CN107698488A - A kind of benzo carbazole analog derivative and its organic luminescent device - Google Patents

A kind of benzo carbazole analog derivative and its organic luminescent device Download PDF

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CN107698488A
CN107698488A CN201710928400.2A CN201710928400A CN107698488A CN 107698488 A CN107698488 A CN 107698488A CN 201710928400 A CN201710928400 A CN 201710928400A CN 107698488 A CN107698488 A CN 107698488A
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unsubstituted
substituted
benzo carbazole
analog derivative
organic
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蔡辉
韩春雪
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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 benzo carbazole analog derivative and its organic luminescent device, belongs to technical field of organic luminescence materials.Solve the problems, such as that device light emitting efficiency is low in the prior art, service life is short.The benzo carbazole analog derivative of the present invention, available for luminescent layer material of main part, compared with prior art, the luminous efficiency of OLED and the life-span of OLED can be effectively lifted, can be applied to show, illuminate, the field such as organic photovoltaic cell, Electronic Paper, Organophotoreceptor or OTFT.

Description

A kind of benzo carbazole analog derivative and its organic luminescent device
Technical field
The present invention relates to organic photoelectrical material technical field, more particularly to a kind of benzo carbazole analog derivative and its organic hair Optical device.
Background technology
Organic electroluminescent LED (Organic Light-Emitting Diode, OLED) refers to luminous organic material The diode to be lighted in the presence of electric current or electric field, electric energy can be converted into luminous energy by it.Kodak Company in 1987 Tang etc. has invented sandwich type organic bilayer film luminescent device, this breakthrough, allows it is seen that OLED technology Move towards practical, move towards the great potential of commercial market, started the research boom of Organic Light Emitting Diode.Over 30 years, OLED Technology achieves development with rapid changepl. never-ending changes and improvements, is moved towards the industrialization production from laboratory research.All solid state, the active of OLED technology Luminous, high-contrast, it is ultra-thin, can Flexible Displays, low-power consumption, wide viewing angle, fast response time, operating temperature range is wide, it is real to be easy to Many advantages, such as existing 3D display, " fantasy display " is referred to as by professional, will turn into following most potential new Type Display Technique.
All in all, following OLED direction is to develop high efficiency, high brightness, the white light parts that the life-span is good, inexpensive And full color display device, but the technological industrialization process still faces many problems.Therefore, design is with finding a kind of chemical combination Thing, it is in OLED material research work as OLED new materials to overcome the shortcomings of that it occurs in actual application Emphasis and Development Trend from now on.
The content of the invention
In view of this, it is an object of the invention to provide a kind of benzo carbazole analog derivative and its organic luminescent device.Adopt The organic luminescent device prepared with benzo carbazole analog derivative of the present invention, has higher luminous efficiency and device longevity Order the advantages of good.
Present invention firstly provides a kind of benzo carbazole analog derivative, structural formula is：
Wherein, Ar1、Ar2Independent is selected from substituted or unsubstituted C6~C60 aryl, substituted or unsubstituted C10~C60 Condensed ring radical or substituted or unsubstituted C4~C60 heterocyclic radicals.
Preferably, the Ar1、Ar2It is independent selected from substituted or unsubstituted C6~C30 aryl, it is substituted or unsubstituted C10~C30 condensed ring radicals or substituted or unsubstituted C4~C30 heterocyclic radicals.
Preferably, the Ar1、Ar2It is independent selected from substituted or unsubstituted phenyl, naphthyl, anthryl, phenanthryl, xenyl, It is terphenyl, dibenzofuran group, dibenzothiophenes base, substituted or unsubstituted fluorenyl, the fluorenyl of spiral shell two, substituted or unsubstituted Pyrimidine radicals, substituted or unsubstituted triazine radical or substituted or unsubstituted carbazyl.
