Acridine Based Small Molecular Hole Transport Type Materials for Phosphorescent OLED Application

Two small molecular hole-transporting type materials, namely 4-(9,9-dimethylacridin-10(9H)-yl)-N-(4-(9,9-dimethylacridin-10(9H)-yl)phenyl)-N-phenylaniline (TPA-2ACR) and 10,10′-(9-phenyl-9H-carbazole-3,6-diyl)bis(9,9-dimethyl-9,10-dihydroacridine) (PhCAR-2ACR), were designed and synthesized using a single-step Buchwald–Hartwig amination between the dimethyl acridine and triphenylamine or carbazole moieties. Both materials showed high thermal decomposition temperatures of 402 and 422 °C at 5% weight reduction for PhCAR-2ACR and TPA-2ACR, respectively. TPA-2ACR as hole-transporting material exhibited excellent current, power, and external quantum efficiencies of 55.74 cd/A, 29.28 lm/W and 21.59%, respectively. The achieved device efficiencies are much better than that of the referenced similar, 1,1-Bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC)-based device (32.53 cd/A, 18.58 lm/W and 10.6%). Moreover, phenyl carbazole-based PhCAR-2ACR showed good device characteristics when applied for host material in phosphorescent OLEDs.

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A Solution-Processed Tetra-Alkoxylated Zinc Phthalocyanine as Hole Transporting Material for Emerging Photovoltaic Technologies

International Journal of Photoenergy ◽

10.1155/2018/2473152 ◽

2018 ◽

Vol 2018 ◽

pp. 1-9

Author(s):

Gloria Zanotti ◽

Giuseppe Mattioli ◽

Anna Maria Paoletti ◽

Giovanna Pennesi ◽

Daniela Caschera ◽

...

Keyword(s):

Perovskite Solar Cells ◽

Single Step ◽

Hole Transport ◽

Transport Layer ◽

Zinc Phthalocyanine ◽

Hole Transport Layer ◽

Solution Processed ◽

Ab Initio Simulations ◽

Hole Transporting ◽

Hole Transporting Material

A tetra-n-butoxy zinc phthalocyanine (n-BuO)4ZnPc has been synthesized in a single step, starting from commercial precursors, and easily purified. The molecule can be solution processed to form an effective and inexpensive hole transport layer for organic and perovskite solar cells. These appealing features are suggested by the results of a series of chemical, optical, and voltammetric characterizations of the molecule, supported by the results of ab initio simulations. Preliminary measurements of (n-BuO)4ZnPc-methylammonium lead triiodide perovskite-based devices confirm such suggestion and indicate that the interface between the photoactive layer and the hole transporting layer is characterized by hole-extracting and electron-blocking properties, potentially competitive with those of other standards de facto in the field of organic hole transport materials, like the expensive Spiro-OMeTAD.

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Towards efficient and stable perovskite solar cells employing non-hygroscopic F4-TCNQ doped TFB as the hole-transporting material

Nanoscale ◽

10.1039/c9nr05719f ◽

2019 ◽

Vol 11 (41) ◽

pp. 19586-19594 ◽

Cited By ~ 7

Author(s):

Hannah Kwon ◽

Ju Won Lim ◽

Jinyoung Han ◽

Li Na Quan ◽

Dawoon Kim ◽

...

Keyword(s):

Solar Cells ◽

Perovskite Solar Cells ◽

Hole Transport ◽

Transport Layer ◽

Hole Transport Layer ◽

Inorganic Perovskite ◽

Hole Transporting ◽

Hole Transporting Material

Designing an efficient and stable hole transport layer (HTL) material is one of the essential ways to improve the performance of organic–inorganic perovskite solar cells (PSCs).

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Spiro-OMeTAD single crystals: Remarkably enhanced charge-carrier transport via mesoscale ordering

Science Advances ◽

10.1126/sciadv.1501491 ◽

2016 ◽

Vol 2 (4) ◽

pp. e1501491 ◽

Cited By ~ 66

Author(s):

Dong Shi ◽

Xiang Qin ◽

Yuan Li ◽

Yao He ◽

Cheng Zhong ◽

...

