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Acta Chimica Sinica >

2025 , Vol. 83 >Issue 5: 471 - 478

DOI: https://doi.org/10.6023/A25010010

Article

Xanthone Based Thermally Activated Delayed Fluorescence Enantiomers for Efficient Circularly Polarized Electroluminescence

  • Suqin Fang a ,
  • Kaining Tong b ,
  • Sihan Chen a ,
  • Qianfeng Zhang a ,
  • Bihai Tong , a, c, * ,
  • Mankeung Fung , b, * ,
  • Hui Kong , a, *
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  • a Institute of Molecular Engineering And Applied Chemistry, School of Metallurgy Engineering, Anhui University of Technology, Maanshan 243002, China
  • b Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Institute of Functional Nano & Soft Materials, Soochow University, Suzhou 215123, China
  • c State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023, China
* E-mail: ;
;

† These authors contributed equally to this work

Received date: 2025-01-07

  Online published: 2025-03-11

Supported by

National Natural Science Foundation of China(21572001)

Anhui Special Support Plan(T000609)

Distinguished Professor of the Wanjiang Scholars Project

Fold

Abstract

In order to develop cheap and high-efficient circularly polarized thermally activated delayed fluorescence (CP-TADF) materials, herein, we have designed and synthesized two pairs of chiral enantiomers (R/S)-AOBD and (R/S)-POBD by fusing the H8-BINOL skeleton into xanthone electron acceptor group. The electron donor groups of 9,10-dihydro-9,9-dimethylacridine or phenoxazine were used to regulate the emission wavelength and properties of materials. The photophysical and chiral optical properties of these materials have been studied. Electroluminescent devices using these materials were prepared by vapor deposition process and their performances were evaluated. Compounds exhibit good thermal stabilities. The decomposition temperatures (Td) of 5% weight loss are 433 ℃ for AOBD and 452 ℃ for POBD. The glass transition temperatures (Tg) of AOBD and POBD are 152 ℃ and 258 ℃. Their high Td and Tg can meet the requirements for material thermal stability in the organic light-emitting diodes (OLED) application and vacuum evaporation processes. These materials have moderate photoluminescence quantum efficiencies (0.34~0.43). They have small ∆EST (0.051~0.056 eV) and showed obvious aggregation-induced delayed fluorescence activity. The lowest unoccupied molecular orbitals (LUMOs) of these compounds are mostly located on the xanthone groups and the distribution proportion attributed to chiral H8-BINOL substructures is as high as 28%. Therefore, their photoluminescence (PL) spectra also have obvious circular polarization with dissymmetry factors (|gPL|) values between 5.4×10-4 and 9.0×10-4. The circularly polarized organic light-emitting diodes (CP-OLEDs) using these compounds show good performances with the maximum external quantum efficiency (EQEmax) of 10.6%~16.6% and intense circularly polarized electroluminescence signal with dissymmetry factor (|gEL|) of 2.2×10-3~5.4×10-3. These devices also exhibited high brightness (9118~32010 cd•m-2) and small efficiency roll-off (18%, at 1000 cd•m-2). The high performance in device efficiencies and dissymmetry factor of these materials is attributed to the full fusion of the H8-BINOL units with receptor groups, as well as their steric hindrance effect. It provides a good strategy for the development of stable electroluminescent materials with high efficiency and dissymmetry factor.

Key words： organic light-emitting diodes; circularly polarized luminescence; thermally activated delayed fluorescence; octahydronaphthol; xanthone

Cite this article

Suqin Fang , Kaining Tong , Sihan Chen , Qianfeng Zhang , Bihai Tong , Mankeung Fung , Hui Kong . Xanthone Based Thermally Activated Delayed Fluorescence Enantiomers for Efficient Circularly Polarized Electroluminescence[J]. Acta Chimica Sinica, 2025 , 83(5) : 471 -478 . DOI: 10.6023/A25010010

