CN107235858A - A kind of electroluminescent organic material and its organic luminescent device with electric transmission effect - Google Patents

A kind of electroluminescent organic material and its organic luminescent device with electric transmission effect Download PDF

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CN107235858A
CN107235858A CN201710568857.7A CN201710568857A CN107235858A CN 107235858 A CN107235858 A CN 107235858A CN 201710568857 A CN201710568857 A CN 201710568857A CN 107235858 A CN107235858 A CN 107235858A
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unsubstituted
substituted
electric transmission
transmission effect
layer
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孙可
孙可一
蔡辉
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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 with electric transmission effect, 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, service life is short difference.Compared with prior art, of the invention based on a kind of electroluminescent organic material and its organic luminescent device with electric transmission effect, the minimum 3.9V of driving voltage, luminous efficiency reaches as high as 21.4cd/A, is a kind of excellent OLED material.

Description

A kind of electroluminescent organic material and its organic light emission with electric transmission effect Device
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of organic electroluminescence with electric transmission effect Luminescent material and its organic luminescent device.
Background technology
Organic electroluminescence device, which has, includes luminescent layer and a pair of electrodes in luminescent layer both sides is constituted.When at two When applying electric field between electrode, electronics is injected by negative pole, and hole is injected by positive pole, and electronics and hole are recombined in luminescent layer Excitation state is formed, the energy transmitting light produced when excitation state returns to ground state.
Electroluminescent organic material has been developed for quite a long time, and fluorescent material is used as first generation luminescent material It is frequently used in luminescent layer.In addition, phosphor material as second generation light emitting host material also by suitable attention.Such as Applied Physics letters,Vol 74,No.3,P442-444,1999；US patent 6097147,6306238 Deng.
In the organic luminescent device prepared using phosphor material, the mobility of hole mobile material is far longer than electronics biography The mobility of defeated material, is 100 times of electron transport material mobility, about 10-3cm2/Vs.Possess preferable electron mobility, Can be effectively by electric transmission to the recombination region away from negative electrode.In addition, electron transport material will have preferable film forming, Otherwise in evaporation or spin coating, it is impossible to form uniform film, crystallization is easily produced, efficiency and the life-span of device is had a strong impact on. Currently, the most frequently used electron transport material usually contains the fragrant cyclics and metal combination of the electron deficient of nitrogen heterocycles Thing, such as Alq3, BAlq, Gaq3、Inq3, Liq, ZnBPO etc..Due to the influence of material property, come in reflection to device, device Driving voltage or luminous efficiency it is all undesirable.
To break through application limitation of the phosphor material in luminescent device, this invention contemplates a kind of with electric transmission effect Electroluminescent organic material and its organic light emitting apparatus, the present inventor's reality abundant for many years based on such product design manufacture is engaged in Business experience and professional knowledge, and coordinate the utilization of scientific principle, actively innovated, to found a kind of organic light emission of new structure Material and luminescent device.
The content of the invention
The invention provides a kind of electroluminescent organic material with electric transmission effect.Using one kind of the present invention Organic luminescent device prepared by electroluminescent organic material with electric transmission effect, with lower driving voltage, higher Luminous efficiency.
Present invention firstly provides a kind of electroluminescent organic material with electric transmission effect, with shown in formula I Structural formula：
Wherein, R is selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused ring aryls, taken Generation or unsubstituted C7-C60 aralkyl, substituted or unsubstituted C7-C60 aryl amines, substituted or unsubstituted C7-C60 aryl oxides Base, substituted or unsubstituted C7-C60 aromatic sulfides base, substituted or unsubstituted C6-C60 aryl phosphines, substituted or unsubstituted C4- Any one in C60 aromatic heterocycle.
It is preferred that, it is thick that described R is selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 It is cyclophane base, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C7-C30 aryl amines, substituted or unsubstituted C7-C30 aryl ether groups, substituted or unsubstituted C7-C30 aromatic sulfides base, substituted or unsubstituted C6-C30 aryl phosphines, substitution or not Any one in substituted C4-C30 aromatic heterocycle.
