CN108530357A - Acridine D-A type thermal activation delayed fluorescence material, preparation method and application - Google Patents

Acridine D-A type thermal activation delayed fluorescence material, preparation method and application Download PDF

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CN108530357A
CN108530357A CN201710123857.6A CN201710123857A CN108530357A CN 108530357 A CN108530357 A CN 108530357A CN 201710123857 A CN201710123857 A CN 201710123857A CN 108530357 A CN108530357 A CN 108530357A
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structural formula
acridine
delayed fluorescence
thermal activation
activation delayed
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葛子义
杨荣娟
彭瑞祥
张磊
刘志洋
雷涛
李旺
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Ningbo Institute of Material Technology and Engineering of CAS
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract

The present invention provides a kind of acridine D A types thermal activation delayed fluorescence materials, contain similar electron-donating group acridine, change the overall structure of material by introducing the different electron-withdrawing group such as phenyl ring, fluorenes, carbazole and sulfone class, realize high-purity, multiple color especially blue light shine, the shortage and the bad problem of performance of current blue light thermal activation delayed fluorescence material can be improved.Such material structure is novel, performance is outstanding, can be synthesized by Ullmann coupling reactions, synthetic method is simple, yield is high, and emitting layer material can be used as in organic electroluminescence device, has higher luminous efficiency, lower efficiency roll-off, while can effectively reduce and open bright voltage.

