CN109422757A - A kind of delayed fluorescence material and preparation method and organic electroluminescence device - Google Patents
A kind of delayed fluorescence material and preparation method and organic electroluminescence device Download PDFInfo
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Abstract
The present invention is by the electron-donating group of dibenzo indole carbazole, the electron-withdrawing group for connecting pyridine (pyridine), diphenylpyrimidin (diphenylpyrimidine) or diphenyl triazine (diphenyl triazine) connects the delayed fluorescence compound that substituted or non-substituted benzene or naphthalene nucleus combine composition.
Description
Technical field
The present invention relates to field of organic electroluminescence more particularly to a kind of delayed fluorescence compound and preparation method thereof and make
The organic electroluminescence device prepared with the material.
Background technique
Recently with the enlargement for indicating device, the demand of the flat display few to space occupancy is improved, is had
Machine light emitting diode is also one of those, be referred to as organic light emission original part (organic light emitting diode:
OLED the technology of Organic Light Emitting Diode) is also in high speed development.
Organic light-emitting diode element is formed between electron injection electrode (cathode) and hole injecting electrode (anode)
Electrons and holes are injected from anode and cathode in luminescent substance layer, are eliminated after in pairs and luminous original part.It not only can be in picture
Element is formed on flexible (flexible) transparent substrate such as plastics, also possesses low-voltage (10V or less) driving, power consumption is low,
The advantages such as color sensation protrusion.
Organic Light Emitting Diode is formed in thereon, is included the 1st electrode (anode) and above-mentioned 1st electrode isolation, is mutually seen
The 2nd electrode, the organic luminous layer between above-mentioned 1st electrode and above-mentioned 2nd electrode.It is above-mentioned organic for improving luminous efficiency
Luminescent layer includes the hole injection layer (hole injection layerHIL) of sequentially lamination on above-mentioned 1st electrode, hole transport
Layer (hole transporting layer, HTL), luminescent substance layer (emitting material layer, EML), electronics
Transport layer (electron transporting layer, ETL), electron injecting layer (electron injection
Layer, EIL).
From the 1st electrode hole of anode from hole injection layer, hole transmission layer is mobile to luminescent substance layer, from the 2nd electricity of cathode
Pole, for electronics from electron injecting layer, electron transfer layer is moved to luminescent substance layer.
The above-mentioned hole for being moved to luminescent substance layer and electronics form exciton (exciton) after combining, and can become unstable
The energy of state returns the energy of stable state to shine.
The external quantum efficiency (η ext) for the luminescent substance that luminescent substance layer is used can be obtained by following formula, η ext=η
Int × r × Φ × η out-coupling(η int: internal quantum, r: the factor of charge balance, Φ: the quantum effect of radiation
Rate, η out-coupling: coupling efficiency)
The factor (r) of charge balance refers to form the balance in the hole of exciton and electronics, commonly assumes that 100% 1:1 matches to obtain
Must be worth ' 1', the quantum efficiency (Φ) of radiation is the luminous efficiency for being related to practical luminescent substance, is depended in body-dopant system
The fluorescence quantum efficiency of main body.
Internal quantum (η int) refers to the exciton to be formed with the ratio of the modality conversion of light, in the case where fluorescent material
There is the limits value of maximum 0.25.When hole and electronics form exciton after combining, according to the single item exciton of the arrangement of spin
(singlet excition) and triple excitons (triplet exciton) are formed with the ratio of 1:3.But in fluorescent material
Single item exciton participates in luminous, remaining 75% triple exciton is not involved in luminous.
Coupling efficiency (η out-coupling) refers to the ratio for the light being output to the outside among luminous light.Usually heat is steamed
In the case where the molecule formation film for plating isotropism form, each light emitting molecule does not possess certain directionality, with no order
The state of sequence exists.Coupling efficiency under this ordered state out of order is generally assumed to be 0.2.
Therewith, using the maximum luminous efficiency of the Organic Light Emitting Diode original part of fluorescent material about 5 or less.In order to overcome
The low efficiency problem of fluorescent material is developed in addition to single item exciton and triple excitons are all converted to the phosphorescence object of the principle of light
Matter.The high phosphorus of luminous efficiency is had developed in the case where red and green, but is set out for red is also untapped
Light efficiency height and reliable phosphor material, so needing to develop increase quantum efficiency in reliable fluorescent material to improve hair
The substance of light rate.
