Synthesis and Properties of Polymeric Host Materials Constructed by Silane-carbazole Backbone and Electron-affinitive Cyanohexyl Substituent for Blue Phosphorescence Dopant

doi:10.1007/s40242-017-6477-3

Abstract

Abstract:

A series of blue phosphor hosts, using 3,6-linked carbazole with δ-π tetraphenylsilane segment as the main chain and modified by peripheral cyanohexyl group with different ratios, was designed and synthesized. These polymers show good solubility in common organic solvents. They all possess wide bandgap of 3.40 eV, high thermal stabilities and good film forming abilities. The peripheral cyanohexyl substituents have no effect on the polymer backbones but enhance the electron transporting properties of the polymers in devices. Among them, doped devices using poly[(tetraphenylsilicon/9-hexyl-9H-3,6-carbazole)₅₀-co-(tetraphenylsilicon/9-hexanenitrile-9H-3,6-carbazole)]₅₀ (PCNCzSi50) as the host and bis[(4,6-difluorophenyl)pyridinato-N,C²]-(picolinato)iridium(III)(FIrpic) as the guest show the best performance with the maximum current efficiency and power efficiency of 2.00 cd/A and 1.40 lm/W, respectively.

Key words: Cyano group, Host, Phosphorescence, Polymer, Wide bandgap

HU Dehua, LIU He, LI Xiaoxiao, SUN Xiaoyi, LU Fang, BAI Qing, LU Ping. Synthesis and Properties of Polymeric Host Materials Constructed by Silane-carbazole Backbone and Electron-affinitive Cyanohexyl Substituent for Blue Phosphorescence Dopant[J]. Chemical Research in Chinese Universities, 2017, 33(2): 287-293.