Keyword(s):

Crystal Structure ◽

Solar Cells ◽

Charge Carrier ◽

Single Crystals ◽

Carrier Transport ◽

Dye Sensitized Solar Cells ◽

Hole Transport ◽

Transport Pathways ◽

Hole Transporting ◽

Hole Transporting Material

We report the crystal structure and hole-transport mechanism in spiro-OMeTAD [2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenyl-amine)9,9′-spirobifluorene], the dominant hole-transporting material in perovskite and solid-state dye-sensitized solar cells. Despite spiro-OMeTAD’s paramount role in such devices, its crystal structure was unknown because of highly disordered solution-processed films; the hole-transport pathways remained ill-defined and the charge carrier mobilities were low, posing a major bottleneck for advancing cell efficiencies. We devised an antisolvent crystallization strategy to grow single crystals of spiro-OMeTAD, which allowed us to experimentally elucidate its molecular packing and transport properties. Electronic structure calculations enabled us to map spiro-OMeTAD’s intermolecular charge-hopping pathways. Promisingly, single-crystal mobilities were found to exceed their thin-film counterparts by three orders of magnitude. Our findings underscore mesoscale ordering as a key strategy to achieving breakthroughs in hole-transport material engineering of solar cells.

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Novel Anthracene HTM Containing TIPs for Perovskite Solar Cells

Processes ◽

10.3390/pr9122249 ◽

2021 ◽

Vol 9 (12) ◽

pp. 2249

Author(s):

Sanghyun Paek

Keyword(s):

Solar Cells ◽

High Performance ◽

Perovskite Solar Cells ◽

Hole Transport ◽

Long Term Stability ◽

Photovoltaic Conversion Efficiency ◽

Hole Transporting ◽

Hole Transporting Material ◽

Hole Transporting Materials

Recently, perovskite solar cells have been in the spotlight due to several of their advantages. Among the components of PSCs, hole transporting materials (HTMs) re the most important factors for achieving high performance and a stable device. Here, we introduce a new D–π–D type hole transporting material incorporating Tips-anthracene as a π–conjugation part and dimethoxy-triphenylamine as a donor part (which can be easily synthesized using commercially available materials). Through the measurement of various optical properties, the new HTM not only has an appropriate energy level but also has excellent hole transport capability. The device with PEH-16 has a photovoltaic conversion efficiency of 17.1% under standard one sun illumination with negligible hysteresis, which can be compared to a device using Spiro_OMeTAD under the same conditions. Ambient stability for 1200 h shown that 98% of PEH-16 device from the initial PCE was retained, indicating that the devices had good long-term stability.

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Soluble hexamethyl-substituted subphthalocyanine as a dopant-free hole transport material for planar perovskite solar cells

Royal Society Open Science ◽

10.1098/rsos.180617 ◽

2018 ◽

Vol 5 (8) ◽

pp. 180617 ◽

Cited By ~ 5

Author(s):

Feng Wang ◽

Xiaoyuan Liu ◽

Ehsan Rezaee ◽

Haiquan Shan ◽

Yuxia Zhou ◽

...

Keyword(s):

Solar Cells ◽

Perovskite Solar Cells ◽

Chemical Properties ◽

Hole Transport ◽

Orbital Energy ◽

Step Method ◽

Free Hole ◽

Hole Transporting ◽

Hole Transporting Material ◽

Physical And Chemical

Boron subphthalocyanine (SubPc) has special physical and chemical properties, originating from its non-centrosymmetric, near-planar taper structure and large conjugated system; it can act as an alternative to the small molecule hole-transporting material 2,2′,7,7′-tetrakis-( N , N -di- p -methoxyphenylamine)-9,9′-spirobifluorene in perovskite solar cells (PSCs). To achieve a higher solubility in common organic solvents and a more suitable highest occupied molecular orbital energy level that aligns with the valence band of the perovskite material, a SubPc molecule with a hexamethyl substitution at its peripheral position (Me 6 -SubPc) was successfully designed and synthesized in a one-step method. Completely solution processed PSCs were fabricated with only a small hysteresis, a power conversion efficiency of 6.96% and V oc of 0.986 V.

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Nickel phthalocyanine as an excellent hole-transport material in inverted planar perovskite solar cells

Chemical Communications ◽

10.1039/c9cc01266d ◽

2019 ◽

Vol 55 (37) ◽

pp. 5343-5346 ◽

Cited By ~ 11

Author(s):

Mustafa Haider ◽

Chao Zhen ◽

Tingting Wu ◽

Jinbo Wu ◽

Chunxu Jia ◽

...

Keyword(s):

Solar Cells ◽

Power Conversion Efficiency ◽

Conversion Efficiency ◽

Power Conversion ◽

Perovskite Solar Cells ◽

Hole Transport ◽

Nickel Phthalocyanine ◽

Hole Transporting ◽

Hole Transporting Material

Nickel phthalocyanine as a hole transporting material in inverted planar perovskite solar cells leads to a power conversion efficiency of 14.3%.

