Fluorinated Copper(I) Carboxylates as Advanced Tunable p‐Dopants for Organic Light‐Emitting Diodes

Schmid, Günter; Wemken, Jan Hauke; Maltenberger, Anna; Diez, Carola; Jaeger, A.; Dobbertin, T.; Hietsoi, Oleksandr; Dubceac, Cristina; Petrukhina, Marina A.

doi:10.1002/adma.201303252

Cited by 22 publications

(23 citation statements)

References 31 publications

(26 reference statements)

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“…[1][2][3][4][5][6][7] Superseding the early concepts of doping of semiconducting polymers with halogen vapors, a reasonably stable p-type doping wileyonlinelibrary.com studied the optical and charge carrier transport properties of various Lewis basic conjugated molecules and polymers which were doped by the strong Lewis acid tris(pentafl uorophenyl)borane (BCF). [ 31 ] The doping has been explained in terms of the formation of Lewis acid-base adducts. [26][27][28]30 ] BCF-doping of a copolymer of dithienosilole and pyridine units (DTS-Py) led to both changes of the polymer's optical properties and an increase of the free charge carrier concentration and mobility.…”

Section: Introductionmentioning

confidence: 99%

p‐Type Doping of Poly(3‐hexylthiophene) with the Strong Lewis Acid Tris(pentafluorophenyl)borane

Pingel

Arvind

Kölln

et al. 2016

Adv Elect Materials

155

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State-of-the-art p-type doping of organic semiconductors is usually achieved by employing strong π-electron acceptors, a prominent example being tetrafl uorotetracyanoquinodimethane (F 4 TCNQ). Here, doping of the semiconducting model polymer poly(3-hexylthiophene), P3HT, using the strong Lewis acid tris(pentafl uorophenyl)borane (BCF) as a dopant, is investigated by admittance, conductivity, and electron paramagnetic resonance measurements. The electrical characteristics of BCF-and F 4 TCNQ-doped P3HT layers are shown to be very similar in terms of the mobile hole density and the doping effi ciency. Roughly 18% of the employed dopants create mobile holes in either F 4 TCNQ-or BCF-doped P3HT, while the majority of doping-induced holes remain strongly Coulomb-bound to the dopant anions. Despite similar hole densities, conductivity and hole mobility are higher in BCF-doped P3HT layers than in F 4 TCNQ-doped samples. This and the good solubility in many organic solvents render BCF very useful for p-type doping of organic semiconductors.

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Section: Introductionmentioning

confidence: 99%

p‐Type Doping of Poly(3‐hexylthiophene) with the Strong Lewis Acid Tris(pentafluorophenyl)borane

Pingel

Arvind

Kölln

et al. 2016

Adv Elect Materials

155

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“…This represents ar are example of as tepwise controlled chain growth in extended metal atom chains (EMACs). [6] Recently,t heoretical studies indicated that multicopper coordination to DNAb ase pairs may improve the conductivity of DNA-based nanowires. [1] Furthermore,o ne-dimensional (1D) assemblies of transition-metal complexes ("molecular wires") are of high interest for molecular microelectronics applications and studying processes of electron transfer in metal chains.…”

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confidence: 99%

“…[1] Furthermore,o ne-dimensional (1D) assemblies of transition-metal complexes ("molecular wires") are of high interest for molecular microelectronics applications and studying processes of electron transfer in metal chains. [6] Recently,t heoretical studies indicated that multicopper coordination to DNAb ase pairs may improve the conductivity of DNA-based nanowires. [2b, 3] In addition, Cu I "wires" and clusters of various nuclearities have been shown to have interesting photophysical properties that render them suitable for optoelectronic applications.…”

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confidence: 99%

“…[2b, 3] In addition, Cu I "wires" and clusters of various nuclearities have been shown to have interesting photophysical properties that render them suitable for optoelectronic applications. [6] Recently,t heoretical studies indicated that multicopper coordination to DNAb ase pairs may improve the conductivity of DNA-based nanowires. [6] Recently,t heoretical studies indicated that multicopper coordination to DNAb ase pairs may improve the conductivity of DNA-based nanowires.…”