Summary of the invention
The purpose of the present invention is to provide a kind of delayed fluorescence material and preparation method thereof and organic luminescent device, the present invention
The delayed fluorescence material of offer has preferable performance in terms of luminous efficiency.
It is the electron-donating group (chemical formula by dibenzo indole carbazole the present invention provides a kind of delayed fluorescence compound
1) pyridine (pyridine), diphenylpyrimidin (diphenylpyrimidine) or diphenyl triazine (diphenyl, are connected
Triazine electron-withdrawing group (chemical formula 2)) connects substituted or non-substituted benzene or naphthalene nucleus (chemical formula 3) and combines composition,
[chemical formula 1] [chemical formula 2] [chemical formula 3]
Wherein, in chemical formula 1, it be 3, X be chemical formula is 2 that L, which is chemical formula,K, I, M for connecting key, in chemical formula 2
It is independent to be selected from carbon or nitrogen to be identical or different；R be one or more, hydrogen or C1To C10Alkyl.
Preferably, the K in chemical formula 2, I, M at least two are nitrogen, and R is selected from hydrogen or methyl in chemical formula 3.
Preferably, the particular compound that there is the delayed fluorescence compound any one chemical formula of formula 1 ~ 9 to indicate:
。
The present invention provides a kind of preparation methods of delayed fluorescence material, comprising the following steps:
1) compound of any structure shown in the compound of structure shown in chemical formula (I) and formula (II) is reacted, obtains formula
(III) compound of structure shown in；
Formula (I)；Formula (II)；
Formula (III)；
2) compound of any structure shown in the compound of any structure shown in formula (III) or formula (IV) and formula (V) is carried out anti-
It answers, obtains delayed fluorescence compound as described in claim 1；
Formula (III) or
Formula (IV)；
Formula (V)；
Wherein, in formula (V) C be Br or Cl, K, I, M be it is identical or different, be selected from carbon or nitrogen；R in formula (II), (III) or (IV)
For one or more, it is selected from hydrogen or C1To C10Alkyl.
The present invention does not have special limitation to the source of formula (I) and formula (II) compound, can be bought and be obtained by market, can also
It is prepared according to method well known to those skilled in the art.
The preparation process of delayed fluorescence compound provided by the invention is simple, and has in luminous efficiency and in terms of the service life
Preferable performance.
The present invention provides a kind of organic luminescent devices, including anode, cathode and setting are between the anode and cathode
Organic compound layer, wherein the organic compound layer includes delayed fluorescence compound described in above-mentioned technical proposal.At this
In invention, the delayed fluorescence compound is consistent with delayed fluorescence compound described in above-mentioned technical proposal, and details are not described herein.
In the present invention, the organic luminescent device preferably includes cathode, anode and be arranged between the cathode and anode one
Or multiple compound layers, the compound layer include delayed fluorescence compound described in above-mentioned technical proposal.In the present invention, institute
Stating compound layer can be made of delayed fluorescence compound completely, can also be by the mixing of delayed fluorescence compound and other substances
Object composition.In the present invention, the compound layer include hole injection layer, hole transmission layer, both had hole injection but also with
The technical ability layer of hole transport, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer, both has electricity at electronic barrier layer
Technical ability layer one or more of of the son transmission but also with electron injection.In the present invention, the hole injection layer, hole transport
Layer had both had hole injection but also with hole injecting material, the hole transport that can use routine in the technical ability layer of hole transport
Substance had both had hole injection but also with the substance of hole transport technical ability, can also use the substance of electron-transporting material production.
In the present invention, the compound layer preferably includes luminescent layer, and the luminescent layer includes described in above-mentioned technical proposal
Delayed fluorescence compound.In the present invention, the luminescent layer includes that phosphorescence host, fluorescent host, phosphorescence doping and fluorescence are mixed
It is one or more of miscellaneous.In the present invention, it can also be used as using the delayed fluorescence compound as fluorescent host
Fluorescence doping, and adulterated simultaneously as fluorescent host and fluorescence.In the present invention, the luminescent layer can be red, yellow
Or cyan luminescent layer.In the present invention, when the luminescent layer is cyan luminescent layer, using above-mentioned delayed fluorescence compound as green
Color main body or cyan doping, can be obtained high efficiency, high-resolution, high brightness and the luminescent device of long-life.
