CN107573357A - A kind of organic electroluminescent compounds - Google Patents
A kind of organic electroluminescent compounds Download PDFInfo
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- CN107573357A CN107573357A CN201610522101.4A CN201610522101A CN107573357A CN 107573357 A CN107573357 A CN 107573357A CN 201610522101 A CN201610522101 A CN 201610522101A CN 107573357 A CN107573357 A CN 107573357A
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Abstract
The invention provides a kind of organic electroluminescent compounds, and it has following formula（Ⅰ）Or（Ⅱ）Or（Ⅲ）Shown structure：,, wherein, R1~R8For：H, halogen, cyano group, C1 ~ C20 alkyl group, C1 ~ C20 halogenated alkane base, C3 ~ C20 cycloalkyl, C3 ~ C20 halogenated cycloalkyl, C1 ~ C20 alkoxy, C1 ~ C20 silylation, the aryloxy group that cyclic carbon number is 6 ~ 30, the aryl that cyclic carbon number is 6 ~ 30 and heterocyclic arene base that cyclic carbon number is 6 ~ 30；M and n is 0 or 1；When m and/or n is 1, L1And/or L2The aryl for being 6 ~ 30 for cyclic carbon number or the heterocyclic arene base that cyclic carbon number is 6 ~ 30；X1~X2It is each independently selected from：O、S、S=O、O=S=O；X3~X4It is each independently selected from：C、N.Using the OLED service life of compound preparation is long, heat decomposition temperature is higher, heat endurance is good, and there is excellent luminous efficiency and excitation.
Description
Technical field
The present invention relates to electroluminescent organic material, more particularly to a kind of organic electroluminescent compounds.
Background technology
Organic light emitting diode（Organic Light-Emitting Diodes, hereinafter referred " OLED "）Due to
Self luminous characteristic, compared to lcd technology, there is high-contrast, wide viewing angle, respond fast, low in energy consumption, color reprodubility
Huge advantage that is good and can realizing flexible device, extensive commercial applications are obtained in display and lighting field.
With the development of electroluminescent organic material, red light material and green light material have substantially met the needs of display.
However, feature of the blue light material due to its broad-band gap, electric charge injection is difficult, luminous efficiency and in terms of the life-span relative to feux rouges and
Green glow is backward.In addition, the operating voltage of some blue light material of in the market is higher, the colour that can reach is also undesirable.
However, blue-light-emitting, the performance of particularly dark blue light, has important influence for improving display quality and reducing power consumption.
Improve the service life of OLED blue light materials and the key of colour in the organic electroluminescent compounds in device
Selection.According to prior art, the organic electroluminescent compounds that can be used as OLED blue light materials have numerous species, wherein using
Extensive compound is the aromatic amine of the aromatic group containing one or more condensed ring and/or indeno fluorene group；Such as patent
Pyrene-arylamine disclosed in pyrene-arylamine and WO2012048780 disclosed in US5153073；And for example,
Benzo indeno fluorenamine disclosed by WO2008006449；And dibenzo indeno fluorenamine disclosed in WO2007170847 etc..
In addition, part prior art, which also discloses the fluorenamine containing aromatic group thick and in fluorenes system, can be used as OLED
Blue light material.For example, the technical scheme disclosed by US20120161615, wherein used compound contain it is two or more
Arylamine group；However, the blue light that this chemical combination objects system is sent is simultaneously inadequate " pure ", what is shown is that green lights to sapphire.
In addition, KR2009131536 and WO2004061048 also disclose a series of benzo fluorene derivatives with diphenyl amino.
However, often there is following defect in the various compounds disclosed in the prior art above：The blue light wavelength mistake sent
It is short, human eye has been injured；Or the efficiency showed in the devices and the life-span it is not good enough；And excitation is poor, can not meet
The requirement of user.
Therefore, high efficiency, long-life and the high blue emitting material of excitation are developed, especially develop high efficiency,
Long-life and the high navy blue luminescent material of excitation, for promoting the development of ORGANIC ELECTROLUMINESCENCE DISPLAYS and lighting engineering to have
Great meaning.
