicyclohexyl phosphorus -2,4,6- tri isopropyl biphenyl (0.9g, 1.9mmol) and sodium tert-butoxide (7.0g,
It 72.4mmol) is added in toluene (100mL), is heated to reflux temperature under nitrogen protection, stir 1h；Then it is cooled to room temperature,
Solvent is removed under reduced pressure using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column in reaction solution；Use dichloro
Methane/ethanol system carries out recrystallization purification to crude product, obtains 8.2g pale brownish solid Intermediate 10-B, yield 77%.
By intermediate 10-A (4.1g, 8.5mmol), 10-B (1.9g, 8.5mmol), tris(dibenzylideneacetone) dipalladium
(0.2g, 0.2mmol), 2- dicyclohexyl phosphorus -2,6- dimethoxy-biphenyl (0.1g, 0.3mmol) and sodium tert-butoxide (1.2g,
It 12.7mmol) is added in toluene (40mL), is heated to reflux temperature under nitrogen protection, stir 6h；It is then cooled to room temperature, instead
It answers liquid using being added filtrate after magnesium sulfate dries, filters after washing through short silicagel column, solvent is removed under reduced pressure；Use dichloromethane
Alkane/n-heptane system carries out recrystallization purification to crude product, obtains 3.3g compound as white solid 10, yield 63%.Mass spectrum: m/
Z=622.4 (M+H+)。
Embodiment 1: production organic electroluminescence device
Anode is prepared by following procedure: will be with a thickness ofIto substrate (healthy and free from worry manufacture) be cut into 40mm ×
The size of 40mm × 0.7mm is prepared into the pattern with cathode and anode region and insulating layer using photo-mask process
Experimental substrate utilizes UV ozone and O2:N2Plasma is surface-treated, to increase the work function of anode (experimental substrate)
And descum.
On glass experimental substrate (anode) vacuum evaporation m-MTDATA with formed with a thickness of hole injection layer (HIL),
And on hole injection layer vacuum evaporation compound 1 with formed with a thickness ofHole transmission layer (HTL).
Be deposited TCTA on the hole transport layer, formed with a thickness ofElectronic barrier layer (EBL).
It regard α, β-AND as main body, while adulterating 4,4'- (3,8- bis- (N, the N- diphenyl benzenes of diphenyl pyrene -1,6- diyl
Amine), form with a thickness ofLuminescent layer (EML).
DBimiBphen and LiQ is mixed and is deposited with the weight ratio of 1:1 and is formdThick electron transport
Layer (ETL), by LiQ vapor deposition on the electron transport layer with formed with a thickness ofElectron injecting layer (EIL), then by magnesium (Mg)
Mixed with silver-colored (Ag) with the ratio of 9:1, vacuum evaporation formed on electron injecting layer with a thickness ofCathode.
In addition, as N- (4- (9H- carbazole -9- base) the phenyl) -4'- being deposited with a thickness of 65nm on above-mentioned cathode
(9H- carbazole -9- base)-N- phenyl-[1,1'- biphenyl] -4- amine is formed coating (CPL), to complete organic luminescent device
Manufacture.
Embodiment 2-10
Other than respectively using compound shown in table 1 when forming hole transmission layer, utilization is same as Example 1
Method make organic electroluminescence device.
I.e. embodiment 2 makes organic electroluminescence device using compound 2, and embodiment 3 makes Organic Electricity using compound 3
Corresponding compound 4-10 production organic electroluminescence device is respectively adopted in electroluminescence device, embodiment 4-10, and device performance is shown in
Table 1.
Comparative example 1- comparative example 3
In the embodiment 1, in addition to having used NPB, compound A and compound B as hole transporting layer substitutionization
It closes except object 1, manufactures organic electroluminescence device with method same as Example 1.
I.e. comparative example 1 manufactures organic electroluminescence device using NPB, and comparative example 2 is using compound A manufacture organic electroluminescence hair
Optical device, comparative example 3 manufacture organic electroluminescence device using compound B, and device performance is shown in Table 1.
To organic electroluminescence device prepared above, in 10mA/cm2Under conditions of analyze the performance of device, knot
Fruit is shown in the following table 1.
1 device performance of table
Reference table 1, in the case that the compound of the present invention is used as hole transporting layer by embodiment 1-10, with comparative example 1-3
Compound compare, voltage (V), current efficiency (Cd/A), brightness (Cd/m2) and external quantum efficiency (EQE) and half-life
(T50) better characteristics is showed.Therefore, the device made using the compounds of this invention, having reduces driving voltage, improves hair
Light efficiency and the characteristic to prolong the service life.
In conclusion the compounds of this invention to be used as to the hole transmission layer of organic electroluminescence device, so that including the change
The organic electroluminescence device for closing object has lower driving voltage, higher luminous efficiency and better service life.
According to the table 1 of the result of the organic electroluminescent device of the embodiment it is found that the compound of the present invention is in adamantane
After introducing aryl group, when being used as hole transporting material, the hole-conductive rate of material is further improved.It therefore, can be with
Manufacture the organic electroluminescence device with excellent characteristics such as driving voltage, luminous efficiency, external quantum efficiency and half-life.
Above embodiments are the further explanation to the compound of the present invention, and range is claimed simultaneously in invention of the invention
It is not limited to this.For those skilled in the art, remembered not departing to invent in claimed range
Under the range of the technical idea of the invention carried, the various supplements and deformation carry out to the present invention also belong to protection model of the invention
It encloses.
