CN108727205A - One kind is containing pyrene compound and preparation method thereof and organic luminescent device - Google Patents
One kind is containing pyrene compound and preparation method thereof and organic luminescent device Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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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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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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Abstract
The present invention provides one kind containing pyrene compound, has structure shown in chemical formula 1Wherein, X1And X2It is oxygen (O) or sulphur (S), Y1And Y2It is carbon (C) or nitrogen (N), L1It is 0 or 1, R1And R2Independently selected from hydrogen, C1~C30Alkyl, C6~C30Aryl, C5~C30Heterocycle；It is provided by the invention that there is higher luminous efficiency and longer service life containing pyrene compound.The present invention provides a kind of preparation methods containing pyrene compound, additionally provide a kind of organic luminescent device, including anode, cathode and the organic compound layer being arranged between the anode and cathode, the organic compound layer includes containing pyrene compound described in above-mentioned technical proposal.
Description
Technical field
The present invention relates to field of organic electroluminescence more particularly to a kind of pyrene compound and preparation method thereof and use should
The organic electroluminescence device of material preparation.
Background technology
General organic luminescent device (OLED) is the organic matter layer structure by being inserted between cathode, anode and cathode and anode
At, the composition of device is transparent ITO anode, hole injection layer（TIL）, hole transmission layer（HTL）, luminescent layer（EL, hole resistance
Barrier（HBL）, electron transfer layer（ETL）, electron injecting layer（EIL）, the cathodes such as LiAl formed, it is organic that 1 ~ 2 can be omitted on demand
Layer.Voltage is formed between two electrodes of device injects hole from cathode electronics injection another side anode on one side.This electronics and sky
Cave returns to stable ground state in luminescent layer in conjunction with excitation state, excitation state is formed.Luminescent material is divided into fluorescent material and phosphorescence material
Material, the forming method of luminescent layer is that phosphor material is adulterated in fluorescent host material（Organic metal）Method and fluorescent host material
Doping fluorescent（Include the organic matter of nitrogen）Dopant is utilized in the method and illuminator of dopant（DCM, Rubrene, DCJTB
Deng）The method of the existing long wavelength of tool, in this way mix improvement emission wavelength, efficiency, driving voltage, the factors such as service life.Generally
Forming emitting layer material is matched with centerbodies and benzene, biphenyl, naphthalene, heterocycle etc. such as benzene, naphthalene, fluorenes, two fluorenes of spiral shell, anthracene, pyrene, carbazoles
Body；The replacing structures such as contraposition, meta position, the binding site at ortho position and cyano, fluorine, methyl, tertiary butyl.
Oled panel develops to enlargement and needs finer and smoother and the distincter material of color, predominantly blue material, especially
Being that needs are light blue moves on to navy blue high performance material, and the luminescent material that present technology provides is in luminous efficiency and in terms of the service life
There is still a need for further increase to meet requirement.
Invention content
In view of this, the purpose of the present invention is to provide one kind containing pyrene compound and preparation method thereof and organic illuminator
Part, it is provided by the invention in luminous efficiency and to there is preferable performance in terms of the service life containing pyrene compound.
The present invention provides one kind containing pyrene compound, has structure shown in chemical formula 1：
[chemical formula 1]
X1And X2It is oxygen (O) or sulphur (S), Y1And Y2It is carbon (C) or nitrogen (N), L1It is 0 or 1, R1And R2Independently selected from hydrogen, C1~
C30Alkyl, C6~C30Aryl, C5~C30Heterocycle.
Preferably, the pyrene compound that contains is that any one chemical formula indicates in following chemical formula 2-1 ~ chemical formula 2 ~ 10
Pyrene compound：
[chemical formula 2-1]
[chemical formula 2-2]
[chemical formula 2-3]
[chemical formula 2-4]
[chemical formula 2-5]
[chemical formula 2-6]
[chemical formula 2-7]
[chemical formula 2-8]
[chemical formula 2-9]
[chemical formula 2-10]
[compound 2-11]
Wherein, R1And R2Independently selected from hydrogen, C1~C30Alkyl, C6~C30Aryl, C5~C30Heterocycle.
