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基于氮杂螺环配体的Cu(I)配合物延迟荧光材料的设计合成及性能研究

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化学学报 2024年

作者：张登朝贾吉慧梁栋蔡显宝赵雨晴胡祥龙江钰冰卢灿忠福建理工大学材料科学与工程学院中国科学院福建物质结构研究所中国科学院海西研究院厦门稀土材料研究中心福州大学化学学院

本研究通过采用具有室温磷光发射性质的给体-受体（D-A）型配体10-苯基-10H-螺[吖啶-9，9'-（4，5-二氮芴）]（Spiro2N），与辅助膦配体双（2-二苯基磷苯基）醚（POP）结合，成功设计了具有热活化延迟荧光（tadf）性质的Cu（I）配合... 详细信息

本研究通过采用具有室温磷光发射性质的给体-受体（D-A）型配体10-苯基-10H-螺[吖啶-9，9'-（4，5-二氮芴）]（Spiro2N），与辅助膦配体双（2-二苯基磷苯基）醚（POP）结合，成功设计了具有热活化延迟荧光（tadf）性质的Cu（I）配合物发光材料Cu-P-Spiro2N. 通过核磁共振谱图确认了Cu（I）配合物的分子结构. 进一步利用X射线单晶衍射表征了配合物Cu-P-Spiro2N的晶体结构. 结果表明，配合物Cu-P-Spiro2N属于三斜晶系，晶胞参数分别为α ＝ 90.14（2）°， β ＝ 115.43（3）°， γ ＝ 115.55（3）°， a ＝ 15.10（6） nm， b ＝ 15.15（4） nm， c ＝ 16.62（6） nm. 由于配体分子Spiro2N具有两个相互正交的π共轭平面结构，使得其HOMO和LUMO轨道具有很小的重叠，但具有相对较大的单重态-三重态能隙差(△EST). 金属Cu（I）片段与配体Spiro2N配位后，降低了HOMO-LUMO之间的能隙差，电荷转移（CT）态能级下降. 这使得配合物Cu-P-Spiro2N具有极小的△EST（0.05 eV）. 小的△EST有利于加速反系间窜越过程，进而实现tadf发射. 该类配合物的发射主要来自于D-A型配体Spiro2N，表现为金属微扰的配体内电荷转移（ILCT）性质. 室温下，在掺杂的PMMA薄膜（10 wt%）中，配合物Cu-P-Spiro2N表现出强烈的黄光发射，发射峰值位于551 nm，光致发光量子效率为49%，激发态寿命为6.3 μs. 本文研究结果表明，通过Cu（I）离子配位，可调控配体分子激发态能级，降低△EST，从而实现tadf发射.

关键词： Cu(I)配合物 tadf D-A型配体能级调控

Advanced charge transfer technology for highly efficient and long-lived tadf-type organic afterglow with near-infrared light-excitable property

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Science China Chemistry 2023年第4期66卷 1120-1131页

作者： Guangming Wang Xuefeng Chen Jiahui Liu Shuhui Ding Kaka Zhang Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China

Heavy atom effects and n-π*transitions have been frequently reported to enhance room-temperature organic phosphorescence efficiency but lead to shortage of phosphorescence lifetimes.Unlike these reported studies,we conceive the incorporation of advanced charge transfer(CT)technology to boost room-temperature organic afterglow efficiency and simultaneously maintain afterglow lifetimes.Here we design difluoroboronβ-diketonate(BF2bdk)CT compounds with moderate singlet-triplet splitting energy(ΔEST)of around 0.4 e V,and relatively large spin-orbit coupling matrix elements(SOCME(S_(1)-T_(1)),1–10 cm^(-1))to achieve efficient intersystem crossing(ISC)and moderate rates of reverse intersystem crossing(kRISC,1–10 s^(-1)).The advanced CT technology,which includes multiple electron-donating groups and orthogonal donor-acceptor arrangement,have been found to narrowΔESTand enhance both ISC and RISC.Meanwhile,the organic matrices suppress nonradiative decay of BF2bdk’s T1states by their rigid microenvironment.Consequently,thermally activated delayed fluorescence(tadf)-type organic afterglow materials can be achieved with afterglow efficiency up to 83.0%,long lifetimes of 433 ms,excellent processablility,as well as advanced anti-counterfeiting and information encryption.Furthermore,with the aid of up-conversion materials and through radiative energy transfer,tadf-type afterglow materials with aqueous dispersity and near-infrared light-excitable property have been achieved,which paves the way for biomedical applications.

