CN107915734A - A kind of naphtho- imdazole derivatives and its synthetic method and organic electroluminescence device - Google Patents

A kind of naphtho- imdazole derivatives and its synthetic method and organic electroluminescence device Download PDF

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CN107915734A
CN107915734A CN201711123502.3A CN201711123502A CN107915734A CN 107915734 A CN107915734 A CN 107915734A CN 201711123502 A CN201711123502 A CN 201711123502A CN 107915734 A CN107915734 A CN 107915734A
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unsubstituted
naphtho
substituted
imdazole derivatives
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蔡辉
张弘
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of naphtho- imdazole derivatives and its synthetic method and organic electroluminescence device, belongs to organic photoelectrical material technical field.Naphtho- imdazole derivatives provided by the present invention have structure shown in formula (I),

Description

A kind of naphtho- imdazole derivatives and its synthetic method and organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of naphtho- imdazole derivatives and its synthetic method And organic electroluminescence device.
Background technology
With the progress of information industry, traditional display has been unable to meet the requirement of people, such as：Cathode-ray tube (cathode ray tube, CRT) display volume is big, driving voltage is high；Liquid crystal display (liquid crystal Display, LCD) brightness is low, narrow viewing angle, operating temperature range are small；Plasma display (plasma display panel, PDP) involve great expense, resolution ratio is not high, power consumption is big.
Organic electroluminescent LED (organic light-emitting diodes, OLEDs) is as a kind of brand-new Display Technique possesses the unmatched advantage of existing Display Technique in each performance, such as have it is all solid state, from main light emission, brightness Height, high-resolution, visual angle wide (more than 170 degree), fast response time, thickness is thin, it is small, light-weight, can be used flexible base board, Low-voltage direct-current drives (3-10V), low in energy consumption, operating temperature range is wide etc. so that its application market is quite varied, such as illuminates System, communication system, car-mounted display, portable electric appts, fine definition show even military field.
Interior in recent years constantly realize of electroluminescent organic material is broken through, and the progress to attract people's attention is achieved, to traditional Display material constitutes strong challenge.After flexible OLED commercialization, associated scientific research and business in the world at present Strength is all in the work for the development this respect done one's utmost.Although electroluminescent organic material research have been achieved with it is huge into Fruit, but OLED also has some urgent problems to be solved during commercialized.
Electron transport material shows as short of electricity subsystem on molecular structure, has stronger electron acceptability, electronics Transmission material should also have preferable reversible reduction process.Common electron transport material mainly includes four cyano benzoquinones bismethane (TCNQ), trinitrofluorenone (TNF), (8-hydroxyquinoline) aluminium (Alq3), diazole (Oxadiazole), triazole (Triazole), naphthalene anhydride, flower acid anhydride, C60 and its derivative etc..
But presently disclosed electron transport material all has much room for improvement in efficiency and service life, so the electricity of exploitation stability and high efficiency Sub- transmission material, improves device efficiency, extends device lifetime, has critically important actual application value.
The content of the invention
The object of the present invention is to provide a kind of naphtho- imdazole derivatives and its synthetic method and organic electroluminescence device, sheet It is good to invent the derivative stability provided, glass transition temperature is high, and electron mobility is high, and good film-forming property, synthetic method is simply easily grasped Make, there is the organic electroluminescence device prepared using the derivative good luminous efficiency and service life to show.
Present invention firstly provides a kind of naphtho- imdazole derivatives, structural formula is：
Wherein, R1、R2、R3Independently selected from hydrogen, cyano group, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted The aryl of C6-C60, substituted or unsubstituted C3~C60 heterocyclic radical in one kind.
Preferably, the R1、R2、R3Independently selected from hydrogen, cyano group, substituted or unsubstituted C1-C30 alkyl, substitution or The aryl of unsubstituted C6-C30, substituted or unsubstituted C3~C30 heterocyclic radical in one kind.
Preferably, the R1、R2、R3Independently selected from hydrogen, cyano group, C1-C4 alkyl or substituted or unsubstituted following base Group：Phenyl, naphthyl, anthryl, phenanthryl, fluorenyl, two fluorenyl of spiral shell, carbazyl, dibenzothiophene, dibenzofuran group, triazine radical, Triphenylene, pyrenyl, quinolyl, isoquinolyl or pyridine radicals.
Preferably, any one of the naphtho- imdazole derivatives in structure as shown below：
The present invention also provides a kind of preparation method of naphtho- imdazole derivatives, syntheti c route are as follows：
Wherein, R1、R2、R3Independently selected from hydrogen, cyano group, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted The aryl of C6-C60, substituted or unsubstituted C3~C60 heterocyclic radical in one kind.