Preferred R1And R2Independently selected from from hydrogen, methyl, ethyl, the fluoro- ethyls of 2-, 2- cyano-propyls, isopropyl, tertiary fourth
Any one structure in base, pentyl, heptane base, dodecyl or formula b-1 to b-11；
Formula b-1,Formula b-2,Formula b-3,Formula b-4,Formula b-5,Formula b-6,
Formula b-7,Formula b-8,Formula b-9,
Formula b-10,Formula b-11,Formula b-12,
Formula b-13,Formula b-14,Formula b-15,
Formula b-16,Formula b-17,Formula b-18,Formula b-19；
Wherein, RgFor halogen, amino, cyano, nitro, hydroxyl or sulfydryl；RgAny position on substituent group, RgNumber be 0
~ 5；At scission of link.
It is preferably, described that there is formula A-1 ~ A-12, B-1 ~ B-6, C-1 ~ C-11, D-1 ~ D-5, E-1 ~ E-5 containing pyrene compound,
The particular compound that any one chemical formula of F-1 ~ F-9, G-1 ~ G-7, H-1 ~ H-5, I-1 ~ I-6, L-1 ~ L-4 indicates：
Wherein, the end group not provided is methyl.
The present invention provides a kind of preparation methods containing pyrene compound, include the following steps：
1）By formula（I）The compound and formula of shown structure（II）The compound of shown structure is reacted, and intermediate product is obtained；Institute
Intermediate product is stated with structure shown in formula D-1：
2）By the intermediate product product and formula（III）The compound of shown structure is reacted, and obtains containing shown in chemical formula 1
Pyrene compound；
Formula（I）；Formula（II）；
Formula（III）；Formula（Ⅳ）；
Chemical formula 1；
Wherein, R1And R2It is independent to be selected from hydrogen, substituted or unsubstituted C1~C60Alkyl, substituted or unsubstituted C6~C30Virtue
Base.
The present invention is by formula（I）The compound and formula of structure（II）The compound of structure is reacted, and intermediate product is obtained.?
In the present invention, formula（I）With formula（II）The temperature that compound is reacted is preferably 90 DEG C ~ 110 DEG C, more preferably 95 DEG C ~ 105
DEG C, most preferably 100 DEG C.In the present invention, formula（I）With formula（II）The time that compound is reacted is preferably 20 hours ~ 30
Hour, more preferably 24 hours ~ 26 hours.In the present invention, it is preferred under stirring conditions by formula A-1 and formula B-1 compounds
It is reacted.In the present invention, it is preferred to which formula A-1 and formula B-1 compounds are reacted under the protection of nitrogen.In the present invention
In, preferably in a solvent by formula（I）And formula（II）Compound reacted, the solvent is preferably toluene.In the present invention,
It is preferred that by the change of formula A-1 and formula B-1 structures under the action of three (dibenzylideneacetone) two palladium, tri-tert-butylphosphine and sodium tert-butoxide
Object is closed to be reacted.In the present invention, the formula（I）And formula（II）The molar ratio of structural compounds is preferably（0.08~0.12）：
（0.08~0.15）, more preferably（0.09~0.13）：（0.1~0.13）, most preferably 0.1:0.12.
In the present invention, formula（III）Compound and formula（Ⅳ）The reaction temperature of intermediate product, reaction is obtained by the reaction in compound
The method of time, reaction condition and post-processing, with formula described in above-mentioned technical proposal（I）Compound and formula（II）Compound is reacted
Reaction temperature, reaction time, reaction condition and the method for post-processing for obtaining intermediate product are consistent, and details are not described herein.
The present invention is to formula（I）And formula（II）The source of compound does not have special limitation, can be bought and be obtained by market, may be used yet
It is prepared according to method well known to those skilled in the art.
Formula（I）The compound and formula of shown structure（II）Intermediate product is obtained by the reaction in the compound of shown structure（Ⅳ）Afterwards,
The present invention is by the intermediate product product and formula（III）The compound of shown structure is reacted, and obtains containing shown in chemical formula 1
Pyrene compound.In the present invention, reacting containing pyrene compound shown in chemical formula 1 is obtained by the reaction with formula C compounds in intermediate product
Temperature, reaction time, reaction condition and the method for post-processing, with intermediate product described in above-mentioned technical proposal and formula C compounds
It is consistent that reaction temperature shown in Formulas I containing pyrene compound, reaction time, reaction condition and the method for post-processing is obtained by the reaction,
Details are not described herein.
