CN106946934A - A kind of material of main part and organic luminescent device containing flexible chain structure - Google Patents
A kind of material of main part and organic luminescent device containing flexible chain structure Download PDFInfo
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- CN106946934A CN106946934A CN201710197582.0A CN201710197582A CN106946934A CN 106946934 A CN106946934 A CN 106946934A CN 201710197582 A CN201710197582 A CN 201710197582A CN 106946934 A CN106946934 A CN 106946934A
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Abstract
The present invention provides a kind of material of main part and organic luminescent device containing flexible chain structure, belongs to organic photoelectrical material technical field, solves the technical problem of the low luminescent properties difference of organic photoelectrical material luminous efficiency in the prior art.The material of main part containing flexible chain structure that the present invention is provided connects electron withdraw group and electron-donating group with flexible chain, and the conjugation for interrupting electron withdraw group and electron-donating group is connected, so as to increase substantially triplet.Organic luminescent device prepared by the material of main part containing flexible chain structure provided using the present invention has good luminescent properties, and luminous efficiency reaches as high as 10.8cd/A, and driving voltage, up to 3.1V, is a kind of excellent OLED material.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of material of main part containing flexible chain structure and has
Machine luminescent device.
Background technology
Organic electroluminescent refers to organic material under electric field action, and what is excited and light by electric current and electric field shows
As.Organic electroluminescent LED (OLED) is the Display Technique of new generation that display is realized using this phenomenon.From U.S. in 1987
State Kodak Company Tang C.W. and Vanslyke S.A. made the organic electroluminescence device of first function admirable with
Come, ORGANIC ELECTROLUMINESCENCE DISPLAYS causes the great interest of people because it has the advantage that.
In second generation organic electromechanical phosphorescent material, in order to avoid phosphorescence luminous efficiency caused by triplet state is quenched as far as possible
Reduction, it is use host-guest system structures more.It is exactly subject highlighting as good one indispensable basic demand of material of main part
The triplet of compound is higher than guest compound, because only that so, triplet excitons could be confined in luminescent layer, from
And suppress object energy adverse current and arrive main body.Conjugated degree in molecular structure has the influence of negative correlation to triplet：Point
Sub- conjugated degree is lower, and triplet is higher.For blue-light device, its triplet to main body has more severe
The requirement at quarter.In containing electron and electrophilic material of main part, although tentatively solve the problem of carrier balance is transmitted,
But the charge-transfer complex totally unfavorable to luminescent spectrum is result in acceptor connected mode due to special in molecular structure
Formation, secondly, excessively rigid structure is easy to form strong pi-conjugated effect in the molecule, so as to significantly weaken three lines
State energy level.
The content of the invention
In view of this, it is an object of the invention to provide a kind of material of main part and luminescent device containing flexible chain structure.This
Invention compound connects electron withdraw group and electron-donating group with flexible chain, interrupts the conjugation of electron withdraw group and electron-donating group
Connection, so as to obtain a kind of material of main part with more high triplet energy level.Using main body material of the present invention containing flexible chain structure
Expect the organic luminescent device prepared, also with higher luminous efficiency, lower driving voltage.
Present invention firstly provides a kind of material of main part containing flexible chain structure, its general structure is as shown in Formulas I or II：
Wherein, R1、R3Independent is fragrant selected from hydrogen, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50
Any one in alkyl, substituted or unsubstituted C6-C50 arylamine, substituted or unsubstituted C5-C50 heteroaryl；
X is selected from oxygen, sulphur or CR2R2, R2Alkyl or substituted or unsubstituted C6- selected from substituted or unsubstituted C1-C3
C12 aryl.
It is preferred that, the material of main part containing flexible chain structure, shown in following any structure：
Wherein, R1、R3Independent is fragrant selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30
Any one in alkyl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C5-C30 heteroaryl；R2Choosing
From methyl or phenyl.