The content of the invention
In view of many disadvantages present in prior art and deficiency, the present invention is intended to provide a kind of organic electroluminescent chemical combination
Thing, as the organic electroluminescence blue emitting material that luminous efficiency is high, service life is long, colour purity is high.Therefore, of the invention
On the one hand, there is provided a kind of organic electroluminescent compounds, it has following formula（Ⅰ）Or（Ⅱ）Or（Ⅲ）Shown structure：
(Ⅲ)
Wherein, R1~R8It is each independently selected from：H, halogen, cyano group, C1 ~ C20 alkyl group, C1 ~ C20 halogenated alkane base, C3
~ C20 cycloalkyl, C3 ~ C20 halogenated cycloalkyl, C1 ~ C20 alkoxy, C1 ~ C20 silylation, substituted or unsubstituted
Cyclic carbon number be 6 ~ 30 aryloxy group, the aryl that substituted or unsubstituted cyclic carbon number is 6 ~ 30 and substituted or without taking
The cyclic carbon number in generation is 6 ~ 30 heterocyclic arene base；
Wherein, m and n is each independently 0 or 1；When m and/or n is 1, L1And/or L2For substituted or unsubstituted cyclization
The aryl that carbon number is 6 ~ 30 or the heterocyclic arene base that substituted or unsubstituted cyclic carbon number is 6 ~ 30；
Wherein, X1~X2It is each independently selected from：O、S、S=O、O=S=O；
Wherein, X3~X4It is each independently selected from：C、N.
Preferably, in above-mentioned organic electroluminescent compounds, R1~R8It is each independently selected from：H, C1 ~ C20 alkane
Base, C3 ~ C20 cycloalkyl, substituted or unsubstituted cyclic carbon number be 6 ~ 30 aryl and it is substituted or unsubstituted into
Ring carbon number is 6 ~ 30 heterocyclic arene base.
It is further preferred that in above-mentioned organic electroluminescent compounds, R1~R8It is each independently selected from：H, methyl, second
Base, isopropyl, n-propyl, phenyl, naphthyl, p-methylphenyl, o-tolyl, a tolyl, to tert-butyl-phenyl, to trifluoromethyl
Phenyl.
Preferably, in above-mentioned organic electroluminescent compounds, m and n are 0.
Preferably, in above-mentioned organic electroluminescent compounds, m and/or n are 1, and L1And/or L2For unsubstituted cyclization
Carbon number is 6 ~ 30 aryl.
Preferably, in above-mentioned organic electroluminescent compounds, X1~X2It is O.
Preferably, in above-mentioned organic electroluminescent compounds, X3~X4It is simultaneously C or N.
Preferably, above-mentioned organic electroluminescent compounds are selected from following any：
The second aspect of the present invention, there is provided a kind of OLED luminescent layers dopant material, it contains first aspect present invention offer
The organic electroluminescent compounds.
The third aspect of the present invention, there is provided a kind of OLED, it, which contains the described of first aspect present invention offer, has
Organic electro luminescent compounds.
In a word, using formula（Ⅰ）Or（Ⅱ）Or（Ⅲ）Shown organic electroluminescent compounds are used as OLED luminescent layers
Dopant material, the OLED service life length of gained, heat decomposition temperature is higher, heat endurance is good, and is lighted with higher
Efficiency and excitation.Therefore, organic electroluminescent compounds provided by the present invention are with a wide range of applications and outstanding
Market potential;The organic electroluminescent compounds be especially suitable as high efficiency, the long-life and excitation it is high navy blue hair
Luminescent material, the development of ORGANIC ELECTROLUMINESCENCE DISPLAYS and lighting engineering is promoted to a certain extent.
Embodiment
The first aspect of the present invention, there is provided a kind of organic electroluminescent compounds, it has following formula（Ⅰ）Or（Ⅱ）Or
（Ⅲ）Shown structure：
Wherein, R1~R8It is each independently selected from：H, halogen, cyano group, C1 ~ C20 alkyl group, C1 ~ C20 halogenated alkane base, C3
~ C20 cycloalkyl, C3 ~ C20 halogenated cycloalkyl, C1 ~ C20 alkoxy, C1 ~ C20 silylation, substituted or unsubstituted
Cyclic carbon number be 6 ~ 30 aryloxy group, the aryl that substituted or unsubstituted cyclic carbon number is 6 ~ 30 and substituted or without taking
The cyclic carbon number in generation is 6 ~ 30 heterocyclic arene base；
Wherein, m and n is each independently 0 or 1；When m and/or n is 1, L1And/or L2For substituted or unsubstituted cyclization
The aryl that carbon number is 6 ~ 30 or the heterocyclic arene base that substituted or unsubstituted cyclic carbon number is 6 ~ 30；
Wherein, X1~X2It is each independently selected from：O、S、S=O、O=S=O；
Wherein, X3~X4It is each independently selected from：C、N.