In the present invention, the compound layer preferably includes electron transfer layer, and the electron transfer layer includes above-mentioned technology
Delayed fluorescence compound described in scheme.In the present invention, it is also preferable to include metallic compounds for the electron transfer layer.
In the present invention, the compound layer preferably includes luminescent layer and electron transfer layer, and the luminescent layer and electronics pass
Delayed fluorescence of the defeated layer containing delayed fluorescence compound described in above-mentioned technical proposal, in the luminescent layer and electron transfer layer
Compound can be the same or different.
The present invention does not have special limitation to the preparation method of the organic luminescent device, ripe using those skilled in the art
The preparation method for the luminescent device known is prepared.In the present invention, film vapor deposition, electron beam evaporation, object be can use
The methods of physical vapor deposition evaporation metal, conductive oxide and their alloy on substrate form anode；Yin
The preparation method of pole is consistent with anode preparation method；Hole injection layer, hole are deposited in order in the cathode surface being prepared
Transport layer, luminescent layer, air barrier and electron transfer layer.In the present invention, hole injection layer, hole transmission layer, hair are prepared
High molecular material solvent engineering can be used during the multilayered structures such as photosphere, hole blocking layer and electron transfer layer replaces rotation to apply
Film (spin-coating), strip form (tape-casting), scraping blade method (doctor-blading), silk-screen printing
(Screen-Printing), the evaporation coating methods such as ink jet printing or thermal imaging (Thermal-Imaging) reduce the preparation of the number of plies.
The delayed fluorescence compound is prepared organic luminescent device provided by the invention by adopting the above technical scheme.
This organic luminescent device has preferable luminescent properties, can front shine, back side illuminated or lighting at two sides.
In the present invention, the organic luminescent device be preferred for organic photovoltaic cell (OSC), e-book (e-Paper),
Organophotoreceptor (OPC) or polycrystalline organic thin film.
Raw materials used following embodiment of the present invention is commercial goods.
Embodiment
The synthesis of compound 1
Under condition of nitrogen gas, by 7H- dibenzo [c, g] carbazole (12.8g, 47.8mmol), the iodo- 2- nitrobenzene of the bromo- 1- of 4-
(17.2g, 52.6mmol), cesium carbonate (13.8g, 71.7mmol) stir in solvent dimethyl sulfoxide, are stirred at room temperature about 2 hours
Afterwards, temperature is increased to 60 DEG C, is stirred 8 hours, is extracted three times using methylene chloride and deionized water, it is anhydrous after rotary evaporation
MgSO4It is dry, with methylene chloride/methanol recrystallization compound, obtain intermediate 1-1(19g, 85%).Mass spectrum: theoretical value is
466.03 measured value 466.
Under condition of nitrogen gas, by compound 1-1(19.8g, 42.4mmol), SnCl2·2H2O(26.4g, 127.1mmol), second
Alcohol (300ml) stirs 8 hours under the conditions of 70 DEG C, after reaction, is added 1N sodium hydroxide solution (500ml), dichloro is added
Methane, extraction are extracted the organic layer of solution layer, are washed with deionized, anhydrous MgSO4It is dry, intermediate 1-2(13.4g is obtained,
72%).Mass spectrum: theoretical value 436.06, measured value 436.
Under the conditions of ice-water bath, intermediate 1-2 (14.6g, 33.28mmol) is dissolved into acetic acid (250ml), thiosulfonic acid
(100ml) stirring, the sodium nitrite (2.53g, 36.62mmol) of 1.1 equivalents are dissolved in (100ml) deionized water, intermediate
1-2 is first stirred 15 minutes, stirring again slowly after ten minutes, and 130 DEG C are reacted 20 minutes, after reaction, is reduced to room temperature, is added
Enter deionized water (350ml), sediment occur, sediment is filtered, methanol (500ml) rinses, and recrystallization obtains intermediate 1-
3(10.8g, 77%).Mass spectrum: theoretical value 419.03, measured value 419.