It is preferred that, described R1、R3Any one independent in hydrogen or following structure：
M is selected from hydrogen or C1~C3 alkyl.
It is preferred that, the material of main part containing flexible chain structure, as shown in formula 1~20：
The present invention also provides a kind of organic luminescent device, including first electrode, second electrode and is placed between two electrodes
One or more organic layers, at least one organic layer includes the material of main part of the present invention containing flexible chain structure.
Beneficial effects of the present invention：
The present invention provides a kind of material of main part and organic luminescent device containing flexible chain structure, compared with prior art, this
The material of main part containing flexible chain structure provided is provided electron withdraw group and electron-donating group are connected with flexible chain, interrupt electrophilic
The conjugation connection of group and electron-donating group, so as to increase substantially triplet.Contain flexible chain using what the present invention was provided
Organic luminescent device prepared by the material of main part of structure, test result indicate that, luminous efficiency reaches as high as 10.8cd/A, and drives
Dynamic voltage is minimum can reach 3.1V, is a kind of excellent OLED material.
Embodiment
Technical scheme below in conjunction with the embodiment of the present invention is clearly and completely described, it is clear that described implementation
Example only a part of embodiment of the invention, rather than whole embodiments.Based on the embodiment in the present invention, this area is common
The every other embodiment that technical staff is obtained under the premise of creative work is not made, belongs to the model that the present invention is protected
Enclose.
It should be noted that unless otherwise prescribed, the implication of scientific and technical terminology used in the present invention and people in the art
The implication that member is generally understood is identical.
Present invention firstly provides a kind of material of main part containing flexible chain structure, its general structure is as shown in Formulas I or II：
Wherein, R1、R3Independent is fragrant selected from hydrogen, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50
Any one in alkyl, substituted or unsubstituted C6-C50 arylamine, substituted or unsubstituted C5-C50 heteroaryl；
X is selected from oxygen, sulphur or CR2R2, R2Alkyl or substituted or unsubstituted C6- selected from substituted or unsubstituted C1-C3
C12 aryl.
According to the present invention, the aryl refers on the aromatic core carbon of aromatic hydrocarbon molecule remove after a hydrogen atom, is left monad radical
The general name of group, it can be monocyclic aryl or fused ring aryl, for example, may be selected from phenyl, xenyl, naphthyl, anthryl, phenanthryl or pyrene
Base etc., but not limited to this.
The arylamine refers to the amine with armaticity substituent, i.e.-NH2,-NH- or nitrogen-containing group be connected on aromatic hydrocarbon.
The heteroaryl refers to the group that one or more of aromatic hydrocarbyl aromatic core carbon is obtained by hetero atom replacement
General name, the hetero atom includes but is not limited to oxygen, sulphur and nitrogen-atoms, and the aromatic heterocycle can be monocyclic or condensed ring, for example may be used
Selected from pyridine radicals, pyrimidine radicals, benzo pyrimidine radicals, carbazyl, triazine radical, benzothiazolyl or benzimidazolyl etc., but it is not limited to
This.
According to the present invention, the material of main part containing flexible chain structure is preferably selected from shown in following any structure：
The R2It is preferably selected from methyl or phenyl；The R1、R3It is preferred that independent is selected from hydrogen, substituted or unsubstituted C6-
It is C30 aryl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted
Any one in C6-C30 heteroaryl, is more preferably selected from any one in hydrogen or following structure：
Wherein, M is selected from hydrogen or C1~C3 alkyl.
As an example, the material of main part containing flexible chain structure, is not particularly limited, preferably as shown in formula 1~20：
It is enumerated above some specific structure types of the material of main part of the present invention containing flexible chain structure, but this hair
The bright material of main part containing flexible chain structure is not limited to these listed chemical constitutions, every with Formulas I or any knots of II
Based on structure, R1, R2, R3It should be all included for group as defined above.
