CN109851613A - A kind of new compound and the organic electroluminescence device using the compound - Google Patents
A kind of new compound and the organic electroluminescence device using the compound Download PDFInfo
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Abstract
The present invention provides a kind of organic electroluminescence devices, including first electrode, second electrode and one or more layers organic layer between the first electrode and second electrode, comprising at least one by the following general formula (I) compound represented in the organic layer:In formula (I): R1Selected from cyano or hydrogen；L is selected from aryl or condensed-nuclei aromatics group, heteroaryl or condensed hetero ring aromatic hydrocarbon group；Ar is selected from the heteroaryl containing oxygen atom or sulphur atom or condensed hetero ring aromatic hydrocarbon group；Substituent group on L or Ar is independently selected from halogen, cyano, nitro, alkyl or cycloalkyl, alkenyl, alkoxy or thio alkoxy group, or is selected from aromatic hydrocarbons or condensed-nuclei aromatics, heterocyclic arene or condensed hetero ring aromatic hydrocarbons.The present invention also provides above-mentioned general formula compounds.Organic electroluminescence device of the invention opens the aspect of performance such as bright voltage and service life in luminous efficiency, device and all obtains significantly raising and improvement.
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.
What the generation of organic electroluminescent was leaned on is the weight of the carrier (electrons and holes) transmitted in organic electroluminescence material
Group, it is well known that the electric conductivity of organic material is very poor, does not have continuity unlike inorganic semiconductor, in organic semiconductor
Energy band, the transmission of carrier is commonly used jump theory and is described, i.e., under the driving of an electric field, electronics is being excited or is injected into point
In the lumo energy of son, achieve the purpose that charge is transmitted via the lumo energy for jumping to another molecule.In order to make have
Organic electroluminescence devices reach breakthrough in application aspect, it is necessary to overcome the difficulty of the injection of organic material charge and transmittability difference.
Scientists are by the adjustment of device architecture, such as increase the number of device organic material layer, and play the part of different organic layers
Different roles is drilled, such as the functional material having helps electronics to inject from cathode and hole from anode, some materials help electricity
The transmission of lotus, the material played the role of, which then plays, stops electronics and hole transport, most important certainly in organic electroluminescent
The luminescent material of various colors will also achieve the purpose that match with adjacent functional material, the Organic Electricity of excellent in efficiency service life length
Electroluminescence device is usually the optimization collocation of device architecture and various organic materials as a result, this is just that chemists design out
The functionalization material for sending out structure various provides great opportunities and challenges.
There are many factor for influencing OLED performance, and wherein luminescent material is the core and key of OLED.First generation OLED shines
Material is small molecule fluorescent material, and this kind of material category is abundant, and stability is good, but this material can only be sent out using singlet
Light, and it is singlet that the exciton generated under electroexcitation, which only has 25%, therefore low efficiency.In order to improve efficiency, Forrest etc.
It proposes phosphor material within people 1998, using the spin-orbit cou-pling effect of heavy atom triplet excitons is shone at room temperature, it is real
The utilization of exciton 100% is showed.But also due to the presence of heavy atom, this kind of material price is higher, meanwhile, blue
The life problems of phosphor material never solve.Therefore, people are also trying to explore novel luminescent material.Currently, most having
Prospect is thermal activation delayed fluorescence material, is also TADF material.Under the singlet and triplet state energy gap difference of this material are ruthless,
In environment under the action of heat, non-luminous triplet excitons can return to singlet emitter by altering more process between inverse system,
To realize that 100% exciton utilizes.This phenomenon is to find in also eosine in 1961, while early stage matches in copper earliest
Species are closed also to have been reported that.Adachi of Kyushu University et al. improves pure small organic molecule by design of material in recent years
The efficiency of TADF device, so that this technology is of interest by researcher.
Summary of the invention
The object of the present invention is to provide a kind of organic electroluminescence device high with high-luminous-efficiency and excitation purity,
A kind of luminescent material for realizing the organic electroluminescence device is provided.
The present invention provides a kind of organic electroluminescence device, including first electrode, second electrode and it is located at described first
One or more layers organic layer between electrode and second electrode, comprising at least one by the following general formula (I) institute in the organic layer
The compound shown:
In above-mentioned logical formula (I):
R1Selected from cyano or hydrogen；L is selected from C6~C30Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C30's
Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；Ar is selected from containing oxygen atom or sulphur atom and C3~C40Substitution
Or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
Substituent group on the L or Ar is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkanes
Base, alkenyl, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, contain
There are hetero atom and C selected from N, O, S, Si6~C30Mononuclear aromatics or condensed-nuclei aromatics group.
