Effect of Intermolecular Interaction on the Properties of Benzophenone-based AIDF Materials

doi:10.7503/cjcu20220562

Abstract

Abstract:

Four benzophenone luminescent materials with phenoxazine as donor were synthesized. The effects of different aromatic substituents on the intermolecular interaction and photoelectric properties of the materials were investigated. The coplanar modification of polycyclic aromatic hydrocarbons will result in a large number of strong π⁃π stacking interactions between molecules， while the three-dimensional triptycene group can avoid these interactions. The four compounds had very high thermal stability. Their temperature corresponding to 5% mass loss to the initia mass（T_d，5） was above 400 ℃， the π⁃π stacking between molecules will obviously improve the thermal stability of the materials. Except for the perylene modified compounds， the other three compounds had obvious aggregation- induced delayed fluorescence（AIDF）， their calculated energy gap（ΔE_st） values were not exceed 0.01 eV. Their photoluminescence efficiency in PMMA thin films was high. The photoluminescence efficiency in PMMA thin films was between 0.60 and 0.78， and increased first and then decreased with the decrease of intermole-cular force. The electroluminescent performance test showed that the compound modified by triptycene had the best electroluminescent performance. The maximum brightness of the doped device was up to 48480 cd/m²， and the peak power efficiency（PE_max） and peak external quantum efficiency（EQE_max） were 54.4 lm/W and 19.0%， respectively. The PE_max and EQE_max of the undoped device were still as high as 33.5 lm/W and 13.4%， indicating that the concentration quenching phenomenon was well suppressed and it has the potential to be applied to organic electroluminescence.

Key words: Aggregation-induced delayed fluorescence, Organic light emitting diode, Benzophenone, Intermolecular interaction

CLC Number:

O621.22

TrendMD:

WANG Yingjie, PAN Zehui, TAO Zhengyu, WANG Yan, TONG Bihai, FUNG Mankeung, SONG Mingxing. Effect of Intermolecular Interaction on the Properties of Benzophenone-based AIDF Materials[J]. Chem. J. Chinese Universities, 2023, 44(4): 20220562.

Figures/Tables 12

Table 1 Physical properties of PERCOP, TPECOP, TPCOP and ATPCOP

Sample	λ_max^a /nm	η^a （%）	τ^b /μs	ΔE_ST/eV^c	E $1 / 2 o x$ /V	HOMO ^d /eV	LUMO ^e /eV	E $g o p t$ /eV	T_d，5， T_g^f /℃
PERCOP	526（602）	31.1	0.016	1.505	0.59	-5.39	-3.03	2.36	419， —
TPECOP	522（540）	75.8	3.0	-0.297	0.35	-5.15	-2.74	2.41	420， —
TPCOP	515（533）	78.0	10.0	0.010	0.30	-5.10	-2.64	2.46	400， 140
ATPCOP	512（525）	62.4	11.6	0.010	0.25	-5.05	-2.48	2.57	403， 85

Table 1 Physical properties of PERCOP, TPECOP, TPCOP and ATPCOP

Sample	λ_max^a /nm	η^a （%）	τ^b /μs	ΔE_ST/eV^c	E $1 / 2 o x$ /V	HOMO ^d /eV	LUMO ^e /eV	E $g o p t$ /eV	T_d，5， T_g^f /℃
PERCOP	526（602）	31.1	0.016	1.505	0.59	-5.39	-3.03	2.36	419， —
TPECOP	522（540）	75.8	3.0	-0.297	0.35	-5.15	-2.74	2.41	420， —
TPCOP	515（533）	78.0	10.0	0.010	0.30	-5.10	-2.64	2.46	400， 140
ATPCOP	512（525）	62.4	11.6	0.010	0.25	-5.05	-2.48	2.57	403， 85

Table 2 Summary of device performances of as-prepared compounds

Device （Concentration）	λ_EL，max^a /nm	V_on^b /V	L^c /（cd·m^‒2）	CE_max/（cd·A^‒1）	PE_max/（lm·W^‒1）	EQE_max（%）	CIE _x_，_y^a coordinates
D1（10%）	568	4.6	1008	4.0	2.2	1.3	0.45， 0.53
D2（15%）	552	4.7	44280	50.0	33.0	16.9	0.41， 0.55
D3（15%）	544	3.5	48480	60.0	54.4	19.0	0.38， 0.55
D4（10%）	540	2.1	16520	26.3	20.6	8.6	0.36， 0.55
N1（100%）	612	5.3	858	0.5	0.3	0.3	0.55， 0.44
N2（100%）	576	6.0	18840	16.8	8.1	6.3	0.49， 0.50
N3（100%）	560	2.9	44010	41.0	33.5	13.4	0.45， 0.53
N4（100%）	548	4.2	13090	12.5	8.8	4.0	0.40， 0.55

