CN107090003A - The phosphor material and organic luminescent device of parent nucleus containing hetero atom and fluorenes ring structure - Google Patents

The phosphor material and organic luminescent device of parent nucleus containing hetero atom and fluorenes ring structure Download PDF

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CN107090003A
CN107090003A CN201710332101.2A CN201710332101A CN107090003A CN 107090003 A CN107090003 A CN 107090003A CN 201710332101 A CN201710332101 A CN 201710332101A CN 107090003 A CN107090003 A CN 107090003A
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compound
application example
hetero atom
ring structure
phosphor 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 parent nucleus containing hetero atom and the phosphor material and organic luminescent device of fluorenes ring structure, 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 high difference.Test result indicates that, the organic luminescent device prepared using parent nucleus containing hetero atom of the present invention and the phosphor material of fluorenes ring structure, luminous efficiency reaches as high as 18.8cd/A, driving voltage 3.2V, is a kind of excellent OLED material.

Description

The phosphor material and organic luminescent device of parent nucleus containing hetero atom and fluorenes ring structure
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to parent nucleus containing hetero atom and the phosphorescence material of fluorenes ring structure Material and organic 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 OLED research, the selection of organic material plays conclusive effect.Sandwich type OLED is according to work( Can classify can be divided into hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer etc., and luminescent layer Main material is called material of main part.The compound of the structure containing fluorenes ring is the important material of main part of a class, because there is rigidity to tie for it Structure, therefore the glass transition temperature and heat endurance of material are higher.But, the change of these presently disclosed structures containing fluorenes ring Compound is also less desirable as the luminescent properties of material of main part, it is impossible to meet OLED use requirement.
The content of the invention
In view of this, it is an object of the invention to provide the phosphor material of a kind of parent nucleus containing hetero atom and fluorenes ring structure and have Machine luminescent device.The organic luminescent device prepared using present invention parent nucleus containing hetero atom and the phosphor material of fluorenes ring structure, is had Higher luminous efficiency, lower driving voltage.
Present invention firstly provides a kind of parent nucleus containing hetero atom and the phosphor material of fluorenes ring structure, its general structure such as Formulas I It is shown：
Wherein, R be selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aromatic hydrocarbyls, Any one in substituted or unsubstituted C6-C30 aromatic ethers, substituted or unsubstituted C4-C30 heteroaromatics；
X is selected from oxygen, sulphur, SO2、NPh、C(CH3)2Or CPh2。
It is preferred that, the phosphor material of the parent nucleus containing hetero atom and fluorenes ring structure, any one in following structure：
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 phosphorescence material of the present invention Material.
Beneficial effects of the present invention：
The present invention provides a kind of parent nucleus containing hetero atom and the phosphor material and organic luminescent device of fluorenes ring structure, experimental result Show, the organic luminescent device prepared using parent nucleus containing hetero atom of the present invention and the phosphor material of fluorenes ring structure, light effect Rate reaches as high as 21.8cd/A, and driving voltage is minimum can reach 3.2V, 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.Embodiment in the present invention, ordinary skill The every other embodiment that personnel are obtained under the premise of creative work is not made, belongs to the scope of protection of the invention.
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 parent nucleus containing hetero atom and the phosphor material of fluorenes ring structure, its general structure such as Formulas I institute Show：
Wherein, R be selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aromatic hydrocarbyls, Any one in substituted or unsubstituted C6-C30 aromatic ethers, substituted or unsubstituted C4-C30 heteroaromatics；
X is selected from oxygen, sulphur, SO2、NPh、C(CH3)2Or CPh2。
According to the present invention, the substituted alkyl, the aromatic hydrocarbyl of substitution, the aromatic ether of substitution, the fragrance of substitution In race's heterocycle, the substituent may be selected from C1~C4 alkyl, C6-C18 aryl, C6-C18 aryl amines or C4-C18 heterocyclic radicals, institute The number for stating substituent can be 1~5, preferably 1~3.Hetero atom in heterocycle of the present invention is preferably O, S or N.
As an example, it is not particularly limited, the phosphor material of parent nucleus containing hetero atom of the present invention and fluorenes ring structure, preferably Any one in following structure：
It is enumerated above some specific structures of parent nucleus containing hetero atom of the present invention and the phosphor material of fluorenes ring structure Form, but the phosphor material of parent nucleus containing hetero atom of the present invention and fluorenes ring structure is not limited to these listed chemistry knots Structure, it is every based on Formulas I or II structures, R be group as defined above should all be included.
