CN104037339A - Organic electroluminescence device - Google Patents
Organic electroluminescence device Download PDFInfo
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- CN104037339A CN104037339A CN201410293365.8A CN201410293365A CN104037339A CN 104037339 A CN104037339 A CN 104037339A CN 201410293365 A CN201410293365 A CN 201410293365A CN 104037339 A CN104037339 A CN 104037339A
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
Abstract
The invention provides an organic electroluminescence device. The organic electroluminescence device comprises an anode, a cathode and an organic layer; the organic layer comprises one or more of a hole injection layer, a hole transmission layer, a lighting layer, a barrier layer, an electron injection layer and an electron transmission layer. The organic electroluminescence device is characterized in that at least one layer in the organic layer contains a compound as shown in the structural formula (I). Structural formula is as shown in specification.
Description
Technical field
The present invention relates to technical field of organic electroluminescence, relate to specifically a kind of organic electroluminescence device.
Background technology
Organic electroluminescence device (OLEDs) for being steamed and crossed the device that deposition one deck organic material is prepared from by spin coating or vacuum between two metal electrodes, three layers of classical organic electroluminescence device comprise hole transmission layer, luminescent layer and electron transfer layer.The hole being produced by anode is followed the electronics being produced by negative electrode to be combined in luminescent layer through electron transfer layer and is formed exciton through hole transmission layer, then luminous.Organic electroluminescence device can regulate the light of the various needs of transmitting as required by changing the material of luminescent layer.
Organic electroluminescence device is as a kind of novel Display Technique, have that self-luminous, wide visual angle, low energy consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible and the transparent particular advantages such as display floater and environmental friendliness, can be applied in flat-panel monitor and a new generation's illumination above, also can be used as the backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially application to some extent, and such as the screen such as camera and mobile phone, but current OLED device is because efficiency is low, the factors such as useful life is short restrict it and apply widely, particularly large screen display.And restrict the performance that one of them key factor is exactly the electroluminescent organic material in organic electroluminescence device.Because OLED device is applying voltage-operated time, can produce Joule heat in addition, make organic material that crystallization easily occur, affect life-span and the efficiency of device, therefore, also need to develop the electroluminescent organic material of stability and high efficiency.
In organic electroluminescence device, the introducing of hole mobile material and injection material, can reduce positive charge and be transferred to from positive pole the ability of luminescent layer effectively, improves the efficiency of device and thermally-stabilised.Traditional hole-injecting material, as copper phthalocyanine (CuPc), degraded is slow, and preparation power consumption is high, is unfavorable for environmental protection, and it can absorb light, affects the efficiency of device.The hole mobile material that NPB etc. are original, thermal stability is poor, also largely affects device lifetime.Thereby, need to develop the electroluminescent organic material of efficient stable.
Summary of the invention
First the present invention provides a kind of hole transport compound based on fluorenes, and it is for having the compound of following structural formula (I):
Wherein, Ar
1, Ar
2, Ar
3, Ar4, Ar5, Ar6, Ar7 be respectively independently selected from replacement or the unsubstituted heteroaryl of the replacement of hydrogen, C1-C12 alkyl, C1-C8 alkoxyl, C6-C60 or unsubstituted aryl, C3-C60;
Wherein preferred mode is:
Ar
1the phenyl that replaces for phenyl, by C1-C4 alkyl, naphthyl, the naphthyl being replaced by C1-C4 alkyl, xenyl, the xenyl, (9 being replaced by C1-C4 alkyl, 9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl;
Ar
2, Ar3 is respectively independently selected from C1-C8 alkyl, phenyl, the phenyl being replaced by C1-C4 alkyl, naphthyl, the naphthyl being replaced by C1-C4 alkyl, xenyl, the xenyl that replaced by C1-C4 alkyl;
Ar
4, Ar
5, Ar
6and Ar
7respectively independently selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, triaromatic amine base, carbazyl;
Wherein said phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, triaromatic amine base, carbazyl can further be replaced by the alkyl of C1-C4.
Further preferred mode is:
Ar
1be selected from phenyl, naphthyl, xenyl, tolyl;
Ar
2with Ar3 respectively independently selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl, xenyl, tolyl;
Ar
4, Ar
5, Ar
6, Ar
7respectively independently selected from following aryl and heteroaryl or the following aryl or the heteroaryl that are replaced by C1-C4 alkyl:
Further preferred, a kind of hole transport compound based on fluorenes of the present invention, is following structural 1
-34 compound
Hole transport compound based on fluorenes of the present invention can pass through Friedel-Crafts reaction, and Suzuki coupling and Buchwald-Hartwig reaction prepare.
