CN108358908A - A kind of asymmetry thermal activation delayed fluorescence red light material and the preparation method and application thereof - Google Patents
A kind of asymmetry thermal activation delayed fluorescence red light material and the preparation method and application thereof Download PDFInfo
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The invention discloses a kind of asymmetric thermal activation delayed fluorescence red light materials and the preparation method and application thereof.The asymmetry thermal activation delayed fluorescence red light material has general structure as follows, Ar in formula1And Ar2It is donor groups, and Ar1≠Ar2.The present invention has selected donor appropriate and acceptor molecule to synthesize, and energy gap is smaller, can emit feux rouges, dark red light；Material becomes thermal activation delayed fluorescence material, 100% internal quantum efficiency may be implemented, improve the device efficiency of material since asymmetry connection makes HOMO and LUMO tracks significantly detach；Materials synthesis step is short, and yield is high, at low cost.
Description
Technical field
The invention belongs to organic photoelectrical material technical fields, and in particular to a kind of asymmetry thermal activation delayed fluorescence feux rouges material
Material and the preparation method and application thereof.
Background technology
Organic electroluminescent phenomenon can trace back to 1963, and Pope seminars and Visco seminars find in micron thickness
Anthracene single crystal apply and be observed that blue emission not less than the DC voltage of 400W.Until 1987, Kodak was sent out
Sandwich type organic bilayer film electroluminescent device is illustrated, using 8-hydroxyquinoline aluminium as emitting layer material, in little Yu 10V
The lower device light emission luminance of voltage driving reaches 1000cd/m2, efficiency 1.51m/W, to evoke electroluminescent organic material
With the research boom of device.
In recent years, it is caused extensively based on a kind of luminous organic material of new principle " thermal activities delayed fluorescence " (TADF) material
General concern, this material by thermal excitation by triplet exciton is counter be between pass through and be converted into singlet excitons and shine, it is theoretical in amount
Sub- efficiency is expected to develop into low cost and high performance OLED material in application aspect up to 100%.Thermal activities delayed fluorescence
Material is in green light, and the field breakthrough of blue light is very big, and in contrast, feux rouges stagnates substantially.To find out its cause, mainly having following three
Point：（1）Suitable donor and acceptor molecule are less；（2）When energy gap is smaller, since nonradiative transition enhances, quantum efficiency will
It can reduce；（3）When energy gap is smaller, since the enhancing of conjugation can also be such that quantum efficiency reduces.With countries in the world science machine
Thermal activities delayed fluorescence red light material and device research go deep into structure and major company, it is believed that these problems can be solved gradually
Certainly, application of the thermal activities delayed fluorescence red light material in terms of display and illumination also has vast market prospect.Wherein, it develops
The material of new and effective stabilization becomes key.
Invention content
For current thermal activation delayed fluorescence red light material problems faced, a kind of asymmetric thermal activation of present invention offer is prolonged
Slow fluorescence red light material and the preparation method and application thereof.The material has preferable dissolubility and interface performance, is suitable for solution
Processing and inkjet printing.
It is to work as Ar as improved1General structure for carbazole, the fluorescence red light material is
The preparation method of above-mentioned asymmetry thermal activation delayed fluorescence red light material, includes the following steps：Step 1, by benzo
Thiadiazoles, carbazole, potassium carbonate, copper powder are placed in bottle, and sealing vacuumizes, and drum argon gas reenters nitrobenzene dissolving, add until vacuum
After heat reflux, waits for after reaction, being cooled to room temperature, and reaction solution vacuum distillation removes nitrobenzene, with dichloromethane and water-soluble
Liquid extracts, and collects organic phase and is dried with anhydrous sodium sulfate, is concentrated to give the first crude product；Step 2, the first crude product of purifying obtains list
Sideband carbazole product；Step 3, by single-side belt carbazole product, Ar2, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine set
In bottle, sealing vacuumizes, and drum argon gas is added toluene dissolving, is heated to reflux, wait for after reaction until basic vacuum, cooling
To room temperature, reaction solution dichloromethane and aqueous solution extraction collect organic phase, are used in combination anhydrous sodium sulfate to dry, are concentrated to give second
Crude product；Step 4, the second crude product of purifying is to get fluorescence red light material.