It is preferred that, a kind of electroluminescent organic material with electric transmission effect, appointing in following structure Meaning is a kind of：
The present invention also provides a kind of organic luminescent device of the electroluminescent organic material with electric transmission effect, including First electrode, second electrode and the one or more organic compound layers being placed between two electrode, at least one organises Compound layer includes at least one electroluminescent organic material with electric transmission effect.
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：
Compared with prior art, organic hair of a kind of electroluminescent organic material with electric transmission effect of the invention Optical device, the minimum 3.9V of driving voltage, luminous efficiency reaches as high as 21.4cd/A, 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.
Present invention firstly provides a kind of electroluminescent organic material with electric transmission effect, with shown in formula I Structural formula：
Wherein, R is selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused ring aryls, taken Generation or unsubstituted C7-C60 aralkyl, substituted or unsubstituted C7-C60 aryl amines, substituted or unsubstituted C7-C60 aryl oxides Base, substituted or unsubstituted C7-C60 aromatic sulfides base, substituted or unsubstituted C6-C60 aryl phosphines, substituted or unsubstituted C4- Any one in C60 aromatic heterocycle.
It is preferred that, it is thick that described R is selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 It is cyclophane base, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C7-C30 aryl amines, substituted or unsubstituted C7-C30 aryl ether groups, substituted or unsubstituted C7-C30 aromatic sulfides base, substituted or unsubstituted C6-C30 aryl phosphines, substitution or not Any one in substituted C4-C30 aromatic heterocycle.
It is described in the substituted aryl, the aralkyl of substitution, the arylamine of substitution, the heteroaryl of substitution according to the present invention Substituent may be selected from C1~C4 alkyl, C6-C18 aryl, and the number of the substituent is preferably 1~3.In the heteroaryl Hetero atom is preferably O, S, N or P.
It is preferred that, a kind of electroluminescent organic material with electric transmission effect, appointing in following structure Meaning is a kind of：
A kind of preparation of the luminous organic material of electroluminescent organic material with electric transmission effect of the present invention Method is as follows：
Wherein, R is selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused ring aryls, taken Generation or unsubstituted C7-C60 aralkyl, substituted or unsubstituted C7-C60 aryl amines, substituted or unsubstituted C7-C60 aryl oxides Base, substituted or unsubstituted C7-C60 aromatic sulfides base, substituted or unsubstituted C6-C60 aryl phosphines, substituted or unsubstituted C4- Any one in C60 aromatic heterocycle.
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 selection of the R is ibid It is described, it will not be repeated here.
The present invention also provides a kind of organic luminescent device of the electroluminescent organic material with electric transmission effect, described The organic luminescent device that organic luminescent device is well known to those skilled in the art.Organic luminescent device bag of the present invention The one or more organic compound layers for including first electrode, second electrode and being placed between two electrodes, at least one organic compound Nitride layer includes a kind of at least one organic light emission of the electroluminescent organic material with electric transmission effect of the present invention Material.The organic compound layer preferably includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electric transmission Containing of the present invention a kind of with electronics in layer and at least one layer in electron injecting layer, preferably described electron transfer layer The electroluminescent organic material of transmission effects.
Embodiment 1：The preparation of compound 1
Step1, to bromination Bian 100mmol is just added from the there-necked flask that air dry oven is taken out, anhydrous magnesium chloride 1.5 is worked as Amount, the equivalent of part bipyridyl 0.15, the equivalent of activated zinc powder 3.Under nitrogen protection, Ni (COD) is added20.1 equivalent, Zhi Houzai Under nitrogen protection, solvent acetonitrile, and acyl chlorides are added.12h is reacted at room temperature.After the completion of reaction, via column chromatography, product is obtained 41mmol(1-1)。
Step2,9.2g metallic sodiums are dissolved in 185ml absolute ethanols, and this solution is cooled into 0 DEG C, two are gradually added dropwise Benzyl ketone 42g, and diethy-aceto oxalate 30g.Reaction solution reacts 3h under zero degrees celsius, is gradually warming up to room temperature reaction 48h.Instead After the completion of answering, glacial acetic acid is gradually added dropwise neutral to reaction solution.Reaction solution crosses diatom soil hopper, removes a small amount of grease.It is added dropwise The 100ml 2N concentrated sulfuric acids, have bright yellow solid to produce.Filtering, filter cake is washed with water.Dry.Crude product recrystallizes three with dimethylbenzene It is secondary, then, obtain faint yellow acicular crystal, 37mmol (1-2) with ethyl alcohol recrystallization twice.
