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Home , Organic electronics, Organic semiconductor, Pentacene, Printed electronics, Tetracene

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Organic field-effect (OFETs) are promising devices. In general, the expansion and extension of π-conjugation components for the next-generation electronic devices. In 1984, is an effective strategy in the molecular design of OFET OFET research began with the first report of mobility in a and . As an example, , which consists of 5 merocyanine dye-based field-effect device by Kudo et al.1) Since fused rings, possesses superior electrical properties high hole mobility (1.5 cm2/Vs), which comparable to that of compared to that of , which consists of 4 fused benzene amorphous , was achieved using a pentacene-based OFET rings. 8) However, a linear increase in the number of fused aromatic device in 1997,2) the possibility of a practical application of OFET’s rings in a simple system raises the Highest Occupied became realistic and the research field became quite popular Molecular Orbital（HOMO), resulting in a critical decrease in the worldwide. While silicon has performed well in devices, the air-stability of the and materials. 8) This inorganic of them prohibits flexible structures. As a result, trade-off issue between the mobility and the air-stability of the OFETs have attracted much attention for their potential to be materials has been a key problem to overcome. Given this context, flexible, thin and -weight, which could be applicable for in 2006 DPh-BTBT [D3526], a thienothiophene-fused organic foldable electronic circuits and implantable biometric sensors. 3, 4) compound, had been reported by Takimiya et al., as an innovative A noted potential application with OFET’s involves their OFET material.9) DPh-BTBT features a deep HOMO level (-5.6 “printability”. Printed are an innovative technology for eV), which leads to remarkable air-stability during OFET device mass and low cost device productions, which could allow for the performance, and the HOMOs are well-distributed over the production of high density and large circuits on flexible substrates atoms of the thienothiophene moieties inducing good hole carrier such as and plastic films. A fusion of “” transport. DPh-BTBT-based FET devise further achieved excellent and “Organic transistors” could offer especially promising electrical properties with a high hole mobility of 2.0 cm2/Vs. technology by allowing for low cost and large scale manufacture of Followed by the innovation and molecular design of DPh-BTBT, various functional devices. 5-7) Ph-BTBT-10, an smectic E (SmE) liquid crystalline material, was One of the functional parameters evaluated in organic recently reported by Hanna et al., as a p-type material that bears semiconductor materials is mobility (μ), which indicates how fast an asymmetric structure in which the alkyl and the the holes (p-type) or (n-type) within the semiconducting are substituted on one side of the benzothienobenzothiophene move. A material that possesses high carrier mobility is (BTBT) moiety.10) Additionally, Ph-BTBT-10 can be handled in required for producing high-speed circuits. OFET devices are a processing such the spin-coting method, and possesses largely simple construction containing an both good heat-resistance and film-forming properties. The Ph- layer, an insulating layer, and source-drain-gate electrodes. These BTBT-10 spin-coated devise exhibited not only outstanding OFET 2 components allow for the evaluation of fundamental transistor performance with ultra-high mobility (μmax = 14.7 cm /Vs), but also parameters including mobility, operation voltage, and driving comparable to oxide (IGZO) with remarkable air- stability. stability. Source electrode

Drain electrode Tetracene Pentacene [N0951] [P2524]

S S (CH2)9CH3 S S Organic semiconductor layer DPh-BTBT DPh-BTBT-10 Gate electrode Gate [D3526] [D5491]

Top view One of the largest benefits of organic compounds for OFET’s is their immense structural variety. This variety can be used to control Source Drain the various properties they possess such as the electrical Organic semiconductor layer Channel performance, stability, and processing characteristics through the Insulator chemical modification of the molecular units. Within the organic Gate transistor research field, the possibilities for practical application Side view has dramatically improved by introducing new concepts and various materials proposals, including the unique OFET materials and the parent molecules used to create them. Due to the expanded π- within organic semiconductor molecules, these often produce large intermolecular ● High Quality Organic Semiconductor interactions inducing an improvement in the mobility within OFET Materials (For )

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TCI offers “High Quality Organic Semiconductor Materials (For Specification Compound Product No. Mobility Si/SiO Substrate Organic Electronics)” specialized for electrical performance such Purity (%) 2 (cm2/Vs) Surface Condition as OFET mobility*. A material used in the active layer of an OFET Pentacene P2524 > 99.999 > 0.35 Bare device requires exceptionally high-purity to produce good OFET Ph-BTBT-10 D5491 > 99.5 > 10.0 ODTS function. However, it is difficult to analytically (HPLC, GC, etc.) P3HT P2513 Pd: < 100ppm > 0.10 OTS TIPS B5942 > 99.0 > 0.10 HMDS determine the purity at the ultra-high levels required for OFET Pentacene function. To surmount this quality assurance challenge, we have C70 F1233 > 99.0 > 0.30 HMDS [60]PCBM P2682 > 99.5 > 0.020 HMDS begun in-house fabrication of OFET devices using our OFET [70]PCBM P2683 > 99.0 > 0.015 HMDS materials. Once fabricated, we assess the functionality of the OFET as a quality assurance measure to confirm the electronic properties and device performance of the “High Quality Organic 1. An Example of OFET Evaluation 1: Semiconductor Materials (For Organic Electronics)”. We constantly Typical p-type Material "Pentacene" seek to improve our technology and skill in order to provide high- purity and quality materials our customers. Pentacene [P2524] (*The mobility refers to device evaluation measurements obtained within our facility (99.999%, trace basis) (purified by sublimation) under environment condition.)

Results of the device test are fed buck to the synthesis and puri cation process Pentacene [P2524]

High-purity OFET Product Purification Performance Supply Synthesis Test

Pentacene, a simple polyaromatichydrocarbon, has been studied for its fundamental properties and applications in organic electronic research.11, 12) In particular, many research studies have been conducted to evaluate its potential as a carrier transporter within OFET devices.2,13) TCI provides two subliminally purified pentacene reagents: P2524 and P0030. P2524 (99.999% trace basis) is our high-quality grade reagent, which has additional 2 specifications for its OFET mobility: [> 0.35 cm /Vs (bare Si/SiO2)]. We inspect P2524 through the OFET evaluation process in every product lot. Only lots that pass this functional test are packed and shipped as “High Quality Organic Semiconductor Materials (For Organic Electronics)”.

● List of High Quality Organic 0.03 Semiconductor Materials P2524 (99.999%) P0030 (For Organic Electronics) 0.02 unsublimated S 1/2

(CH2)9CH3 /A D S - I 0.01 Pentacene Ph-BTBT-10 [P2524] [D5491]

0.00 (CH2)5CH3 CH3 CH3 CH3 CH3 CH3 CH3 0 -25 -50 -75 -100 Si C C C C Si CH3 CH3 VG / V S n CH3 CH3 CH3 CH3 P3HT Figure 1. Transfer curves of various grades of pentacene. [P2513]

n: 36,000 ～ 45,000 TIPS Pentacene RR: > 99.0% [B5942] Table 1. OFET characteristics of the .