The preparation method of material of main part of the present invention containing flexible chain structure, can pass through following route reaction production
Any material of main part containing flexible chain structure shown in I or II：
Wherein, R1、R3Independent is fragrant selected from hydrogen, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50
Any one in alkyl, substituted or unsubstituted C6-C50 arylamine, substituted or unsubstituted C5-C50 heteroaryl；X is selected
From oxygen, sulphur or CR2R2, R2Alkyl or substituted or unsubstituted C6-C12 aryl selected from substituted or unsubstituted C1-C3.
The present invention does not have particular/special requirement to the reaction condition of above-mentioned all kinds of reactions, with well known to those skilled in the art such
The normal condition of reaction.The present invention has no particular limits to the source of the raw material employed in above-mentioned all kinds of reactions, can
Think commercially available prod or prepared using preparation method well-known to those skilled in the art.Wherein, the R1、R2、R3Choosing
Select same as above, will not be repeated here.
The present invention also provides a kind of organic luminescent device.What the organic luminescent device was well known to those skilled in the art
Organic luminescent device, organic luminescent device of the present invention includes first electrode, second electrode and is placed between two electrodes
One or more organic layers.The organic layer preferably include hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer,
At least one layer in hole blocking layer, electron transfer layer and electron injecting layer.It is preferred that containing institute of the present invention in described luminescent layer
State the material of main part containing flexible chain structure.
Embodiment 1：CompoundSynthesis
Take 1mol compounds A-1 to add THF dissolvings, 1mol NBS THF solution is added dropwise, 1h is reacted at room temperature, has been reacted
Cheng Hou, THF is spin-dried for, and crude product crosses silicagel column and obtains product 456mmol A.
Mass spectrum m/z：261.03 (calculated values 260.98), the above results confirm that it is target product to obtain product.
Embodiment 2：CompoundSynthesis
Take 1mol compounds B-1 to add THF dissolvings, 3mol NBS THF solution is added dropwise, 1h is reacted at room temperature, has been reacted
Cheng Hou, THF is spin-dried for, and crude product crosses silicagel column and obtains product 831mmol B-2.
500mmol B-2 are taken, 500mmol phenyl boric acids are added, nitrogen protection is lower to be added, the triphenyl phosphorus palladiums of 5mmol tetra-,
1.5mol sodium carbonate, toluene：Ethanol：Water=4:1:1 mixed solution, back flow reaction is stayed overnight, and is crossed pillar and is obtained product B
422mmol。
Mass spectrum m/z：352.11 (calculated values 352.99), the above results confirm that it is target product to obtain product.
Take 1mol compounds B-1 to add THF dissolvings, 3mol NBS THF solution is added dropwise, 1h is reacted at room temperature, has been reacted
Cheng Hou, THF is spin-dried for, and crude product crosses silicagel column and obtains product 831mmol B-2.
500mmol B-2 are taken, 500mmol carbazoles are added, nitrogen protection is lower to add 5mmolPd2 (dba) 31.5mol carbonic acid
Sodium, toluene solution, back flow reaction is stayed overnight, and is crossed pillar and is obtained products C 405mmol.
Mass spectrum m/z：442.17 (calculated values 442.01), the above results confirm that it is target product to obtain product.
Embodiment 4：CompoundSynthesis
1mol compound D-1 is taken to add solvent toluene, to the equivalent of bromo-iodobenzene 1, Pd2(dba)310mmol, potassium tert-butoxide
12h is reacted under 3mmol, tri-butyl phosphine 20mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, solvent is spin-dried for, slightly
Product cross silicagel column, obtain product 842mmol D-2.
Take 842mol compound D-2 to add solvent anhydrous tetrahydro furan, methyl-magnesium-bromide 5e.q. THF solution be added dropwise,
50 degrees Celsius are reacted 12 hours, after reaction terminates, are quenched reaction with saturated aqueous ammonium chloride, and ethyl acetate extracts, dry, dense
Contract, cross pillar, obtain product 621mmol D-3.
