CN105237501A - Organic light-emitting material containing spirobifluorene and dibenzofuran and organic light-emitting device - Google Patents
Organic light-emitting material containing spirobifluorene and dibenzofuran and organic light-emitting device Download PDFInfo
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- CN105237501A CN105237501A CN201510563757.6A CN201510563757A CN105237501A CN 105237501 A CN105237501 A CN 105237501A CN 201510563757 A CN201510563757 A CN 201510563757A CN 105237501 A CN105237501 A CN 105237501A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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Abstract
The invention discloses the luminous organic material containing spiro-bisfluorene and dibenzofurans and devices of giving out light, the luminous organic material has structure represented by following formula I, wherein R1, R2, R3, R4 group is hydrogen atom or dibenzofurans group, and wherein at least two group is that dibenzofurans group, dibenzofurans group and spiro-bisfluorene group are directly connected to by any site with covalent single bond;
. Luminescent material can be used to prepare efficient electroluminescent device; Luminescent material of the invention realizes very high efficiency of luminescent device in the case where not using carbazole unit. Simultaneously in the present invention in the compound based on dibenzofurans and spiro-bisfluorene, the compound containing two or more dibenzofurans units has better luminescent device performance and efficiency compared with the similar compound for containing only a dibenzofurans unit; It is a kind of efficient device with outstanding representation.
Description
Technical field
The invention belongs to organic photoelectrical material technical field, be specifically related to the luminous organic material containing spiro-bisfluorene and diphenylene-oxide and luminescent device.
Background technology
Since the Deng Qingyun (ChingW.Tang) of Kodak in 1987 is with oxine aluminium (Alq
3) for luminescent layer has made first organic luminescent device with practical value, organic luminescent device and associated materials start to be paid close attention to widely and study.Through the development of nearly 30 years, organic electroluminescence device showed wide application prospect in the field such as flat pannel display and illumination.
The general ultimate principle of organic luminescent device is: under the driving of impressed current, electronics and hole are respectively by negative electrode and the anode injection of device, respectively through different functional layers, meet and are compounded to form exciton in electronics and hole in luminescent layer, excite luminous organic material luminous.The organic luminescent device with practical value is reported in 1987 by the Deng Qingyun of Kodak company.This device adopts ito glass as anode, and aryl diamine is as hole transmission layer, and 8-hydroxyquinoline aluminum is as luminescent layer (electron transfer layer of holding concurrently), and Mg/Ag, as negative electrode, achieves 1000cdm under the low voltage of 5V
-2high brightness, 3cdA
-1current efficiency and 1% external quantum efficiency.1999 by [M.A.Baldo, S.Lamansky, P.E.Burroes such as Forrest and Thompson, M.E.Thompson, S.R.Forrest.Appl.Phys.Lett., 1999,75,4] phosphorescent devices reported is that another has the invention of milestone significance.It has employed heavy metal (Ir, Pt, the Os etc.) title complex with phosphorescence luminescence achieves 100% device internal quantum efficiency as luminescent material.According to quantum-mechanical theory, when hole and electron recombination produce exciton, singlet (singlet) exciton of 25% and triplet state (triplet) exciton of 75% can be produced.Because triplet excited states is spin forbidden to the transition of ground state, traditional organic fluorescence molecule can only utilize the exciton of 25%, and internal quantum efficiency has been limited in 25%.And heavy metal complex can pass through Effect of Spin-orbit Coupling (spin-orbitcoupling) realizes intersystem crossing (intersystemcrossing) thus realize the transition of triplet state to ground state, namely phosphorescence is luminous, makes the internal quantum efficiency of device significantly bring up to 100%.The luminescent layer of phosphorescent devices generally adopts the doped structure of Subjective and Objective, and phosphorescence heavy metal complex is doped in the material of main part of organic molecule formation as light-emitting guest.The exciton that main body produces can be transferred to object, realizes luminous, and avoids the triplet state-triplet state annihilation problem of phosphorescence heavy metal complex, improve efficiency and the stability of device.The maximum innovation of phosphorescent devices is exactly make use of triplet excitons.In recent years, by (HirokiUoyama such as Adachi, KenichiGoushi, KatsuyukiShizu, HirokoNomura, ChihayaAdachi, Nature, 492,234 – 238) the heat lag fluorescent device (ThermallyActivatedDelayedFluorescence, TADF) of inventing then have employed the mode that another utilizes triplet state.They have synthesized the organic molecule with close singlet and triplet by molecular designing, achieving the reverse intersystem crossing of triplet state to singlet, when not having heavy metal atom, achieving internal quantum efficiency 100%.The device architecture of heat lag fluorescent device also uses the Subjective and Objective similar with phosphorescent devices and mixes luminescent layer.
