CN110526926A - A kind of azepine material and its application - Google Patents
A kind of azepine material and its application Download PDFInfo
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Abstract
The invention discloses the general formula compounds of following formula (1):
Description
Technical field
The present invention relates to a kind of novel organic compound more particularly to a kind of compounds for organic electroluminescence device
And the application in organic electroluminescence device.
Background technique
Display of organic electroluminescence (hereinafter referred to as OLED) has from main light emission, low-voltage direct-current driving, all solidstate, view
The a series of advantages such as angular width, light-weight, composition and simple process, compared with liquid crystal display, display of organic electroluminescence
Backlight is not needed, visual angle is big, and power is low, and up to 1000 times of liquid crystal display, manufacturing cost is but lower than response speed
The liquid crystal display of same resolution ratio, therefore, organic electroluminescence device has broad application prospects.
As OLED technology is in the continuous propulsion for illuminating and showing two big fields, people are for influencing OLED device performance
The research of efficient organic material focuses more on, an excellent in efficiency service life long organic electroluminescence device be usually device architecture with
The result of the optimization collocation of various organic materials.In the most common OLED device structure, the organic of following type is generally included
Material: hole-injecting material, hole mobile material, electron transport material, and assorted luminescent material (dyestuff or doping visitor
Body material) and corresponding material of main part etc..The phosphorescent light body material applied at present is all often to transmit energy with single carrier
Power, such as hole class transmit main body and electrical type transmits main body.Single carrier transport ability will cause electric in luminescent layer
The mismatch of son and hole, to cause serious efficiency roll-off and the lost of life.At present in the use process of phosphorescence host
In, to solve, single material of main part carrier is unbalanced to be asked in the form of the either double material of main part collocation of bipolar materials
Topic.Bipolar materials are to realize that the common transport of electrons and holes, molecular structure are more complex in a compound；Double main body materials
Material is to be used using two kinds of material adapteds come the transmission and combination of realizing electrons and holes in luminescent layer, one of material conduct
Electron type material, another material is as cavity type material, and electrons and holes are after the conduction of two kinds of materials, in interface
In conjunction with two kinds of material sources are more extensive, can take combination of different materials mode to realize better device performance.
Summary of the invention
The shortcomings that in order to overcome the above material of convention body in the prior art, the offer present invention of the invention provide a kind of new
Type is used for the compound of organic electroluminescence device.
General formula compound of the invention is indicated by following general formula (1):
In formula (1): X1-X8At least one is N, remaining is selected from CR ' can between adjacent R ' when there are multiple R '
To connect cyclization；
A is selected from one in NR ", O or S；
Above-mentioned R ' and R " is respectively and independently selected from hydrogen atom, the alkyl of C1-C10, substituted or unsubstituted C6-C30 aryl
Or substituted or unsubstituted C3-C30 heteroaryl；
Ar is selected from substituted or unsubstituted C6-C50 aryl or substituted or unsubstituted C3-C50 heteroaryl.
When substituent group present on above-mentioned aryl or heteroaryl, the substituent group be respectively and independently selected from halogen,
C1~C10Alkyl, C3~C10Naphthenic base, C2~C10Alkenyl, C1~C6Alkoxy, C1~C6Thio alkoxy, C6~
C30Aryl and C3~C30Heteroaryl.
Further, R ' and R " preferably independently is selected from hydrogen atom, the alkyl of C1-C5, substituted or unsubstituted C6-C20
Aryl or substituted or unsubstituted C3-C20 heteroaryl.
Further, Ar preferably is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl
Base.
Specifically, when substituent group present on above-mentioned aryl or heteroaryl, the substituent group is independently excellent
Selected from C1~C5Alkyl, C3~C5Naphthenic base, C1~C6Alkoxy, C1~C6Thio alkoxy, C6~C10Aryl and
C3~C10Heteroaryl；
When there are multiple R ', simultaneously ring structure can connect between adjacent R ', simultaneously should preferably be selected from phenyl, naphthalene by ring structure
Base or anthryl.