In a preferred embodiment, R1~R8It is each independently selected from：H, C1 ~ C20 alkyl group, C3 ~ C20 cycloalkanes
Base, the aryl that substituted or unsubstituted cyclic carbon number is 6 ~ 30 and substituted or unsubstituted cyclic carbon number be 6 ~ 30 it is miscellaneous
Cyclophane alkyl.
In a further preferred embodiments, R1~R8It is each independently selected from：H, methyl, ethyl, isopropyl, positive third
Base, phenyl, naphthyl, p-methylphenyl, o-tolyl, a tolyl, to tert-butyl-phenyl, p-trifluoromethyl phenyl.
In a preferred embodiment, m and n is 0.
In a preferred embodiment, in above-mentioned organic electroluminescent compounds, m and/or n are 1, and L1And/or L2For
Unsubstituted cyclic carbon number is 6 ~ 30 aryl.
In a preferred embodiment, X1~X2It is O.
In a preferred embodiment, X3~X4It is simultaneously C or N.
In a preferred embodiment, above-mentioned organic electroluminescent compounds are selected from following any：
。
The second aspect of the present invention, there is provided a kind of OLED luminescent layers dopant material, it contains first aspect present invention and carried
The organic electroluminescent compounds supplied.
The third aspect of the present invention, there is provided a kind of OLED, it, which contains the described of first aspect present invention offer, has
Organic electro luminescent compounds.
With reference to embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.
Methods described is conventional method unless otherwise specified；The raw material can obtain from open commercial sources unless otherwise specified.
The preparation of the compound 3 of embodiment 1
Step 1：Synthetic intermediate 1
By raw material 1（11.6 g, 55 mmol）With 2,5- dibromoterephthalic acid methyl esters（17.6 g, 50 mmol）It is dissolved in 200
In ml toluene solution, 50 ml 2M aqueous sodium carbonate and 50 ml ethanol are then added, is vented 30 minutes with nitrogen
Afterwards, catalyst four is added（Triphenylphosphine）Palladium（Pd(PPh3)4, 3.5 g, 3.0 mmol）, under stirring condition, 100 DEG C are heated to,
After reaction 15 hours, room temperature during cooling, dichloromethane and deionized water are added, extract organic phase, after being dried with anhydrous magnesium sulfate,
Filtering, decompression, concentration, with silicagel column separating-purifying, obtain the pure g of intermediate 1 about 21.6（41 mmol）, yield is about 82%.
Mass spectrum MS [the ESI of intermediate 1+] m/z=526.22 (theoretical value 526.14).
Step 2：Synthetic intermediate 2
By diphenyl-methane（12.6g, 75 mmol）It is dissolved in 200 ml anhydrous tetrahydro furan, ice bath is cooled to 0 DEG C, in argon
Under gas shielded, n-butyllithium solution is slowly injected into（2.5M, 32 ml）；After reacting 1 hour on this condition, it will be dissolved in anhydrous
The intermediate 1 of tetrahydrofuran（13.2g, 25.0 mmol）Solution is slowly injected into above reaction system, and first reaction 2 is small at 0 DEG C
When, room temperature is warming up to, continues reaction 1 hour.Then a small amount of ethanol is injected toward reaction system, round-bottomed flask is poured into, by tetrahydrochysene furan
Solvent under reduced pressure of muttering distills, then anhydrous toward addition dichloromethane and deionized water in reaction system, stirring, extraction organic phase, use
Magnesium sulfate is dried, and filtering, decompression, concentration, with silicagel column separating-purifying, eluant, eluent is petroleum ether/dichloromethane (v:v)=2:1；
Obtain the pure g of intermediate 2 about 10.5（13.5 mmol）, yield is about 54%.
Mass spectrum MS [the ESI of intermediate 2+] m/z=774.35 (theoretical value 774.28).
Step 3：Synthetic intermediate 3
By intermediate 2（10.5g 13.5mmol）It is dissolved in 100 ml glacial acetic acid, then adds the watery hydrochloric acid of catalytic amount（5
mol%, 12 N）, whole reaction system is heated to flowing back, and after reaction 12 hours, is cooled to room temperature, after solvent under reduced pressure is rotated,
With silicagel column separating-purifying, eluant, eluent is petroleum ether/dichloromethane (v:v)=1:1；Obtain the pure g of intermediate 3 about 8.1（11.0
mmol）, yield is about 81%.