842mol compound D-3 is taken, solvent phosphoric acid is added, reacted 6 hours at a reflux temperature, reaction is poured into after terminating
In water, solid filtering crosses pillar, obtains product 450mmol D.
Mass spectrum m/z：286.98 (calculated values 287.03), the above results confirm that it is target product to obtain product.
The compound of embodiment 5Synthesis
1mol compound D-1 is taken to add solvent toluene, to the equivalent of bromo-iodobenzene 1, Pd2(dba)310mmol, potassium tert-butoxide
12h is reacted under 3mmol, tri-butyl phosphine 20mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, solvent is spin-dried for, slightly
Product cross silicagel column, obtain product 842mmol D-2.
Take 842mol compound D-2 to add solvent anhydrous tetrahydro furan, phenyl-magnesium-bromide 5e.q. THF solution be added dropwise,
50 degrees Celsius are reacted 12 hours, after reaction terminates, are quenched reaction with saturated aqueous ammonium chloride, and ethyl acetate extracts, dry, dense
Contract, cross pillar, obtain product 602mmol E-1.
602mol compound E-1 is taken, solvent phosphoric acid is added, reacted 6 hours at a reflux temperature, reaction is poured into after terminating
In water, solid filtering crosses pillar, obtains product 407mmol E.
Mass spectrum m/z：411.23 (calculated values 411.06), the above results confirm that it is target product to obtain product.
Embodiment 6：The preparation of compound 1
Step1, takes 100mmol compound 1-1, adds solvents tetrahydrofurane, the equivalent of allyl tributyltin 4, four or three
12h is reacted under the equivalent of phenyl phosphorus palladium 0.5%, the equivalents of CsF 2, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for molten
Agent, crude product crosses silicagel column, obtains product 44mmol 1-2.
Step2, under 0 degree Celsius, 132mmol 9-BBN is dissolved in THF solution, adds 44mmol1-2, room temperature
Lower stirring 15min, is warming up to 35 degrees Celsius, reacts 3h, then mixed liquor is transferred to equipped with B 66mmol, four triphenyl phosphorus palladiums
0.88mmol, sodium carbonate 132mmol toluene：Ethanol：Water=4:1:In 1 mixed solution, reflux temperature reaction is warming up to
24h.Crude product crosses silicagel column, obtains product 20mmol, 1-3.
Step3, takes 20mmol compound 1-3 to add solvent toluene, the equivalents of 1-4 1, the 0.2mmol of Pd2 (dba) 3, uncle
12h is reacted under butanol potassium 60mmol, tri-butyl phosphine 0.4mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for
Solvent, crude product crosses silicagel column, obtains product 16mmol 1.
Mass spectrum m/z：669.15 (calculated values 669.23), the above results confirm that it is target product to obtain product.
Embodiment 7：The synthesis of compound 2
Step1, takes 100mmol compound 1-1, adds solvents tetrahydrofurane, the equivalent of allyl tributyltin 4, four or three
12h is reacted under the equivalent of phenyl phosphorus palladium 0.5%, the equivalents of CsF 2, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for molten
Agent, crude product crosses silicagel column, obtains product 44mmol 1-2.
Step2, under 0 degree Celsius, 132mmol 9-BBN is dissolved in THF solution, adds 44mmol 1-2, room temperature
Lower stirring 15min, is warming up to 35 degrees Celsius, reacts 3h, then mixed liquor is transferred to equipped with D 66mmol, four triphenyl phosphorus palladiums
0.88mmol, sodium carbonate 132mmol toluene：Ethanol：Water=4:1:In 1 mixed solution, reflux temperature reaction is warming up to
24h.Crude product crosses silicagel column, obtains product 20mmol, 2-1.
Step3, takes 20mmol compound 2-1 to add solvent toluene, the equivalents of 1-4 1, Pd2(dba)30.2mmol, tertiary fourth
12h is reacted under potassium alcoholate 60mmol, tri-butyl phosphine 0.4mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for molten
Agent, crude product crosses silicagel column, obtains product 16mmol 2.
