CN107325036A - A kind of electroluminescent organic material and its organic luminescent device - Google Patents

A kind of electroluminescent organic material and its organic luminescent device Download PDF

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CN107325036A
CN107325036A CN201710568887.8A CN201710568887A CN107325036A CN 107325036 A CN107325036 A CN 107325036A CN 201710568887 A CN201710568887 A CN 201710568887A CN 107325036 A CN107325036 A CN 107325036A
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organic material
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孙可
孙可一
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of electroluminescent organic material and its organic luminescent device, belongs to organic photoelectrical material technical field.Solve the technical problem of the luminescent properties such as organic photoelectrical material luminous efficiency is low in the prior art, driving voltage is higher difference.Electroluminescent organic material of the present invention is a kind of novel bipolarity electroluminescent organic material, can significantly improve the luminous efficiency of device with electron withdraw group and the group for pushing away electronic effect.Parent nucleus uses the conjugation group tetraphenylethylene with symmetrical structure, and with preferable heat endurance, the service life of device will extend.Test result indicates that, the organic luminescent device prepared using the electroluminescent organic material of the present invention, luminous efficiency reaches as high as 20.3cd/A, the minimum 3.5V of driving voltage, is a kind of excellent OLED material.

Description

A kind of electroluminescent organic material and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of electroluminescent organic material and its organic hair Optical 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.In over the past thirty years, organic electroluminescent technology fast development, its partial properties is already close to even having surmounted inorganic half Conductor material, is expected to challenge traditional CRT, LCD technology in giant-screen and over-large screen display system field.
In OLED research, the selection of organic material plays conclusive effect.The organic material master used in OLED There are hole-injecting material, hole mobile material, luminescent material, electron transport material and electron injection material etc..In general, All holes or electron-transporting type material of main part doping guest emitter formation luminescent layer, exciton recombination region can be optionally inclined Certain upper one side, so as to cause device efficiency and photochromic change, very serious may cause the energy between triplet to be quenched Go out, cause luminous efficiency under high brightness to be roll-offed seriously.In addition, the driving voltage of device is higher, it is also not satisfactory.
The content of the invention
In view of this, it is an object of the invention to provide a kind of electroluminescent organic material using tetraphenylethylene as parent nucleus And its organic luminescent device, the organic luminescent device prepared using a kind of electroluminescent organic material of the present invention, with more High luminous efficiency, and lower driving voltage.
Present invention firstly provides a kind of electroluminescent organic material, its general structure is as shown in I or II：
Wherein, M is to push away electron heterocycles containing nitrogen-atoms.
It is preferred that, any one of the M in following structure：
Wherein, Ar be selected from substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 aralkyl, substitution or Any one in unsubstituted C6-C50 heteroaryls；R1、R2Independent is selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, takes Generation or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 aralkyl, substituted or unsubstituted C6-C50 arylamine, take Generation or unsubstituted C3-C50 heteroaryls in any one；
X is selected from oxygen, sulphur, SO2、CH2、C(CH3)2Or CPh2。
It is preferred that, described Ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aralkyls Any one in base, substituted or unsubstituted C6-C30 heteroaryls；R1、R2Independent is selected from hydrogen, substituted or unsubstituted C1- C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aralkyl, substituted or unsubstituted C6- Any one in C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls.
It is preferred that, a kind of described electroluminescent organic material, any one in following 1-112 structures：
The present invention also provides a kind of organic luminescent device, including first electrode, second electrode and be placed in two electrode it Between one or more organic compound layers, at least one organic compound layer include at least one Organic Electricity of the present invention Electroluminescent material.
It is preferred that, the organic compound layer includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electricity At least one layer in sub- transport layer, electron injecting layer.
Beneficial effects of the present invention：
The present invention provides a kind of electroluminescent organic material and its organic illuminator based on using tetraphenylethylene as parent nucleus Part.Tetraphenylethylene of the present invention is the electroluminescent organic material of parent nucleus with electron withdraw group and pushes away electronic effect Group, be a kind of novel bipolarity electroluminescent organic material, the luminous efficiency of device can be significantly improved.Parent nucleus is using tool There is the conjugation group tetraphenylethylene of symmetrical structure, with preferable heat endurance, the service life of device will extend.Experiment As a result show, the organic luminescent device prepared using the electroluminescent organic material of the present invention, luminous efficiency is reached as high as 20.3cd/A, the minimum 3.5V of driving voltage, are a kind of excellent OLED materials.
