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Progress in Chemistry 2023, Vol. 35 Issue (10): 1461-1485 DOI: 10.7536/PC230306 Previous Articles   Next Articles

• Review •

Multifunctional Organic Luminescent Materials Based on Benzophenone Frameworks

Wei Tang1, Yan Bing1, Xudong Liu1, Hongji Jiang1,2,3,*()   

  1. 1 State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials(IAM), Nanjing University of Posts & Telecommunications, Nanjing 210023, China
    2 State Key Laboratory of Molecular Engineering of Polymers (Fudan University), Shanghai 200438, China
    3 State Key Laboratory of Luminescent Materials and Devices (South China University of Technology), Guangzhou 510641, China
  • Received: Revised: Online: Published:
  • Contact: *e-mail: iamhjjiang@njupt.edu.cn
  • Supported by:
    National Natural Science Foundation of China(21574068); Major Research Program from the State Ministry of Science and Technology,(2012CB933301); Priority Academic Program Development of Jiangsu Higher Education Institutions(PAPD); Priority Academic Program Development of Jiangsu Higher Education Institutions(YX030003); Project of State Key Laboratory of Organic Electronics and Information Displays, Nanjing University of Posts and Telecommunication(GZR2023010056)
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The optoelectronic properties of organic luminescent materials are strongly correlated with the molecular structure, the flexibility of conformational change and the intermolecular interaction. From the perspective of structure, the carbonyl group and benzene ring of benzophenone have high chemical modifiability. In this paper, the chemical synthesis methods to produce multifunctional organic luminescent materials based on benzophenone framework in recent years are systematically reviewed, including three basic strategies: multiple substitution of benzophenone, using heteroatom as bridging group, vinyl coupling and direct coupling of benzene ring as the center. A variety of multifunctional organic luminescent materials based on this framework have been developed, including fluorescence materials, hosts of precious metal phosphorescence complex, thermally activated delayed fluorescence materials, aggregation-induced emission materials and pure organic room temperature phosphorescence materials. Finally, the development prospect of multi-functional organic luminescent materials based on benzophenone framework is prospected.

