CN108358918A - A kind of pyrene derivatives and its organic electroluminescence device - Google Patents

A kind of pyrene derivatives and its organic electroluminescence device Download PDF

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Publication number
CN108358918A
CN108358918A CN201810378387.2A CN201810378387A CN108358918A CN 108358918 A CN108358918 A CN 108358918A CN 201810378387 A CN201810378387 A CN 201810378387A CN 108358918 A CN108358918 A CN 108358918A
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pyrene derivatives
unsubstituted
substituted
organic
electroluminescence device
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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

A kind of pyrene derivatives of present invention offer and its organic electroluminescence device, belong to organic photoelectrical material technical field.The compound has structure shown in formula (I), and the present invention condenses pyrene and benzimidazole, so as to get material have the function of excellent electron transport ability and high glass-transition temperature and can prevent from crystallizing；Synthetic method is simple to operation, and the organic luminescent device prepared using the pyrene derivatives shows the advantage that driving voltage is low, luminous efficiency is high, is the luminous organic material of function admirable.

Description

A kind of pyrene derivatives and its organic electroluminescence device
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to a kind of pyrene derivatives and its organic electroluminescence Part.
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 it) involves great expense, resolution ratio is not high, power consumption is big.
Organic electroluminescent LED (organic light-emitting diodes, OLEDs) is as a kind of completely new Display technology possesses the unmatched advantage of existing display technology in each performance, such as have it is all solid state, from main light emission, brightness Height, high-resolution, visual angle wide (170 degree or more), 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 very extensive, such as illuminates System, communication system, car-mounted display, portable electronic device, fine definition show even military field.
Electroluminescent organic material is constantly realized in recent years to be 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 at Fruit, but OLED also has some urgent problems to be solved during commercialized.
Luminescent material is divided into fluorescent material and phosphor material, and the forming method of luminescent layer is that phosphorus is adulterated in fluorescent host material The method of method and fluorescent host material doping fluorescent (organic matter for including nitrogen) dopant of luminescent material (organic metal).It is common Material of main part can generally be divided into several, such as hole transport material of main part, electron-transport material of main part, bipolar material of main part, lazy Property material of main part, fluorescence complex material of main part and phosphorescent complexes material of main part.
In the organic luminescent device prepared using phosphor material, worked as mostly containing trianilino group material using TPD etc. Make the main body luminescent material of luminescent layer.However, the thermal stability of this kind of material is poor, lead to organic hair using phosphor material The service life of optical device is shorter, thus reduces the usage degree of such material.The better material of new performance how is designed to carry out It adjusts, is always those skilled in the art's urgent problem to be solved.
Invention content
The object of the present invention is to provide a kind of pyrene derivatives and its organic electroluminescence device, the present invention passes through to pyrene and benzene And imidazoles is condensed, so as to get material have the function of high glass-transition temperature and can prevent crystallization.By the change It closes object to use and manufactured organic electroluminescence device as the material of main part in luminescent layer, it is low, luminous to show driving voltage Efficient advantage is the luminous organic material of function admirable.
Present invention firstly provides a kind of pyrene derivatives, structural formula is：
Wherein, R1、R2It is independent selected from hydrogen, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6-C60 Aryl, substituted or unsubstituted C3~C60 heteroaryl in one kind.
Preferably, the R1、R2It is independent selected from hydrogen, it is substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted The aryl of C6-C30, substituted or unsubstituted C4~C30 heteroaryl in one kind.
Preferably, the R1、R2It is independent to be selected from hydrogen, C1~C4 alkyl or substituted or unsubstituted following group：Benzene Base, naphthalene, anthryl, phenanthryl, pyrenyl, xenyl, terphenyl, fluorenyl, 9-9 dimethyl fluorenes, 9-9 diphenylfluorenes, two fluorenyl of spiral shell, Carbazyl, pyridyl group, acridinyl, phenothiazinyl, phenoxazine groups, triazine radical, dibenzothiophene, dibenzofuran group, quinoline Base or isoquinolyl.