Description

Acridine D-A type thermal activation delayed fluorescence material, preparation method and application
Technical field
The invention belongs to luminescent material technical field more particularly to a kind of acridine D-A type thermal activation delayed fluorescence material, Preparation method and application.
Background technology
In recent years, Organic Light Emitting Diode (organic light-emitting diode, OLED) is with its unique knot Structure, performance (light weight, bright in luster, small power consumption, flexible etc.) are fast-developing.TV, intelligence using OLED as screen The electronic products such as mobile phone are introduced to the market on a large scale, it means that OLED display technologies will welcome the peak period of development.Although The development of OLED in recent years is very fast, and R＆D-based growth is ripe, and occupation rate of market is substantially improved, but the selection of luminescent material is very big The development of OLED is limited in degree.
Luminescent material is the core of OLED technology, and first generation OLED material is with fluorescent material three (8-hydroxyquinoline) aluminium (Alq3) it is representative, the energy utilization efficiency of such material<25%；Second generation OLED material (the master of OLED display device at present Flow material) using phosphorescent iridium (Ir) complex as representative, the capacity usage ratio of such material is close to 100%, but there are prices Expensive, coloration not complete (blue phosphor materials shortage), iridium resource scarcity the problems such as.In view of luminescent material in OLED display technologies Key effect, and reduce the active demand of cost, industry just actively input research and development have both high-energy utilization ratio with it is cheap OLED material of new generation.
2009, Adachi seminars of Kyushu University utilized thermal activation delayed fluorescence (TADF) material tin porphyrin chemical combination Object prepares electroluminescent device, but electroluminescent device efficiency is only 0.3% (400K), therefore does not arouse attention.2012 Year, Adachi seminars obtained important breakthrough, and the external quantum efficiency (EQE) of TADF bases OLED is increased to 19.3%, has been broken glimmering The limit of light OLED, close to phosphorescent OLED.The sulfone of Adachi et al. designs makees receptor, and substituent group carbazole is the D-A type material of donor Material, opens bright voltage 4.0V, device external quantum efficiency 14.5%, and efficiency roll-off degree is greatly reduced.Seminar's the same year in The TADF material external quantum efficiencys based on sulfone receptoroid He other donor monomers delivered on Nature photonics are up to 19.5%.Over the past two years, researcher's discovery acridine donor material was given electrically with strong, after electron-withdrawing receptor is combined by force, The TADF device efficiencies of preparation are higher than existing major part TADF materials.The TADF material of main parts of Liao Liang lifes et al. synthesis and red After phosphor material doping the device red device external quantum efficiency for preparing up to 26% and efficiency roll-off amplitude it is smaller.Ting-An Et al. the TADF materials based on Acridine derivatives donor, triazines receptor unit day blue-light device efficiency close to 37%.
The breakthrough of luminescent material plays an important role the development of OLED, therefore research and development are novel, efficiently shine material Material, the especially research and development of pure, stabilised efficiency the blue light material of coloration become the target of field R＆D worker.
Invention content
The present invention provides a kind of acridine D-A type thermal activation delayed fluorescence materials, contain similar electron-donating group a word used for translation Pyridine changes the overall structure of material by introducing the different electron-withdrawing group such as phenyl ring, fluorenes, carbazole and sulfone class, realizes high-purity Degree, multiple color especially blue light shine, the shortage and performance of current blue light thermal activation delayed fluorescence material can be improved Bad problem.
That is, the technical scheme is that：A kind of acridine D-A type thermal activation delayed fluorescence material, chemical structural formula It is one kind in following chemical structural formula (1)-(60)：
In the above structural formula (1) to structural formula (60), each structural formula is independent of one another；
The above structural formula (26)-structural formula (28), structural formula (35), structural formula (36), structural formula (39), structural formula (40) In include R group it is also independent of one another, one kind in the alkyl selected from carbon atom number 1 to 12；
The above structural formula (41)-structural formula (48), the N being located in phenyl ring for including in structural formula (57)-structural formula (60) Also independently of one another, indicate that N may replace the H atom of any position on phenyl ring in the structural formula respectively.
Acridine D-A type thermal activation delayed fluorescence material provided by the invention has the advantages that：
(1) similar electron-donating group acridine is introduced, by introducing the different suction electricity such as phenyl ring, fluorenes and carbazole, sulfone class Subbase group changes the overall structure of material, realizes that high-purity, multiple color especially blue light shine, improves current blue light heat and live Change the shortage and the bad problem of performance of delayed fluorescence material；
(2) material structure is novel, performance is outstanding, can be synthesized by Ullmann coupling reactions, and synthetic method is simple, Step is few, and yield is high, and being reduced in terms of design of material can current emitting layer material manufacturing cost；
(3) improve current thermal activation delayed fluorescence material efficiency to roll-off serious problem, effectively reduce device and open bright voltage；
(4) material can be used as emitting layer material in organic electroluminescence device, due to a word used for translation under being acted in external voltage Pyridine donor monomer have strong electron donation can preferably be combined with phenyl ring, fluorenes, carbazole and sulfone receptoroid, and donor with By the connection such as singly-bound or phenyl ring, it can be achieved that certain molecular distortion, accounts for so as to preferably detach highest between receptor unit According to track (HOMO) and it is minimum do not occupy track (LUMO), smaller HOMO and LUMO overlappings can reduce singlet and triplet state Between energy level difference (Δ EST), make to alter between inverse system the more efficient of more process, therefore the OLED device of application such material can It realizes high luminous efficiency, effectively slow down efficiency roll-off phenomenon, while can effectively reduce and open bright voltage, and is different by regulating and controlling The combination of donor monomer and receptor unit, it can be achieved that yellow light, green light, blue light transmitting.