1 引言

随着有机发光二极管(OLEDs)的逐渐商业化, 圆偏振发光二极管(CP-OLEDs)因其在三维显示和加密信息存储方面的应用前景而受到越来越多的关注[1]. 热活化延迟荧光(TADF)材料作为最新一代的电致发光材料, 具有低成本和高效率的优点, 因此, 对于圆偏振TADF (CP-TADF)材料的研究变得非常重要[2]. 自2016年首次报道CP-TADF材料以来[3], 众多新型CP-TADF材料不断涌现. 手性1,1-双萘酚(BINOL)价格低廉、手性诱导能力强, 常被用于CP-TADF材料的分子设计[3-7]. 2019年, Cheng等[7]制备了一对TADF对映体, 其具有BINOL的扩展共轭骨架, 光致发光量子产率为18.5%, 其CP-OLED材料表现出橙红色发光, 最大外量子效率(EQEmax)为4.1%, 电致发光的不对称因子(|gEL|)约为1×10-3. 然而, 由于BINOL的扭转角较小(56.2o), 在衍生化过程中容易发生外消旋, 且其大的共轭分子骨架容易引起浓度猝灭[8-9]. BINOL的加氢产物八氢联萘酚(H8-BINOL)具有较大的扭转角(70o), 有利于提高手性构型的稳定性, 提高手性诱导能力. 此外, 增加的烷基空间位阻基团可以减少分子的堆积, 抑制分子浓度的猝灭, 使其更适合作为CP-TADF材料的合成块[10-18]. 一般来说, 增加TADF分子前沿轨道中手性基团的比例可以增强手性诱导的效果[19-20]. 在2022年, Zheng等[19]通过空间位阻辅助的双核策略制备了多重共振CP-TADF材料, 这些新材料实现了超纯的蓝色发射和圆偏振发光(CPL)特性. 用这些材料制备的CP-OLEDs的EQEmax为25.6%, |gEL|约为1×10-3. 虽然CP-TADF材料的研究已经取得了一些进展, 但要进入实际应用, 在材料成本、器件效率和不对称因子等方面仍存在许多挑战.
呫吨酮基团由于有较强的吸电子能力, 刚性平面的分子结构, 常作为电子受体单元用于TADF材料中[21], 但鲜有报道用于构建CP-TADF材料[22]. 为了开发低成本、高效率的CP-TADF材料, 我们将H8-BINOL骨架与呫吨酮电子受体基团充分融合, 合成了两对手性对映异构体. 利用9,10-二氢-9,9-二甲基吖啶或吩噁嗪电子供体基团来调节材料的发射波长和性质, 研究了这些材料的光物理性质和手性光学性质, 采用蒸镀工艺制备了电致发光器件, 并对其性能进行了研究.

2 结果与讨论

2.1 合成与表征

新化合物的合成路线如图1所示. 通过H8-BINOL与4-溴-2-氟苯甲酸甲酯之间的C—O偶联反应, 成功合成了中间体Z1, Z1的酯基水解后, 分子内环化得到了中间体Z2, 然后通过钯催化将Z2与9,10-二氢-9,9-二甲基吖啶和吩噁嗪进行C—N偶联反应, 分别得到目标产物AOBD和POBD, 产率为53%~61%. 目标产物通过核磁共振(NMR)和高分辨质谱(HRMS)进行表征, 高效液相色谱(HPLC)测试结果表明, 它们的手性纯度大于98%, 说明这些反应后H8-BINOL骨架构型没有变化.
图1 AOBD和POBD的合成路线

Figure 1 Synthetic routes of AOBD and POBD

(I) Methyl 4-bromo-2-fluorobenzoate, dimethylformamide, K2CO3, 110 ℃, N2, 12 h; (II) KOH, 4-dioxane, r.t., 12 h; (III) Trifluoroacetic acid, Trifluoroacetic anhydride, r.t., 12 h; (IV) Phenoxazine or 9,10-dihydro-9,9-dimethylacridine, t-BuOK, Pd(OAc)2, t-Bu3PHBF4, toluene, 110 ℃, N2, 12 h.