It is diazosulfide, carbazole in step 1 as improved（Ar1）, potassium carbonate, copper powder molar ratio be 1:1:4:
0.4, reflux temperature is 175-180 DEG C, and return time is for 24 hours；It is purified by step 2 using petroleum ether and dichloromethane as exhibition
Agent is opened, is completed by silica gel column chromatography, the volume ratio of the dichloromethane and petroleum ether is 1：4, single-side belt carbazole produces in step 3
Object, Ar2, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine molar ratio be 1:1:0.04:1:0.12, reflux temperature is
115-124 DEG C, return time is purified by for 24 hours, in step 4 using petroleum ether and dichloromethane as solvent, passes through silica gel
Chromatographic column is completed, and the volume ratio of the dichloromethane and petroleum ether is 1：3.
It is to work as Ar as improved1For non-carbazole when, the general structure of the fluorescence red light material is
The preparation method of above-mentioned asymmetry thermal activation delayed fluorescence red light material, includes the following steps：Step 1, by benzo
Thiadiazoles, Ar1, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine be placed in bottle, seal, vacuumize, drum argon gas until
Basic vacuum is added toluene dissolving, is heated to reflux, after reaction, is cooled to room temperature, reaction solution dichloromethane and aqueous solution
Extraction, organic phase are collected and are dried with anhydrous sodium sulfate, and the first crude product is concentrated to give；Step 2, the first crude product is purified, list is obtained
Side product；Step 3, by unilateral product, Ar2, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine be placed in bottle, seal,
It vacuumizes, drum argon gas adds toluene dissolving, be heated to reflux, after reaction, be cooled to room temperature, react until basic vacuum
Liquid dichloromethane and aqueous solution extraction, organic phase are collected and are dried with anhydrous sodium sulfate, and the second crude product is concentrated to give；Step 4,
The second crude product is purified to get fluorescence red light material.
It is diazosulfide, Ar in step 1 as improved1, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine
Molar ratio 1:1:0.04:1:0.12, reflux temperature is 115-124 DEG C, and return time is for 24 hours；It is purified by step 2 and utilizes stone
Oily ether and dichloromethane are completed as solvent by silica gel column chromatography, and the volume ratio of the dichloromethane and petroleum ether is 1：
3, unilateral product, Ar in step 32, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine molar ratio be 1:1:0.04:1:
0.12, reflux temperature is 115-124 DEG C, return time be purified by for 24 hours, in step 4 using petroleum ether and dichloromethane as
Solvent is completed by silica gel column chromatography, and the volume ratio of the dichloromethane and petroleum ether is 1：3.
Application of the above-mentioned asymmetry thermal activation delayed fluorescence red light material in organic electronic display field.
Advantageous effect：
Compared with prior art, fluorescence red light material of the present invention by thermal excitation by triplet exciton is counter be between pass through and be converted into list
Weight state excitonic luminescence, resulting materials have good dissolubility energy and an interface performance, theoretical internal quantum efficiency up to 100%, from
And there is higher fluorescence quantum yield, the luminous efficiency of device is improved, redder saturation feux rouges is become.Made of this material
Luminescent device performance is stablized, and meets the requirement of full-color display, has huge development potentiality and foreground in organic electronic display field.
Description of the drawings
Fig. 1 is compound DPABTDMAC's1H NMR spectras；
Fig. 2 is the enlarged drawing of part in Fig. 1 frames；
Fig. 3 is compound DPABTDMAC's13C NMR spectras；
The solution that Fig. 4 is compound DPABTDMAC absorbs figure；
Fig. 5 is compound CzBTDPA's1H NMR spectras；
Fig. 6 is compound CzBTDPA's13C NMR spectras；
Fig. 7 is the high resolution mass spectrum figure of compound CzBTDPA；
Fig. 8 is fluorescence emission spectrum of tri- compounds of CzBTDPA, CzBTDMAC, CzBTPHt in dichloromethane solution.