Material of main part many employings carbazole group in existing electroluminescent device, to improve the cavity transmission ability of material.But the C-N chemical bond in carbazole group easily decomposes in the devices, when the molecule containing carbazole is as material of main part, the decomposition probability that C-N is good for increases greatly, likely can affect the weather resistance of device.
Summary of the invention
The technical problem solved: the object of this invention is to provide one not carbazolyl-containing group, good stability, the luminous organic material that luminous efficiency is high and adopt the luminescent device of such material.Such luminous organic material is mainly used in luminescent layer as material of main part.
Technical scheme: for achieving the above object, the invention provides following technical scheme:
Luminous organic material containing spiro-bisfluorene and diphenylene-oxide, has with the structure represented by following formula I, wherein R
1, R
2, R
3, R
4group is hydrogen atom or diphenylene-oxide group, and wherein at least two groups are diphenylene-oxide group, and diphenylene-oxide group is directly connected with covalent single bond by any site with spiro-bisfluorene group;
Further, the described luminous organic material containing spiro-bisfluorene and diphenylene-oxide, wherein the mode of connection of spiro-bisfluorene and diphenylene-oxide is such as formula shown in II ~ formula V, and in formula II ~ formula V, 2 or more diphenylene-oxide are connected with any site of spiro-bisfluorene respectively by its 2 or 4; The site numbering of diphenylene-oxide and spiro-bisfluorene is such as formula shown in VI ~ VII:
Further, the described luminous organic material containing spiro-bisfluorene and diphenylene-oxide, in the compound containing 2 diphenylene-oxide, diphenylene-oxide unit by its 2 or 4 respectively with (2, the 7) position in spiro-bisfluorene group, (3,6) position, (2,2 ') position, (Isosorbide-5-Nitrae ') position, (2,4 ') position, (3,4 ') position or (4,4 ') position connect; In compound containing 3 diphenylene-oxide, diphenylene-oxide unit by its 2 or 4 respectively with (2,2 ', the 7) position in spiro-bisfluorene group, (3,4 ', 6) position, or (2,2 ', 4) position connects; In compound containing 4 diphenylene-oxide unit, diphenylene-oxide unit is connected with (2,2 ', 7, the 7 ') position in spiro-bisfluorene group respectively by its 2 or 4; Connection site in same compound on each diphenylene-oxide unit can be identical or different.
Further, the described luminous organic material containing spiro-bisfluorene and diphenylene-oxide, the connection site in same compound on multiple diphenylene-oxide unit is identical.
Further, the above-described luminous organic material containing spiro-bisfluorene and diphenylene-oxide, described material has following chemical structure:
A kind of luminescent device, there is organic material layer in it, and by electrical energy drive device luminous between the anode and cathode; Containing the above-described luminous organic material containing spiro-bisfluorene and diphenylene-oxide in described organic material layer.
Further, described a kind of luminescent device, described luminescent device contains hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer, any one deck wherein or multilayer contain the above-described luminous organic material containing spiro-bisfluorene and diphenylene-oxide.
Further, described a kind of luminescent device, described luminescent layer is made up of above arbitrary described luminous organic material containing spiro-bisfluorene and diphenylene-oxide and luminophor.
Further, described a kind of luminescent device, above-described containing spiro-bisfluorene and diphenylene-oxide luminous organic material as the material of main part in luminescent layer, luminophor is as guest materials, and luminophor is luminescent metal complexes, luminous organic compound or luminous high polymer material.
