CN104629731B - Organic compound and the application in electroluminescent device thereof - Google Patents
Organic compound and the application in electroluminescent device thereof Download PDFInfo
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Abstract
The present invention relates to a kind of electroluminescent organic material and preparation method thereof, solve the technical problem that the luminous efficiency of existing luminescent material still can not meet the requirement of OLED.Electroluminescent organic material is to be connected on Phen base by substituted thiazolyl group, shows high electron mobility；The regularity of molecular stacks can be increased with molecular configurational symmetry, improve current-carrying electrons mobility the most to a certain extent, be more beneficial for during vacuum evaporation being formed all and non-crystalline film.The compound of the present invention at room temperature has higher stability, and the device applied also has higher stability.
Description
Technical field
The present invention relates to a kind of novel organic material, and the application in ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field.
Background technology
As a rule, electron transport material all has the plane aromatic compound of big conjugated structure, and they have mostly
Have and preferably connect nucleophobic ability, under certain forward bias, can effectively transmit again electronics, the property being currently known simultaneously
Electron transport material that can be good is the most few, is currently available that electron transport material mainly has 8-hydroxyquinoline aluminium compounds,
Furodiazole compound, quinoxaline compound, the polymer of nitrile group-containing, other nitrogen-containing heterocycle compound etc..
Therefore to design an electron transport material that organic electroluminescence device efficiency can be made to be obviously improved, need to possess with
Lower character: (1) has reversible electrochemical reduction and enough high also original units；(2) need suitable HOMO and LUMO and make electricity
Son has the injection energy gap of minimum, to reduce initial and operation voltage；(3) higher electron mobility is needed；(4) had
Glass transition temperature and heat endurance；(5) there is noncrystalline film.
Summary of the invention
The invention provides a kind of containing benzothiazolyl phenanthrene quinoline compounds.This compound structure is symmetrical, prepares work
Skill is simple, has higher luminous efficiency and high carrier mobility, can be used for the electron transfer layer of electroluminescent cell.Institute
The device of application can significantly reduce driving voltage, improves current efficiency.
Technical scheme is as follows,
A kind of benzothiazolyl phenanthrene quinoline compounds, wherein, the molecule of described benzothiazolyl phenanthrene quinoline compounds
General structure such as following formula (1):
... ... ... .(1)
In formula (1):
R1、R2And R3Independently selected from formula (2) or the aromatic radical of (3) 5 ~ 60 carbon atoms containing benzothiazole group
Group.
... ... ... (2)
... ... ... ..(3)
Wherein, preferably R4And R5Selected from hydrogen atom, or selected from carbon atom number from 1 ~ 6 alkyl and alkoxyl.
More preferably work as R1During for formula (2), R4For nothing, R5For hydrogen atom；
Work as R1During for formula (3), R4For nothing；
Work as R1During for formula (2), R4For nothing, R5For phenyl；
Work as R1During for formula (2), R4For phenyl, R5For nothing；
Work as R2During for formula (2), R4For nothing, R5For hydrogen atom；
Work as R2During for formula (3), R4For nothing；
Work as R2During for formula (2), R4For nothing, R5For phenyl；
Work as R2During for formula (2), R4For phenyl, R5For nothing；
Work as R3During for formula (2), R4For nothing, R5For hydrogen atom；
Work as R3During for formula (3), R4For nothing；
Work as R3During for formula (2), R4For nothing, R5For phenyl；
Work as R3During for formula (2), R4For phenyl, R5For nothing.
In order to of the present invention compound is better described, we illustrate the preferred structure formula of formula of the present invention (1)
Compound 001 ~ 012, as follows:
It is above the molecular structural formula of some particular compound, but benzothiazolyl phenanthrene quinoline class provided by the present invention
Luminous organic material is not limited to the compound shown in listed molecular structural formula, every R1And R2The substituted benzothiazolyl of base
Luxuriant and rich with fragrance quinoline class series compound is included in benzothiazolyl phenanthrene quinoline class luminous organic material provided by the present invention.
The present invention also provides for the preparation method of described benzothiazolyl phenanthrene quinoline class luminous organic material, this preparation method
Concrete steps and condition as follows:
Weighing bromo benzothiazole amine phenanthroline and the boric acid containing R substituent for 2:1 in molar ratio, mol ratio is 1:
1.25:0.04 weighs phenyl boric acid, potassium carbonate and tetrakis triphenylphosphine palladium, and solvent is toluene and water, and described ratio is toluene: water is
2:1, is warmed up to 100 DEG C, reacts 20 hours, cooling, suction filtration, and ethanol is washed, separatory, column chromatography, and recrystallization obtains benzothiazolyl
Luxuriant and rich with fragrance quinoline compounds.