Mass spectrum m/z：603.22 (calculated values 603.27), the above results confirm that it is target product to obtain product.
Embodiment 8：The synthesis of compound 3
Step1, takes 100mmol compound 3-1, adds solvents tetrahydrofurane, the equivalent of allyl tributyltin 4, four or three
12h is reacted under the equivalent of phenyl phosphorus palladium 0.5%, the equivalents of CsF 2, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for molten
Agent, crude product crosses silicagel column, obtains product 44mmol 3-2.
Step2, under 0 degree Celsius, 132mmol 9-BBN is dissolved in THF solution, adds 44mmol 3-2, room temperature
Lower stirring 15min, is warming up to 35 degrees Celsius, reacts 3h, then mixed liquor is transferred to equipped with A 66mmol, four triphenyl phosphorus palladiums
0.88mmol, sodium carbonate 132mmol toluene：Ethanol：Water=4:1:In 1 mixed solution, reflux temperature reaction is warming up to
24h.Crude product crosses silicagel column, obtains product 20mmol, 3-3.
Step3, takes 20mmol compound 3-3 to add solvent toluene, the equivalents of 1-4 1, the 0.2mmol of Pd2 (dba) 3, uncle
12h is reacted under butanol potassium 60mmol, tri-butyl phosphine 0.4mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for
Solvent, crude product crosses silicagel column, obtains product 16mmol 3.
Mass spectrum m/z：517.63 (calculated values 517.17), the above results confirm that it is target product to obtain product.
Embodiment 9：The synthesis of compound 4
Step1, takes 100mmol compound 3-1, adds solvents tetrahydrofurane, the equivalent of allyl tributyltin 4, four or three
12h is reacted under the equivalent of phenyl phosphorus palladium 0.5%, the equivalents of CsF 2, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for molten
Agent, crude product crosses silicagel column, obtains product 44mmol 3-2.
Step2, under 0 degree Celsius, 132mmol 9-BBN is dissolved in THF solution, adds 44mmol 3-2, room temperature
Lower stirring 15min, is warming up to 35 degrees Celsius, reacts 3h, then mixed liquor is transferred to equipped with D 66mmol, four triphenyl phosphorus palladiums
0.88mmol, sodium carbonate 132mmol toluene：Ethanol：Water=4:1:In 1 mixed solution, reflux temperature reaction is warming up to
24h.Crude product crosses silicagel column, obtains product 20mmol, 4-1.
Step3, takes 20mmol compound 4-1 to add solvent toluene, the equivalents of 1-4 1, the 0.2mmol of Pd2 (dba) 3, uncle
12h is reacted under butanol potassium 60mmol, tri-butyl phosphine 0.4mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for
Solvent, crude product crosses silicagel column, obtains product 16mmol 4.
Mass spectrum m/z：543.52 (calculated values 543.22), the above results confirm that it is target product to obtain product.
Embodiment 10：The synthesis of compound 5
Step1, takes 100mmol compound 1-1, adds solvents tetrahydrofurane, the equivalent of allyl tributyltin 4, four or three
12h is reacted under the equivalent of phenyl phosphorus palladium 0.5%, the equivalents of CsF 2, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for molten
Agent, crude product crosses silicagel column, obtains product 44mmol 1-2.
Step2, under 0 degree Celsius, 132mmol 9-BBN is dissolved in THF solution, adds 44mmol 1-2, room temperature
Lower stirring 15min, is warming up to 35 degrees Celsius, reacts 3h, then mixed liquor is transferred to equipped with 5-1 66mmol, four triphenyl phosphorus
Palladium 0.88mmol, sodium carbonate 132mmol toluene：Ethanol：Water=4:1:In 1 mixed solution, reflux temperature reaction is warming up to
24h.Crude product crosses silicagel column, obtains product 20mmol, 5-2.
