CN107619406A - A kind of new carbazole analog derivative and preparation method thereof and application in the devices - Google Patents
A kind of new carbazole analog derivative and preparation method thereof and application in the devices Download PDFInfo
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- CN107619406A CN107619406A CN201610558982.5A CN201610558982A CN107619406A CN 107619406 A CN107619406 A CN 107619406A CN 201610558982 A CN201610558982 A CN 201610558982A CN 107619406 A CN107619406 A CN 107619406A
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- substituted
- unsubstituted
- analog derivative
- carbazole
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- 0 CCC(CC*=[Pm+])=CN=C Chemical compound CCC(CC*=[Pm+])=CN=C 0.000 description 1
- NIUWAQZSVWHLFM-BRFYHDHCSA-N CCN[C@H](C1)C1C(C)C Chemical compound CCN[C@H](C1)C1C(C)C NIUWAQZSVWHLFM-BRFYHDHCSA-N 0.000 description 1
Abstract
The invention provides a kind of carbazole analog derivative, compared with prior art, different nitrogen heterocyclic ring class substituents are introduced in carbazole analog derivative provided by the invention, form new carbazole analog derivative effect, simultaneously also can be by adjusting molecular weight and the species of substituent to improve the performance of carbazole analog derivative, the features such as device prepared thereby using the new carbazole derivates class of the present invention possesses long-life and high efficiency.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, more particularly to a kind of carbazole analog derivative and preparation method thereof and
Using.
Background technology
Since Tang in 1987 etc. is successfully prepared the small molecule light emitters part of low-voltage driving, organic light emission technology has obtained
Huge progress, and initially enter industrialization process；Wherein, electroluminescent organic material rises to the performance of organic luminescent device
Very important effect.
According to the size of electroluminescent organic material molecular weight, small molecule electroluminescent organic material and high score can be divided into
Sub- electroluminescent organic material.In presently disclosed luminescent material, due to the fluorescence quantum efficiency of small molecule electroluminescent material
Height, be easily purified, luminosity and excitation also superior to high polymer material, so, small molecule electroluminescent materials application is in hair
Optical device is commercialized with starting to realize.
Organic luminescent device (OLED) is typically to be made up of the organic matter layer inserted between negative electrode, anode and negative electrode and anode
, i.e. the composition of device is by transparent ITO anode, hole injection layer（TIL）, hole transmission layer（HTL）, luminescent layer（EL）, it is empty
Cave barrier layer（HBL）, electron transfer layer（ETL）, electron injecting layer（EIL）Formed with negative electrode, it is organic that 1 ~ 2 can be omitted on demand
Layer.Its mechanism of action forms voltage while being injected from cathode electronics between two electrodes, and hole, electricity are injected in another side from anode
Son and hole return to stable ground state in luminescent layer in conjunction with excitation state, excitation state is formed.
Wherein, the luminescent material in luminescent device is divided into fluorescent material and phosphor material, and the forming method of luminescent layer is main
Have：1) phosphor material is adulterated in fluorescent host material（Organic metal）, 2）Fluorescent host material doping fluorescent（Include the organic of nitrogen
Thing）Dopant, 3）Dopant is utilized in illuminator（DCM, Rubrene, DCJTB etc.）Realize long wavelength；And adulterate luminous
Material has a great impact to the emission wavelength of luminescent device, efficiency, driving voltage and life-span.Improved by such doping
The factors such as emission wavelength, efficiency, driving voltage, life-span.
Generally form emitting layer material be with the centerbodies such as benzene, naphthalene, fluorenes, the fluorenes of spiral shell two, anthracene, pyrene, carbazole and benzene, biphenyl,
The parts such as naphthalene, heterocycle；The replacing structure such as contraposition, meta, the binding site at ortho position and amido, cyano group, fluorine, methyl, the tert-butyl group.
As oled panel develops into maximization, it is necessary to the higher material of brightness and there is more preferable heat resistance, separately
One side luminous efficiency and life-span are also required to further improve.But presently disclosed luminescent material, luminous efficiency and life-span
It is poor.
