Design and Synthesis of Phenothiazine Function-alized Spiro[fluorene-9,9'-xanthene] for Understanding Structure-property Relationships in Photoelectrical Properties

ZHAO Xiang-hua; WANG Li-min; MA Xiao; XU Wen-juan; CHEN Ming; YUAN Shun-dong; XU Zhi-Jie

doi:10.3788/fgxb20194001.0045

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Design and Synthesis of Phenothiazine Function-alized Spiro[fluorene-9,9'-xanthene] for Understanding Structure-property Relationships in Photoelectrical Properties

Synthesis and Properties of Materials | 更新时间：2020-08-12

- Design and Synthesis of Phenothiazine Function-alized Spiro[fluorene-9,9'-xanthene] for Understanding Structure-property Relationships in Photoelectrical Properties
- Chinese Journal of Luminescence Vol. 40, Issue 1, Pages: 45-51(2019)
- 作者机构：
  
  1. 信阳师范学院化学化工学院,河南信阳,464000
  2. 有机电子与信息显示国家重点实验室培育基地, 信息材料与纳米技术研究院, 江苏先进生物与化学制造协同创新中心, 南京邮电大学,江苏南京,210023
  3. 中国石油大学(华东) 理学院,山东青岛,266580
- 作者简介：
- 基金信息：
- DOI：10.3788/fgxb20194001.0045
  CLC： TN383+.1
- Received：22 March 2018，
  
  Revised：21 June 2018，
  
  Published Online：27 June 2018，
  
  Published：05 January 2019
- 稿件说明：
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赵祥华, 王莉敏, 马晓等. 吩噻嗪功能化的螺-9,9'-氧杂蒽芴的设计、合成及其光电性质与分子结构间的相互关系研究[J]. 发光学报, 2019,40(1): 45-51

ZHAO Xiang-hua, WANG Li-min, MA Xiao etc. Design and Synthesis of Phenothiazine Function-alized Spiro[fluorene-9,9'-xanthene] for Understanding Structure-property Relationships in Photoelectrical Properties[J]. Chinese Journal of Luminescence, 2019,40(1): 45-51
赵祥华, 王莉敏, 马晓等. 吩噻嗪功能化的螺-9,9'-氧杂蒽芴的设计、合成及其光电性质与分子结构间的相互关系研究[J]. 发光学报, 2019,40(1): 45-51 DOI： 10.3788/fgxb20194001.0045.

ZHAO Xiang-hua, WANG Li-min, MA Xiao etc. Design and Synthesis of Phenothiazine Function-alized Spiro[fluorene-9,9'-xanthene] for Understanding Structure-property Relationships in Photoelectrical Properties[J]. Chinese Journal of Luminescence, 2019,40(1): 45-51 DOI： 10.3788/fgxb20194001.0045.

摘要

合成了一种具有深的HOMO （-6.15 eV）分子轨道和高三线态能级（T

，2.82 eV）的新型化合物10-（2-螺-9，9'-氧杂蒽芴基）吩噻嗪（SFXPz）。因其宽的能带结构（

，4.22 eV）和深的HOMO能级而有望制备高效蓝色有机电致磷光器件。热重分析和差热扫描曲线表明，该化合物具有良好的热稳定性（

，259℃）和高的形态稳定性（

，206℃）。完全相互分离的HOMO和LUMO轨道有利于阻止分子内能量反转。SFXPz的紫外吸收峰分别位于230，260，292和310 nm左右；其荧光光谱两个发射峰分别位于311，324 nm左右。此外，该化合物的分子结构经LC-MS、

H NMR和

C NMR进行了详细表征。

Abstract

A novel 10-(spiro[fluorene-9

9'-xanthen]-2-yl)-phenothiazine(SFXPz) with deep HOMO(the highest occupied molecular orbital)(-6.15 eV) and high triplet energy(T

2.82 eV) has been synthesized

which is expected to fabricate high-efficient blue phosphorescent organic light-emitting diodes(PhOLEDs) due to the importance of a wide energy gap(

4.33 eV) and deep enough HOMO in blue PhOLEDs. The good thermal stability(

259℃) and high stable morphology(

206℃) of SFXPz were demonstrated by thermo gravimetric analysis(TGA) and differential scanning calorimetry(DSC) curves. The complete separation of HOMO and the lowest unoccupied molecular orbital(LUMO) of the compound is preferable to prevent the back of energy transfer. The UV-Vis spectrum peaks of SFXPz exhibit at around 230

260

292

310 nm

respectively

and the corresponding fluorescence emission spectrum peaks show at about 311

324 nm

respectively. In addition

the molecular structure is characterized detailedly by LC-MS

H NMR and

C NMR

respectively.

关键词

Keywords

references

BALDO M A,O'BRIEN D F,YOU Y,et al. Highly efficient phosphorescent emission from organic electroluminescent devices[J]. Nature, 1998,395(6698):151-154.

WONG M Y,ZYSMAN-COLMAN E. Purely organic thermally activated delayed fluorescence materials for organic light-emitting diodes[J]. Adv. Mater., 2017,29(22):1605444-1-54.

LIN C C,HUANG M J,CHIU M J,et al.. Molecular design of highly efficient thermally activated delayed fluorescence hosts for blue phosphorescent and fluorescent organic light-emitting diodes[J]. Chem. Mater., 2017,29(4):1527-1537.