2.2 热物理性质和光物理性质

采用热重分析法(TGA)和差示扫描量热法(DSC)研究了这些新材料的热稳定性. 手性异构体除了具有手性性质外, 其他性质都非常相似, 因此只选择了R构型产物进行研究. 如图2所示, 两种化合物均表现出良好的热稳定性. 失重5%的分解温度(Td) AOBD为433 ℃, POBD为452 ℃. 如支持信息图S1所示, AOBD和POBD的玻璃化转变温度(Tg)分别为152和258 ℃. 它们的高Td和Tg可以满足在OLED应用时真空蒸发过程中对材料热稳定性的要求.
图2 AOBD和POBD的热重分析图

Figure 2 Thermogravimetric analysis plots of AOBD and POBD

测试了AOBD和POBD的紫外-可见吸收及光致发光(PL)光谱(图3). 如图3a所示, 380 nm以下的强吸收带是由共轭基团局部的π-π*跃迁引起, 而超过380 nm的弱吸收带, 则归因于电子供体和受体之间的分子内电荷转移. 9,10-二氢-9,9-二甲基吖啶基的供电子能力弱于吩噁嗪基, 因此化合物AOBD的紫外-吸收边缘较POBD发生蓝移. 两种化合物在二氯甲烷溶液中表现出非常弱的发光(PL量子产率小于2%). 然而, 它们表现出显著的聚集诱导发光特性(见支持信息图S2), 当AOBD和POBD在聚甲基丙烯酸甲酯(PMMA)薄膜中掺杂到浓度为1% (w)时, 这些化合物都表现出很强的发光能力(图3b). AOBD和POBD的PL峰分别为498和524 nm. 在固体粉末中, AOBD和POBD的发射波长分别红移到498和543 nm. 在PMMA薄膜中, AOBD和POBD具有中等的PL量子产率, 分别为0.34和0.43(表1), 而它们在微秒尺度上的长寿命(0.38~1.14 μs)说明了这些材料的TADF特性. 它们具有较小的∆EST值(0.051~0.056eV)(见支持信息图S4)和快速的反向系间窜越(RISC) (在77 K时的RISC速率常数[23]为1.3×106~3.0×106 s-1).
图3 AOBD和POBD的紫外-可见吸收和光致发光光谱: (a) CH2Cl2中AOBD和POBD紫外-可见吸收光谱图; (b)固体和1% (w) PMMA膜的光致发光光谱

Figure 3 UV-Vis absorption and photoluminescence spectra of AOBD and POBD: (a) UV-Vis absorption spectra of AOBD and POBD in CH2Cl2; (b) Photoluminescence spectra of solid and 1% (w) PMMA films

表1 AOBD和POBD的物理特性

Table 1 Physical characteristics of AOBD and POBD

Sample λema/nm Φb/% τpromptb/μs τdelayedb/ns Rdelayedb/% ∆EST c/eV E1/2ox d/V HOMOe/eV LUMOf/eV (Td/Tg)/℃
R-AOBD 559 (489) 34 0.38 24.0 15 0.051 0.559 –5.359 –2.743 433/152
R-POBD 599 (524) 43 1.14 29.8 30 0.056 0.386 –5.186 –2.755 452/258

a PL spectra were recorded in CH2Cl2 (PMMA films at a conc. of 1% (w)) at r.t. b Quantum yields and lifetime were recorded in PMMA films at a conc. of 1% (w) at r.t. c Measured at 77 K. d E1/2ox refers to [(Epa+Epc)/2], where Epc and Epa are the cathodic and anodic peak potentials referenced to the Fc+/Fc couple in CH2Cl2. e HOMO=–4.8–E1/2ox. f LUMO=HOMO+Egopt. Egopt was estimated from the absorption edge.