Beneficial effects of the present invention:
The benzothiazolyl phenanthrene quinoline compounds that the present invention prepares, from the point of view of compound structure with character relation,
The reduction potential of heterocyclic compound is lower than the pure aromatic series of analog structure, is conducive to accepting electronics, thus shows preferably
Electronic transport property.Phen analog derivative has preferable conjugate planes and relatively low HOMO energy level, and therefore we will take
The thiazolyl group in generation is connected on Phen base, can show high electron mobility；Can with molecular configurational symmetry
To increase the regularity of molecular stacks, improve current-carrying electrons mobility the most to a certain extent.Phenyl thiazole base, xenyl thiophene
The nonplanarity of oxazolyl or naphthyl benzothiazolyl so that this compounds has a certain degree of distortion on space multistory,
Be more beneficial for during vacuum evaporation being formed all and non-crystalline film.The compound of the present invention at room temperature has higher stablizing
Property, the device applied also has higher stability.
Detailed description of the invention
The present invention can be explained in more detail by following example rather than wish that the present invention is limited and this.
Compou nd synthesis embodiment:
Various chemicals such as Phen, tert-butyl lithium used by the present invention, 1,3-benzothiazole ylboronic acid, 6-benzene
Base benzothiazole, 2-(4-bromophenyl) the basic chemical industry raw material such as benzothiazole, benzothiazole all can at home Chemical market convenient
Having bought, remaining several important intermediate can synthesize by following method:
1, aphthothiazoles ylboronic acid
Under nitrogen protection, aphthothiazoles (18.5,0.1mol) is dissolved in 300mL through being dried that Na/ benzophenone processed
Oxolane, liquid nitrogen cools down, and stirring is lower is successively slowly added dropwise 40mL butyl lithium (0.1mol, 2.5mol L-1), after stirring 1.5h,
Dropping NBS(0.11mol), after dripping, react 10min, be slowly increased to room temperature reaction 2h, use NaHSO3Decolouring, product is used
200mL ether extracts three times, merges organic phase, anhydrous MgSO4Being dried, rotation is evaporated off solvent, and thick product is pure through column chromatography method
Change, obtain 2-bromine aphthothiazoles 19.2g product and put into next step reaction.1L nitrogen protection under, by previous step product (13.2g,
0.05mol) being dissolved in the dry tetrahydrofuran that 200mL processed through Na/ benzophenone, liquid nitrogen cools down, and stirring is lower the most slowly drips
Add 20mL butyl lithium (0.05mol, 2.5mol L-1), three isopropoxies borate 30mL (0.243mol), after finishing, stir naturally
Mix and be warmed to room temperature.Adding the hydrolysis of 200mL diluted hydrochloric acid aqueous solution, ethyl acetate extracts, and merges organic layer, and rotation is evaporated off solvent, produces
Thing puts into next step reaction.
2, the synthesis of 6,6-phenylbenzothiazol-2-boric acid
Under nitrogen protection, 6-phenylbenzothiazol (21.1g, 0.1mol) is dissolved in 300mL and processed through Na/ benzophenone
Dry tetrahydrofuran, liquid nitrogen cools down, and stirring is lower is successively slowly added dropwise 40mL butyl lithium (0.1mol, 2.5mol L-1), stirring
After 1.5h, drip NBS(0.11mol), after dripping, react 10min, be slowly increased to room temperature reaction 2h, use NaHSO3Decolouring,
Product 200mL ether extracts three times, merges organic phase, anhydrous MgSO4Being dried, rotation is evaporated off solvent, and thick product is through column chromatography
Method purifies, and obtains 2-bromo-6-phenylbenzothiazol 20.5g product and puts into next step reaction.Under nitrogen protection, previous step is produced
Thing (13.2g, 0.05mol) is dissolved in the dry tetrahydrofuran that 200mL processed through Na/ benzophenone, and liquid nitrogen cools down, and stirring is lower first
After be slowly added dropwise 20mL butyl lithium (0.05mol, 2.5mol L-1), three isopropoxies borate 30mL (0.243mol), finish
After, stirring is warmed to room temperature naturally.Adding the hydrolysis of 200mL diluted hydrochloric acid aqueous solution, ethyl acetate extracts, and merges organic layer, and rotation is evaporated off
Solvent, product is gone to put into next step reaction.