Further, R ' and R " preferably independently is selected from following radicals: hydrogen, methyl, ethyl, butyl, amyl, phenyl,
Xenyl, naphthalene, fluorenyl, anthryl, phenanthryl, indenyl, pyrenyl, base,Base, aphthacene base, benzo fluorenyl, Spirofluorene-based, pyridine
Base, bipyridyl, pyrimidine radicals, pyrrole radicals, phenylpyridyl, pyrazinyl, quinolyl, triazine radical, phentriazine base, benzopyrazines
Base, benzoquinoline base, dibenzopyrrole base, carbazyl, 9- phenyl carbazole base, 9- naphthyl carbazole and carbazyl or dibenzo-carbazole
Base；
Further, Ar preferably is selected from following radicals: phenyl, 2- xenyl, 3- xenyl, 4- xenyl, p- terphenyl
Base -4- base, p- terphenyl -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base,
M- terphenyl -2- base, 1- naphthalene, 2- naphthalene, 1- anthryl, 2- anthryl, 9- anthryl, phenanthryl, indenyl, benzo fluorenyl, 1- fluorenes
Base, 2- fluorenyl, 3- fluorenyl, 4- fluorenyl, 9- fluorenyl, 9,9 '-dialkyl fluorenes, 9,9 '-spiral shell, two fluorenyl, indeno fluorenyl, fluoranthene base, three
Phenylene, 1- pyrenyl, 2- pyrenyl, 4- pyrenyl, base,Base, 1- aphthacene base, 9- aphthacene base, furyl, dibenzo furan
Mutter, thienyl, dibenzothiophenes, pyrrole radicals, pyridyl group, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluorenyl and
Its derivative, fluoranthene base, triphenylene, pyrenyl, base,Base, aphthacene base, 9,9- dimethyl fluorenyl, diphenylethyllene benzene
Base, benzo fluorenyl, indeno fluorenyl or indenyl.
Further, in general formula (1) of the invention, following specific structure compound P1-P57 can preferably be gone out, this
A little compounds are only representative.
On the other hand, the present invention protects above-mentioned general formula compound to can be used as hair in organic electroluminescence device simultaneously
The application scheme of light material of main part specifically can be used as phosphorescent light body material use.
In another aspect, the present invention provides a kind of organic electroluminescence device, the structure of the device includes anode, cathode and
Organic layer, wherein include the compound of at least one aforementioned present invention general formula (1) in the organic layer.
By deepening the lumo energy of its molecule to the aza of aromatic rings in general formula compound design of the invention,
Stop passing through for electronics so as to significantly more efficient, so that hole and electronics are effectively compounded to form exciton in layer of giving out light.Into
One step ensures that voltage and efficiency when the compounds of this invention is applied to organic electroluminescence device are significantly improved.
On the one hand, general formula compound of the invention will be will have the benzo carbazole benzofuran or thiophene of conjugated polycyclic characteristic
As precursor structure, since its interatomic bond energy is high, is conducive to intermolecular solid-state accumulation, there is good thermal stability,
Be conducive to improve the service life of material.On the other hand, the compound of the present invention carries out hydridization processing on this structure, due to azepine
Mode exists.For electro main body, LUMO is deepened, and is conducive to the transmission of electronics, next strains its HOMO value mutually
It is deep, so that it has the ability for stopping hole, increase its luminous efficiency；For cavity type main body, this azepine molecule is in molecule
There are intermolecular interactions in accumulation, arrange molecule layered, are conducive to the transmission of charge.
Preparation is simple for the compounds of this invention, and raw material is easy to get, and is suitable for volume production amplification.
It, can when general formula compound of the present invention is for being used as luminescent layer material of main part in organic electroluminescence device
Effectively to provide the luminous efficiency of device, increase device stability, to obtain the organic electroluminescence device of high life.
Specific embodiment
The specific preparation method of above-mentioned noval chemical compound of the invention will be described in detail by taking multiple synthetic examples as an example below, but
Preparation method of the invention is not limited to this multiple synthetic example, and those skilled in the art can not depart from its basis
Any modification, equivalent substitution, improvement and etc. are carried out under the premise of principle of the present invention, and this method is expanded into right of the invention and is wanted
Within the scope of seeking the claimed technical solution of book.