The present invention also provides a kind of organic electroluminescence device, including anode, cathode, it is placed in the anode and the cathode Between organic matter layer；The organic matter layer contains the naphtho- imdazole derivatives.
Preferably, electron transfer layer is contained in the organic matter layer, contains the naphtho- miaow in the electron transfer layer Zole derivatives.
Beneficial effects of the present invention:
Present invention firstly provides a kind of naphtho- imdazole derivatives, which has structure shown in formula (I), due to imidazole radicals The presence of group, material have excellent electron transport ability, and electron mobility is high；Big conjugated system so that stability of material Good, glass transition temperature is high；Good film-forming property, can prevent the effect of crystallization；Synthetic method is simple to operation, uses the derivative system There is standby organic electroluminescence device good luminous efficiency and service life to show.
Embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, still It should be appreciated that these descriptions are simply further explanation the features and advantages of the present invention, rather than to the claims in the present invention Limitation.
Present invention firstly provides a kind of naphtho- imdazole derivatives, structural formula is：
Wherein, R1、R2、R3Independently selected from hydrogen, cyano group, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted The aryl of C6-C60, substituted or unsubstituted C3~C60 heterocyclic radical in one kind.
Preferably, R1、R2、R3Independently selected from hydrogen, cyano group, substituted or unsubstituted C1-C30 alkyl, substitution or unsubstituted The aryl of C6-C30, one kind in the heterocyclic radical of substituted or unsubstituted C3~C30.
Preferably, R1、R2、R3Independently selected from hydrogen, cyano group, C1-C4 alkyl or substituted or unsubstituted following group：Benzene Base, naphthyl, anthryl, phenanthryl, fluorenyl, two fluorenyl of spiral shell, carbazyl, dibenzothiophene, dibenzofuran group, triazine radical, Sanya Phenyl, pyrenyl, quinolyl, isoquinolyl or pyridine radicals.
It should be noted that in the substituted all kinds of groups that the present invention mentions, the substituent is selected from the alkane of C1~C10 The heterocyclic radical of base, the aryl of C6~C30 or C4~C30.The number of the substituent is preferably 1~3.
Specifically, the naphtho- imdazole derivatives are preferably selected from such as any one in lower structure：
The present invention also provides a kind of synthetic method of naphtho- imdazole derivatives, syntheti c route are as follows：
Wherein, R1、R2、R3Independently selected from hydrogen, cyano group, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted The aryl of C6-C60, substituted or unsubstituted C3~C60 heterocyclic radical in one kind.
The present invention also provides a kind of organic electroluminescence device, including anode, cathode, it is placed in the anode and the cathode Between organic matter layer；The organic matter layer contains the naphtho- imdazole derivatives.
Preferably, the organic matter layer includes electron transfer layer, contains naphtho- miaow of the present invention in electron transfer layer Zole derivatives.
The present invention has no particular limits the raw material employed in following embodiments, can be for commercial product or using this Preparation method known to field technology personnel is prepared.
Embodiment 1：
The preparation of compound 1
Under the protection of argon gas, dichloromethane (45%, 200ml) is added to 1-1 (41.24g, 100.00mmol) and catalysis In agent 1-2 (9.54g, 100.00mmol), 24h is stirred at room temperature.With saturated sodium thiosulfate solution washed product, and use acetic acid Ethyl ester extracts.Have it is several layers of washed with saturated brine, and dried with anhydrous sodium sulfate.Decompression suction filtration is carried out to organic extract, It is recrystallized to give 1 36.76g, yield 83.45%.Mass spectrum m/z：440.55 (calculated values：440.56).Theoretical elemental content (%) C30H24N4：C, 81.79；H, 5.49；N, 12.72.Survey constituent content (%)：C, 81.78；H, 5.48；N, 12.73.On It is target product 1 to state confirmation and obtain product.
Embodiment 2
The preparation of compound 12
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 12.Mass spectrum m/ z：764.93 (calculated values：764.92).Theoretical elemental content (%) C56H36N4：C, 87.93；H, 4.74；N, 7.32.Survey element Content (%)：C, 87.92；H, 4.75；N, 7.33.It is target product 12 that above-mentioned confirmation, which obtains product,.
Embodiment 3
The preparation of compound 19
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 19.Mass spectrum m/ z：694.84 (calculated values：694.85).Theoretical elemental content (%) C37H28N4：C, 82.97；H, 4.93；N, 12.10.Actual measurement member Cellulose content (%)：C, 82.98；H, 4.94；N, 12.12.It is target product 19 that above-mentioned confirmation, which obtains product,.
Embodiment 4
The preparation of compound 28
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 28.Mass spectrum m/ z：893.11 (calculated values：893.12).Theoretical elemental content (%) C66H44N4：C, 88.76；H, 4.97；N, 6.27.Survey element Content (%)：C, 88.75；H, 4.98；N, 6.26.It is target product 28 that above-mentioned confirmation, which obtains product,.
Embodiment 5
The preparation of compound 33
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 33.Mass spectrum m/ z：817.01 (calculated values：817.02).Theoretical elemental content (%) C60H40N4：C, 88.21；H, 4.94；N, 6.86.Survey element Content (%)：C, 88.22；H, 4.92；N, 6.87.It is target product 33 that above-mentioned confirmation, which obtains product,.