Specific implementation mode
In order to better understand the content of the present invention, below by specific example, the invention will be further described, but
The implementation and protection domain of the present invention is without being limited thereto.
The preparation of 1 DPABTDMAC of embodiment
Take 250 mL bottle with two necks, accurately claim to obtain 1.76 g 4,7- dibromos benzo [c] -1,2,5- thiadiazoles, 2.23 g diphenylamines,
54 mg palladiums, 1.27 g sodium tert-butoxides and 145 mg tetrafluoro boric acid tri-tert-butylphosphines are placed in bottle, and sealing vacuumizes,
Drum argon gas is until basic vacuum.80 mL toluene, 115 DEG C of 24 h of reflux are added with syringe.Reaction solution is with the two of 3 × 100 mL
Chloromethanes and aqueous solution extraction, organic phase are collected and are dried with anhydrous sodium sulfate, crude product are concentrated to give, through petroleum ether and dichloromethane
Alkane solvent（3:1）Silica gel column chromatography column separating purification obtains the unilateral products of 1.2 g, yield 85%.Chemical equation is such as
Under：
100 mL bottle with two necks are taken, 1 g DPA-BTZ-Br, 0.824 g DMAC, 25 mg palladiums, 0.379 g are accurately claimed to obtain
Sodium tert-butoxide and 93 mg tetrafluoro boric acid tri-tert-butylphosphines are placed in bottle, and sealing vacuumizes, and drum argon gas is until basic vacuum.With
40 mL toluene, 124 DEG C of 24 h of reflux are added in syringe.The dichloromethane and aqueous solution extraction of 3 × 50 mL of reaction solution, has
Machine is mutually collected and is dried with anhydrous sodium sulfate, and crude product is concentrated to give, through petroleum ether and dichloromethane solvent（3:1）Silica gel column chromatography
Column separating purification obtains 1 g red products, yield 80%.1H NMR (400 MHz, CDCl3 , ppm): δ =7.574
（D, 1H）,7.505（T, 2H）, 7.345（M, 4H）,7.278（D, 1H）, 7.167（T, 6H）, 6.958（M, 4H）, 6.284 (d,
2H), 1.770（S, 6H）. 13C NMR (100 MHz, CDCl3 , ppm): δ =154.463,151.994,147.592,
140.599,140.530,133.468,130.679,129.424,127.364,126.399,125.329,124.786,
124.060,121.201,121.054,113.716,36.155,30.955.1 H NMR、13CNMR, spectrogram are respectively such as Fig. 1-3 institutes
Show, analysis is known for target product.Chemical equation is as follows：
The preparation of 2 CzBTDPA of embodiment
250 mL bottle with two necks are taken, 2 g 4,7- dibromos benzo [c] -1,2,5- thiadiazoles, 1.15 g carbazoles, 3.79 are accurately claimed to obtain
G potassium carbonate, 0.175 g copper powders are placed in bottle, and sealing vacuumizes, and drum argon gas is until basic vacuum.It is added 80 with syringe
ML nitrobenzenes, 175 DEG C of 24 h of reflux.Reaction solution first passes through vacuum distillation and removes nitrobenzene, then the dichloromethane with 3 × 100 mL
Alkane and aqueous solution extraction, organic phase are collected and are dried with anhydrous sodium sulfate, crude product are concentrated to give, through petroleum ether and dichloromethane exhibition
Open agent（4:1）Silica gel column chromatography column separating purification obtains 1.1 g single-side belt carbazole products, yield 60%.Chemical equation
It is as follows：
Take 100 mL bottle with two necks, accurately claim 0.2 g CZ-BTZ-Br, 0.0896 g diphenylamines, 4.75 mg palladiums,
0.051 g sodium tert-butoxides and 18.45 mg tetrafluoro boric acid tri-tert-butylphosphines are placed in bottle, sealing, vacuumize, drum argon gas until
Basic vacuum.40 mL toluene, 124 DEG C of 24 h of reflux are added with syringe.The dichloromethane and water of 3 × 50 mL of reaction solution
Solution extracts, and organic phase is collected and dried with anhydrous sodium sulfate, crude product is concentrated to give, through petroleum ether and dichloromethane solvent
（3:1）Silica gel column chromatography column separating purification obtains 0.2 g red products, yield 80%.1H NMR (400 MHz, CDCl3 ,
ppm): δ =8.194（D, 2H）, 7.705（D, 1H）,7.369（M, 9H）, 7.197（M, 8H）. 13C NMR (100MHz,
CDCl3,ppm):δ =153.001,151.613,147.622,141.313,140.081,129.442,128.938,
125.864,124.701,124.394,124.035,121.730,123.735,120.455,120.271,110.317.1 H
NMR、13As illustrated in figs. 5-7, analysis is known for target product for CNMR and high resolution mass spectrum figure difference.Chemical equation is as follows：
In addition, the present invention is not limited to the above embodiments, as long as in without departing from the scope of the present invention, various modes can be taken
Implement the present invention.