OCH3 Mobility Vth OCH3 Product No. Sample grade Substrate (cm2/Vs) (V) O O - Pentacene Si/SiO2 -4 -13 (non-sublimation) (bare) 5.3 × 10 Pentacene Si/SiO2 P0030 (purified by sublimation) (bare) 0.29 -22 Pentacene P2524 (99.999%, trace metals basis) Si/SiO2 0.39 -10 [60]PCBM [70]PCBM C70 (purified by sublimation) (bare) [P282] [P283] [F1233]

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The performances of the pentacene-based OFET devices are Figure 3. Illustration for the device structure of pentacene-based OFET device. summarized in Table 1 and Figure 1. These devices were fabricated via vacuum deposition method on bare Si/SiO2 substrate without Self-

Assembled Monolayer (SAM) treatment, the characteristics of which Pentacene [P2524] were measured under conditions. Our sublimed pentacene

[P2524] showed a large increase OFET performance compared to Surface Treatment that of the non-sublimed pentacene. As a result, (99.999% OTS [O018] Top contact type P2524 Channel length: 50 μm trace metal basis) showed an excellent OFET performance with the Channel width: 1.5 mm Organic layer: 60 nm highest hole mobility of 0.39 cm2/Vs. In comparison to other Source, Drain : Au companies' sublimed pentacene samples, P2524 (99.999% trace (a) metal basis) possesses the highest drain current and the best OFET 0.01 0.06 V = -100 V potential (Figure 2 and Table 2). 0.001 D 0.05 0.0001 0.03 (- I -5 0.04 1x10 D V = -100 V ) D 1/2 A /

P2524 / A D 1x10-6 0.03 - I

Company A 1/2 1x10-7 Company B 0.02 0.02 Company C 1x10-8

1/2 0.01 1x10-9 / A D

- I 1x10-10 0.01 20 0 -20 -40 -60 -80 -100

VG / V (b) 0.01 0.06 V = -100 V 0 0.001 D 25 0 -25 -50 -75 -100 0.05 VG / V 0.0001 (- I -5 0.04 1x10 D )

Figure 2. Transfer curves of OFET devices using several 1/2 A / / A companies' pentacene. D -6

- I 1x10 0.03 1/2 1x10-7 0.02 1x10-8 Table 2. OFET characteristics of the pentacenes. 0.01 1x10-9 Substrate Mobility Vth (cm2/Vs) (V) 1x10-10 20 0 -20 -40 -60 -80 -100 P2524 Si/SiO2 (bare) 0.39 -10 V / V Company A (sublimed) Si/SiO2 (bare) 0.002 -25 G Company B (sublimed) Si/SiO (bare) 0.001 -25 2 (c) × -6 Company C (sublimed) Si/SiO2 (bare) 5.0 10 -23 -0.002

1-a. Optimization of pentacene-based -0.0015

OFET devices A / D I -0.001 We have examined and optimized the functional preformance of VG = -100 V pentacene-based OFET devices via substrate surface modification. -0.0005 -80 V The field-effect mobility of pentacene was measured using top- -60 V -40 V contact thin-film field-effect transistors geometry (Figure 3). The thin 0 film of pentacene [P2524] as the active layer (60 nm) was vacuum- 0 -20 -40 -60 -80 -100 VD / V deposited onto Si/SiO2 substrate (bare) or n-Octyltrichlorosilane

(OTS) [O0168] -treated Si/SiO2 substrate at room temperature (Tsub (d) -0.002 = RT). The drain and source electrodes (40 nm) were then prepared VG = -100 V by evaporation through a shadow mask on top of the pentacene -0.0015 film; the drain-source channel length (L) and width (w) were 50 μm -80 V

A / -0.001 and 1.5 mm, respectively. The characteristics of the OFET devices D I were measured under nitrogen conditions. -60 V

-0.0005 -40 V The performances of the OFET devices are summarized in Table -20 V 3 and figure 4. All pentacene -based devices exhibited pure typical 0 0 -20 -40 -60 -80 -100 p-channel field-effect transistor (FET) characteristics. The FET VD / V performance were significantly improved by the SAM treatment; Figure 4. Typical OFET characteristics of top-contact devices the OTS-treated device demonstrated the highest performance fabricated using pentacene [P2524]. 2 (a, c) bare. (b, d) OTS-treated substrate. with a hole carrier mobility of 1.52 cm /Vs and an on/off ratio of 1.5 (a, b) Transfer curves in the saturated region. × 107 (Figure 4). (c, d) Output curves at different gate voltages.

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Table 3. OFET characteristics of P2524-based devices.

Compound SAM Tsub Mobility Vth on/off 2. An Ultra-high Performance p-type (°C) (cm2/Vs) (V) Semiconductor Material "Ph-BTBT-10" Pentacene bare RT 0.35 ~ 0.37 -5.3 3.9 × 105 [P2513] OTS [O018] RT 1.50 ~ 1.52 -5.7 × 7 1.5 10 Ph-BTBT-10 (= 2-Decyl-7-phenyl[1]benzo- thieno[3,2-b][1]benzothiophene) [D5491] 1-b. AFM images and XRD analysis To clarify the pentacene morphology and conformation, S atomic force microscope (AFM) and X-ray diffraction (XRD) (CH2)9CH3 measurement were carried out (Figure 5). Regardless of either S bare or OTS-treated substrate, highly regular terrace structures Ph-BTBT-10 [D5491] were observed (Figure 5a). In addition, XRD measurements of the pentacene films showed a series of peaks assignable to (00h) reflections; and the diffraction peak at 2θ = 5.72° corresponds to a Ph-BTBT-10, an SmE liquid crystalline material, has been recently d-spacing of 15.5 Å (Figure 5b). These results demonstrated that reported by Hanna et al., as a p-type material which possesses the pentacene molecules stood nearly perpendicular to the excellent transport properties.10) Ph-BTBT-10 exhibits ultra-high 12, 13) 2 substrate (thin-film-phase) in the film form. mobility (μmax = 14.7 cm /Vs) comparable to oxide semiconductors (IGZO), and remarkable air stability. TCI has recently commercialized (a) 60 nm Ph-BTBT-10 as an ultra-high mobility and air stability p-type OFET bare OTS material, and has begun evaluation via the fabrication and performance measurement of Ph-BTBT-10-based OFET devices using vacuum deposition methods in our laboratories. The devise showed a hole carrier mobility up to 14.0 cm2/Vs. Please see below for details.