Under condition of nitrogen gas, by intermediate 1-3(17.4g, 41.4mmol), two boron of duplex pinacol base of 1.2 equivalents
(12.6g, 49.69mmol), 1,1 '-bis- (diphenylphosphino) ferrocene palladiums (II) (0.1g), potassium acetate (20g), Isosorbide-5-Nitrae-two
Six ring of oxygen: it after toluene (1:1) (350ml) stirring, after bubble collapse, is stirred to react at 120 DEG C 17 hours.After reaction, it uses
Methylene chloride washing.The intermediate 1-5(14.9g being refining to obtain, 77%).Mass spectrum: theoretical value 467.21, measured value 467.
Under condition of nitrogen gas, intermediate 1-4(14.8g, 31.76mmol) is dissolved into toluene (350ml), it is bromo- that 1- is added
4- iodobenzene (8.1g, 28.58mmol), the calcium carbonate (K of deionized water dissolving2CO3) (19.7g, 142.74mmol), tetrahydrofuran
(200ml), tetra-triphenylphosphine palladium (0.1g) stir in 80 DEG C of reaction mixture refluxeds.Use methylene chloride/n-hexane, extraction
After taking, then recrystallizing, column chromatographs to obtain intermediate 1-5(10.4g, and 66%).Mass spectrum: theoretical value 495.06, measured value 495.
Under condition of nitrogen gas, the intermediate 1-5(22.2g, 44.82mmol of 1.2 equivalents under the conditions of -78 DEG C of temperature) tetrahydrofuran
After (400ml) dissolution, dropwise addition n- butyl lithium (2.9g, 44.82mmol) slowly continuously adds chloro- 4, the 6- diphenyl -1,3 of 2-,
5- triazine (10g, 37.35mmol), tetrahydrofuran (150ml) are stirred to react 8 hours.After reaction, compound 1 is post-processed
(15.4g, 70%).Mass spectrum: theoretical value 648.23, measured value 648.
The synthesis of compound 2
Under condition of nitrogen gas, intermediate 1-5 (20.6g, 41.4mmol), 1.2 equivalents two boron of duplex pinacol base (12.6g,
49.69mmol), 1,1 '-bis- (diphenylphosphino) ferrocene palladiums (II) (0.1g), potassium acetate (20g), Isosorbide-5-Nitrae-dioxane:
Toluene (1:1) (350ml) stirs, and after bubble collapse, is stirred to react at 120 DEG C 17 hours.After reaction, it is washed with methylene chloride
It washs.The intermediate 2-1 (17.3g, 77%) being refining to obtain.Mass spectrum: theoretical value 543.24, measured value 543.
Under nitrogen environment, by 4- bromopyridine (4.5g, 28.58mmol), toluene (150 ml), intermediate 2-1(17.3g,
31.76mmol), calcium carbonate (K2CO3) after (19.7g, 142.74mmol) deionized water dissolving, four are added in the reactive mixture
Hydrogen furans (200ml), tetra-triphenylphosphine palladium (0.1g), in 80 DEG C of back flow reactions, stirring uses methylene chloride/n-hexane extraction
Afterwards, it then recrystallizes, obtains compound 2(8.9g, 63%).Mass spectrum: theoretical value 494.18, measured value 494.
The synthesis of compound 3
By 2- bromopyridine (4.5g, 28.58mmol), intermediate 2-1 (17.3g, 31.76mmol), potassium carbonate (K2CO3)
(19.7g, 142.74mmol), tetra-triphenylphosphine palladium (0.1g) use experimental method identical with compound 2, has obtained compound
3(11.2g,79%).Mass spectrum: theoretical value 494.18, measured value 494.
The synthesis of compound 4
By the chloro- 4,6- diphenylpyrimidin (7.6g, 28.58mmol) of 2-, intermediate 2-1 (17.2g, 31.76mmol), potassium carbonate
(K2CO3) (19.7g, 142.74mmol), tetra-triphenylphosphine palladium (0.1g) use experimental method identical with compound 2 obtains
Compound 4 (13.5g, 73%).Mass spectrum: theoretical value 647.24, measured value 647.
The synthesis of compound 5
By the iodo- 2- methylbenzene (8.5g, 28.58mmol) of the bromo- 1- of 4-, intermediate 1-5 (14.8g, 31.76mmol), potassium carbonate
(K2CO3) (19.7g, 142.74mmol), tetra-triphenylphosphine palladium (0.1g) use experimental method identical with compound 2, obtains
Intermediate 5-1 (12.1g, 83%) is arrived.Mass spectrum: theoretical value 509.08, measured value 509.
