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CN107827807A - A kind of derivative containing carbazole structure and preparation method thereof and organic electroluminescence device - Google Patents

A kind of derivative containing carbazole structure and preparation method thereof and organic electroluminescence device Download PDF

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Publication number
CN107827807A
CN107827807A CN201710990960.0A CN201710990960A CN107827807A CN 107827807 A CN107827807 A CN 107827807A CN 201710990960 A CN201710990960 A CN 201710990960A CN 107827807 A CN107827807 A CN 107827807A
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unsubstituted
substituted
aryl
condensed
carbazole structure
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张弘
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Changchun Haipurunsi Technology Co Ltd
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Abstract

The present invention provides a kind of derivative containing carbazole structure and preparation method thereof and organic electroluminescence device, belongs to organic photoelectrical material technical field.The compound has structure shown in formula (I), by adjusting R on unsymmetric structure carbazole structure1、R2And Ar1、Ar2Group improves hole degree of excursion, improves hole transport performance, and then improves the luminous efficiency of device, is luminous organic material of good performance.

Description

A kind of derivative containing carbazole structure and preparation method thereof and organic electroluminescent Device
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of derivative and its system containing carbazole structure Preparation Method and organic electroluminescence device.
Background technology
With the progress of information industry, traditional display can not 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 of thin, small volume, it is in 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.Hole mobile material is mostly using tool at present There are diphenylamines or carbazole structure, the device defects containing this class formation are to launch the improvement of light luminosity with luminous efficiency Obvious to reduce, especially, in the case of passive drive, for practical application, moment needs thousands of cd/m2It is or higher Brightness, and the increase of luminous efficiency is important in high luminance area.However, due to triplet state inactivation in high-brightness region It is in the ascendance, therefore under conditions of the hole mobile material of current practice, the reduction of luminous efficiency can not be improved.
The content of the invention
The present invention provides a kind of derivative containing carbazole structure and preparation method thereof and organic electroluminescence device, this hair Bright is to improve hole degree of excursion by carbazole structure, there is provided hole transport and the maximized compound of illumination effect, and will This derivative containing carbazole structure is prepared into device, and it has good luminous efficiency.
Present invention firstly provides a kind of derivative containing carbazole structure, structural formula is：
Wherein, R1Selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 it is thick Ring, substituted or unsubstituted C8~C60 condensed hetero ring in one kind；R2It is alkyl selected from C1~C10, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 condensed ring in one kind；Ar1、Ar2Do not take independently selected from substitution or For C6~C60 aryl, substituted or unsubstituted C10~C60 condensed ring, substituted or unsubstituted C8~C60 condensed hetero ring in It is a kind of..
Preferably, the R1Selected from singly-bound, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10~ C30 condensed ring, substituted or unsubstituted C8~C30 condensed hetero ring in one kind；R2Alkyl selected from C1~C4, substitution do not take The C6-C30 in generation aryl, substituted or unsubstituted C10~C30 condensed ring in one kind；Ar1、Ar2Independently selected from substitution or Unsubstituted C6~C30 aryl, substituted or unsubstituted C10~C30 condensed ring, substituted or unsubstituted C8~C30 condensed hetero ring In one kind.
Preferably, the R1Selected from singly-bound, phenyl, naphthyl, xenyl, quinolyl or isoquinolyl；R2Selected from methyl, second Base, propyl group, phenyl, naphthyl, xenyl, quinolyl or isoquinolyl；Ar1、Ar2Independently selected from phenyl, naphthyl, anthryl, phenanthrene Base, xenyl, terphenyl, fluorenyl, the fluorenyl of spiral shell two, carbazyl, dibenzothiophenes base, dibenzofuran group, quinolyl or different Quinolyl.
Preferably, any one of the compound containing carbazole structure in structure as shown below：
The present invention also provides a kind of preparation method of the derivative containing carbazole structure, and syntheti c route is as follows：
Wherein, R1Selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 it is thick Ring, substituted or unsubstituted C8~C60 condensed hetero ring in one kind；R2It is alkyl selected from C1~C10, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 condensed ring in one kind；Ar1、Ar2Do not take independently selected from substitution or For C6~C60 aryl, substituted or unsubstituted C10~C60 condensed ring, substituted or unsubstituted C8~C60 condensed hetero ring in It is a kind of
The present invention also provides a kind of organic electroluminescence device, including anode, negative electrode, is placed in the anode and the negative electrode Between organic matter layer；The organic matter layer contains the described derivative containing carbazole structure.