Mass spectrum MS [the ESI of intermediate 3+] m/z=738.97 (theoretical value 738.87).
Step 4：Synthetic intermediate 4
By intermediate 3（8.1 g, 11.0 mmol）It is dissolved in 60 ml carbon tetrachloride, then by bromine（3.7g, 23 mmol）
It was slowly added thereto in 30 minutes, after reacting 2 days at room temperature, has solid precipitation, directly by solid filtered on buchner funnel
Out, and with n-hexane wash repeatedly, then with ethyl acetate/n-hexane（1:1）Recrystallization, obtains the g of white powder 5.6
（6.2 mmol）, as intermediate 4, yield 56%.
Mass spectrum MS [the ESI of intermediate 4+] m/z=896.79 (theoretical value 896.66).
Step 5：Synthetic intermediate 5
By the 4- tert-butyl group -1- aniline（14.9 g, 100 mmol）, the 4- tert-butyl group -1- bromobenzenes（21.2 g, 100 mmol）, double (two
Benzyl subunit acetone) palladium（1.7 g, 3 mmol）, tri-butyl phosphine（1.2 g, 6 mmol）And toluene（200 ml）Mixture,
90 DEG C are heated under argon stream, adds sodium tert-butoxide（0.6 g, 6 mmol）Afterwards, 110 DEG C are heated under an argon atmosphere, are stirred
Mix reaction 12 hours.Reactant mixture is cooled to room temperature, water is added and carries out liquid separation.The solvent of the organic layer of gained is carried out dense
Contracting, the solid of gained is purified with silica gel column chromatography, obtains intermediate 5（20.2 g, 72 mmol）, 72% yield.
Mass spectrum MS [the ESI of intermediate 5+] m/z=282.34 (theoretical value 281.44).
Step 6：Synthesize compound 3
By intermediate 4（2.68 g, 3 mmol）, intermediate 5（2.2 g, 8 mmol）, double (dibenzyl subunit acetone) palladiums（34 mg,
0.06 mmol）, tri-butyl phosphine（24 mg, 0.12 mmol）And toluene（50 ml）Mixture, heated under argon stream
To 90 DEG C, sodium tert-butoxide is added（12 mg, 0.12 mmol）, 110 DEG C are heated under an argon atmosphere, and stirring reaction 16 is small
When.Reactant mixture is cooled to room temperature, water is added and carries out liquid separation.The solvent of the organic layer of gained is concentrated, by gained
Solid purified with silica gel column chromatography, obtain target product compound 3（2.6 g, 2 mmol）, 66% yield.
Mass spectrum MS [the ESI of compound 3+] m/z=1296.76 (theoretical value 1296.65).
The preparation of the compound 10 of embodiment 2
Step 1 is to four：Synthetic intermediate 1-4
Intermediate 1-4 synthetic method is identical with embodiment 1 with specific steps.
Step 5：Synthetic intermediate 6
By aniline（9.3 g, 100 mmol）, 4- Trifluoromethyl-1s-bromobenzene（22.4 g, 100 mmol）, double (dibenzyl subunits third
Ketone) palladium（1.7 g, 3 mmol）, tri-butyl phosphine（1.2 g, 6 mmol）And toluene（200 ml）Mixture, in argon stream
Under be heated to 90 DEG C, add sodium tert-butoxide（0.6 g, 6 mmol）Afterwards, 110 DEG C are heated under an argon atmosphere, stirring reaction 12
Hour.Reactant mixture is cooled to room temperature, water is added and carries out liquid separation.The solvent of the organic layer of gained is concentrated, by institute
The solid obtained is purified with silica gel column chromatography, obtains intermediate 5（16.6 g, 70 mmol）, 70% yield.
Mass spectrum MS [the ESI of intermediate 5+] m/z=237.19 (theoretical value 237.08).
Step 6：Synthesize compound 10
By intermediate 4（2.68 g, 3 mmol）, intermediate 6（1.9 g, 8 mmol）, double (dibenzyl subunit acetone) palladiums（34 mg,
0.06 mmol）, tri-butyl phosphine（24 mg, 0.12 mmol）And toluene（50 ml）Mixture, heated under argon stream
To 90 DEG C, sodium tert-butoxide is added（12 mg, 0.12 mmol）Afterwards, 110 DEG C are heated under an argon atmosphere, and stirring reaction 16 is small
When.Reactant mixture is cooled to room temperature, water is added and carries out liquid separation.The solvent of the organic layer of gained is concentrated, by gained
Solid purified with silica gel column chromatography, obtain target product compound 10（2.6 g, 2 mmol）, 69% yield.
