Effects of Introducing Halogen Atoms to Biphenylmethyl Radical on Photostability, Photophysical and Electroluminescent Properties †

doi:10.7503/cjcu20190664

Chem. J. Chinese Universities ›› 2020, Vol. 41 ›› Issue (5): 972.doi: 10.7503/cjcu20190664

• Article • Previous Articles Next Articles

Effects of Introducing Halogen Atoms to Biphenylmethyl Radical on Photostability, Photophysical and Electroluminescent Properties ^†

WU Chunxiao,AI Xin,CHEN Yingxin,CUI Zhiyuan,LI Feng()

State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry,Jilin University, Changchun 130012, China

Received:2019-12-13 Online:2020-05-10 Published:2020-02-24
Contact: Feng LI E-mail:lifeng01@jlu.edu.cn
Supported by:
† Supported by the National Natural Science Foundation of China(51925303);† Supported by the National Natural Science Foundation of China(51673080);† Supported by the National Natural Science Foundation of China(91833304)

Abstract

Abstract:

Based on (N-carbazolyl)bis(2,4,6-trichlorophenyl) methyl(CzBTM), three new radicals, (3,6-difluoro-N-carbazoly)bis(2,4,6-trichlorophenyl) methyl (F₂CzBTM), (3,6-dichloro-N-carbazoly)bis(2,4,6-trichlorophenyl) methyl (Cl₂CzBTM) and (3,6-dibromo-N-carbazoly)bis(2,4,6-trichlorophenyl) methyl(Br₂CzBTM), were synthesized. By introducing the halogen atoms(F, Cl, Br) to the carbazole moiety, the electrochemical properties, theoretical calculation results, photophysical properties as well as photostability of the new radicals change obviously comparing with CzBTM. Cl₂CzBTM and Br₂CzBTM display higher photoluminescence quantum yield and F₂CzBTM exhibits the highest stability under a UV pulse laser irradiation. The organic light-emitting didoes(OLEDs) using Cl₂CzBTM and Br₂CzBTM as emitters were fabricated and the electroluminescence spectra of them are blue-shifted comparing with that of CzBTM. The maximum external quantum yield(EQE_max) of the devices based on Cl₂CzBTM and Br₂CzBTM are enhanced, which are 1.8 and 2.5 times that of CzBTM-based device, respectively.

Key words: Biphenylmethyl radical, Photostability, Doublet exciton, Organic light-emitting didoes(OLEDs)

CLC Number:

O644

TrendMD:

WU Chunxiao, AI Xin, CHEN Yingxin, CUI Zhiyuan, LI Feng. Effects of Introducing Halogen Atoms to Biphenylmethyl Radical on Photostability, Photophysical and Electroluminescent Properties ^†[J]. Chem. J. Chinese Universities, 2020, 41(5): 972.

Figures/Tables 12

Compound	CzBTM	F₂CzBTM	Cl₂CzBTM	Br₂CzBTM
∠N—C1—C2	117.4°	118.7°	118.8°	118.7°
∠N—C1—C3	118.3°	118.7°	118.8°	118.7°
∠C2—C1—C3	124.3°	122.7°	122.4°	122.6°
Dihedral angle between NC2C3 plain and 3,6-dihalocarbazole unit	40.2°	38.8°	39.5°	40.1°
Dihedral angle between NC2C3 plain and 2,4,6-trichlorophenyl including C2	49.7°	50.8°	48.5°	48.1°
Dihedral angle between NC2C3 plain and 2,4,6-trichlorophenyl including C3	46.5°	50.8°	48.5°	48.1°

Complex	E_red/V	E_ox/V	E_β_-SUMO/eV	E_α_-SOMO/eV
F₂CzBTM	-1.05	-0.02	-3.75	-4.78
Cl₂CzBTM	-1.02	0.03	-3.78	-4.83
Br₂CzBTM	-1.01	0.04	-3.79	-4.84
CzBTM^[19]	-1.09	-0.09	-3.71	-4.71

Complex	$Φ f a$ (%)	$Φ f b$ (%)	τ^c/ns	10^-6 $k d r$ /s^-1	10^-6 $k e nr$ /s^-1
CzBTM^[9]	2.0	5.0	4.0	5.0	245
F₂CzBTM	1.5	5.1	2.4	6.4	410.2
Cl₂CzBTM	5.5	9.8	5.3	10.3	185.8
Br₂CzBTM	7.6	17.1	6.5	11.7	142.1

Complex	$Φ f a$ (%)	$Φ f b$ (%)	τ^c/ns	10^-6 $k d r$ /s^-1	10^-6 $k e nr$ /s^-1
CzBTM^[9]	2.0	5.0	4.0	5.0	245
F₂CzBTM	1.5	5.1	2.4	6.4	410.2
Cl₂CzBTM	5.5	9.8	5.3	10.3	185.8
Br₂CzBTM	7.6	17.1	6.5	11.7	142.1