Therefore, develop that a kind of luminous efficiency is high and luminescent material with longer life, it has also become this area respectively production and
Application vendor is urgently the technical problem solved.
The content of the invention
In consideration of it, the technical problem to be solved in the present invention is to provide a kind of new carbazole analog derivative and its preparation side
Method, organic electroluminescence device, the compound light-emitting efficiency is preferable and service life is grown.
The invention provides a kind of carbazole analog derivative, the carbazole analog derivative has the structure of chemical formula 1,
Chemical formula 1
Wherein, R1 and R2 is hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl；
R ' and R ' ' is hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl, substitution or
For substituted C5 ~ C20 heterocyclic radical；
Ar1 and Ar2 be substituted or unsubstituted C3 ~ C30 cycloalkyl, substituted or unsubstituted C6 ~ C30 aryl, substitution or
For substituted C8 ~ C20 condensed ring radical, or when Ar1 and Ar2 is phenyl, it is connected to form carbazole class formation with connected nitrogen.
A1 ~ A10 can be the same or different, and be independently selected from N.
The carbazole analog derivative as shown in any one in chemical formula 2-1 ~ chemical formula 2-4,
Chemical formula 2-1
Chemical formula 2-2
Chemical formula 2-3
Chemical formula 2-4
A1 ~ the A10 can be the same or different, and be independently selected from N；
The R1 and R2 are hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl.
Preferably, the R1 or R2 are selected from hydrogen or phenyl.
The carbazole analog derivative as shown in any one of structural formula 001 ~ 027,
。
Present invention also offers a kind of preparation method of the carbazole analog derivative described in above-mentioned any one technical scheme, bag
Include following steps：
By formula（A）The compound and formula of structure（B）After the compound of structure is reacted, formula is obtained（C）The compound of structure,
（A）,（B）,（C）；
Wherein, R1 and R2 is hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl；
R ' and R ' ' is hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl, substitution or
For substituted C5 ~ C20 heterocyclic radical；
Ar1 and Ar2 be substituted or unsubstituted C3 ~ C30 cycloalkyl, substituted or unsubstituted C6 ~ C30 aryl, substitution or
For substituted C8 ~ C20 condensed ring radical, or when Ar1 and Ar2 is phenyl, it is connected to form carbazole class formation with connected nitrogen；
The X independences are selected from I, Br or Cl；
The present invention is to substituent in the raw material or the range of choice and optimum principle of structure, such as without especially indicating, with foregoing click
The range of choice of azole derivative is consistent with optimum principle, and this is no longer going to repeat them.
The present invention does not have particular/special requirement to the ratio of the raw material, with the normal of such reaction well known to those skilled in the art
Rule ratio, those skilled in the art can be selected and adjusted according to practical condition, product requirement or quality requirement
It is whole.The present invention does not have particular/special requirement to the condition of the reaction, with the conventional strip of such reaction well known to those skilled in the art
Part, those skilled in the art can be selected and adjusted according to practical condition, product requirement or quality requirement, this
It is preferably toluene to invent the solvent.
In addition, the present invention is to formula（A）The compound and formula of structure（B）The source of the compound of structure is not particularly limited,
It is made by preparation method well known in the art or commercially available purchase.
Present invention also offers a kind of organic electroluminescence device, including electroluminescent material；The electroluminescent material
Including the carbazole analog derivative described in above-mentioned technical proposal any one or the carbazole analog derivative prepared by above-mentioned technical proposal.
Organic electroluminescence device of the present invention preferably includes：
First electrode, second electrode and the organic matter layer being placed between two electrode, wherein, include in the organic matter layer
The compound of structure shown in chemical formula 1；The compound of structure shown in chemical formula 1 can be single form or be mixed with other materials
It is present in organic matter layer.
Wherein, the organic matter layer comprises at least hole injection layer, hole transmission layer, had both possessed hole injection but also with sky
Technical ability layer is transmitted in cave, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and both possesses electronics biography
One or more in the defeated technical ability layer but also with electron injection.