Preferably, any one of the pyrene derivatives in structure as follows：
。
The present invention also provides a kind of organic electroluminescence device, including anode, cathode and positioned at the anode with it is described Several organic function layers between cathode, the organic function layer include the pyrene derivatives any one or at least two The combination of kind.
Preferably, the organic function layer includes luminescent layer, and the luminescent layer includes any one of the pyrene derivatives Kind or at least two combination.
Preferably, the pyrene derivatives are used as material of main part in luminescent layer.
Beneficial effects of the present invention：
For the problems such as thermal stability for solving phosphorescent light body material in the prior art is poor, and service life is short, the present invention A kind of derivative containing pyrene and benzimidazole structure is provided first, which has structure shown in formula (I).The present invention is by pyrene It is condensed with benzimidazole, and pyrene and benzimidazole is replaced with alkyl, aryl, heteroaryl, improve main body material The electronic transmission performance of material so that the material is efficient in terms of electron-transport, can improve the current characteristics of device so that To material have the function of high glass-transition temperature and can prevent crystallization.Using the compound as the master in luminescent layer Body materials'use and manufactured organic electroluminescence device, show the advantage that driving voltage is low, luminous efficiency is high, are that performance is excellent Good luminous organic material.
Specific implementation mode
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 only the feature and advantage further illustrated the present invention, rather than to the claims in the present invention Limitation.
It should be noted that unless otherwise prescribed, the meaning of scientific and technical terminology used in the present invention and people in the art The meaning that member is generally understood is identical.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane Base, branched alkyl or naphthenic base, example may include methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl group, sec-butyl, tertiary fourth Base, amyl, isopentyl, cyclopenta, cyclohexyl etc., but not limited to this.
Aryl of the present invention refer to aromatic hydrocarbon molecule aromatic core carbon on remove a hydrogen atom after, be left univalent perssad it is total Claiming, can be monocyclic aryl or fused ring aryl, example may include phenyl, xenyl, naphthalene, anthryl, phenanthryl or pyrenyl etc., but It is without being limited thereto.
Heteroaryl of the present invention refers to the total of the group that one or more aromatic core carbon are substituted by hetero atom in aryl Claim, the hetero atom includes but not limited to oxygen, sulphur, nitrogen or silicon atom, and the heteroaryl can be monocycle or condensed ring, and example can wrap Include pyridyl group, phenothiazinyl, phenoxazine base, pyrimidine radicals, benzo pyrimidine radicals, carbazyl, triazine radical, benzothiazolyl, benzo miaow Oxazolyl, acridinyl etc., but not limited to this.
In substituted alkyl of the present invention, substituted aryl, substituted heteroaryl, the substituent group independent can select From D-atom, cyano, nitro, halogen atom, the alkyl of C1-C10, the alkoxy of C1-C10, the alkylthio group of C1-C10, C1-C30 Aryl, the aryloxy group of C1-C30, the arylthio of C1-C30, C3-C30 heteroaryl, the silylation of C1~C30, C2~C10 The aryl amine etc. of alkylamino radical, C6~C30, such as D-atom, cyano, nitro, halogen, methyl, ethyl, propyl, isopropyl, tertiary fourth Base, methoxyl group, methyl mercapto, phenyl, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, benzo phenanthryl, base, pyrenyl, fluorenyl, 9,9- dimethyl fluorenyl, benzyl, phenoxy group, thiophenyl, hexichol amido, dimethylamino, carbazyl, 9- phenyl carbazoles base, furan It mutters base, thienyl, triphenyl silicon substrate, trimethyl silicon substrate, trifluoromethyl, phenothiazinyl, phenoxazine group, acridinyl, piperidyl, pyrrole Piperidinyl, pyrazinyl, triazine radical, pyrimidine radicals etc., but not limited to this.
Present invention firstly provides a kind of pyrene derivatives, have the structural formula as shown in formula (I)：
Wherein, R1、R2It is independent selected from hydrogen, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6-C60 Aryl, substituted or unsubstituted C3~C60 heteroaryl in one kind.
According to the present invention, preferably R1、R2It is independent to be selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substitution or unsubstituted The aryl of C6-C30, one kind in the heteroaryl of substituted or unsubstituted C4~C30.