Preferably, shown in any one in the following compound 1-60 of the benzo carbazole analog derivative：
The present invention provides a kind of organic luminescent device, including anode, negative electrode and between the anode and negative electrode Several organic function layers, at least contain described benzo carbazole analog derivative in the organic function layer
Preferably, described benzo carbazole derivative is used as luminescent layer material of main part in an organic light emitting device.
Beneficial effects of the present invention：
Benzo carbazole derivative provided by the invention can be used for organic luminescent device, especially as in organic luminescent device Luminescent layer material of main part, higher luminous efficiency is shown and the advantages of the life-span substantially increases, better than existing conventional OLED Device.
Embodiment
For a further understanding of the present invention, below in conjunction with the preferred embodiment of the present invention technical scheme carry out it is clear, complete Site preparation describes, it is clear that described embodiment is only part of the embodiment of the present invention, rather than whole embodiments.
First the invention provides a kind of benzo carbazole analog derivative, there is structural formula shown in formula (I)：
Wherein, Ar1、Ar2Independent is selected from substituted or unsubstituted C6~C60 aryl, substituted or unsubstituted C10~C60 Condensed ring radical or substituted or unsubstituted C4~C60 heterocyclic radicals.
Preferably, Ar1、Ar2It is independent selected from substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C10~ C30 condensed ring radicals or substituted or unsubstituted C4~C30 heterocyclic radicals.
According to the present invention, the substituted aryl, substitution heterocyclic radical, substitution condensed ring radical in, the substituent can be only C1~C4 alkyl, C6~C30 aryl, C10~C30 condensed ring radicals or C4~C30 heterocyclic radicals are on the spot selected from, for example, may be selected from first Base, ethyl, isopropyl, phenyl, naphthyl, anthryl, phenanthryl, xenyl, terphenyl, dibenzofuran group, dibenzothiophenes base, Fluorenyl, the fluorenyl of spiral shell two, pyrimidine radicals, triazine radical, carbazyl etc., but not limited to this.
Preferably, the Ar1、Ar2It is independent selected from substituted or unsubstituted phenyl, naphthyl, anthryl, phenanthryl, xenyl, It is terphenyl, dibenzofuran group, dibenzothiophenes base, substituted or unsubstituted fluorenyl, the fluorenyl of spiral shell two, substituted or unsubstituted Pyrimidine radicals, substituted or unsubstituted triazine radical or substituted or unsubstituted carbazyl.
Specifically, the benzo carbazole analog derivative is preferably selected from any one in structure shown in following 1~60：
Some specific structure types of benzo carbazole derivative of the present invention are enumerated above, but it is of the present invention Benzo carbazole derivative be not limited to these listed chemical constitutions, every based on structure shown in formula (I), Ar1、Ar2 It should be all included for group as defined above.
The preparation method of benzo carbazole derivative of the present invention, it can be obtained by reaction as follows shown in formula (I) Benzo carbazole derivative：
Benzo carbazole derivative shown in formula (I) of the present invention can be prepared into by Suzuki coupling reactions and ullmann reaction Arrive, using popular response condition well-known to those skilled in the art.The present invention is to employed in this above-mentioned all kinds of reaction The source of raw material have no particular limits, commercially available prod raw material can be used or use system well-known to those skilled in the art Preparation Method is prepared.
The present invention still further provides a kind of organic luminescent device, including anode, negative electrode and positioned at the anode with it is cloudy Several organic function layers between pole, at least contain described benzo carbazole analog derivative in the organic function layer.
Above-mentioned organic function layer wherein at least includes hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, sky At least one layer in cave barrier layer, electron transfer layer, electron injecting layer, preferably described benzo carbazole analog derivative is in organic hair It is used as luminescent layer material of main part in optical device.
The organic luminescent device of the present invention can be used in display, illumination, organic photovoltaic cell (OSC), Electronic Paper (e- Paper), the field such as Organophotoreceptor (OPC) or OTFT.
