CN107805243A - A kind of derivative containing naphthazine structure and preparation method thereof and organic electroluminescence device - Google Patents

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

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CN107805243A
CN107805243A CN201711054641.5A CN201711054641A CN107805243A CN 107805243 A CN107805243 A CN 107805243A CN 201711054641 A CN201711054641 A CN 201711054641A CN 107805243 A CN107805243 A CN 107805243A
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unsubstituted
substituted
naphthazine
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张弘
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

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Abstract

The present invention provides a kind of derivative containing naphthazine structure and preparation method thereof and organic electroluminescence device, belongs to organic photoelectrical material technical field.The compound has structure shown in formula (I).The present invention in naphthazine structure by adjusting R3、R4Improve the luminescent properties of material with benzene radicals in benzo carbazole structure etc., so as to get derivative be easy to the scattered and migration of electric charge, stability is good, and glass transition temperature is high, good film-forming property.Use the organic luminescent device provided by the invention prepared containing naphthazine structural derivative, with higher luminous efficiency, relatively low driving voltage, as the material of main part in organic electroluminescence device, the luminous efficiency of OLED can be effectively improved, better than existing conventional OLED.

Description

A kind of derivative containing naphthazine 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 containing naphthazine structure and its 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.OLED realizes that true color typically all uses RGB Pattern, but because the energy gap of blue light emitting material is larger, never suitable material of main part can be good at solving electric charge note Enter with transmit, luminous efficiency is low, unstable, short life the problem of, based on the requirement of organic luminescent device RGB true colors, blueness Luminescent material is indispensable, so it is good to develop a kind of carrier transmission performance, heat endurance, using showing as luminous efficiency Height, long lifespan, the luminescent layer material of main part of good film-forming property turn into a kind of urgent problem to be solved.
The content of the invention
It is an object of the invention to provide a kind of derivative containing naphthazine structure and preparation method thereof and organic electroluminescence to send out Optical device, derivative stability provided by the invention is good, and glass transition temperature is high, and good film-forming property, synthetic method is simple to operation, makes There is the organic electroluminescence device prepared with the derivative good luminous efficiency and life-span to show.
Present invention firstly provides a kind of derivative containing naphthazine structure, structural formula is：
Wherein, R1、R2、R5、R6The independent aryl, substituted or unsubstituted selected from H, substituted or unsubstituted C6-C60 One kind in C4~C60 heterocyclic radical；
R3、R4It is independent selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4~C60 One kind in heterocyclic radical；
X1、X2、X3、X4Independently selected from C or N, and at least one is N.
Preferably, R1、R2、R5、R6Independent is selected from H, substituted or unsubstituted C6-C30 aryl, substitution or unsubstituted C4~C30 heterocyclic radical in one kind；
R3、R4It is independent selected from singly-bound, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4~C30 One kind in heterocyclic radical.
Preferably, described R1、R2、R5、R6Independent is selected from H, phenyl, naphthyl, anthryl, phenanthryl, xenyl, terphenyl Base, fluorenyl, the fluorenyl of spiral shell two, pyridine radicals, carbazyl, dibenzothiophenes base, dibenzofuran group, quinolyl or isoquinolyl；R3、 R4Independent is selected from singly-bound, phenyl, naphthyl, anthryl, phenanthryl, xenyl, terphenyl, fluorenyl, the fluorenyl of spiral shell two, pyridine radicals, click Oxazolyl, dibenzothiophenes base, dibenzofuran group, quinolyl or isoquinolyl.
Preferably, any one of the derivative containing naphthazine structure in structure as shown below：
The present invention also provides a kind of preparation method containing naphthazine structural derivative, and syntheti c route is as follows：
Wherein, R1、R2、R5、R6The independent aryl, substituted or unsubstituted selected from H, substituted or unsubstituted C6-C60 One kind in C4~C60 heterocyclic radical；
R3、R4It is independent selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4~C60 One kind in heterocyclic radical；
X1、X2、X3、X4Independently selected from C or N, and at least one is N.
The present invention also provides a kind of organic electroluminescence device, including anode, negative electrode, organic matter layer；The organic matter layer Contain the derivative containing naphthazine structure.
Preferably, luminescent layer is contained in the organic matter layer, contains spreading out for described naphthazine structure in the luminescent layer Biology.
Beneficial effects of the present invention：