Further, L is selected from C6~C15Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C15Substitution or
Unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；Ar is selected from containing oxygen atom or sulphur atom and C3~C15Substitution or do not take
The heteroaryl or condensed hetero ring aromatic hydrocarbon group in generation；Substituent group on the L or Ar is independently selected from fluorine, cyano, nitro, or is selected from C1
~C6Alkyl or cycloalkyl, alkenyl, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C15Monocycle virtue
Hydrocarbon or condensed-nuclei aromatics group, containing being hetero atom and C selected from N or O6~C15Mononuclear aromatics or condensed-nuclei aromatics group.
Specifically, when the above-mentioned L or Ar of definition is respectively and independently selected from aryl, refer to selected from certain amount ring skeleton carbon
Aromatics ring system of atom, including single ring architecture substituent group such as phenyl etc. also include the aromatic ring substituents for being covalently attached structure
Group is such as xenyl, terphenyl.
Specifically, refer to when defining above-mentioned L or Ar and being respectively and independently selected from condensed-nuclei aromatics group with certain amount ring bone
Aromatics ring system of frame carbon atom, including condensed cyclic structure substituent group such as naphthalene, anthryl etc. also include condensed cyclic structure substituent group
Building stone being connected with single ring architecture aryl such as benzene binaphthyl, naphthalene xenyl, biphenyl dianthranide base etc., further includes covalently connecting
The thick aromatic ring substituents of binding structure are rolled into a ball such as binaphthyl.
Further, the L in general formula (I) preferably is selected from following group:
Ar in general formula (I) preferably is selected from following group:
Further, the preferred example as organic electroluminescence device of the invention can be enumerated and select following representatives
Organic electroluminescence device of the property compound A1~A76 as luminescent material.
Present invention simultaneously provides one kind by the following general formula (I) compound represented:
In formula (I):
R1Selected from cyano or hydrogen；L is selected from C6~C30Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C30's
Substituted or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；Ar is selected from containing oxygen atom or sulphur atom and C3~C40Substitution
Or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
Substituent group on the L or Ar is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkanes
Base, alkenyl, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, contain
There are hetero atom and C selected from N, O, S, Si6~C30Mononuclear aromatics or condensed-nuclei aromatics group.
Further, L is selected from C6~C15Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C15Substitution or
Unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；Ar is selected from containing oxygen atom or sulphur atom and C3~C15Substitution or do not take
The heteroaryl or condensed hetero ring aromatic hydrocarbon group in generation；
Substituent group on the L or Ar is independently selected from fluorine, cyano, nitro, or is selected from C1~C6Alkyl or cycloalkyl,
Alkenyl, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C15Mononuclear aromatics or condensed-nuclei aromatics group, contain
Having selected from N or O is hetero atom and C6~C15Mononuclear aromatics or condensed-nuclei aromatics group.
Further, R1For cyano, L is selected from following group:
Ar is selected from following group:
Further, in logical formula (I) of the invention, the chemical combination that the compound of following specific structures indicates can preferably be gone out
Object: these compounds are only representative.
Organic electroluminescence device of the invention has excellent photoelectricity performance, have relatively low device rise it is bright and
Operating voltage, while there is relatively high device efficiency, and device lasts a long time.
The compounds of this invention especially selects acenaphthene and pyrazine structure as parent nucleus group, and contains oxygen atom or sulphur atom in this way
Heteroatomic heteroaryl groups such as furans, thiophene-based heteroatom group connect, there is chemical stability well, increase device
The service life of part, furthermore such substituent group connect with parent nucleus after its LUMO and the overlapping region HOMO reduce, enable HOMO and LUMO
Gap becomes larger, and the T1 for being embodied in material increases, and becomes smaller so that the energy between T1 and S1 is very poor, so that T1 between inverse system by wearing
S1 is more transferred energy to, and then luminous (TADF property) proposes high molecular luminous efficiency.
Bright voltage and service life etc. are opened in luminous efficiency, device using the organic electroluminescence device of general formula compound of the present invention
Aspect of performance, which all obtains, significantly to be improved and improves.
Specific embodiment
In order to make those skilled in the art more fully understand the present invention, With reference to embodiment to the present invention make into
One step is described in detail.
The compound for the synthetic method that do not mention in embodiment is all the raw produce being obtained through commercial channels.
The present invention is more specifically described referring to the following examples, but the invention is not limited to these embodiments.
