CN107641102A - A kind of electroluminescent organic material and organic luminescent device - Google Patents
A kind of electroluminescent organic material and organic luminescent device Download PDFInfo
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- CN107641102A CN107641102A CN201711005754.6A CN201711005754A CN107641102A CN 107641102 A CN107641102 A CN 107641102A CN 201711005754 A CN201711005754 A CN 201711005754A CN 107641102 A CN107641102 A CN 107641102A
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Abstract
The present invention provides a kind of electroluminescent organic material and organic luminescent device, belongs to organic photoelectrical material technical field.Solves 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.The present invention is added in nitrogen heterocyclic ring structure similar to fluorenes ring structure, can be while cavity transmission ability be retained, improve triplet, test result indicates that, the organic luminescent device prepared using electroluminescent organic material of the present invention, luminous efficiency highest 23.5cd/A, and driving voltage is minimum can reach 4.2V, 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 electroluminescent organic material and organic light emission
Device.
Background technology
Electroluminescent organic material has been developed for quite a long time, and fluorescent material is 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.
In the organic luminescent device prepared using phosphor material, mostly using CBP etc. containing carbazole group material as
The main body luminescent material of luminescent layer.However, this kind of material as material of main part in use, device obtain driving voltage often compared with
It is high.Furthermore it has been found that luminous efficiency is roll-offed in high luminance area when such phosphor material is applied to during plane is shown
It is extremely serious.
The content of the invention
In order to solve in the prior art the skill of the luminescent properties such as organic photoelectrical material luminous efficiency is low, driving voltage is higher difference
Art problem, the present invention provide a kind of electroluminescent organic material and organic luminescent device.
Present invention firstly provides a kind of electroluminescent organic material, and its general structure is shown in formula I：
Wherein, X is selected from oxygen, sulphur, CH2Or C (CH3)2；
R be selected from substituted or unsubstituted C1-C20 aliphatic alkyl, substituted or unsubstituted C6-C60 aryl, substitution or
Unsubstituted C8-C60 fused ring aryls, substituted or unsubstituted C7-C60 aryl ether groups, substituted or unsubstituted C7-C60 aromatic sulfides
Base, substituted or unsubstituted C4-C60 aromatic heterocycle in one kind.
Preferably, R be selected from substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C6-C30 aryl, substitution or
Unsubstituted C8-C30 fused ring aryls, substituted or unsubstituted C7-C30 aryl ether groups, substituted or unsubstituted C7-C30 aromatic sulfides
Base, substituted or unsubstituted C4-C30 aromatic heterocycle in one kind.
Preferably, the electroluminescent organic material, selected from following any structure：
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 compound layers, at least one organic compound layer include at least one organic electroluminescent of the present invention
Material.
Beneficial effects of the present invention：
The present invention provides a kind of electroluminescent organic material and organic luminescent device, and the present invention increases in nitrogen heterocyclic ring structure
Add and be similar to fluorenes ring structure, triplet can be improved while cavity transmission ability is retained, test result indicates that,
The organic luminescent device prepared using electroluminescent organic material of the present invention, luminous efficiency highest 23.5cd/A, and drive
Dynamic voltage is minimum can reach 4.2V, is a kind of excellent OLED material.
Embodiment
It is clearly and completely described below in conjunction with the technical scheme of the embodiment of the present invention, it is clear that described implementation
Example only part of the embodiment of the present invention, rather than whole embodiments.It is common based on the embodiment in the present invention, this area
The every other embodiment that technical staff is obtained under the premise of creative work is not made, belong to the model that the present invention protects
Enclose.
Present invention firstly provides a kind of electroluminescent organic material, and its general structure is shown in formula I：
Wherein, X is selected from oxygen, sulphur, CH2Or C (CH3)2；
R be selected from substituted or unsubstituted C1-C20 aliphatic alkyl, substituted or unsubstituted C6-C60 aryl, substitution or
Unsubstituted C8-C60 fused ring aryls, substituted or unsubstituted C7-C60 aryl ether groups, substituted or unsubstituted C7-C60 aromatic sulfides
Base, substituted or unsubstituted C4-C60 aromatic heterocycle in one kind.
