应用化学 ›› 2024, Vol. 41 ›› Issue (6): 783-799.DOI: 10.19894/j.issn.1000-0518.230400
• 综合评述 • 上一篇
王冠中1,4, 宋世平2, 彭红珍2, 张瑜3, 诸颖2, 陈静2()
收稿日期:
2023-12-29
接受日期:
2024-04-21
出版日期:
2024-06-01
发布日期:
2024-07-09
通讯作者:
陈静
基金资助:
Guan-Zhong WANG1,4, Shi-Ping SONG2, Hong-Zhen PENG2, Yu ZHANG3, Ying ZHU2, Jing CHEN2()
Received:
2023-12-29
Accepted:
2024-04-21
Published:
2024-06-01
Online:
2024-07-09
Contact:
Jing CHEN
About author:
chenjing929@shu.edu.cnSupported by:
摘要:
由于有机材料丰富的发光特性,有机发光二极管(OLEDs)在平面显示器和照明中的应用获得了广泛的关注。传统的有机发光二极管发光层材料主要为有机小分子或贵金属配合物,其中贵金属配合物,如铂(Ⅱ)和铱(Ⅲ),存在热稳定性较差、载流子传输能力有限、获取难度大、性能受限和材料价格高昂等问题,严重限制了其应用和发展。Cu(Ⅰ)配合物具有优异的发光特性、发射可调性和相对较低的成本,为开发金属配合物发光材料提供了新的途径。本文总结了基于Cu(Ⅰ)配合物的OLEDs发光材料的研究进展,探讨了改变配位原子类型和配体结构调节Cu(Ⅰ)配合物电致发光的策略,对Cu(Ⅰ)配合物OLEDs发光材料的发展前景予以展望。
中图分类号:
王冠中, 宋世平, 彭红珍, 张瑜, 诸颖, 陈静. 基于Cu(Ⅰ)配合物的OLEDs发光材料研究进展[J]. 应用化学, 2024, 41(6): 783-799.
Guan-Zhong WANG, Shi-Ping SONG, Hong-Zhen PENG, Yu ZHANG, Ying ZHU, Jing CHEN. Research Progress in OLEDs Emissive Materials Based on Cu(Ⅰ) Complexes[J]. Chinese Journal of Applied Chemistry, 2024, 41(6): 783-799.
图1 荧光(a)、磷光(b)和热激活延迟荧光(c)的分子机制示意图[3]
Fig.1 Schematic diagram to illustrate the molecular mechanism of (a) fluorescent, (b) phosphorescent and (c) thermally activated delayed fluorescence[3]
Ligands | ΔEST/eV | Emissions/nm a | PLQYs/% a | τ/μs a | EQE/% | Ref. |
---|---|---|---|---|---|---|
POP,ECAF | 0.09 | 550 | 22.4 | 5.7 | 14.81 | [ |
POP,EHCAF | 0.09 | 549 | 18.5 | 5.7 | 11.17 | [ |
POP,PCAF | 0.09 | 556 | 20.0 | 5.7 | 6.67 | [ |
POP,DMAC-PyPI | 0.11 | 534 | 62 | 21.4 | - | [ |
Xantphos,DMAC-PyPI | 0.08 | 533 | 71 | 24.1 | 5.91 | [ |
POP,PXZ-PyPI | 0.07 | 565 | 48 | 5.8 | 7.96 | [ |
Xantphos, PXZ-PyPI | 0.05 | 564 | 42 | 4.3 | - | [ |
Cbz,BINAP | 0.08 | 564 | 22 | 5.0 (91), 46.0 (9) | - | [ |
Cbz tBu,BINAP | 0.06 | 549 | 25 | 19.2 (74), 62.6 (26) | - | [ |
POP,PNNA | 0.12 | 493 | 60.9 | 145 | 5.83 | [ |
PNNA,Xantphos | 0.12 | 475 | 40.7 | 51 | 7.42 | [ |
PPh3,pptz | 0.09 | 490 | 89.87 | 23.6 | - | [ |
表1 配位原子为N、P的单核Cu(Ⅰ)配合物的光学性质
Table 1 The optical properties of mononuclear Cu(Ⅰ) complexes with N and P coordination atoms
Ligands | ΔEST/eV | Emissions/nm a | PLQYs/% a | τ/μs a | EQE/% | Ref. |
---|---|---|---|---|---|---|