In the present invention, the synthetic method of the public parent nucleus of preferred compound is as follows:
By 5- bromine acenaphthenequinone (26.1g, 0.1mol), diaminomaleonitrile (13g, 0.12mol), p-methyl benzenesulfonic acid (51.2g)
It is added in 500ml ethyl alcohol, is added and causes back flow reaction 5h, TLC monitors fully reacting, cooled and filtered, and filter cake washs 2 with methanol
After secondary, toluene: ethyl alcohol=1:1 recrystallizes to obtain yellow solid 25g, yield: 75.2%.1H NMR(500MHz,Chloroform)δ
8.08 (dd, J=7.5,1.4Hz, 1H), 8.00 (d, J=7.5Hz, 1H), 7.84 (dd, J=7.5,1.4Hz, 1H), 7.66 (t,
J=7.5Hz, 1H), 7.55 (d, J=7.5Hz, 1H)
By 5- bromine acenaphthenequinone (26.1g, 0.1mol), ethylenediamine (13g, 0.12mol) is added in 200ml acetic acid, and heating causes
Back flow reaction 5h, TLC monitor fully reacting, and cooled and filtered filters, toluene after being added to the water: ethyl alcohol=1:1 recrystallizes yellow
Color solid 19.4g, yield: 68.5%.1H NMR (500MHz, Chloroform) δ 8.60 (s, 2H), 8.08 (dd, J=7.5,
1.4Hz, 1H), 7.97 (d, J=7.5Hz, 1H), 7.84 (dd, J=7.5,1.4Hz, 1H), 7.66 (t, J=7.5Hz, 1H),
7.55 (d, J=7.5Hz, 1H)
The synthesis of intermediate
By M2 (28.3g, 0.1mol), connection pinacol borate (38g, 0.15mol), potassium acetate (19.6g, 0.2mol),
Pd (dppf) Cl2 (0.2g), dioxane 300ml are added in reaction flask, are heated to back flow reaction 4h, and TLC monitoring has been reacted
At rear cooling, be added water and ethyl acetate extraction, the brown solid after organic phase concentration, filter after ethanol washing M2-1 class is white
Color solid 27g, yield 82%.
By M2-1 (33g, 0.1mol), tetra-triphenylphosphine palladium (0.5g), bromo-iodobenzene (28.3g, 0.1mol), potassium carbonate
(21g, 0.15mol) dioxane 300ml, water 50ml, be added reaction flask be heated to back flow reaction, after the reaction was completed be added water and
After ethyl acetate extraction, organic phase is concentrated to give intermediate M31H NMR(500MHz,Chloroform)δ8.60(s,2H),7.76
(d, J=7.5Hz, 1H), 7.67 (d, J=7.5Hz, 2H), 7.62 (dt, J=7.3,1.4Hz, 1H), 7.51-7.42 (m, 3H),
7.43–7.33(m,2H).
With described above, difference is bromine iodine the intermediate synthetic method used in all preferred compounds of the present invention
Benzene is substituted for the halides of equivalent, shown in table specific as follows:
Synthetic example 1.
The synthesis of A1
By M3 (18g, 0.05mol), tetra-triphenylphosphine palladium (0.2g), 6- phenyl dibenzofurans -4- boric acid (15g,
0.051mol), potassium carbonate (13.8g, 0.1mol) dioxane 300ml, water 50ml is added reaction flask and is heated to back flow reaction,
After water and ethyl acetate extraction are added after the reaction was completed, organic phase is concentrated to give crude product, the yellowish solid A1 after re crystallization from toluene
。1H NMR (500MHz, Chloroform) δ 8.60 (s, 2H), 8.30 (t, J=2.9Hz, 1H), 8.10 (d, J=3.1Hz,
1H), 8.07 (d, J=3.1Hz, 1H), 8.03 (t, J=5.2Hz, 1H), 8.01 (d, J=2.9Hz, 1H), 7.80-7.57 (m,
6H),7.55–7.33(m,9H).
With synthetic example 1, difference is 6- phenyl dibenzofurans -4- boron the synthetic method of other preferred compounds
Acid replaces with the boric acid compound of equivalent, shown in table 1 specific as follows, wherein the boric acid compound used can pass through
It is bought in domestic Chemical market.
