Blue Aggregation-Induced Delayed Fluorescence Materials with 5,10-Dihydrodibenzo[b,e][1,4]azasiline as Donor

doi:10.6023/cjoc202403047

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (8): 2513-2522.DOI: 10.6023/cjoc202403047 Previous Articles Next Articles

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以二苯基硅杂吖啶为电子给体的蓝色聚集诱导延迟荧光材料

何俊初^a, 伍俊琪^a, 王江辉^a, 徐静文^a, 唐本忠^b, 赵祖金^a^,^*()

a 华南理工大学发光材料与器件国家重点实验室广州 510640
b 香港中文大学(深圳)理工学院广东深圳 518172

收稿日期:2024-03-28 修回日期:2024-06-20 发布日期:2024-07-02
作者简介:
† 共同第一作者.
基金资助:
国家自然科学基金(U23A20594); 国家自然科学基金(22375066); 广东省基础与应用基础研究基金(2023B1515040003); 广东省基础与应用基础研究基金(2022A1515010315); 广东省基础与应用基础研究基金(2021A1515110826); 广州市科技计划(202201010439)

Blue Aggregation-Induced Delayed Fluorescence Materials with 5,10-Dihydrodibenzo[b,e][1,4]azasiline as Donor

Junchu He^a, Junqi Wu^a, Jianghui Wang^a, Jingwen Xu^a, BenZhong Tang^b, Zujin Zhao^a()

a State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640
b School of Science and Engineering, The Chinese University of Hong Kong, Shenzhen, Guangdong 518172

Received:2024-03-28 Revised:2024-06-20 Published:2024-07-02
Contact: *E-mail: mszjzhao@scut.edu.cn
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(U23A20594); National Natural Science Foundation of China(22375066); Guangdong Basic and Applied Basic Research Foundation(2023B1515040003); Guangdong Basic and Applied Basic Research Foundation(2022A1515010315); Guangdong Basic and Applied Basic Research Foundation(2021A1515110826); Guangzhou Science and Technology Planning Project(202201010439)

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Abstract

Three blue-emitting materials were developed using 10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline (DPDBA) and carbazole derivative as donors, and benzophenone as acceptor to construct donor-acceptor-donor (D-A-D') type molecules, and their thermal stability, electrochemical properties, single crystal structure, photophysical properties and electroluminescence properties were systematically studied. And they have small singlet-triplet energy splitting and microsecond- scale delayed lifetimes, showing obvious aggregation-induced delayed fluorescence (AIDF) characteristics. As light-emitting layers of organic light-emitting diodes (OLEDs), the electroluminescence peaks of these compounds are in the range of 474~ 476 nm, and the maximum external quantum efficiency (EQE) can reach 14.8%. Additionally, these compounds exhibit good bipolar carrier transport performance, and can be used as host materials for phosphorescent devices. The maximum EQEs of green and yellow phosphorescent OLEDs are 25.5% and 21.2%, respectively, and the efficiency roll-off at 1000 cd•m^－2 is very small. These results indicate that these AIDF compounds can be used not only as luminescent materials but also as host materials for the preparation of high-performance

Key words: organic light-emitting diode (OLED), aggregation-induced delayed fluorescence (AIDF), host material, aggregation-induced emission

Cite this article

Junchu He, Junqi Wu, Jianghui Wang, Jingwen Xu, BenZhong Tang, Zujin Zhao. Blue Aggregation-Induced Delayed Fluorescence Materials with 5,10-Dihydrodibenzo[b,e][1,4]azasiline as Donor[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2513-2522.

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Fig. & Tab. 10

Scheme 1. Synthetic route of compounds CP-BP-DPDBA, DCB-BP-DPDBA and CBP-BP-DPDBA

Figure 1. (A) Thermal stability and (B) electrochemical properties of CP-BP-DPDBA, DCB-BP-DPDBA and CBP-BP-DPDBA

Figure 2. Calculated frontier orbital distributions and energy levels of CP-BP-DPDBA, DCB-BP-DPDBA and CBP-BP-DPDBA

Figure 3. Crystal structure and molecular packing pattern and intermolecular interactions of CP-BP-DPDBA

Figure 4. (A) UV-Vis absorption spectra of CP-BP-DPDBA, DCB-BP-DPDBA and CBP-BP-DPDBA in THF solution (10－5 mol/L) and PL spectra in neat film, (B) PL spectra of CP-BP-DPDBA in THF/water mixtures with different fw (10－5 mol/L) excited at 340 nm, (C) PL decay curves of CP-BP-DPDBA in THF/water mixtures with different fw (10－5 mol/L) under nitrogen atmosphere at 300 K, and (D) temperature-dependent transient decay spectra of CP-BP-DPDBA in doped film with PPF under nitrogen atmosphere