The hole injection layer, the hole transmission layer, it is described both possessed hole injection but also with hole transport technical ability layer
In at least one be conventional hole injecting material, hole transporting material or both possess hole injection but also with hole transport
Technical ability material, it is also possible to be the material of electron-transporting material generation.
" organic matter layer " refers to the whole disposed between organic electronic device first electrode and second electrode in this patent
The term of layer.
For example above-mentioned organic matter layer includes luminescent layer, above-mentioned organic matter layer includes phosphorescence host, fluorescent host, phosphorescence
Doping and fluorescence doping in more than one, wherein above-mentioned luminescent layer includes the heterocyclic ligand of the above-mentioned structure of chemical formula 1, i) on
State the heterocyclic ligand ii that fluorescent host can be the above-mentioned structure of chemical formula 1) doping of above-mentioned fluorescence can be the above-mentioned knot of chemical formula 1
The heterocyclic ligand iii of structure）Above-mentioned fluorescent host and fluorescence doping can be the heterocyclic ligand of the above-mentioned structure of chemical formula 1.
Specifically, when the compound of the structure of chemical formula 1 is present in the luminescent layer in the organic layer, the chemical formula 1
The compound of structure can as electroluminescent material light emitting host or be entrained in other fluorescent hosts；Such as：It is luminous
Layer can be red, yellow or blue light-emitting layer.And by the compound doped in blue main body of the structure of chemical formula 1, Ke Yiti
Efficiency, brightness, resolution ratio and the long-life of high luminescent device.
When the compound of the structure of chemical formula 1 is present in electron transfer layer, the electron transfer layer also includes containing metal
Compound.
When the organic layer includes luminescent layer and electron transfer layer, the compound of the structure of chemical formula 1 may have
In wherein one layer or two layers.
Device prepared by the compound of the present invention for including the structure of chemical formula 1 can be used for organic luminescent device
（OLED）, organic photovoltaic cell（OSC）, Electronic Paper（e-Paper）, Organophotoreceptor（OPC）Or OTFT
（OTFT）.
Device of the present invention can by the methods of film vapor deposition, electron beam evaporation, physical vapour deposition (PVD) in substrate
Upper evaporation metal and conductive oxide and their alloy form anode, can also use spin-coating（spin-
coating）Or strip takes the lead to be deposited；Shaping can also be used（tape-casting）, scraping blade method（doctor-blading）, silk
Wire mark brush（Screen-Printing）, ink jet printing or number of plies manufacture is reduced the methods of thermal imaging (Thermal-Imaging).
The invention provides a kind of carbazole analog derivative, compared with prior art, carbazole analog derivative provided by the invention
It is middle to introduce different nitrogen heterocyclic ring class substituents, new carbazole analog derivative effect is formed, while also can be by adjusting substituent
Molecular weight and species are to improve the performance of carbazole analog derivative, thereby using the device of the new carbazole derivates class preparation of the present invention
Part possesses the features such as long-life and high efficiency.
It is clearly and completely described below in conjunction with the technical scheme of the embodiment of the present invention, it is clear that described implementation
Example only part of the embodiment of the present invention, rather than whole embodiments.It is common based on the embodiment in the present invention, this area
The every other embodiment that technical staff is obtained under the premise of creative work is not made, belong to the model that the present invention protects
Enclose.
Embodiment
Intermediate 1-1 ~ intermediate 1-4 synthesis：
Weigh 1,3-two bromo- 5- fluorobenzene 1mmol, 9H- carbazole 1.2mmol, 9H- carbazole 1.2mmol stannous chlorides 0.2mmol and
20mmol potassium carbonate, DMSO are solvent 40ml, are heated to reflux within 8 hours.Reaction oil body is cooled to room temperature, is separated out with recrystallizing methanol
Crystallization be separated by filtration, the residual silica gel column chromatography of gained obtains intermediate 1-1, the % of yield=50.According to above-mentioned centre
Body 1-1 preparation method synthetic intermediate 1-2 ~ 1-4, table 1 are that reactive material, generation material and yield of the present invention collect.