2.3 电化学性质和理论计算

采用循环伏安法研究了AOBD和POBD的电化学性质(图4). 化合物AOBD表现出不可逆氧化, 电位为0.559 V(相对于Fc+/Fc). 而化合物POBD具有可逆氧化作用, 电位为0.386 V(相对于Fc+/Fc). 由此可推算出化合物AOBD和POBD的最高占据分子轨道(HOMO)能级分别为–5.359和–5.186 eV. 这与9,10-二氢-9,9-二甲基吖啶基团的供电子能力弱于吩噁嗪基团的性质相一致. 然后结合由紫外-可见吸收边估算的能隙(Egopt), 推导出化合物AOBD和POBD的最低未占据分子轨道(LUMO)能级分别为–2.743和–2.755 eV. 它们LUMO能级相似的结果也与它们相同的电子受体结构相一致.
图4 AOBD和POBD的循环伏安曲线图

Figure 4 Cyclic voltammetry plots of AOBD and POBD

为了更加深入了解这些新化合物的电子结构, 进行了密度泛函理论(DFT)计算. 计算结果(图5)表明, 这些化合物的HOMO轨道主要位于电子供体基团(>96%)上, 即9,10-二氢-9,9-二甲基吖啶或吩噁嗪基团上. 而LUMOs主要位于呫吨酮基团上(>97%), 其中H8-BINOL的比例接近28%, 可以提高其手性诱导能力,前线轨道的分离分布有利于实现TADF, 因为这减少了T1和S1之间的能量分裂(ΔEST), 并加速了RISC[24]. 计算出的AOBD和POBD的HOMO/LUMO能级分别为 –5.44/–1.96和–5.23/–1.92 eV. 计算得到的垂直ΔEST值(AOBD为0.0152 eV, POBD为0.0182 eV)非常小, 有利于实现TADF. 这些理论计算结果与上述实验数据吻合良好.
图5 AOBD和POBD的HOMO和LUMO的能级图

Figure 5 Contour plots of the HOMOs and the LUMOs for AOBD and POBD

2.4 手性发光性质

为研究其手性发光性质, 测试了它们在室温下的圆二色性(CD)和圆偏振发光(CPL)光谱. 如图6(a, b)所示, 两对对映体在二氯甲烷溶液(1×10-5 mol•L-1)中表现出良好的镜像CD信号. 380 nm以下的吸收带可归因于呫吨酮基团的吸收, 而超过380 nm的吸收带可归因于分子内电荷转移的吸收. 它们强的CD信号表明, H8-BINOL的手性构型在一系列反应后得到了很好的维持. PMMA薄膜中两对对映体的CPL光谱(1% (w))也显示出近镜像对称的CPL信号(图6(c, d)). R/S-AOBD的光致发光不对称因子(gPL)值分别为7.5×10-4/–7.9×10-4(489 nm). R/S-POBD的值分别为5.4×10-4/–9.0×10-4(524 nm).
图6 CD和CPPL光谱

Figure 6 CD and CPPL spectra

2.5 电致发光特性

采用器件结构为氧化铟锡(ITO)/HAT-CN(10 nm)/TAPC(35 nm)/TCTA(10 nm)/mCP:新化合物(质量分数8%)(20 nm)/TmPyPB(50 nm)/LiQ(2 nm)/Al(120 nm) (图7)评价新发光材料的电致发光(EL)性能. 将1,3,5-三(3-吡啶基-3-苯基)苯(TmPyPB)和1,1'-双(二-4-甲苯氨基苯基)环己烷(TAPC)分别作为电子传递层和空穴传输层. 采用1,3-双(N-咔唑基)苯(mCP)作为主体材料, 发光材料的掺杂浓度为8% (w).
图7 器件构型和所用材料的化学结构