POP,ECAF | 0.09 | 550 | 22.4 | 5.7 | 14.81 | [ |
POP,EHCAF | 0.09 | 549 | 18.5 | 5.7 | 11.17 | [ |
POP,PCAF | 0.09 | 556 | 20.0 | 5.7 | 6.67 | [ |
POP,DMAC-PyPI | 0.11 | 534 | 62 | 21.4 | - | [ |
Xantphos,DMAC-PyPI | 0.08 | 533 | 71 | 24.1 | 5.91 | [ |
POP,PXZ-PyPI | 0.07 | 565 | 48 | 5.8 | 7.96 | [ |
Xantphos, PXZ-PyPI | 0.05 | 564 | 42 | 4.3 | - | [ |
Cbz,BINAP | 0.08 | 564 | 22 | 5.0 (91), 46.0 (9) | - | [ |
Cbz tBu,BINAP | 0.06 | 549 | 25 | 19.2 (74), 62.6 (26) | - | [ |
POP,PNNA | 0.12 | 493 | 60.9 | 145 | 5.83 | [ |
PNNA,Xantphos | 0.12 | 475 | 40.7 | 51 | 7.42 | [ |
PPh3,pptz | 0.09 | 490 | 89.87 | 23.6 | - | [ |
图2 (a)配合物结构图; (b) OLEDs器件结构图; (c) OLED器件发射光谱; (d) OLEDs器件的亮度和电流密度与电压关系[28]
Fig.2 (a) Structures of complexes; (b) Device architecture of OLEDs; (c) Normalized EL spectra of OLEDs; (d) Luminance and current density versus voltage for the OLEDs devices[28]
图3 (a)配合物结构图; (b)配合物在二氯甲烷溶液中的紫外-可见光吸收光谱及发射光谱; (c) OLEDs器件结构图; (d)配合物器件外量子效率与亮度关系[29]
Fig.3 (a) Structures of complexes; (b) UV-Vis absorption and emission spectra of complexes in CH2Cl2 solution; (c) Device architecture of OLEDs; (d) EQE-luminance characteristics of OLEDs[29]
图4 (a) Cu(CbzR)[(S/R)-BINAP]的结构图; (b)固体状态配合物变温辐射寿命及热激活延迟荧光过程; (c)四氢呋喃溶液中(S/R)-1及(S/R)-2圆二色谱(虚线)及圆偏振发光(实线)谱; (d) OLEDs器件结构及电致发光光谱[30]
Fig.4 (a) Structures of Cu(CbzR)[(S/R)-BINAP]; (b) Temperature dependence of the radiative lifetimes of complexes in the ground solid state, and state diagrams visualizing the TADF processes; (c) CD (dashed lines) and CPL (solid lines) spectra of (S/R)-1 and (S/R)-2 in THF; (d) General OLEDs stack architecture and EL spectra[30]
ligands | ΔEST/eV | Emissions/nm | PLQYs/% | τ/μs a | EQE/% | Ref. |
---|---|---|---|---|---|---|
POP,pytzph | 0.09 | 509 | 43 | 5.5 | 7.6 | [ |
POP,pytzphcf | 0.13 | 519 | 29 | 16.0 | 6.2 | [ |
POP,pytzphcz | 0.09 | 503 | 79 | 5.5 | 8.3 | [ |
DPEPhos,TzTz | - | 712 | 1 | 3.1 | 0.32 | [ |
XantPhos,TzTz | - | 705 | 1 | 3.2 | 0.17 | [ |
Tpbz,pz4B | 0.07 | 580 | 7 | 20.5 | - | [ |
Tpbz,pz2BH2 | 0.08 | 569 | 28 | 11.9 | - | [ |
Tpbz,tz2BH2 | 0.04 | 540 | 45 | 7.4 | - | [ |
PymPPh2,MeCN | 0.09 | 515 | 47 | 27.0 | - | [ |
PymPPh2 | - | 525 | 15 | 22 | - | [ |