Step3,37mmol (1-2), and 80mmol malononitrile are dissolved in ethylene glycol, 3h is reacted at 100 DEG C, will be reacted Liquid is poured into water, and has solid Precipitation, filtering.Crude product is obtained, via column chromatography, product 30mmol compounds 1 are obtained.
Embodiment 2：The synthesis of compound 2
Step1, it is anhydrous to just addition 1- bromo- 4- (bromomethyl) the benzene 100mmol from the there-necked flask that air dry oven is taken out The equivalent of magnesium chloride 1.5, the equivalent of part bipyridyl 0.15, the equivalent of activated zinc powder 3.Under nitrogen protection, Ni (COD) is added2 0.1 Equivalent, adds solvent acetonitrile, and 2- (4- bromophenyls) chloroacetic chloride under nitrogen protection again afterwards.12h is reacted at room temperature.React Cheng Hou, via column chromatography, obtains product 41mmol (2-1).
Step2,9.2g metallic sodiums are dissolved in 185ml absolute ethanols, and this solution is cooled into 0 DEG C, 2-1 is gradually added dropwise 42g, and diethy-aceto oxalate 30g.Reaction solution reacts 3h under zero degrees celsius, is gradually warming up to room temperature reaction 48h.Reaction is completed Afterwards, glacial acetic acid is gradually added dropwise neutral to reaction solution.Reaction solution crosses diatom soil hopper, removes a small amount of grease.100ml is added dropwise The 2N concentrated sulfuric acids, have bright yellow solid to produce.Filtering, filter cake is washed with water.Dry.Crude product is recrystallized three times with dimethylbenzene, then is used Ethyl alcohol recrystallization twice, obtains faint yellow acicular crystal, 37mmol (2-2).
Step3,37mmol (2-2), and 80mmol malononitrile are dissolved in ethylene glycol, and .3h is reacted at 100 DEG C, will be anti- Answer liquid to be poured into water, there is solid Precipitation, filter.Crude product is obtained, via column chromatography, product 30mmol compounds 2-3 is obtained.
Step4, by compound 2-3 30mmol, adds 60mmol phenyl boric acid, 90mmol sodium carbonate, 0.3mmol Pd (PPh3)4, toluene, ethanol, water ratio are (4:1:1) mixed solvent, argon gas is replaced reacts 10h under three reflux temperatures, thick production Product obtain product 22mmol compounds 2 via column chromatography.
Embodiment 3：The synthesis of compound 6
Be the same as Example 2, the phenyl boric acid in step4 is replaced with to cyanophenylboronic acid.
Embodiment 4：The synthesis of compound 8
Be the same as Example 2,9,9- dimethyl fluorene -2- boric acid is replaced with by the phenyl boric acid in step4.
Embodiment 5：The synthesis of compound 10
Step1, it is anhydrous to just addition 1- bromo- 4- (bromomethyl) the benzene 100mmol from the there-necked flask that air dry oven is taken out The equivalent of magnesium chloride 1.5, the equivalent of part bipyridyl 0.15, the equivalent of activated zinc powder 3.Under nitrogen protection, Ni (COD) is added2 0.1 Equivalent, adds solvent acetonitrile, and 2- (4- bromophenyls) chloroacetic chloride under nitrogen protection again afterwards.12h is reacted at room temperature.React Cheng Hou, via column chromatography, obtains product 41mmol (2-1).
Step2,9.2g metallic sodiums are dissolved in 185ml absolute ethanols, and this solution is cooled into 0 DEG C, 2-1 is gradually added dropwise 42g, and diethy-aceto oxalate 30g.Reaction solution reacts 3h under zero degrees celsius, is gradually warming up to room temperature reaction 48h.Reaction is completed Afterwards, glacial acetic acid is gradually added dropwise neutral to reaction solution.Reaction solution crosses diatom soil hopper, removes a small amount of grease.100ml is added dropwise The 2N concentrated sulfuric acids, have bright yellow solid to produce.Filtering, filter cake is washed with water.Dry.Crude product is recrystallized three times with dimethylbenzene, then is used Ethyl alcohol recrystallization twice, obtains faint yellow acicular crystal, 37mmol (2-2).