Beneficial effect: luminescent material of the present invention can be used for preparing high efficiency electroluminescent device; Luminescent material of the present invention, when not adopting carbazole unit, achieves very high efficiency of luminescent device.Simultaneously in the present invention based in the compound of diphenylene-oxide and spiro-bisfluorene, the similar compound of the compound containing two or more diphenylene-oxide unit comparatively only containing a diphenylene-oxide unit has better luminescent device performance.Luminescent material of the present invention has outstanding physical and chemical performance and electroluminescent device efficiency; Electroluminescent device of the present invention is the high efficiency device that a class has outstanding representation.
Accompanying drawing explanation
Fig. 1 is compd A 11
1hNMR schemes, and solvent is the deuterochloroform containing tetramethylsilane (TMS).
The structural representation of device in Fig. 2 embodiment 2.
The electroluminescent spectrum of device 1 in Fig. 3 embodiment 2.
The electroluminescent spectrum of device 2 in Fig. 4 embodiment 2.
Embodiment
Below in conjunction with the accompanying drawing in the embodiment of the present invention, be described in detail the technical scheme in the embodiment of the present invention, obviously, described embodiment is only the present invention's part embodiment, instead of whole embodiments.Based on the embodiment in the present invention, the every other embodiment that those of ordinary skill in the art obtain under the prerequisite not making creative work, all belongs to the scope of protection of the invention.
The invention provides the luminous organic material shown in a kind of formula I:
Wherein R
1, R
2, R
3, R
4group is hydrogen atom or diphenylene-oxide group, and wherein at least two is diphenylene-oxide group.Compound can containing 2 or more diphenylene-oxide unit and 1 spiro-bisfluorene unit, 3, more finger or 4.Diphenylene-oxide group is directly connected with covalent single bond by any site with spiro-bisfluorene group, the implication in any site: 1 in spiro-bisfluorene, and 1 ', 2,2 ', 3,3 ', 4,4 ', 5,5 ', 6,6 ', 7,7 ', 8, any site in 8 ', shown in VI; In diphenylene-oxide 1,2,3,4,6,7,8, any site in 9, shown in VII.
Diphenylene-oxide unit contains Sauerstoffatom, and the electronegativity of Sauerstoffatom is greater than nitrogen-atoms, and the electronegativity that Sauerstoffatom is higher can give molecule better electron affinity power, and then puies forward high molecular electron transport ability.Diphenylene-oxide has triatomic ring two dimensional structure simultaneously, can improve carrier mobility.In spiro-bisfluorene group, two fluorenes rings are connected by spiral shell carbon, orthogonal.The three-dimensional arrangement of spiro-bisfluorene group can put forward high molecular thermostability, improves the second-order transition temperature of material, improves the film forming stable appearance of molecule.Spiro-bisfluorene has very high luminous quantum efficiency simultaneously, can improve luminous efficiency using spiro-bisfluorene as structural unit.
When diphenylene-oxide in luminescent material is connected with spiro-bisfluorene unit preferably by 2 or 4, the mode of connection of diphenylene-oxide can represent with formula VIII and formula IX, and Ar is spiro-bisfluorene group.
In formula II ~ V, 2 ~ 4 diphenylene-oxide are connected with any site of spiro-bisfluorene with 4 by preferred sites 2.Any site of spiro-bisfluorene refers to: 1,1 ', 2,2 ', 3,3 ', 4,4 ', 5,5 ', 6,6 ', 7,7 ', 8, and 2 in 8 ' or multiple.