Claims (9)
1. a kind of asymmetry thermal activation delayed fluorescence red light material, which is characterized in that the fluorescence red light material has following institute
The general structure shown, Ar in formula1And Ar2It is donor groups, and Ar1≠Ar2。
2. a kind of asymmetric thermal activation delayed fluorescence red light material according to claim 1, which is characterized in that Ar1And Ar2
For
Diphenylamines, carbazole, 9,9-dimethylacridan、
PhenoxazineOr phenthazineIn any two.
3. a kind of asymmetric thermal activation delayed fluorescence red light material according to claim 2, which is characterized in that work as Ar1For click
The general structure of azoles, the fluorescence red light material is
、(、
Or。
4. based on a kind of preparation method of asymmetric thermal activation delayed fluorescence red light material described in claim 3, feature exists
In including the following steps：Step 1, diazosulfide, carbazole, potassium carbonate, copper powder are placed in bottle, seal, vacuumizes, drum argon
Gas reenters nitrobenzene dissolving, is heated to reflux, waits for after reaction, being cooled to room temperature until vacuum, and reaction solution vacuum distillation removes
It after removing nitrobenzene, with dichloromethane and aqueous solution extraction, collects organic phase and is dried with anhydrous sodium sulfate, be concentrated to give the first thick production
Object；Step 2, the first crude product of purifying obtains single-side belt carbazole product；Step 3, by single-side belt carbazole product, Ar2, palladium, uncle
Sodium butoxide, tetrafluoro boric acid tri-tert-butylphosphine are placed in bottle, and sealing vacuumizes, and it is molten that toluene is added until after basic vacuum in drum argon gas
Solution, is heated to reflux, waits for after reaction, being cooled to room temperature, reaction solution dichloromethane and aqueous solution extraction, collects organic phase,
It is used in combination anhydrous sodium sulfate to dry, is concentrated to give the second crude product；Step 4, the second crude product of purifying is to get fluorescence red light material.
5. a kind of preparation method of asymmetric thermal activation delayed fluorescence red light material according to claim 4, feature exist
In diazosulfide, carbazole in step 1（Ar1）, potassium carbonate, copper powder molar ratio be 1:1:4:0.4, reflux temperature 175-
180 DEG C, return time is for 24 hours；It is purified by step 2 using petroleum ether and dichloromethane as solvent, passes through silica gel column chromatography
Column is completed, and the volume ratio of the dichloromethane and petroleum ether is 1：4, single-side belt carbazole product, Ar in step 32, palladium, uncle
Sodium butoxide, tetrafluoro boric acid tri-tert-butylphosphine molar ratio be 1:1:0.04:1:0.12, reflux temperature is 115-124 DEG C, when reflux
Between be purified by for 24 hours, in step 4 using petroleum ether and dichloromethane as solvent, completed by silica gel column chromatography, described two
The volume ratio of chloromethanes and petroleum ether is 1：3.