1 μm 1 μm 0 nm 2-a. Fabrication and evaluation of (001) Ph-BTBT-10-based OFET device OTS (002) bare The field-effect mobility of Ph-BTBT-10 was measured using top-

(003) contact thin-film field-effect transistors geometry (Figure 7). The (004) thin film of Ph-BTBT-10 as the active layer (40 nm) was vacuum- (005) deposited onto Si/SiO2 substrate (bare) or Octadecyltrichlorosilane

intensity (a.u.) (ODTS) [O0079]-treated Si/SiO2 substrate while heating the substrate. The drain and source electrodes (40 nm) were then prepared by gold evaporation through a shadow mask on top of

5 10 15 20 25 30 35 40 the Ph-BTBT-10 film; the drain-source channel length (L) and 2θ (degree) width (w) are 50 µm and 1.5 mm, respectively. After deposition,

Figure 5. AFM images(a). and XRD analysis(b) of pentacene filims. these devices were thermal annealed at Tsub = 120 °C for 5 min under ambient conditions, and the characteristics of the OFET In the bare device (without SAM), two weak peaks assignable to devices were measured. face-on orientation were observed (Figure 5b, black arrow), which would create the disadvantage of carrier passes parallel to the S substrate (Figure 6a). In contrast, such peaks were not observed (CH2)9CH3 in the pentacene film on the OTS-treated substrate (Figure 6b). It S Ph-BTBT-10 [D5491] is one reason why the mobility was higher in the OTS-treated Top contact type Surface Treatment OFET device. Channel length: 50 μm ODTS [O009] Channel width: 1.5 mm Organic layer: 40 nm South, Drain : Au (a) (b) Figure 7. Illustration for the device structure of Ph-BTBT-10-based OFET.

bare OTS Si Si The performances of the OFET devices are summarized in Table = pentacene molecule 4 and Figure 8. All Ph-BTBT-10-based devices exhibited pure Figure 6. Orientation images of pentacene thin film form. typical p-channel field-effect transistor (FET) characteristics. The FET mobilities were quite dependent on the thermal annealing treatment regardless of the self-assemble-monolayer (SAM)

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(Figure 8). This would be attributed to the phase transition from a (d) 0.01 0.05 monolayer to a bilayer in the thin-film form. 10) The VD = -50V device fabricated on bare substrate demonstrated good 1x10-4 0.04 performance with a hole carrier mobility of 4.86 cm2/Vs and (-/ D

-6 )

1x10 0.03 1/2 / A threshold voltage (Vth) of -8 V. Moreover, although Vth increased, / A D -/ the ODTS-treated devise showed the highest transport 1x10-8 0.02 1/2 performance with a hole carrier mobility of 14.0 cm2/Vs. 1x10-10 0.01 Table 4. OFET characteristics of the Ph-BTBT-10-based devices 1x10-12 0 Annealing Temp. Mobility Vth 30 20 10 0 -10 -20 -30 -40 -50 Compound SAM (°C) (cm2/Vs) (V) VG / V w/o 0.87 ~ 0.91 -24 bare Ph-BTBT-10 120 4.24 ~ 4.86 -8 Figure 8. Transfer curves of the Ph-BTBT-10-based OFET devices. [D5491] ODTS w/o 1.40 ~ 1.42 -23 (a) w/o annealing (bare) (b) annealing 120°C, 5min (bare) [O0079] 120 10.3 ~ 14.0 -22 (c) w/o annealing (ODTS) (d) annealing 120°C, 5min (ODTS)

2-b. 2D-GIXD Analysis (a) 0.01 0.05 V = -60V D (a) bare ODTS 1x10-4 0.04 180°C → RT 180°C → RT (-/ D

-6 ) 1x10 0.03 1/2 / A / A D

-/ 180°C 180°C 1x10-8 0.02 1/2

-10 1x10 0.01 120°C 120°C

1x10-12 0 20 0 -20 -40 -60 60°C 60°C VG / V

(b) 0.01 0.05 RT RT

VD = -50V 1x10-4 0.04 (-/ D

-6 )

1x10 0.03 1/2 / A / A D

-/ (b) 1x10-8 0.02 1/2 12 10

-10 11 1x10 0.01 10

10 10 1x10-12 0 9 RT 30 20 10 0 -10 -20 -30 -40 -50 10

VG / V 8 10 180℃

7 10 (c) 0.01 0.05 6 120℃

Intensity (cps) 10 VD = -60V 5 -4 1x10 0.04 10 60℃

(-/ 4 10 D

-6 )

1/2 RT 1x10 0.03 3 / A / A 10 D -/ 1/2 1x10-8 0.02 2 4 6 8

-1 qz (nm ) -10 1x10 0.01 (c)

1x10-12 0 20 0 -20 -40 -60 27 A VG / V Annealing 54 A 27 A

Figure 9. (a) 2D-GIXD analysis (Thermal in situ mesurement), (b) 2D-GIXD analysis (Out-of-plane, bare substrate), (c) Phase transition images of Ph-BTBT-10

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The crystal structures of Ph-BTBT-10 thin films were analyzed by enhancing the electrical properties of P3HT in an OFET devise. 2D-GIXD using synchrotron radiation. Figure 9 (a) and (b) display the thermal in situ 2D-GIXD data at different temperatures. The 3-a. Fabrication and Evaluation of Ph-BTBT-10 films at RT and 60°C showed a similar series of P3HT-based OFET devices peaks assignable to a monolayer structure with a d-spacing of 27 The hole mobility of P2513 was measured using top-contact OFET Å. When the substrate temperature was increased to 120°C, the geometry (Figure 10). The P3HT [P2513] was dissolved in diffraction peaks clearly changed, which suggested a :trichlorobenzene at a concentration of 10 mg/ml. The transformation from a monolayer structure (d = 27 Å) into a bilayer solution of P2513 was spin-coated (1500 RPM) onto structure with a d-spacing of 54 Å as shown in Figure 9 (c). Since n-Octyltrichlorosilane (OTS) [O0168] -treated Si/SiO2 substrate in the phase transition temperature to the SmE mesophase is 144°C, a nitrogen glove box, then thermally annealed for 30 min. A gold 10) a series of peaks assignable to SmE were observed when layer with 40 nm thickness was deposited in vacuum chamber to heated to 180°C. In addition, a mixed layer of monolayer and serve as drain and source electrodes through a shadow mask on bilayer structures appeared when the Ph-BTBT-10 thin film was top of the P2513 film; the drain-source channel length (L) and rapidly cooled from 180°C to RT. These results indicate that under width (W) are 50 μm and 1.5 mm, respectively. The characteristics these conditions the cooling speed might be a significant factor in of the OFET devices were measured under nitrogen conditions. forming a well-uniformed crystalline thin film structure. Based on The other five P3HTs were also evaluated under the same these results, Ph-BTBT-10 can be handled through vacuum protocol. deposition method, and the phase transition from the monolayer to the bilayer structure can occur in the same way in which it occurs C6H13 C6H13 10) S S for solution processed Ph-BTBT-10 thin films. Finally, we S S n demonstrated top-ranked FET performances via vacuum C6H13 C6H13 P3HT [P2513] deposition process using our in-house equipment.