Mass spectrum MS [the ESI of compound 10+] m/z=1208.46 (theoretical value 1208.38).
The photoluminescence spectra of embodiment 3 detects
Compound 3 and compound 10 are dissolved in toluene solvant, concentration is about 10-4 Mol/L, in E1PLMM010 luminescence generated by lights
On spectrometer, using 300 nm as exciting light, the luminescence generated by light of the two is measured（PL）Spectrum main peak is shown in Table 1.
The heat decomposition temperature of embodiment 4 is tested
On BRUKER thermal decomposition testers, with 20 DEG C of heating rates per minute, within the temperature range of 25-600 DEG C, divide
Other test compound 3 corresponding heat decomposition temperature in weightlessness 5% with compound 10（T95）, its testing result see the table below 1.
Table 1
The preparation of OLED of the embodiment 5 containing compound 3
Set on the glass substrate of the x 1.1mm sizes of 25 x 75 thickness be 120 nm, be made up of tin indium oxide it is transparent
Electrode.Then oxygen plasma treatment is carried out to the glass substrate, after cleaning, the substrate is placed on vacuum as 10 × 10- 7On torr evaporated device；
First, the thick HT-1 of 70 nm are deposited as hole injection layer, 20 nm HT-2 is then deposited on it as hole
Transport layer；
Then, by the use of EM-1 as material of main part, by the use of the compound 3 as dopant material, with 97:3 weight ratios are deposited simultaneously, shape
Into 25 nm of thickness luminescent layer；
Then, 35 nm ET-1 is deposited:ET-2（Mass ratio is 1:1）As electron transfer layer, the thick ET-2 of 2 nm are then deposited
As electron injecting layer, the thick aluminium of 120nm is finally deposited as negative electrode.
Compound HT-1, HT-2, EM-1, ET-1 and the ET-2 being related in above-mentioned OLED preparation process are as follows respectively
The compound of shown structure：
The preparation of OLED of the embodiment 6 containing compound 10
Set on the glass substrate of the x 1.1mm sizes of 25 x 75 thickness be 120 nm, be made up of tin indium oxide it is transparent
Electrode.Then oxygen plasma treatment is carried out to the glass substrate, after cleaning, the substrate is placed on vacuum as 10 × 10- 7On torr evaporated device；
First, the thick HT-1 of 70 nm are deposited as hole injection layer, 20 nm HT-2 is then deposited on it as hole
Transport layer；
Then, by the use of EM-1 as luminescent material, by the use of the compound 10 as dopant material, with 97:3 weight ratios are deposited simultaneously,
Form 25 nm of thickness luminescent layer；
Then, 35 nm ET-1 is deposited:ET-2（Mass ratio is 1:1）As electron transfer layer, the thick ET-2 of 2 nm are then deposited
As electron injecting layer, the thick aluminium of 120nm is finally deposited as negative electrode.
Device prepares comparative example
In this comparative example, the making step of OLED is identical with the making step in embodiment 5, embodiment 6, unique difference
It is that dopant material therein has selected the control compounds C of Japanese Idemitsu Kosan companies, its structural formula is as follows：
Control compounds C
In order to characterize the performance of each OLED of the above, inventor has carried out correlated performance test：In various electric currents and voltage
Lower record electroluminescent spectrum, in addition, luminous output current-voltage characteristic is combined, can be defeated by light by using luminosity meter calibrating
Go out and be converted into photometric parameter, 2 are shown in Table under specific the performance test results：
Table 2
From upper table 2, the OLED prepared using compound of the present invention as dopant material, with comparative example phase
Than showing higher heat decomposition temperature, therefore heat endurance is good；Also, there is higher luminous efficiency and excitation（Performance
It is smaller for CIE y values）.
The specific embodiment of the present invention is described in detail above, but it is intended only as example, it is of the invention and unlimited
It is formed on particular embodiments described above.To those skilled in the art, it is any to the equivalent modifications that carry out of the present invention and
Substitute also all among scope of the invention.Therefore, the impartial conversion made without departing from the spirit and scope of the invention and
Modification, all should be contained within the scope of the invention.
