CN106749094A - 42 (2` hydroxy phenyls) benzoxazole compounds and its preparation method and purposes containing substituted base - Google Patents
42 (2` hydroxy phenyls) benzoxazole compounds and its preparation method and purposes containing substituted base Download PDFInfo
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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Abstract
The present invention is related to and belongs to photoconductive organic semiconductor technical field, there is provided a kind of 42 (2' hydroxy phenyls) benzoxazole compounds and its preparation and use containing substituted base.Described 4 formulas of 2 (2' hydroxy phenyls) benzoxazole compounds containing substituted base are：Wherein X is S, O or NH, and Ar is the unit of conjugated structure containing aromatic hydrocarbons.The compound is prepared by suzuki reaction with the polycyclic aromatic hydrocarbon compounds with bromine by 2 (2'4 bromophenols) benzothiazoles.The compound invented herein has the four-level transition photoluminescent property of excited state intramolecular proton transfer compound, can be as luminescent material, in white organic diode component.Compound of the invention has：The advantages of big stoke shift, good luminous quantum efficiency, preparation is simply, synthetic yield is high.
Description
Technical field
The invention belongs to photoconductive organic semiconductor technical field, and in particular to a kind of 4 2- (the 2'- hydroxyls containing substituted base
Base phenyl) benzoxazole compound and its preparation and application.
Background technology
1987, the C.W.Tang in the U.S. et al. inventions were made the organic light-emitting diodes of multilayer architecture with vacuum vapour deposition
Pipe (OLED) so that the research of organic electroluminescence device is paid much attention to by scientists from all over the world.The development of OLED technology is right
Photoelectric display field generates earth-shaking change.Nowadays the maturation of the development of material science and theoretical technique is to new OLED
Development play vital effect so that exploration of the researcher of Material Field to luminescent material generates greatly emerging
Interest.Have that efficiency high, brightness are high, low in energy consumption, visual angle is wide due to white organic LED (WOLED), fast response time, master
Dynamic luminous, ultra-thin and ultra-light and can the excellent properties such as flexibility, and have broad prospect of application in display and lighting field, learned
The extensive attention of person and industry and turn into study hotspot.
1994, professor Kido of Japanese chevron university waited and is prepared for first WOLED device in the world first, although working as
When device maximum power efficiency there was only 0.83lm/W, high-high brightness only has 3400cd/M2But, still in organic electroluminescent
Devices field realizes breakthrough progress.
2003, WOLED device efficiencies reached 15lm/W and have exceeded incandescent lamp first.2006, the U.S. Holy Land was sub-
The Nobuhiro Ide research groups of brother university prepare the stack multilayer light-emitting junction of Color tunable control using full phosphor material
The WOLED of structure, its device efficiency has reached 62.8lm/W.2008, the James Esler researchs of San Diego, USA university were small
Group prepares the WOLED that maximum power efficiency is 100 lm/W multi-luminescent layer structures, and its operating voltage is 3.6V, external quantum efficiency
Reach 20%.
The efficiency of multi-luminescent layer WOLED is generally higher, but structure and process conditions are relative complex, voltage is higher, cause
Cost is also of a relatively high, there is hetero-junctions between each luminescent layer, and stable color coordinate is typically poor.How reasonably to control
Exciton generating region, exciton recombination region, energy transfer and exciton diffusion are to obtain high performance guarantee between each luminescent layer.
At present, in WOLED fields, a kind of device efficiency of exploitation is high, process is simple, and low cost, the individual layer of good stability is white
Optical device is to realize the commercialized key of white organic LED.
The content of the invention
For device preparation technology present in current white organic LED it is complicated, cost of manufacture is higher, repeat
Property the technical problem such as poor, the invention provides 2- (the 2'- hydroxyl containing substituted base of a kind of new organic fluorescence materials, i.e., 4
Phenyl) benzoxazole compound, and its preparation method and application.Described organic fluorescence materials are a series of with excited state molecule endoplasm
2- (2'- hydroxy phenyls) benzothiazole of the four-level transition property of sub- transfer compounds, and connect various conjugated structures containing aromatic hydrocarbons
The new material of unit.This kind of material has fluorescence quantum yield high, and stoke shift is big, and synthesis is simple, the advantages of yield is high.It is logical
Cross and mix commercialized blue light material composition binary complementary colours, can be with the single layer white light device of preparation process is simple.The present invention is adopted
Technical scheme is as follows.