The intermediate 1-1 of table 1 ~ intermediate 1-4 reactive materials, generation material and yield collect
Intermediate 2-1 ~ intermediate 2-4 synthesis：
0.018mol intermediates 1-1 is dissolved in 100ml, in dry THF, added afterwards in dried 500ml there-necked flasks, N2
- 78 DEG C of reaction 30min, are slowly added dropwise the mol of n-BuLi 0.027 under protection, -78 DEG C of reaction 3h are kept after completion of dropwise addition, then delay
It is slow that triisopropyl borate ester 0.02mol is added dropwise, reaction is maintained at -78 DEG C of 2 h of reaction after completion of dropwise addition, is to slowly warm up to room temperature,
Overnight, after TLC monitoring reactions terminate, reaction solution is slowly quenched with water, extraction is evaporated to obtain 0.0144mol intermediate 2-1, produces in reaction
Rate is 80%.According to above-mentioned intermediate 2-1 preparation method synthetic intermediate 2-2 ~ 2-4, table 2 is reactive material of the present invention, generation
Material and yield collect.
The intermediate 2-1 of table 2 ~ intermediate 2-4 reactive materials, generation material and yield collect
Intermediate 3-1 ~ intermediate 3-4 synthesis：
The bromo- 3- fluorobenzene 8.9mmol of 1-,（3,5- bis-（9H- carbazole -9- bases）Phenyl）Boric acid 9.8mmol, tetra-triphenylphosphine palladium
0.3mmol and potassium carbonate 0.02mol is dissolved in 100ml toluene:H2O=2:1 in the mixed solvent, 80 DEG C of stirring 5h, nitrogen are protected
Shield, after TLC monitoring reactions terminate, room temperature is cooled to, is extracted with dichloromethane and water, rear organic phase is dried with anhydrous magnesium sulfate
After be evaporated, be evaporated rear product column chromatography and obtain 7.92mmol intermediate 3-1, yield 89%.According to above-mentioned intermediate 3-1 preparation side
Method synthetic intermediate 3-2 ~ 3-4, table 3 are that reactive material, generation material and yield of the present invention collect.
The intermediate 3-1 of table 3 ~ intermediate 3-4 reactive materials, generation material and yield collect
Intermediate 4-1 ~ intermediate 4-11 synthesis：
According to above-mentioned intermediate 1-1 preparation method synthetic intermediate 4-1 ~ 4-13, table 4 is reactive material of the present invention, product
Matter and yield collect.
The intermediate 4-1 of table 4 ~ intermediate 4-13 reactive materials, generation material and yield collect
Intermediate 5-1 ~ 5-13 synthesis：
According to above-mentioned intermediate 2-1 preparation method synthetic intermediate 5-1 ~ 5-13, table 5 is reactive material of the present invention, product
Matter and yield collect.
The intermediate 5-1 of table 5 ~ intermediate 5-13 reactive materials, generation material and yield collect
The synthesis of target product 001 ~ 027：
The bromo- 3,5- bis- of 3'-（9- carbazoles）Biphenyl 8.9mmol, 3,5- bis- (2- pyridine radicals) phenylboric acid 9.8mmol, four triphenyls
Phosphine palladium 0.3mmol and potassium carbonate 0.02mol is dissolved in 100ml toluene:H2O=2:1 in the mixed solvent, 80 DEG C of stirring 5h, nitrogen
Protection, after TLC monitoring reactions terminate, room temperature is cooled to, is extracted with dichloromethane and water, rear organic phase is done with anhydrous magnesium sulfate
It is evaporated after dry, is evaporated rear product column chromatography and obtains 7.83mmol target products 001, yield 88%.Mass spectrum：714.89.
Preparation method according to above-mentioned target product 001 synthesizes target product 002 ~ 027, table 6 be reactive material of the present invention,
Generation material and yield collect.