ZHAO X H,WU Y K,ZHOU L,et al.. A bulky pyridinylfluorene/triphenylamine hybrid used as host material for heavily-doped blue electrophosphorescent devices[J]. Chin. J. Chem., 2016,34(4):397-342.

XU T,ZHANG Y X,WANG B,et al.. Highly simplified reddish orange phosphorescent organic light-emitting diodes incorporating a novel carrier-and exciton-confining spiro-exciplex-forming host for reduced efficiency roll-off[J]. ACS Appl. Mater. Interfaces, 2017,9(3):2701-2710.

HAN C M,ZHANG Z S,XU H,et al.. Short-axis substitution approach selectively optimizes electrical properties of dibenzothiophene-based phosphine oxide hosts[J]. J. Am. Chem. Soc., 2012,134(46):19179-19188.

YU D H,ZHAOF C,HAN C M,et al.. Ternary ambipolar phosphine oxide hosts based on indirect linkage for highly efficient blue electrophosphorescence:towards high triplet energy,low driving voltage and stable efficiencies[J]. Adv. Mater., 2012,24(4):509-514.

HAN C M,XIE G H,XU H,et al.. Towards highly efficient blue-phosphorescent organic light-emitting diodes with low operating voltage and excellent efficiency stability[J]. Chem. Eur. J., 2011,17(2):445-449.

HAN C M,XIE G H,LI J,et al. A new phosphine oxide host based on ortho-disubstituted dibenzofuran for efficient electrophosphorescence:towards high triplet state excited levels and excellent thermal,morphological and efficiency stability[J]. Chem. Eur. J., 2011,17(32):8947-8956.

BHANUCHANDRA M,YORIMITSU H,OSUKA A. Synthesis of spirocyclic diarylfluorenes by one-pot twofold SnAr reactions of diaryl sulfones with diarylmethanes[J]. Org. Lett., 2016,18(3):384-387.

REN B Y,ZHONG D K,SUN Y G,et al.. Quinolyl functionalized spiro[fluorene-9,9'-xanthene] host materials with bipolar characteristics for green and red phosphorescent organic light-emitting diodes[J]. Org. Electron., 2016,36:140-147.

LI J,DING D X,TAO Y T,et al.. A significantly twisted spirocyclic phosphine oxide as a universal host for high-efficiency full-color thermally activated delayed fluorescence diodes[J]. Adv. Mater., 2016,28(16):3122-3130.

ZHAO X H,XIE G H,LIU Z D,et al.. A 3-dimensional spiro-functionalized platinum(Ⅱ) complex to suppress intermolecular - and PtPt supramolecular interactions for a high-performance electrophosphorescent device[J]. Chem. Commun., 2012,48(32):3854-3856.

QIAN Y,NI Y R,YUE S Z,et al.. Spiro[fluorene-9,9'-xanthene]-based universal hosts for understanding structure-property relationships in RGB and white PhOLEDs[J]. RSC Adv., 2015,5(5):29828-29836.

XIE L H,LIU F,TANG C,et al.. Unexpected one-pot method to synthesize spiro[fluorene-9,9'-xanthene] building blocks for blue-light-emitting materials[J]. Org. Lett., 2006,8(13):2787-2790.

REN B Y,GUO R D,ZHONG D K,et al.. A yellow-emitting homoleptic iridium(Ⅲ) complex constructed from a multifunctional spiro ligand for highly efficient phosphorescent organic light-emitting diodes[J]. Inorg. Chem., 2017,56(14):8397-8407.

ZHAO X H,WU Y K,SHI N N,et al.. Carbazole-endcapped spiro[fluorene-9,9'-xanthene] with large steric hindrance as hole-transporting host for heavily-doped and high performance OLEDs[J]. Chin. J. Chem., 2015,33(8):955-960.

SUN M L,YUE S Z,CAO H T,et al.. Selective introduction of carbazole and diphenylamine into spirofluorenexanthene core for different phosphorescent hosts[J]. Chin. J. Chem., 2016,34(8):771-777.

XIAO L X,CHEN Z J,QU B,et al.. Recent progresses on materials for electrophosphorescent organic light-emitting devices[J]. Adv. Mater., 2011,23(8):926-952.

XIAO L X,SU S J,AGATA Y,et al.. Nearly 100% internal quantum efficiency in an organic blue-light electrophosphorescent device using a weak electron transporting material with a wide energy gap[J]. Adv. Mater., 2009,21(12):1271-1274.

JIA J H,WU Y Y. Alkyl length dependent reversible mechanofluorochromism of phenothiazine derivatives functionalized with formyl group[J]. Dyes Pigm., 2017,147:537-543.

ZHAO J,XIE G H,YIN C R,et al.. Harmonizing triplet level and ambipolar characteristics of wide-gap phosphine oxide hosts toward highly efficient and low driving voltage blue and green PHOLEDs:an effective strategy based on spiro-systems[J]. Chem. Mater., 2011,23(24):5331-5339.

GONG S L,CHEN Y H,LUO J J,et al.. Bipolar tetraarylsilanes as universal hosts for blue,green,orange,and white electrophosphorescence with high efficiency and low efficiency roll-off[J]. Adv. Funct. Mater., 2011,21(6):1168-1178.

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