The invention provides a kind of 4 2- (2'- hydroxy phenyls) benzoxazole compounds containing substituted base.
4 of the present invention 2- (2'- hydroxy phenyls) benzoxazole compounds containing substituted base, its general structure is：
In formula：X is S, O or NH, and Ar is the unit of conjugated structure containing aromatic hydrocarbons.
The unit of conjugated structure containing aromatic hydrocarbons is selected from the one kind in following substituent structure：
The present invention also provides above-mentioned 4 preparation methods of 2- (2'- hydroxy phenyls) benzoxazole compound containing substituted base.
The 4 of the present invention preparation methods of 2- (2'- hydroxy phenyls) benzoxazole compound containing substituted base, its bag
Include following steps：
(1) boration of the compound of conjugated structure containing aromatic hydrocarbons：Under nitrogen protection, aryl bromide is dissolved in dry organic molten
Agent, temperature adds n-BuLi under the conditions of being less than -40 DEG C, after stirring 2 to 4 hours, add boronic acid compounds, boration to heat up
Reacted 15-20 hours after to normal temperature.After reaction terminates, organic phase is extracted, organic phase is merged into drying, obtain product.
(2) by product and 2- (2'-4- bromophenols) benzothiazole of step (1), palladium catalyst is dissolved in organic solvent, Ran Houjia
Enter strong alkali aqueous solution, the lower reaction of nitrogen protection.After reaction terminates, organic phase is extracted, merge organic phase and concentrate, separating-purifying
Afterwards, end-product is obtained, product as of the invention.
In above-mentioned steps (1), low-temp reaction can be used dry ice acetone bath cooling；The boronic acid compounds are positive three fourth of boric acid
Ester；Organic phase is extracted using water and dichloromethane；The organic solvent is tetrahydrofuran.
In above-mentioned steps (2), the palladium catalyst is tetrakis triphenylphosphine palladium, double (dibenzalacetone) palladiums, 1,1- are double
(diphenyl phosphine) ferrocene dichloro, highly basic is one or more in potassium carbonate, potassium chloride, potassium fluoride, and the organic solvent is
The volume ratio of tetrahydrofuran and toluene is 1:1 mixed solvent.Reaction temperature is 80-120 DEG C, and the reaction time is 24-60 hours.
The formula of described 2- (2'-4- bromophenols) benzoxazole compound is：
Wherein, X is S, O or NH.
In above-mentioned preparation method, according to the molar ratio, in step (1), the ratio of aryl bromide and n-BuLi is 1：0.9~
1.5, preferably 1：1.2；In step (2), the ratio of the boration aryl bromide and 2- (2'-4- bromophenols) benzothiazole is 1：
0.5~1.5, preferably 1:1
The adding proportion of the aryl bromide and organic solvent is 1 mole：2~8 liters.It is preferably in a proportion of 1 mole：4~6
Rise.
It is still another object of the present invention to provide based on 4 2- (2'- hydroxy phenyls) benzothiazole chemical combination containing substituted base
Thing is used to prepare the purposes of white organic LED.
4 of the present invention 2- (2'- hydroxy phenyls) benzoxazole compounds containing substituted base can be as luminous material
Material, in white organic diode component.Binary complementary colours is constituted by mixing commercialized blue light material, work can be prepared
The simple single layer white light device of skill.
The present invention has the advantages that：1st, 4 of the invention 2- (2'- hydroxy phenyls) benzothiazoles containing substituted base
Compound has fluorescence quantum yield high, and stoke shift is big；2nd, the preparation method synthesis of above-claimed cpd is simple, and yield is high,
Beneficial to expanding the scale of production；3rd, above-claimed cpd can be as luminescent material, in white organic diode component.
Brief description of the drawings
The carbon spectrogram of the compound of Fig. 1 embodiment of the present invention 2；
The carbon spectrogram of the compound of Fig. 2 embodiment of the present invention 3；
The fluorescent absorption of the compound of Fig. 3 embodiment of the present invention 2-transmitting figure；
The fluorescent absorption of the compound of Fig. 4 embodiment of the present invention 3-transmitting figure；
The redox curve of the compound of Fig. 5 embodiment of the present invention 2.