The reactive material of 6 001 ~ target product of target product of table 027, generation material and yield collect
Obtaining portion of product mass spectrometry value by test is：Compound 007:716.91;Compound 022:770.96;Compound 027:
766.97。
Device prepares embodiment：
Application Example 1（Blue phosphorescent device）
The ito glass substrate that Fisher Co., Ltd's coating layer thickness is 1500 is placed in distilled water and cleaned 2 times, ultrasonic washing 30
Minute, cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleaning terminates, isopropanol, acetone, methanol etc.
Solvent in order dry later by ultrasonic washing, is transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, is sent to
In evaporator.According to ITO（1000Å）/ NPB（700Å）/ mCP（150Å）The compound of/chemical formula 11：FIrpic（92：8
Weight, 300）/ Bphen（250Å）/ LiF（5Å）/Al（1000Å）Device is carried out to present invention synthesis combinations of materials
Test.
Application Example 2（Green phosphorescent device）
The ito glass substrate that Fisher Co., Ltd's coating layer thickness is 1500 is placed in distilled water and cleaned 2 times, ultrasonic washing 30
Minute, cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleaning terminates, isopropanol, acetone, methanol etc.
Solvent in order dry later by ultrasonic washing, is transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, is sent to
In evaporator.According to ITO（1000Å）/ NPB（700Å）/ TCTA（100Å）The compound of/chemical formula：11 Ir（ppy）3
（93：7 mass ratioes, 300）/ Alq 3（250Å）/LiF（5Å）/Al（1000Å）Present invention synthesis combinations of materials is entered
Row device detection.
Application Example 3（White phosphor device）
The ito glass substrate that Fisher Co., Ltd's coating layer thickness is 1500 is placed in distilled water and cleaned 2 times, ultrasonic washing 30
Minute, cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleaning terminates, isopropanol, acetone, methanol etc.
Solvent in order dry later by ultrasonic washing, is transferred in plasma washing machine, aforesaid substrate is washed 5 minutes, is sent to
In evaporator.According to ITO（1000Å）/ TCTA：WoO 3（70：30 mass ratioes, 600）/ TCTA（100Å）/ chemical formula
11：FIrpic：Ir（phq）2（acac）：Ir（PPy）3（91：8：0.5：0.5 mass ratio, 150）/ BePP 2（100Å）/
BePP 2：Cs2CO 3（90：10 mass ratioes, 200）/ LiF（5Å）/Al（1000Å）Combinations of materials is synthesized to the present invention
Carry out device detection.
The luminescent device that the present invention is prepared is used into the type source measuring unit of KEITHLEY Keithleys 2400, CS-2000
Spectroradio luminance meter is tested, to evaluate the driving voltage of luminescent device, luminosity, luminous efficiency and glow color；
The obtained performance characteristics of luminescence of device is tested, the results are shown in Table 7, table 7 be the part of compounds for preparing of the embodiment of the present invention with
And compare the characteristics of luminescence test result of the luminescent device of material preparation.
The characteristics of luminescence test result of part of compounds luminescent device prepared by the embodiment of the present invention of table 7
From the above-mentioned result of table 7, it is seen that prepared by the new carbazole analog derivative provided by the invention with the structure of chemical formula 1
The luminous efficiency and life characteristic of organic electroluminescence device increase significantly.
The present invention can obtain luminous efficiency and life-span good result using the organic luminescent device of carbazole analog derivative,
Therefore the high OLED industries of practicality be can be applied to.The present invention organic electroluminescence device be applicable to flat panel show,
Face illuminating OLED illuminator, flexible illuminator, duplicator, printer, LCD backlight lamp or dosing machine are used in planar illuminant, illumination
The light source of class, display board, mark etc..
The explanation of above example is only intended to help the method and its core concept for understanding the present invention.It should be pointed out that pair
For those skilled in the art, under the premise without departing from the principles of the invention, the present invention can also be carried out
Some improvement and modification, 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 carbazole analog derivative, it is characterised in that the carbazoles derivative molecular formula is：
Chemical formula 1
Wherein, R1And R2For hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl；
R ' and R ' ' is hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl, substitution or
For substituted C5 ~ C20 heterocyclic radical；
Ar1And Ar2For substituted or unsubstituted C3 ~ C30 cycloalkyl, substituted or unsubstituted C6 ~ C30 aryl, substitute or be
Substituted C8 ~ C20 condensed ring radical, or work as Ar1With Ar2For phenyl when, be connected to form carbazole class formation with connected nitrogen；
A1 ~ A10 can be the same or different, and be independently selected from N.
