CN106883204A - Organic electroluminescent compounds and luminescent device based on benzo [b] naphtho- [1,2 d] furans - Google Patents
Organic electroluminescent compounds and luminescent device based on benzo [b] naphtho- [1,2 d] furans Download PDFInfo
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- JUSLFCDMBJNHNU-UHFFFAOYSA-N CB(c1cc2ccccc2c2c1[o]c1ccccc21)O Chemical compound CB(c1cc2ccccc2c2c1[o]c1ccccc21)O JUSLFCDMBJNHNU-UHFFFAOYSA-N 0.000 description 1
- LORFSVGEIMOTGG-VWBGMLFYSA-N CC/C=C(\C=C/C)/NC(CC=C1)c2c1c(cccc1)c1[o]2 Chemical compound CC/C=C(\C=C/C)/NC(CC=C1)c2c1c(cccc1)c1[o]2 LORFSVGEIMOTGG-VWBGMLFYSA-N 0.000 description 1
- CLQNJNQUKWHSFM-MEFJORIHSA-N C[C@H](C1(C)C=Cc2c3[o]c4c2cccc4)[C@@]13N(c(cc1)ccc1-c1cc2ccccc2c2c1[o]c1ccccc21)c1ccccc1 Chemical compound C[C@H](C1(C)C=Cc2c3[o]c4c2cccc4)[C@@]13N(c(cc1)ccc1-c1cc2ccccc2c2c1[o]c1ccccc21)c1ccccc1 CLQNJNQUKWHSFM-MEFJORIHSA-N 0.000 description 1
- AKBFJTFQTRGKQJ-UHFFFAOYSA-N OB(c1cc(cccc2)c2c2c1OC1=CCCC=C21)O Chemical compound OB(c1cc(cccc2)c2c2c1OC1=CCCC=C21)O AKBFJTFQTRGKQJ-UHFFFAOYSA-N 0.000 description 1
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Abstract
Benzo [b] naphtho- [1 is based on the invention provides one kind, 2 d] furans organic electroluminescent compounds, the compound has preferable heat endurance, high-luminous-efficiency, luminance purity high, can be used for making organic electroluminescence device, be applied to organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, organic layer includes at least one of which in luminescent layer, hole injection layer, hole transmission layer, exciton barrier-layer, electron transfer layer, and at least one of which includes the compound just like structural formula I in organic layer.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to one kind is based on benzo [b] naphtho- [1,2-d] furans
Organic electroluminescent compounds and its organic electroluminescence device, belong to organic electroluminescence device display technology field.
Background technology
Organic electroluminescence device (OLEDs) is to deposit one by spin coating or vacuum evaporation between two metal electrodes
The device that layer organic material is prepared from, the three of classics layers of organic electroluminescence device include hole transmission layer, luminescent layer
And electron transfer layer.The hole produced by anode through hole transmission layer with the electronics that is produced by negative electrode through combined with electron transfer layer
Luminescent layer forms exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer
The light of the various needs of section transmitting.
Organic electroluminescence device as a kind of new Display Technique, with self-luminous, wide viewing angle, low energy consumption, efficiency
High, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent
Display panel and the particular advantages such as environment-friendly, can apply on flat-panel monitor and a new generation's illumination, it is also possible to as
The backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device has industrially been applied, such as
Used as screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts it
General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just
It is the performance of the electroluminescent organic material in organic electroluminescence device.Run in applied voltage additionally, due to OLED
When, Joule heat can be produced so that organic material is susceptible to crystallization, have impact on life-span and the efficiency of device, therefore, it is also desirable 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 be effectively reduced positive electricity
Lotus is transferred to the ability of luminescent layer from positive pole, improves the efficiency of device and thermally-stabilised.Traditional hole-injecting material, such as copper
Phthalocyanine (CuPc), degraded is slow, prepares power consumption height, is unfavorable for environmental protection, and it can absorb light, influence device
Efficiency.NPB etc. original hole mobile material, heat endurance is poor, also largely influences device lifetime.Thus, need
Develop the electroluminescent organic material of efficient stable.
The content of the invention
Present invention firstly provides organic electroluminescent compounds of the one kind based on benzo [b] naphtho- [1,2-d] furans, it is
Compound with following structural formula I：
Wherein, Ar1-Ar3Separately selected from substitution or unsubstituted C6-C30 aryl, substitution or unsubstituted
C3-C30 heteroaryls, triaromatic amine base, carbazyl；
L1And L2Separately selected from singly-bound, substitution or unsubstituted C6-C30 aryl.