The phosphor material of parent nucleus containing hetero atom of the present invention and fluorenes ring structure, can be prepared into by following route reaction Arrive：
Wherein, R be selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aromatic hydrocarbyls, Any one in substituted or unsubstituted C6-C30 aromatic ethers, substituted or unsubstituted C4-C30 heteroaromatics；
X is selected from oxygen, sulphur, SO2、NPh、C(CH3)2Or CPh2。
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, 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 phosphorescence material of the present invention Material.The organic compound layer preferably includes hole injection layer, hole transmission layer, luminescent layer, hole blocking layer, electron transfer layer With at least one layer in electron injecting layer.
Embodiment 1：1 synthesis of compound
Step1. 39g benzene, 66.8g aluminium chloride are added in 500ml there-necked flasks, 206.3g phosphorus chloride is reacted at 65 DEG C 6h, vacuum distillation goes out excessive phosphorus chloride, and the POCl3 of 5 equivalents is added drop-wise in aforesaid liquid, and control temperature is no more than 50 DEG C, 70 DEG C of reaction 4h use petroleum ether extraction reactant several times, and normal pressure steams petroleum ether, then phenyldichlorophosphine is collected in vacuum distillation.
Step2. 72mmol phenyldichlorophosphines are dissolved in anhydrous THF, cool to -78 degrees Celsius, 2.5 equivalents are slowly added dropwise N-BuLi, reacts 2h, adds the THF solution of the 3- bromine dibenzofurans of 2 equivalents.It is to slowly warm up to react at room temperature 3h again.Instead After the completion of answering, a large amount of water are added, there is white products precipitation, filtered, filter cake crosses silicagel column and obtains 61mmol products 1-2.
Step3. 61mmol 1-2 are dissolved in DCM, add 2.5 equivalent m-CPBA, 2h is reacted at room temperature, reaction is completed Afterwards, solution is washed with the aqueous solution of sodium bisulfite of saturation, is dried, and concentration, product crosses silicagel column and obtains 44mmol 1.
Embodiment 2：Compound it is 2-in-1 into
Be the same as Example 1.3- bromine dibenzofurans in Step2. is replaced with into 3- bromine dibenzothiophenes.
Embodiment 3：3 synthesis of compound
Step1. 39g benzene, 66.8g aluminium chloride are added in 500ml there-necked flasks, 206.3g phosphorus chloride is reacted at 65 DEG C 6h, vacuum distillation goes out excessive phosphorus chloride, and the POCl3 of 5 equivalents is added drop-wise in aforesaid liquid, and control temperature is no more than 50 DEG C, 70 DEG C of reaction 4h use petroleum ether extraction reactant several times, and normal pressure steams petroleum ether, then phenyldichlorophosphine is collected in vacuum distillation.
Step2. 100mmol 3- bromine dibenzothiophenes is dissolved in DCM, adds 2.5 equivalent m-CPBA, at room temperature instead 2h is answered, after the completion of reaction, solution is washed with the aqueous solution of sodium bisulfite of saturation, dried, concentration, product is crossed silicagel column and obtained 85mmol 3-1。
Step3. 72mmol phenyldichlorophosphines are dissolved in anhydrous THF, cool to -78 degrees Celsius, 2.5 equivalents are slowly added dropwise N-BuLi, reacts 2h, adds the 3-1 of 2 equivalents THF solution.It is to slowly warm up to react at room temperature 3h again.After the completion of reaction, plus Enter a large amount of water, there is white products precipitation, filter, filter cake crosses silicagel column and obtains 61mmol products 3-2.
Step4. 61mmol 3-2 are dissolved in DCM, add 2.5 equivalent m-CPBA, 2h is reacted at room temperature, reaction is completed Afterwards, solution is washed with the aqueous solution of sodium bisulfite of saturation, is dried, and concentration, product crosses silicagel column and obtains 45mmol 3.
Embodiment 4：4 synthesis of compound
Be the same as Example 1.3- bromine dibenzofurans in Step2. is replaced with into the bromo- 9- phenyl -9H- carbazoles of 2-.
Embodiment 5：5 synthesis of compound
Be the same as Example 1.3- bromine dibenzofurans in Step2. is replaced with into the bromo- 9,9- dimethyl -9H- fluorenes of 2-.
Embodiment 6：6 synthesis of compound
Be the same as Example 1.3- bromine dibenzofurans in Step2. is replaced with into the bromo- 9,9- diphenyl -9H- fluorenes of 2-.