The present invention also provides a kind of method preparing above-mentioned acridine D-A type thermal activation delayed fluorescence material, this method Acridine is attached by least one of Ullmann coupling reactions and phenyl ring, fluorenes, carbazole and sulfone class, in formation State a kind of structure in structural formula (1)-structural formula (60).
Specific implementation mode
Below with reference to embodiment, the present invention will be further described.It should be pointed out that embodiment described below is intended to Convenient for the understanding of the present invention, and any restriction effect is not played to it.
Embodiment 1：
In the present embodiment, the structural formula of thermal activation delayed fluorescence material BP-Ph-DPAC is as follows：
The synthetic route of above-mentioned thermal activation delayed fluorescence material is as follows：
Specific building-up process is as follows：
By 4- benzoyl -4- bromo biphenyls (0.337g, 1.0mmol), 9,10- dihydro -9,9- diphenylacridines (0.37g, 1.1mmol), tri-tert-butylphosphine tetrafluoroborate (0.02g), sodium tert-butoxide (0.2g) are added in 100ml there-necked flasks, vacuumize and set It changes nitrogen three times, the toluene 20ml after drying is added.15min is stirred at room temperature, Pd is added2(dba)3(0.02g) is stirred at 120 DEG C 18h.It is cooled to room temperature, crosses elution column (being eluted with DCM), be spin-dried for, add silica white sample preparation, carry out pillar layer separation.It obtains white solid Body 0.54g (Y=92%), hexane/chloroform recrystallization.
Nuclear magnetic resonance spectroscopy product：1H NMR(400MHz,CDCl3) δ [ppm] 7.96 (d, J=7.84Hz, 2H), 7.89 (d, J=7.84Hz, 2H), 7.75-7.85 (m, 4H), 7.64 (t, J=7.6Hz, 1H), 7.54 (t, J=7.52Hz, 2H), 7.18-7.34 (m, 8H), 7.0-7.14 (m, 6H), 6.88-6.98 (m, 4H), 6.5-6.55 (d, J=8.2Hz, 2H).
Embodiment 2：
In the present embodiment, the structural formula of thermal activation delayed fluorescence material DPAC-PS-DPAC is as follows：
The synthetic route of above-mentioned thermal activation delayed fluorescence material is as follows：
Specific building-up process is as follows：
By 4,4 '-dibromo diphenyl sulphone (DPS)s (0.11g, 0.3mmol), 9,10- dihydro -9,9- diphenylacridines (0.23g, 0.66mmol), tri-tert-butylphosphine tetrafluoroborate (0.02g), sodium tert-butoxide (0.2g) are added in 100ml there-necked flasks, vacuumize It replaces nitrogen three times, the toluene 20ml after drying is added.15min is stirred at room temperature, Pd is added2(dba)3(0.02g) is stirred at 120 DEG C Mix 18h.It is cool to cross elution column (being eluted with DCM) but to room temperature, be spin-dried for, add silica white sample preparation, progress pillar layer separation to obtain white Solid 0.21g (Y=79%).
Nuclear magnetic resonance spectroscopy product：1H NMR (400MHz, CDCl3) δ [ppm] 8.05 (d, J=8.64Hz, 4H), 7.23 (m, 16H), 7.08 (t, J=7.36Hz, 4H), 6.87-6.99 (m, 16H), 6.48 (d, J=8.12Hz, 4H).
Embodiment 3：
In the present embodiment, the structural formula of thermal activation delayed fluorescence material BP-DPAC is as follows：
The synthetic route of above-mentioned thermal activation delayed fluorescence material is as follows：
Specific building-up process is as follows：
The synthesis of BP-DPAC.By 4- bromines benzophenone (0.055g, 0.21mmol), 9,10- dihydro -9,9- diphenyl a word used for translations 100ml there-necked flasks are added in pyridine (0.077g, 0.23mmol), tri-tert-butylphosphine tetrafluoroborate (0.02g), sodium tert-butoxide (0.2g) In, it vacuumizes displacement nitrogen three times, the toluene 15ml after drying is added.15min is stirred at room temperature, Pd is added2(dba)3(0.02g), 18h is stirred at 120 DEG C.It is cool to cross elution column (being eluted with DCM) but to room temperature, be spin-dried for, add silica white sample preparation, it carries out column chromatography and divides From.With methanol reprecipitation, white solid 0.09g (Y=83.5%) is obtained.
Nuclear magnetic resonance spectroscopy product：1H NMR(400MHz,CDCl3) δ [ppm] 7.96 (d, J=7.84Hz, 2H), 7.89 (d, J=7.84Hz, 2H), 7.64 (t, J=7.6Hz, 1H), 7.54 (t, J=7.52Hz, 2H), 7.18-7.34 (m, 8H), 7.0-7.14 (m, 6H), 6.88-6.98 (m, 4H), 6.5-6.55 (d, J=8.2Hz, 2H).
OLED device is prepared respectively using the thermal activation delayed fluorescence material in the present embodiment 1-3, which is layer Stack structure, typical structure are：ITO/HATCN(6nm)/NPB(30nm)/mCP(10nm)/samples(20nm)/DPEPO (10nm)/TPBi(35nm)/LiF(1nm)/Al(120nm).Wherein, what samples referred respectively to obtain in embodiment 1-3 has The structure of machine object, organic layer HATCN, NPB, mCP, DPEPO, TPBi is as follows：
The manufacturing process of the OLED device is as follows：
(1) material prepared in above-described embodiment 1-3 is put into ELS-60T-S vacuum sublimation equipment sublimation purifications, Under 1.5 × 10-3Pa vacuum degrees, 220 DEG C are gradually heating to, until material sublimation is complete.
(2) it first uses cleaning agent cleaning and dipping ito glass 20 minutes, then uses deionized water, acetone and isopropyl successively respectively Alcohol is cleaned by ultrasonic ito glass 30 minutes, and UV ozone is handled 15 minutes.
(3) ito glass is placed in vacuum chamber, is evacuated to 1 × 10-5To 9 × 10-3Pa.By above-mentioned on above-mentioned ITO Al layers of each organic layer of device architecture vacuum evaporation and cathode.Organic deposition rate control is existed
When applying external voltage appropriate to above-mentioned OLED device, since acridine donor monomer has strong electron donation can Preferably to be combined with benzophenone, sulfone receptoroid, and connected, it can be achieved that one by singly-bound or phenyl ring between donor and receptor unit Fixed molecular distortion, so as to preferably detach highest occupied molecular orbital (HOMO) and minimum do not occupy track (LUMO).It is smaller HOMO and LUMO overlappings can reduce energy level difference (Δ E between singlet and triplet stateST), make to alter between inverse system more process It is more efficient, it realizes high luminous efficiency and effectively slows down efficiency roll-off phenomenon.
Technical scheme of the present invention is described in detail in embodiment described above, involved other in the present invention The preparation method of derivative is similar with corresponding embodiment method, and the sequence only linked is different, is coupled by Ullmann anti- It answers, boration reaction and oxidation reaction can be made.It should be understood that above is only a specific embodiment of the present invention, not It, should all for limiting the present invention, all any modifications made in the spirit of the present invention, supplement or similar fashion replacement etc. It is included within protection scope of the present invention.