Surface Treatment 3. Performance Evaluation of Highly OTS [O018] Top contact type Channel length: 50 μm Regioregular “P3HT” Channel width: 1.5 mm Source, Drain : Au

P3HT Figure 10. Illustration for the device structure of P3HT-based OFET. (= Poly(3-hexylthiophene-2,5-diyl)) (regioregular) [P2513] 3-b. A correlation between the hole transport mobility and the molecular weight18)

(CH2)5CH3 The device performances of P2513 (high molecular weight Mn: 40K) and the other three P3HT samples having low molecular weights (Mn: 8K~28K), are summarized in Figure 11 and Table 5. S n Samples 1 and 2 were synthesized via the same DArP method P3HT same as with P2513. [P2513] The OFET performances of P3HT-based devices were improved by increasing the molecular weights of P3HT. In the case of P2513, TCI’s P3HT (Poly(3-hexylthiophene-2,5-diyl)) [P2513] features a the device achieved the highest transport performance with a hole very high regioregularity (RR > 99%), a narrow molecular weight mobility of 0.1 cm2/Vs and an on/off ratio of 9×104. The high distribution (Mn = 36k ~ 45k), and a low metal content ratio (Pd < molecular weight could enhance a crystallinity of P3HT in the film 100 ppm) in order to provide high quality solution-processed form, that could be a reason why P2513 possesses the excellent organic materials for organic electronics. The synthesis was performances of OFET. The molecular weight of P2513 was set conducted via the direct aryration polymerization (DArP) method 30K ~ 45K as a specification. in collaboration with Prof. Fumiyuki Ozawa at Institute for Chemical Research, Kyoto University.14, 15) Table 5. Properties of P3HTs and mobility of OFET devices.

RR Mobility M We fabricated organic thin-film transistor (OFET) devices to (%) n (x 10 -2 cm2/Vs) validate and demonstrate hole transport properties of P3HTs. By P2513 99 40K 10.5±0.4 comparing OFET characteristics of six P3HT samples including Sample 1 99 18K 5.9±0.3 P2513, we revealed a correlation between OFET performances Sample 2 99 8K 3.0±0.4 and (1) molecular weights and (2) regioregularities of P3HTs. As Sample 3 98 28K 6.5±0.7 the result, the P2513 devise showed the highest hole mobility, Sample 4 91 39K 1.2±0.1 among the other P3HT devices. This suggested that the carrier Sample 5 93 - 1.7±0.3 transport property of P3HT was improved by both the regioregularity and the molecular weight of parameters. In particular, the regioregularity could be considered the most significant factor for

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(a) 1.2E-02 (b) P3HT[P2513] M : 40K n P3HT[P2513] 1.0E-02 Reverse RR: 99% Sample1 Mn: 18K 1E-01 Reverse 8.0E-03 -1 s 1/2

Sample2 M : 8K -1

/ A / n V 2 1/2

) 6.0E-03 Reverse D

(- I Sample3 M : 28K n μ / cm 4.0E-03 Reverse RR: 93% 2.0E-03 RR: 91%

0.0E+00 1E-02 20 0 -20 -40 -60 -80 -100 VG / V Figure 12. (A) Transfer curves of P3HT-based devices differ (b) from regioregularity of P3HT, (b) A correlation between the hole transport mobility and the regioregularity. P3HT[P2513] 1E-01 -1 s -1 V 2 μ / cm

1E-02 0 20,000 40,000 Acknowledgments Mn.

A part of atomic force microscope (AFM: SPM-9700) was conducted at the AIST Nano-Processing Facility, supported by "Nanotechnology Platform Program" of Figure 11. (a) Transfer curves of P3HT-based devices differ from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), molecular weight of P3HT, (b) A correlation between the hole Japan. Portions of the X-ray diffraction (XRD: Smart Lab) was conducted at transport mobility and the molecular weight. Advanced Characterization Nanotechnology Platform of the University of Tokyo, supported by "Nanotechnology Platform" of the Ministry of Education, Culture, 3-c. A correlation between the hole transport Sports, Science and Technology (MEXT), Japan. 2D-GIXD experiments were 19) mobility and the regioregularity performed at the BL46XU and BL19B2 of SPring-8 with the approval of the Japan The device performances of P2513 (the high regioregularity Synchrotron Radiation Research Institute (JASRI) (Proposal No. 2017B1817 and 2017B1629). We acknowledge Prof. Noriyuki Yoshimoto, Assist. Prof. Daiki >99%) and the other two P3HT samples having low regioregularities Kuzuhara and Mr. Shimpei Miura (Iwate Univ.), Assist. Prof. Mitsuharu Suzuki (91, 93%) are summarized in Figure 12 and Table 5. Samples 4 (NAIST) and Dr. Tomoyuki Koganezawa (JASRI) for technical support in GIXD. and 5 indicate other companies' P3HT. The OFET performances of P3HT-based devices were drastically improved with increasing the regioregularities within P3HTs. While sample 4 (RR: 91%, Mn: 39K) displayed a high molecular weight as P2513 (Mn: 40K), the hole transport mobility of the sample 4-based device was lower than that of the sample 2 (RR: 99%, Mn: 8K) -based device. From these results, the OFET performances of P3HT could be enhanced by the regioregularity rather than the molecular weight of P3HT.

(a) 1.2E-02 P3HT[P2513] RR: 99%

1.0E-02 Reverse

Sample4 RR: 91% 8.0E-03 1/2

/ A / Reverse 1/2

) 6.0E-03 D Sample5 RR: 93% (- I

4.0E-03 Reverse

2.0E-03

0.0E+00 20 0 -20 -40 -60 -80 -100

VG / V

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Fundamental properties of Organic Transistor Materials

UV-vis absorption spectra (using in-house equipment)

Vapor-deposited film Vapor-deposited film Vapor-deposited film 1.0 1.0 1.0 on on on i i i orp t orp t orp t b s b s b s a a a d d d 0.5 0.5 0.5 e e e Tetracene li z li z li z Pentacene [N0951] DPh- orm a orm a orm a N N N [P2524] [D5152] 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 Wavelength (nm) Wavelength (nm) Wavelength (nm)

Vapor-deposited film Vapor-deposited film Spin-coated film 1.0 1.0 1.0 on on on i i i orp t orp t orp t b s b s b s a a a d d d 0.5 0.5 0.5 e e e li z li z li z Si Si Rubrene TIPS-Pentacene orm a orm a orm a 6,13-Diphenylpentacene [T2233] N N N [D4469] [B5942] 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 Wavelength (nm) Wavelength (nm) Wavelength (nm)