Synthetic example
X by replacing different location, which is derived from nitrogen, can obtain different intermediate compounds.It should be noted that above-mentioned conjunction
At buchwald hartwig coupling reaction or other ring closure reactions can be used in method, but be not restricted to that such method,
Those skilled in the art can also choose other methods, can according to need selection.
More specifically, the synthetic method of representative compound of the invention is given below.
Synthesis example 1: the synthesis of compound M1
In reaction flask, the bromo- 5- iodine naphthalene 33g (100mmol) of 1-, ortho-nitrophenyl boric acid 18.4g (110mmol), Pd is added2
(PPh3)40.9g, toluene 500mL, potassium carbonate 43.3g (314mmol), water 100Ml, 100 DEG C of reaction 3.5h.End of reaction is stopped
Reaction.It is cooled to room temperature, filters, obtained solid obtains white powder M1-1 by recrystallization purifying in toluene.
In reaction flask, it is added M1-116.3g (100mmol), triphenylphosphine 26.2g (100mmol), o-dichlorohenzene 500ml,
140 DEG C of reaction 10h.End of reaction stops reacting.It is cooled to room temperature, filters, obtained solid is pure by recrystallizing in toluene
Change, obtains white powder M1-2.
It in reaction flask, is added M1-2 29.5g (100mmol), CuI-ZMS5 2g, S 10g, KOH 12g, DMF300mL are anti-
It should for 24 hours.End of reaction stops reacting.It is cooled to room temperature, is added in cold water and filters, obtained solid is obtained by column chromatographic purifying
Intermediate M1-3.
In reaction flask, it is added M1-3 36g (100mmol), palladium acetate 1.2g (5mmol), tricyclohexyl phosphine 2.8g
(10mmol), sodium tert-butoxide 19g, DMAC500ml react 5h.End of reaction stops reacting.It is cooled to room temperature, mistake in cold water is added
Filter, obtained solid obtain intermediate M1 by re crystallization from toluene.
Synthesis example 2: the synthesis of compound M2
Similarly by the chloro-pyridine boric acid of replacement different location, we are available as follows
Synthesis example 3: the synthesis of compound M3
It is similarly adjacent nitro pyridine boronic acid by ortho-nitrophenyl boric acid in replacement reaction route, while replaces chlorine in reaction equation
It is that chloro phenyl boric acid obtains for pyridine boronic acid
Synthesis example 4: the synthesis of compound M4
With the synthesis of intermediate M1, difference is to react as follows method
By M1-2 50mmol, 4- chloropyridine -3- boric acid 100mmol, copper acetate 50mmol, triethylamine 500mmol, 4A points
Son sieve 10g, methylene chloride 500mL are added in reaction flask, and air atmosphere lower 0 DEG C of reaction 6h is concentrated, column after filtering after fully reacting
The intermediate M4 of chromatography
Synthesis example 5: the synthesis of compound M5
For method with synthesis example 4, difference is 4- chloropyridine -3- boric acid to be substituted for 5- chloropyridine -4- boric acid, obtains intermediate
M5
Synthesis example 6: the synthesis of compound M6
With synthesis example 3, difference is method:
Wherein Step1 method is synthesized with M1-2, and step2 method is synthesized with M1, obtains intermediate M6
Synthesis example 7: the synthesis of compound P1
By M2 50mmol, S1 52mmol, Pd2(dba)30.5mmol, tri-tert-butylphosphine 1mmol, sodium tert-butoxide
100mmol, dimethylbenzene 300mL are added in reaction flask, and heating reflux reaction 6h is down to room temperature after the reaction was completed, filtering, filter cake two
Silicagel column, the product P1 of concentration are crossed after chloromethanes dissolution1H NMR(500MHz,Chloroform)δ9.51(s,1H),9.03–
8.91 (m, 1H), 8.66-8.49 (m, 2H), 8.43-8.31 (m, 2H), 8.24 (d, J=15.0Hz, 1H), 8.06-7.90 (m,
2H),7.89–7.73(m,3H),7.58–7.29(m,8H),7.22–7.05(m,3H)；MS=606.