References

[1] Baldo M. A., O'Brien D. F., You Y., Shoustikov A., Sibley S., Thompson M. E., Forrest S. R., Nature, 1998, 395, 151
[2] Ma Y., Zhang H., Che C., Shen J., Synth. Met., 1998, 94, 245
[3] Baldo M. A., Adachi C., Forrest S. R., Phys. Rev., B, 2000, 62, 10967
[4] Ren X., Li J., Holmes R. J., Djurovich P. I., Forrest S. R., Thompson M. E., Chem. Mater., 2004, 16, 4743
[5] Gong X., Robinson M. R., Ostrowski J. C., Moses D., Bazan G. C.,Heeger A. J., Adv. Mater., 2002, 14, 581
[6] Sudhakar M., Djurovich P. I., Hogen-Esch T. E., Thompson M. E., J. Am. Chem. Soc., 2003, 125, 7796
[7] Brunner K., Dijken A. V., Börner H., Bastiaansen J. J. A. M., Kiggen N. M. M., Langeveld B. M. W., J. Am. Chem. Soc., 2004, 126, 6035
[8] Su S. J., Sasabe H., Takeda T., Kido J., Chem. Mater., 2008, 20, 1691
[9] Ge Z., Hayakawa T., Ando S., Ueda M., Akiike T., Mayamoto H., Kajita T., Kakimoto M., Adv. Funct. Mater., 2008, 18, 584
[10] Tao Y., Wang Q., Yang C., Wang Q., Zhang Z., Zou T., Qin J., Ma D., Angew. Chem. Int. Ed., 2008, 47, 8104
[11] Gao Z. Q., Luo M., Sun X. H., Tom H. L., Wong M. S., Mi B. X., Xia P. F., Cheah K. W., Chen C. H., Adv. Mater., 2009, 21, 688
[12] Yeh S. J., Wu M. F., Chen C. T., Song Y. H., Chi Y., M Ho. H., Hsu S. F., Chen C. H., Adv. Mater., 2005, 17, 285
[13] Tsai M. H., Lin H. W., Su H. C., Ke T. H., Wu C. C., Fang F. C., Liao Y. L., Wong K. T., Wu C. I., Adv. Mater., 2006, 18, 1216
[14] Tsai M. H., Hong Y. H., Chang C. H., Su H. C., Wu C. C., Matoliukstyte A., Simokaitiene J., Grigalevicius S., Grigalevicius J. V., Hsu C. P., Adv. Mater., 2007, 19, 862
[15] Tao Y. T., Wang Q., Yang C. L., Zhong C., Zhang K., Qin J. G., Ma D. G., Adv. Funct. Mater., 2010, 20, 304
[16] Lamansky S., Djurovich P., Murphy D., Abdel-Razzaq F., Lee H. E., Adachi C., Burrows P. E., Forrest S. R., Thompson M. E., J. Am. Chem. Soc., 2001, 123, 4304
[17] Köhler A., Beljonne D., Adv. Funct. Mater., 2004, 14, 11
[18] Monkman A. P., Burrows H. D., Hartwell L. J., Horsburgh L. E., Hamblett I., Navaratnam S., Phys. Rev. Lett., 2001, 86, 1358
[19] Shih C., Rajamalli P., Wu C., Hsieh W., Cheng C. A., Acs Appl. Mater. Interfaces, 2015, 7, 10466
[20] Gong S., Sun N., Luo J., Zhong C., Ma D., Qin J., Yang C., Adv. Funct. Mater., 2014, 24, 5710
[21] Jeon S. O., Yook K. S., Joo C. W., Lee J. Y., Adv. Funct. Mater., 2009, 19, 3644
[22] Ding J., Zhang B., Lv J., Xie Z., Wang L., Jing X., Wang F., Adv. Mater., 2009, 21, 4983
[23] Jeon S. O., Yook K. S., Joo C. W., Lee J. Y., Adv. Mater., 2010, 22, 1872
[24] Chou H. H., Cheng C. H., Adv. Mater., 2010, 22, 2468
[25] Antoniadis H., Abkowitz M. A., Hsieh B. R., Appl. Phys. Lett., 1994, 65, 2030
[26] Kraft A., Grimsdale A. C., Holmes A. B., Angew. Chem. Int. Ed., 1998, 37, 402
[27] Friend R. H., Gymer R. W., Holmes A. B., Burroughes J. H., Marks R. N., Taliani C., Bradley D. D. C., Dos Santos D. A., Bré das J. L., Lögdlund M., Salaneck W. R., Nature, 1999, 397, 121
[28] Bernius M. T., Inbasekaran M., O'Brien J., Wu W., Adv. Mater., 2000, 12, 1737
[29] Liu M. F., Chen Y. L., Zhang C., Bo Z. S., Chin. J. Polym. Sci., 2012, 30, 308
[30] Chan K. L., Watkins S. E., Mak C. S. K., McKiernan M. J., Towns C. R., Pascu S. I., Holmes A. B., Chem. Commun., 2005, 5766
[31] Zhang X., Jiang C., Mo Y., Xu Y., Shi H., Cao Y., Appl. Phys. Lett., 2006, 88, 051116
[32] Gao X., Lu P., Ma Y. G., Chem. J. Chinese Universities, 2014, 35(9), 1795
[33] Chen Y. C., Huang G. S., Hsiao C. C., Chen S. A., J. Am. Chem. Soc., 2006, 128, 8549
[34] Avilov I., Marsal P., Brédas J. L., Beljonne D., Adv. Mater., 2004, 16, 1624
[35] Wu Z., Xiong Y., Zou J., Wang L., Liu J., Chen Q., Yang W., Peng J., Cao Y., Adv. Mater., 2008, 20, 2359
[36] Yeh H. C., Chien C. H., Shih P. I., Yuan M. C., Shu C. F., Macromolecules, 2008, 41, 3801
[37] Fei T., Cheng G., Hu D., Lu P., Ma Y., J. Polym. Sci. Part A:Polym. Chem., 2009, 47, 4784
[38] Hu D., Cheng G., Lu P., Liu H., Shen F., Li F., Lv Y., Dong W., Ma Y., Macromol. Rapid Commun., 2011, 32, 1467
[39] Greenham N. C., Moratti S. C., Bradley D. D. C., Friend R. H., Holmes A. B., Nature, 1993, 365, 628
[40] Lin Y., Chen Z. K., Ye T. L., Dai Y. F., Ma D. G., Ma Z., Liu Q. D., Chen Y., J. Polym. Sci. Part A:Polym. Chem., 2009, 48, 292
[41] Zhen C. G., Chen Z. K., Liu Q. D., Dai Y. F., Shin R. Y. C., Chang S. Y., Kieffer J., Adv. Mater., 2009, 21, 2425