关键词： afterglow charge transfer phosphorescence tadf triplet excited states

Dual-Responsive Thermally Activated Delayed Fluorescence of Spiropyran Derivatives

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CCS Chemistry 2022年第6期4卷 2080-2089页

作者： Liangwei Ma Guanghui Wang Bingbing Ding Xiang Ma Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center Frontiers Science Center for Materiobiology and Dynamic ChemistrySchool of Chemistry and Molecular EngineeringEast China University of Science&TechnologyShanghai 200237

For the first time,a series of photochromic dyes SP1-3 with dual-responsive thermally activated delayed fluorescence(tadf)characteristics were reported in this research.Benefitting from the reversible light-responsive property of SP1-3,the eigen tadf of these compounds could be regulated between 588 and 678 nm or turned on/off by different wavelengths of light irradiation in a polyvinylpyrrolidone(PVP)matrix.The emission lifetime of the spiropyran derivative was prolonged to millisecond level for the first time.Moreover,the delayed fluorescence of SP1 and SP3 could also be manipulated by mechanical force because of the mechanochromistic properties of SP1 and SP3.This research is a significant breakthrough for photochromic materials and may broaden its scope.

关键词： photochromism spiropyran mechanochromism tadf long-lived emission

tadf光敏剂设计合成与光催化脱卤反应性能研究

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有机化学 2023年

作者：刘亚鑫张渔罗书平浙江工业大学化学工程学院

以提高光催化效率为目的，我们设计与合成了一种三咔唑基苯二腈类的热延迟荧光（tadf）光催化剂，建立了在室温下光诱导的芳基卤代物的脱卤反应体系，以tadf为光催化剂，二硫醚作为氢转移催化剂，不同的有机卤化物（包括C-Br键和C-Cl键... 详细信息

以提高光催化效率为目的，我们设计与合成了一种三咔唑基苯二腈类的热延迟荧光（tadf）光催化剂，建立了在室温下光诱导的芳基卤代物的脱卤反应体系，以tadf为光催化剂，二硫醚作为氢转移催化剂，不同的有机卤化物（包括C-Br键和C-Cl键）都可以实现脱卤，且能得到中等至优异的产量。相较于热延迟荧光材料的代表4CzIPN，我们设计的3CzDMAPN具有更高催化效率和专一性。

关键词：光催化脱卤 tadf

Synthesis,Crystal Structure and Photoluminescence of a tadf Cuprous Complex

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Chinese Journal of Structural Chemistry 2018年第11期37卷 1749-1755页

作者：甘学敏吴小园余荣民卢灿忠 CAS Key Laboratory of Design and Assembly of Functional Nanostructures Fujian Provincial Key Laboratory of Nanomaterials Fujian Institute of Research on the Structure of MatterChinese Academy of Sciences Graduate University of Chinese Academy of Sciences

A four-coordinate mononuclear cuprous complex oCBP-Cu-Pym(1, oCBP =1,2-bis(diphenylphosphine)-nido-carborane, Pym = 2-methyl-6-(1 H-pyrazol-1-yl)pyridine) was synthe-sized and characterized by elemental analysis, NMR, UV-Vis and X-ray single-crystal structure analysis. It crystallizes in monoclinic space group C2/c with a = 28.4182(8), b =16.2994(4), c = 22.2708(5) ?, β = 127.219(2)°, V = 8214.8(3) ?3, Z = 8, Mr = 766.92, ρcalc = 1.24 g/cm3, F(000) = 3160, μ = 2.30 mm–1, GOOF = 1.063, the final R = 0.0700 and wR = 0.1903 for7158 observed reflections with I > 2σ(I). The Cu(I) ion adopts a highly distorted tetrahedral geometry defined by two nitrogen and two phosphorous atoms. Under UV 365 nm at room temperature, this complex exhibits green emission with maximum emission peak at 516 nm,lifetime 32.4 μs and quantum yield(ф = 0.461) in the solid state. Photophysical investigation suggests that the emission of complex 1 at room temperature was attributed to tadf, which is strongly supported by theoretic calculation.