When 2 ~ 4 diphenylene-oxide are connected with any site of spiro-bisfluorene with 4 by preferred sites 2, spiro-bisfluorene is preferably following mode of connection: in the compound containing 2 diphenylene-oxide, diphenylene-oxide unit by its 2 or 4 respectively with (2 in spiro-bisfluorene group, 7) position, (3,6) position, (2,2 ') position, (1,4 ') position, (2,4 ') position, (3,4 ') position or (4,4 ') position connect.In compound containing 3 diphenylene-oxide, diphenylene-oxide unit by its 2 or 4 respectively with (2,2 ', the 7) position in spiro-bisfluorene group, (3,4 ', 6) position, or (2,2 ', 4) position connects.In compound containing 4 diphenylene-oxide, diphenylene-oxide unit is connected with (2,2 ', 7, the 7 ') position in spiro-bisfluorene group respectively by its 2 or 4.Multiple diphenylene-oxide unit in same compound, the connection site on each diphenylene-oxide unit can be the same or different, and both multiple diphenylene-oxide can be connected with the spiro-bisfluorene that is combined in of 4 by 2 or 4 or 2.Wherein be preferably multiple diphenylene-oxide by identical site, be both both 2 or be both 4, and be connected with spiro-bisfluorene, be more preferably two diphenylene-oxide by same loci, be both both 2 or be both 4, and be connected with spiro-bisfluorene.
Luminescent material more than containing spiro-bisfluorene and diphenylene-oxide has but is not limited to following structure:
Feature of the present invention has two or more diphenylene-oxide groups in compound, and compared to the similar compound containing single diphenylene-oxide group, the compound in the present invention has better luminescent device performance.In specific embodiment hereinafter, device is carried out to the spiro-bisfluorene compound containing two diphenylene-oxide and a diphenylene-oxide and has compared.
The synthetic method of luminescent material of the present invention can adopt known method.As the method connecting spiro-bisfluorene and diphenylene-oxide, such as, can adopt palladium catalyst, the halogenation spiro-bisfluorene of catalysis halogen substiuted and the boric acid of diphenylene-oxide or boric acid ester carry out the method for reacting, but are not limited only to these methods.
Luminescent material in the present invention, for the preparation of a kind of luminescent device, may be used for any one deck of this device.Below the concrete example of this kind of device is described in detail.Luminescent device of the present invention its there is organic material layer between the anode and cathode, and luminous by electrical energy drive device.
The negative electrode of luminescent device and anode material there is no and specify, and as luminescent device, wherein at least one electrode is transparent or semi-transparent conductive material.
The organic material layer of luminescent device can contain hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer.Luminescent layer can be made up of bi-material, and a kind of material mixes in another kind of material as doping agent, and the material as doping agent is guest materials, and being doped material is material of main part.
Luminescent material of the present invention, in above-mentioned device is formed, in any one deck wherein or multilayer, but can be preferred for luminescent layer, be more preferably as the material of main part in luminescent layer, its reason is, has high triplet, high stability, good carrier transport ability.Luminescent material of the present invention also can be used for hole transmission layer and electron transfer layer, and its reason is the carrier transport ability had.
In luminescent device of the present invention luminescent layer doping agent both guest materials be not particularly limited, be preferably luminescent metal complexes and light-emitting organic molecules.Wherein luminescent metal complexes is more preferably the title complex of iridium and platinum, and light-emitting organic molecules is more preferably fluorescent chemicals and delayed fluorescence compound.Specifically, below dopant configuration is illustrated:
In luminescent device of the present invention, the doping content of luminescent layer doping agent is not particularly limited, and in order to realize preferably device performance, doping content is preferably 1% ~ 20%, is more preferably 5% ~ 15%.
Below enumerate embodiment so that the present invention to be described, but the present invention and can't help these embodiments limit.Embodiment 1 is compounds precedent, and involved chemical feedstocks and reagent are commercially available or synthesize by the document published.Embodiment 2 is the preparation of luminescent device.