Specific embodiment
In order to be best understood from the content of patent of the present invention, skill of the invention is further illustrated below by specific example
Art scheme.But these embodiments are not intended to limit the present invention.
Material 2- (2'-4- bromophenols) benzothiazoles by suzuki reaction connect various aromatic hydrocarbons conjugated structure units to electricity
Subbase group, the material has following formula：
In formula：X is S, O or NH.
Embodiment 1,
First, the preparation of 2- (2'-4- bromophenols) benzothiazole：
Take diaminophenol (4.4g, 20mmol, 1equiv) and p-aminobenzoic acid (2.5g, 20mmol, 1equiv) is added
In 130ml polyphosphoric acids, in N2Environment in be heated to 168 DEG C, and flow back 6 hours.After question response is complete, by product after cooling
It is dissolved in 100ml mixture of ice and water, the NaOH aqueous solution for being added thereto to saturation is neutralized.Treat pH value be adjusted to 6 or so change plus
NaHCO3, it is stirring while adding, to there is no CO2Bubble is produced.By the solution left standstill after neutralization after suction filtration after solution clarification.Taking out
Leach the solid for coming and add saturation NaHCO3The aqueous solution is extracted with ethyl acetate three times, merges organic layer, uses anhydrous Na2SO4Dry
Green product 5g is obtained after revolving, yield is 83%.(in following embodiments, the preparation side of 2- (2'-4- bromophenols) benzothiazole
Method is all identical with this, repeats no more).
Secondly, the preparation of 2- (2'- benzothiazoles) -4- (9'- is luxuriant and rich with fragrance) phenol
(1) boration of the compound of conjugated structure containing aromatic hydrocarbons：Under nitrogen protection, 9- bromo phenanthrenes are dissolved in dry tetrahydrochysene furan
Mutter, be placed in cooling in dry ice acetone bath (- 78 DEG C), n-BuLi, the addition ratio of 9- bromo phenanthrenes and n-BuLi are added under low temperature
Example is 1：After 0.9 stirring 2 hours, add the positive tri butyl ester of boric acid, boration to continue to react 0.5 hour, remove dry ice acetone bath,
Reacted 15 hours after being warmed up to normal temperature.After reaction terminates, reaction is quenched under ice-water bath, then being extracted with water and dichloromethane has
Machine phase, merges organic phase drying and is spin-dried for, obtains product.
(2) take 9- boric acid phenanthrene (0.18g, 0.75mmol, 1 equivalent) and 2- (2'-4- bromophenols) benzothiazole (0.12g,
0.38mmol, 0.5 equivalent) the mixing volume ratio that is dissolved in 20ml tetrahydrofurans and toluene is 1:In 1 mixed solution.Add catalysis
Agent Pd (pph3)4.Lucifuge leads to nitrogen, and it is the potassium carbonate of 2mol/L and the aqueous solution of potassium fluoride to add 10ml concentration.At 80 DEG C
Under the conditions of react 24 hours.After reaction terminates, organic phase is extracted, merge organic phase and concentrate, carried out by the method for chromatographic column
Separating-purifying, obtains yellow powder end-product.
Embodiment 2,
The preparation of 2- (2'- benzothiazoles) -4- (9'- is luxuriant and rich with fragrance) phenol
(1) boration of the compound of conjugated structure containing aromatic hydrocarbons：Under nitrogen protection, 9- bromo phenanthrenes are dissolved in dry tetrahydrochysene furan
Mutter, be placed in be cooled in dry ice acetone bath under -78 DEG C, low temperature and add n-BuLi, the addition ratio of 9- bromo phenanthrenes and n-BuLi
Example is 1：1.2, after stirring 3 hours, add the positive tri butyl ester of boric acid, boration to continue to react 0.5 hour, dry ice acetone bath is removed,
Reacted 18 hours after being warmed up to normal temperature.After reaction terminates, reaction is quenched under ice-water bath, then being extracted with water and dichloromethane has
Machine phase, merges organic phase drying and is spin-dried for, obtains product.