The present invention has no particular limits to the source of the raw material employed in following examples, can be commercially available prod or It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1：The preparation of compound 1
Intermediate 1-A preparation：
Compound a (15.50g, 37.6mmol) is dissolved in tetrahydrofuran (140mL), and hexane is added dropwise under the conditions of -78 DEG C After solvent and 2.5M n-BuLis (18mL, 45.1mmol), stir 1 hour.Again slowly be added dropwise trimethylborate (13mL, After 56.4mmol), 2h is stirred.2M hydrochloric acid is added dropwise again to neutralize, extract product with ethyl acetate and water.With dichloromethane and hexane It is recrystallized to give compound b (6.57g, 47%).Weigh Compound b (93.38g, 251mmol), compound c (50.7g, 251mmol), tetra-triphenylphosphine palladium (11g, 10mmol) and potassium carbonate (84.2g, 609mmol), the reactant weighed is dissolved in In the solvent of toluene (1L)/EtOH (200mL)/distilled water (200mL), 90 DEG C are heated 2 hours.Weigh Compound d (38.73g, 78mmol), add triethyl phosphite (200mL) and dichloro-benzenes (150mL), stir 12 hours at 150 DEG C, react end with After be concentrated under reduced pressure, be extracted with ethyl acetate and concentrate again, obtain intermediate 1-A (18.56g, 55%) with column chromatography.
Mass spectrum m/z：432.17 (calculated values：432.16).Theoretical elemental content (%) C32H20N2：C, 88.86；H, 4.66； N, 6.48 actual measurement constituent contents (%)：C, 88.87；H, 4.65；N, 6.48.The above results confirm that it is target product to obtain product.
Intermediate 1-B preparation：
Weigh intermediate 1-A (17.73g, 41mmol), compound e (8.47g, 41.5mmol), cuprous iodide (3.9g, 20.5mmol), ethylenediamine (1.4mL, 20.5mmol) and cesium carbonate (40g, 123mmol), and it is added to toluene by said sequence In (250mL), return stirring.Vacuum distillation, dichloromethane and hexane is extracted with ethyl acetate crosses pillar and obtain intermediate 1-B (17.31g, 83%).
Mass spectrum m/z：508.20 (calculated values：508.19).Theoretical elemental content (%) C38H24N2：C, 89.74；H, 4.76； N, 5.51 actual measurement constituent contents (%)：C, 89.75；H, 4.75；N, 5.51.The above results confirm that it is target product to obtain product.
The preparation of compound 1：
Weigh intermediate 1-B (15.64g, 30.75mmol), compound e (6.28g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added to toluene In (200mL), return stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane is crossed pillar and recrystallized again To target product compound 1 (13.49g, 75%).
Mass spectrum m/z：584.24 (calculated values：584.23).Theoretical elemental content (%) C44H28N2：C, 90.38；H, 4.83； N, 4.79 actual measurement constituent contents (%)：C, 90.38；H, 4.84；N, 4.78.The above results confirm that it is target product to obtain product.
Embodiment 2：The preparation of compound 2
Intermediate 2-B preparation：
Weigh intermediate 1-A (17.73g, 41mmol), compound f (10.54g 41.5mmol), cuprous iodide (3.9g, 20.5mmol), ethylenediamine (1.4mL, 20.5mmol) and cesium carbonate (40g, 123mmol), and it is added to toluene by said sequence In (250mL), return stirring.Vacuum distillation, dichloromethane and hexane is extracted with ethyl acetate crosses pillar and obtain intermediate 2-B (21.60g, 83%).
Mass spectrum m/z：558.22 (calculated values：558.21).Theoretical elemental content (%) C42H26N2：C, 90.29；H, 4.69； N, 5.01 actual measurement constituent contents (%)：C, 90.29；H, 4.68；N, 5.02.The above results confirm that it is target product to obtain product.
The preparation of compound 2：
Weigh intermediate 2-B (17.18g, 30.75mmol), compound f (7.83g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added to toluene In (200mL), return stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane is crossed pillar and recrystallized again To target product compound 2 (15.79g, 75%).