PymPPh2,PhCN | 0.06 | 550 | 65 | 9.6 | - | [ |
表2 配位原子为N、P的双核Cu(Ⅰ)配合物的光学性质
Table 2 The optical properties of binuclear copper complexes with N and P coordination atoms
ligands | ΔEST/eV | Emissions/nm | PLQYs/% | τ/μs a | EQE/% | Ref. |
---|---|---|---|---|---|---|
POP,pytzph | 0.09 | 509 | 43 | 5.5 | 7.6 | [ |
POP,pytzphcf | 0.13 | 519 | 29 | 16.0 | 6.2 | [ |
POP,pytzphcz | 0.09 | 503 | 79 | 5.5 | 8.3 | [ |
DPEPhos,TzTz | - | 712 | 1 | 3.1 | 0.32 | [ |
XantPhos,TzTz | - | 705 | 1 | 3.2 | 0.17 | [ |
Tpbz,pz4B | 0.07 | 580 | 7 | 20.5 | - | [ |
Tpbz,pz2BH2 | 0.08 | 569 | 28 | 11.9 | - | [ |
Tpbz,tz2BH2 | 0.04 | 540 | 45 | 7.4 | - | [ |
PymPPh2,MeCN | 0.09 | 515 | 47 | 27.0 | - | [ |
PymPPh2 | - | 525 | 15 | 22 | - | [ |
PymPPh2,PhCN | 0.06 | 550 | 65 | 9.6 | - | [ |
图5 (a) [Cu2(pytzph)(POP)2](BF4)2结构图; (b) OLEDs器件电致发光光谱; (c) OLEDs器件结构图; (d)配合物器件电流效率、外量子产率与电流密度关系[34]
Fig. 5 (a) Structures of [Cu2(pytzph)(POP)2](BF4)2; (b) Normalized EL spectra of OLEDs; (c) Device architecture of OLEDs; (d) Current efficiency and EQE versus current density for the OLEDs devices[34]
图6 (a) [Cu2(DPEPhos)2(TzTz)]2+结构图; (b) [Cu2(XantPhos)2(TzTz)]2+结构图; (c)基于 [Cu2(DPEPhos)2(TzTz)]2+分子OLEDs器件发射光谱; (d)基于[Cu2(XantPhos)2(TzTz)]2+分子OLEDs器件发射光谱[36]
Fig.6 (a) Structures of [Cu2(DPEPhos)2(TzTz)]2+; (b) Structures of [Cu2(XantPhos)2(TzTz)]2+; (c) Normalized EL spectra of OLEDs based on [Cu2(DPEPhos)2(TzTz)]2+; (d) Normalized EL spectra of OLEDs based on [Cu2(XantPhos)2(TzTz)]2+[36]
Ligands | ΔEST/eV | Emissions/nm | PLQYs/% | τ/μs a | EQE/% | Ref. |
---|---|---|---|---|---|---|
dppt1,I | 0.07 | 487 | 69 | 9.46 | 7.44 | [ |
dppt2,I | 0.05 | 483 | 86 | 7.62 | 14.50 | [ |
TTPP,Cl | 0.01 | 530 | 76 | 19 | 9.6 | [ |
TTPP,Br | 0.04 | 523 | 79 | 16 | 12.4 | [ |
TTPP,I | 0.05 | 521 | 83 | 11 | 16.3 | [ |
DBFDP,I | 0.16 | 491 | 5 | 2 | 0.73 | [ |
PPh3,HPBI,I | - | 581 | 38 | 8.2 | 3.4 | [ |
PPh3,MOPBI,I | - | 557 | 34 | 22.6 | - | [ |
PPh3,POPBI,I | - | 382 | 30 | 15.8 | - | [ |
dpmb,I | 0.12 | 498 | 32 | 2.5 | 10.1 | [ |
dpmb,Br | 0.12 | 511 | 28 | 12.5 | 7.3 | [ |
dpmb,Cl | 0.14 | 527 | 29 | 4.8 | 8.3 | [ |
表3 配位原子为 N、P、X(卤素) 的Cu(I)配合物的光学性质
Table 3 The optical properties of Cu(I) complexes with N,P,X(halogen) coordination atoms