Preferably, contain hole transmission layer in the organic matter layer, contain click containing described in the hole transmission layer The derivative of azoles structure.
Beneficial effects of the present invention:
Present invention firstly provides a kind of derivative containing carbazole structure, the compound has structure shown in formula (I), passes through R is adjusted on unsymmetric structure carbazole structure1、R2And Ar1、Ar2Group improves hole degree of excursion, improves hole transport performance, And then improve the luminous efficiency of device.
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 derivative containing carbazole structure, has structure shown in below formula (I)：
Wherein, R1Selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 it is thick Ring, substituted or unsubstituted C8~C60 condensed hetero ring in one kind；R2It is alkyl selected from C1~C10, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 condensed ring in one kind；Ar1、Ar2Do not take independently selected from substitution or For C6~C60 aryl, substituted or unsubstituted C10~C60 condensed ring, substituted or unsubstituted C8~C60 condensed hetero ring in It is a kind of.
Preferably, R1Selected from singly-bound, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10~C30 Condensed ring, substituted or unsubstituted C8~C30 condensed hetero ring in one kind；R2It is alkyl selected from C1~C4, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10~C30 condensed ring in one kind；Ar1、Ar2Do not take independently selected from substitution or For C6~C30 aryl, substituted or unsubstituted C10~C30 condensed ring, substituted or unsubstituted C8~C30 condensed hetero ring in It is a kind of.
Preferably, R1Selected from singly-bound, phenyl, naphthyl, xenyl, quinolyl or isoquinolyl；R2Selected from methyl, ethyl, third Base, phenyl, naphthyl, xenyl, quinolyl or isoquinolyl；Ar1、Ar2Independently selected from phenyl, naphthyl, anthryl, phenanthryl, biphenyl Base, terphenyl, fluorenyl, the fluorenyl of spiral shell two, carbazyl, dibenzothiophenes base, dibenzofuran group, quinolyl or isoquinolyl.
Specifically, the derivative containing carbazole structure is preferably selected from any one in following structure：
The present invention also provides a kind of preparation method of the derivative containing carbazole structure, and syntheti c route is as follows：
Wherein, R1Selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 it is thick Ring, substituted or unsubstituted C8~C60 condensed hetero ring in one kind；R2It is alkyl selected from C1~C10, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 condensed ring in one kind；Ar1、Ar2Do not take independently selected from substitution or For C6~C60 aryl, substituted or unsubstituted C10~C60 condensed ring, substituted or unsubstituted C8~C60 condensed hetero ring in It is a kind of.
The present invention also provides a kind of organic electroluminescence device, including anode, negative electrode, is placed in the anode and the negative electrode Between organic matter layer；The organic matter layer contains the described derivative containing carbazole structure.
Hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole resistance are comprised at least in above-mentioned organic matter layer At least one layer in barrier, electron transfer layer, electron injecting layer.It is preferred that contain carbazole containing described in the hole transmission layer The derivative of structure.
The present invention has no particular limits to the raw material employed in following examples, can be for commercially available prod or using this Preparation method known to art personnel is prepared.
Embodiment 1：
Compound TM1 preparation
1-3 preparation
Under the protection of nitrogen, the addition compound 1-1 (6.89g, 41.28mmol) into 2L reactors, 1-2 (11.80g, 41.28mmol), potassium carbonate (4.39g, 31.75mmol), toluene 200mL are stirred.Reactor temperature is raised to 70 DEG C, adds Pd (PPh3)4(1.04g, 0.90mmol), distilled water 100mL stirrings, is stirred at reflux 11h, fully reaction.It is whole to add 70mL distilled water After only reacting, it is filtered under diminished pressure, with distillation water washing solid, then with acetone, toluene, THF is recrystallized, and is risen again after obtaining solid China, re crystallization from toluene, obtain 1-3 12.89g, yield 80.89%.
1-4 preparation
In 250ml three-necked flasks, 1-3 (12.89g, 41.28mmol), solvent o-dichlorohenzene, triethyl phosphite are added 200ml, solution are heated to 150 DEG C, keep 15h.Solvent and unnecessary triethyl phosphite are removed in vacuum distillation, and crude product passes through post Chromatography, obtains product 1-4 9.26g, yield 79.57%.