Embodiment 7：7 synthesis of compound
Be the same as Example 1.3- bromine dibenzofurans in Step2. is replaced with into 4- bromine dibenzofurans.
Embodiment 8：8 synthesis of compound
Be the same as Example 2.3- bromine dibenzothiophenes in Step2. is replaced with into 4- bromine dibenzothiophenes.
Embodiment 9：9 synthesis of compound
Be the same as Example 3.3-1 in Step2. is replaced with
Embodiment 10：10 synthesis of compound
Be the same as Example 4.The bromo- 9- phenyl -9H- carbazoles of 2- in Step2. are replaced with into the bromo- 9- phenyl -9H- carbazoles of 1-.
Embodiment 11：11 synthesis of compound
Be the same as Example 5.The bromo- 9,9- dimethyl -9H- fluorenes of 2- in Step2. is replaced with into the bromo- 9,9- dimethyl -9H- of 1- Fluorenes.
Embodiment 12：12 synthesis of compound
Be the same as Example 6.By the bromo- 9,9- benzhydryls -9H- fluorenes of 2- in Step2. replace with the bromo- 9,9- diphenyl of 1- - 9H- fluorenes.
Embodiment 13：13 synthesis of compound
Be the same as Example 1.3- bromine dibenzofurans in Step2. is replaced with into 2- bromine dibenzofurans.
Embodiment 14：14 synthesis of compound
Be the same as Example 2.3- bromine dibenzothiophenes in Step2. is replaced with into 2- bromine dibenzothiophenes.
Embodiment 15：15 synthesis of compound
Be the same as Example 3.3-1 in Step2. is replaced with
Embodiment 16：16 synthesis of compound
Be the same as Example 4.The bromo- 9- phenyl -9H- carbazoles of 2- in Step2. are replaced with into the bromo- 9- phenyl -9H- carbazoles of 3-.
Embodiment 17：17 synthesis of compound
Step1. 39g benzene, 66.8g aluminium chloride are added in 500ml there-necked flasks, 206.3g phosphorus chloride is reacted at 65 DEG C 6h, vacuum distillation goes out excessive phosphorus chloride, and the POCl3 of 5 equivalents is added drop-wise in aforesaid liquid, and control temperature is no more than 50 DEG C, 70 DEG C of reaction 4h use petroleum ether extraction reactant several times, and normal pressure steams petroleum ether, then phenyldichlorophosphine is collected in vacuum distillation.
Step2. 3g Raney's nickels are added into 49ml (1000mmol) of hydrazine hydrates, 64g (250mmol) of 3- bromines are added Fluorenone, 1000ml toluene and 2000ml ethanol, quick stirring, back flow reaction 2 hours, solvent is spin-dried for after the completion of reaction, is obtained Crude product cross silicagel column, obtain product 17-0,37g.
Step3. 37g (152mmol) of 17-0 are dissolved in 600ml DMSO, at room temperature, add 43.9g (457mmol) potassium tert-butoxide, is warming up to 80 DEG C.64.8g (457mmol) iodomethane is added dropwise, control temperature is no more than 90 DEG C. 80-90 DEG C of reaction 30min, adds 1000ml water, and stirring, the solid of precipitation is washed with water and methanol.Obtain product 17-1 30g.
Step4. 72mmol phenyldichlorophosphines are dissolved in anhydrous THF, cool to -78 degrees Celsius, 2.5 equivalents are slowly added dropwise N-BuLi, reacts 2h, adds the 17-1 of 2 equivalents THF solution.It is to slowly warm up to react at room temperature 3h again.After the completion of reaction, plus Enter a large amount of water, there is white products precipitation, filter, filter cake crosses silicagel column and obtains 61mmol products 17-2.
Step5. 61mmol 17-2 are dissolved in DCM, add 2.5 equivalent m-CPBA, 2h is reacted at room temperature, has been reacted Cheng Hou, solution is washed with the aqueous solution of sodium bisulfite of saturation, is dried, and concentration, product crosses silicagel column and obtains 45mmol 17.
Embodiment 18：18 synthesis of compound
Step1. 39g benzene, 66.8g aluminium chloride are added in 500ml there-necked flasks, 206.3g phosphorus chloride is reacted at 65 DEG C 6h, vacuum distillation goes out excessive phosphorus chloride, and the POCl3 of 5 equivalents is added drop-wise in aforesaid liquid, and control temperature is no more than 50 DEG C, 70 DEG C of reaction 4h use petroleum ether extraction reactant several times, and normal pressure steams petroleum ether, then phenyldichlorophosphine is collected in vacuum distillation.