关键词： Cu(Ⅰ) complex crystal structure tadf DFT calculation

Simultaneous enhancement of efficiency and stability of OLEDs with thermally activated delayed fluorescence materials by modifying carbazoles with peripheral groups

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Science China Chemistry 2019年第3期62卷 393-402页

作者： Yunge Zhang Dongdong Zhang Taiju Tsuboi Yong Qiu Lian Duan Key Lab of Organic Optoelectronics and Molecular Engineering of Ministry of Education Department of Chemistry Tsinghua University Department of Polymer Science and Engineering Zhejiang University

Albeit their high efficiencies, the operational stability of the organic light emitting diodes(OLEDs) based on thermally activated delayed fluorescence(tadf) emitters is still far from satisfaction, and few strategies have been proposed to improve their stability. Here, we show that by modifying the carbazole unit, one of the most commonly used donors in tadf emitters, with peripheral groups, both the device efficiency and operational stability can be greatly improved. Awell-known tadf molecule—4,5-di(9H-carbazol-9-yl)phthalonitrile(2CzPN) was chosen as the prototype and modified by introducing peripheral tert-butyl and phenyl groups to the 3,6-positions of the carbazole(named 2tBuCzPN and 2PhCzPN, respectively). The introduced groups not only improve the compounds' electrochemical stabilities referred to the cyclic voltammetry multi-sweep results, but also promote their photoluminescence quantum yields. Furthermore, reduced singlet-triplet energy gaps are observed, leading to the shortened exciton lifetimes which are benefit to suppress the exciton annihilations. Besides, the steric hindrance of introduced phenyl groups can partly restrain the concentration quenching of the tadf emitter. Consequently, OLEDs based on 2tBuCzPN and 2PhCzPN achieved improved maximum external quantum efficiencies(EQEs) of 17.0% and 14.0%, respectively(compared to 8.5% for 2CzPN). Meanwhile, 2PhCzPN based OLED showed reduced roll-off characteristics and a longer lifetime of 7.8 times higher than that of 2CzPN, testifying the effectiveness of subtle modification of the unstable moieties in simultaneous enhancement of efficiency and stability of OLEDs based on tadf emitters.

关键词： tadf OLED stability carbazole peripheral group

Organic Composite Crystal with Persistent Room-Temperature Luminescence Above 650 nm by Combining Triplet–Triplet Energy Transfer with Thermally Activated Delayed Fluorescence

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CCS Chemistry 2020年第5期2卷 1391-1398页

作者： Jian-Xin Wang Han Zhang Li-Ya Niu Xin Zhu Yan-Fei Kang Roman Boulatov Qing-Zheng Yang Key Laboratory of Radiopharmaceuticals Ministry of Education College of ChemistryBeijing Normal UniversityBeijing 100875 Department of Chemistry University of LiverpoolLiverpool L697ZD GB

Structural modifications are a successful and commonly used approach to tune the emission properties of diverse fluorophores,but extending this approach to heavy-atom-free persistent luminophores has so far been unsuccessful.Here we employed a novel strategy to demonstrate triplet–triplet energy transfer from an organic room-temperature phosphor(RTP)with persistent luminescence to an organic molecule with thermally activated delayed fluorescence(tadf).We illustrated this approach by preparing heavy-atom-free composite crystals of an RTP with a long-lifetime emission and a red emissive organic fluorophore with tadf to yield materials with emission above 650 nm.The emission arose from the triplet excited state of an acceptor undergoing thermally activated reverse intersystem crossing(RISC)to the emissive S1 state.Such composite crystal is the first organic material with persistent tadf,achieved by triplet–triplet energy transfer.

