Synthesis and Properties of a Novel Triphenylamine Hole Transport Material

化学工业与工程

Chemcial Industry and Engineering

2020, Vol. 37

Issue (3) :23-30 DOI: 10.13353/j.issn.1004.9533.20191511

Current Issue | Next Issue | Archive | Adv Search

<< | >>

Synthesis and Properties of a Novel Triphenylamine Hole Transport Material

Zhang Songlin^1,2, Li Wei^1,2,3, Feng Wenhui^1,2, Wang Tianyang², Liu Dongzhi^1,3, Zhou Xueqin^1,2,3

1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350, China;
2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, China;
3. Tianjin Engineering Research Center of Functional Fine Chemicals, Tianjin 300350, China

Abstract	Reference	Related Articles

Download: PDF (2776KB) HTML () Export: BibTeX or EndNote (RIS) Supporting Info

Abstract Using 2,7-diiodo-9,9-dimethylindole as starting material, the Buchwald-Hartwig cross-coupling reaction and Ullmann reaction were used to obtain the target compound 9,9-dimethyl-N2, N7-diphenyl-N2, N7-di-P-tolyl-9H-fluorene-2,7-diamine(d-TPA). The elucidation of chemical structure was proved by ¹H NMR, ¹³C NMR and HRMS-ESI. It is shown that the Ullmann reaction with copper powder as the catalyst is the most efficient synthetic method (yield 85%). From the results of X-ray diffraction (XRD) and cyclic voltammetry (CV), the material was amorphous and has the ability to form a good thin film. And the compound has a highest occupied molecular orbit (HOMO) energy level of -5.23 eV, which is similar to the common anode material ITO work function and has good chemical stability, which is beneficial for the injection of hole carriers to the counter electrode. Organic lighting-emitting diodes (OLED) using the compound as hole transport material was prepared and characterized. The results show that the device has a light-emitting voltage of 3.8 V, a maximum luminance of 21 412 cd/m² and a maximum current efficiency of 4.78 cd/A. From the results, it has been proved that the compound is expected to be a novel hole transport material with excellent performance.

	Service

	Email this article
	Add to my bookshelf
	Add to citation manager
	Email Alert
	RSS
	Articles by authors
	Zhang Songlin
	Li Wei
	Feng Wenhui
	Wang Tianyang
	Liu Dongzhi
	Zhou Xueqin

Keywords： triphenylamine； synthesis； Ullmann reaction； amorphous material； OLED； hole transport material

Received 2019-05-20;

About author:

Cite this article:

Zhang Songlin, Li Wei, Feng Wenhui, Wang Tianyang, Liu Dongzhi, Zhou Xueqin.Synthesis and Properties of a Novel Triphenylamine Hole Transport Material[J] Chemcial Industry and Engineering, 2020,V37(3): 23-30