Claims (9)
1. a kind of electroluminescent organic material, which is characterized in that the structure of the material as described in chemical formula 1:
R1、Ar1With Ar2It is identical or different, separately selected from substituted or unsubstituted carbon atom number be 1-40 alkyl, take
Generation or unsubstituted carbon atom number be 2-40 alkenyl, substituted or unsubstituted carbon atom number be 2-32 alkynyl, replace or not
Heterocyclylalkyl that naphthenic base that substituted carbon atom number is 3-40, substituted or unsubstituted carbon atom number are 2-40 replaces or not
Heteroarylalkyl that aralkyl that substituted carbon atom number is 7-40, substituted or unsubstituted carbon atom number are 2-40 replaces or not
Aryl that substituted carbon atom number is 6-40, substituted or unsubstituted carbon atom number are one of heteroaryl of 1-40；
Ar3Selected from singly-bound, substituted or unsubstituted carbon atom number be 1-40 alkylidene, substituted or unsubstituted carbon atom number be
Alkynylene that the alkenylene of 2-40, substituted or unsubstituted carbon atom number are 2-32, substituted or unsubstituted carbon atom number are 3-
40 ring alkylidene, substituted or unsubstituted carbon atom number are the heterocycloalkylene group of 2-40, substituted or unsubstituted carbon atom number
For the sub- aralkyl of 7-40, substituted or unsubstituted carbon atom number be 1-40 heteroarylidene, substituted or unsubstituted carbon atom
Miscellaneous sub- aralkyl, the substituted or unsubstituted carbon that arlydene that number is 6-40, substituted or unsubstituted carbon atom number are 2-40 are former
The ring alkenylene of subnumber 3-15, the miscellaneous alkynylene of substituted or unsubstituted carbon atom number 2-32, substituted or unsubstituted carbon atom
One of the miscellaneous alkenylene of number 2-15.
2. electroluminescent organic material according to claim 1, which is characterized in that the R1、Ar1、Ar2And Ar3Take
It is identical or different for base, and separately it is selected from deuterium, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted carbon atom number
The alkyl of 1-40, the naphthenic base of substituted or unsubstituted carbon atom number 3-40, substituted or unsubstituted carbon atom number 2-40 alkene
Base, the alkynyl of substituted or unsubstituted carbon atom number 2-32, the Heterocyclylalkyl of substituted or unsubstituted carbon atom number 2-40, substitution
Or the aralkyl of unsubstituted carbon atom number 7-40, substituted or unsubstituted carbon atom number 2-40 heteroarylalkyl, replace or not
The aryl of substituted carbon atom number 6-40, the heteroaryl of substituted or unsubstituted carbon atom number 1-40, substituted or unsubstituted carbon
The alkoxy of atomicity 1-40, the alkylamino of substituted or unsubstituted carbon atom number 1-40, substituted or unsubstituted carbon atom number
The fragrant amino of 6-30, alkylthio group, the substituted or unsubstituted carbon atom number 7-30 that substituted or unsubstituted carbon atom number is 1-40
Arylalkylamino, the heteroaryl amino of substituted or unsubstituted carbon atom number 1-24, substituted or unsubstituted carbon atom number be 1-45
AIkylsilyl groups, substituted or unsubstituted carbon atom number be that the arylsilyl groups of 6-50, substituted or unsubstituted carbon are former
Aryloxy group that subnumber is 6-30, substituted or unsubstituted carbon atom number are one of 6-30 arylthio.
3. electroluminescent organic material according to claim 1, which is characterized in that the R1、Ar1With Ar2It is identical or not
Together, being separately selected from substituted or unsubstituted carbon atom number is the aralkyl of 7-40, substituted or unsubstituted carbon atom number
For the heteroarylalkyl of 2-40, substituted or unsubstituted carbon atom number be 6-30 aryl, substituted or unsubstituted carbon atom number be
One of heteroaryl of 1-40.
4. electroluminescent organic material according to claim 1, which is characterized in that the Ar3Selected from substituted or unsubstituted
It is heteroarylidene that arlydene that carbon atom number is 6-40, substituted or unsubstituted carbon atom number are 1-40, substituted or unsubstituted
Sub- aralkyl that carbon atom number is 7-40, substituted or unsubstituted carbon atom number are one of miscellaneous sub- aralkyl of 2-40.
5. electroluminescent organic material according to claim 1, which is characterized in that the chemical formula 1 is following structuring
Close one of object:
6. electroluminescent organic material according to claim 1, which is characterized in that the Ar3Selected from substituted or unsubstituted
Phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthalene, substitution or not
Substituted dimethyl fluorenyl, substituted or unsubstituted dibenzofuran group, one in substituted or unsubstituted dibenzothiophene
Kind.
7. a kind of organic electroluminescence device, have including cathode, anode and one layer or more between the cathode and anode
Machine layer, which is characterized in that at least one layer includes claim 1 in one layer or more the organic layer between the cathode and anode
The electroluminescent organic material.
8. organic electroluminescence device according to claim 7, which is characterized in that the organic layer includes hole injection
Layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer.
9. organic electroluminescence device according to claim 7, which is characterized in that comprising described in claim 1 organic
The organic layer of electroluminescent material is hole transmission layer.
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