Mass spectrum m/z：684.27 (calculated values：684.26).Theoretical elemental content (%) C528H32N2：C, 91.20；H, 4.71； N, 4.09 actual measurement constituent contents (%)：C, 91.21；H, 4.70；N, 4.09.The above results confirm that it is target product to obtain product.
Embodiment 3：The preparation of compound 4
Take intermediate 1-B (15.64g, 30.75mmol), compound g (7.83g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added in toluene (200mL), return Stream stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane crosses pillar and is recrystallized to give target product again Compound 4 (14.83g, 76%).
Mass spectrum m/z：634.25 (calculated values：634.24).Theoretical elemental content (%) C48H30N2：C, 90.82；H, 4.76； N, 4.41 actual measurement constituent contents (%)：C, 90.83；H, 4.75；N, 4.41.The above results confirm that it is target product to obtain product.
Embodiment 4：The preparation of compound 10
Weigh intermediate 1-B (15.64g, 30.75mmol), compound h (9.06g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added to toluene In (200mL), return stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane is crossed pillar and recrystallized again To target product compound 10 (15.56g, 75%).
Mass spectrum m/z：674.25 (calculated values：674.24).Theoretical elemental content (%) C50H30N2O：C, 89.00；H, 4.48； N, 4.15；O, 2.37 actual measurement constituent contents (%)：C, 89.01；H, 4.47；N, 4.14；O, 2.38.The above results confirm to be produced Thing is target product.
Embodiment 5：The preparation of compound 18
Take intermediate 1-B (15.64g, 30.75mmol), compound i (6.31g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added in toluene (200mL), return Stream stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane crosses pillar and is recrystallized to give target product again Compound 18 (13.69g, 76%).
Mass spectrum m/z：585.23 (calculated values：585.22).Theoretical elemental content (%) C43H27N3：C, 88.18；H, 4.65； N, 7.17 actual measurement constituent contents (%)：C, 88.19；H, 4.64；N, 7.17.The above results confirm that it is target product to obtain product.
Embodiment 6：The preparation of compound 25
Take intermediate 1-B (15.64g, 30.75mmol), compound j (6.33g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added in toluene (200mL), return Stream stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane crosses pillar and is recrystallized to give target product again Compound 25 (13.53g, 75%).
Mass spectrum m/z：586.23 (calculated values：586.22).Theoretical elemental content (%) C42H26N4：C, 85.98；H, 4.47； N, 9.55 actual measurement constituent contents (%)：C, 85.98；H, 4.46；N, 9.56.The above results confirm that it is target product to obtain product.
Embodiment 7：The preparation of compound 26
Take intermediate 1-B (15.64g, 30.75mmol), compound k (6.37g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added in toluene (200mL), return Stream stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane crosses pillar and is recrystallized to give target product again Compound 26 (13.55g, 75%).
Mass spectrum m/z：587.22 (calculated values：587.21).Theoretical elemental content (%) C41H25N5：C, 83.79；H, 4.29； N, 11.92 actual measurement constituent contents (%)：C, 83.79；H, 4.28；N, 11.93.The above results confirm that obtain product produces for target Product.
Embodiment 8：The preparation of compound 31
Take intermediate 1-B (15.64g, 30.75mmol), compound m (11.03g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added in toluene (200mL), return Stream stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane crosses pillar and is recrystallized to give target product again Compound 31 (17.04g, 76%).
Mass spectrum m/z：738.29 (calculated values：738.28).Theoretical elemental content (%) C54H34N4：C, 87.78；H, 4.64； N, 7.58 actual measurement constituent contents (%)：C, 87.79；H, 4.63；N, 7.58.The above results confirm that it is target product to obtain product.
Embodiment 9：The preparation of compound 46
Take intermediate 1-B (15.64g, 30.75mmol), compound n (10.23g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added in toluene (200mL), return Stream stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane crosses pillar and is recrystallized to give target product again Compound 46 (17.10g, 78%).