Preparation process provided by the invention containing pyrene compound 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 include described in above-mentioned technical proposal contain pyrene compound.In the present invention
In, described consistent containing pyrene compound with described in above-mentioned technical proposal containing pyrene compound, details are not described herein.In the present invention,
The organic luminescent device preferably includes cathode, anode and the one or more compounds being arranged between the cathode and anode
Layer, the compound layer include containing pyrene compound described in above-mentioned technical proposal.In the present invention, the compound layer can be complete
It is formed, can also be made of the mixture containing pyrene compound and other substances by containing pyrene compound entirely.In the present invention, describedization
Nitride layer is closed to include hole injection layer, hole transmission layer, both had technical ability layer, electronic blocking of the hole injection but also with hole transport
Layer, hole blocking layer, electron transfer layer, electron injecting layer, had both had technical ability of the electron-transport but also with electron injection at luminescent layer
One or more of layer.In the present invention, the hole injection layer, hole transmission layer, both had hole injection but also with sky
Cave transmission technical ability layer in may be used conventional hole injecting material, hole transporting material, 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
Contain pyrene compound.In the present invention, the luminescent layer includes in phosphorescence host, fluorescent host, phosphorescence doping and fluorescence doping
One or more.In the present invention, the pyrene compound that contains may be used as fluorescent host, can also be used as fluorescence and mix
It is miscellaneous, and fluorescent host and fluorescence is used as to adulterate simultaneously.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 the above-mentioned pyrene compound that contains as cyan main body or blueness
Color adulterates, and high efficiency, high-resolution, high brightness and the luminescent device of long-life can be obtained.
In the present invention, the compound layer preferably includes electron transfer layer, and the electron transfer layer includes above-mentioned technology
Contain pyrene compound described in scheme.In the present invention, the electron transfer layer preferably further includes metallic compound.
In the present invention, the compound layer preferably includes luminescent layer and electron transfer layer, and the luminescent layer and electronics pass
Defeated layer containing containing pyrene compound described in above-mentioned technical proposal, in the luminescent layer and electron transfer layer can containing pyrene compound
It can also be different with identical.
The present invention does not have the preparation method of the organic luminescent device special limitation, 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 can be utilized
The methods of physical vapor deposition evaporation metal, conductive oxide and their alloy on substrate form anode；It is cloudy
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 molding（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.
Organic luminescent device provided by the invention containing pyrene compound using being prepared described in above-mentioned technical proposal.It is 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 is 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.
Specific implementation mode：
Embodiment 1 ~ 70
The preparation of intermediate 2- Methoxy-N-phenyls Aniline intermediates 1
Aniline 0.10mol and sodium tert-butoxide 0.30mol, toluene 400mL are added in reaction bulb, stirred 30 minutes, nitrogen is protected
Then the bromo- 2- methoxybenzenes 0.12mol of 1-, three intermediate dibenzylideneacetones are added in shield) two palladium 1.5g, it is eventually adding three uncles
Butyl phosphine 4g is warming up to 100 DEG C and reacts 24 hours.
Reaction system is cooled down after the completion of reaction, water is added and terminates reaction, filtering by filtrate liquid separation, is spin-dried for toluene, is added
A small amount of dichloromethane dissolving is spin-dried for rear product, using petroleum ether:Dichloromethane=3:1（Volume ratio）Post separation is crossed, 2- methoxies are obtained
Base-N- phenylanilines（Intermediate D-1）Intermediate 0.05mol, y=50%).
Using the method described in above-mentioned technical proposal, intermediate 2 is prepared into according to the reaction raw materials provided in table 1
Mesosome 70, table 1 are to prepare intermediate 2 to the reaction mass of intermediate 70.
Table 1 prepares intermediate 2 to the reaction mass of intermediate 70
Embodiment 71 ~ 140
The preparation of embodiment A-1
By 2- Methoxy-N-phenyl amine 0.10mol and sodium tert-butoxide 0.30mol, toluene 400mL is added in reaction bulb, stirring
30 minutes, then 1,6-, bis- bromo- 3,8- diisopropyls pyrene 0.12mol, three (dibenzylideneacetone) two palladium is added in nitrogen protection
1.5g is eventually adding tri-tert-butylphosphine 4g, is warming up to 100 DEG C and reacts 24 hours.
Obtained reaction system is cooled down, water is added and terminates reaction, filtering, the filtrate liquid separation that will be obtained is spin-dried for toluene, adds
Enter a small amount of dichloromethane dissolved solid, using petroleum ether:Dichloromethane=3:1（Volume ratio）Post separation is crossed, obtains containing pyrene compound
A-1 (0.05mol, y=50%).