Step2. 3g Raney's nickels are added into 49ml (1000mmol) of hydrazine hydrates, 64g (250mmol) of 3- bromines are added Fluorenone, 1000ml toluene and 2000ml ethanol, quick stirring, back flow reaction 2 hours, solvent is spin-dried for after the completion of reaction, is obtained Crude product cross silicagel column, obtain product 17-0,37g.
Step3. 37g (152mmol) of 17-0 are dissolved in 600ml DMSO, at -78 DEG C, add 43.9g (457mmol) potassium tert-butoxide, is added dropwise 457mmol phenyl lithiums, is slowly warming up to room temperature.30min is reacted at room temperature, is added 1000ml water, stirring, the solid of precipitation is washed with water and methanol.Obtain product 18-1 30g.
Step4. 72mmol phenyldichlorophosphines are dissolved in anhydrous THF, cool to -78 degrees Celsius, 2.5 equivalents are slowly added dropwise N-BuLi, reacts 2h, adds the 18-1 of 2 equivalents THF solution.It is to slowly warm up to react at room temperature 3h again.After the completion of reaction, plus Enter a large amount of water, there is white products precipitation, filter, filter cake crosses silicagel column and obtains 61mmol products 18-2.
Step5. 61mmol 18-2 are dissolved in DCM, add 2.5 equivalent m-CPBA, 2h is reacted at room temperature, has been reacted Cheng Hou, solution is washed with the aqueous solution of sodium bisulfite of saturation, is dried, and concentration, product crosses silicagel column and obtains 45mmol 18.
Embodiment 19：19 synthesis of compound
Be the same as Example 5.The bromo- 9,9- dimethyl -9H- fluorenes of 2- in Step2. is replaced with into the bromo- 9,9- dimethyl -9H- of 4- Fluorenes.
Embodiment 20：20 synthesis of compound
Be the same as Example 6.The bromo- 9,9- dimethyl -9H- fluorenes of 2- in Step2. is replaced with into the bromo- 9,9- diphenyl -9H- of 4- Fluorenes.
Embodiment 21：67 synthesis of compound
Step1. 67-one is dissolved in anhydrous THF, cools to -78 DEG C, 2 eq. n-BuLis are added dropwise, in this temperature Lower reaction 0.5 hour, is gradually warming up to room temperature, prepares Li reagents stand-by.
Under argon gas protection, phosphorus trichloride and absolute ether are added in there-necked flask, the lower above-mentioned Li reagents of dropwise addition of stirring are raw Into white solid mixture.Back flow reaction 2h.Solvent is evaporated, product 67-two is obtained.
Step2~step3 be the same as Examples 1.
Embodiment 22：68 synthesis of compound
Be the same as Example 21.3- bromine dibenzofurans in Step2. is replaced with into 3- bromine dibenzothiophenes
Embodiment 23：69 synthesis of compound
Be the same as Example 21.3- bromine dibenzofurans in Step2. is replaced with
Embodiment 24：70 synthesis of compound
Be the same as Example 21.3- bromine dibenzofurans in Step2. is replaced with into the bromo- 9- phenyl -9H- carbazoles of 1-.
Embodiment 25：71 synthesis of compound
Be the same as Example 21.3- bromine dibenzofurans in Step2. is replaced with into the bromo- 9,9- dimethyl -9H- fluorenes of 1-.
Embodiment 26：72 synthesis of compound
Be the same as Example 21.3- bromine dibenzofurans in Step2. is replaced with into the bromo- 9,9- diphenyl -9H- fluorenes of 1-.
Embodiment 27：77 synthesis of compound
Step1. 77-one is dissolved in anhydrous THF, cools to -78 DEG C, 2 eq. n-BuLis are added dropwise, in this temperature Lower reaction 0.5 hour, is gradually warming up to room temperature, prepares Li reagents stand-by.
Under argon gas protection, phosphorus trichloride and absolute ether are added in there-necked flask, the lower above-mentioned Li reagents of dropwise addition of stirring are raw Into white solid mixture.Back flow reaction 2h.Solvent is evaporated, product 77-two is obtained.
Step2~step3 be the same as Examples 1.
Embodiment 28：78 synthesis of compound
Be the same as Example 27.3- bromine dibenzofurans in Step2. is replaced with into 3- bromine dibenzothiophenes
Embodiment 29：79 synthesis of compound
Be the same as Example 27.3- bromine dibenzofurans in Step2. is replaced with
Embodiment 30：80 synthesis of compound
Be the same as Example 27.3- bromine dibenzofurans in Step2. is replaced with into the bromo- 9- phenyl -9H- carbazoles of 2-.