Preferably, R be selected from substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C6-C30 aryl, substitution or
Unsubstituted C8-C30 fused ring aryls, substituted or unsubstituted C7-C30 aryl ether groups, substituted or unsubstituted C7-C30 aromatic sulfides
Base, substituted or unsubstituted C4-C30 aromatic heterocycle in one kind.
Preferably, the electroluminescent organic material, selected from following any structure：
Some specific structure types of electroluminescent organic material of the present invention are enumerated above, but it is of the present invention
Electroluminescent organic material is not limited to these listed chemical constitutions, and based on every structure by Formulas I, R is as above limited
Fixed group should be all included.
Electroluminescent organic material of the present invention, it can be prepared by following route reaction：
Wherein, X is selected from oxygen, sulphur, CH2Or C (CH3)2；
R be selected from substituted or unsubstituted C1-C20 aliphatic alkyl, substituted or unsubstituted C6-C60 aryl, substitution or
Unsubstituted C8-C60 fused ring aryls, substituted or unsubstituted C7-C60 aryl ether groups, substituted or unsubstituted C7-C60 aromatic sulfides
Base, substituted or unsubstituted C4-C60 aromatic heterocycle in one kind.
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 be prepared using preparation method well-known to those skilled in the art.Wherein, the selection of the R is same as above
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 include first electrode, second electrode and are placed between two electrodes
One or more organic compound layers, at least one organic compound layer includes 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
At least one layer in transport layer, electron injecting layer.
Embodiment 1：1 synthesis of compound
Step1. 100mmol 1-1 are added in 0.1L concentrated nitric acids, mixture reacts 24h at 75 DEG C.Obtained brown
Solution is cooled to room temperature.5L frozen water is added, stirring, cake filtration, is washed with deionized, is dried.Obtained crude product passes through post
Chromatography obtains product 1-2 84mmol.Yield 84%
Step2. under nitrogen protection, 84mmol compound 1-2, after adding appropriate anhydrous THF dissolvings, -78 are cooled to
DEG C, the n-BuLi of 3 equivalents is added dropwise, insulation reaction 0.5 hour, fast drop trimethyl borate, is slowly warming up to room temperature, reacts
Overnight.After completion of the reaction, in entering in diluted hydrochloric acid aqueous solution, solid matter separates out filtering, crude product crosses silicagel column and obtains 1-3,
70mmol。
Step3. 70mmol compound 1-3 is taken, adds THF and methanol 5:1 mixed solvent, add 10% Pd/C
, nitrogen displacement three times, replace three times again by hydrogen.5h is reacted under hydrogen atmosphere.Obtain product 55mmol 1-4.
Step4. upper step product 55mmol 1-4 are dissolved in 10ml concentrated hydrochloric acid, ice-water bath is cooled to 0 DEG C.It is added dropwise
55mmol sodium nitrite in aqueous solution 8ml.Obtained solution continues to stir 30min under ice-water bath.Rapidly join 0 DEG C of tetrahydrochysene
Change pyrroles 30mmol in 1M K2CO3The aqueous solution.Obtained mixture continues to stir 30min, filtering, obtained filter cake ethanol weight
Crystallization.Obtain product 1-5,35mmol.
Step5. 1-5 35mmol boric acid, 35mmol 1-6 are dissolved in toluene, add absolute ethyl alcohol, water, 105mmol
Potassium carbonate, the triphenyl phosphorus palladiums of 0.35mmol tetra- are added, Ar gas is replaced three times, back flow reaction 6h.Crude product crosses silica gel after the completion of reaction
Post obtains 30mmol products 1-7.
Step6. at room temperature, by compound products 1-7 30mmol, it is dissolved in toluene, stirs lower dropwise addition 120mmol's
Trifluoroacetic acid.1h is stirred at 100 DEG C.Saturated sodium bicarbonate aqueous solution is added after cooling reaction is quenched, extracted with EA.Organic phase
Dry, concentrate, column chromatography obtains product 1-8 24mmol.Yield 81%.
Step7. step product 1-8 24mmol are taken, add solvent DMSO, potassium tert-butoxide 50mmol, 80 degrees Celsius of stirrings
1h.Iodomethane 50mmol is added dropwise, is warming up to 90 degrees Celsius of reactions overnight.Crude product crosses silicagel column and obtains the 18mmol of product 1.