CH2Cl2 solution CH2Cl2 solution Vapor-deposited film 1.0 1.0 1.0 on on on i i i orp t orp t orp t S b s b s b s a a a S d d 0.5 d 0.5 0.5 e e e li z li z li z PDT DPh-BTBT [P2207] [P2383] [D3526] orm a orm a orm a N N N 0.0 0.0 0.0 250 350 450 550 650 750 250 350 450 550 650 750 300 400 500 600 700 800 Wavelength (nm) Wavelength (nm) Wavelength (nm)

Vapor-deposited film Spin-coated film Spin-coated film Annealing 1.0 1.0 (D5153:PS = 2:1) 1.0 (D5154:PS = 2:1) on on on i i i O O orp t orp t orp t S N N b s b s b s C10H21 O O a a a S S S d d d 0.5 0.5 0.5 e e e li z li z li z Ph-BTBT-10 S S [D5491] endo-DNTT-PMI exo-DNTT-PMI orm a orm a orm a N N N [D5153] [D5154] 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 Wavelength (nm) Wavelength (nm) Wavelength (nm)

Vapor-deposited film Vapor-deposited film Vapor-deposited film 1.0 S 1.0 1.0 on on H C CH on H C CH i i 3 3 i 3 3 S S S orp t orp t anti-DMADT orp t syn-DMADT S S b s b s b s a a a S S d d [D4617] d [D4618] 0.5 0.5 0.5 e e e li z li z li z DBTTT [D5086] orm a orm a orm a N N N 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 Wavelength (nm) Wavelength (nm) Wavelength (nm)

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Vapor-deposited film Vapor-deposited film Vapor-deposited film 1.0 1.0 1.0 on on on i i i orp t orp t orp t S S S S S s s s a a a S S S S S d d d 0.5 0.5 0.5 e e e li li li α-4T α-6T -6P [Q0078] [S0504] [S0220] orm a orm a orm a 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 aelengt nm aelengt nm aelengt nm

Vapor-deposited film Vapor-deposited film Vapor-deposited film 1.0 1.0 1.0 on on on i i i orp t orp t orp t S S S S S S s C6H13 H s C8H17 C H s C10H21 H a S S C6 13 a S S 8 17 a S S C10 21 d d d 0.5 0.5 0.5 e e e li li li C6-4T C8-4T C10-4T [D4842] [D4877] [D4888] orm a orm a orm a 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 aelemgt nm aelengt nm aelengt nm

Vapor-deposited film Vapor-deposited film Spin-coated film C6H13 C6H13 S S 1.0 1.0 1.0 S S n on on on i i i C6H13 C6H13 orp t orp t orp t P3HT S S s s C12H25 H s a a S S C12 25 a [P2513] d d 0.5 0.5 d 0.5 e e e li li C12-4T BP1T li [D4889] [B3441] orm a orm a orm a 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 aelengt nm aelengt nm aelengt nm

1.5 Vapor-deposited film Vapor-deposited film 1.5 Vapor-deposited film

on 1.0 on on

i i i H

orp t orp t 1.0 orp t Cu 1.0 Zn H s s s a a a

d d d

e 0.5 e e

li H Pc li 0.5 li 2 CuPc 0.5 ZnPc [P1795] orm a orm a [P1628] orm a [Z0037] 0.0 0.0 0.0 300 400 500 600 700 800 900 300 400 500 600 700 800 900 300 400 500 600 700 800 aelengt nm aelengt nm aelengt nm

Vapor-deposited film Vapor-deposited film Vapor-deposited film F F 1.0 F F 1.0 1.0 F F on on on i i i F F orp t orp t Cu orp t F s s F s a a a d d 0.5 F F 0.5 d 0.5 e e F F e F F C70 li li C60 li [F1233] F16CuPc [B1641] orm a orm a orm a [H1194] 0.0 0.0 0.0 300 400 500 600 700 800 900 300 400 500 600 700 800 300 400 500 600 700 800 aelengt nm aelengt nm aelengt nm

C12H25 Spin-coated film Spin-coated film CH3 Spin-coated film OCH 3 1.0 1.0 OCH3 1.0 O on on on O i i i orp t orp t orp t s s s a a a d d 0.5 0.5 d 0.5 e e e PCBM C60MC12 li li li [P2682] [C2415] [70]PCBM orm a orm a orm a [P2683] 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 aelengt nm aelengt nm aelengt nm

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Spin-coated film OCH3 Spin-coated film Vapor-deposited film O O 1.0 1.0 O 1.0 on on on H C CH i i i 3 3

O O orp t orp t orp t ICBA O s s s PTCDI-C1 a a a H3CO d d [I0900] d 0.5 0.5 0.5 [D4429] e e e li li li BisPCBM [B4576] orm a orm a orm a 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 aelengt nm aelengt nm aelengt nm

Vapor-deposited film Vapor-deposited film Spin-coated film 1.0 O O 1.0 O O 1.0 O O on on C H C H C H C H on i i 8 17 8 17 13 27 13 27 i

O O O O O O orp t orp t orp t s s PTCDI-C8 PTCDI-C13 s Orange a a a d d 0.5 [D4175] 0.5 [D3947] d 0.5 e e e [B4268] li li li orm a orm a orm a 0.0 0.0 0.0 300 400 500 600 700 800 300 400 500 600 700 800 300 400 500 600 700 800 aelengt nm aelengt nm aelengt nm

Spin-coated film CH2Cl2 solution CH2Cl2 solution 1.0 1.0 1.0 on on on i i i

O O CH3 S S orp t orp t orp t S S H3C CH3 C C s s s a a H3C O O a S S S S C C d d 0.5 d 0.5 0.5 e e e li li [B4583] li BEDT-TTF TCQ [B1200] [T3034] orm a orm a orm a 0.0 0.0 0.0 300 400 500 600 700 800 250 350 450 550 650 750 250 350 450 550 650 750 aelengt nm aelengt nm aelengt nm

CH2Cl2 solution 1.0 on i

F F orp t C C s a C C d 0.5 F F e li F4TCQ [T1131] orm a 0.0 250 350 450 550 650 750 aelengt nm

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Energy levels of HOMO 3 3 21 CH CH H 10 S S C -1 S Si Si S S S S S S [5942] S -3 S S ) C C 3 3 H [0951] H [P2524] [D4469] [P2207] [D5086] e V ( [T2233] [D3526] [D5491] [D4617] [D4618] [0220] g y -5 4.9 5.1 5.2 5.1 5.2 5.2 ne r 5.3 5.3 E 5.6 5.6 5.7 5.6 -7