Embodiment 31：81 synthesis of compound
Be the same as Example 27.3- bromine dibenzofurans in Step2. is replaced with into the bromo- 9,9- dimethyl -9H- fluorenes of 2-.
Embodiment 32：82 synthesis of compound
Be the same as Example 27.3- bromine dibenzofurans in Step2. is replaced with into the bromo- 9,9- diphenyl -9H- fluorenes of 2-.
The parent nucleus containing hetero atom and the FD-MS values of the phosphor material of fluorenes ring structure that the embodiment of the present invention is prepared are shown in Table 1 It is shown.
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 Vacuum evaporation hole injection layer HA-TCN in anode grid substrate is stated, evaporation rate is 0.1nm/s, be depositedHole transmission layer NPB, evaporation rate is 0.1nm/s, and evaporation thickness is 40nm；Vacuum evaporation CBP and doping GD1 are used as luminescent layer, doping concentration For 10wt%, evaporation rate is 0.1nm/s, and evaporation thickness is 30nm；Vacuum evaporation hole blocking layer and electronics on luminescent layer Transport layer TPBi, evaporation rate is 0.1nm/s, and evaporation thickness is 30nm；Al layers of vacuum evaporation is as negative electrode, and evaporation rate is 0.3~0.7nm/s, thickness is that (LiF, evaporation rate is 600nmThickness is)。
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 Vacuum evaporation hole injection layer HA-TCN in anode grid substrate is stated, evaporation rate is 0.1nm/s, be depositedHole transmission layer NPB, evaporation rate is 0.1nm/s, and evaporation thickness is 40nm；Vacuum evaporation CBP is used as hair with compound in doping application example 1 Photosphere, doping concentration is 10wt%, and evaporation rate is 0.1nm/s, and evaporation thickness is 30nm；The vacuum evaporation hole on luminescent layer Barrier layer and electron transfer layer TPBi, evaporation rate are 0.1nm/s, and evaporation thickness is 30nm；Al layers of vacuum evaporation as negative electrode, Evaporation rate is 0.3~0.7nm/s, and thickness is that (LiF, evaporation rate is 600nmThickness is)。
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 9.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 10.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 11.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 12.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 13.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 14.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 15.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 16.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 17.The luminescent properties of the device are measured, 2 are 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, 2 are 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, 2 are 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, 2 are the results are shown in Table.
Application example 21：
Change the compound 1 in Application Example 1 into compound 67.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 22：
Change the compound 1 in Application Example 1 into compound 68.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 23：
Change the compound 1 in Application Example 1 into compound 69.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 24：
Change the compound 1 in Application Example 1 into compound 70.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 25：
Change the compound 1 in Application Example 1 into compound 71.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 26：
Change the compound 1 in Application Example 1 into compound 72.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 27：
Change the compound 1 in Application Example 1 into compound 77.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 28：
Change the compound 1 in Application Example 1 into compound 78.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 29：
Change the compound 1 in Application Example 1 into compound 79.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 30：
Change the compound 1 in Application Example 1 into compound 80.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 31：
Change the compound 1 in Application Example 1 into compound 81.The luminescent properties of the device are measured, 2 are the results are shown in Table.
Application example 32：
Change the compound 1 in Application Example 1 into compound 82.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 to evaluate driving voltage, luminous efficiency using Keithley SMU235, PR650, as a result It is listed in Table 2 below：
The characteristics of luminescence of luminescent device prepared by the embodiment of the present invention of table 2
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 (3)

1. the phosphor material of parent nucleus containing hetero atom and fluorenes ring structure, its general structure is as shown in I：
Wherein, R is selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aromatic hydrocarbyls, substitution Or any one in unsubstituted C6-C30 aromatic ethers, substituted or unsubstituted C4-C30 heteroaromatics；
X is selected from oxygen, sulphur, SO2、NPh、C(CH3)2Or CPh2。
2. the phosphor material of parent nucleus containing hetero atom according to claim 1 and fluorenes ring structure, it is characterised in that selected from as follows Any one in structure：
3. 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 described in claim 1 or 2 Phosphor material.
CN201710332101.2A 2017-05-12 2017-05-12 The phosphor material and organic luminescent device of parent nucleus containing hetero atom and fluorenes ring structure Pending CN107090003A (en)

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