Ligands | ΔEST/eV | Emissions/nm | PLQYs/% | τ/μs a | EQE/% | Ref. |
---|---|---|---|---|---|---|
dppt1,I | 0.07 | 487 | 69 | 9.46 | 7.44 | [ |
dppt2,I | 0.05 | 483 | 86 | 7.62 | 14.50 | [ |
TTPP,Cl | 0.01 | 530 | 76 | 19 | 9.6 | [ |
TTPP,Br | 0.04 | 523 | 79 | 16 | 12.4 | [ |
TTPP,I | 0.05 | 521 | 83 | 11 | 16.3 | [ |
DBFDP,I | 0.16 | 491 | 5 | 2 | 0.73 | [ |
PPh3,HPBI,I | - | 581 | 38 | 8.2 | 3.4 | [ |
PPh3,MOPBI,I | - | 557 | 34 | 22.6 | - | [ |
PPh3,POPBI,I | - | 382 | 30 | 15.8 | - | [ |
dpmb,I | 0.12 | 498 | 32 | 2.5 | 10.1 | [ |
dpmb,Br | 0.12 | 511 | 28 | 12.5 | 7.3 | [ |
dpmb,Cl | 0.14 | 527 | 29 | 4.8 | 8.3 | [ |
图7 (a) [Cu(μ2-I)dppt1]2及[Cu(μ2-I)dppt2]2结构图; (b) OLEDs器件结构图; (c) 12 V时2种OLEDs器件发射光谱; (d) 2种器件效率及外量子效率与亮度关系[45]
Fig.7 (a) Structures of [Cu(μ2-I)dppt1]2 and [Cu(μ2-I)dppt2]2; (b) Device architecture of OLEDs; (c) EL spectra of both devices at 12 V device architecture of OLEDs; (d) PE-L-EQE characteristics of both devices[45]
图8 (a) TTPPCuX(X= Cl,Br,I)化学式及TTPPCuBr单晶结构; (b) TTPPCuX变温寿命及变温量子产率; (c) 电流密度(中空)-亮度(实心)-电压曲线,1000 cd/m2时电致发光光谱和5 V时器件照片(插图); (d) 外量子产率与电流密度关系及根据单重态-三重态和三重态-三重态湮灭的拟合曲线[48]
Fig.8 (a) Chemical structure of TTPPCuX (X=Cl, Br, I) and single-crystal structure of TTPPCuBr; (b) Temperature dependence of emissive lifetime (τ) and PLQY for TTPPCuX; (c) Current density (J) (hollow)?-luminance (solid)-voltage curves, EL spectra at 1000 cd/m2 and device photos at 5 V (inset); (d) EQE-J correlations and the fitting curves according to TTA and STA+TTA models[48]
图9 (a) [DBFDP]2Cu4I4结构图; (b) [DBFDP]2Cu4I4单晶结构; (c)使用[DBFDP]2Cu4I4作为掺杂剂的OLEDs电致发光光谱、CIE坐标和照片(插图); (d)亮度-电流密度-电压关系曲线及外量子效率/激子利用率-电流密度曲线[49]
Fig.9 (a) Structures of [DBFDP]2Cu4I4; (b) Single-crystal structure and packing diagram of [DBFDP]2Cu4I4; (c) EL spectra, CIE coordinates and photographs (insets) of the OLEDs using [DBFDP]?2Cu4I4 as dopant; (d) Luminance-current density (J)-voltage relationship and EQE/EUE-J curves (inset)[49]
图10 (a) N^PCuI(PPh3)结构图; (b) OLEDs器件结构图; (c) 基于N^PCuI(PPh3)分子OLEDs器件发射光谱; (d) 电流效率、外量子产率与电流密度关系[51]
Fig.10 (a) Structures of N^PCuI(PPh3); (b) Device architecture of OLEDs; (c) Normalized EL spectra of OLEDs based on N^PCuI(PPh3); (d) Current efficiency-EQE-current density (J) relationship[51]