Preferably, Ar1Selected from phenyl, naphthyl, xenyl, (9,9- dialkyl group) fluorenyl, (substitutions of 9,9- bis- are unsubstituted
Aryl) fluorenyl, Ar2And Ar3Separately it is selected from phenyl, naphthyl, xenyl, phenyl napthyl, naphthylphenyl, N- aryl
(C6-C30) or C1-C4 alkyl-substituted carbazyl, anthryl, phenanthryl, pyrenyl, perylenes base, fluoranthene base, (9,9- dialkyl group) fluorenes
Base, (substitutions of 9,9- bis- or unsubstituted aryl) fluorenyl, 9,9- are Spirofluorene-based, three fragrant (C6-C60) amidos, dibenzothiophenes
Base, dibenzofuran group, above aryl further can be replaced by the alkyl of C1-C12.
Preferably, L1And L2Separately it is selected from singly-bound, phenyl, naphthyl, xenyl.
It is further preferred that compound of the organic electroluminescent compounds of the invention for following structural 1-38：
Organic electroluminescent compounds based on benzo [b] naphtho- [1,2-d] furans of the invention can pass through
Buchwald-Hartwig is reacted and ullmann reaction is prepared.
Organic electroluminescent compounds based on benzo [b] naphtho- [1,2-d] furans of the invention can be applied organic
Electroluminescent device, organic solar batteries, perovskite battery, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer
Comprising at least one of which in luminescent layer, hole injection layer, hole transmission layer, exciton barrier-layer, electron transfer layer, wherein described have
At least one layer contains the compound based on benzo [b] naphtho- [1,2-d] furans as described in structural formula I in machine layer：
Wherein Ar1、Ar2、Ar3、L1And L2It is defined as described above.
Wherein organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton
Barrier layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and exciton barrier-layer.
Preferably, wherein the layer where compound as described in structural formula I is hole transmission layer.
Preferably, the hole transport compound wherein described in structural formula I is the compound of structural formula 1-38.
When the compound based on benzo [b] naphtho- [1,2-d] furans as described in structural formula I is prepared for luminescent device,
Can be used alone, it is also possible to and other compounds are used in mixed way；As described in structural formula I based on benzo [b] naphtho- [1,2-d]
The electroluminescent compounds of furans can be used alone a kind of compound therein, it is also possible to while using two in structural formula I
Plant the compound of the above.
Organic electroluminescence device of the invention, further preferred mode is that the organic electroluminescence device includes sun
Pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, contain at least one in its hole-transporting layer
The compound of structural formula I；It is further preferred that the compound containing at least one structural formula 1-38 in hole transmission layer.
The gross thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes organic electroluminescence device of the invention
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer
It is medium, and obtain blue and green light, gold-tinted, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole
Transmission performance, can effectively be transferred to hole on luminescent layer from anode.Except above-mentioned with compound described in structural formula I
Outward, other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine can also be included
Compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano group six
(hexanitrilehexaazatriphenylene), the cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'- tetra-
TCNQ), PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention, with the good characteristics of luminescence, can be adjusted as needed
The scope of visible ray.Except it is of the invention with Compounds of structural formula I in addition to, can also contain following compound, including but do not limit
In naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound, class compound in the wrong, glimmering anthracene compound, anthracene class
Compound, pentacene class compound, perylene classes compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, amine chemical combination
Thing, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal Phosphorescent
Complex compound (such as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-organosilicon compound, polythiophene organic polymer luminescent material, it
Can be used alone, it is also possible to various mixtures are used.The thickness of luminescent layer is preferably 10-50nm.
The Organic Electron Transport Material requirement of organic electroluminescence device of the present invention has good electronic transmission performance, energy
It is enough effectively electronics from cathode transport to luminescent layer in, with very big electron mobility.Following compound can be selected, but
It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination
Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound,
Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from negative electrode
In, the compound of alkali metal or alkali metal is mainly selected from, or selected from alkaline-earth metal or the compound or alkali of alkaline-earth metal
Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal
Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid
Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make
With can also mixture use, it is also possible to used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in organic electroluminescence device of the invention, can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Can make for metal motor
It is prepared with vapour deposition method or sputtering method.