According to the present invention, preferably R1、R2It is independent to be selected from hydrogen, C1~C4 alkyl or substituted or unsubstituted following group：Benzene Base, naphthalene, anthryl, phenanthryl, pyrenyl, xenyl, terphenyl, fluorenyl, two fluorenyl of spiral shell, carbazyl, pyridyl group, acridinyl, pheno Thiazinyl, phenoxazine groups, triazine radical, dibenzothiophene, dibenzofuran group, quinolyl or isoquinolin
Specifically, the pyrene derivatives are preferably selected from such as any one in lower structure：
。
Some specific structure types of pyrene derivatives of the present invention are enumerated above, but the invention is not limited in institutes These chemical constitutions of row, every based on structure shown in formula (I), R1、R2It should be all included in for group as defined above It is interior.
Phenanthrene derivative of the present invention, preparation method are as follows：
According to the present invention, intermediate A is prepared according to method as follows：
Under the protection of nitrogen, compound a and compound b, with Pd (PPh3)4As catalyst, C-C coupling reactions occur Compound c is generated, using sodium tert-butoxide, palladium, tri-tert-butylphosphine as catalyst, it is even that C-N occurs for compound c and compound d Connection reaction generates intermediate A.
According to the present invention, compound I is prepared according to method as follows：
Intermediate A is dissolved in the water, by PhI (OAc)2, mCPBA and PTSA.H2O is added in above-mentioned solution, stirs to anti- Should be complete, obtain compound I.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device is those skilled in the art Known organic electroluminescence device, organic electroluminescence device of the present invention include anode, cathode and are located at Several organic function layers between the anode and cathode, the organic function layer include that the phenanthrene derivative is any one Kind or at least two combination.The organic function layer may include hole injection layer, hole transmission layer, electronic barrier layer, hair At least one layer in photosphere, hole blocking layer, electron transfer layer and electron injecting layer, the preferably described organic function layer include shining Layer, the luminescent layer include the pyrene derivatives any one or at least two combination.The more preferable pyrene derivatives It is used as material of main part in luminescent layer.
The present invention is not particularly limited the source of the raw material employed in following embodiment, can be commercial product or It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1：
The preparation of compound 2
The preparation of intermediate 2-3
Under the protection of nitrogen, the addition 2-1 (36.00g, 100.00mmol) into 2L reaction kettles, 2-2 (12.20g, 100.00mmol), potassium carbonate (1.24g, 9.00mmol), toluene 200mL stirrings.Reactor temperature is raised to 70 DEG C, and Pd is added (PPh3)4(1.04g, 0.90mmol), distilled water 100mL stirrings, is stirred at reflux 11h, fully reacts.It is whole that 70mL distilled water is added It after only reacting, is filtered under diminished pressure, is washed with distilled water solid, acetone, toluene, THF is then used to recrystallize, risen again after obtaining solid China, re crystallization from toluene obtain intermediate 2-3 28.69g, yield 80.32%.
The preparation of intermediate 2-5
By tri-tert-butylphosphine (toluene solution of the 1.0M of 4.4mL, 1.48g, 0.05mmol), palladium (0.4g, 1.83mmol) and sodium tert-butoxide (52.7g, 549mmol) be added to 2-3 (28.69g, 80.31mmol) and 2-4 (7.56g, 80.31mmol) the solution in degassed toluene (500mL), and the mixture is heated 2 hours under reflux.By the reaction Mixture is cooled to room temperature, and is filtered with dilution with toluene and via diatomite.The filtrate water is diluted, toluene is used in combination to extract, And merges organic phase, it is evaporated under vacuum.The residue was carried out via silica gel (heptane/dichloromethane) Filter, and crystallized from isopropanol, obtain intermediate 2-5 23.39g, yield 78.63%.
The preparation of compound 2
2-5 (23.39g, 63.13mmol) is dissolved in 1L water, by PhI (OAc)2(1.87g, 5.8mmol), mCPBA (10equiv, 2.9mmol) and PTSA.H2O (20equiv, 5.88mmol) is added in above-mentioned solution, and room temperature lower open mouth is in air In be sufficiently stirred 4-6h, TLC monitorings are complete until reactant reaction, and reaction solution is extracted with ethyl acetate, with saturation sulphur Sodium thiosulfate solution washed product, organic layer is washed with saturated brine, and is dried with anhydrous sodium sulfate, to organic extract into Row decompression filters, and is recrystallized to give 217.60g, yield 75.65%.Mass spectrum m/z：368.44 (calculated values：368.45).It is theoretical Constituent content (%) C27H16N2：C, 88.02；H, 4.38；N, 7.60 actual measurement constituent contents (%)：C, 88.03；H, 4.37；N, 7.59.It is target product 2 that above-mentioned confirmation, which obtains product,.
Embodiment 2
The preparation of compound 12