Synthesis example 8: the synthesis of compound P5
With synthesis example 7, difference is to replace with S1 into the 2- chloro- 4- phenylquinazoline of equivalent method, obtains product P5.1H
NMR (500MHz, Chloroform) δ 9.51 (s, 1H), 8.61 (d, J=7.5Hz, 1H), 8.55 (dd, J=7.3,1.6Hz,
1H), 8.23 (d, J=7.5Hz, 1H), 8.13 (dd, J=7.4,1.5Hz, 1H), 8.00 (dd, J=7.5,1.6Hz, 1H),
7.79 (ddd, J=7.5,5.4,1.6Hz, 4H), 7.65 (t, J=7.5Hz, 2H), 7.58-7.45 (m, 3H), 7.40 (d, J=
7.5Hz, 1H), 7.33 (d, J=7.5Hz, 1H), 7.21-7.06 (m, 3H)；MS=529.
Synthesis example 9: the synthesis of compound P39
With synthesis example 7, difference is to replace with M2 into equivalent M4 method, and S1 replaces with chloro- 4, the 6- hexichol of equivalent 2-
Yl pyrimidines obtain product P39.1H NMR(500MHz,Chloroform)δ8.86(s,1H),8.66–8.49(m,3H),8.31(d,J
=14.9Hz, 1H), 7.98-7.88 (m, 4H), 7.64-7.44 (m, 8H), 7.40 (d, J=15.0Hz, 1H), 7.27-7.05
(m,4H)；MS=539
Synthesis example 10: the synthesis of compound P41
With synthesis example 7, difference is to replace with M2 into equivalent M3 method, and S1 replaces with equivalent 2- chloro- 4 (1- naphthalene)
Quinazoline obtains product P41.1H NMR(500MHz,Chloroform)δ9.01–8.92(m,1H),8.48–8.35(m,3H),
8.13 (dd, J=7.4,1.5Hz, 1H), 8.00 (t, J=7.5Hz, 1H), 7.97-7.88 (m, 2H), 7.88-7.75 (m, 5H),
7.61-7.43 (m, 6H), 7.35-7.26 (m, 2H), 7.07 (t, J=7.5Hz, 1H)；MS=579
Synthesis example 11: the synthesis of compound P50
With synthesis example 7, difference is to replace with M2 into equivalent M6 method, obtains product P50.1H NMR(500MHz,
Chloroform) δ 9.02-8.91 (m, 1H), 8.55 (dd, J=14.2,3.7Hz, 1H), 8.47-8.29 (m, 4H), 8.05-
7.90(m,2H),7.89–7.78(m,2H),7.69–7.40(m,14H),7.21–7.00(m,4H)；MS=665
Device embodiments
Embodiment
Organic Light Emitting Diode includes the first electrode and second electrode on substrate, and having between electrode
Machine material includes hole transmission layer, luminescent layer, electron transfer layer between first electrode and second electrode.
Substrate using substrate used in organic light emitting display, such as: glass, polymer material and have TFT member device
Glass and polymer material of part etc..
Anode material can use indium tin oxygen (ITO), indium zinc oxygen (IZO), stannic oxide (SnO2), zinc oxide (ZnO) etc.
Transparent conductive material is also possible to the metal materials such as silver and its alloy, aluminium and its alloy, is also possible to the organic conductives such as PEDOT
The multilayered structure of material and above-mentioned material.
Cathode includes but is not limited to metals, metal mixture, the oxides such as magnesium silver mixture, LiF/Al, ITO.
Hole transmission layer includes but is not limited to one or more combinations of the following HT1-HT31 enumerated.
The luminescent layer of organic electroluminescence device includes material of main part and dyestuff, wherein material of main part includes but is not limited to
One of GPH1-GPH80 or a variety of combinations
Dyestuff includes but is not limited to one or more compositions of the following RPD1-RPD29 enumerated.
Electron transfer layer includes but is not limited to one or more combinations of the following ET1-ET57 enumerated.
It can also include the electron injecting layer between electron transfer layer and cathode, electron injecting layer material packet in device
It includes but is not limited to the following one or more combinations enumerated.