The synthesis of embodiment 1 compd A 11
By 1.20 gram 4,4 '-dibromo spiro-bisfluorene and 1.61 grams, 4-diphenylene-oxide boric acid adds in 150 ml flasks, adds catalyst P d (PPh
3)
4250 milligrams, tetrahydrofuran (THF) 60 milliliters, 2MK
2cO
3solution 20 milliliters, argon shield refluxes 24 hours, cools rear dichloromethane extraction, is spin-dried for after organic over anhydrous dried over sodium sulfate, and with methylene dichloride/sherwood oil=1:4 as eluent, silica gel, as stationary phase, carries out column chromatography, is spin-dried for obtain product 1.3 grams.Pass through
1h nuclear-magnetism and mass spectrum determination structure are compd A 11, and nuclear-magnetism as shown in Figure 1.EI-MS：m/z648.2(M
+)。
The preparation of embodiment 2 electroluminescent device
Before fabricate devices, luminescent material of the present invention is all purified further through Vacuum Heat distillation.Take the present invention as the electroluminescent device of luminescent layer material of main part, as shown in Figure 2, glass and conductive glass (ITO) substrate layer 1 can be comprised, hole injection layer 2 (molybdic oxide MoO
3), hole transmission layer 3 (TAPC), the second hole transmission layer 4 (mCP), (material of main part is luminescent material of the present invention to luminescent layer 5, is compd A 11 in this instance, and compound H is then as the material of main part of reference device; Guest materials as doping agent is FIrpic or 4CzIPN), electron transfer layer 6 (TmPyPB), electron injecting layer 7 (lithium fluoride), cathode layer 8 (aluminium), the structure relating to compound is as follows:
Electroluminescent device can make by means known in the art, makes as pressed the disclosed method of reference (Adv.Mater.2003,15,277.).Concrete grammar is: in high vacuum conditions, evaporation MoO successively on conductive glass (ITO) substrate through cleaning
3, TAPC, mCP, luminescent layer, TmPyPB, LiF and Al.Obtain device as shown in Figure 2, the concrete structure of various device by the method, comprise layers of material, thickness, sequentially, in luminescent layer concentration of dopant is as follows:
Device 1:ITO/MoO
3(1nm)/TAPC (40nm)/mCP (10nm)/compd A 11:FIrpic8wt% (20nm)/TmPyPB (20nm)/LiF (1nm)/Al (100nm).
Device 2:ITO/MoO
3(1nm)/TAPC (40nm)/mCP (10nm)/compd A 11:4CzIPN5wt% (20nm)/TmPyPB (30nm)/LiF (1nm)/Al (100nm).
Reference device 1:ITO/MoO
3(1nm)/TAPC (40nm)/mCP (10nm)/compound H: FIrpic8wt% (20nm)/TmPyPB (20nm)/LiF (1nm)/Al (100nm).
Reference device 2:ITO/MoO
3(1nm)/TAPC (40nm)/mCP (10nm)/compound H: 4CzIPN5wt% (20nm)/TmPyPB (30nm)/LiF (1nm)/Al (100nm).
Current versus brightness-the voltage characteristic of device is completed by Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Currentmeter) with corrected silicon photoelectric diode, electroluminescent spectrum is by PhotoResearch company PR655 spectrometer measurement, and all measurements all complete in atmosphere at room temperature.The performance data of device sees the following form:
Device 1 and reference device 1 adopt the complex of iridium FIrpic of blue light-emitting as doping agent, and the electroluminescent spectrum of 2 devices is all blue, and the electroluminescent spectrum of device 1 as shown in Figure 3.The highest external quantum efficiency of device 1/ reference device 1 and maximum power efficiency are respectively 15%/7.4% and 28.6 lumen every watt/14.2 lumen every watt.The A11 containing two diphenylene-oxide is adopted to be adopt to only have the compound H of a diphenylene-oxide to be the twice of the reference device 1 of material of main part as the efficiency of the device 1 of material of main part.Such as, and the result of device 1 will be much better than the similar device of bibliographical information, document Adv.Mater, 2003,15,884.
Device 2 and reference device 2 adopt the luminescent organic molecule 4CzIPN of green light as doping agent, and this doping agent has delayed fluorescence characteristic.The electroluminescent spectrum of 2 devices is all green.The highest external quantum efficiency of device 2/ reference device 2 and maximum power efficiency reach 24.8%/15.4% and 60.6 lumen every watt/30.2 lumen every watt respectively.Same, adopt the A11 containing two diphenylene-oxide to only have the compound H of a diphenylene-oxide to be reference device 2 height about 60% and 100% of material of main part as the external quantum efficiency of the device 2 of material of main part and power efficiency than adopting.The efficiency of device 2 is better than the similar device of bibliographical information simultaneously, such as document Nature, 492,234 – 23.