1-6 preparation
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle Sodium butoxide (1.6g, 52mmol) is added to 1-4 (9.26g, 31.27mmol) 1-5 (6.38g, 31.27mmol) in degassed toluene Solution in (200mL), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to room temperature, uses first Benzene dilutes and filtered via diatomite.The filtrate water is diluted, and extracted with toluene, and merges organic phase, by its It is evaporated under vacuum.The residue is filtered via silica gel, is recrystallized to give 1-6 9.52g, yield 81.81%.
1-8 preparation
Under the protection of nitrogen, the addition compound 1-6 (9.52g, 25.57mmol) into 2L reactors, 1-7 (6.49g, 25.57mmol), potassium carbonate (4.39g, 19.72mmol), toluene 200mL are stirred.Reactor temperature is raised to 70 DEG C, adds Pd (PPh3)4(1.04g, 0.90mmol), distilled water 100mL stirrings, is stirred at reflux 11h, fully reaction.It is whole to add 70mL distilled water After only reacting, it is filtered under diminished pressure, with distillation water washing solid, then with acetone, toluene, THF is recrystallized, and is risen again after obtaining solid China, re crystallization from toluene, obtain 1-8 8.14g, yield 75.94%.
1-10 preparation
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle Sodium butoxide (1.6g, 52mmol) is added to 1-8 (8.14g, 19.41mmol) 1-9 (5.49g, 19.41mmol) in degassed toluene Solution in (200mL), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to room temperature, uses first Benzene dilutes and filtered via diatomite.The filtrate water is diluted, and extracted with toluene, and merges organic phase, by its It is evaporated under vacuum.The residue is filtered via silica gel, is recrystallized to give 1-10 6.8g, yield 78.13%.
Compound TM1 preparation
Into two mouthfuls of clean flasks add intermediate 1-10 (7.73g, 15.17mmol) and 1-11 (2.57g, 15.17mmol), at the same add alchlor (1.44g, 14.10mmol), alundum (Al2O3) (1.44g, 14.10mmol) and 30ml dimethylbenzene, under nitrogen protection, system is heated to 70-80 degree, successive reaction 8 hours.After being cooled to room temperature, using second Ether/deionized water extraction, is then separated using silica gel column layer, while is dried using anhydrous magnesium sulfate, obtains product 6.38g, yield 78.43%.Mass spectrum m/z：536.23 (calculated values：536.25).Theoretical elemental content (%) C40H28N2：C, 89.52；H, 5.26；N, 5.22.Survey constituent content (%)：C, 89.53；H, 5.25；N, 5.23.Above-mentioned confirmation obtains product Target product TM1.
Embodiment 2
Compound TM7 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM3.Mass spectrum m/z：587.24 (calculated values：587.25).
Embodiment 3
Compound TM12 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM12.Mass spectrum m/z：642.21 (calculated values：642.23).
Embodiment 4
Compound TM14 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM14.Mass spectrum m/z：626.24 (calculated values：626.25).
Embodiment 5
Compound TM15 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM15.Mass spectrum m/z：701.28 (calculated values：701.29).
Embodiment 6
Compound TM18 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM18.Mass spectrum m/z：774.30 (calculated values：774.35).
Embodiment 7
Compound TM26 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM26.Mass spectrum m/z：511.20 (calculated values：511.23).
Embodiment 8
Compound TM36 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM36.Mass spectrum m/z：698.27 (calculated values：698.25).
Embodiment 9
Compound TM44 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM44.Mass spectrum m/z：612.23 (calculated values：612.25).
Embodiment 10
Compound TM50 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM50.Mass spectrum m/z：790.31 (calculated values：790.32).
Embodiment 11
Compound TM68 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM68.Mass spectrum m/z：702.27 (calculated values：702.28).
Embodiment 12
Compound TM80 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM80.Mass spectrum m/z：613.23 (calculated values：613.25).
Embodiment 13
Compound TM126 preparation
By the R in embodiment 11、R2And Ar1、Ar2Group replaces with R as implied above1、R2And Ar1、Ar2Group, other steps It is same as Example 1, obtain compound TM126.Mass spectrum m/z：1012.38 (calculated value：1012.39).