Ligands | ΔEST/eV | Emissions/nm | PLQYs/% | τ/μs a | EQE/% | Ref. |
---|---|---|---|---|---|---|
CAAC,Cz | 0.01 | 474 | 65 | 1.3 | 9.0 | [ |
MAC*,CzCN2 | - | 438 | 5 | 0.37(33%) 1.8(67%) | - | [ |
MAC*,CzCN | - | 474 | 76 | 0.75 | - | [ |
MAC*,Cz | 0.06 | 492 | 53 | 0.84 | 19.4 | [ |
MAC*,DPAC | 0.05 | 609 | 24 | 0.42 | 21.1 | [ |
MAC*,CzP | 0.06 | 559 | 40 | 0.4 | 15.2 | [ |
MAC*,CNCzP | 0.11 | 518 | 48 | 2.58 (77%) 34.1 (23%) | 13.2 | [ |
Ipr,dpa | 0.10 | 463 | 22 | 13 | - | [ |
Ipr,dpym | 0.12 | 473 | 15 | 6 | - | [ |
Ipr,dpyp | 0.10 | 474 | 73 | 14 | - | [ |
Ipr,PPhpy2 | 0.10 | 503 | 86 | 13 | - | [ |
表4 配位原子为N、C的Cu(Ⅰ)配合物的光学性质
Table 4 The optical properties of Cu(Ⅰ) complexes with N, C coordination atoms
Ligands | ΔEST/eV | Emissions/nm | PLQYs/% | τ/μs a | EQE/% | Ref. |
---|---|---|---|---|---|---|
CAAC,Cz | 0.01 | 474 | 65 | 1.3 | 9.0 | [ |
MAC*,CzCN2 | - | 438 | 5 | 0.37(33%) 1.8(67%) | - | [ |
MAC*,CzCN | - | 474 | 76 | 0.75 | - | [ |
MAC*,Cz | 0.06 | 492 | 53 | 0.84 | 19.4 | [ |
MAC*,DPAC | 0.05 | 609 | 24 | 0.42 | 21.1 | [ |
MAC*,CzP | 0.06 | 559 | 40 | 0.4 | 15.2 | [ |
MAC*,CNCzP | 0.11 | 518 | 48 | 2.58 (77%) 34.1 (23%) | 13.2 | [ |
Ipr,dpa | 0.10 | 463 | 22 | 13 | - | [ |
Ipr,dpym | 0.12 | 473 | 15 | 6 | - | [ |
Ipr,dpyp | 0.10 | 474 | 73 | 14 | - | [ |
Ipr,PPhpy2 | 0.10 | 503 | 86 | 13 | - | [ |
图11 (a) CAAC-Cu-NR2结构图; (b)配合物1a的HOMO和LUMO图; (c)电流-电压-亮度关系; (d)使用不同主体材料的EQE曲线(插图是基于1a的OLEDs照片) [57]
Fig.11 (a) Structures of CAAC-Cu-NR2; (b) HOMO (solid) and LUMO (mesh) surfaces of complex 1a; (c) Current (J)-voltage (V)-luminance (L) traces; (d) EQE traces of devices using different hosts (The inset is a photograph of a 1a-based device)[57]
图12 (a) (MAC*)Cu(CzRR')及(DAC*)Cu(CzRR')结构图; (b)室温及77 K发射光谱; (c)配合物3能级图;(d)外量子效率及基于配合物3的器件图(插图),配合物掺杂质量分数10%、40%和100%[63]
Fig.12 (a) Structures of (MAC*)Cu(CzRR') and (DAC*)Cu(CzRR'); (b) The emission spectra at room temperature (RT) and 77 K; (c) Energy level diagram for complex (MAC*)Cu(Cz); (d) External quantum efficiency. Inset: photograph of a (MAC*)Cu(Cz)-based device, doping mass concentrations of 3 are 10%, 40% and 100%[63]
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