To being prepared Mass Spectrometer Method is carried out containing pyrene compound, testing result 680.36, the embodiment of the present invention 71 ~
140 structures containing pyrene compound with A-1 in table 2 being prepared.
Using the method described in above-mentioned technical proposal, it is prepared containing pyrene compound according to the reaction raw materials provided in table 2
A-1 ~ A-12, B-1 ~ B-6, C-1 ~ C-11, D-1 ~ D-5, E-1 ~ E-5, F-1 ~ F-9, G-1 ~ G-7, H-1 ~ H-5, I-1 ~ I-6, L-1
~ L-4, table 2 are to prepare A-1 containing pyrene compound ~ A-12, B-1 ~ B-6, C-1 ~ C-11, D-1 ~ D-5, E-1 ~ E-5, F-1 ~ F-9, G-1
~ G-7, H-1 ~ H-5, the reaction mass of I-1 ~ I-6, L-1 ~ L-4.
2 A-1 containing pyrene compound of table ~ A-12, B-1 ~ B-6, C-1 ~ C-11, D-1 ~ D-5,
The reaction mass of E-1 ~ E-5, F-1 ~ F-9, G-1 ~ G-7, H-1 ~ H-5, I-1 ~ I-6, L-1 ~ L-4
The preparation of 141 ~ 147 organic luminescent device of embodiment
The ito glass substrate that Fisher Co., Ltd's coating layer thickness is 1500 is placed in distilled water and is cleaned 2 times, ultrasonic washing 30
Minute, then cleaned repeatedly with distilled water 2 times, ultrasonic washing 10 minutes, after distilled water cleans, using isopropanol, acetone,
Methanol solvate carries out drying after ultrasonic washing in order, and the substrate after drying is transferred in plasma washing machine, will be upper
Substrate washing is stated to be sent in evaporator after five minutes.
Be deposited successively on cleaned ito transparent electrode hole injection layer 2-TNATA evaporation thickness be 500,
Hole transmission layer a-NPD evaporation thickness is to contain pyrene compound in 300, ADN (9,10- bis- (2- naphthalenes) anthracene) and 5% table 3
Evaporation thickness is 300, and hole blocking layer and electron transfer layer TPBi evaporation thickness are 400, and cathode is that LiF evaporation thickness is
5, it is 2000 that anode, which is Al evaporation thickness,；Above process organic matter vaporization plating speed keeps 1/sec, the evaporation rate of LiF
Evaporation rate for 0.2/sec, Al is 3 ~ 7/sec.Table 3 is embodiment and the organic illuminator that comparative example is prepared
The performance test results of part.
The structural formula of 2-TNATA is：The structural formula of a-NPD is：
The structural formula of AND is：The structural formula of TPBi is：
Embodiment A-1 ~ A-4 is had rated with scanning optical spectrum luminance meter PhotoResearchPR670, Keithley238 measuring device
And efficiency (the current density 20mA/cm of the organic illuminating element manufactured in comparative experiments example2), lifetime data (50mA/cm2) and
Color, and result is shown in the following table 3, the efficiency in the following table 3 refers to relative efficiency, and the service life refers to comparative lifetime.
Comparative example 1
Organic luminescent device is prepared according to the preparation method of the organic luminescent device described in embodiment 141 ~ 147, difference lies in make
It is replaced with DPAP-DPPA and contains pyrene compound；
The structural formula of DPAP-DPPA is：
According to the method described in above-mentioned technical proposal, current density, the face of the organic luminescent device that detection comparative example 1 is prepared
Color, efficiency and service life, the results are shown in Table 3.
The performance test results for the organic luminescent device that 3 embodiment of table and comparative example are prepared
As shown in Table 3, organic luminescent device, the luminous effect of organic luminescent device are prepared containing pyrene compound using provided by the invention
Rate and service life significantly improve.
As seen from the above embodiment, the present invention provides one kind containing pyrene compound, has structure shown in Formulas I；Wherein, X1
And X2It is oxygen (O) or sulphur (S), Y1And Y2It is carbon (C) or nitrogen (N), L1It is 0 or 1, R1And R2Independently selected from hydrogen, C1~C30Alkyl,
C6~C30Aryl, C5~C30Heterocycle.It is provided by the invention that there is higher luminous efficiency and longer service life containing pyrene compound.
What has been described above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill of the art
For personnel, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications
It should be regarded as protection scope of the present invention.