Figure 7 The device configurations and chemical structures of the materials used

这些器件的EL特征曲线和关键数据见图8和表2. 如图8a所示. 基于AOBD的器件DA显示蓝绿色电致发光, 最大峰值在488 nm, 国际照明委员会(CIE)坐标为(0.22, 0.42). 基于POBD的DP具有黄绿色电致发光, 最大峰值在548 nm处, CIE坐标为(0.41, 0.55). AOBD的EL谱与PMMA膜中的PL谱基本相同, 而POBD的EL谱相对于PMMA膜中的PL谱发生了24 nm的红移, 说明POBD更容易聚集, 没有检测到主体材料的发光, 这表明能量高效地从主体材料转移到发光材料中. 两个器件的开启电压在3.8~4.0 V之间, 其中DA和DP器件的最大亮度分别为9118和32010 cd•m-2.
图8 AOBD和POBD器件DA (AOBD)和DP (POBD)的特性曲线: (a)电致发光光谱; (b)电流密度-电压-亮度曲线; (c)电流效率-亮度-功率效率曲线; (d) EQE-亮度曲线; (e) CPEL光谱; (f) gEL值-波长曲线

Figure 8 Character curves of AOBD and POBD devices DA (AOBD) and DP (POBD): (a) Electroluminescent spectra; (b) Current density-voltage- luminance curves; (c) Current efficiency-luminance-power efficiency curves; (d) EQE-luminance curves; (e) CPEL spectra; (f) gEL values-wavelength curves

表2 AOBD和POBD器件发光和效率数据

Table 2 AOBD and POBD device luminescence and efficiency data

Device (dopant) λEL/nm Vona/V Lb/(cd•m-2) CEc/(cd•A-1) PEc/(lm•W-1) EQEc/% CIEd (x, y)
DA (AOBD) 488 3.8 9118 24.5 (21.4) 18.7 (12.3) 10.6 (8.6) (0.22, 0.42)
DP (POBD) 548 4.0 32010 53.3 (44.1) 41.7 (24.3) 16.6 (13.7) (0.41, 0.55)

a Turn on voltages at 1 cd•m-2; b Maximum luminance. c Maximum efficiency (efficiency at 1000 cd•m-2); d CIE coordinates at 7 V.

两种器件均表现出良好的电致发光效率. 如图8(c)和8(d)所示, 器件DA的最大电流效率(CE)和功率效率(PE)分别为24.5 cd•A-1和18.7 lm•W-1, 最大外部量子效率(EQEmax)为10.6%. 器件DP的效率更高, 最高效率分别为53.3 cd•A-1, 41.7 lm•W-1和16.6%. 此外, 两个器件表现出较小的效率下降, 即使在1000 cd•m-2的高亮度下, EQEs仅下降到其最大水平的82%. 这表明, 烷基空间位阻基团显著提高了器件的稳定性.
在上述相同的器件条件下, 研究了两对对映体的电致圆偏振发光(CPEL)特性. 如图8(e)和8(f)所示, 器件显示出明显的CPEL活性, 表明这些手性化合物能够承受蒸镀条件. R/S-AOBD的不对称因子(gEL)值分别为4.6×10-3/–5.4×10-3(488 nm), R/S-POBD的分别为2.2×10-3/–3.1×10-3(548 nm). 可以看出, 这些gPL值比PMMA薄膜中的gEL值显著增加. 这可能是由于EL器件中较高的掺杂浓度和薄膜的制备方法不同所致.

3 结论

综上所述, 我们设计并合成了两对CP-TADF对映体(R/S)-AOBD和(R/S)-POBD. 稳定的手性片段与TADF骨架完全融合, 具有良好的TADF和CPL性能. 这些材料具有较小的∆EST (0.051~0.056 eV)、中等的PL量子效率(0.34~0.43)和明显的聚集诱导发光(AIE)活性. 所有化合物均表现出良好的热稳定性(Td>430 ℃)和手性构型稳定性. 产物保持了手性原料的构型, 这些产物的手性构型能够承受蒸镀条件. 理论计算结果显示, 手性H8-BINOL单元在LUMO轨道中的分布比例高达28%. 对映体的CD和CPL光谱显示出镜像对称性. 基于(R)-AOBD和(S)-POBD的CP-OLEDs呈蓝绿和黄绿色发光, EQEmax分别为10.6%和16.6%. CPEL性能良好, |gEL|值在2.2×10-3和5.4×10-3之间. 这些器件显示出9118~32010 cd•m-2的高亮度和小的效率滚降(在1000 cd•m-2时仅降低18%). 这些材料的高效率和CPL性能归因于H8-BINOL单元与受体基团的完全融合以及其空间位阻效应. 该研究提供了一种方便的策略来平衡CP-TADF材料的器件效率和不对称因子.