Embodiment 6
The preparation of compound 48
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 48.Mass spectrum m/ z：818.98 (calculated values：818.97).Theoretical elemental content (%) C58H38N6：C, 85.06；H, 4.68；N, 10.26.Actual measurement member Cellulose content (%)：C, 85.06；H, 4.69；N, 10.25.It is target product 48 that above-mentioned confirmation, which obtains product,.
Embodiment 7
The preparation of compound 58
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 58.Mass spectrum m/ z：1019.22 (calculated value：1019.23).Theoretical elemental content (%) C74H46N6：C, 87.20；H, 4.55；N, 8.25.Actual measurement member Cellulose content (%)：C, 87.21；H, 4.56；N, 8.26.It is target product 58 that above-mentioned confirmation, which obtains product,.
Embodiment 8
The preparation of compound 68
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 68.Mass spectrum m/ z：981.30 (calculated values：981.31).Theoretical elemental content (%) C72H60N4：C, 88.13；H, 6.16；N, 5.71.Survey element Content (%)：C, 88.12；H, 6.17；N, 5.72.It is target product 68 that above-mentioned confirmation, which obtains product,.
Embodiment 9
The preparation of compound 72
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 72.Mass spectrum m/ z：987.23 (calculated values：987.24).Theoretical elemental content (%) C66H54N10：C, 80.30；H, 5.51；N, 14.19.Actual measurement member Cellulose content (%)：C, 80.31；H, 5.52；N, 14.18.It is target product 72 that above-mentioned confirmation, which obtains product,.
Embodiment 10
The preparation of compound 81
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 81.Mass spectrum m/ z：908.32 (calculated values：908.33).Theoretical elemental content (%) C54H34N6：C, 84.57；H, 4.47；N, 10.96.Actual measurement member Cellulose content (%)：C, 84.58；H, 4.45；N, 10.98.It is target product 81 that above-mentioned confirmation, which obtains product,.
Embodiment 11
The preparation of compound 88
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 88.Mass spectrum m/ z：915.07 (calculated values：915.08).Theoretical elemental content (%) C66H38N6：C, 86.63；H, 4.19；N, 9.18.Survey element Content (%)：C, 86.62；H, 4.20；N, 9.19.It is target product 88 that above-mentioned confirmation, which obtains product,.
Embodiment 12
The preparation of compound 95
By the R in embodiment 11、R2、R3Group replaces with R as implied above1、R2、R3Group, obtains compound 95.Mass spectrum m/ z：1073.36 (calculated value：1073.35).Theoretical elemental content (%) C80H56N4：C, 89.52；H, 5.26；N, 5.22.Actual measurement member Cellulose content (%)：C, 89.53；H, 5.27；N, 5.23.It is target product 95 that above-mentioned confirmation, which obtains product,.
Embodiment 13
The preparation of compound 102
By the R in embodiment 11、R2、R3、R4Group replaces with R as implied above1、R2、R3、R4Group, obtains compound 118. Mass spectrum m/z：831.08 (calculated values：831.09).Theoretical elemental content (%) C58H50N6：C, 83.82；H, 6.06；N, 10.11. Survey constituent content (%)：C, 83.83；H, 6.07；N, 10.12.It is target product 102 that above-mentioned confirmation, which obtains product,.
Embodiment 14
The preparation of compound 105
By the R in embodiment 11、R2、R3、R4Group replaces with R as implied above1、R2、R3、R4Group, obtains compound 121. Mass spectrum m/z：789.12 (calculated values：789.13).Theoretical elemental content (%) C56H60N4：C, 85.24；H, 7.66；N, 7.10.It is real Survey constituent content (%)：C, 85.25；H, 7.65；N, 7.12.It is target product 105 that above-mentioned confirmation, which obtains product,.
[contrast Application Example]
Transparent anode electrode ito substrate is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, Ran Hou Cleaned 2 minutes in plasma cleaning device, it is dry and be evacuated to 5 × 10-5Pa.Then the ito substrate after processing is steamed Plating.One layer of HAT-CN is deposited first as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 10nm.Followed by send out The luminous organic material CBP/Ir (ppy) is deposited in the evaporation of photosphere, mixing3, as green light phosphorescence dopant material, doping concentration For 5%, evaporation rate 0.005nm/s, evaporation thickness 30nm, the TPBi of 50nm is then deposited as electron transfer layer, steams Plating speed is 0.01nm/s, is used as cathode, thickness 30nm for vacuum evaporation Al layers on the electron transport layer.
[Application Example]
Transparent anode electrode ito substrate is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, Ran Hou Cleaned 2 minutes in plasma cleaning device, it is dry and be evacuated to 5 × 10-5Pa.Then the ito substrate after processing is steamed Plating.One layer of HAT-CN is deposited first as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 10nm.Followed by send out The luminous organic material CBP/Ir (ppy) is deposited in the evaporation of photosphere, mixing3, as green light phosphorescence dopant material, doping concentration For 5%, evaporation rate 0.005nm/s, evaporation thickness 30nm, the naphtho- imdazole derivatives of the present invention that 50nm is then deposited are made For electron transfer layer, evaporation rate 0.01nm/s, is used as cathode for vacuum evaporation Al layers, thickness is on the electron transport layer 30nm.The electron luminescence characteristic of the organic luminescent device of above method manufacture represents in the following table：
Result above shows that naphtho- imdazole derivatives of the invention are sent out as electron transport material applied to organic electroluminescence In optical device, luminous efficiency is high, 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 (7)