Mass spectrum m/z：712.27 (calculated values：712.26).Theoretical elemental content (%) C52H32N4：C, 87.62；H, 4.52； N, 7.86 actual measurement constituent contents (%)：C, 87.63；H, 4.51；N, 7.86.The above results confirm that it is target product to obtain product.
Embodiment 10：The preparation of compound 58
Take intermediate 1-B (15.64g, 30.75mmol), compound o (9.86g, 30.8mmol), cuprous iodide (2.9g, 15.4mmol), ethylenediamine (1.1ml, 20.5mmol) and Cs2CO3 (30g, 92.3mmol), are added in toluene (200mL), return Stream stirring 24 hours.Vacuum distillation is extracted with ethyl acetate, dichloromethane/hexane crosses pillar and is recrystallized to give target product again Compound 58 (18.16g, 76%).
Mass spectrum m/z：776.33 (calculated values：776.32).Theoretical elemental content (%) C59H40N2：C, 91.21；H, 5.19； N, 3.61 actual measurement constituent contents (%)：C, 91.21；H, 5.18；N, 3.62.The above results confirm that it is target product to obtain product.
Comparing embodiment 1：
Ito glass substrate is placed in distilled water and cleaned 2 times, ultrasonic washing 30 minutes, 2 are cleaned repeatedly with distilled water It is secondary, ultrasonic washing 10 minutes, distilled water cleaning terminate after, isopropanol, acetone, methanol equal solvent in order ultrasonic washing with After dry, be transferred in plasma washing machine, by aforesaid substrate wash 5 minutes, be sent in evaporator.
Hole injection layer will be deposited on the ito transparent electrode being already prepared toHole transport is deposited Layer a-NPD ((N, N'- bis- (1- naphthyls)-N, N'- diphenyl-(1,1'- biphenyl) -4,4'- diamines))/Luminescent layer is deposited Material of main part 3Ph-Anthracene or embodiments of the invention material and dopant Ir (ppy)3(5%) it is depositedSo After electron transfer layer is depositedElectron injecting layerNegative electrodeSaid process organic matter steams Plating speed is to maintainLiF isAl is
[embodiment 1-5]
By (the Alq in comparing embodiment 13) change shown compound 1,2,4,10,58 in embodiment 1-5 into.
Table 1 is part of compounds prepared by the embodiment of the present invention and compares the characteristics of luminescence of the luminescent device of material preparation Test result.
The characteristics of luminescence test of [table 1] luminescent device
From the above-mentioned result of table 1, it is seen that the luminous efficiency and life characteristic of benzo carbazole derivative of the invention have aobvious The raising of work.
Comparing embodiment 2：
Ito glass substrate is placed in distilled water and cleaned 2 times, ultrasonic washing 30 minutes, 2 are cleaned repeatedly with distilled water It is secondary, ultrasonic washing 10 minutes, distilled water cleaning terminate after, isopropanol, acetone, methanol equal solvent in order ultrasonic washing with After dry, be transferred in plasma washing machine, by aforesaid substrate wash 5 minutes, be sent in evaporator.
Hole injection layer will be deposited on the ito transparent electrode being already prepared toHole is deposited to pass Defeated layerThe implementation of evaporation evaporation luminescent layer material of main part comparative compound 1 or the present invention above hole transmission layer Example material and dopant (piq)2Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III) Acetylacetonate] (5%) evaporationThen electron transfer layer is depositedElectron injecting layerNegative electrodeSaid process organic matter vaporization plating speed is to maintainLiF isAl is
[embodiment 6-10]
Comparative compound 1 in comparing embodiment 2 is changed into shown compound 18 in embodiment 6-10,25,26,31, 46。
Table 2 is part of compounds prepared by the embodiment of the present invention and compares the characteristics of luminescence of the luminescent device of material preparation Test result.
The characteristics of luminescence test of [table 2] luminescent device
Obviously, the explanation of above example is only intended to help the method and its core concept for understanding the present invention.It should refer to Go out, under the premise without departing from the principles of the invention, can also be to this hair for the those of ordinary skill of the technical field It is bright to carry out some improvement and modification, but these are improved and modification is also fallen into the protection domain of the claims in the present invention.