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Organic Light-Emitting Diodes Using Triphenylamine Based Hole Transporting Materials

MRS Proceedings ◽

10.1557/proc-621-q3.4.1 ◽

2000 ◽

Vol 621 ◽

Cited By ~ 14

Author(s):

Hisayoshi Fujikawa ◽

Masahiko Ishii ◽

Shizuo Tokito ◽

Yasunori Taga

Keyword(s):

Thermal Stability ◽

Light Emission ◽

Light Emitting Diode ◽

Hole Transport ◽

Transport Layer ◽

Hole Transport Layer ◽

Light Emitting ◽

Hole Transporting ◽

Hole Transporting Material ◽

Increasing Temperature

ABSTRACTThe durability of the tris(8-quinolinolato) aluminum based light-emitting diode (LED) is related to the thermal stability of the hole transport layer. Several linear linkage triphenylamine oligomers were used for the hole transport layer. The thermal stability was clearly seen to depend on a glass transition temperature (Tg) of the hole transporting material, and a linear relationship between the Tg and the thermal stability was found. A lowering of “turn-on voltage” for light emission and an increase of luminous efficiency with increasing temperature was also observed. Excellent durability of the organic LED with a tetramer of triphenylamine was achieved at a high temperature of 120°C. Our results indicate that the linear linkage of triphenylamine leads to a high Tg and high device performance at high temperatures.

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Spiro-tBuBED: a new derivative of a spirobifluorene-based hole-transporting material for efficient perovskite solar cells

Journal of Materials Chemistry A ◽

10.1039/c8ta12274a ◽

2019 ◽

Vol 7 (11) ◽

pp. 5934-5937 ◽

Cited By ~ 2

Author(s):

Po-Han Lin ◽

Kun-Mu Lee ◽

Chang-Chieh Ting ◽

Ching-Yuan Liu

Keyword(s):

Solar Cells ◽

Oxidation Process ◽

Perovskite Solar Cells ◽

Hole Transport ◽

Transport Layer ◽

Hole Transport Layer ◽

Hole Transporting ◽

Hole Transporting Material

Perovskite solar cells using a new spirobifluorene core-based oligoaryl as the hole-transport layer display 18.6% efficiency without any device oxidation process.

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Spectroelectrochemical Study of the Formation of Radical cations of 4,4’-bis[N-(1-naphthyl)-N-phenyl-amino]-biphenyl as a Hole Transport Semiconductor Material

MRS Proceedings ◽

10.1557/opl.2011.7 ◽

2011 ◽

Vol 1286 ◽

Cited By ~ 2

Author(s):

Sharavsambuu Baasanjav ◽

Gendensvren Bolormaa ◽

Batjargal Naranbileg ◽

Munkhbat Battulga ◽

Chimed Ganzorig

Keyword(s):

Radical Cations ◽

Band Gap Energy ◽

Hole Transport ◽

Emission Region ◽

Light Emitting ◽

Light Emitting Devices ◽

Quenching Process ◽

Hole Transporting ◽

Uv Visible ◽

Hole Transporting Material

ABSTRACTSpectroelectrochemical study on a new absorption band of radical cations of 4,4’-bis[N-(1-naphthyl)-N-phenyl-amino]-biphenyl (α-NPD) as an electron-donor hole-transporting material used in organic electronics is reported in this work. UV-visible spectroscopic and cyclic voltammetric properties for α-NPD in solution are also examined. We find that the results are attributed to quenching process for blue fluorescence from α-NPD by excess α-NPD+ radical cations accumulated in the emission region in the organic light-emitting devices related to a relatively large overlap between the fluorescence spectrum of α-NPD and the absorption spectrum of α-NPD+ radical cations. The band gap energy for α-NPD is calculated from the UV-visible spectroscopic data.

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New materials for Organic Light-Emitting Diodes

MRS Proceedings ◽

10.1557/proc-413-55 ◽

1995 ◽

Vol 413 ◽

Author(s):

S. Joshua Jacobs ◽

Timothy P. Pollagi ◽

Michael B. Sinclair ◽

Rodger D. Scurlock ◽

Peter R. Ogilby

Keyword(s):

Light Emitting Diodes ◽

Hole Transport ◽

Organic Light Emitting Diodes ◽

New Materials ◽

Light Emitting ◽

Double Heterostructure ◽

Organic Light ◽

Hole Transporting ◽

Hole Transporting Material

ABSTRACTWe have investigated the performance of a class of heterocycles, 5,10-dihetera- 5,10-dihydroindeno[3,2b]indenes, as hole transport agents in simple double heterostructure organic light-emitting diodes with tris(8-hydroxyquinoline)aluminum (Alq). The best of these materials, 5,10-dihydroindolo[3,2b]indole, yields devices with luminance and lifetimes comparable to those obtained using N,N′-di-(3-methylphenyl)-N,N′- diphenyl-4,4′-diaminobiphenyl (TPD) as a hole transporting material.

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