关键词： heavy-atom-free RTP persistent luminescence tadf energy transfer Anti-counterfeiting

非掺杂超薄发光层荧光白色有机电致发光器件的制备和研究

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光源与照明 2022年第5期 65-67页

作者：柴源董贺袁曦阮鹏吉林师范大学信息技术学院吉林四平136000

文章利用热致延迟荧光材料(tadf)双[4-(9,9-二甲基-9,10-二氢吖啶)苯基]硫砜(DMAC-DPS)为器件的主体及蓝光层,并通过调节橙色荧光材料2,8-二叔丁基-5,11-双(4-叔丁基苯基)-6,12-二苯基并四苯(TBRb)超薄层位置制备了结构简单、制备方便... 详细信息

文章利用热致延迟荧光材料(tadf)双[4-(9,9-二甲基-9,10-二氢吖啶)苯基]硫砜(DMAC-DPS)为器件的主体及蓝光层,并通过调节橙色荧光材料2,8-二叔丁基-5,11-双(4-叔丁基苯基)-6,12-二苯基并四苯(TBRb)超薄层位置制备了结构简单、制备方便的高效全荧光白色有机电致发光器件。器件的最大发光亮度为5 202 cd/m^(2),最大电流效率和外量子效率分别为13.6 cd/A和4.9%。结果表明,应用超薄层、非掺杂结构对简化器件结构和制备工艺具有显著作用。

关键词：有机电致发光器件超薄层 tadf DMAC-DPS

界面和发光层形貌优化提升溶液法天蓝色OLED效率

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界面和发光层形貌优化提升溶液法天蓝色OLED效率

作者：李博北京交通大学

学位级别：硕士

热激活延迟荧光（tadf）材料在理论上可以达到100%激子利用率,并且是由无贵金属掺杂的有机材料组成,有望成为下一代新型显示材料。目前限制tadf材料进一步发展的关键因素是蓝光材料器件效率低下的问题。因而,为了提升蓝光tadf有机发光... 详细信息

热激活延迟荧光（tadf）材料在理论上可以达到100%激子利用率,并且是由无贵金属掺杂的有机材料组成,有望成为下一代新型显示材料。目前限制tadf材料进一步发展的关键因素是蓝光材料器件效率低下的问题。因而,为了提升蓝光tadf有机发光二极管（OLEDs）的效率,本论文主要进行了以下几方面内容的研究:采用10-(4-（4,6-二苯基-1,3,5-三嗪-2-酮）（Spiro AC-TRZ）高效天蓝色tadf材料作为发光材料,通过调控界面和发光层材料,提升发光层薄膜质量,实现了极佳的能级结构和载流子平衡,获得了极高效率的蓝光器件。本文主要研究内容如下（1）本文通过研究Spiro AC-TRZ作为发光客体材料在不同器件结构下的光电特性,并通过在发光层前用高温交联的方法添加PVK层用来平衡载流子的输运,比较了不同厚度的PVK层以及主客体的掺杂比例,制备了较高效率的天蓝色tadf有机电致发光器件。（2）在（1）的研究前提下,我们通过在发光层中掺杂少量的聚合物来改善发光层的薄膜形貌。由于强烈的分子聚集,大多数小分子在溶液法的制备过程中表现出差的成膜性质,我们在发光层中加入少量PVK以改善发光层中小分子发光材料的成膜,使发光层的薄膜更致密和光滑。选择PVK作为发光层掺杂剂是由于其优异的成膜性和在氯苯中的良好溶解性。然而,由于PVK作为主体材料导致器件的低寿命和高驱动电压,并且难以克服其三线态能等原因,因此不适合高浓度的掺杂比,我们通过在发光层中掺入不同比例的PVK,测试器件的光电特性和表面形貌,最后得出当PVK的掺杂比例为10%时,对器件的优化性能最佳。本论文总共包含图51幅,表9个,参考文献67篇。

关键词：有机电致发光器件蓝光 tadf 高效率薄膜形貌