(2) take 9- boric acid phenanthrene (0.18g, 0.75mmol, 1 equivalent) and 2- (2'-4- bromophenols) benzothiazole (0.24g,
0.75mmol, 1 equivalent) the mixing volume ratio that is dissolved in 20ml tetrahydrofurans and toluene is 1:In 1 mixed solution.Add catalyst
Pd(pph3)4.Lucifuge leads to nitrogen, and it is the potassium carbonate of 2mol/L and the aqueous solution of potassium fluoride to add 10ml concentration.In 90 DEG C of bar
Reacted 48 hours under part.After reaction terminates, organic phase is extracted, merge organic phase and concentrate, divided by the method for chromatographic column
From purification, yellow powder end-product 0.31g is obtained, yield is 82%.
Nuclear magnetic resonance and redox curve detection are carried out to end-product, respectively as shown in Figure 1 and Figure 5
Embodiment 3,
The preparation of 2- (2'- benzothiazoles) -4- (1'- pyrenes) phenol
Change the 9- boric acid phenanthrene in embodiment 2 into 1- boric acid pyrenes, concretely comprise the following steps：
(1) boration of the compound of conjugated structure containing aromatic hydrocarbons：Under nitrogen protection, 1- bromos pyrene is dissolved in dry tetrahydrochysene furan
Mutter, be placed in be cooled in dry ice acetone bath under -78 DEG C, low temperature and add n-BuLi, the addition ratio of 1- bromos pyrene and n-BuLi
Example is 1：1.2, after stirring 3 hours, add the positive tri butyl ester of boric acid, boration to continue to react 0.5 hour, dry ice acetone bath is removed,
Reacted 18 hours after being warmed up to normal temperature.After reaction terminates, reaction is quenched under ice-water bath, then being extracted with water and dichloromethane has
Machine phase, merges organic phase drying and is spin-dried for, obtains product.
(2) take 9- boric acid pyrene (0.6g, 2.2mol, 1 equivalent) and 2- (2'-4- bromophenols) benzothiazole (0.7g,
2.2mmol, 1 equivalent) the mixing volume ratio that is dissolved in 30ml tetrahydrofurans and toluene is 1:In 1 mixed solution.Add catalyst
Pd(pph3)4.Lucifuge leads to nitrogen, and it is the potassium carbonate of 2mol/L and the aqueous solution of potassium fluoride to add 10ml concentration.In 90 DEG C of bar
Reacted 48 hours under part.After reaction terminates, organic phase is extracted, merge organic phase and concentrate, divided by the method for chromatographic column
From purification, yellow powder end-product 0.86g is obtained, yield is 73%.
Magnetic resonance detection is carried out to end-product, as shown in Figure 2.
Embodiment 4,
The preparation of 2- (2'- benzothiazoles) -4- (1'- pyrenes) phenol
(1) boration of the compound of conjugated structure containing aromatic hydrocarbons：Under nitrogen protection, 1- bromos pyrene is dissolved in dry tetrahydrochysene furan
Mutter, be placed in be cooled in dry ice acetone bath under -78 DEG C, low temperature and add n-BuLi, the addition ratio of 1- bromos pyrene and n-BuLi
Example is 1：1.5, after stirring 4 hours, add the positive tri butyl ester of boric acid, boration to continue to react 0.5 hour, dry ice acetone bath is removed,
Reacted 20 hours after being warmed up to normal temperature.After reaction terminates, reaction is quenched under ice-water bath, then being extracted with water and dichloromethane has
Machine phase, merges organic phase drying and is spin-dried for, obtains product.
(2) take 9- boric acid pyrene (0.6g, 2.2mol, 1 equivalent) and 2- (2'-4- bromophenols) benzothiazole (0.36g,
3.3mmol, 1.5 equivalents) the mixing volume ratio that is dissolved in 30ml tetrahydrofurans and toluene is 1:In 1 mixed solution.Add catalysis
Agent Pd (pph3)4.Lucifuge leads to nitrogen, and it is the potassium carbonate of 2mol/L and the aqueous solution of potassium fluoride to add 10ml concentration.At 120 DEG C
Under conditions of react 60 hours.After reaction terminates, organic phase is extracted, merge organic phase and concentrate, entered by the method for chromatographic column
Row separating-purifying, obtains yellow powder end-product.