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confidence: 99%

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Controlled and Reversible Stepwise Growth of Linear Copper(I) Chains Enabled by Dynamic Ligand Scaffolds

et al. 2017

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Reversible stepwise chain growth in linear Cu I assemblies can be achieved by using the dynamic,unsymmetric naphthyridinone-based ligand scaffolds L1 and L2.W ith the same ligand scaffolds,the length of the linear copper chain can be varied from two to three and four copper atoms,a nd the nuclearity of the complex is easily controlled by the stepwise addition of aC u I precursor to gradually increase the chain length, or by the reductive removal of Cu atoms to decrease the chain length. This represents ar are example of as tepwise controlled chain growth in extended metal atom chains (EMACs). All complexes are formed with excellent selectivity, and the mutual transformations of the complexes of different nuclearity were found to be fast and reversible.These unusual rearrangements of metal chains of different nuclearities were achieved by as tepwise "sliding" movement of the naphthyridinone bridging fragment along the metal chain.Linear-chain multimetallic complexes remain an active area of research owing to their applications as supramolecular building blocks and their ability to undergo multiple electron transfer steps,w hich play an important role in catalysis and small-molecule activation. [1] Furthermore,o ne-dimensional (1D) assemblies of transition-metal complexes ("molecular wires") are of high interest for molecular microelectronics applications and studying processes of electron transfer in metal chains. [2] Multinuclear Cu complexes were among the first structurally characterized and studied extended metal atom chain (EMAC) compounds. [2b, 3] In addition, Cu I "wires" and clusters of various nuclearities have been shown to have interesting photophysical properties that render them suitable for optoelectronic applications. [4] Cu I polynuclear species have also been utilized as precursors in the synthesis of metalrich materials in microelectronics [5] and as tunable dopants in OLEDs. [6] Recently,t heoretical studies indicated that multicopper coordination to DNAb ase pairs may improve the conductivity of DNA-based nanowires. [7] Then uclearity of such complexes has as ignificant effect on their properties,a nd therefore,f ine control over the selective formation of solution-stable polynuclear metal chains of defined lengths and geometry is needed, especially in the case of labile complexes of late first-row transition metals such as Cu I . [8] Although polymetallic Cu I clusters of different nuclearities could be formed with simple bridging ligands such as carboxylates,t he geometry of these complexes has been difficult to predict and their stability has been mostly limited to the solid state. [8a] Another method that provides better control over the geometry and nuclearity of 1D multimetallic chains is the direct combination of polynucleating multidentate ligands (e.g.,o ligo-a-pyridylamides) with am etal precursor to yield EMACc omplexes in ao ne-step process (see Scheme 1f or some examples). [2b,9] In this case,s ymmetric polynucleating ligand scaffolds that can bind ap redefined number of me...

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“…These findings are in agreement with our hypothesis that the doping effect increases with increasing acidity of a Lewis-acid. 18 In principle, the doping behavior of fluorinated copper acetylacetonate compounds can be explained by two mechanisms. First, copper in the oxidation state two can act as classical oxidant or electron acceptor and thus dope by electron transfer from the HOMO of the HTL to the LUMO of the dopant.…”

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confidence: 99%

Low-cost copper complexes as p-dopants in solution processable hole transport layers

Kellermann

Taroata

Maltenberger

et al. 2015

Applied Physics Letters

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We demonstrate the usage of the Lewis-acidic copper(II)hexafluoroacetylacetonate (Cu(hfac)2) and copper(II)trifluoroacetylacetonate (Cu(tfac)2) as low-cost p-dopants for conductivity enhancement of solution processable hole transport layers based on small molecules in organic light emitting diodes (OLEDs). The materials were clearly soluble in mixtures of environmentally friendly anisole and xylene and spin-coated under ambient atmosphere. Enhancements of two and four orders of magnitude, reaching 4.0 × 10−11 S/cm with a dopant concentration of only 2 mol% Cu(hfac)2 and 1.5 × 10−9 S/cm with 5 mol% Cu(tfac)2 in 2,2′,7,7′-tetra(N,N-ditolyl)amino-9,9-spiro-bifluorene (spiro-TTB), respectively, were achieved. Red light emitting diodes were fabricated with reduced driving voltages and enhanced current and power efficiencies (8.6 lm/W with Cu(hfac)2 and 5.6 lm/W with Cu(tfac)2) compared to the OLED with undoped spiro-TTB (3.9 lm/W). The OLED with Cu(hfac)2 doped spiro-TTB showed an over 8 times improved LT50 lifetime of 70 h at a starting luminance of 5000 cd/m2. The LT50 lifetime of the reference OLED with PEDOT:PSS was only 8 h. Both non-optimized OLEDs were operated at similar driving voltage and power efficiency.

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Fluorinated Copper(I) Carboxylates as Advanced Tunable p‐Dopants for Organic Light‐Emitting Diodes

Cited by 22 publications

References 31 publications

p‐Type Doping of Poly(3‐hexylthiophene) with the Strong Lewis Acid Tris(pentafluorophenyl)borane

p‐Type Doping of Poly(3‐hexylthiophene) with the Strong Lewis Acid Tris(pentafluorophenyl)borane

Controlled and Reversible Stepwise Growth of Linear Copper(I) Chains Enabled by Dynamic Ligand Scaffolds

Low-cost copper complexes as p-dopants in solution processable hole transport layers

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