Claims (3)

1. a kind of acridine D-A type thermal activation delayed fluorescence material, chemical structural formula is following chemical structural formula (1)-(60) In one kind：
In the above structural formula (1) to structural formula (60), each structure is independent of one another；
The above structural formula (26)-structural formula (28), in structural formula (35), structural formula (36), structural formula (39), structural formula (40), R group wherein included is also independent of one another, one kind in the alkyl selected from carbon atom number 1 to 12；
The above structural formula (41)-structural formula (48), in structural formula (57)-structural formula (60), including the N being located in phenyl ring also that This independence indicates that N may replace the H atom of any position on phenyl ring in the structural formula respectively.
2. the preparation method of acridine D-A type thermal activation delayed fluorescence material as described in claim 1, it is characterized in that：By a word used for translation Pyridine class is attached by least one of Ullmann coupling reactions and phenyl ring, fluorenes, carbazole and sulfone class, forms above-mentioned knot A kind of structure in structure formula (1)-structural formula (60).
3. acridine D-A type thermal activation delayed fluorescence material conduct in organic electroluminescence device as described in claim 1 The application of emitting layer material.
CN201710123857.6A 2017-03-03 2017-03-03 Acridine D-A type thermal activation delayed fluorescence material, preparation method and application Pending CN108530357A (en)

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CN109293490A (en) * 2018-09-19 2019-02-01 信阳师范学院 Benzoyl loop coil aromatic hydrocarbons steric hindrance type luminescent material and preparation method thereof
CN111675693A (en) * 2020-05-20 2020-09-18 华南理工大学 D-A type luminous micromolecules containing acridine and phenanthroimidazole and application thereof in electroluminescent device
CN112142720A (en) * 2020-10-11 2020-12-29 徐州工程学院 Deep blue light molecule based on thermal activation delayed fluorescence mechanism and preparation method and application thereof
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CN112409259A (en) * 2020-10-13 2021-02-26 中国科学院宁波材料技术与工程研究所 Thermal activation delayed fluorescence micromolecule material, polymer material, organic electroluminescent device and preparation method
CN112851565A (en) * 2019-11-27 2021-05-28 杭州师范大学 Organic luminescent material with room-temperature phosphorescent performance and preparation method and application thereof
CN114213397A (en) * 2021-12-10 2022-03-22 维思普新材料（苏州）有限公司 1, 3-diazafluorenone derivatives and electronic devices
CN115724825A (en) * 2022-08-05 2023-03-03 黑龙江大学 Acridine phenyl phenanthroimidazole compound for preparing luminescent layer of electroluminescent device and preparation method thereof
CN116082236A (en) * 2022-12-24 2023-05-09 江汉大学 TADF luminescent material suitable for full solution process treatment technology and preparation method thereof

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CN109293490A (en) * 2018-09-19 2019-02-01 信阳师范学院 Benzoyl loop coil aromatic hydrocarbons steric hindrance type luminescent material and preparation method thereof
CN109293490B (en) * 2018-09-19 2021-07-09 信阳师范学院 Benzoyl spiro arene steric hindrance type luminescent material and preparation method thereof
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CN112851565A (en) * 2019-11-27 2021-05-28 杭州师范大学 Organic luminescent material with room-temperature phosphorescent performance and preparation method and application thereof
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CN112142720A (en) * 2020-10-11 2020-12-29 徐州工程学院 Deep blue light molecule based on thermal activation delayed fluorescence mechanism and preparation method and application thereof
CN112142720B (en) * 2020-10-11 2022-12-09 徐州工程学院 Deep blue light molecule based on thermal activation delayed fluorescence mechanism and preparation method and application thereof
CN112409259A (en) * 2020-10-13 2021-02-26 中国科学院宁波材料技术与工程研究所 Thermal activation delayed fluorescence micromolecule material, polymer material, organic electroluminescent device and preparation method
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