Compd.	Solution^a			Neat film/doped film^b
Compd.	λ_abs/nm	Ф_PL^c/%	τ^d/ns	λ_em/nm	Ф_PL^c/%	τ^d/ns	τ^e/μs	k_RISC^f/10⁷ s^－1
CP-BP-DPDBA	337	6.0	50	469/472	10.3/37.1	1.0/39.4	6.2/166.8	—/0.98
DCB-BP-DPDBA	339	6.7	10	467/468	7.8/44.6	0.6/13.4	4.8/160.8	—/1.72
CBP-BP-DPDBA	339	12.1	7	460/470	4.1/42.1	3.2/7.0	40.0/30.0	—/5.50

Table 1. Summary of photophysical data of compounds CP-BP-DPDBA, DCB-BP-DPDBA and CBP-BP-DPDBA

Figure 5. Electroluminescence performances of CP-BP-DPDBA, DCB-BP-DPDBA and CBP-BP-DPDBA in doped OLEDs (A) Electroluminescent (EL) spectra at 10 mA?cm?2; (B) Luminance-voltage-current density curves; (C) Current efficiency-luminance-power efficiency curves; (D) External quantum efficiency-luminance curves. The device configuration is ITO/HATCN (5 nm)/NPB (30 nm)/mCP (10 nm)/EML (20 nm)/PPF (10 nm)/TPBi (50 nm)/LiF (1 nm)/Al

EML		V_on/V	L_max/(cd•m^－2)	η_C^b/(cd•A^－1)	η_P^b/(lm•W^－1)	EQE^b/%	λ_EL/nm		CIE/(x, y)
CP-BP-DPDBA		3.8	3170	23.6/7.8	19.5/3.4	13.2/4.4	474		(0.164, 0.261)
DCB-BP-DPDBA		3.4	3752	17.4/10.1	14.1/5.7	10.4/6.0	472		(0.156, 0.254)
CBP-BP-DPDBA	3.6		5168	25.7/2.6	22.4/1.0	14.8/1.5	476	(0.159, 0.248)

Table 2. Summary of electroluminescence data based on CP-BP-DPDBA, DCB-BP-DPDBA and CBP-BP-DPDBA

Figure 6. Electroluminescence performance of phosphorescent device based on CP-BP-DPDBA (A) EL spectra of at 10 mA?cm－2; (B) Luminance-voltage-current density curves; (C) External quantum efficiency-luminance curves. The devices were constructed with the configuration of ITO/HATCN (5 nm)/NPB (30 nm)/mCP (10 nm)/EML (20 nm)/PPF (10 nm)/TPBi (50 nm)/LiF (1 nm)/Al.

EML	V_on/V	L_max/(cd•m^－2)	η_C^b/(cd•A^－1)	η_P^b/(lm•W^－1)	EQE^b/%	λ_EL/nm	CIE/(x, y)
FirPic:A	3.2	28677	45.2/42.4	38.0/26.6	20.2/18.9 21.2/21.1 25.5/25.0 16.7/13.6	470	(0.161, 0.373)
Ir(ppy)₂acac:A	3.2	119911	78.8/78.5	59.3/51.4		520	(0.313, 0.638)
PO-01-TB:A	3.2	109871	85.9/84.4	63.2/57.6		558	(0.469, 0.526)
Ir(piq)₂acac:A	3.4	19063	14.7/11.4	12.2/6.1		622	(0.672, 0.323)
FirPic:B	3.2	6723	27.2/20.6	26.7/13.5 83.7/50.9 71.2/43.2 12.7/4.7	14.8/11.1 23.4/18.7 21.7/18.0 15.6/9.6	472	(0.149, 0.349)
Ir(ppy)₂acac:B	3.2	131771	85.3/68.0			520	(0.298, 0.643)
PO-01-TB:B	3.2	59680	72.6/60.4			558	(0.463, 0.524)
Ir(piq)₂acac:B	3.4	17302	13.8/8.1			622	(0.650, 0.320)
FirPic:C	3.2	15190	22.7/22.7	20.9/16.2	12.0/12.0	470	(0.149, 0.336)
Ir(ppy)₂acac:C	3.0	106887	76.6/62.9	80.2/49.4	21.8/17.5	520	(0.291, 0.644)
PO-01-TB:C	3.2	36036	70.7/53.1	69.3/36.2	21.3/16.0	556	(0.462, 0.527)
Ir(piq)₂acac:C	3.2	16444	12.9/8.2	12.7/5.2	14.8/9.4	622	(0.650, 0.320)

Table 3. Summary of phosphorescent device performance using CP-BP-DPDBA, DCB-BP-DPDBA and CBP-BP-DPDBA as hosts

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以二苯基硅杂吖啶为电子给体的蓝色聚集诱导延迟荧光材料

Blue Aggregation-Induced Delayed Fluorescence Materials with 5,10-Dihydrodibenzo[b,e][1,4]azasiline as Donor

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