Step3, takes 20mmol compound 5-2 to add solvent toluene, the equivalents of 5-3 1, the 0.2mmol of Pd2 (dba) 3, uncle
12h is reacted under butanol potassium 60mmol, tri-butyl phosphine 0.4mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for
Solvent, crude product crosses silicagel column, obtains product 16mmol 5.
Mass spectrum m/z：643.15 (calculated values 643.21), the above results confirm that it is target product to obtain product.
Embodiment 11：The synthesis of compound 6
By the R in embodiment 71Group replaces with R as implied above1Group, other steps are same as Example 7, changed
Compound 6.Mass spectrum m/z：653.42 (calculated values：653.28).
Embodiment 12：The synthesis of compound 7
By the R in embodiment 81Group replaces with R as implied above1Group, other steps are same as Example 8, changed
Compound 7.Mass spectrum m/z：567.74 (calculated values：567.19).
Embodiment 13：The synthesis of compound 8
By the R in embodiment 91Group replaces with R as implied above1Group, other steps are same as Example 9, changed
Compound 8.Mass spectrum m/z：593.51 (calculated values：593.24).
Embodiment 14：The synthesis of compound 9
By the R in embodiment 101Group replaces with R as implied above1Group, other steps are same as in Example 10, obtain
Compound 9.Mass spectrum m/z：699.66 (calculated values：699.23).
Embodiment 15：The synthesis of compound 10
By the R in embodiment 71Group replaces with R as implied above1Group, other steps are same as Example 7, changed
Compound 10.Mass spectrum m/z：679.57 (calculated values：679.30).
Embodiment 16：The synthesis of compound 11
By the R in embodiment 81Group replaces with R as implied above1Group, other steps are same as Example 8, changed
Compound 11.Mass spectrum m/z：593.65 (calculated values：593.20).
Embodiment 17：The synthesis of compound 12
By the R in embodiment 91Group replaces with R as implied above1Group, other steps are same as Example 9, changed
Compound 12.Mass spectrum m/z：619.42 (calculated values 619.25).
Embodiment 18：The synthesis of compound 13
Step1, takes 100mmol compound 1-1, adds solvents tetrahydrofurane, the equivalent of allyl tributyltin 4, four or three
12h is reacted under the equivalent of phenyl phosphorus palladium 0.5%, the equivalents of CsF 2, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for molten
Agent, crude product crosses silicagel column, obtains product 44mmol 1-2.
Step2, under 0 degree Celsius, 132mmol 9-BBN is dissolved in THF solution, adds 44mmol 1-2, room temperature
Lower stirring 15min, is warming up to 35 degrees Celsius, reacts 3h, then mixed liquor is transferred to equipped with C 66mmol, four triphenyl phosphorus palladiums
0.88mmol, sodium carbonate 132mmol toluene：Ethanol：Water=4:1:In 1 mixed solution, reflux temperature reaction is warming up to
24h.Crude product crosses silicagel column, obtains product 20mmol, 13-1.
Step3, takes 20mmol compound 13-1 to add solvent toluene, the equivalents of 13-2 1, Pd2(dba)30.2mmol, uncle
12h is reacted under butanol potassium 60mmol, tri-butyl phosphine 0.4mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for
Solvent, crude product crosses silicagel column, obtains product 16mmol 13.
Mass spectrum m/z：758.25 (calculated values 758.25), the above results confirm that it is target product to obtain product.
Embodiment 19：The synthesis of compound 14
By the R in embodiment 71Group replaces with R as implied above1Group, other steps are same as Example 2, changed
Compound 14.Mass spectrum m/z：768.89 (calculated values：768.33).
Embodiment 20：The synthesis of compound 15
By the R in embodiment 81Group replaces with R as implied above1Group, other steps are same as Example 3, changed
Compound 15.Mass spectrum m/z：682.35 (calculated values：682.23).