4 实验部分

4.1 手性发光材料的合成

一般步骤: R/S-Z2 (0.6 g, 2.4 mmol)、9,10-二氢-9,9-二甲基吖啶或吩噁嗪(7.1 mmol)、t-BuOK (1.4 g, 12.5 mmol)、Pd(OAc)2 (4 mg, 0.02 mmol)和t-Bu3PHBF4 (16 mg, 0.06 mmol)以甲苯(40 mL)为溶剂在氮气气氛下回流12 h, 然后用减压法去除溶剂. 以石油醚/乙酸乙酯(V/V, 6∶1)为洗脱液, 用硅胶柱层析纯化, 得到相应的手性发光材料.
R/S-3,3'-bis(9,9-dimethylacridin-10(9H)-yl)-7,7',8,8', 9,9',10,10'-octahydro-12H,12'H-[6,6'-bibenzo[b]xanthene]-12,12'-dione (R/S-AOBD): 黄色固体, 产率分别为61%和58%. 1H NMR (400 MHz, CDCl3) δ: 8.55 (d, J=8.4 Hz, 2H), 8.19 (s, 2H), 7.45~7.42 (m, 4H), 7.31 (dd, J=8.4, 1.9 Hz, 2H), 7.14 (d, J=1.9 Hz, 2H), 6.95~6.90 (m, 8H), 6.28~6.25 (m, 4H), 3.04~2.99 (m, 4H), 2.48~2.40 (m, 2H), 2.38~2.29 (m, 2H), 1.85~1.71 (m, 8H), 1.64 (s, 12H); 13C NMR (101 MHz, CDCl3) δ: 176.73, 158.06, 151.60, 147.24, 144.90, 140.14, 134.51, 130.89, 129.27, 126.40, 126.31, 125.53, 123.59, 121.37, 121.28, 120.06, 119.73, 114.55, 36.11, 31.25, 29.50, 28.17, 22.59, 22.56; HRMS ((+)-ESI): m/z=913.3993 (calcd. 913.4005 for C64H53N2O4 [M+H]+).
R/S-3,3'-di(10H-phenoxazin-10-yl)-7,7',8,8',9,9',10, 10'-octahydro-12H,12'H-[6,6'-bibenzo[b]xanthene]-12,12'-dione (R/S-POBD): 黄色固体, 产率分别为54%和53%. 1H NMR (400 MHz, CDCl3) δ: 8.54 (d, J=8.3 Hz, 2H), 8.20 (s, 2H), 7.30 (dd, J=8.4, 1.9 Hz, 2H), 7.19 (d, J=1.9 Hz, 2H), 6.70~6.63 (m, 8H), 6.56~6.52 (m, 4H), 5.94 (dd, J=8.0, 1.4 Hz, 4H), 3.10~2.96 (m, 4H), 2.49~2.40 (m, 2H), 2.37~2.29 (m, 2H), 1.87~1.81 (m, 4H), 1.78~1.68 (m, 4H); 13C NMR (101 MHz, CDCl3) δ: 176.52, 157.88, 151.53, 145.07, 144.85, 143.98, 134.62, 133.37, 129.69, 126.54, 126.14, 123.50, 123.20, 122.06, 121.64, 120.15, 120.00, 115.83, 113.41, 29.51, 28.19, 22.58, 22.56; HRMS ((+)-ESI): m/z=861.2990 (calcd. 861.2965 for C58H41N2O6 [M+H]+).
(Cheng, B.)

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