3, the synthesis of 4,7-benzothiazolyl phenyl boric acid
Under nitrogen protection, by 2-(4-bromophenyl) benzothiazole (14.5g, 0.05mol) is dissolved in 200mL through Na/ hexichol first
The dry tetrahydrofuran that ketone processed, liquid nitrogen cools down, and stirring is lower is successively slowly added dropwise 20mL butyl lithium (0.05mol, 2.5mol
L-1), three isopropoxies borate 30mL (0.243mol), after finishing, stirring is warmed to room temperature naturally.Add 200mL watery hydrochloric acid water
Solution hydrolyzes, and ethyl acetate extracts, and merges organic layer, and rotation is evaporated off solvent, and product puts into next step reaction.
The synthesis of embodiment 1 compound 001
By 4,7-dibromo-o phenanthroline (3.38g, 0.01mol), 1,3-benzothiazole ylboronic acid (6.37g,
0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, add
50mL concentration of potassium carbonate is 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three
Secondary and use anhydrous Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, obtain white crystalline solid 3.84g, produce
Rate 86%, HPLC purity is more than 99%.Mass spectrum: calculated value is 446.55；Test value is 446.55.Elementary analysis: calculated value is C:
69.93%；H:3.16%；N:12.55%；S:14.36%；Test value is C:69.92%；H:3.15%；N:12.56%；S:14.37%；
The synthesis of embodiment 2 compound 20 02
By 4,7-dibromo-o phenanthroline (3.38g, 0.01mol), aphthothiazoles ylboronic acid (5.73g, 0.025mol) and
Tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, adds 50mL concentration of potassium carbonate
For 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, wash three times and organic phase with anhydrous
Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 4.54g, productivity 83%,
HPLC purity is more than 99%.Mass spectrum: calculated value is 546.66；Test value is 546.66.Elementary analysis: calculated value is C:74.70%；
H:3.32%；N:10.25%；S:11.73%；Test value is C:74.70%；H:3.33%；N:10.25%；S:11.72%；
The synthesis of embodiment 3 compound 003
By 4,7-dibromo-o phenanthroline (3.38g, 0.01mol), 6-phenylbenzothiazol ylboronic acid (6.38g,
0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, add
50mL concentration of potassium carbonate is 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three
Secondary and dried by anhydrous Na 2SO4, through dichloromethane/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 5.09g,
Productivity 85%, HPLC purity is more than 99%.Mass spectrum: calculated value is 598.74；Test value is 598.75.Elementary analysis: calculated value is
C:74.70%；H:3.32%；N:10.25%；S:11.73%；Test value is C:74.70%；H:3.34%；N:10.25%；S:
11.71%；
The synthesis of embodiment 4 compound 004
By 4,7-dibromo-o phenanthroline (3.38g, 0.01mol), 7,4-benzothiazolyl phenyl boric acids (6.38g,
0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, add
50mL concentration of potassium carbonate is 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three
Secondary and use anhydrous Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 5.13g,
Productivity 86%, HPLC purity is more than 99%.Mass spectrum: calculated value is 598.74；Test value is 598.73.Elementary analysis: calculated value is
C:74.70%；H:3.32%；N:10.25%；S:11.73%；Test value is C:74.71%；H:3.31%；N:10.24%；S:
11.74%；
The synthesis of embodiment 5 compound 005
By 3,8-dibromo-o phenanthroline (3.38g, 0.01mol), 1,3-benzothiazole ylboronic acid (6.37g,
0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, add
50mL concentration of potassium carbonate is 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three
Secondary and use anhydrous Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, white crystalline solid 3.8g, productivity are obtained
85%, HPLC purity is more than 99%.Mass spectrum: calculated value is 446.55；Test value is 446.57.Elementary analysis: calculated value is C:
69.93%；H:3.16%；N:12.55%；S:14.36%；Test value is C:69.93%；H:3.18%；N:12.53%；S:14.36%；
The synthesis of embodiment 6 compound 006
By 3,8-dibromo-o phenanthroline (3.38g, 0.01mol), aphthothiazoles ylboronic acid (5.73g, 0.025mol) and
Tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, adds 50mL concentration of potassium carbonate
For 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, wash three times and organic phase with anhydrous
Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 4.49g, productivity 82%,
HPLC purity is more than 99%.Mass spectrum: calculated value is 546.66；Test value is 546.65.Elementary analysis: calculated value is C:74.70%；
H:3.32%；N:10.25%；S:11.73%；Test value is C:74.71%；H:3.33%；N:10.24%；S:11.72%；
The synthesis of embodiment 7 compound 007
By 3,8-dibromo-o phenanthroline (3.38g, 0.01mol), 6-phenylbenzothiazol ylboronic acid (6.38g,