Table 1:
Structure identification and analysis, each synthetic example characterization of compound data have been carried out to material using MS and elemental analysis
It is specifically shown in the following table 2:
Table 2:
Device embodiments:The structure of organic electroluminescence device in device embodiments of the present invention are as follows: according to " sun on substrate
Pole/hole injection layer (HIL)/hole transmission layer (HTL)/luminescent layer (EL)/electron transfer layer (ETL)/electron injecting layer
(EIL) sequence of/cathode " is laminated, and each layer is made of following material；
ITO/2-TNATA (30nm)/NPB (20nm)/general formula (1) compound: Ir (ppy)3(5%) (20nm)/BPhen
(50nm)/LiF(1nm)/Al。
Emitting layer material uses green phosphorescent coloring Ir (ppy)3Dyestuff, collocation main body are general formula of the present invention (1) compound.Respectively
Functional layer material molecular structure is as follows:
1. compound A1 of device embodiments is as light emitting host material
Organic electroluminescence device preparation process is as follows in the present embodiment:
The glass substrate that surface is coated with transparent conductive film is cleaned by ultrasonic in cleaning solution, in deionized water
Ultrasonic treatment, in acetone: ultrasonic oil removing in alcohol mixed solvent (volume ratio 1: 1) mixed solution is baked under clean environment
Moisture is completely removed, is performed etching with ultraviolet lamp and ozone treatment, and with low energy cation beam 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
Vacuum evaporation 2-TNATA is as hole injection layer on anode tunic, and evaporation rate 0.1nm/s, vapor deposition total film thickness is 40nm；So
Hole transmission layer NPB, evaporation rate 0.1nm/s are deposited afterwards, vapor deposition film thickness is 10nm；
Luminescent layer of the vacuum evaporation EML as device on hole transmission layer, EML include material of main part and dyestuff material
A1 as luminous layer main body is placed in the cell of vacuum phase deposition equipment, will be made by material, the method steamed altogether using multi-source
For (ppy) of dopant3Ir is placed in another room of vacuum phase deposition equipment, is adjusted material of main part A1 evaporation rate and is
The concentration of 0.1nm/s, Ir (ppy) 3 is 10%, and vapor deposition total film thickness is 20nm；
Vacuum evaporation Bphen forms the electron transfer layer that film thickness is 50nm, evaporation rate 0.1nm/ on the light-emitting layer
s；
On the electron transport layer successively vacuum evaporation with a thickness of 1nm LiF as electron injecting layer, with a thickness of 150nm's
The Al layers of cathode as device.
2. the compounds of this invention A4 of device embodiments is as light emitting host material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound A1ization
It closes object and replaces with compound A7.
3. the compounds of this invention A7 of device embodiments is as light emitting host material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound A1 is replaced
It is changed to compound A14.
4. the compounds of this invention A10 of device embodiments is as light emitting host material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound A1 is replaced
It is changed to compound A16.
5. the compounds of this invention A14 of device embodiments is as light emitting host material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound A1 is replaced
It is changed to compound A19.
6. the compounds of this invention A16 of device embodiments is as light emitting host material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound A1 is replaced
It is changed to compound A22.
7. the compounds of this invention A19 of device embodiments is as light emitting host material
Organic electroluminescence device is prepared using method same as Example 1, difference is, by compound A1ization
It closes object and replaces with compound A28.
8. the compounds of this invention A22 of device embodiments is as light emitting host material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound A1 is replaced
It is changed to compound A-13 4.
Device comparative example 1.CPB is as light emitting host material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound A1 is replaced
It is changed to compound CPB.
Device comparative example 2.Comp2 is as light emitting host material
Organic electroluminescence device is prepared using method same as Example 1, difference is, compound A1 is replaced
It is changed to compound Comp2.
Under same brightness, use 2602 digital sourcemeter luminance meter of Keithley (photoelectric instrument factory, Beijing Normal University)
The driving voltage of organic electroluminescence device that is prepared in measurement device embodiments 1-12 and device comparative example 1 and 2 and
Current efficiency the results are shown in Table 3.
Concrete preferred structure compound disclosed in device embodiments of the present invention is applied in organic electroluminescence device
Device performance detection data is detailed in the following table 3:
Table 3:
The device performance data of the device embodiments 1-8 as disclosed in table 3 are as it can be seen that in organic electroluminescence device structure
In the identical situation of other materials, the adjustment of EML material in the devices, the device that compares is to 1, the present invention and existing common used material
It is greatly improved compared in terms of the voltage efficiency service life, to 2, the present invention mainly obtains in terms of device lifetime bright the device that compares
It raising, this also matches with thinking of the present invention.
Device embodiments 1~8 are compared to device comparative example 2, other organic function layer materials in same device architecture
Expect in identical situation, using series compound of the present invention as luminescent layer material of main part, device luminescent properties are obviously improved, this
Superiority of the compounds of this invention relative to compound Comp2 is absolutely proved.