1. a kind of naphtho- imdazole derivatives, it is characterised in that there is structure shown in below formula (I)：
Wherein, R1、R2、R3Independently selected from hydrogen, cyano group, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6- The aryl of C60, substituted or unsubstituted C3~C60 heterocyclic radical in one kind.
2. naphtho- imdazole derivatives according to claim 1, it is characterised in that R1、R2、R3Independently selected from hydrogen, cyano group, take Generation or unsubstituted C1-C30 alkyl, the aryl of substituted or unsubstituted C6-C30, the heterocycle of substituted or unsubstituted C3~C30 One kind in base.
3. naphtho- imdazole derivatives according to claim 1, it is characterised in that R1、R2、R3Independently selected from hydrogen, cyano group, C1- C4 alkyl or substituted or unsubstituted following group：Phenyl, naphthyl, anthryl, phenanthryl, fluorenyl, two fluorenyl of spiral shell, carbazyl, hexichol Bithiophene base, dibenzofuran group, triazine radical, triphenylene, pyrenyl, quinolyl, isoquinolyl or pyridine radicals.
4. naphtho- imdazole derivatives according to claim 1, it is characterised in that any one in structure as shown below Kind：
5. the synthetic method of the naphtho- imdazole derivatives described in claim 1, it is characterised in that be prepared into by following route Arrive：
Wherein, R1、R2、R3Independently selected from hydrogen, cyano group, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6- The aryl of C60, substituted or unsubstituted C3~C60 heterocyclic radical in one kind.
A kind of 6. organic electroluminescence device, it is characterised in that including anode, cathode, be placed in the anode and the cathode it Between organic matter layer；The organic matter layer contains claim 1-4 any one of them naphtho- imdazole derivatives.
7. organic electroluminescence device according to claim 6, it is characterised in that passed in the organic matter layer containing electronics Defeated layer, contains claim 1-4 any one of them naphtho- imdazole derivatives in the electron transfer layer.
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Publication number Priority date Publication date Assignee Title
CN107805248A (en) * 2017-11-01 2018-03-16 长春海谱润斯科技有限公司 A kind of derivative containing benzimidazole structure and preparation method thereof and organic electroluminescence device
CN107915731A (en) * 2017-11-14 2018-04-17 长春海谱润斯科技有限公司 A kind of fused-ring derivatives and its synthetic method and organic luminescent device

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TW200918535A (en) * 2007-07-11 2009-05-01 Idemitsu Kosan Co Material for organic electroluminescent element, and organic electroluminescent element

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200918535A (en) * 2007-07-11 2009-05-01 Idemitsu Kosan Co Material for organic electroluminescent element, and organic electroluminescent element

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107805248A (en) * 2017-11-01 2018-03-16 长春海谱润斯科技有限公司 A kind of derivative containing benzimidazole structure and preparation method thereof and organic electroluminescence device
CN107915731A (en) * 2017-11-14 2018-04-17 长春海谱润斯科技有限公司 A kind of fused-ring derivatives and its synthetic method and organic luminescent device

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