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.
Present invention firstly provides a kind of electroluminescent organic material, general structure is as shown in I or II：
Wherein, M is to push away electron heterocycles containing nitrogen-atoms.
In the present invention, parent nucleus uses the conjugation group tetraphenylethylene with symmetrical structure, with preferable heat endurance, Electron heterocycles M is pushed away so that with electron withdraw group and pushing away electronic effect in agent structure containing nitrogen-atoms by connecting simultaneously Group, obtain a kind of novel bipolarity electroluminescent organic material.The M is preferably five yuan or hexa-atomic containing N atoms Any one in heterocycle, more preferably following structure：
Wherein, Ar be selected from substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 aralkyl, substitution or Any one in unsubstituted C6-C50 heteroaryls；R1、R2Independent is selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, takes Generation or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 aralkyl, substituted or unsubstituted C6-C50 arylamine, take Generation or unsubstituted C3-C50 heteroaryls in any one；
X is selected from oxygen, sulphur, SO2、CH2、C(CH3)2Or CPh2。
It is preferred that, described Ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aralkyls Any one in base, substituted or unsubstituted C6-C30 heteroaryls；R1、R2Independent is selected from hydrogen, substituted or unsubstituted C1- C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aralkyl, substituted or unsubstituted C6- Any one in C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls.
It is preferred that, described electroluminescent organic material, any one in following 1-112 structures：
Electroluminescent organic material of the present invention can be prepared by following reaction scheme：
Wherein, M is to push away electron heterocycles containing nitrogen-atoms.
It is preferred that, any one of M in following structure：
Wherein, Ar be selected from substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 aralkyl, substitution or Any one in unsubstituted C6-C50 heteroaryls；R1、R2Independent is selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, takes Generation or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 aralkyl, substituted or unsubstituted C6-C50 arylamine, take Generation or unsubstituted C3-C50 heteroaryls in any one；
X is selected from oxygen, sulphur, SO2、CH2、C(CH3)2Or CPh2。
It is preferred that, described Ar is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aralkyls Any one in base, substituted or unsubstituted C6-C30 heteroaryls；R1、R2Independent is selected from hydrogen, substituted or unsubstituted C1- C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aralkyl, substituted or unsubstituted C6- Any one in C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls.
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.
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 compound layers, at least one organic compound layer include at least one organic electroluminescence of the present invention Luminescent material.The organic compound layer preferably includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electronics Contain organic electroluminescent of the present invention in transport layer and at least one layer in electron injecting layer, preferably described luminescent layer Material.
Embodiment 1：The preparation of compound 1
Step1, takes 100mmol double (4- bromobenzenes) ketones, adds 120mmol trimethyl silicane ethyl-acetylene, 1000mmol Triethylamine, 1mmol PdCl2(PPh3), 2mmol CuI, the tetrahydrofuran after degassing, argon gas is replaced three times, anti-under reflux temperature 10h is answered, crude product obtains product 86mmol compounds 1-1 via column chromatography.
Step2,86mmol fluorenes is dissolved in anhydrous THF, -78 degrees Celsius are cooled to, and 2.5 equivalent normal-butyls are slowly added dropwise Lithium, reacts 2h, adds the 1-1 of 2 equivalents THF solution.It is being to slowly warm up to react at room temperature 3h.After the completion of reaction, add a large amount of Water, there is white products precipitation, and filtering, filter cake obtains 71mmol products 1-2 via column chromatography.
Step3,71mmol 1-2 are dissolved in toluene, add the p-methyl benzenesulfonic acid of 2 equivalents, back flow reaction 2h.Instead Should after solvent is spin-dried for, obtain crude product via column chromatography, obtain 62mmol products 1-3.
Step4,1-3 62mmol are dissolved in tetrahydrofuran, add the butyl ammonium fluoride of 1 equivalent, back flow reaction 2h. Solvent is spin-dried for after reaction, crude product is obtained via column chromatography, 55mmol products 1-4 is obtained.
Step5, takes 1-4 55mmol, adds the carbazole of 1 equivalent, 165mmol potassium tert-butoxides, 0.6mmol Pd2(dba)3, Toluene, argon gas is replaced three times, adds 1.2mmol tri-butyl phosphines, and argon gas is replaced three times again, reacts 10h under reflux temperature, slightly Product obtains product 44mmol compounds 1 via column chromatography.