Device experimental shows, compound based on benzo [b] naphtho- [1,2-d] furans of the present invention as described in structural formula I
With preferable heat endurance, high-luminous-efficiency, luminance purity high, low driving voltage.Made using the hole transport compound
Organic electroluminescence device has the advantages that electroluminescent efficiency is good and excitation is excellent and long lifespan.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural representation of the invention；
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as hair
Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Specific embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthesis of compound 4
The synthesis of intermediate 4-1
In there-necked flask, add N- (dibenzofurans -4- bases)-aniline (2.6g, 10mmol), to bromo-iodobenzene (2.8g,
10mmol), potassium carbonate (2.7g, 20mmol), cuprous iodide (0.3g), Phen (0.3g) and ortho-xylene (30mL),
It is heated to reflux 10 hours under nitrogen protection, is cooled down, remove solvent, crude by column chromatography purifying obtains product 3.4g, yield
83%.
The synthesis of compound 4
In there-necked flask, intermediate 4-1 (0.5g, 1.2mmol), benzo [b] naphtho- [1,2-d] furans -6- boron are added
Sour (0.32g, 1.2mmol), potassium carbonate (0.33g, 2.4mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (15mL) and water
(5mL), is heated to reflux 10 hours under nitrogen protection, cools down, and is extracted with dichloromethane, dries, and concentration, crude product is pure through column chromatography
Change obtains 0.56g, yield 85%.MS:551.45.
Embodiment 2
The synthesis of compound 5
The synthesis of intermediate 5-1
Synthetic method with as intermediate 4-1, except replacing N- (dibenzo with N- (9- phenyl carbazole -3- bases)-aniline
Furans -4- bases) outside-aniline, yield 68%.
The synthesis of compound 5
Synthetic method as the synthesis of compound 4, in addition to replacing intermediate 4-1 with intermediate 5-1, yield 76%.
MS:626.31。
Embodiment 3
The synthesis of compound 10
The synthesis of intermediate 10-1
The synthesis of intermediate 10-1 with as intermediate 4-1, except with N- (9,9- dimethyl -9H- fluorenes -2- bases) -1-
Naphthylamines replaces outside N- (dibenzofurans -4- bases)-aniline, yield 73%.
The synthesis of compound 10
Synthetic method as compound 4, in addition to replacing intermediate 4-1 with intermediate 10-1, yield 83%.MS:
627.73。
Embodiment 4
The synthesis of compound 19
The synthesis of intermediate 19-1
Synthetic method as the synthetic method of intermediate 4-1, except with intermediate N (9,9- dimethyl -9H- fluorenyls -
2- yls) -4- xenylamines replace N- (dibenzofurans -4- bases)-aniline outside, yield 90%.
The synthesis of compound 19
Synthetic method as compound 4, in addition to replacing intermediate 4-1 with intermediate 19-1, yield 89%.MS:
653.85。
Embodiment 5
The synthesis of compound 24
The synthesis of intermediate 24-1
In flask, N- (4- xenyls)-aniline (2g, 8.2mmol), DMF (20mL) are added, be slowly added to bromo fourth two
Acid imide (1.5g, 8.6mmol), ambient temperature overnight reaction, is added to the water, and filters, and filter cake is beaten with ethanol, dries, and obtains product
2.4g, yield 90%.
The synthesis of intermediate 24-2
In flask, add intermediate 24-1 (2g, 6.2mmol), 9- phenyl -3- carbazoles boric acid (1.95g, 6.9mmol),
Potassium carbonate (1.7g, 12.4mmol), tetrahydrofuran (20mL), water (10mL) and four triphenyl phosphorus palladiums (0.3g), in nitrogen protection
Under be heated to reflux 10 hours, cool down, extracted with dichloromethane, dry, concentration, crude product tetrahydrofuran and ethyl alcohol recrystallization,
Obtain product 2.6g, yield 86%.
The synthesis of intermediate 24-3
Synthetic method as intermediate 4-1, except replacing N- (dibenzofurans -4- bases)-aniline with intermediate 24-2
Outward, yield 65%.