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca。
Organic electroluminescence device preparation process is as follows in the present embodiment:
The glass plate for being coated with transparent conductive layer is ultrasonically treated in commercial detergent, is rinsed in deionized water,
In acetone: ultrasonic oil removing in alcohol mixed solvent is baked under clean environment and completely removes moisture content, clear with ultraviolet light and ozone
It washes, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to less than 1 × 10-5, in above-mentioned anode layer
Vacuum evaporation HT-11 is as hole injection layer on film, and evaporation rate 0.1nm/s, vapor deposition film thickness is 10nm；
Hole transmission layer of the vacuum evaporation HT-5 as device on hole injection layer, evaporation rate 0.1nm/s steam
Plating total film thickness is 80nm；
The luminescent layer of vacuum evaporation device on hole transmission layer, luminescent layer include material of main part and dye materials, benefit
The method steamed altogether with multi-source, adjusting material of main part P1 evaporation rate are 0.1nm/s, and 3% ratio of dyestuff RPD-5 evaporation rate is set
Fixed, vapor deposition total film thickness is 30nm；
The electron transport layer materials ET42 of vacuum evaporation device, evaporation rate 0.1nm/s on luminescent layer, vapor deposition
Total film thickness is 30nm；
On electron transfer layer (ETL) vacuum evaporation with a thickness of the LiF of 0.5nm as electron injecting layer, with a thickness of 150nm
Cathode of the Al layer as device.
The preparation process of device embodiments 2-5 and comparative example 1 is with embodiment 1, the difference is that by material of main part
P5, P39, P41, P50 and C1 are changed by P1.
Following performance measurement is carried out to the organic electroluminescence device prepared by the above process:
Under same brightness, had using what digital sourcemeter and luminance meter measurement embodiment 1-5 and comparative example 1 were prepared
The driving voltage and current efficiency of organic electroluminescence devices and the service life of device.Specifically, being mentioned with the rate of 0.1V per second
Up voltage, measurement reach 10000cd/m when the brightness of organic electroluminescence device2When voltage, that is, driving voltage, measure simultaneously
Current density at this time；The ratio of brightness and current density is current efficiency；The life test of LT95 is as follows: using luminance meter
In 10000cd/m2Under brightness, the electric current kept constant, the brightness for measuring organic electroluminescence device is reduced to 9500cd/m2When
Between, unit is hour.
Organic electroluminescence device performance see the table below:
By embodiment 1-5 with device performance test result prepared by comparative example 1 as it can be seen that the compound that the present invention synthesizes
When being applied to the material of main part in luminescent layer in the devices, side of the comparison using known OLED material C1 as light emitting host
Case, the current efficiency of device and service life all obtain larger change, and especially life-span upgrading is obvious, while effectively reducing device
Landing voltage.It can be seen that can be used as performance when new organic materials of the invention are applied to organic electroluminescence device
Good material of main part.
Although the present invention is described in conjunction with the embodiments, the present invention is not limited to the above embodiments, should manage
Solution, under the guidance of present inventive concept, those skilled in the art can carry out various modifications and improve, and appended claims summarise
The scope of the present invention.
Claims (8)
1. a kind of general formula compound, as shown in following formula (1):
In formula (1): A is selected from NR ", O or S；
X1-X8It is respectively and independently selected from N or CR ', and wherein at least one is N, it can be with when there are multiple R ', between adjacent R '
Connection cyclization；
Above-mentioned R ' and R " is respectively and independently selected from hydrogen atom, the alkyl of C1-C10, substituted or unsubstituted C6-C30 aryl or substitution
Or unsubstituted C3-C30 heteroaryl；
Ar is selected from substituted or unsubstituted C6-C50 aryl or substituted or unsubstituted C3-C50 heteroaryl；
When substituent group present on above-mentioned aryl or heteroaryl, the substituent group is respectively and independently selected from halogen, C1~
C10Alkyl, C3~C10Naphthenic base, C2~C10Alkenyl, C1~C6Alkoxy, C1~C6Thio alkoxy, C6~C30's
Aryl or C3~C30Heteroaryl one or more groups.
2. general formula compound according to claim 1, in which:
R ' and R " is respectively and independently selected from hydrogen atom, the alkyl of C1-C5, substituted or unsubstituted C6-C20 aryl or substitution or does not take
The C3-C20 heteroaryl in generation；
Ar is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl；
When substituent group present on above-mentioned aryl or heteroaryl, the substituent group is respectively and independently selected from C1~C5Alkane
Base, C3~C5Naphthenic base, C1~C6Alkoxy, C1~C6Thio alkoxy, C6~C10Aryl and C3~C10Heteroaryl
Base；
When there are multiple R ', simultaneously ring structure can connect between adjacent R ', simultaneously should be selected from phenyl, naphthalene or anthracene by ring structure
Base.