Embodiment 2：The preparation of compound 2
Step1~Step4 in Step1~Step4 be the same as Examples 1.
Step5, takes 1-4 55mmol, adds the boric acid of 1 equivalent, 165mmol sodium carbonate, the triphenyl phosphorus palladiums of 0.6mmol tetra-, Toluene, ethanol, the mixed solvent of water, argon gas is replaced three times, reacts 10h under reflux temperature, crude product is produced via column chromatography Product 47mmol compounds 2.
Embodiment 3：The synthesis of compound 3
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 4：The synthesis of compound 4
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 5：The synthesis of compound 5
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 6：The synthesis of compound 6
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 7：The synthesis of compound 7
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 8：The synthesis of compound 8
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 9：The synthesis of compound 11
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 10：The synthesis of compound 12
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 11：The synthesis of compound 25
Step0, takes 100mmol 2- bromo carbazoles, adds the pyridine boronic acid of 1 equivalent, 300mmol sodium carbonate, 1mmol tetra- Triphenyl phosphorus palladium, toluene, ethanol, the mixed solvent of water, argon gas is replaced three times, reacts 10h under reflux temperature, crude product is via post Chromatography, obtains product 86mmol compounds 25-0.
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 12：The synthesis of compound 29
Step0, takes 100mmol bromo -10H- phenthazine, adds the 1,3,5-triazines of 1 equivalent, 300mmol potassium tert-butoxides, 1mmol Pd2(dba)3, toluene, argon gas displacement three times, addition 2mmol tri-butyl phosphines, argon gas displacement three times again, backflow temperature The lower reaction 10h of degree, crude product obtains product 44mmol compounds 29-0 via column chromatography.
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 13：The synthesis of compound 33
M=carbazoles in embodiment 1 are changed to structure M as described above into, remaining step be the same as Example 1.
Embodiment 14：The synthesis of compound 42
M in embodiment 2 is changed to structure M as described above into, remaining step be the same as Example 2.
Embodiment 15：The synthesis of compound 57
Step1,86mmol fluorenes is dissolved in anhydrous THF, -78 degrees Celsius are cooled to, and 2.5 equivalent normal-butyls are slowly added dropwise Lithium, reacts 2h, adds the THF solution of the dibromobenzene MIBK of 2 equivalents.It is being to slowly warm up to react at room temperature 3h.After the completion of reaction, A large amount of water are added, there is white products precipitation, are filtered, filter cake obtains 71mmol products 57-1 via column chromatography.
Step2,71mmol57-1 is dissolved in toluene, adds the p-methyl benzenesulfonic acid of 2 equivalents, back flow reaction 2h.Instead Should after solvent is spin-dried for, obtain crude product via column chromatography, obtain 57-2 products 62mmol.
Step3, takes 57-2 62mmol, adds 1,2,4- triazoles of 0.5 equivalent, 180mmol potassium tert-butoxides, 0.6mmol Pd2(dba)3, toluene, argon gas displacement three times, addition 1.2mmol tri-butyl phosphines, argon gas displacement three times again, under reflux temperature 10h is reacted, crude product obtains product 44mmol compounds 57-3 via column chromatography.
Step4, takes 44mmol compound 57-3, adds the carbazole of 1 equivalent, 150mmol potassium tert-butoxides, 0.5mmol Pd2 (dba)3, toluene, argon gas displacement three times adds 1.0mmol tri-butyl phosphines, argon gas is replaced three times again, anti-under reflux temperature 10h is answered, crude product obtains product 28mmol compounds 57 via column chromatography.
Embodiment 16：The synthesis of compound 58
Step1~Step3 in Step1~Step3 be the same as Examples 57.
Step4, takes 44mmol compound 57-3, adds the 9- phenyl carbazole boric acid of 1 equivalent, 135mmol sodium carbonate, The triphenyl phosphorus palladiums of 0.5mmol tetra-, toluene, ethanol, the mixed solvent of water, argon gas is replaced three times, reacts 10h under reflux temperature, slightly Product obtains product 37mmol compounds 58 via column chromatography.
Embodiment 17：The synthesis of compound 59
M=carbazoles in embodiment 57 are changed to structure M as described above into, remaining step be the same as Example 57.Embodiment 18：The synthesis of compound 60
M=carbazoles in embodiment 57 are changed to structure M as described above into, remaining step be the same as Example 57.
The FD-MS values for the electroluminescent organic material that the embodiment of the present invention is prepared are shown in Table 1.