Contents

1 Introduction

2 Fluorescence materials based on benzophenone framework

3 Hosts based on benzophenone framework for precious metal phosphorescence complex

4 Thermally activated delayed fluorescence materials based on benzophenone framework

5 Aggregation-induced emission materials based on benzophenone framework

6 Pure organic room temperature phosphorescence materials based on benzophenone framework

7 Conclusions and outlook

Key words: benzophenone, chemically modified, multifunctional organic luminescent materials, fluorescence, host, thermally activated delayed fluorescence, aggregation-induced emission, room temperature phosphorescence
Fig.1 (a) The luminescence mechanism of organic luminescent materials. (b) Photoluminescence spectra of benzophenone in tetrahydrofuran solution at room temperature and 77 K, and photoluminescence spectrum of crystalline state at room temperature[5]
Fig.2 Chemical modification strategies for the molecular skeletons of benzophenone and their derivatives
Fig.3 Synthesis of benzophenone and polysubstituted benzophenone
Table 1 Optical physics and thermal stability parameters of benzophenone[5,7??~10]
material λ P L a ) (nm) λ P h b ) (nm) PLQYc)/d) (%) τd) (μs) S1/ T 1 e ) (eV) HOMO/LUMOe) (eV) Td (oC) Tg (oC)
benzophenone 310/380 410/440/472 0.001/15.9 312.9 3.6/2.9 -4.04/0.56 190 -56
Fig.4 Synthesis of heteroatom-bridged benzophenone
Fig.5 Synthesis of benzophenone derivatives with vinyl coupling and direct coupling of phenyl ring
Fig.6 (a) Chemical structures of 27~30. (b) Chemical structures and luminescence characteristics of 31 and 32[38,52,53]
Fig.7 (a) Chemical structure of 33. (b) Transient photocurrents in the layers of 33 at different sample voltages. Inserts show the one transient curve in linear plot. Arrows on insets indicate a transit time of holes. (c) The dependences of hole-drift mobility on the applied electric field in the amorphous layers of 33[54]
Fig.8 (a) Chemical structure of 34 and OLED luminescent picture. (b) Chemical structures of 35 and 36. (c) Images for the fluorescent colors of 36 in corresponding solution under ultraviolet light (365nm)[27,55,58,59]
Fig.9 (a) Chemical structures of 37~39. (b) The relationship between electron, hole mobility of 37 and half-wave potential E1/2. (c) Photograph of the light emitted by 38 and 39 under ultraviolet light at 365nm[24,62,63]
Fig.10 (a) Chemical structures of 40~43. (b) CIE coordinates of 42 and 43[68,69]
Fig.11 Chemical structure of 26[37]
Fig.12 (a) Chemical structures of 44 and 45. (b) EQE-luminance relationship curves of 44-based device 1 and 45-based device 2[41]
Fig.13 (a) Chemical structure of 46. (b) Blue, green and red phosphorescent OLED luminescent image based on 46[21]
Fig.14 (a) Chemical structure of 47. (b) Fluorescence and phosphorescence emission spectra of 47 in toluene at 77 K[81]
Fig.15 (a) Chemical structure of 48. (b,c) Current density and voltage characteristic curves of OLED devices A and B. (d) EQE and current density curves[83]
Fig.16 (a) Synthesis strategy of intermediate 4-bromo-9,9'-spiro-difluorene. (b) Chemical structures of 49~51[84,88,90]
Fig.17 (a) Chemical structures of 52 and 53. (b) Exciton transition routes of 52 and 53. The ratio of transient fluorescence and delayed fluorescence in the photoluminescence process of each material is shown at the bottom of the graph[104]
Fig.18 (a) Chemical structures of 54 and 55. (b) UV-vis (solid point) and photoluminescence spectra (hollow point) of 54 and 55 in dilute solution[111]
Fig.19 (a) Chemical structures of 56~58. (b) Doped device structures based on 56 and 57 and their EQE-luminance relationships[39,116]
Fig.20 (a) Chemical structure of 59. (b) EQE and luminance diagrams of devices 1 and 2[120,121]
Fig.21 Chemical structures of 60~62[35,36,122]
Fig.22 Chemical structures of 63~67[128]
Fig.23 (a) Chemical structures of 68 and 69. (b) EQE, power efficiency and current efficiency versus luminance characteristics of the OLED. (c) PL spectra, EL spectra at various operating voltages and photographs of doped OLED[132]
Fig.24 Chemical structures of 70~73[136]
Fig.25 (a) Chemical structures of 74~76. (b) The doping concentration dependence on the PLQY. (c) The doping concentration dependence on RISC rate constant (kRISC) and triplet non-radiative rate constant ( k n r T)[138]
Fig.26 (a) Chemical structures of 77 and 78. PL spectra of 77 (b) and 78 (c) in the mixtures of tetrahydrofuran and water at different volume ratios[124,151]
Fig.27 (a) Chemical structures of 79 and 80. (b) PL spectra of 79 in tetrahydrofuran and water mixtures with different water fractions. (c) Crystal of 80 under UV light at 365nm[148,153]
Fig.28 (a) Chemical structure of 81. (b) Photoluminescence spectra of 81 in CHCl3 and heptane mixtures with different heptane components (fw). (c) The relative strength (I/I0) changes with different components CHCl3 and heptane mixtures (5×10-6 M). The inset shows 81 in CHCl3 (fw=0, left) and CHCl3 and heptane mixtures (fw=90%, right) at 365nm illumination[154]
Fig.29 (a) Chemical structure of 82.; (b) Emission color of 82 solution (6 μmol/L) with different water contents in DMSO and H2O (λex=360nm )[155]
Fig.30 (a) Chemical structures of 83~87. (b) Crystal photographs of 83~87 under sunlight (top) and room temperature 365nm UV light (bottom) and non-luminous (300 K, top) and phosphorescent (77 K, bottom) photographs of 87 nitrogen degassed cyclohexane solutions (10-4 mol/L) under 365nm UV lamp irradiation[5,170,173]
Fig.31 Chemical structures of 88 and 89[174,175]
Fig.32 (a) Chemical structures of 90~97. (b) Luminescent photographs of 94~97 and corresponding RTP phosphorescent quantum yields[184,186]
Fig.33 (a) Chemical structures of 98 and 99. (b) RTP photographs of 98 and 99 exposed to 365nm UV light in trichloromethane and argon degassing trichloromethane solutions (2.0×10-5 mol/L). (c) Thin-film photographs of 98 and 99 in daylight (left) and thin-film RTP photographs in 312nm UV light (right). (d) RTP afterglow of 98 before and after 312nm UV irradiation[191]
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