Embodiment 2：3 synthesis of compound
Step1. 100mmol 3-1 are added in 0.1L concentrated nitric acids, mixture reacts 24h at 75 DEG C.Obtained brown
Solution is cooled to room temperature.5L frozen water is added, stirring, cake filtration, is washed with deionized, is dried.Obtained crude product passes through post
Chromatography obtains product 3-2 84mmol.Yield 84%
Step2. under nitrogen protection, 84mmol compound 3-2, after adding appropriate anhydrous THF dissolvings, -78 are cooled to
DEG C, the n-BuLi of 3 equivalents is added dropwise, insulation reaction 0.5 hour, fast drop trimethyl borate, is slowly warming up to room temperature, reacts
Overnight.After completion of the reaction, in entering in diluted hydrochloric acid aqueous solution, solid matter separates out filtering, crude product crosses silicagel column and obtains 3-3,
70mmol。
Step3. 70mmol compound 3-3 is taken, adds THF and methanol 5:1 mixed solvent, add 10% Pd/C
, nitrogen displacement three times, replace three times again by hydrogen.5h is reacted under hydrogen atmosphere.Obtain product 55mmol 3-4.
Step4. upper step product 55mmol 3-4 are dissolved in 10ml concentrated hydrochloric acid, ice-water bath is cooled to 0 DEG C.It is added dropwise
55mmol sodium nitrite in aqueous solution 8ml.Obtained solution continues to stir 30min under ice-water bath.Rapidly join 0 DEG C of tetrahydrochysene
Change pyrroles 30mmol in 1M K2CO3The aqueous solution.Obtained mixture continues to stir 30min, filtering, obtained filter cake ethanol weight
Crystallization.Obtain product 3-5,35mmol.
Step5. 3-5 35mmol boric acid, 35mmol 3-6 are dissolved in toluene, add absolute ethyl alcohol, water, 105mmol
Potassium carbonate, the triphenyl phosphorus palladiums of 0.35mmol tetra- are added, Ar gas is replaced three times, back flow reaction 6h.Crude product crosses silica gel after the completion of reaction
Post obtains 30mmol products 3-7.
Step6. at room temperature, by compound products 3-7 30mmol, it is dissolved in toluene, stirs lower dropwise addition 120mmol's
Trifluoroacetic acid.1h is stirred at 100 DEG C.Saturated sodium bicarbonate aqueous solution is added after cooling reaction is quenched, extracted with EA.Organic phase
Dry, concentrate, column chromatography obtains product 3-8 24mmol.Yield 81%.
Step7. step product 3-8 24mmol are taken, add solvent DMSO, potassium tert-butoxide 50mmol, 80 degrees Celsius of stirrings
1h.Iodomethane 50mmol is added dropwise, is warming up to 90 degrees Celsius of reactions overnight.Crude product crosses silicagel column and obtains the 18mmol of product 3.
Embodiment 3：9 synthesis of compound
Step1-Step6 is the same as embodiment 1.
Step7. step product 1-8 24mmol, 24mmol iodobenzenes is taken to be dissolved in toluene, 3 equivalent potassium hydroxide of addition,
0.1 equivalent CuI, the woods phenanthroline of 0.1 equivalent, argon gas is replaced three times, at 100 DEG C, reacts 6h.Reaction is completed, reaction solution mistake
Silica gel funnel, filtrate is washed with deionized, concentrated, crude product crosses silicagel column and obtains 18mmol products 9.
Embodiment 4：11 synthesis of compound
Step1-Step6 is the same as embodiment 2.
Step7. step product 2-8 24mmol, 24mmol iodobenzenes is taken to be dissolved in toluene, 3 equivalent potassium hydroxide of addition,
0.1 equivalent CuI, the woods phenanthroline of 0.1 equivalent, argon gas is replaced three times, at 100 DEG C, reacts 6h.Reaction is completed, reaction solution mistake
Silica gel funnel, filtrate is washed with deionized, concentrated, crude product crosses silicagel column and obtains 18mmol products 11.
Embodiment 5：21 synthesis of compound
Step1-Step6 is the same as embodiment 1.