Embodiment 21：The synthesis of compound 16
Step1, takes 100mmol compound 3-1, adds solvents tetrahydrofurane, the equivalent of allyl tributyltin 4, four or three
12h is reacted under the equivalent of phenyl phosphorus palladium 0.5%, the equivalents of CsF 2, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for molten
Agent, crude product crosses silicagel column, obtains product 44mmol 3-2.
Step2, under 0 degree Celsius, 132mmol 9-BBN is dissolved in THF solution, adds 44mmol 3-2, room temperature
Lower stirring 15min, is warming up to 35 degrees Celsius, reacts 3h, then mixed liquor is transferred to equipped with E 66mmol, four triphenyl phosphorus palladiums
0.88mmol, sodium carbonate 132mmol toluene：Ethanol：Water=4:1:In 1 mixed solution, reflux temperature reaction is warming up to
24h.Crude product crosses silicagel column, obtains product 20mmol, 16-1.
Step3, takes 20mmol compound 16-1 to add solvent toluene, the equivalents of 16-2 1, Pd2(dba)30.2mmol, uncle
12h is reacted under butanol potassium 60mmol, tri-butyl phosphine 0.4mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for
Solvent, crude product crosses silicagel column, obtains product 16mmol 16.
Mass spectrum m/z:832.65 (calculated values：832.31).
Embodiment 22：The synthesis of compound 17
By the R in embodiment 71Group replaces with R as implied above1Group, other steps are same as Example 1, changed
Compound 17.Mass spectrum m/z:758.54 (calculated values：758.25).
Embodiment 23：The synthesis of compound 18
Step1, takes 100mmol compound 1-1, adds solvents tetrahydrofurane, the equivalent of allyl tributyltin 4, four or three
12h is reacted under the equivalent of phenyl phosphorus palladium 0.5%, the equivalents of CsF 2, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for molten
Agent, crude product crosses silicagel column, obtains product 44mmol 1-2.
Step2, under 0 degree Celsius, 132mmol 9-BBN is dissolved in THF solution, adds 44mmol 1-2, room temperature
Lower stirring 15min, is warming up to 35 degrees Celsius, reacts 3h, then mixed liquor is transferred to equipped with E 66mmol, four triphenyl phosphorus palladiums
0.88mmol, sodium carbonate 132mmol toluene：Ethanol：Water=4:1:In 1 mixed solution, reflux temperature reaction is warming up to
24h.Crude product crosses silicagel column, obtains product 20mmol, 18-1.
Step3, takes 20mmol compound 18-1 to add solvent toluene, the equivalents of 18-2 1, Pd2(dba)30.2mmol, uncle
12h is reacted under butanol potassium 60mmol, tri-butyl phosphine 0.4mmol, nitrogen displacement three times, reflux temperature.After the completion of reaction, it is spin-dried for
Solvent, crude product crosses silicagel column, obtains product 16mmol 18.
Mass spectrum m/z：892.89 (calculated values：892.36).
Embodiment 24：The synthesis of compound 19
By the R in embodiment 81Group replaces with R as implied above1Group, other steps are same as Example 8, changed
Compound 19.Mass spectrum m/z：682.35 (calculated values：682.23).
Embodiment 25：The synthesis of compound 20
By the R in embodiment 91Group replaces with R as implied above1Group, other steps are same as Example 9, changed
Compound 20.Mass spectrum m/z：708.65 (calculated values：708.28).
Contrast Application Example 1：
It is anode to take transparent glass, is dried after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, upper
State in anode grid substrate that vacuum evaporation NPB is as hole transmission layer, evaporation rate is 0.1nm/s, and evaporation thickness is 70nm.In hole
Vacuum evaporation mCP/FIrpic is as luminescent layer in transport layer, and doping concentration is 15wt%, and evaporation rate is 0.005nm/s, steams
Plating thickness is 30nm.The vacuum evaporation Alq on luminescent layer3As electron transfer layer, evaporation rate is 0.01nm/s, evaporation thickness
For 50nm.Vacuum evaporation Al layers as negative electrode on the electron transport layer, and thickness is 200nm.
