Investigation of C60F36 as low-volatility <i>p</i>-dopant in organic optoelectronic devices

Meerheim, Rico; Olthof, Selina; Hermenau, Martin; Scholz, Sebastian; Petrich, Annette; Tessler, Nir; Solomeshch, Olga; Lüssem, Björn; Riede, Moritz; Leo, Karl

doi:10.1063/1.3590142

Cited by 55 publications

(50 citation statements)

References 25 publications

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“…In turn, however, the low vapor pressure and potential desorption of (typically small) molecular dopants like F 4 TCNQ [134][135][136] and, in particular, their diffusion through layered structures represents an important issue that has been repeatedly addressed in literature [48,65] A c c e p t e d M a n u s c r i p t 25 stability of the systems cannot be fully assured and interfacial effects between substrate and dopant can mimic doping related energy-level shifts [48].…”

Section: Molecularly Doped Cpsmentioning

confidence: 99%

Toward a comprehensive understanding of molecular doping organic semiconductors (review)

Salzmann

Heimel

2015

Journal of Electron Spectroscopy and Related Phenomena

122

137

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Section: Molecularly Doped Cpsmentioning

confidence: 99%

Toward a comprehensive understanding of molecular doping organic semiconductors (review)

Salzmann

Heimel

2015

Journal of Electron Spectroscopy and Related Phenomena

122

137

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“…The smaller F4TCNQ is known to diffuse against a concentration gradient and thereby to dope regions of the sample outside of the originally intended area, thus reducing device lifetimes. 35 In addition, since the diestersubstituted dopants do not dimerize until after deposition, they can be efficiently mixed into the polymer and then doping can occur post film formation through the dimerization reaction. The dopants, once dimerized, will provide a much higher barrier to diffusion.…”

Section: Conductivitymentioning

confidence: 99%

Introducing Solubility Control for Improved Organic P-Type Dopants

et al. 2015

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To overcome the poor solubility of the widely 8 used p-type dopant 2, 3,5,6-tetrafluoro-7,7,8,8-tetracyanoqui-9 nodimethane (F4TCNQ) 31,32 and 3,6-difluoro-2,5,7,7,8,8-75 In this paper, we first demonstrate a straightforward synthetic 88 route to soluble versions of F4TCNQ-type dopants by 89 substituting the cyano groups with either methyl or n-octyl f1 90 esters (Figure 1). A comprehensive study of the electro-91 chemical properties of these F4TCNQ analogues is performed 92 using cyclic voltammetry. With a combination of optical 93 absorption spectroscopy, photoluminescence spectroscopy, and 94 conductivity measurements, we not only demonstrate the p-95 type doping of P3HT using these new dopants, but also show 96 that comparable doping efficiency can be achieved even with 97 slightly reduced electron affinity. These novel molecular 98 dopants establish that the introduction of solubility control is 99 a successful strategy to tailor the properties of organic p-type 100 dopants. 101 ■ EXPERIMENTAL SECTION 102Materials. 1,4-Bis(chloromethyl)-2,3,5,6-tetrafluorobenzene was 103 purchased from Oakwood Products. Sodium hydride (60% dispersion 104 in mineral oil) was purchased from Alfa Aesar. Bromine, 105 perfluorobenzene, potassium carbonate, dimethyl carbonate, malono-106 nitrile, sodium acetate, sodium hydroxide, and phosphorus tribromide 107 were purchased from Sigma-Aldrich. Anhydrous dimethyl sulfoxide 108 (DMSO) and dimethylformamide (DMF) were purchased from Acros 109 Organics. Hydrochloric acid (37% aqueous), p-toluenesulfonic acid 110 monohydrate, ethanol, tetrahydrofuran (THF), dichloromethane 111 (DCM), ethyl acetate, toluene, and hexane were purchased from 112 Fisher Scientific. Acetic acid and sodium cyanide were purchased from 113 Fluka. Octanol was purchased from EM Science. Trifluoroacetic acid 114 (TFA) and acetic anhydride were purchased from EMD. P3HT 115 (Regioregular >98%, M n = 54−75 kDa, HOMO 5 eV and LUMO 3 116 eV) was purchased from Sigma-Aldrich. F4TCNQ (>98%) was 117 purchased from TCI. All chemicals were used as received unless 118 otherwise indicated. All solvents were dried over molecular sieves (3 119 Å) before use. 120Characterization.

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“…[15][16][17] We investigate the influence of doping concentration on the operation voltage and efficiency of red and green phosphorescent OLEDs. We find that BF-DPB and NPB based OLEDs exhibit significantly steeper J-V curves than devices based on the other two HTLs and thus achieve excellent luminous efficacy.…”

Section: -14mentioning

confidence: 99%

Alternative p-doped hole transport material for low operating voltage and high efficiency organic light-emitting diodes

Murawski

Fuchs

Hofmann

et al. 2014

Applied Physics Letters

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We investigate the properties of N,N′-[(Diphenyl-N,N′-bis)9,9,-dimethyl-fluoren-2-yl]-benzidine (BF-DPB) as hole transport material (HTL) in organic light-emitting diodes (OLEDs) and compare BF-DPB to the commonly used HTLs N,N,N′,N′-tetrakis(4-methoxyphenyl)-benzidine (MeO-TPD), 2,2′,7,7′-tetrakis(N,N′-di-p-methylphenylamino)-9,9′-spirobifluorene (Spiro-TTB), and N,N′-di(naphtalene-1-yl)-N,N′-diphenylbenzidine (NPB). The influence of 2,2′-(perfluoronaphthalene-2,6-diylidene)dimalononitrile (F6-TCNNQ p-dopant) concentration in BF-DPB on the operation voltage and efficiency of red and green phosphorescent OLEDs is studied; best results are achieved at 4 wt. % doping. Without any light extraction structure, BF-DPB based red (green) OLEDs achieve a luminous efficacy of 35 .1 lm/W (74 .0 lm/W) at 1000 cd/m2 and reach a very high brightness of 10 000 cd/m2 at a very low voltage of 3.2 V (3.1 V). We attribute this exceptionally low driving voltage to the high ionization potential of BF-DPB which enables more efficient hole injection from BF-DPB to the adjacent electron blocking layer. The high efficiency and low driving voltage lead to a significantly lower luminous efficacy roll-off compared to the other compounds and render BF-DPB an excellent HTL material for highly efficient OLEDs.

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Investigation of C60F36 as low-volatility p-dopant in organic optoelectronic devices

Cited by 55 publications

References 25 publications

Toward a comprehensive understanding of molecular doping organic semiconductors (review)

Toward a comprehensive understanding of molecular doping organic semiconductors (review)

Introducing Solubility Control for Improved Organic P-Type Dopants

Alternative p-doped hole transport material for low operating voltage and high efficiency organic light-emitting diodes

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