Claims (9)
1. contain the luminous organic material of spiro-bisfluorene and diphenylene-oxide, it is characterized in that having with the structure represented by following formula I, wherein R
1, R
2, R
3, R
4group is hydrogen atom or diphenylene-oxide group, and wherein at least two groups are diphenylene-oxide group, and diphenylene-oxide group is directly connected with covalent single bond by any site with spiro-bisfluorene group;
2. the luminous organic material containing spiro-bisfluorene and diphenylene-oxide according to claim 1, it is characterized in that, wherein the mode of connection of spiro-bisfluorene and diphenylene-oxide is such as formula shown in II ~ formula V, in formula II ~ formula V, 2 or more diphenylene-oxide are connected with any site of spiro-bisfluorene respectively by its 2 or 4; The site numbering of diphenylene-oxide and spiro-bisfluorene is such as formula shown in VI ~ VII:
3. the luminous organic material containing spiro-bisfluorene and diphenylene-oxide according to claim 2, is characterized in that, in the compound containing 2 diphenylene-oxide, diphenylene-oxide unit by its 2 or 4 respectively with (2, the 7) position in spiro-bisfluorene group, (3,6) position, (2,2 ') position, (Isosorbide-5-Nitrae ') position, (2,4 ') position, (3,4 ') position or (4,4 ') position connect; In compound containing 3 diphenylene-oxide, diphenylene-oxide unit by its 2 or 4 respectively with (2,2 ', the 7) position in spiro-bisfluorene group, (3,4 ', 6) position, or (2,2 ', 4) position connects; In compound containing 4 diphenylene-oxide unit, diphenylene-oxide unit is connected with (2,2 ', 7, the 7 ') position in spiro-bisfluorene group respectively by its 2 or 4; Connection site in same compound on each diphenylene-oxide unit can be identical or different.
4. the luminous organic material containing spiro-bisfluorene and diphenylene-oxide according to claim 3, it is characterized in that, the connection site in same compound on multiple diphenylene-oxide unit is identical.
5., according to the arbitrary described luminous organic material containing spiro-bisfluorene and diphenylene-oxide of claims 1 to 3, it is characterized in that, described material comprises following chemical structure:
6. a luminescent device, there is organic material layer in it, and by electrical energy drive device luminous between the anode and cathode; It is characterized in that: containing the described luminous organic material containing spiro-bisfluorene and diphenylene-oxide arbitrary in claim 1 to 5 in described organic material layer.
7. a kind of luminescent device according to claim 6, described luminescent device contains hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer, it is characterized in that, any one deck wherein or multilayer contain arbitrary described luminous organic material containing spiro-bisfluorene and diphenylene-oxide in claim 1 to 5.
8. a kind of luminescent device according to claim 7, is characterized in that, described luminescent layer is made up of the arbitrary described luminous organic material containing spiro-bisfluorene and diphenylene-oxide of claim 1 to 5 and luminophor.
9. a kind of luminescent device according to claim 8, it is characterized in that, in described claim 1 to 5 arbitrary described containing spiro-bisfluorene and diphenylene-oxide luminous organic material as the material of main part in luminescent layer, luminophor is as guest materials, and luminophor is luminescent metal complexes, luminous organic compound or luminous high polymer material.
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| US10950796B2 (en) | 2017-08-14 | 2021-03-16 | Shanghai Tianma AM-OLED Co., Ltd. | Light-emitting element and display device |
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| US10950796B2 (en) | 2017-08-14 | 2021-03-16 | Shanghai Tianma AM-OLED Co., Ltd. | Light-emitting element and display device |
| CN111440135A (en) * | 2020-04-16 | 2020-07-24 | 烟台显华化工科技有限公司 | Compound, light extraction material and organic electroluminescent device |
| CN111440135B (en) * | 2020-04-16 | 2023-06-23 | 烟台显华化工科技有限公司 | Compound, light extraction material and organic electroluminescent device |
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