[1] Yang X, Wang H, Cai B, et al. Progress in hole-transporting materials for perovskite solar cells[J]. Journal of Energy Chemistry, 2018, 27(3):650-672
[2] Zhao X, Wang M. Organic hole-transporting materials for efficient perovskite solar cells[J]. Materials Today Energy, 2018, 7:208-220
[3] Bakr Z H, Wali Q, Fakharuddin A, et al. Advances in hole transport materials engineering for stable and efficient perovskite solar cells[J]. Nano Energy, 2017, 34:271-305
[4] Xiang N, Gao Z, Tian G, et al. Novel fluorene/indole-based hole transport materials with high thermal stability for efficient OLEDs[J]. Dyes and Pigments, 2017, 137:36-42
[5] Krucaite G, Volyniuk D, Simokaitiene J, et al. Naphthyl substituted triphenylamine derivatives as hole transporting materials for efficient red PhOLEDs[J]. Dyes and Pigments, 2019, 162:196-202
[6] Matebese F, Taziwa R, Mutukwa D. Progress on the synthesis and application of CuSCN inorganic hole transport material in perovskite solar cells[J]. Materials, 2018, doi:10.3390/ma11122592
[7] Rodriguez-Seco C, Cabau L, Vidal-Ferran A, et al. Advances in the synthesis of small molecules as hole transport materials for lead halide perovskite solar cells[J]. Accounts of Chemical Research, 2018, 51(4):869-880
[8] Zhang J, He Y, Min J. Recent progress in hybrid perovskite solar cells based on p-type small molecules as hole transporting materials[J]. Acta Physico-Chimica Sinca, 2018, 34(11):1221-1238
[9] 李园园, 张月, 王丽. 钙钛矿太阳能电池中空穴传输材料的研究进展[J]. 河南大学学报:自然科学版, 2017, 47(4):434-452 Li Yuanyuan, Zhang Yue, Wang Li. Research progress on hole transport materials for perovskite solar cells[J]. Journal of Henan University:Natural Science, 2017, 47(4):434-452(in Chinese)
[10] Liu X, Shi X, Liu C, et al. A simple carbazole-triphenylamine hole transport material for perovskite solar cells[J]. The Journal of Physical Chemistry C, 2018, 122(46):26337-26343
[11] Wu Y, Wang Z, Liang M, et al. Influence of nonfused cores on the photovoltaic performance of linear triphenylamine-based hole-transporting materials for perovskite solar cells[J]. ACS Applied Materials & Interfaces, 2018, 10(21):17883-17895
[12] Pina J, Seixas de Melo J S, Batista R M F, et al. Triphenylamine-benzimidazole derivatives:Synthesis, excited-state characterization, and DFT studies[J]. The Journal of Organic Chemistry, 2013, 78(22):11389-11395
[13] 姜姗姗. 含芴环化合物的合成及光学性能研究[D]. 太原:山西大学, 2011 Jiang Shanshan. Synthesis and optical performance of compound containing fluorene-based[D]. Taiyuan:Shanxi University, 2011(in Chinese)
[14] 李伟杰, 刘彬, 孙明礼. 4,5-二氮杂芴光电材料的合成及薄膜器件的应用[J]. 南京邮电大学学报:自然科学版, 2013, 33(5):1673-5439 Li Weijie, Liu Bin, Sun Mingli. The synthesis, properties and thin film device applications for 4,5-diazafluorene derivatives[J]. Journal of Nanjing University of Posts and Telecommunications:Natural Science, 2013, 33(5):1673-5439(in Chinese)
[15] 罗炫, 常冠军, 张林, 等. 含芴聚亚胺酮的合成与表征[J]. 合成化学, 2009, 17(1):15-18 Luo Xuan, Chang Guanjun, Zhang Lin, et al. Synthesis and characterization of fluorene-polyimine ketones[J]. Chinese Journal of Synthetic Chemistry, 2009, 17(1):15-18(in Chinese)
[16] Okumoto K, Shirota Y. Development of new hole-transporting amorphous molecular materials for organic electroluminescent devices and their charge-transport properties[J]. Materials Science and Engineering:B, 2001, 85(2/3):135-139
[17] Zhang J, Xu B, Johansson M B, et al. Constructive effects of alkyl chains:A strategy to design simple and non-spiro hole transporting materials for high-efficiency mixed-ion perovskite solar cells[J]. Advanced Energy Materials, 2016, doi:10.1002/aenm.201502536
[18] Tan C, Feng R, Peng X. Synthesis and electrochemical properties of 2, 6-bis(6-aryl-[1, 2, 4]-triazolo[3, 4-b] [1, 3, 4]-thiadiazole-3-yl)pyridines[J]. Chinese Chemical Letters, 2007, 18(5):505-508
[19] Yang Z, Xu B, He J, et al. Solution-Processable and thermal-stable triphenylamine-based dendrimers with truxene cores as hole-transporting materials for organic light-emitting devices[J]. Organic Electronics, 2009, 10(5):954-959
[20] Thesen M W, Krueger H, Janietz S, et al. Investigation of spacer influences in phosphorescent-emitting nonconjugated PLED systems[J]. Journal of Polymer Science Part A:Polymer Chemistry, 2010, 48(2):389-402
[21] 李英俊, 赵楠, 李丽娜, 等. 结构不对称三芳胺类化合物的合成、表征及性质研究[J]. 有机化学, 2012, 32(5):949-952 Li Yingjun, Zhao Nan, Li Lina, et al. Synthesis, characterization and properties of some novel structural asymmetric triarylamines[J]. Chinese Journal of Organic Chemistry, 2012, 32(5):949-952(in Chinese)