Claims (6)

1. a kind of benzo carbazole analog derivative, there is the structural formula as shown in formula (I)：
Wherein, Ar1、Ar2Independent is selected from substituted or unsubstituted C6~C60 aryl, substituted or unsubstituted C10~C60 condensed ring Base or substituted or unsubstituted C3~C60 heterocyclic radicals.
A kind of 2. benzo carbazole analog derivative according to claim 1, it is characterised in that Ar1、Ar2Independent is selected from substitution Or unsubstituted C6~C30 aryl, substituted or unsubstituted C10~C30 condensed ring radicals or substituted or unsubstituted C4~C30 heterocycles Base.
A kind of 3. benzo carbazole analog derivative according to claim 1, it is characterised in that Ar1、Ar2Independent is selected from substitution Or unsubstituted phenyl, naphthyl, anthryl, phenanthryl, xenyl, terphenyl, dibenzofuran group, dibenzothiophenes base, substitution Or unsubstituted fluorenyl, the fluorenyl of spiral shell two, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted triazine radical or substitution or do not take The carbazyl in generation.
A kind of 4. benzo carbazole analog derivative according to claim 1, it is characterised in that appointing in following compound 1-60 Shown in meaning one kind：
5. a kind of organic luminescent device, including anode, negative electrode and several organic work(between the anode and negative electrode Ergosphere, it is characterised in that at least spread out in the organic function layer containing the benzo carbazole class described in any one of Claims 1 to 4 Biology.
6. a kind of organic luminescent device according to claim 5, it is characterised in that described in any one of Claims 1 to 4 Benzo carbazole analog derivative is used as luminescent layer material of main part in an organic light emitting device.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107602440A (en) * 2017-10-09 2018-01-19 长春海谱润斯科技有限公司 A kind of benzo carbazole class electroluminescent organic material and its organic luminescent device
CN107629062A (en) * 2017-10-09 2018-01-26 长春海谱润斯科技有限公司 A kind of carbazole analog derivative and its organic luminescent device
CN107698486A (en) * 2017-10-09 2018-02-16 长春海谱润斯科技有限公司 A kind of benzo carbazole organic compound and its organic luminescent device

Citations (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106187944A (en) * 2016-07-28 2016-12-07 长春海谱润斯科技有限公司 A kind of phenothiazines and its preparation method and application
CN106220571A (en) * 2016-07-28 2016-12-14 长春海谱润斯科技有限公司 A kind of nitogen-contained heterocycle derivant and the application in organic electroluminescence device thereof
CN106279184A (en) * 2016-08-11 2017-01-04 长春海谱润斯科技有限公司 A kind of pyridazine class derivant and its preparation method and application
CN106565720A (en) * 2016-11-14 2017-04-19 长春海谱润斯科技有限公司 Aromatic amine derivative, and preparation method and application thereof
CN106588970A (en) * 2016-12-29 2017-04-26 长春海谱润斯科技有限公司 Large Pi conjugated silicozine derivative and organic light-emitting device using same
CN106632231A (en) * 2016-12-29 2017-05-10 长春海谱润斯科技有限公司 Heterocyclic derivative and organic light-emitting device using same
CN106749401A (en) * 2016-10-25 2017-05-31 长春海谱润斯科技有限公司 A kind of carbazole analog derivative and its preparation method and application
CN106749197A (en) * 2016-12-07 2017-05-31 长春海谱润斯科技有限公司 A kind of aromatic amine analog derivative and its preparation method and application