The synthesis of compound 24
Synthetic method with as compound 4, in addition to replacing intermediate 4-1 with intermediate 24-3, yield 73%.MS:
778.40。
Embodiment 6
The synthesis of compound 25
The synthesis of intermediate 25-1
Synthetic method with as intermediate 24-2, except replacing 9- phenyl -3- carbazole boron with 4- dibenzofurans boric acid
It is sour outer, yield 75%.
The synthesis of intermediate 24-2
Synthetic method as the synthetic method of intermediate 4-1, except replaced with intermediate 25-1 N- (dibenzofurans-
4- yls) outside-aniline, yield 56%.
The synthesis of compound 25
Synthetic method as compound 4, in addition to replacing intermediate 4-1 with intermediate 24-2, yield 86%.MS:
703.26。
Embodiment 7
The synthesis of compound 28
The synthesis of intermediate 28-1
In there-necked flask, 4- bromines dibenzofurans (2.4g, 10mmol), 2- amino -9,9- dimethyl fluorenes are added
(2.1g, 10mmol), sodium tert-butoxide (2g, 20mmol), palladium (0.2g), X-phos (0.3g), toluene (30mL), in nitrogen
It is heated to reflux under protection 12 hours, is cooled down, remove solvent, crude product obtains 2.6g, yield 69% through column chromatography purifying.
The synthesis of intermediate 28-2
Synthetic method with as intermediate 4-1, except replacing N- (dibenzofurans -4- bases)-benzene with intermediate 28-1
Outside amine, yield 68%.
The synthesis of compound 28
Synthetic method with as compound, in addition to replacing intermediate 4-1 with intermediate 28-2, yield 76%.MS:
667.77。
Embodiment 8
The synthesis of compound 35
The synthesis of intermediate 35-1
With as intermediate 28-1, raw materials used be N- (base of 9,9- dimethyl fluorene -2)-aniline and 2,7- to synthetic method
Two bromo- 9,9- dimethyl fluorenes, yield 47%.
The synthesis of compound 35
Synthetic method with as compound 4, in addition to replacing intermediate 4-1 with intermediate 35-1, yield 68%.MS:
693.30
Embodiment 9-16
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment of the present invention 1-8 and comparative example.
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (the South China glass group limited public affairs of share
Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, this compound (such as following table) is deposited with, the thick hole transmission layers 130 of 60nm are formed.
Then, the thick compound Alq of 30nm are deposited with hole transmission layer3As luminescent layer 140.
Then, the thick Alq of 20nm are deposited with luminescent layer3As electron transfer layer 150.Finally, evaporation 1nm LiF are electricity
Sub- implanted layer 160 and 100nm Al are used as device cathodes 170.
Prepared device (structure such as Fig. 1) is measured in 150mA/cm with Photo Research PR650 spectrometers2's
Device efficiency such as following table under current density.
| Embodiment | Compound | Current efficiency (cd/A) | Color |
| 9 | 4 | 1.3 | Green |
| 10 | 5 | 1.7 | Green |
| 11 | 10 | 1.5 | Green |
| 12 | 19 | 1.6 | Green |
| 13 | 24 | 1.8 | Green |
| 14 | 25 | 1.5 | Green |
| 15 | 28 | 1.6 | Green |
| 16 | 35 | 1.4 | Green |
| Comparative example | NPB | 1.2 | Green |
At identical conditions, the organic electroluminescence device for being prepared using organic electroluminescent compounds of the invention
Efficiency is higher than comparative example.As described above, compound of the invention has stability high, organic electroluminescent prepared by the present invention
Device has low driving voltage, efficiency high and optical purity.
Structural formula is as follows described in device：
Preferred embodiment of the invention described in detail above.It should be appreciated that the ordinary skill of this area is without wound
The property made work just can make many modifications and variations with design of the invention.Therefore, all technical staff in the art
Pass through the available technology of logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Scheme, all should be in the protection domain being defined in the patent claims.
Claims (10)
1. one kind is based on the organic electroluminescent compounds of benzo [b] naphtho- [1,2-d] furans, it is characterised in that it is with such as
The compound of lower structural formula I：
Wherein, Ar1-Ar3Separately selected from substitution or unsubstituted C6-C30 aryl, substitution or unsubstituted C3-
C30 heteroaryls, triaromatic amine base, carbazyl；
L1And L2Separately selected from singly-bound, substitution or unsubstituted C6-C30 aryl.