-9 1 1 H S H H 10 6 8 C n C C S S S S S S 13 H

-1 6 S S C S S Cu S S S S 13 H S S 6

C H S S S S S S 13 Zn H

6 H S S C S S S S S S

-3 13 [P1628] H S S 6 C ) 21 13 17 S H H H 6 8

10 [P1795] C C [0037] C e V [3441] [P2513] [1200 (

[0504] [0078] [D4842] [D4877] [D4888]

g y -5 4.8 4.8 4.7 5.1 5.1 5.0 5.0 ne r 5.3 5.3 5.4 E 5.7 -7

-9

Energy levels of LUMO

-1

-3 3.5 3.6 3.6

) 3.8 4.0 4.0 3.9 4.0 3.9 3.9 4.2

C12H25 17 e V

3 4.5

OCH3 CH3 H ( 8

OCH3 C O CH O O O O O O C C 5.2 O F F g y -5 F F F F O F C C ne r F H3CO Cu E OCH F F 3 F F C C O O O O O O O [P2682] F F F F

-7 C 17

3 F F [4576] [2415] F H F [1641] H 8

[0900] C C [F1233] C T3034 [D4429] [4268] [1194] [D4175] T1131

-9 [P2683]

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Product o. Compound LUMO (eV) HOMO (eV) g (eV) Reference

0951 Tetracene 5.1 20) P2524 Pentacene 4.9 20) T2233 Rubrene 5.3 20) D4469 6,13-Diphenylpentacene 3.2 5.2 2.0 21) 5942 TIPS-Pentacene 3.4 5.1 1.8 22) P2207 Picene 5.6 23) D3526 DPh-BTBT 2.4 5.6 3.2 24) D5491 Ph-BTBT-10 5.7 25) D4617 anti-DMADT 3.1 5.2 26) D4618 sn-DMADT 3.0 5.2 26) D5086 DBTTT 2.4 5.3 2.9 27) 0220 6P 1.8 5.6 3.8 28) 0504 6T 3.1 5.3 2.2 29) 0078 4T 5.3 30)

D4842 C6-4T 5.1 2.7 31) D4877 C8-4T 5.1 2.7 31)

D4888 C10-4T 2.6 5.4 32) 3441 BP1T 5.7 33)

P2513 P3HT 4.8 34) P1628 CuPc 2.7 4.8 2.2 35)

P1795 H2PC 2.7 5.0 2.2 35) 0037 ZnPc 5.0 36)

1200 BEDT-TTF 4.7 37) 4576 Bis-PCBM 3.6 6.0 2.4 38)

0900 ICBA 3.5 6.0 2.5 38)

1641 C60 4.0 6.4 2.4 38)

F1233 C70 4.0 6.4 38) P2682 [60]PCBM 3.8 6.2 38) P2683 [70]PCBM 3.8 5.9 38)

2415 C60MC12 3.6 39) D4429 PTCDI-C1 4.0 6.6 2.6 40)

1194 F16CuPc 4.5 6.3 1.8 40)

D4175 PTCDI-C8 3.9 6.3 2.4 41) 4268 Perylene Orange 3.9 6.2 2.3 42) T3034 TCQ 4.2 43)

T1131 F4 -TCQ 5.2 44)