Claims (10)
1. a kind of organic electroluminescent compounds, it is characterised in that the organic electroluminescent compounds have following formula（Ⅰ）Or
（Ⅱ）Or（Ⅲ）Shown structure：
Wherein, R1~R8It is each independently selected from：H, halogen, cyano group, C1 ~ C20 alkyl group, C1 ~ C20 halogenated alkane base, C3 ~
C20 cycloalkyl, C3 ~ C20 halogenated cycloalkyl, C1 ~ C20 alkoxy, C1 ~ C20 silylation, substituted or unsubstituted
Aryloxy group that cyclic carbon number is 6 ~ 30, the aryl that substituted or unsubstituted cyclic carbon number is 6 ~ 30 and substituted or unsubstituted
Cyclic carbon number be 6 ~ 30 heterocyclic arene base；
Wherein, m and n is each independently 0 or 1；When m and/or n is 1, L1And/or L2To be substituted or unsubstituted into ring carbon
The aryl that number is 6 ~ 30 or the heterocyclic arene base that substituted or unsubstituted cyclic carbon number is 6 ~ 30；
Wherein, X1~X2It is each independently selected from：O、S、S=O、O=S=O；
Wherein, X3~X4It is each independently selected from：C、N.
2. organic electroluminescent compounds according to claim 1, it is characterised in that R1~R8It is each independently selected from：H、
C1 ~ C20 alkyl group, C3 ~ C20 cycloalkyl, substituted or unsubstituted cyclic carbon number are 6 ~ 30 aryl and substituted
Or the heterocyclic arene base that unsubstituted cyclic carbon number is 6 ~ 30.
3. organic electroluminescent compounds according to claim 2, it is characterised in that R1~R8It is each independently selected from：H、
Methyl, ethyl, isopropyl, n-propyl, phenyl, naphthyl, p-methylphenyl, o-tolyl, a tolyl, to tert-butyl-phenyl, right
Trifluoromethyl.
4. organic electroluminescent compounds according to claim 1, it is characterised in that m and n is 0.
5. organic electroluminescent compounds according to claim 1, it is characterised in that m and/or n is 1, and L1And/or L2
The aryl for being 6 ~ 30 for unsubstituted cyclic carbon number.
6. organic electroluminescent compounds according to claim 1, it is characterised in that X1~X2It is O.
7. organic electroluminescent compounds according to claim 1, it is characterised in that X3~X4It is simultaneously C or N.
8. organic electroluminescent compounds according to claim 1, it is characterised in that the organic electroluminescent compounds
Selected from following any：
。
9. a kind of OLED luminescent layers dopant material, it is characterised in that it contains organic as any one of claim 1-8
Electroluminescent compounds.
10. a kind of OLED, it is characterised in that it contains the organic electroluminescent as any one of claim 1-8
Compound.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109963857A (en) * | 2016-11-25 | 2019-07-02 | 默克专利有限公司 | 2,8- diamino indeno [1,2-B] fluorene derivative and related compound condensed as double benzofurans of the material for organic electroluminescence device (OLED) |
| CN109963856A (en) * | 2016-11-25 | 2019-07-02 | 默克专利有限公司 | Indeno [1,2-B] fluorene derivative and related compound condensed as double benzofurans of the material for organic electroluminescence device (OLED) |
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| WO2018095888A1 (en) * | 2016-11-25 | 2018-05-31 | Merck Patent Gmbh | Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
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| CN105085334A (en) * | 2014-05-12 | 2015-11-25 | Sfc株式会社 | Electroluminescent compound and electroluminescent device comprising same |
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| CN109963857A (en) * | 2016-11-25 | 2019-07-02 | 默克专利有限公司 | 2,8- diamino indeno [1,2-B] fluorene derivative and related compound condensed as double benzofurans of the material for organic electroluminescence device (OLED) |
| CN109963856A (en) * | 2016-11-25 | 2019-07-02 | 默克专利有限公司 | Indeno [1,2-B] fluorene derivative and related compound condensed as double benzofurans of the material for organic electroluminescence device (OLED) |
| US11453680B2 (en) | 2016-11-25 | 2022-09-27 | Merck Patent Gmbh | Bisbenzofuran-fused indeno[1,2-B]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLED) |
| US11584753B2 (en) | 2016-11-25 | 2023-02-21 | Merck Patent Gmbh | Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (OLED) |
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Address after: 201506, No. nine, No. 1568, Jinshan Industrial Zone, Shanghai, Jinshan District Patentee after: Shanghai Hehui optoelectronic Co., Ltd Address before: 201506, No. nine, No. 1568, Jinshan Industrial Zone, Shanghai, Jinshan District Patentee before: EverDisplay Optronics (Shanghai) Ltd. |