[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, dry and be evacuated to 5 × 10-5Pa.Then the ito substrate after processing is steamed Plating.One layer of 2-TNATA is deposited first as hole injection layer, evaporation rate 0.1nm/s, evaporation thickness 10nm.With same Method is deposited one layer of α-NPD and is used as hole transmission layer.Followed by the luminous organic material is deposited in the evaporation of luminescent layer, mixing AND/DPAP-DPPA, it is as blue light dopant material, doping concentration 5%, evaporation rate 0.005nm/s, evaporation thickness 30nm, 50nm TPBI is then deposited as electron transfer layer, evaporation rate 0.01nm/s, on the electron transport layer vacuum steaming Al layers are plated as negative electrode, thickness 30nm.
[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, dry and be evacuated to 5 × 10-5Pa.Then the ito substrate after processing is steamed Plating.One layer of 2-TNATA is deposited first as hole injection layer, evaporation rate 0.1nm/s, evaporation thickness 10nm.With same Method is deposited one layer of present invention and contains the derivative of carbazole structure as hole transmission layer.Followed by the evaporation of luminescent layer, mixing The luminous organic material AND/DPAP-DPPA is deposited, is as blue light dopant material, doping concentration 5%, evaporation rate 0.005nm/s, evaporation thickness 30nm, 50nm TPBI is then deposited as electron transfer layer, evaporation rate 0.01nm/s, Vacuum evaporation Al layers are as negative electrode, thickness 30nm on the electron transport layer.
The electron luminescence characteristic of the organic luminescent device of above method manufacture represents in the following table：
Result above shows that compound thing of the invention is as hole mobile material, applied to organic electroluminescence device In, 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 derivative containing carbazole structure, it is characterised in that there is structure shown in below formula (I)：
Wherein, R1Selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 condensed ring, take One kind in generation or unsubstituted C8~C60 condensed hetero ring；R2Alkyl selected from C1~C10, substituted or unsubstituted C6-C60 Aryl, substituted or unsubstituted C10~C60 condensed ring in one kind；Ar1、Ar2Independently selected from substitution or unsubstituted C6~ C60 aryl, substituted or unsubstituted C10~C60 condensed ring, substituted or unsubstituted C8~C60 condensed hetero ring in one kind.
2. the derivative according to claim 1 containing carbazole structure, it is characterised in that R1Do not take selected from singly-bound, substitution or The C6-C30 in generation aryl, substituted or unsubstituted C10~C30 condensed ring, substituted or unsubstituted C8~C30 condensed hetero ring in One kind；R2Alkyl selected from C1~C4, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10~C30 One kind in condensed ring；Ar1、Ar2Independently selected from substitution or unsubstituted C6~C30 aryl, substituted or unsubstituted C10~C30 Condensed ring, substituted or unsubstituted C8~C30 condensed hetero ring in one kind.
3. the derivative according to claim 1 containing carbazole structure, it is characterised in that R1Selected from singly-bound, phenyl, naphthyl, Xenyl, quinolyl or isoquinolyl；R2Selected from methyl, ethyl, propyl group, phenyl, naphthyl, xenyl, quinolyl or isoquinolin Base；Ar1、Ar2Independently selected from phenyl, naphthyl, anthryl, phenanthryl, xenyl, terphenyl, fluorenyl, the fluorenyl of spiral shell two, carbazyl, Dibenzothiophenes base, dibenzofuran group, quinolyl or isoquinolyl.
4. the derivative according to claim 1 containing carbazole structure, it is characterised in that in structure as shown below Any one：
5. the preparation method of the derivative containing carbazole structure described in claim any one of 1-4, it is characterised in that by such as Lower route synthesizes to obtain：
Wherein, R1Selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C10~C60 condensed ring, take One kind in generation or unsubstituted C8~C60 condensed hetero ring；R2Alkyl selected from C1~C10, substituted or unsubstituted C6-C60 Aryl, substituted or unsubstituted C10~C60 condensed ring in one kind；Ar1、Ar2Independently selected from substitution or unsubstituted C6~ C60 aryl, substituted or unsubstituted C10~C60 condensed ring, substituted or unsubstituted C8~C60 condensed hetero ring in one kind.
A kind of 6. organic electroluminescence device, it is characterised in that including anode, negative electrode, be placed in the anode and the negative electrode it Between organic matter layer；The organic matter layer contains the derivative containing carbazole structure described in claim any one of 1-4.
7. organic electroluminescence device according to claim 6, it is characterised in that passed in the organic matter layer containing hole Defeated layer, the derivative containing carbazole structure in the hole transmission layer described in containing claim any one of 1-4.
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