6. a kind of asymmetric thermal activation delayed fluorescence red light material according to claim 2, which is characterized in that work as Ar1It is non-
When carbazole, the general structure of the fluorescence red light material is
、、、、 Or。
7. based on a kind of preparation method of asymmetric thermal activation delayed fluorescence red light material described in claim 6, feature exists
In step 1, by diazosulfide, Ar1, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine be placed in bottle, seal, take out
Vacuum, drum argon gas are added toluene dissolving, are heated to reflux, after reaction, are cooled to room temperature, reaction solution is used until basic vacuum
Dichloromethane and aqueous solution extraction, organic phase are collected and are dried with anhydrous sodium sulfate, and the first crude product is concentrated to give；Step 2, it purifies
First crude product obtains unilateral product；Step 3, by unilateral product, Ar2, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine
It is placed in bottle, seals, vacuumize, drum argon gas adds toluene dissolving, be heated to reflux until basic vacuum, after reaction, cold
But to room temperature, reaction solution dichloromethane and aqueous solution extraction, organic phase is collected and is dried with anhydrous sodium sulfate, is concentrated to give second
Crude product；Step 4, the second crude product of purifying is to get fluorescence red light material.
8. a kind of preparation method of asymmetric thermal activation delayed fluorescence red light material according to claim 7, feature exist
In diazosulfide, Ar in step 11, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine molar ratio 1:1:0.04:
1:0.12, reflux temperature is 115-124 DEG C, and return time is for 24 hours；It is purified by step 2 and utilizes petroleum ether and dichloromethane work
It for solvent, is completed by silica gel column chromatography, the volume ratio of the dichloromethane and petroleum ether is 1：3, unilateral production in step 3
Object, Ar2, palladium, sodium tert-butoxide, tetrafluoro boric acid tri-tert-butylphosphine molar ratio be 1:1:0.04:1:0.12, reflux temperature is
115-124 DEG C, return time is purified by for 24 hours, in step 4 using petroleum ether and dichloromethane as solvent, passes through silica gel
Chromatographic column is completed, and the volume ratio of the dichloromethane and petroleum ether is 1：3.
9. being based on a kind of asymmetric thermal activation delayed fluorescence red light material described in claim 1 in organic electronic display field
Application.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109456276A (en) * | 2018-10-22 | 2019-03-12 | 武汉华星光电半导体显示技术有限公司 | Dark red photo-thermal activation delayed fluorescence material and its synthetic method, electroluminescent device |
| CN109627265A (en) * | 2018-11-26 | 2019-04-16 | 武汉华星光电半导体显示技术有限公司 | A kind of preparation method and Organic Light Emitting Diode of sensitized material |
| CN110386930A (en) * | 2018-04-18 | 2019-10-29 | 香港科技大学 | Aggregation-induced emission compound, preparation method and its application |
| WO2020082600A1 (en) * | 2018-10-22 | 2020-04-30 | 武汉华星光电半导体显示技术有限公司 | Near-infrared photothermal activation delayed fluorescent material and preparation method therefor, and display device |
| CN114621151A (en) * | 2022-03-25 | 2022-06-14 | 南京邮电大学 | Thermal activation delayed fluorescence semiconductor material and preparation method and application thereof |
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2018
- 2018-01-11 CN CN201810025211.9A patent/CN108358908A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110386930A (en) * | 2018-04-18 | 2019-10-29 | 香港科技大学 | Aggregation-induced emission compound, preparation method and its application |
| CN109456276A (en) * | 2018-10-22 | 2019-03-12 | 武汉华星光电半导体显示技术有限公司 | Dark red photo-thermal activation delayed fluorescence material and its synthetic method, electroluminescent device |
| WO2020082600A1 (en) * | 2018-10-22 | 2020-04-30 | 武汉华星光电半导体显示技术有限公司 | Near-infrared photothermal activation delayed fluorescent material and preparation method therefor, and display device |
| US11434419B2 (en) | 2018-10-22 | 2022-09-06 | Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. | Deep-red light thermally activated delayed fluorescent material and synthesizing method thereof, and electroluminescent device |
| CN109627265A (en) * | 2018-11-26 | 2019-04-16 | 武汉华星光电半导体显示技术有限公司 | A kind of preparation method and Organic Light Emitting Diode of sensitized material |
| CN114621151A (en) * | 2022-03-25 | 2022-06-14 | 南京邮电大学 | Thermal activation delayed fluorescence semiconductor material and preparation method and application thereof |
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