Hole transport compound based on fluorenes of the present invention can be applied in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, organic layer comprises one or more layers in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer and electron transfer layer, has at least one deck to contain just like organic electroluminescent compounds structural formula (I) Suo Shu in wherein said organic layer:
Wherein Ar
1-Ar
7definition as previously mentioned;
Wherein organic layer is luminescent layer and hole transmission layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer;
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer;
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer;
Wherein the layer at the hole transport compound place based on fluorenes as described in structural formula (I) is hole transmission layer or hole injection layer;
Wherein the hole transport compound based on fluorenes as described in structural formula (I) is the compound of structural formula 1-34.
The hole transport compound based on fluorenes as described in structural formula I can use separately, also can use with other compound; The hole transport compound based on fluorenes as described in structural formula I can use separately a kind of compound wherein, also can use two or more the compound in structural formula I simultaneously.
Organic electroluminescence device of the present invention, further preferred mode is, this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein in hole transmission layer, contains the compound of structural formula (I); Further preferred, the compound in hole transmission layer is the compound of structural formula 1-34.
The gross thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
Organic electroluminescence device of the present invention is in the time using the present invention to have the compound of structural formula I, can use collocation other materials, as hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer etc., and obtain blue light, green glow, gold-tinted, ruddiness or white light.
The hole transmission layer of organic electroluminescence device of the present invention and hole injection layer, material requested has good hole transport performance, can effectively hole be transferred to luminescent layer from anode.Have the described compound of structural formula (I) except above-mentioned, can also comprise other little molecule and macromolecular organic compounds, include but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the assorted triphen (hexanitrilehexaazatriphenylene), 2 of six cyano group six, 3,5,6-tetrafluoro-7,7', 8,8'-, tetra-cyanogen dimethyl 1,4-benzoquinone (F4-TCNQ), Polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the present invention, has the good characteristics of luminescence, can regulate as required the scope of visible ray.Except containing compound of fluorene class of the present invention, can also contain following compound, include, but are not limited to naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, bend compounds, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, the organic phosphorescence complex compound of metal is (as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-organosilicon compound, the organic polymer luminescent materials such as polythiophene, they can use separately, also can use by multiple mixture.The thickness of luminescent layer is preferably 10-50nm.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires to have good electronic transmission performance, can, effectively during electronics is from cathode transport to luminescent layer, have very large electron mobility.Can select following compound, but be not limited to this, oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocycle compound, quinolines, ferrosin compounds, metallo-chelate (as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
The electron injecting layer of organic electroluminescence device of the present invention, can effectively electronics be injected into organic layer from negative electrode, mainly be selected from alkali metal or alkali-metal compound, or be selected from compound or the alkali metal complex of alkaline-earth metal or alkaline-earth metal, can select following compound, but be not limited to this, oxide or halide, the oxide of rare earth metal or the organic complex of halide, alkali metal or alkaline-earth metal of the oxide of alkali metal, alkaline-earth metal, rare earth metal, alkali gold brush or halide, alkaline-earth metal; Be preferably lithium, lithium fluoride, lithia, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesium oxide, these compounds can use separately also and can use by mixture, also can be used in conjunction with other electroluminescent organic materials.
Every one deck of organic layer in organic electroluminescence device of the present invention, can steam the modes such as the method for crossing, molecular beam vapour deposition method, the dip coating that is dissolved in solvent, spin-coating method, excellent painting method or inkjet printing and prepare by vacuum.Can use vapour deposition method or sputtering method to be prepared for metal motor.
Device experimental shows, the hole transport compound based on fluorenes of the present invention as described in structural formula (I), has better thermal stability, high-luminous-efficiency, high luminance purity, low driving voltage.The organic electroluminescence device that adopts this hole transport compound based on fluorenes to make have advantages of the good and colorimetric purity excellence of electroluminescent efficiency and the life-span long.
Brief description of the drawings
Fig. 1 is the hydrogen nuclear magnetic spectrogram of compound 1.
Fig. 2 is the hydrogen nuclear magnetic spectrogram of compound 33.
Fig. 3 is a kind of organic electroluminescence device structural representation of the present invention
Wherein, 110 are represented as glass substrate, and 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as luminescent layer, and 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Fig. 4 is that embodiment 3 is at 20mA/cm
2current density under emission spectrum.
Embodiment
In order more to describe the present invention in detail, especially exemplified by following example, but be not limited to this.