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22) I. Kaur, W. Jia, R. P. Kopreski, S. Selvarasah, M. R. Dokmeci, C. Pramanik, N. E. References McGruer, G. P. Miller, J. Am. Chem. Soc. 2008, 130, 16274. 23) T. Hosokai, A. Hinderhofer, F. Bussolotti, K. Yonezawa, C. Lorch, A. Vorobiev, Y. Hasegawa, Y. Yamada, Y. Kubozoro, A. Gerlach, S. Kera, F. Schreiber, N. 1) K. Kudo, M. Yamashinaand, T. Moriizumi, Jpn. J. Appl. Phys. 1984, 23, 130. Ueno, J. Phys. Chem. C 2015, 119, 2902. 2) Y. Y. Lin, D. J. Gundlach, S. F. Nelson and T. N. Jackson, IEEE Trans. 24) K. Takimiya, H. Ebata, K. Sakamoto, T. Izawa, T. Otsubo, Y. Kunugi, J. Am. Devices 1997, 44, 1325. Chem. Soc. 2006, 128, 12604. 3) M. Kaltenbrunner, T. Sekitani, J. Reeder, T. Yokota, K. Kuribara, T. Tokuhara, 25) M. Kunii, H. Iino, J. Hanna, Appl. Phys. Lett. 2017, 110, 243301. M. Drack, R. Schwödiauer, I. Graz, S. Bauer-Gogonea, S. Bauer, T. Someya, 26) M. Mamada, T. Minamiki, H. Katagiri, S. Tokito, Org. Lett. 2012, 14, 4062. Nature 2013, 499, 458. 27) J.-Ⅱ Park, J. W. Chung, J.-Y. Kim, J. Lee, J. Y. Jung, B. Koo, B.-L. Lee, S. W. Lee, 4) B. Chu, W. Burnett, JW. Chung, Z. Bao, Nature 2017, 355, 328. Y. W. Jin, S. Y. Lee, J. Am. Chem. Soc. 2015, 137, 12175. 5) A. C. Arias, J. D. MacKenzie, I. McCulloch, J. Rivnay, A. Salleo, Chem. Rev. 28) C. Qian, J. Sun, L. Kong, Y. Fu, Y. Chen, J. Wang, S. Wang, H. Xie, H. Huang, J. 2010, 110, 3. Yang, Y. Gao, ACS Photonics 2017, 4, 2573. 6) B. Kang, W. H. Lee, K. Cho, ACS Appl. Mater. Interfaces 2013, 5, 2302. 29) J. Sakai, T. Taima, T. Yamanari, K. Saito, Sol. Energy Mater. Sol. Cells 2009, 93, 7) K. Fukuda, T. Someya, Adv. Mater. 2017, 29, 1602736. 1149. 8) J. G. Mei, Y. Diao, A. L. Appleton, L. Fang, Z. N. Bao, J. Am. Chem. Soc. 2013, 30) H. Méndez, G. Heimel, S. Winkler, J. Frisch, A. Opitz1, K. Sauer, B. Wegner, M. 135, 6724. Oehzelt, C. Röthel, S. Duhm, D. Többens, N. Koch, I. Salzmann, Nat. Comm. 9) K. Takimiya, H. Ebata, K. Sakamoto, T. Izawa, T. Otsubo, Y. Kunugi, J. Am. 2015, 6, 8560 Chem. Soc. 2006, 128, 12604. 31) M. Ashizawa, T. Niimura, Y. Yu, K. Tsuboi, H. Matsumoto, R. Yamada, S. 10) H. Iino, T. Usui, J.‐I. Hanna, Nat. Commun. 2015, 6, 6828. Kawauchi, A. Tanioka, T. Mori, Tetrahedron 2012, 68, 2790. 11) R. Ruiz, D. Choudhary, B. Nickel, T. Toccoli, K.-C. Chang, A. C. Mayer, P. Clancy, 32) S. A. Ponomarenko, S. Kirchmeyer, A Elschner, N. M. Alpatova, M. Halik, H. J. M. Blakely, R. L. Headrick, S. Iannotta, G. G. Malliaras, Chem. Mater. 2004, Klauk, U. Zschieschang, G. Schmid, Chem. Mater. 2006, 18, 579. 16, 4497. 33) T. J. Dingemans, A. Bacher, M. Thelakkat, L. G. Pedersen, E. T. Samulski, H.-W. 12) B. Nickel, M. Fiebig, S. Schiefer, M. Göllner, M. Huth, C. Erlen, P. Lugli, Phys. Schmidt, Synthetic Metals 1999, 105, 171. Stat. Sol. A 2008, 205, 526 34) V. Vohra, G. Arrighetti, L. Barba, K. Higashimine, W. Porzio, H. Murata, J. Phys. 13) M. Kitamura, Y. Arakawa, J. Phys.: Condens. Matter. 2008, 20, 184011 Chem. Lett. 2012, 3, 1820. 14) Q. Wang, R. Takita, Y. Kikuzaki, F. Ozawa, J. Am. Chem. Soc. 2010, 132, 11420. 35) D. R. T. Zahn, M. Gorgoi, O. D. Gordan, Sol. Ener. 2006, 80, 707. 15) J.-R. Pouliot, M. Wakioka, F. Ozawa, Y. Li, M. Leclerc, Macromol. Chem. Phys. 36) W. Tress, K. Leo, M. Riede, Adv. Funct. Mater. 2011, 21, 2140. 2016, 217, 1493. 37) N. Sato, G. Saito, H. Inokuchi, Chem. Phys. 1983, 76, 79. 16) R. Zhang, B. Li, M. C. Iovu, M. Jeffries-EL, G. Sauvé, J. Cooper, S. Jia, S. Tristram- 38) H. Yoshida, J. Phys. Chem. C 2014, 118, 24377. Nagle, D. M. Smilgies, D. N. Lambeth, R. D. McCullough, T. Kowalewski, J. Am. 39) M. Chikamatsu, A. Itakura, Y. Yoshida, R. Azumi, K. Yase, Chem. Mater. 2008, Chem. Soc. 2006, 128, 3480. 20, 7365. 17) H. Sirringhaus, P. J. Brown, R. H. Friend, M. M. Nielsen, K. Bechgaard, B. M. W. 40) D. R. T. Zahn, G. N. Gavrila. M. Gorgoi, Chem. Phys. 2006, 325, 99. Langeveld-Voss, A. J. H. Spiering, R. A. J. Janssen, E. W. Meijer, P. Herwig, D. 41) B. A. Jones, A. Facchetti, M. R. Wasielewski, T. J. Marks, J. Am. Chem. Soc. M. de Leeuw, Nature 1999, 401, 685. 2007, 129, 15259. 18) J.-F. Chang, B. Sun, D. W. Breiby, M. M. Nielsen, T. I. Sӧlling, M. Giles, I. 42) I. Kim, H. M. Haverinen, Z. Wang, S. Madakuni, J. Li, G. E. Jabbour, Appl. Phys. McCulloch, H. Sirringhaus, Chem. Mater. 2004, 16, 4772. Lett. 2009, 95, 023305. 19) L. A. Majewski, J. W. Kingsley, C. Balocco, A. M. Songa, Appl. Phys. Lett. 2006, 43) K. Kanai, K, Akaike, K. Koyasu, K. Sakai, T. Nishi, Y. Kamizuru, T. Nishi, Y. Ouchi, 88, 222108. K. Seki, Appl. Phys. A 2009, 95, 309. 20) N. Sato, K. Seki, H Inokuchi, J. Chem. Soc., Faraday Trans. 2 1981, 77, 1621. 44) W. Gao, A. Kahn, Appl. Phys. Lett. 2001, 79, 4040. 21) L. C. Picciolo, H. Murata, Z. H. Kafafi, Appl. Phys. Lett. 2001, 78, 2378.

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P2524 100mg 1g D5491 100mg 250mg P2513 100mg 500mg

(CH ) CH S 2 5 3 High Quality Organic (CH2)9CH3 S Semiconductor Materials S n Pentacene (99.999%, trace metals basis) (purified by sublimation) Ph-BTBT-10 P3HT (regioregular) CAS RN: 135-48-8 CAS RN: 1398395-83-9 CAS RN: 125321-66-6 P2682 100mg F1233 100mg P2683 100mg

OCH3 OCH3 O O

Fullerene C70 [70]PCBM (mixture of isomers) PCBM [for organic electronics] [for organic electronics] [for organic electronics] CAS RN: 160848-22-6 CAS RN: 115383-22-7 CAS RN: 609771-63-3 N0001 100mg 1g 5g N0951 200mg 1g P0030 100mg 1g p-Type Organic Semiconductors Naphthacene Naphthacene (purified by sublimation) Pentacene (purified by sublimation) CAS RN: 92-24-0 CAS RN: 92-24-0 CAS RN: 135-48-8 P2524 100mg 1g D5152 100mg T0561 100mg 1g T2233 250mg 1g D4469 200mg

Pentacene (99.999%, trace metals 2,6-Diphenylanthracene basis) (purified by sublimation) (purified by sublimation) Rubrene Rubrene (purified by sublimation) 6,13-Diphenylpentacene CAS RN: 135-48-8 CAS RN: 95950-70-2 CAS RN: 517-51-1 CAS RN: 517-51-1 CAS RN: 76727-11-2 P2207 100mg P2383 100mg B5551 200mg 1g D3526 100mg D5491 100mg 250mg

S S S (CH2)9CH3 S S S S S Picene (purified by Phenanthro[1,2-b:8,7-b']- sublimation) (>99.9%) dithiophene BTBT DPh-BTBT (purified by sublimation) Ph-BTBT-10 CAS RN: 213-46-7 CAS RN: 1491133-64-2 CAS RN: 248-70-4 CAS RN: 900806-58-8 CAS RN: 1398395-83-9 D4617 100mg D4618 100mg D5153 50mg D5154 50mg B3441 1g 5g

O O

N N CH3 S O O S S CH S S CH S S CH3 3 3 anti-DMADT syn-DMADT S S (purified by sublimation) (purified by sublimation) endo-DNTT-PMI (DNTT-Precursor) exo-DNTT-PMI (DNTT-Precursor) BP1T CAS RN: 1019983-99-3 CAS RN: 1392416-39-5 CAS RN: 1269669-42-2 CAS RN: 1269669-43-3 CAS RN: 56316-86-0 H1448 50mg D4487 200mg 1g B4683 200mg S0220 100mg 1g T1196 1g 5g