2-2 in embodiment 1 is replaced with into 12-2 as shown above, obtains compound 12.Mass spectrum m/z：458.52 (calculate Value：458.53).Theoretical elemental content (%) C33H18N2O：C, 86.44；H, 3.96；N, 6.11；O, 3.49 actual measurement constituent contents (%)：C, 86.45；H, 3.97；N, 6.12；O, 3.48.It is target product 12 that above-mentioned confirmation, which obtains product,.
Embodiment 3
The preparation of compound 19
2-2 in embodiment 1 is replaced with into 19-2 as shown above, 2-4 replaces with 19-4 as shown above, obtains compound 19.Mass spectrum m/z：533.63 (calculated values：533.64).Theoretical elemental content (%) C39H23N3：C, 87.78；H, 4.34；N, 7.87 Survey constituent content (%)：C, 87.79；H, 4.35；N, 7.86.It is target product 19 that above-mentioned confirmation, which obtains product,.
Embodiment 4
The preparation of compound 28
2-2 in embodiment 1 is replaced with into 28-2 as shown above, 2-4 replaces with 28-4 as shown above, obtains compound 28.Mass spectrum m/z：561.64 (calculated values：561.65).Theoretical elemental content (%) C40H23N3O：C, 85.54；H, 4.13；N, 7.48；O, 2.85 actual measurement constituent contents (%)：C, 85.53；H, 4.14；N, 7.47；O, 2.86.It is mesh that above-mentioned confirmation, which obtains product, Mark product 28.
Embodiment 5
The preparation of compound 33
2-2 in embodiment 1 is replaced with into 33-2 as shown above, 2-4 replaces with 33-4 as shown above, obtains compound 33.Mass spectrum m/z：544.66 (calculated values：544.67).Theoretical elemental content (%) C41H24N2：C, 90.41；H, 4.44；N, 5.14 Survey constituent content (%)：C, 90.42；H, 4.43；N, 5.12.It is target product 33 that above-mentioned confirmation, which obtains product,.
Embodiment 6
The preparation of compound 48
2-2 in embodiment 1 is replaced with into 48-2 as shown above, 2-4 replaces with 48-4 as shown above and obtains compound 48. Mass spectrum m/z：625.73 (calculated values：625.74).Theoretical elemental content (%) C45H27N3O：C, 86.38；H, 4.35；N, 6.72； O, 2.56 actual measurement constituent contents (%)：C, 86.39；H, 4.36；N, 6.73；O, 2.57.Above-mentioned confirmation obtains product and is produced for target Object 48.
Embodiment 7
The preparation of compound 67
2-2 in embodiment 1 is replaced with into 67-2 as shown above, 2-4 replaces with 67-4 as shown above, obtains compound 67.Mass spectrum m/z：734.90 (calculated values：734.91).Theoretical elemental content (%) C56H34N2：C, 91.52；H, 4.66；N, 3.81 Survey constituent content (%)：C, 91.53；H, 4.65；N, 3.82.It is target product 67 that above-mentioned confirmation, which obtains product,.
Embodiment 8
The preparation of compound 86
2-2 in embodiment 1 is replaced with into 86-2 as shown above, 2-4 replaces with 86-4 as shown above and obtains compound 86. Mass spectrum m/z：650.75 (calculated values：650.76).Theoretical elemental content (%) C45H26N6：C, 83.06；H, 4.03；N, 12.91 is real Survey constituent content (%)：C, 83.07；H, 4.04；N, 12.92.It is target product 86 that above-mentioned confirmation, which obtains product,.
[comparison Application Example]
Transparent anode electrode ito substrate is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, is then existed It is cleaned 2 minutes in plasma cleaning device, dry and is evacuated to 5 × 10-5Pa.Then by treated, ito substrate steams Plating.One layer of HAT-CN is deposited first as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 10nm.Followed by it sends out The luminous organic material CBP/Ir (ppy) is deposited in the vapor deposition of photosphere, mixing3, as green light phosphorescence dopant material, doping concentration It is 5%, evaporation rate 0.005nm/s, evaporation thickness 30nm are then deposited the TPBI of 50nm as electron transfer layer, steam Plating rate is 0.01nm/s, is used as cathode, thickness 30nm for vacuum evaporation Al layers on the electron transport layer.
[Application Example 1-8]
Transparent anode electrode ito substrate is cleaned each 15 minutes with deionized water, acetone, EtOH Sonicate respectively, is then existed It is cleaned 2 minutes in plasma cleaning device, dry and is evacuated to 5 × 10-5Pa, then by treated, ito substrate steams Plating.One layer of HAT-CN is deposited first as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness 10nm.Followed by it sends out Pyrene derivatives/Ir (ppy) of the present invention is deposited in the vapor deposition of photosphere, mixing3, as green light phosphorescence dopant material, doping concentration It is 5%, the TPBI of the 50nm of 50nm is then deposited as electron-transport in evaporation rate 0.005nm/s, evaporation thickness 30nm Layer, evaporation rate 0.01nm/s are used as cathode, thickness 30nm for vacuum evaporation Al layers on the electron transport layer.The above method The electron luminescence characteristic of the organic luminescent device of manufacture indicates in the following table：
The above result shows that the compound of the present invention is applied to organic electroluminescence device as luminescent layer material of main part 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 Defined by the case of spirit and scope of the invention, those of ordinary skill in the art can carry out various forms and details to it On change.