The present invention provides a kind of derivative containing naphthazine structure, and the compound has structure shown in formula (I), the present invention By adjusting R in naphthazine structure3、R4The luminescent properties of material are improved with benzene radicals in benzo carbazole structure etc., are made Obtained derivative is easy to the scattered and migration of electric charge, and stability is good, and glass transition temperature is high, good film-forming property, and then improves device Luminous efficiency.
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 compound containing naphthazine structure, structural formula is：
Wherein, R1、R2、R5、R6The independent aryl, substituted or unsubstituted selected from H, substituted or unsubstituted C6-C60 One kind in C4~C60 heterocyclic radical；
R3、R4It is independent selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4~C60 One kind in heterocyclic radical；
X1、X2、X3、X4Independently selected from C or N, and at least one is N.
Preferably, R1、R2、R5、R6Independent is selected from H, substituted or unsubstituted C6-C30 aryl, substitution or unsubstituted C4~C30 heterocyclic radical in one kind；
R3、R4It is independent selected from singly-bound, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4~C30 One kind in heterocyclic radical.
Preferably, R1、R2、R5、R6Independent is selected from H, phenyl, naphthyl, anthryl, phenanthryl, xenyl, terphenyl, fluorenes Base, the fluorenyl of spiral shell two, pyridine radicals, carbazyl, dibenzothiophenes base, dibenzofuran group, quinolyl or isoquinolyl；R3、R4It is independent Selected from singly-bound, phenyl, naphthyl, anthryl, phenanthryl, xenyl, terphenyl, fluorenyl, the fluorenyl of spiral shell two, pyridine radicals, carbazyl, two Benzothienyl, dibenzofuran group, quinolyl or isoquinolyl.
Preferably, any one of the derivative containing naphthazine structure in structure as shown below：
The present invention also provides a kind of preparation method of the derivative containing naphthazine structure, and syntheti c route is as follows：
Wherein, R1、R2、R5、R6The independent aryl, substituted or unsubstituted selected from H, substituted or unsubstituted C6-C60 One kind in C4~C60 heterocyclic radical；
R3、R4It is independent selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4~C60 One kind in heterocyclic radical；
X1、X2、X3、X4Independently selected from C or N, and at least one is N.
The present invention also provides a kind of organic electroluminescence device, including anode, negative electrode, organic matter layer；The organic matter layer Contain the derivative containing naphthazine 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 naphthazine knot containing described in the luminescent 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
1-2 preparation
Under blanket of nitrogen, add 1-1 (18.25g, 100.17mmol) and be dissolved in the anhydrous carbon tetrachloride of 500ml, add at -70 DEG C Enter 1.69g (10mmol) azodiisobutyronitrile, then add 39.12g (220mmol) NBS in four times, keep this temperature, after Continuous reaction 5 hours.Reaction terminates, and distills water washing, carbon dichloride extraction, anhydrous sodium sulfate drying, is evaporated under reduced pressure, passes through post layer Analysis purifying, obtains 1-2 31.25g, yield 78%.
1-5 preparation
1-3 (23.56g, 108.58mmol), addition 1-4 (27.59g, 108.58mmol), sodium carbonate (2.38g, 22.5mmol), Pd (PPh3) 4 (0.867g, 0.75mmol), toluene, ethanol, the mixed solvent of water, argon gas are replaced three times, backflow At a temperature of react 5h, after reaction terminates, add deionized water, separate organic phase, washing three times, concentration, obtained crude product mistake Silicagel column, intermediate products 30.23g is obtained, added in 250ml there-necked flasks and walk product, solvent o-dichlorohenzene, phosphorous triethylenetetraminehexaacetic acid Ester (50.6g, 305mmol), solution are heated to 150 DEG C of holding 15h.Solvent and unnecessary phosphorous triethylenetetraminehexaacetic acid are removed in vacuum distillation Ester, crude product pass through column chromatography.Obtain white solid.Obtain product 1-6 21.25g, yield 78.71%.
Compound TM1 preparation
By tri-butyl phosphine (3mL 1.0M toluene solution, 7.32mmol), palladium (0.4g, 1.83mmol) and uncle Sodium butoxide (10.8g, 100.25mmol) is added to 1-5 (24.57g, 91.92mmol) 1-2 (31.25g, 91.92mmol) de- Solution in gas toluene (500mL), and the mixture is heated 2 hours under reflux.The reactant mixture is cooled to room Temperature, filtered with dilution with toluene and via diatomite.The filtrate water is diluted, and extracted with toluene, and merges organic phase, It is evaporated under vacuo.The residue is filtered via silica gel, is recrystallized to give TM1 54.40g, yield is 83.03%.
Embodiment 2
Compound TM12 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Obtain compound TM12.Mass spectrum m/z：864.30 (calculated values：864.32).
Embodiment 3
Compound TM19 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Other steps are same as Example 1, obtain compound TM19.Mass spectrum m/z：709.25 (calculated values：709.26).
Embodiment 4
Compound TM28 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Other steps are same as Example 1, obtain compound TM28.Mass spectrum m/z：626.24 (calculated values：626.25).
Embodiment 5
Compound TM33 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Other steps are same as Example 1, obtain compound TM33.Mass spectrum m/z：862.31 (calculated values：862.32).
Embodiment 6
Compound TM48 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Obtain compound TM48.Mass spectrum m/z：711.24 (calculated values：711.23).
Embodiment 7