2. carbazole analog derivative according to claim 1, it is characterised in that the carbazole analog derivative such as chemical formula 2-1 ~
In chemical formula 2-4 shown in any one,
Chemical formula 2-1
Chemical formula 2-2
Chemical formula 2-3
Chemical formula 2-4
A1 ~ the A10 can be the same or different, and be independently selected from N；
The R1And R2For hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl.
3. carbazole analog derivative according to claim 2, it is characterised in that the R1Or R2Selected from hydrogen or phenyl.
4. carbazole analog derivative according to claim 1, it is characterised in that the carbazole analog derivative such as structural formula 001 ~
Shown in 027 any one,
。
A kind of 5. preparation method of carbazole analog derivative as described in claim 1 ~ 4 any one, it is characterised in that including with
Lower step：
By formula（A）The compound and formula of structure（B）After the compound reaction of structure, formula is obtained（C）The compound of structure,
（A）,（B）,（C）；
Wherein, R1And R2For hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl；
R ' and R ' ' is hydrogen, substituted or unsubstituted C1 ~ C20 alkyl, substituted or unsubstituted C6 ~ C20 aryl, substitution or
For substituted C5 ~ C20 heterocyclic radical；
Ar1And Ar2For substituted or unsubstituted C3 ~ C30 cycloalkyl, substituted or unsubstituted C6 ~ C30 aryl, substitute or be
Substituted C8 ~ C20 condensed ring radical, or work as Ar1With Ar2For phenyl when, be connected to form carbazole class formation with connected nitrogen；
The X independences are selected from I, Br or Cl.
6. a kind of organic electroluminescence device, it is characterised in that including electroluminescent material；The electroluminescent material includes power
Profit requires the carbazole analog derivative prepared by carbazole analog derivative or claim 5 described in 1 ~ 4 any one.
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| CN110386894A (en) * | 2018-04-20 | 2019-10-29 | 北京鼎材科技有限公司 | A kind of hole mobile material and its application |
| WO2020035365A1 (en) * | 2018-08-13 | 2020-02-20 | Cynora Gmbh | Organic molecules for optoelectronic devices |
| CN112018248A (en) * | 2019-05-28 | 2020-12-01 | 固安鼎材科技有限公司 | Display device and preparation method thereof |
| KR20210126810A (en) * | 2020-04-10 | 2021-10-21 | (주)씨엠디엘 | Bis phenyl pyrazine derivatives organic light emitting compound and organic electroluminescent device including the same |
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| TW201134809A (en) * | 2010-01-15 | 2011-10-16 | Fujifilm Corp | Organic electroluminescent device |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110386894A (en) * | 2018-04-20 | 2019-10-29 | 北京鼎材科技有限公司 | A kind of hole mobile material and its application |
| WO2020035365A1 (en) * | 2018-08-13 | 2020-02-20 | Cynora Gmbh | Organic molecules for optoelectronic devices |
| CN112566908A (en) * | 2018-08-13 | 2021-03-26 | 辛诺拉有限公司 | Organic molecules for optoelectronic devices |
| CN112018248A (en) * | 2019-05-28 | 2020-12-01 | 固安鼎材科技有限公司 | Display device and preparation method thereof |
| CN112018248B (en) * | 2019-05-28 | 2023-12-29 | 固安鼎材科技有限公司 | Display device and preparation method thereof |
| KR20210126810A (en) * | 2020-04-10 | 2021-10-21 | (주)씨엠디엘 | Bis phenyl pyrazine derivatives organic light emitting compound and organic electroluminescent device including the same |
| KR102346943B1 (en) * | 2020-04-10 | 2022-01-06 | (주)씨엠디엘 | Bis phenyl pyrazine derivatives organic light emitting compound and organic electroluminescent device including the same |
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