By intermediate 5-1 (22.9g, 44.82mmol), n- butyl lithium (2.9g, 44.82mmol), the chloro- 4,6- hexichol of 2-
Base -1,3,5-triazines (10g, 37.35mmol) use experimental method identical with compound 1, obtained compound 5 (23.5g,
79%).Mass spectrum: theoretical value 662.25, measured value 662.
The synthesis of compound 6
The iodo- 2,5- dimethyl benzene (10g, 32.2mmol) of the bromo- 4- of 1-, intermediate 1-5 (18g, 38.6mmol), potassium carbonate
(K2CO3) (19.7g, 142.74mmol), tetra-triphenylphosphine palladium (0.1g) use experimental method identical with compound 2 obtains
Intermediate 6-1 (14.4g, 85%) mass spectrum theoretical value is 523.09, measured value 523.
By intermediate 6-1 (23.5g, 44.82mmol), n- butyl lithium (2.9g, 44.82mmol), the chloro- 4,6- hexichol of 2-
Base -1,3,5-triazines (10g, 37.35mmol) use experimental method identical with compound 1, obtained compound 6 (18.5g,
79%).Mass spectrum: theoretical value 523.09, measured value 523.
The synthesis of compound 7
Intermediate 5-1 (21.1g, 41.4mmol), two boron (12.6g, 49.69mmol) of duplex pinacol base of 1.2 equivalents, 1,
1 '-bis- (diphenylphosphino) ferrocene palladiums (II) (0.1g), potassium acetate (20g) use the identical experimental method of intermediate 2-1
Intermediate 7-1 (14.9g, 72%) is obtained.Mass spectrum: theoretical value 557.25, measured value 557.
By 4- bromopyridine (4.5g, 28.58mmol), intermediate 7-1 (17.7g, 31.76mmol), potassium carbonate (K2CO3)
(19.7g, 142.74mmol), tetra-triphenylphosphine palladium (0.1g) use experimental method identical with compound 2, has obtained chemical combination
Object 7 (10g, 69%).Mass spectrum: theoretical value 508.19, measured value 508.
The synthesis of compound 8
The chloro- 4,6- diphenylpyrimidin (7.6g, 28.58mmol) of 2-, intermediate 7-1 (17.7g, 31.76mmol), potassium carbonate
(K2CO3) (19.7g, 142.74mmol), tetra-triphenylphosphine palladium (0.1g) obtained using experimental method identical with compound 2
Compound 8 (16.3g, 86%).Mass spectrum: theoretical value 661.25, measured value 661.
The synthesis of compound 9
The bromo- 5- iodobenzene (10.7g, 32.2mmol) of intermediate 1-4 (18g, 38.6mmol), 1-, potassium carbonate (K2CO3)(19.7g,
142.74mmol), tetra-triphenylphosphine palladium (0.1g), with the identical experimental method of intermediate 1-5 obtain intermediate 9-1 (15g,
85%), mass spectrum: theoretical value 545.08, measured value 545.
Intermediate 9-1 (25.2g, 44.82mmol), n- butyl lithium (2.9g, 44.82mmol), chloro- 4, the 6- diphenyl-of 2-
1,3,5-triazines (10g, 37.35mmol) obtains compound 9 (24.1g, 77%) with the identical experimental method of compound 1.Mass spectrum:
Theoretical value is 698.25, measured value 698.
The preparation of device
The ito substrate that area is 3mm × 3mm is cleaned, then, aforesaid substrate is transmitted to vacuum film coating chamber.Base pressure is
10-6~10-7, ITO is that i) hole injection layer 40 are successively deposited in substrate, (NPB (bis- (1- the naphthalene)-N of N, N'-, N'- diphenyl
Benzidine)), ii) hole transmission layer 10 (mCP (bis- carbazyl -3,5- benzene of N, N'-)), iii) (the main body material of luminescent layer 200
Expect (compound and comparative example in bis- { 2 [two (phenyl) phosphino-s] phenyl } ether/dopant material (15%) tables 1), iv) electron transport
Layer 300 (1,3,5- tri- (2-Phenylbenzimidazole)-benzene), v) electron injecting layer 10 (LiF), vi) cathode (Al).