3. general formula compound of any of claims 1 or 2, in which:
R ' and R " is respectively and independently selected from following radicals: hydrogen, methyl, ethyl, butyl, amyl, phenyl, xenyl, naphthalene, fluorenyl,
Anthryl, phenanthryl, indenyl, pyrenyl, base,Base, aphthacene base, benzo fluorenyl, Spirofluorene-based, pyridyl group, bipyridyl, pyrimidine
Base, pyrrole radicals, phenylpyridyl, pyrazinyl, quinolyl, triazine radical, phentriazine base, benzopyrazines base, benzoquinoline base, two
Benzopyrrole base, carbazyl, 9- phenyl carbazole base, 9- naphthyl carbazole and carbazyl or dibenzo-carbazole base；
Ar is selected from following radicals: phenyl, 2- xenyl, 3- xenyl, 4- xenyl, p- terphenyl -4- base, p- terphenyl
Base -3- base, p- terphenyl -2- base, m- terphenyl -4- base, m- terphenyl -3- base, m- terphenyl -2- base,
1- naphthalene, 2- naphthalene, 1- anthryl, 2- anthryl, 9- anthryl, phenanthryl, indenyl, benzo fluorenyl, 1- fluorenyl, 2- fluorenyl, 3- fluorenyl, 4-
Fluorenyl, 9- fluorenyl, 9,9 '-dialkyl fluorenes, 9,9 '-spiral shell, two fluorenyl, indeno fluorenyl, fluoranthene base, triphenylene, 1- pyrenyl, 2- pyrene
Base, 4- pyrenyl, base,Base, 1- aphthacene base, 9- aphthacene base, furyl, dibenzofurans, thienyl, dibenzo thiophene
Pheno, pyrrole radicals, pyridyl group, xenyl, terphenyl, naphthalene, anthryl, phenanthryl, indenyl, fluorenyl and its derivative, fluoranthene base, three
Phenylene, pyrenyl, base,Base, aphthacene base, 9,9- dimethyl fluorenyl, diphenylethyllene phenyl, benzo fluorenyl, indenofluorene
Base or indenyl.
4. general formula compound according to claim 1 is selected from following specific structure compounds:
5. the application of general formula compound of any of claims 1 or 2, the application is the luminescent layer in organic electroluminescence device
It is middle to be used as light emitting host material.
6. the application of structural compounds according to claim 4, the application is shining in organic electroluminescence device
Light emitting host material is used as in layer.
7. a kind of organic electroluminescence device, which includes first electrode, second electrode and the insertion first electrode and the
One or more layers organic layer between two electrodes, which is characterized in that include at least one in the organic layer by claim 1 institute
State the general formula compound of formula (1) expression.
8. a kind of organic electroluminescence device according to claim 7, which is characterized in that include in the organic layer by
The general formula compound that formula described in claim 1 (1) indicates is selected from following specific structure compounds:
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804333A (en) * | 2012-11-01 | 2014-05-21 | 三星显示有限公司 | Heterocyclic compound and organic light emitting diode comprising the same |
| KR20140120090A (en) * | 2013-04-02 | 2014-10-13 | 에스에프씨 주식회사 | An organoelectro luminescent compounds and organoelectro luminescent device using the same |
| KR20160090058A (en) * | 2015-01-21 | 2016-07-29 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| CN106661026A (en) * | 2014-07-10 | 2017-05-10 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804333A (en) * | 2012-11-01 | 2014-05-21 | 三星显示有限公司 | Heterocyclic compound and organic light emitting diode comprising the same |
| KR20140120090A (en) * | 2013-04-02 | 2014-10-13 | 에스에프씨 주식회사 | An organoelectro luminescent compounds and organoelectro luminescent device using the same |
| CN106661026A (en) * | 2014-07-10 | 2017-05-10 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| KR20160090058A (en) * | 2015-01-21 | 2016-07-29 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
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