Embodiment 5,
The preparation of 3- (2'- benzothiazoles) -4'- (1,2,2- triphenylethylenes) -4'- [1,1'- biphenyl]
(1) boration of the compound of conjugated structure containing aromatic hydrocarbons：Under nitrogen protection, bromo tetraphenyl ethylene is dissolved in dry four
Hydrogen furans, is placed in be cooled in dry ice acetone bath under -78 DEG C, low temperature and adds n-BuLi, bromo tetraphenyl ethylene and n-BuLi
Adding proportion be 1：1.2, after stirring 3 hours, add the positive tri butyl ester of boric acid, boration to continue to react 0.5 hour, remove dry
Ice acetone bath, reacts 18 hours after being warmed up to normal temperature.After reaction terminates, reaction is quenched under ice-water bath, then with water and dichloro
Methane extracts organic phase, and organic phase is merged into drying is spin-dried for, and obtains product.
(2) take boric acid tetraphenyl ethylene (0.5g, 1.9mol, 1 equivalent) and 2- (2'-4- bromophenols) benzothiazole (0.65g,
1.9mmol, 1 equivalent) the mixing volume ratio that is dissolved in 40ml tetrahydrofurans and toluene is 1:In 1 mixed solution.Add catalyst
Pd(pph3)4.Lucifuge leads to nitrogen, and it is the potassium carbonate of 2mol/L and the aqueous solution of potassium fluoride to add 10ml concentration.In 90 DEG C of bar
Reacted 48 hours under part.After reaction terminates, organic phase is extracted, merge organic phase and concentrate, divided by the method for chromatographic column
From purification, pale yellow powder shape end-product is obtained.
Embodiment 6,
The present embodiment is the measure of the compound spectra prepared to embodiment 2 and embodiment 3.
The compound of embodiment 2 and embodiment 3 is made into 1 μM of standard of tetrahydrofuran solution.It is purple using Shimadzu -3150
Outer visible spectrophotometer and RF-520XPC XRFs carry out the measure of absorption spectrum and emission spectrum.Photoluminescence spectra is
Go out what is measured in the absorption maximum of UV absorption.As shown in Figure 3 and Figure 4, as seen from the figure, the absorption of two compounds and fluorescence weight
Not there is overlap even in folded scope very little, illustrate that the two materials have the advantages that stoke shift is big.
Embodiment 6,
The present embodiment is the measure of the compound electrochemistry prepared to embodiment 2 and embodiment 3.
Electrochemistry cyclic voltammetric (CV) experiment is in B.V.AUTOLABpotentiostat volt-amperes point of an Eco Chemie
Completed in analyzer, using three-electrode system, including platinum carbon electrode, Ag/Ag+For reference electrode, platinum filament are to electrode.Aoxidized
, used as solvent, reduction process is using tetrahydrofuran as solvent, hexafluoro phosphorus TBuA (Bu for Cheng Caiyong dichloromethane4N+PF6 -)
Used as supporting electrolyte, concentration is 0.1M.All electrochemistry experiments are all carried out in nitrogen atmosphere at normal temperatures, voltage scanning
Speed 0.1V/S.Using ferrocene (FOC) as benchmark, material can be calculated by the beginning voltage for measuring oxidation and reduction process
The HOMO and lumo energy of material.
The position of the redox peaks of material is can be seen that from Electrochemical results Fig. 5, then by formula：
HOMO=- [EOX–EFe/Fe++4.8]
LUMO=- [ERE–EFe/Fe++4.8]
The HOMO and lumo energy that calculating can obtain the material of embodiment 2 are respectively -5.44eV and -3.40eV.Embodiment 3
The HOMO and lumo energy of material are respectively -5.26eV and -3.44eV.