References 25

1	Hong G.， Gan X. M.， Leonhardt C.， Zhang Z.， Seibert J.， Busch J. M.， Bräse S.， Adv. Mater.， 2021， 33（9）， 2005630
2	Wei Q.， Fei N. N.， Islam A.， Lei T.， Hong L.， Peng R. X.， Fan X.， Chen L.， Gao P. Q.， Ge Z. Y.， Adv. Opt. Mater.， 2018， 6（20）， 1800512
3	Uoyama H.， Goushi K.， Shizu K.， Nomura H.， Adachi C.， Nature， 2012， 492（7428）， 234—238
4	Liu Y. C.， Li C. S.， Ren Z. J.， Yan S. K.， Bryce M. R.， Nat. Rev. Mater.， 2018， 3（4）， 18020
5	Huang T. Y.， Jiang W.， Duan L.， J. Mater. Chem. C， 2018， 6（21）， 5577—5596
6	Liu H. J.， Liu H.， Fan J. Z.， Guo J. J.， Zeng J. J.， Qiu F. L.， Zhao Z. J.， Tang B. Z.， Adv. Opt. Mater.， 2020， 8（21）， 2001027
7	Jang J. S.， Han S. H.， Lee J. Y.， Adv. Photonics Res.， 2021， 2（5）， 2000109
8	Ma F. L.， Zhao X. X.， Ji H. F.， Zhang D. D.， Hasrat K.， Qi Z. J.， J. Mater. Chem. C， 2020， 8（35）， 12272—12283
9	Wu L.， Wang K.， Wang C.， Fan X. C.， Shi Y. Z.， Zhang X.， Zhang S. L.， Ye J.， Zheng C. J.， Li Y. Q.， Yu J.， Ou X. M.， Zhang X. H.， Chem. Sci.， 2021， 12（4）， 1495—1502
10	Cai X. Y.， Chen D. J.， Gao K.， Gan L.， Yin Q. W.， Qiao Z. Y.， Chen Z. J.， Jiang X. F.， Su S. J.， Adv. Funct. Mater.， 2018， 28（7）， 1704927
11	Lee S. Y.， Yasuda T.， Park I. S.， Adachi C.， Dalton Trans.， 2015， 44（18）， 8356—8359
12	Kreiza G.， Banevičius D.， Jovaišaitė J.， Maleckaitė K.， Gudeika D.， Volyniuk D.， Gražulevičius J. V.， Juršėnas S.， Kazlauskas K.， J. Mater. Chem. C， 2019， 7（37）， 11522—11531
13	Guo J. J.， Zhao Z. J.， Tang B. Z.， Adv. Opt. Mater.， 2018， 6（15）， 1800264
14	Lee S. Y.， Yasuda T.， Yang Y. S.， Zhang Q. S.， Adachi C.， Angew. Chem. Int. Ed.， 2014， 53（25）， 6402—6406
15	Zhang Q. S.， Tsang D.， Kuwabara H.， Hatae Y.， Li B.， Takahashi T.， Lee S. Y.， Yasuda T.， Adachi C.， Adv. Mater.， 2015， 27（12）， 2096—2100
16	Guo J. J.， Li X. L.， Nie H.， Luo W. W.， Gan S. F.， Hu S. M.， Hu R. R.， Qin A. J.， Zhao Z. J.， Su S. J.， Tang B. Z.， Adv. Funct. Mater.， 2017， 27（13）， 1606458
17	Chen X. J.， Yang Z.， Xie Z. L.， Zhao J.， Yang Z. Y.， Zhang Y.， Aldred M. P.， Chi Z. G.， Mater. Chem. Front.， 2018， 2（5）， 1017—1023
18	Liu H. J.， Zeng J. J.， Guo J. J.， Nie H.， Zhao Z. J.， Tang B. Z.， Angew. Chem. Int. Ed.， 2018， 130（30）， 9434—9438
19	Zhao Y. D.， Wang W. G.， Gui C.， Fang L.， Zhang X. L.， Wang S. J.， Chen S. M.， Shi H. P.， Tang B. Z.， J. Mater. Chem. C， 2018， 6（11）， 2873—2881
20	Wang Y.， Xiao Y. P.， Zhou Y. Y.， Hu C. G.， Tong B. H.， Ye S. H.， Mei Q. B.， Dalton Trans.， 2019， 48（43）， 16289—16297
21	Zhou Y. Y.， Xu D. Y.， Cheng W.， Wang Y.， Tong B. H.， He G. F.， Tian Y. P.， New J. Chem.， 2020， 44（20）， 8587—8594
22	Jing Y. Y.， Tao X. D.， Yang M. X.， Chen X. L.， Lu G. Z.， Chem. Eng. J.， 2021， 413， 127418
23	Kang L. T.， Wang Z. C.， Cao Z. W.， Ma Y.， Fu H. B.， Yao J. N.， J. Am. Chem. Soc.， 2007， 129（23）， 7305—7312
24	Xiong Y.， Huang J.， Liu Y. J.， Xiao B. O.， Xu B.， Zhao Z. J. Tang B. Z.， J. Mater. Chem. C， 2020， 8（7）， 2460—2466
25	Tong B. H.， Wang H.， Chen M.， Zhou S. X.， Hu Y. Y.， Zhang Q. F.， He G. F.， Fu L. S.， Shi H. T.， Jin L.， Zhou H. D.， Dalton Trans.， 2018， 47（35）， 12243—12252

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