Step7. take step product 1-8 24mmol, 24mmol 4- bromopyridines to be dissolved in toluene, add 3 equivalent hydrogen-oxygens
Change potassium, 0.1 equivalent CuI, the woods phenanthroline of 0.1 equivalent, argon gas is replaced three times, at 100 DEG C, reacts 6h.Reaction is completed, reaction
Liquid crosses silica gel funnel, and filtrate is washed with deionized, concentrated, crude product crosses silicagel column and obtains 18mmol products 21.
Embodiment 6：29 synthesis of compound
Step1-Step6 is the same as embodiment 1.
Step7. step product 1-8 24mmol are taken, 30mmolNaH is added, solvent DMF, stirs 0.5h at room temperature.Add
24mmol 2- chlorine pyrimidines, react 2h at room temperature.Deionized water is poured into after the completion of reaction, is filtered, filter cake successively with deionized water and
Ethanol washs.Column chromatography is crossed, obtains the 18mnmol of product 29.
Embodiment 7：37 synthesis of compound
Step1-Step6 is the same as embodiment 1.
Step7. take step product 1-8 24mmol, 24mmol 4- bromo biphenyl ethers to be dissolved in toluene, add 3 Equivalent Hydrogens
Potassium oxide, 0.1 equivalent CuI, the woods phenanthroline of 0.1 equivalent, argon gas is replaced three times, at 100 DEG C, reacts 6h.Reaction is completed, instead
Liquid is answered to cross silica gel funnel, filtrate is washed with deionized, concentrated, crude product crosses silicagel column and obtains 18mmol products 37.
Embodiment 8：53 synthesis of compound
Step1-Step6 is the same as embodiment 1.
Step7. take the bromo- 9- phenyl carbazoles of step product 1-8 24mmol, 24mmol 3- to be dissolved in toluene, add 3 and work as
Potassium hydroxide, 0.1 equivalent CuI, the woods phenanthroline of 0.1 equivalent are measured, argon gas is replaced three times, at 100 DEG C, reacts 6h.React
Into reaction solution crosses silica gel funnel, and filtrate is washed with deionized, concentrated, crude product crosses silicagel column and obtains 18mmol products 53.
Embodiment 9：61 synthesis of compound
Step1-Step6 is the same as embodiment 1.
Step7. step product 1-8 24mmol, the bromo- N of 24mmol 4- are taken, N- diphenylamines is dissolved in toluene, is added 3 and is worked as
Potassium hydroxide, 0.1 equivalent CuI, the woods phenanthroline of 0.1 equivalent are measured, argon gas is replaced three times, at 100 DEG C, reacts 6h.React
Into reaction solution crosses silica gel funnel, and filtrate is washed with deionized, concentrated, crude product crosses silicagel column and obtains 18mmol products 61.
Embodiment 10：65 synthesis of compound
Step1-Step6 is the same as embodiment 1.
Step7. step product 1-8 24mmol, 24mmol 9- (4- bromophenyls) -9H- carbazoles is taken to be dissolved in toluene, add
Enter 3 equivalent potassium hydroxide, 0.1 equivalent CuI, the woods phenanthroline of 0.1 equivalent, argon gas is replaced three times, at 100 DEG C, reacts 6h.Instead
It should complete, reaction solution crosses silica gel funnel, and filtrate is washed with deionized, concentrated, crude product crosses silicagel column and obtains 18mmol products 65.
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
| Embodiment | Compound | FD-MS |
| 1 | 1 | M/z:325.07, C24H23N (325.18) |
| 2 | 3 | M/z:327.53, C23H21NO (327.16) |
| 3 | 9 | M/z:387.64, C29H25N (387.20) |
| 4 | 11 | M/z:389.20, C28H23NO (389.18) |
| 5 | 21 | M/z:388.09, C28H24N2 (388.19) |
| 6 | 29 | M/z:389.13, C27H23N3 (389.19) |
| 7 | 37 | M/z:479.83, C35H29NO (479.22) |
| 8 | 53 | M/z:552.34, C41H32N2 (552.26) |
| 9 | 61 | M/z:554.50, C41H34N2 (554.27) |
| 10 | 65 | M/z:552.33, C41H32N2 (552.26) |
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 NPB is stated in anode grid substrate as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 70nm.In hole
Vacuum evaporation CBP/Ir (ppy) in transport layer3As luminescent layer, doping concentration 10wt%, evaporation rate 0.005nm/s,
Evaporation thickness is 30nm.Vacuum evaporation BPhen is as electron transfer layer, evaporation rate 0.01nm/s, evaporation on luminescent layer
Thickness is 50nm.Vacuum evaporation Al/LiF layers are as negative electrode, thickness 200nm on the electron transport layer.