2. organic electroluminescent compounds based on benzo [b] naphtho- [1,2-d] furans according to claim 1, it is special
It is Ar to levy1Selected from phenyl, naphthyl, xenyl, (9,9- dialkyl group) fluorenyl, (substitutions of 9,9- bis- or unsubstituted aryl) fluorenes
Base, Ar2And Ar3Separately selected from the alkyl-substituted of phenyl, naphthyl, xenyl, N- aryl (C6-C30) or C1-C4
Carbazyl, anthryl, phenanthryl, pyrenyl, perylenes base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (substitutions of 9,9- bis- or unsubstituted virtue
Base) fluorenyl, 9,9- be Spirofluorene-based, three fragrant (C6-C60) amidos, dibenzothiophenes base, dibenzofuran group, or more aryl enter
One step is replaced by the alkyl of C1-C12.
3. organic electroluminescent compounds based on benzo [b] naphtho- [1,2-d] furans according to claim 1, it is special
It is L to levy1And L2Separately it is selected from singly-bound, phenyl, naphthyl, xenyl.
4. organic electroluminescent compounds based on benzo [b] naphtho- [1,2-d] furans according to claim 1, it is special
It is compound that it is following structural 1-38 to levy：
5. a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, and organic layer injects comprising luminescent layer, hole
At least one of which in layer, hole transmission layer, exciton barrier-layer, electron transfer layer, it is characterised in that at least one of which bag in organic layer
Contain the compound based on benzo [b] naphtho- [1,2-d] furans as claimed in claim 1.
6. organic electroluminescence device according to claim 5, it is characterised in that as described in structural formula I based on benzo
Layer where the compound of [b] naphtho- [1,2-d] furans is hole transmission layer.
7. organic electroluminescence device according to claim 5, it is characterised in that as described in structural formula I based on benzo
The compound of [b] naphtho- [1,2-d] furans is used alone, or is used in mixed way with other compounds.
8. organic electroluminescence device according to claim 5, it is characterised in that as described in structural formula I based on benzo
The compound of [b] naphtho- [1,2-d] furans is used alone a kind of compound therein, or uses two kinds in structural formula I simultaneously
Compound above.
9. organic electroluminescence device according to claim 5, it includes anode, hole transmission layer, luminescent layer, electronics and passes
Defeated layer, electron injecting layer and negative electrode, it is characterised in that the compound containing at least one structural formula I in hole transmission layer.
10. organic electroluminescence device according to claim 5, it includes anode, hole transmission layer, luminescent layer, electronics
Transport layer, electron injecting layer and negative electrode, it is characterised in that the compound containing at least one structural formula 1-38 in hole transmission layer.
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| CN107935999A (en) * | 2017-11-28 | 2018-04-20 | 上海道亦化工科技有限公司 | A kind of naphtho- benzofuran compound and application thereof and organic electroluminescence device |
| CN110317184A (en) * | 2018-03-29 | 2019-10-11 | 江苏三月光电科技有限公司 | A kind of compound based on double dimethyl fluorenes, preparation method and applications |
| CN111848559A (en) * | 2019-04-25 | 2020-10-30 | 上海钥熠电子科技有限公司 | Organic electroluminescent material and application thereof |
| WO2022045745A1 (en) * | 2020-08-24 | 2022-03-03 | 주식회사 엘지화학 | Organic light-emitting device |
| WO2022045743A1 (en) * | 2020-08-24 | 2022-03-03 | 주식회사 엘지화학 | Novel compound and organic light-emitting device using same |
| WO2022089428A1 (en) * | 2020-10-30 | 2022-05-05 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, and electronic element and electronic device having same |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107935999A (en) * | 2017-11-28 | 2018-04-20 | 上海道亦化工科技有限公司 | A kind of naphtho- benzofuran compound and application thereof and organic electroluminescence device |
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| CN111848559A (en) * | 2019-04-25 | 2020-10-30 | 上海钥熠电子科技有限公司 | Organic electroluminescent material and application thereof |
| WO2022045745A1 (en) * | 2020-08-24 | 2022-03-03 | 주식회사 엘지화학 | Organic light-emitting device |
| WO2022045743A1 (en) * | 2020-08-24 | 2022-03-03 | 주식회사 엘지화학 | Novel compound and organic light-emitting device using same |
| WO2022089428A1 (en) * | 2020-10-30 | 2022-05-05 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, and electronic element and electronic device having same |
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