Synthesis and Characterization of 1,8-Disubstituted of Naphthalene Derivatives

• Main Authors: Yu-Chen Lin, 林煜宸
• Other Authors: Man-kit Leung
• Format: Others
• Language: zh-TW
• Published: 2015
• Online Access: http://ndltd.ncl.edu.tw/handle/89395422764860632968

碩士 === 國立臺灣大學 === 化學研究所 === 103 === In this study, a series of bipolar compounds that containing carbazole group at the 8-position of naphthalene, and with the 1-position substituted by an electron-withdrawing group (oxadiazole, benzimidazole, nitrile, and nitro, formic acid) were synthesized. The 1,8-position di-substituted naphthalene, being called as peri-substituted of naphthalene derivatives, has large steric hindrance resulting an orthogonal arrangement that interrupted the conjugation between the donating and the withdrawing groups. The 8-position substituted carbazole of naphthalene derivatives were discussed that intermolecular interaction between carbazole and withdrawing moieties and through measuring photophysical and electrochemical properties. Furthermore, we replaced carbazole group with bromine which has heavy atom effect, and demonstrated the properties of these naphthalene derivatives with different withdrawing moieties through measuring photophysical and electrochemical properties. Fluorescence, phosphorescence spectra and cyclic voltammetry were used to characterize the 1, 8-position di-substituted of naphthalene. The LUMO and the triplet state of all naphthalene derivatives are located in naphthalene structure. The triplet energy doesn’t change a lot with different substituent. The triplet energy of bipolar naphthalene derivatives are about 2.55 eV, and we found that compound 12 can transfer energy to the Ir(ppy)3 and the Ir(2-phq)2(acac) efficiently, so it is possible that these bipolar naphthalene derivatives become a good host material of green and red PhOLED.