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 NPB is stated in anode grid substrate as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 70nm.In hole
Vacuum evaporation compound 1/Ir (ppy) in transport layer3It is as luminescent layer, doping concentration 10wt%, evaporation rate
0.005nm/s, evaporation thickness 30nm.Vacuum evaporation BPhen is as electron transfer layer, evaporation rate on luminescent layer
0.01nm/s, evaporation thickness 50nm.Vacuum evaporation Al/LiF layers are as negative electrode, thickness 200nm on the electron transport layer.
Application example 2：
Change the compound 1 in Application Example 1 into compound 3.The luminescent properties of the device are measured, the results are shown in Table 2.
Application example 3：
Change the compound 1 in Application Example 1 into compound 9.The luminescent properties of the device are measured, the results are shown in Table 2.
Application example 4：
Change the compound 1 in Application Example 1 into compound 11.The luminescent properties of the device are measured, the results are shown in Table 2.
Application example 5：
Change the compound 1 in Application Example 1 into compound 21.The luminescent properties of the device are measured, the results are shown in Table 2.
Application example 6：
Change the compound 1 in Application Example 1 into compound 29.The luminescent properties of the device are measured, the results are shown in Table 2.
Application example 7：
Change the compound 1 in Application Example 1 into compound 37.The luminescent properties of the device are measured, the results are shown in Table 2.
Application example 8：
Change the compound 1 in Application Example 1 into compound 53.The luminescent properties of the device are measured, the results are shown in Table 2.
Application example 9：
Change the compound 1 in Application Example 1 into compound 61.The luminescent properties of the device are measured, the results are shown in Table 2.
Application example 10：
Change the compound 1 in Application Example 1 into compound 65.The luminescent properties of the device are measured, the results are shown in Table 2.
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 (4)
1. a kind of electroluminescent organic material, its general structure is shown in formula I：
Wherein, X is selected from oxygen, sulphur, CH2Or C (CH3)2；
Aliphatic alkyls of the R selected from substituted or unsubstituted C1-C20, substituted or unsubstituted C6-C60 aryl, substitution do not take
The C8-C60 fused ring aryls in generation, substituted or unsubstituted C7-C60 aryl ether groups, substituted or unsubstituted C7-C60 aromatic sulfides base, take
One kind in generation or unsubstituted C4-C60 aromatic heterocycle.
2. a kind of electroluminescent organic material according to claim 1, it is characterised in that R is selected from substituted or unsubstituted
C1-C5 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C8-C30 fused ring aryls, substitution do not take
The C7-C30 aryl ether groups in generation, substituted or unsubstituted C7-C30 aromatic sulfides base, substituted or unsubstituted C4-C30 aromatic series are miscellaneous
One kind in ring group.
3. a kind of electroluminescent organic material according to claim 1, it is characterised in that any in following structure
It is a kind of：
4. a kind of organic luminescent device, including first electrode, second electrode and the one or more being placed between two electrode
Organic compound layer, it is characterised in that at least one organic compound layer includes at least one such as institute in claim 1,2 or 3
The electroluminescent organic material stated.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109879807A (en) * | 2019-04-22 | 2019-06-14 | 吉林奥来德光电材料股份有限公司 | Miscellaneous anthracene class organic compound and its preparation method and application |
-
2017
- 2017-10-25 CN CN201711005754.6A patent/CN107641102A/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109879807A (en) * | 2019-04-22 | 2019-06-14 | 吉林奥来德光电材料股份有限公司 | Miscellaneous anthracene class organic compound and its preparation method and application |
| CN109879807B (en) * | 2019-04-22 | 2020-09-29 | 吉林奥来德光电材料股份有限公司 | Organic compounds of heteroanthracene class, preparation method and application |
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