(1) comparative example (Ref)
Organic luminescent device is prepared according to the method described above, and dopant material, which is substituted for structural formula, is
Compound.
(2) compound 1 ~ 10 is prepared into organic luminescent device according to the method described above, with scanning optical spectrum luminance meter
PhotoResearchPR670, Keithley238 measuring device, quantum efficiency test system have rated compound 1 ~ 10 and compare
Efficiency, service life and the color of the organic luminescent device of example compound preparation, and result is shown in the following table 1.
The performance test results for the organic luminescent device that 1 embodiment of table and comparative example are prepared
From above-mentioned 1 result of table, it is seen that the compound of the present invention quantum efficiency and luminous efficiency increase significantly, so this
Invention is useful in the high OLED industry of practicability.Organic luminescent device of the invention is that flat panel shows, is flat luminous
Body, illumination face illuminating OLED illuminator, flexible illuminator, duplicator, printer, LCD backlight lamp or dosing machine class light source,
The suitable use such as display board, mark.
Claims (6)
1. a kind of delayed fluorescence compound is the electron-donating group (chemical formula 1) by dibenzo indole carbazole, pyridine is connected
(pyridine), the suction of diphenylpyrimidin (diphenylpyrimidine) or diphenyl triazine (diphenyl triazine)
Electron group (chemical formula 2) connects substituted or non-substituted benzene or naphthalene nucleus (chemical formula 3) and combines composition,
[chemical formula 1] [chemical formula 2] [chemical formula 3]
Wherein, in chemical formula 1, it be 3, X be chemical formula is 2 that L, which is chemical formula,K, I, M for connecting key, in chemical formula 2
It is independent to be selected from carbon or nitrogen to be identical or different；R be one or more, hydrogen or C1To C10Alkyl.
2. delayed fluorescence compound according to claim 1, which is characterized in that the K in chemical formula 2, I, M at least two are
Nitrogen, R is selected from hydrogen or methyl in chemical formula 3.
3. delayed fluorescence compound according to claim 1, which is characterized in that the delayed fluorescence compound have formula 1 ~
The particular compound that 9 any one chemical formula indicate:
。
4. the present invention provides a kind of preparation methods of delayed fluorescence material, comprising the following steps: by formula (III) or formula (IV) institute
Show that the compound of any structure is reacted with the compound of any structure shown in formula (V), is prolonged as described in claim 1
Slow fluorescent chemicals；
Formula (III) or
Formula (IV)；
Formula (V)；
Wherein, in formula (V) C be Br or Cl, K, I, M be it is identical or different, be selected from carbon or nitrogen；R is 1 in formula (III) or (IV)
Or multiple, hydrogen or C1To C10Alkyl.
5. the preparation method of delayed fluorescence material according to claim 4, which is characterized in that structure shown in formula (III)
Compound be the structure as shown in chemical formula (I) compound and formula (II) shown in the compound of any structure reacted to obtain
's；
Formula (I)；Formula (II)；
Formula (III)；
Wherein, in formula (V) C be Br or Cl, K, I, M be it is identical or different, be selected from carbon or nitrogen；R in formula (II), (III) or (IV)
For one or more, hydrogen or C1To C10Alkyl.
6. a kind of organic luminescent device, including anode, cathode and the organic compound layer being arranged between the anode and cathode,
It is characterized in that, the organic luminous layer includes compound containing delayed fluorescence described in any one of claim 1 ~ 3.
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| TWI783361B (en) * | 2021-01-29 | 2022-11-11 | 機光科技股份有限公司 | Organic compound and application in blue organic electroluminescent device thereof |
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| KR20110066763A (en) * | 2009-12-11 | 2011-06-17 | 덕산하이메탈(주) | Compound containing indoloacridine and organic electronic element using the same, terminal thereof |
| WO2017014460A1 (en) * | 2015-07-17 | 2017-01-26 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110066763A (en) * | 2009-12-11 | 2011-06-17 | 덕산하이메탈(주) | Compound containing indoloacridine and organic electronic element using the same, terminal thereof |
| WO2017014460A1 (en) * | 2015-07-17 | 2017-01-26 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same, and electronic device thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI783361B (en) * | 2021-01-29 | 2022-11-11 | 機光科技股份有限公司 | Organic compound and application in blue organic electroluminescent device thereof |
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