Claims (7)

1. a kind of pyrene derivatives, which is characterized in that have structure shown in following general formula (I)：
Wherein, R1、R2The independent virtue selected from hydrogen, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6-C60 Base, substituted or unsubstituted C3-C60 heteroaryl in one kind.
2. pyrene derivatives according to claim 1, which is characterized in that R1、R2It is independent to be selected from hydrogen, substituted or unsubstituted C1- C30 alkyl, the aryl of substituted or unsubstituted C6-C30, substituted or unsubstituted C4-C30 heteroaryl in one kind.
3. pyrene derivatives according to claim 1, which is characterized in that R1、R2It is independent selected from hydrogen, C1-C4 alkyl or substitution or Unsubstituted following group：Phenyl, naphthalene, anthryl, phenanthryl, pyrenyl, xenyl, terphenyl, fluorenyl, 9-9 dimethyl fluorenes, 9- 9 diphenylfluorenes, two fluorenyl of spiral shell, carbazyl, pyridyl group, acridinyl, phenothiazinyl, phenoxazine groups, triazine radical, dibenzothiophenes Base, dibenzofuran group, quinolyl or isoquinolyl.
4. pyrene derivatives according to claim 1, which is characterized in that any one in structure as follows：
5. a kind of organic electroluminescence device, including anode, cathode and several between the anode and the cathode A organic function layer, which is characterized in that the organic function layer includes Claims 1 to 4 any one of them pyrene derivatives Any one or at least two combination.
6. a kind of organic electroluminescence device according to claim 5, which is characterized in that the organic function layer includes hair Photosphere, the luminescent layer include Claims 1 to 4 any one of them pyrene derivatives any one or at least two group It closes.
7. a kind of organic electroluminescence device according to claim 6, which is characterized in that the pyrene derivatives are in luminescent layer In be used as material of main part.
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Cited By (6)