Application example 1：
It is anode to take transparent glass, is dried after ultrasonic cleaning as in vacuum chamber, is evacuated to 5 × 10-5Pa, upper
State in anode grid substrate that vacuum evaporation NPB is as hole transmission layer, evaporation rate is 0.1nm/s, and evaporation thickness is 70nm.In hole
Vacuum evaporation compound 1/FIrpic is as luminescent layer in transport layer, and doping concentration is 15wt%, and evaporation rate is 0.005nm/
S, evaporation thickness is 30nm.The vacuum evaporation Alq on luminescent layer3As electron transfer layer, evaporation rate is 0.01nm/s, evaporation
Thickness is 50nm.Vacuum evaporation Al layers as negative electrode on the electron transport layer, and thickness is 200nm.
Application example 2：
Change the compound 1 in Application Example 1 into compound 2.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 3：
Change the compound 1 in Application Example 1 into compound 3.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 4：
Change the compound 1 in Application Example 1 into compound 4.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 5：
Change the compound 1 in Application Example 1 into compound 5.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 6：
Change the compound 1 in Application Example 1 into compound 6.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 7：
Change the compound 1 in Application Example 1 into compound 7.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 8：
Change the compound 1 in Application Example 1 into compound 8.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 9：
Change the compound 1 in Application Example 1 into compound 9.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 10：
Change the compound 1 in Application Example 1 into compound 10.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 11：
Change the compound 1 in Application Example 1 into compound 11.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 12：
Change the compound 1 in Application Example 1 into compound 12.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 13：
Change the compound 1 in Application Example 1 into compound 13.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 14：
Change the compound 1 in Application Example 1 into compound 14.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 15：
Change the compound 1 in Application Example 1 into compound 15.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 16：
Change the compound 1 in Application Example 1 into compound 16.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 17：
Change the compound 1 in Application Example 1 into compound 17.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 18：
Change the compound 1 in Application Example 1 into compound 18.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 19：
Change the compound 1 in Application Example 1 into compound 19.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 20：
Change the compound 1 in Application Example 1 into compound 20.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Measure embodiment 1：The luminescent properties of comparative sample and sample 1-20
Comparative sample and sample 1-20 are to evaluate driving voltage, luminous efficiency using Keithley SMU235, PR650,
The results are shown in Table 1：
The characteristics of luminescence of luminescent device prepared by the embodiment of the present invention of table 1
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from claim
In the case of the spirit and scope of the invention limited, those of ordinary skill in the art can carry out various forms and details to it
On change.
Claims (5)
1. a kind of material of main part containing flexible chain structure, its general structure is as shown in Formulas I or II：
Wherein, R1、R3Independent is selected from hydrogen, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50 aralkyls
Any one in base, substituted or unsubstituted C6-C50 arylamine, substituted or unsubstituted C5-C50 heteroaryl；
X is selected from oxygen, sulphur or CR2R2, R2Alkyl or substituted or unsubstituted C6-C12 virtues selected from substituted or unsubstituted C1-C3
Base.
2. a kind of material of main part containing flexible chain structure according to claim 1, it is characterised in that following any structure institute
Show：
Wherein, R1、R3Independent is selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyls
Any one in base, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C5-C30 heteroaryl；R2It is selected from
Methyl or phenyl.
3. a kind of material of main part containing flexible chain structure according to claim 1, it is characterised in that described R1、R3It is independent
Any one in hydrogen or following structure：
M is selected from hydrogen or C1~C3 alkyl.
4. a kind of material of main part containing flexible chain structure according to any one of claims 1 to 3, it is characterised in that such as formula 1
Shown in~20 any one：
5. a kind of organic luminescent device, including first electrode, second electrode and it is placed in one or more organic between two electrodes
Layer, it is characterised in that at least one organic layer includes the main body containing flexible chain structure as described in claim 1-4 any one
Material.
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Application publication date: 20170714 |