References 21

[1]	Tang C. W., VanSlyke S. A., Appl. Phys. Lett., 1987,51(12), 913—915
[2]	Uoyama H., Goushi K., Shizu K., Nomura H., Adachi C ., Nature, 2012,492(7428), 234—238 doi: 10.1038/nature11687 URL pmid: 23235877
[3]	Ma Y., Zhang H., Shen J., Che C., Synth. Met, 1998,94(3), 245—248
[4]	Baldo M., O'brien D., You Y., Shoustikov A., Sibley S., Thompson M., Forrest S., Nature, 1998,395, 151—154
[5]	Li F., A Kind of OLEDs Based on the Transition of Doublet Electron of Neutral Piradicals, ZL 201410018393, 2014-01-09
[6]	Hattori Y., Kusamoto T., Nishihara H., Angew. Chem. Int. Ed., 2014,53(44), 11845—11848 doi: 10.1002/anie.201407362 URL pmid: 25212390
[7]	Hattori Y., Kusamoto T., Sato T., Nishihara H., Chem. Commun, 2016,52(91), 13393—13396 doi: 10.1039/c6cc07898b URL pmid: 27787527
[8]	Peng Q. M., Obolda A., Zhang M., Li F., Angew. Chem. Int. Ed., 2015,54(24), 7091—7095 doi: 10.1002/anie.201500242 URL pmid: 25916621
[9]	Ai X., Chen Y. X., Li F., Angew. Chem. Int. Ed., 2018,57(11), 2869—2873 doi: 10.1002/anie.201713321 URL pmid: 29341421
[10]	Ai X., Evans E. W., Dong S., Gillett A. J., Guo H. Q., Chen Y. X., Hele T. J. H., Friend R. H., Li F., Nature, 2018,563(7732), 536—540 doi: 10.1038/s41586-018-0695-9 URL pmid: 30464267
[11]	Guo H. Q., Peng Q. M., Chen Y. X., Gu Q., Dong S., Evans E. W., Gillett A. J., Ai X., Zhang M., Credgington D., Coropceanu V., Friend R. H., Bredas J. L., Li F., Nat. Mater., 2019,18(9), 977—984 doi: 10.1038/s41563-019-0433-1 URL pmid: 31332338
[12]	Abdurahman A., Peng Q. M., Ablikim O., Ai X., Li F., Mater. Horiz., 2019,6(6), 1265—1270
[13]	Dong S. Z., Obolda A., Peng Q. M., Zhang Y., Marder S., Li F., Mater. Chem. Front., 2017,1(10), 2132—2135
[14]	Dong S. Z., Xu W., Guo H. Q., Yan W., Zhang M., Li F., Phys. Chem. Chem. Phys., 2018,20(27), 18657—18662 doi: 10.1039/c8cp01492b URL pmid: 29955740
[15]	Gamero V., Velasco D., Latorre S., López-Calahorra F., Brillas E., Juliá L., Tetrahedron Lett., 2006,47(14), 2305—2309
[16]	Velasco D., Castellanos S., López M., López-Calahorra F., Brillas E., Juliá L ., J. Org. Chem., 2007,72(20), 7523—7532 doi: 10.1021/jo0708846 URL pmid: 17824646
[17]	Hattori Y., Kusamoto T., Nishihara H., RSC Adv., 2015,5(79), 64802—64805
[18]	Hattori Y., Kusamoto T., Nishihara H., Angew. Chem. Int. Ed., 2015,54(12), 3731—3734 doi: 10.1002/anie.201411572 URL pmid: 25630936
[19]	Abdurahman A., Chen Y. X., Ai X., Ablikim O., Gao Y. C., Dong S. Z., Li B., Yang B., Zhang M., Li F., J. Mater. Chem. C, 2018,6(40), 11248—11254
[20]	Fan M. G., Fundamentals of Photochemistry and Material Science of Photonics, First Edition, Beijing, Science Press, 2001
	( 樊美公等. 光化学基本原理与光子学材料科学, 第一版, 北京: 北京科学出版社, 2001)
[21]	Rothberg L. J., Lovinger A. J., J. Mater. Res., 2011,11(12), 3174—3187

Effects of Introducing Halogen Atoms to Biphenylmethyl Radical on Photostability, Photophysical and Electroluminescent Properties ^†

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 12

References 21

Related Articles 2

Recommended Articles

Metrics

Comments

[1]	CHEN Xin, YAO Zu-Guang. Synthesis and Properties of N-Benzylindotricarbocyanine Dyes [J]. Chem. J. Chinese Universities, 1996, 17(10): 1613.
[2]	YAO Zu-Guang, CHEN Xia-Hua, ZHANG Qing-Hua. Syntheses and Properties of Unsymmetrical Trimethine Cyanines Containing Quinoline End Group [J]. Chem. J. Chinese Universities, 1995, 16(4): 579.