* 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
CN107698488A (en) * 2017-10-09 2018-02-16 长春海谱润斯科技有限公司 A kind of benzo carbazole analog derivative and its organic luminescent 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

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100099459A (en) * 2009-03-03 2010-09-13 덕산하이메탈(주) Bis(benzoimidazole) chemiclal and organic electroric element using the same, terminal thererof
WO2012079032A2 (en) * 2010-12-09 2012-06-14 Trana Discovery, Inc. Compositions and methods of treating drug-resistant retroviral infections
JP2012204794A (en) * 2011-03-28 2012-10-22 Sony Corp Organic electroluminescent element and display device
CN106467549A (en) * 2016-08-03 2017-03-01 江苏三月光电科技有限公司 A kind of compound containing benzimidazole and its application on 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
CN108440525A (en) * 2018-04-25 2018-08-24 长春海谱润斯科技有限公司 A kind of 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
CN108530469A (en) * 2018-05-29 2018-09-14 长春海谱润斯科技有限公司 A kind of and fluorene compound and its organic electroluminescence device
CN108530336A (en) * 2018-05-29 2018-09-14 长春海谱润斯科技有限公司 A kind of and fluorene compound and its organic electroluminescence device
CN108727260A (en) * 2018-05-29 2018-11-02 长春海谱润斯科技有限公司 A kind of and fluorene derivative and its organic electroluminescence device
CN108727252A (en) * 2018-05-29 2018-11-02 长春海谱润斯科技有限公司 A kind of and fluorene compound and its organic electroluminescence device

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20100099459A (en) * 2009-03-03 2010-09-13 덕산하이메탈(주) Bis(benzoimidazole) chemiclal and organic electroric element using the same, terminal thererof
WO2012079032A2 (en) * 2010-12-09 2012-06-14 Trana Discovery, Inc. Compositions and methods of treating drug-resistant retroviral infections
JP2012204794A (en) * 2011-03-28 2012-10-22 Sony Corp Organic electroluminescent element and display device
CN106467549A (en) * 2016-08-03 2017-03-01 江苏三月光电科技有限公司 A kind of compound containing benzimidazole and its application on 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
CN108440525A (en) * 2018-04-25 2018-08-24 长春海谱润斯科技有限公司 A kind of 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
CN108530469A (en) * 2018-05-29 2018-09-14 长春海谱润斯科技有限公司 A kind of and fluorene compound and its organic electroluminescence device
CN108530336A (en) * 2018-05-29 2018-09-14 长春海谱润斯科技有限公司 A kind of and fluorene compound and its organic electroluminescence device
CN108727260A (en) * 2018-05-29 2018-11-02 长春海谱润斯科技有限公司 A kind of and fluorene derivative and its organic electroluminescence device
CN108727252A (en) * 2018-05-29 2018-11-02 长春海谱润斯科技有限公司 A kind of and fluorene compound and its organic electroluminescence device

Cited By (6)

* 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
CN107698488A (en) * 2017-10-09 2018-02-16 长春海谱润斯科技有限公司 A kind of benzo carbazole analog derivative and its organic luminescent 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

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