Embodiment 1
Synthesizing of compound 1
Compound 1-1's is synthetic
In reaction bulb, add Fluorenone (9g, 50mmol) and water (30ml), be heated to 80 DEG C, in reaction bulb, slowly add bromine (8.8g, 55mmol), react 4 hours, add 100ml water and 100ml10% aqueous solution of sodium bisulfite.Filter, the solid obtaining obtains 11g product with absolute ethyl alcohol recrystallization, and productive rate is 85%.
Compound 1-2's is synthetic
In reaction bulb, add compound 1-1 (2.58g, 10mmol) with 15ml oxolane, at 0 DEG C, drip the phenyl-magnesium-bromide RMgBr (12mmol) that is dissolved in oxolane, add and slowly rise to room temperature reaction 12 hours, add watery hydrochloric acid to regulate PH=7, be extracted with ethyl acetate, with anhydrous magnesium sulfate drying, except desolventizing, thick product obtains white solid 2.3g solid, productive rate 89% with silica gel column chromatography.
1H?NMR(400MHz,CDCl
3)δ7.67-7.69(d,J＝7.6Hz,2H),7.33-7.41(m,6H),7.24-7.29(m,5H),2.51(s,1H)。
Compound 1-3's is synthetic
In reaction bulb, add compound 1-2 (1.1g, 3.3mmol), triphenylamine (1.5g, 6.1mmol) and 15ml carrene, stir the boron trifluoride ether solution that drips 5 under room temperature.React 2 hours, drip ethanol quencher reaction, except desolventizing, thick product obtains white solid 1g white solid, productive rate 56% with silica gel column chromatography.
1H?NMR(400MHz,CDCl
3)δ7.71-7.73(d,J＝7.6Hz,1H)，7.61-7.63(d,J＝8Hz,1H)7.47-7.53(m,2H),7.20-7.40(m,12H),6.90-7.08(m,10H).
Synthesizing of compound 1
In reaction bulb, add compound 1-3 (560mg, 1mmol); aniline (30mg; 0.32mmol), potassium tert-butoxide (330mg, 3mmol); palladium (10mg); the toluene of 2-(dicyclohexyl phosphorus)-biphenyl (30mg) and 10ml is added to 80 DEG C of reactions 4 hours under nitrogen protection, cooling, except desolventizing; thick product obtains white solid 250mg solid, productive rate 74% with silica gel column chromatography.
1h NMR (400MHz, DMSO) δ 7.76-7.79 (m, 4H), 7.35-7.42 (m, 4H), 7.12-7.29 (m, 18H), 6.89-6.94 (m, 27H), 6.75-6.81 (m, 4H) .ESI, m/z:[M+H]+: 1060.5. nuclear magnetic spectrogram is shown in Fig. 1.
Embodiment 2
Synthesizing of compound 33
In reaction bulb, add compound 1-3 (550mg, 0.97mmol); naphthalidine (58mg; 0.41mmol), potassium tert-butoxide (330mg, 3mmol); palladium (10mg); the toluene of 2-(dicyclohexyl phosphorus)-biphenyl (30mg) and 10ml is added to 80 DEG C of reactions 4 hours under nitrogen protection, cooling, except desolventizing; thick product obtains white solid 215mg solid, productive rate 47% with silica gel column chromatography.
1h NMR (400MHz, CDCl
3) δ 7.75-7.78 (m, 2H), 7.67-7.69 (d, J=8.4Hz, 1H), 7.59-7.62 (m, 2H), 7.46-7.48 (m, 2H), 6.99-7.36 (m, 44H), 6.76-6.88 (m, 8H). nuclear magnetic spectrogram is shown in Fig. 2.
Embodiment 3
The preparation of organic electroluminescence device
Use the compound of embodiment 1 to prepare OLED
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, steam and cross compound 1, form the thick hole transmission layer 130 of 60nm.
Then, on hole transmission layer, steam and cross the compd A lq that 30nm is thick
3as luminescent layer 140.
Then, on luminescent layer, steam and cross the Alq that 20nm is thick
3as electron transfer layer 150.
Finally, steam that to cross 1nm LiF be that electron injecting layer 160 and 100nm Al are as device cathodes 170.
Prepared device records at 7mA/cm with Photo Research PR650 spectrometer
2current density under driving voltage be 3V, Fig. 4 represents that the organic electroluminescence device of the present embodiment is at 20mA/cm
2current density under emission spectrum, be green spectral.
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, steam and cross NPB, form the thick hole transmission layer 130 of 60nm.
Then, on hole transmission layer, steam and cross the Alq that 30nm is thick
3as luminescent layer 140.
Then, on luminescent layer, steam and cross the Alq that 20nm is thick
3as electron transfer layer 150.