The preferred embodiment of the present invention has been described above in detail, still, during present invention is not limited to the embodiments described above
Detail within the scope of the technical concept of the present invention can be with various simple variants of the technical solution of the present invention are made, this
A little simple variants all belong to the scope of protection of the present invention.
It is further to note that specific technical features described in the above specific embodiments, in not lance
In the case where shield, can be combined in any appropriate way, in order to avoid unnecessary repetition, the present invention to it is various can
No further explanation will be given for the combination of energy.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should also be regarded as the disclosure of the present invention.
Claims (8)
1. a kind of organic electroluminescence device, including first electrode, second electrode and it is located at the first electrode and second electrode
Between one or more layers organic layer, comprising at least one by the following general formula (I) compound represented in the organic layer:
In formula (I):
R1Selected from cyano or hydrogen；L is selected from C6~C30Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C30Substitution
Or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；Ar is selected from containing oxygen atom or sulphur atom and C3~C40Substitution or not
Substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
Substituent group on the L or Ar is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, alkene
Base, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing choosing
From the hetero atom and C of N, O, S, Si6~C30Mononuclear aromatics or condensed-nuclei aromatics group.
2. organic electroluminescence device according to claim 1, in the formula (I):
L is selected from C6~C15Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C15Substituted or unsubstituted heteroaryl
Base or condensed hetero ring aromatic hydrocarbon group；Ar is selected from containing oxygen atom or sulphur atom and C3~C15Substituted or unsubstituted heteroaryl or
Condensed hetero ring aromatic hydrocarbon group；
Substituent group on the L or Ar is independently selected from fluorine, cyano, nitro, or is selected from C1~C6Alkyl or cycloalkyl, alkenyl,
C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C15Mononuclear aromatics or condensed-nuclei aromatics group, containing being selected from
N or O is hetero atom and C6~C15Mononuclear aromatics or condensed-nuclei aromatics group.
3. organic electroluminescence device according to claim 1, in the formula (I), the L is selected from following group:
The Ar is selected from following group:
4. organic electroluminescence device according to claim 1, the compound is selected from following concrete structure formulas:
5. one kind is by the following general formula (I) compound represented:
In formula (I):
R1Selected from cyano or hydrogen；L is selected from C6~C30Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C30Substitution
Or unsubstituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；Ar is selected from containing oxygen atom or sulphur atom and C3~C40Substitution or not
Substituted heteroaryl or condensed hetero ring aromatic hydrocarbon group；
Substituent group on the L or Ar is independently selected from halogen, cyano, nitro, or is selected from C1~C10Alkyl or cycloalkyl, alkene
Base, C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C30Mononuclear aromatics or condensed-nuclei aromatics group, containing choosing
From the hetero atom and C of N, O, S, Si6~C30Mononuclear aromatics or condensed-nuclei aromatics group.
6. compound according to claim 5, in the formula (I):
L is selected from C6~C15Substituted or unsubstituted aryl or condensed-nuclei aromatics group, C3~C15Substituted or unsubstituted heteroaryl
Base or condensed hetero ring aromatic hydrocarbon group；Ar is selected from containing oxygen atom or sulphur atom and C3~C15Substituted or unsubstituted heteroaryl or
Condensed hetero ring aromatic hydrocarbon group；
Substituent group on the L or Ar is independently selected from fluorine, cyano, nitro, or is selected from C1~C6Alkyl or cycloalkyl, alkenyl,
C1~C6Alkoxy or thio alkoxy group, or be selected from C6~C15Mononuclear aromatics or condensed-nuclei aromatics group, containing being selected from
N or O is hetero atom and C6~C15Mononuclear aromatics or condensed-nuclei aromatics group.
7. compound according to claim 5, in the formula (I),
L is selected from following group:
Ar is selected from following group:
8. being selected from following concrete structure formulas according to the compound any in claim 5 or 6:
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| CN106083824A (en) * | 2016-06-08 | 2016-11-09 | 中节能万润股份有限公司 | Organic photoelectrical material and include the organic electroluminescence device of this organic material |
| KR20170065974A (en) * | 2015-12-04 | 2017-06-14 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
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| KR20170065974A (en) * | 2015-12-04 | 2017-06-14 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| CN106083824A (en) * | 2016-06-08 | 2016-11-09 | 中节能万润股份有限公司 | Organic photoelectrical material and include the organic electroluminescence device of this organic material |
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Application publication date: 20190607 |