Compound FD-MS values prepared by the embodiment of the present invention of table 1
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 TAPC/FIrpic is as luminescent layer in transport layer, and doping concentration is 10wt%, 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 10wt%, 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, 2 are 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, 2 are 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, 2 are 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, 2 are 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, 2 are 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, 2 are 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, 2 are the results are shown in Table.
Application example 9：
Change the compound 1 in Application Example 1 into compound 11.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 10：
Change the compound 1 in Application Example 1 into compound 12.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 11：
Change the compound 1 in Application Example 1 into compound 29.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 12：
Change the compound 1 in Application Example 1 into compound 33.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 13：
Change the compound 1 in Application Example 1 into compound 42.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 14：
Change the compound 1 in Application Example 1 into compound 57.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 15：
Change the compound 1 in Application Example 1 into compound 58.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 16：
Change the compound 1 in Application Example 1 into compound 59.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 17：
Change the compound 1 in Application Example 1 into compound 60.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Measure embodiment 1：The luminescent properties of comparative sample and sample
Comparative sample and sample are that, using Keithley SMU235, PR650 evaluates luminous efficiency and driving voltage, knot Fruit is listed in Table 2 below：
The characteristics of luminescence of luminescent device prepared by the embodiment of the present invention of table 2
Above as can be seen that a kind of luminous organic material using tetraphenylethylene as parent nucleus of the present invention is in electroluminescent cell Applied in part, luminous efficiency reaches as high as 20.3cd/A, the minimum 3.5V of driving voltage, the larger hair for improving device Light efficiency, is luminous organic material of good performance.
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 (6)

1. a kind of electroluminescent organic material, its general structure is as shown in Formulas I or II：
Wherein, M is to push away electron heterocycles containing nitrogen-atoms.
2. a kind of electroluminescent organic material according to claim 1, it is characterised in that M appointing in following structure Meaning is a kind of：
Wherein, Ar is selected from substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 aralkyl, substitution or not taken Any one in the C6-C50 heteroaryls in generation；R1、R2It is independent selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substitution or Unsubstituted C6-C50 aryl, substituted or unsubstituted C6-C50 aralkyl, substituted or unsubstituted C6-C50 arylamine, substitution or Any one in unsubstituted C3-C50 heteroaryls；
X is selected from oxygen, sulphur, SO2、CH2、C(CH3)2Or CPh2。
3. a kind of electroluminescent organic material according to claim 2, it is characterised in that described Ar is selected from substitution or not Appointing in substituted C6-C30 aryl, substituted or unsubstituted C6-C30 aralkyl, substituted or unsubstituted C6-C30 heteroaryls Meaning is a kind of；R1、R2It is independent selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, take Generation or unsubstituted C6-C30 aralkyl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C3-C30 heteroaryls In any one.
4. a kind of electroluminescent organic material according to claim 2, it is characterised in that any in following structure It is a kind of：
5. a kind of organic luminescent device, including first electrode, second electrode and it is placed in one or more between two electrode Organic compound layer, it is characterised in that at least one organic compound layer is comprising at least one as Claims 1 to 4 is any one A kind of electroluminescent organic material described in.
6. a kind of organic luminescent device according to claim 5, it is characterised in that the organic compound layer includes hole At least one layer in implanted layer, hole transmission layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer.
CN201710568887.8A 2017-07-13 2017-07-13 A kind of electroluminescent organic material and its organic luminescent device Withdrawn CN107325036A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107057684A (en) * 2017-04-19 2017-08-18 长春海谱润斯科技有限公司 A kind of luminous organic material and its organic luminescent device based on bipolar phosphorescence derivative
CN111233753A (en) * 2020-02-16 2020-06-05 常州大学 Preparation method of AIE metal organogel
US20210313518A1 (en) * 2018-11-23 2021-10-07 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107057684A (en) * 2017-04-19 2017-08-18 长春海谱润斯科技有限公司 A kind of luminous organic material and its organic luminescent device based on bipolar phosphorescence derivative
US20210313518A1 (en) * 2018-11-23 2021-10-07 Lg Chem, Ltd. Novel compound and organic light emitting device comprising the same
US11980090B2 (en) * 2018-11-23 2024-05-07 Lg Chem, Ltd. Compound and organic light emitting device comprising the same
CN111233753A (en) * 2020-02-16 2020-06-05 常州大学 Preparation method of AIE metal organogel

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