0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, add
50mL concentration of potassium carbonate is 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three
Secondary and use anhydrous Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, light yellow solid 5.03g, productivity are obtained
84%, HPLC purity is more than 99%.Mass spectrum: calculated value is 598.74；Test value is 598.73.Elementary analysis: calculated value is C:
74.70%；H:3.32%；N:10.25%；S:11.73%；Test value is C:74.71%；H:3.34%；N:10.23%；S:11.72%；
The synthesis of embodiment 8 compound 008
By 3,8-dibromo-o phenanthroline (3.38g, 0.01mol), 7,4-benzothiazolyl phenyl boric acids (6.38g,
0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, add
50mL concentration of potassium carbonate is 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three
Secondary and use anhydrous Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, light pink solid 5g, productivity are obtained
83.5%, HPLC purity is more than 99%.Mass spectrum: calculated value is 598.74；Test value is 598.74.Elementary analysis: calculated value is C:
74.70%；H:3.32%；N:10.25%；S:11.73%；Test value is C:74.71%；H:3.31%；N:10.24%；S:11.74%；
The synthesis of embodiment 9 compound 009
By 2,9-dibromo-o phenanthroline (3.38g, 0.01mol), 1,3-benzothiazole ylboronic acid (6.37g,
0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, add
50mL concentration of potassium carbonate is 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three
Secondary and use anhydrous Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, obtain white crystalline solid 3.82g, produce
Rate 85.5%, HPLC purity is more than 99%.Mass spectrum: calculated value is 446.55；Test value is 446.55.Elementary analysis: calculated value is
C:69.93%；H:3.16%；N:12.55%；S:14.36%；Test value is C:69.92%；H:3.18%；N:12.54%；S:
14.36%；
The synthesis of embodiment 10 compound 010
By 2,9-dibromo-o phenanthroline (3.38g, 0.01mol), aphthothiazoles ylboronic acid (6.37g, 0.025mol) and
Tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, adds 50mL concentration of potassium carbonate
For 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, wash three times and organic phase with anhydrous
Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 4.65g, productivity 85%,
HPLC purity is more than 99%.Mass spectrum: calculated value is 546.66；Test value is 546.65.Elementary analysis: calculated value is C:74.70%；
H:3.32%；N:10.25%；S:11.73%；Test value is C:74.71%；H:3.34%；N:10.23%；S:11.72%；
The synthesis of embodiment 11 compound 011
By 2,9-dibromo-o phenanthroline (3.38g, 0.01mol), 6-phenylbenzothiazol ylboronic acid (6.38g,
0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, add
50mL concentration of potassium carbonate is 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three
Secondary and use anhydrous Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 5g, productivity
83.5%, HPLC purity is more than 99%.Mass spectrum: calculated value is 598.74；Test value is 598.73.Elementary analysis: calculated value is C:
74.70%；H:3.32%；N:10.25%；S:11.73%；Test value is C:74.71%；H:3.34%；N:10.23%；S:11.72%；
The synthesis of embodiment 12 compound 012
By 2,9-dibromo-o phenanthroline (3.38g, 0.01mol), 4,7-benzothiazolyl phenyl boric acids (6.38g,
0.025mol) and tetrakis triphenylphosphine palladium (0.12g, 0.0001mol) is dissolved in the mixed liquor of 75mL toluene and water, add
50mL concentration of potassium carbonate is 2mol L-1Solution, cools down after stirring reaction 3h at 80 DEG C, separates organic phase, organic phase is washed three
Secondary and use anhydrous Na2SO4After drying, through dichloromethane/petroleum ether system column chromatography for separation, obtain creamy white crystals solid 5.03g,
Productivity 84%, HPLC purity is more than 99%.Mass spectrum: calculated value is 598.74；Test value is 598.73.Elementary analysis: calculated value is
C:74.70%；H:3.32%；N:10.25%；S:11.73%；Test value is C:74.71%；H:3.34%；N:10.23%；S:
11.72%；
The Application Example of the compounds of this invention be presented herein below:
Comparing embodiment 1: use the compound of the present invention as the electron transport material in OLED, use existing material
Material Bphen is as electron transport material, device architecture ITO/NPB (40nm)/Ir (ppy)3(10wt%)(30nm)/Bphen
(20nm)/
LiF(0.5nm)/Al(150nm)。
Device fabrication process is as follows: by be coated with the glass plate of transparent conductive layer in commercial detergent ultrasonically treated,
Rinse in deionized water, ultrasonic oil removing in acetone, alcohol mixed solvent, be baked to completely remove water under clean environment
Part, rinse with ultraviolet light and ozone, and with low energy cation bundle bombarded surface.