CN106749293A (en) * 2016-12-29 2017-05-31 长春海谱润斯科技有限公司 A kind of Hete rocyclic derivatives and the organic luminescent device using the Hete rocyclic derivatives
CN106749412A (en) * 2016-12-19 2017-05-31 长春海谱润斯科技有限公司 The carbazole analog derivative and the organic luminescent device using the derivative of a kind of meta phosphine oxygen groups substitution
CN106866709A (en) * 2017-03-04 2017-06-20 长春海谱润斯科技有限公司 A kind of carbazole meta connects benzothiophene derivative and its organic luminescent device
CN106905221A (en) * 2017-03-04 2017-06-30 长春海谱润斯科技有限公司 A kind of benzo fluorene kind derivative and its organic luminescent device
CN106946934A (en) * 2017-03-29 2017-07-14 长春海谱润斯科技有限公司 A kind of material of main part and organic luminescent device containing flexible chain structure
CN107216329A (en) * 2017-07-13 2017-09-29 长春海谱润斯科技有限公司 A kind of pyridoindole derivatives and processes and the organic electroluminescence device prepared using the compound
CN107235997A (en) * 2017-03-29 2017-10-10 长春海谱润斯科技有限公司 A kind of spiral shell silicon fluorene derivative and its organic luminescent device
CN107312017A (en) * 2017-07-13 2017-11-03 长春海谱润斯科技有限公司 A kind of electroluminescent organic material and its organic luminescent device of Han phenoxazines/Sai oxazine analog derivatives
CN107353284A (en) * 2017-07-13 2017-11-17 长春海谱润斯科技有限公司 A kind of pyrido benzazolyl compounds and its organic luminescent device
CN107382749A (en) * 2017-07-28 2017-11-24 长春海谱润斯科技有限公司 The aromatic amine analog derivative and its organic luminescent device of a kind of class formation containing fluorenes
CN107417702A (en) * 2017-08-22 2017-12-01 长春海谱润斯科技有限公司 A kind of novel electroluminescent organic material and organic luminescent device
CN107445955A (en) * 2017-08-22 2017-12-08 长春海谱润斯科技有限公司 A kind of preparation of aromatic amine derivatives and its organic luminescent device containing Phen structure
CN107602440A (en) * 2017-10-09 2018-01-19 长春海谱润斯科技有限公司 A kind of benzo carbazole class electroluminescent organic material and its organic luminescent device
CN107629062A (en) * 2017-10-09 2018-01-26 长春海谱润斯科技有限公司 A kind of carbazole analog derivative and its organic luminescent device
CN107698486A (en) * 2017-10-09 2018-02-16 长春海谱润斯科技有限公司 A kind of benzo carbazole organic compound and its organic luminescent device
CN108358918A (en) * 2018-04-25 2018-08-03 长春海谱润斯科技有限公司 A kind of pyrene derivatives and its organic electroluminescence device
CN108358919A (en) * 2018-04-25 2018-08-03 长春海谱润斯科技有限公司 A kind of phenanthrene derivative and its organic electroluminescence device
CN108440524A (en) * 2018-04-25 2018-08-24 长春海谱润斯科技有限公司 A kind of Sanya benzene derivative and its organic electroluminescence device

Patent Citations (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106187944A (en) * 2016-07-28 2016-12-07 长春海谱润斯科技有限公司 A kind of phenothiazines and its preparation method and application
CN106220571A (en) * 2016-07-28 2016-12-14 长春海谱润斯科技有限公司 A kind of nitogen-contained heterocycle derivant and the application in organic electroluminescence device thereof
CN106279184A (en) * 2016-08-11 2017-01-04 长春海谱润斯科技有限公司 A kind of pyridazine class derivant and its preparation method and application
CN106749401A (en) * 2016-10-25 2017-05-31 长春海谱润斯科技有限公司 A kind of carbazole analog derivative and its preparation method and application
CN106565720A (en) * 2016-11-14 2017-04-19 长春海谱润斯科技有限公司 Aromatic amine derivative, and preparation method and application thereof
CN106749197A (en) * 2016-12-07 2017-05-31 长春海谱润斯科技有限公司 A kind of aromatic amine analog derivative and its preparation method and application