Compound TM58 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Other steps are same as Example 1, obtain compound TM58.Mass spectrum m/z：1019.40 (calculated value：1019.41).
Embodiment 8
Compound TM68 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Other steps are same as Example 1, obtain compound TM68.Mass spectrum m/z：788.27 (calculated values：788.28).
Embodiment 9
Compound TM72 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Other steps are same as Example 1, obtain compound TM72.Mass spectrum m/z：785.95 (calculated values：785.96).
Embodiment 10
Compound TM80 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Other steps are same as Example 1, obtain compound TM50.Mass spectrum m/z：785.29 (calculated values：785.31).
Embodiment 11
Compound TM82 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Other steps are same as Example 1, obtain compound TM82.Mass spectrum m/z：786.28 (calculated values：786.29).
Embodiment 12
Compound TM98 preparation
By the R in embodiment 13、R4And X1、X2、X3、X4Group replaces with R as implied above3、R4And X1、X2、X3、X4Group, Other steps are same as Example 1, obtain compound TM98.Mass spectrum m/z：787.27 (calculated values：787.28).
[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 One layer of NPB is deposited as hole transmission layer in method.Followed by the luminous organic material ADN/ is deposited in the evaporation of luminescent layer, mixing DPAP-DPPA, as blue light dopant material, doping concentration 5%, evaporation rate 0.005nm/s, evaporation thickness 30nm, Then evaporation 50nm TPBI is as electron transfer layer, evaporation rate 0.01nm/s, on the electron transport layer vacuum evaporation Al Layer is used as negative electrode, thickness 30nm.
[Application Example 1-10]
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 One layer of NPB is deposited as hole transmission layer in method.Followed by the evaporation of luminescent layer, mix and contain naphthazine structure described in evaporation Derivative/DPAP-DPPA, as blue light dopant material, doping concentration 5%, evaporation rate 0.005nm/s, evaporation thickness For 30nm, 50nm TPBI is then deposited as electron transfer layer, evaporation rate 0.01nm/s, vacuum on the electron transport layer Evaporating Al layer is as negative electrode, thickness 30nm.
The electron luminescence characteristic of the organic luminescent device of above method manufacture represents in the following table：
Result above shows that compound of the invention is as luminescent layer material of main part, 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 naphthazine structure, it is characterised in that there is structure shown in below formula (I)：
Wherein, R1、R2、R5、R6It is independent selected from H, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4~ One kind in C60 heterocyclic radical；
R3、R4Independent is selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4~C60 heterocycle One kind in base；
X1、X2、X3、X4Independently selected from C or N, and at least one is N.
2. the derivative according to claim 1 containing naphthazine structure, it is characterised in that R1、R2、R5、R6Independent is selected from H, one kind in substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4~C30 heterocyclic radical；
R3、R4Independent is selected from singly-bound, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4~C30 heterocycle One kind in base.
3. the derivative according to claim 1 containing naphthazine structure, it is characterised in that R1、R2、R5、R6Independent is selected from H, phenyl, naphthyl, anthryl, phenanthryl, xenyl, terphenyl, fluorenyl, the fluorenyl of spiral shell two, pyridine radicals, carbazyl, dibenzothiophenes Base, dibenzofuran group, quinolyl or isoquinolyl；R3、R4Independent is selected from singly-bound, phenyl, naphthyl, anthryl, phenanthryl, biphenyl Base, terphenyl, fluorenyl, the fluorenyl of spiral shell two, pyridine radicals, carbazyl, dibenzothiophenes base, dibenzofuran group, quinolyl or different Quinolyl.
4. the derivative according to claim 1 containing naphthazine structure, it is characterised in that in structure as shown below Any one：
5. the preparation method of the derivative containing naphthazine structure described in claim any one of 1-4, it is characterised in that pass through Following route synthesizes to obtain：
Wherein, R1、R2、R5、R6It is independent selected from H, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4~ One kind in C60 heterocyclic radical；
R3、R4Independent is selected from singly-bound, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C4~C60 heterocycle One kind in base；
X1、X2、X3、X4Independently selected from C or N, and at least one is N.
6. a kind of organic electroluminescence device, it is characterised in that the organic electroluminescence device includes anode, negative electrode, organic Nitride layer；The organic matter layer contains the derivative containing naphthazine structure described in claim any one of 1-4.
7. organic electroluminescence device according to claim 6, it is characterised in that containing luminous in the organic matter layer Layer, the derivative containing the naphthazine structure described in claim any one of 1-4 in the luminescent layer.
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WO2020098146A1 (en) * 2018-11-15 2020-05-22 武汉华星光电半导体显示技术有限公司 Blue light thermally activated delayed fluorescence material and use thereof
CN112457262A (en) * 2019-09-06 2021-03-09 创王(香港)股份有限公司 Organic electroluminescent compounds and organic electroluminescent device comprising the same

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