Claims (10)
1. a kind of 4 2- (2'- hydroxy phenyls) benzoxazole compounds containing substituted base, it is characterised in that the compound formula
For：
In formula：X is S, O or NH, and Ar is the unit of conjugated structure containing aromatic hydrocarbons, and the unit of conjugated structure containing aromatic hydrocarbons is selected from following substitution
One kind in based structures：
2. a kind of 4 as claimed in claim 1 containing substituted base 2- (2'- hydroxy phenyls) benzoxazole compound preparation side
Method, it is characterised in that the preparation method is concretely comprised the following steps：
(1) preparation of the unit of conjugated structure containing aromatic hydrocarbons：Under nitrogen protection, aryl bromide is dissolved in dry organic solvent, temperature
Degree adds n-BuLi under the conditions of being less than -40 DEG C, after stirring 2 to 4 hours, boration, and continuation reaction 15 is arrived after being warming up to normal temperature
20 hours.After reaction terminates, organic phase is extracted, organic phase is merged into drying is spin-dried for, and obtains product；
(2) by product and 2- (2'-4- bromophenols) benzothiazole of step (1), palladium catalyst is dissolved in organic solvent, is subsequently adding one
Quantitative strong alkali aqueous solution, the lower reaction of nitrogen protection, after reaction terminates, extracts organic phase, merges organic phase and concentrates, and separation is carried
After pure, end-product is obtained.
3. preparation method according to claim 2, it is characterised in that：According to the molar ratio, in step (1), aryl bromide and
The ratio of n-BuLi is 1：0.9~1.5；In step (2), polycyclic aromatic hydrocarbon and 2- (2'-4- bromophenols) benzo of the bromo
The ratio of azoles is 1：0.5~1.5.
4. preparation method according to claim 3, it is characterised in that：According to the molar ratio, in step (1), aryl bromide and
The ratio of n-BuLi is 1：1.2；In step (2), the ratio of the aryl bromide and 2- (2'-4- bromophenols) benzothiazole is 1：
1。
5. the preparation method according to claim 2,3 or 4, it is characterised in that：Described 2- (2'-4- bromophenols) benzothiazole
The formula of compound is：
Wherein X is S, O or NH.
6. preparation method according to claim 2, it is characterised in that：Reaction dissolvent in step (1) is tetrahydrofuran；Step
Suddenly the reaction dissolvent in (2) is that the volume ratio of tetrahydrofuran and toluene is 1:1 mixed solvent.
7. preparation method according to claim 2, it is characterised in that：The adding proportion of the aryl bromide and organic solvent
It is 1 mole：2~8 liters.
8. preparation method according to claim 7, it is characterised in that：The adding proportion of the aryl bromide and organic solvent
It is 1 mole：4~6 liters.
9. a kind of purposes of the arene compounds of 2- according to claim 1 (2'- hydroxy phenyls) benzothiazole, its feature
It is：Described compound can be used in white light organic diode device.
10. purposes according to claim 9, it is characterized in that：Described compound mixing blue light material composition binary is complementary
Color, can be with the single layer white light device of preparation process is simple.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN113480493A (en) * | 2021-05-20 | 2021-10-08 | 南京邮电大学 | Organic yellow fluorescence excited state proton transfer material and OLED device thereof |
| CN113563325A (en) * | 2021-05-24 | 2021-10-29 | 南京邮电大学 | ESIPT luminescent material with high exciton utilization rate and preparation method and application thereof |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102050798A (en) * | 2010-12-07 | 2011-05-11 | 吉林大学 | 2-(2'-hydroxylphenyl)-benzothiazole derivative luminescent materials |
-
2016
- 2016-12-09 CN CN201611128271.0A patent/CN106749094A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102050798A (en) * | 2010-12-07 | 2011-05-11 | 吉林大学 | 2-(2'-hydroxylphenyl)-benzothiazole derivative luminescent materials |
Non-Patent Citations (3)
| Title |
|---|
| DANDAN YAO，等: "Hydroxyphenyl-benzothiazole based full color organic emitting materials generated by facile molecular modification", 《JOURNAL OF MATERIALS CHEMISTRY》 * |
| PAULA DE ECHEGARAY，等: "Synthesis of Perylene Imide Diones as Platforms for the Development of Pyrazine Based Organic Semiconductors", 《J.ORG.CHEM.》 * |
| YUJI INATSU，等: "Photoinduced Hydrogen Atom Transfer in 2-(2"-Hydroxyphenyl)-benzimidazole Substituted with Anthracene", 《BULL.CHEM.SOC.JPN.》 * |
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