Finally, steam that to cross 1nm LiF be that electron injecting layer 160 and 100nm Al are as device cathodes 170.
Prepared device records at 7mA/cm with Photo Research PR650 spectrometer
2current density under driving voltage be 4.5V, transmitting green light
Under identical condition, apply the driving voltage of organic electroluminescence device prepared by organic electroluminescent compounds of the present invention lower than comparative example.As mentioned above, compound of the present invention has high stability, and organic electroluminescence device prepared by the present invention has low driving voltage, high efficiency and optical purity.
Structural formula described in device
。
Claims (9)
1. an organic electroluminescence device, it comprises anode, negative electrode and organic layer, organic layer comprises one or more layers in hole injection layer, hole transmission layer, luminescent layer, barrier layer, electron injecting layer and electron transfer layer, it is characterized in that in organic layer that one deck at least includes the compound of following structural formula (I):
Wherein, Ar
1, Ar
2, Ar
3, Ar
4, Ar
5, Ar
6, Ar
7respectively independently selected from replacement or the unsubstituted heteroaryl of the replacement of hydrogen, C1-C12 alkyl, C1-C8 alkoxyl, C6-C60 or unsubstituted aryl, C3-C60.
2. organic electroluminescence device according to claim 1, is characterized in that wherein
Ar
1the phenyl that replaces for phenyl, by C1-C4 alkyl, naphthyl, the naphthyl being replaced by C1-C4 alkyl, xenyl, the xenyl, (9 being replaced by C1-C4 alkyl, 9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl;
Ar
2, Ar
3respectively independently selected from C1-C8 alkyl, phenyl, the phenyl being replaced by C1-C4 alkyl, naphthyl, the naphthyl being replaced by C1-C4 alkyl, xenyl, the xenyl that replaced by C1-C4 alkyl;
Ar
4, Ar
5, Ar
6and Ar
7respectively independently selected from phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, triaromatic amine base, carbazyl;
Wherein said phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, triaromatic amine base, carbazyl can further be replaced by the alkyl of C1-C4.
3. organic electroluminescence device according to claim 1, wherein:
Ar
1be selected from phenyl, naphthyl, xenyl, tolyl;
Ar
2and Ar
3respectively independently selected from methyl, ethyl, propyl group, isopropyl, the tert-butyl group, normal-butyl, n-hexyl, phenyl, naphthyl, xenyl, tolyl;
Ar
4, Ar
5, Ar
6, Ar
7respectively independently selected from following aryl and heteroaryl or the following aryl or the heteroaryl that are replaced by C1-C4 alkyl:
4. organic electroluminescence device according to claim 1, wherein the compound of structural formula (I) is the compound of following structural 1-34
5. organic electroluminescence device according to claim 1, one or more layers in hole transmission layer or hole injection layer of the layer that it is characterized in that compound place as described in structural formula (I).
6. organic electroluminescence device according to claim 1, is characterized in that the compound as described in structural formula (I) can use separately, also can use with other compound.
7. organic electroluminescence device according to claim 1, it is characterized in that the compound as described in structural formula (I) can use separately a kind of compound wherein, also can use two or more the compound in structural formula (I) simultaneously.
8. organic electroluminescence device according to claim 1, it comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, it is characterized in that the compound that contains structural formula (I) in hole transmission layer.
9. organic electroluminescence device according to claim 8, is characterized in that the compound in hole transmission layer is the compound of structural formula 1-34.
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| WO2016184540A1 (en) * | 2015-05-18 | 2016-11-24 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| KR20200031358A (en) * | 2018-09-14 | 2020-03-24 | 주식회사 엘지화학 | Manufacturing method of organic compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2016184540A1 (en) * | 2015-05-18 | 2016-11-24 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| CN107635987A (en) * | 2015-05-18 | 2018-01-26 | 默克专利有限公司 | Material for organic electroluminescence device |
| JP2018524280A (en) * | 2015-05-18 | 2018-08-30 | メルク パテント ゲーエムベーハー | Materials for organic electroluminescent devices |
| US10629817B2 (en) | 2015-05-18 | 2020-04-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| CN107635987B (en) * | 2015-05-18 | 2023-01-03 | 默克专利有限公司 | Material for organic electroluminescent device |
| KR20200031358A (en) * | 2018-09-14 | 2020-03-24 | 주식회사 엘지화학 | Manufacturing method of organic compound |
| KR102648147B1 (en) * | 2018-09-14 | 2024-03-14 | 주식회사 엘지화학 | Manufacturing method of organic compound |
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