Step3,37mmol (2-2), and 80mmol malononitrile are dissolved in ethylene glycol, 3h is reacted at 100 DEG C, will be reacted Liquid is poured into water, and has solid Precipitation, filtering.Crude product is obtained, via column chromatography, product 30mmol compounds 2-3 is obtained.
Step4, by 2-3 30mmol, adds 60mmol diphenylamines, 90mmol potassium tert-butoxides, 0.3mmol Pd2 (dba)3, toluene, argon gas displacement three times adds 0.6mmol tri-butyl phosphines, argon gas is replaced three times again, anti-under reflux temperature 10h is answered, post is crossed, obtains the 22mmol of product 10.
Embodiment 6：The synthesis of compound 21
Synthetic method be the same as Example 2.Phenyl boric acid in step4 is replaced with into pyridine -4- boric acid.
Embodiment 7：The synthesis of compound 23
Synthetic method be the same as Example 2.Phenyl boric acid in step4 is replaced with into pyridine -3- boric acid.
Embodiment 8：The synthesis of compound 29
Synthetic method be the same as Example 2.Phenyl boric acid in step4 is replaced with into dibenzofurans -2- boric acid.
Embodiment 9：The synthesis of compound 30
Synthetic method be the same as Example 2.Phenyl boric acid in step4 is replaced with into dibenzothiophenes -2- boric acid.
Embodiment 10：The synthesis of compound 32
Synthetic method be the same as Example 2.Phenyl boric acid in step4 is replaced with into 4- phenoxyphenyl boronic acids.
Embodiment 11：The synthesis of compound 33
Synthetic method be the same as Example 2.Phenyl boric acid in step4 is replaced with into 4- Phenylsulfanylphenyl boric acid.
A kind of FD-MS values for electroluminescent organic material with electric transmission effect that the embodiment of the present invention is prepared It is 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 BND/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 BND/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.Vacuum evaporation compound 1 is as electron transfer layer on luminescent layer, and 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 6.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 8.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 10.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 21.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 23.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 29.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 30.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 32.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 33.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 luminescent lifetime, 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 electroluminescent organic material with electric transmission effect of the present invention is in electroluminescent Applied in device, the minimum 3.9V of driving voltage, luminous efficiency reaches as high as 21.4cd/A, the larger device that improves Luminous 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 (5)

1. a kind of electroluminescent organic material with electric transmission effect, its general structure is shown in formula I：
Wherein, R be selected from hydrogen, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 fused ring aryls, substitution or Unsubstituted C7-C60 aralkyl, substituted or unsubstituted C7-C60 aryl amines, substituted or unsubstituted C7-C60 aryl ether groups, take Generation or unsubstituted C7-C60 aromatic sulfides base, substituted or unsubstituted C6-C60 aryl phosphines, substituted or unsubstituted C4-C60 Any one in aromatic heterocycle.
2. a kind of electroluminescent organic material with electric transmission effect according to claim 1, it is characterised in that R Selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring aryls, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C7-C30 aryl amines, substituted or unsubstituted C7-C30 aryl ether groups, substitution do not take The C7-C30 aromatic sulfides base in generation, substituted or unsubstituted C6-C30 aryl phosphines, substituted or unsubstituted C4-C30 aromatic series it is miscellaneous Any one in ring group.
3. a kind of electroluminescent organic material with electric transmission effect according to claim 1, it is characterised in that choosing From any one in following structure：
4. a kind of organic luminescent device of the electroluminescent organic material with electric transmission effect, including first electrode, second Electrode and the one or more organic compound layers being placed between two electrode, it is characterised in that at least one organic compound Nitride layer includes a kind of at least one organic electroluminescence with electric transmission effect as described in claims 1 to 3 any one Luminescent material.
5. a kind of organic illuminator of electroluminescent organic material with electric transmission effect according to claim 4 Part, it is characterised in 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.
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CN106008264A (en) * 2016-05-20 2016-10-12 中节能万润股份有限公司 Organic electroluminescent material, application and device thereof
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