CN106749412A (en) * 2016-12-19 2017-05-31 长春海谱润斯科技有限公司 The carbazole analog derivative and the organic luminescent device using the derivative of a kind of meta phosphine oxygen groups substitution
CN106588970A (en) * 2016-12-29 2017-04-26 长春海谱润斯科技有限公司 Large Pi conjugated silicozine derivative and organic light-emitting device using same
CN106632231A (en) * 2016-12-29 2017-05-10 长春海谱润斯科技有限公司 Heterocyclic derivative and organic light-emitting device using same
CN106749293A (en) * 2016-12-29 2017-05-31 长春海谱润斯科技有限公司 A kind of Hete rocyclic derivatives and the organic luminescent device using the Hete rocyclic derivatives
CN106866709A (en) * 2017-03-04 2017-06-20 长春海谱润斯科技有限公司 A kind of carbazole meta connects benzothiophene derivative and its organic luminescent device
CN106905221A (en) * 2017-03-04 2017-06-30 长春海谱润斯科技有限公司 A kind of benzo fluorene kind derivative and its organic luminescent device
CN106946934A (en) * 2017-03-29 2017-07-14 长春海谱润斯科技有限公司 A kind of material of main part and organic luminescent device containing flexible chain structure
CN107235997A (en) * 2017-03-29 2017-10-10 长春海谱润斯科技有限公司 A kind of spiral shell silicon fluorene derivative and its organic luminescent device
CN107216329A (en) * 2017-07-13 2017-09-29 长春海谱润斯科技有限公司 A kind of pyridoindole derivatives and processes and the organic electroluminescence device prepared using the compound
CN107312017A (en) * 2017-07-13 2017-11-03 长春海谱润斯科技有限公司 A kind of electroluminescent organic material and its organic luminescent device of Han phenoxazines/Sai oxazine analog derivatives
CN107353284A (en) * 2017-07-13 2017-11-17 长春海谱润斯科技有限公司 A kind of pyrido benzazolyl compounds and its organic luminescent device
CN107382749A (en) * 2017-07-28 2017-11-24 长春海谱润斯科技有限公司 The aromatic amine analog derivative and its organic luminescent device of a kind of class formation containing fluorenes
CN107445955A (en) * 2017-08-22 2017-12-08 长春海谱润斯科技有限公司 A kind of preparation of aromatic amine derivatives and its organic luminescent device containing Phen structure
CN107417702A (en) * 2017-08-22 2017-12-01 长春海谱润斯科技有限公司 A kind of novel electroluminescent organic material and organic luminescent device
CN107602440A (en) * 2017-10-09 2018-01-19 长春海谱润斯科技有限公司 A kind of benzo carbazole class electroluminescent organic material and its organic luminescent device
CN107629062A (en) * 2017-10-09 2018-01-26 长春海谱润斯科技有限公司 A kind of carbazole analog derivative and its organic luminescent device
CN107698486A (en) * 2017-10-09 2018-02-16 长春海谱润斯科技有限公司 A kind of benzo carbazole organic compound and its organic luminescent device
CN108358918A (en) * 2018-04-25 2018-08-03 长春海谱润斯科技有限公司 A kind of pyrene derivatives and its organic electroluminescence device
CN108358919A (en) * 2018-04-25 2018-08-03 长春海谱润斯科技有限公司 A kind of phenanthrene derivative and its organic electroluminescence device
CN108440524A (en) * 2018-04-25 2018-08-24 长春海谱润斯科技有限公司 A kind of Sanya benzene derivative and its organic electroluminescence device

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107602440A (en) * 2017-10-09 2018-01-19 长春海谱润斯科技有限公司 A kind of benzo carbazole class electroluminescent organic material and its organic luminescent device
CN107629062A (en) * 2017-10-09 2018-01-26 长春海谱润斯科技有限公司 A kind of carbazole analog derivative and its organic luminescent device
CN107698486A (en) * 2017-10-09 2018-02-16 长春海谱润斯科技有限公司 A kind of benzo carbazole organic compound and its organic luminescent device

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