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9×10-3Pa, above-mentioned
On anode tunic, vacuum evaporation NPB is as hole transmission layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 40nm: pass in hole
Vacuum evaporation Ir (ppy) on defeated layer3(10wt%) as the luminescent layer of device, evaporation rate is 0.1nm/s, is deposited with total film thickness
For 30nm；On luminescent layer, vacuum evaporation one stratification compound 001 ~ 008 and Bphen is as the electron transfer layer of device, its
Evaporation rate is 0.1nm/s, and evaporation total film thickness is 20nm；(ETL) upper vacuum evaporation A1 layer is as device on the electron transport layer
Negative electrode, thickness is 150nm.
Above in comparing embodiment, the compound as luminescent layer electric transmission uses the chemical combination represented in synthesis example
The electron transport material of thing 001-008, except other use method ITO/NPB (40nm) same in comparing embodiment 1/
Ir(ppy)3(10wt%) a kind of in (30nm)/ETL(the compounds of this invention 001-008) (20nm)/LiF (0.5nm)/Al
(150nm).The organic luminescent device of structure.
Measure embodiment 1: compare sample Bphen and the luminescent properties of sample 001-008
Measure control compounds 1 and sample 001-008 is to use Keithley SMU235, evaluate luminosity, send out
Light efficiency, glow color.Compound Bphen and sample 001-008 is tested equally.The results are shown in Table 3:
Device performance see table:
By upper table it will be seen that use the device of the compounds of this invention relative to using the Bphen commonly used in the industry
Device obtains preferable effect, on the basis of driving voltage is relatively low, it is thus achieved that higher luminous efficiency.
Visible, use the compound obtained by embodiment the luminous efficiency of device can be made to have very as electron transport material
Big raising.Compound prepared by embodiment is owing to introducing the group containing benzothiazole in dibromo phenanthroline position, effectively
The LUMO value reducing material, thus further increase electric transmission and the electronics injectability of material, this is conducive to sending out
The improvement of optical device performance.
Above the present invention is described in detail, its object is to allow the personage being familiar with this art will appreciate that this
Invention content and be carried out, can not limit the scope of the invention with this, all Spirit Essence institutes according to the present invention
The equivalence change made or modification, all should contain within the scope of the present invention.
Claims (4)
1. an electroluminescent organic material, it is characterised in that the concrete structure of this material is as follows:
。
The preparation method of electroluminescent organic material the most according to claim 1, it is characterised in that the tool of this preparation method
Body step and condition are as follows: weigh bromo benzothiazole amine phenanthroline and aphthothiazoles ylboronic acid, 6,6-for 2:1 in molar ratio
Phenylbenzothiazol-2-boric acid or 4,7-benzothiazole ylboronic acid, mol ratio is that 1:1.25:0.04 weighs in above-mentioned three kinds of boric acid
One, potassium carbonate and tetrakis triphenylphosphine palladium, solvent is toluene and water, and toluene: water is 2:1 is warmed up to 100 DEG C, react 20
Hour, cooling down, suction filtration, ethanol is washed, separatory, column chromatography, recrystallization, obtains benzothiazolyl phenanthrene quinoline compounds.
3. an organic luminescent device, including the first electrode, the second electrode and be placed between described two electrodes one or more
Organic compound layer, at least one of which organic compound layer comprises at least one compound as defined in claim 1.
The electroluminescent organic material the most according to claim 1 application in organic electroluminescence device, its feature exists
In, described benzothiazolyl phenanthrene quinoline compounds is used as electron transport material in described organic electroluminescence device.
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| CN102127073B (en) * | 2010-11-26 | 2014-07-23 | 深圳大学 | Star-shaped compound taking phenanthroline as core and luminescent device comprising same |
| TWI504722B (en) * | 2010-12-03 | 2015-10-21 | Jnc Corp | Benzo[c]carbazole compound having pyridine substituent and organic electroluminescent device |
| JP5867269B2 (en) * | 2011-05-09 | 2016-02-24 | Jnc株式会社 | Benzofluorene compound, light emitting layer material and organic electroluminescent device using the compound |
| CN103468247B (en) * | 2013-09-18 | 2015-09-23 | 贵州大学 | Molecule clamp phenanthroline-benzazoles fluorescent reagent and its preparation method and application |
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