Claims (6)
1. one kind containing pyrene compound, there is structure shown in chemical formula 1：
[chemical formula 1]
Wherein, X1And X2It is oxygen (O) or sulphur (S), Y1And Y2It is carbon (C) or nitrogen (N), L1It is 0 or 1, R1And R2Independently selected from hydrogen,
C1~C30Alkyl, C6~C30Aryl, C5~C30Heterocycle.
2. it is according to claim 1 contain pyrene compound, which is characterized in that it is described containing pyrene compound be following chemical formula 2-1 ~
Arbitrary chemical formula in chemical formula 2 ~ 10：
[chemical formula 2-1]
[chemical formula 2-2]
[chemical formula 2-3]
[chemical formula 2-4]
[chemical formula 2-5]
[chemical formula 2-6]
[chemical formula 2-7]
[chemical formula 2-8]
[chemical formula 2-9]
[chemical formula 2-10]
[compound 2-11]
Wherein, R1And R2Independently selected from hydrogen, C1~C30Alkyl, C6~C30Aryl, C5~C30Heterocycle.
3. according to claim 1 or 2 contain pyrene compound, which is characterized in that R1And R2Independently selected from from hydrogen, methyl, second
In the fluoro- ethyl of base, 2-, 2- cyano-propyls, isopropyl, tertiary butyl, pentyl, heptane base, dodecyl or formula b-1 to b-11
Any one structure；
Formula b-1,Formula b-2,Formula b-3,Formula
B-4,Formula b-5,Formula b-6,
Formula b-7,Formula b-8,Formula b-9,
Formula b-10,Formula b-11,Formula b-12,
Formula b-13,Formula b-14,Formula b-15,
Formula b-16,Formula b-17,Formula b-18,Formula b-19；
Wherein, RgFor halogen, amino, cyano, nitro, hydroxyl or sulfydryl；RgAny position on substituent group, RgNumber be 0
~ 5；At scission of link.
4. according to claim 1 contain pyrene compound, which is characterized in that it is described that there is formula A-1 ~ A-12 containing pyrene compound,
B-1 ~ B-6, C-1 ~ C-11, D-1 ~ D-5, E-1 ~ E-5, F-1 ~ F-9, G-1 ~ G-7, H-1 ~ H-5, I-1 ~ I-6, L-1 ~ L-4 are arbitrary
The particular compound that one chemical formula indicates：
。
5. the present invention provides a kind of preparation method containing pyrene compound, include the following steps：
1）By formula（I）The compound and formula of shown structure（II）The compound of shown structure is reacted, and intermediate product is obtained；Institute
Intermediate product is stated with structure shown in formula D-1：
2）By the intermediate product product and formula（III）The compound of shown structure is reacted, and obtains containing shown in chemical formula 1
Pyrene compound；
Formula（I）；Formula（II）；
Formula（III）；Formula（Ⅳ）；Change
Formula 1；
Wherein, R1And R2It is independent to be selected from hydrogen, substituted or unsubstituted C1~C60Alkyl, substituted or unsubstituted C6~C30Virtue
Base.
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 compound layer includes containing pyrene compound described in any one of claim 1 ~ 4.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN111848416A (en) * | 2019-04-29 | 2020-10-30 | 南京高光半导体材料有限公司 | Pyrene blue fluorescence doping substance and organic electroluminescent device containing pyrene blue fluorescence doping substance |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109678731A (en) * | 2019-01-31 | 2019-04-26 | 北京诚志永华显示科技有限公司 | Organic compound, electroluminescent organic material, electronic equipment |
| CN109678731B (en) * | 2019-01-31 | 2022-01-04 | 石家庄诚志永华显示材料有限公司 | Organic compound, organic electroluminescent material, and electronic device |
| CN111848416A (en) * | 2019-04-29 | 2020-10-30 | 南京高光半导体材料有限公司 | Pyrene blue fluorescence doping substance and organic electroluminescent device containing pyrene blue fluorescence doping substance |
| WO2020220510A1 (en) * | 2019-04-29 | 2020-11-05 | 南京高光半导体材料有限公司 | Pyrene blue fluorescent dopant, and organic electroluminescent device comprising same |
| CN111848416B (en) * | 2019-04-29 | 2021-09-14 | 南京高光半导体材料有限公司 | Pyrene blue fluorescence doping substance and organic electroluminescent device containing pyrene blue fluorescence doping substance |
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