S S S CH3(CH2)7 S S (CH2)7CH3 S S S S N N N N (CH2)5CH3 S S 4,7-Di(2-thienyl)- 4,7-Bis(5-n-octyl-2-thienyl)- α-Terthienyl AC5-Hx (purified by sublimation) 2,1,3-benzothiadiazole 2,1,3-benzothiadiazole p-Sexiphenyl (purified by sublimation) CAS RN: 1172135-81-7 CAS RN: 165190-76-1 CAS RN: 1171974-28-9 CAS RN: 4499-83-6 CAS RN: 1081-34-1 Q0078 100mg Q0079 100mg 500mg S0504 100mg 1g S0505 100mg O0313 100mg

S S S S S S S S S S S S S S S 2 3 4 5 6 α-Sexithiophene α-Quaterthiophene α-Quinquethiophene (purified by sublimation) α-Septithiophene α-Octithiophene CAS RN: 5632-29-1 CAS RN: 5660-45-7 CAS RN: 88493-55-4 CAS RN: 86100-63-2 CAS RN: 113728-71-5

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P2513 100mg 500mg D4842 100mg D4877 100mg D4888 100mg D4889 100mg

(CH2)5CH3

CH3(CH2)5 S S 2 S (CH2)5CH3 CH3(CH2)7 S S 2 S (CH2)7CH3 CH3(CH2)9 S S 2 S (CH2)9CH3 CH3(CH2)11 S S 2 S (CH2)11CH3 S n 5,5'''-Di-n-octyl-2,2':5',2'':5'',2'''- 5,5'''-Didecyl-2,2':5',2'':5'',2'''- 5,5'''-Didodecyl-2,2':5',2'':5'',2'''- P3HT (regioregular) α,ω-Dihexylquaterthiophene quaterthiophene quaterthiophene quaterthiophene CAS RN: 125321-66-6 CAS RN: 132814-92-7 CAS RN: 882659-01-0 CAS RN: 514188-77-3 CAS RN: 153561-79-6 P1795 1g P1628 1g P0767 1g 5g 25g Z0037 500mg B1200 100mg 1g 5g

N N N N NH N N N N N N N N N N Cu N S SSS N N N HN N N N Zn N Zn N N N N N N S S S S N N Phthalocyanine (purified by sublimation) (purified by sublimation) Zinc Phthalocyanine ZnPc (purified by sublimation) BEDT-TTF CAS RN: 574-93-6 CAS RN: 147-14-8 CAS RN: 14320-04-8 CAS RN: 14320-04-8 CAS RN: 66946-48-3 H1194 100mg 1g B1641 100mg 1g M2088 100mg F F F F F F N OCH3 F F N N O n-Type Organic N Cu N F N N F N Semiconductors F F FF F F F16CuPc (purified by sublimation) C60 (pure) PCBM CAS RN: 14916-87-1 CAS RN: 99685-96-8 CAS RN: 160848-22-6 P2682 100mg B4576 50mg C2415 100mg I0900 50mg B1694 100mg

CH3 (CH2)11CH3 OCH3 OCH N 3 O O

O

OCH3

PCBM [for organic electronics] Bis-PCBM (mixture of isomers) C60MC12 ICBA Fullerene C70 CAS RN: 160848-22-6 CAS RN: 1048679-01-1 CAS RN: 403483-19-2 CAS RN: 1207461-57-1 CAS RN: 115383-22-7 F1233 100mg M2550 50mg P2683 100mg N0369 25g 250g N0755 1g 5g OOO OOO

OCH3 OCH3 O O

Fullerene C70 [70]PCBM (mixture of isomers) OOO OOO [for organic electronics] [70]PCBM (mixture of isomers) [for organic electronics] NTCDA NTCDA (purified by sublimation) CAS RN: 115383-22-7 CAS RN: 609771-63-3 CAS RN: 609771-63-3 CAS RN: 81-30-1 CAS RN: 81-30-1 P0972 25g 100g 500g P2102 1g D4429 1g 5g D4175 1g D3947 200mg 1g

O O O O

O O O O O O O O O O CH3(CH2)7 N N (CH2)7CH3 CH (CH ) N N (CH ) CH CH3 N N CH3 3 2 12 2 12 3 O O O O O O O O O O Pigment Red 224 Pigment Red 224 (purified by sublimation) Pigment Red 179 PTCDI-C8 PTCDI-C13 CAS RN: 128-69-8 CAS RN: 128-69-8 CAS RN: 5521-31-3 CAS RN: 78151-58-3 CAS RN: 95689-92-2 B4268 1g 5g B4583 200mg T0078 5g 25g T1131 100mg 1g NC CN NC CN C C O O CH3 N F F (CH3)2CH O O CH(CH3)2 CH3 N N CH3 N N N CH3 O O F F (CH3)2CH O O CH(CH3)2 N,N'-Bis[2-(dimethylamino)- C C ethyl]-1,8:4,5-- NC CN NC CN Perylene Orange tetracarboxdiimide TCNQ F4TCNQ (purified by sublimation) CAS RN: 82953-57-9 CAS RN: 22291-04-9 CAS RN: 1518-16-7 CAS RN: 29261-33-4 B4361 1g B3612 100mg C2780 200mg

CH3 S S N CH3 N N O Ambipolar S S S S N Ni N N S S N O CH3 Semiconductors N SS CH3 BDN BTQBT (purified by sublimation) CZBDF CAS RN: 38465-55-3 CAS RN: 135704-54-0 CAS RN: 1092578-51-2

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T3042 50mg 200mg

1,3,6,8-Tetraphenylpyrene CAS RN: 13638-82-9 D5491 100mg 250mg D4842 100mg D4877 100mg

S Liquid Crystalline (CH2)9CH3 Semiconductors S CH3(CH2)5 S S 2 S (CH2)5CH3 CH3(CH2)7 S S 2 S (CH2)7CH3 5,5'''-Di-n-octyl-2,2':5',2'':5'',2'''- Ph-BTBT-10 α,ω-Dihexylquaterthiophene quaterthiophene CAS RN: 1398395-83-9 CAS RN: 132814-92-7 CAS RN: 882659-01-0 D4888 100mg D4889 100mg B4683 200mg H1449 200mg 1g H1450 200mg 1g

O(CH2)5CH3 O(CH2)7CH3

O(CH2)5CH3 O(CH2)7CH3

CH3(CH2)5O CH3(CH2)7O

CH (CH ) S S (CH ) CH 3 2 7 2 7 3 CH3(CH2)5O CH3(CH2)7O

CH3(CH2)9 S S 2 S (CH2)9CH3 CH3(CH2)11 S S 2 S (CH2)11CH3 N N O(CH ) CH S 2 5 3 O(CH2)7CH3 O(CH ) CH 2 5 3 O(CH2)7CH3 5,5'''-Didecyl-2,2':5',2'':5'',2'''- 5,5'''-Didodecyl-2,2':5',2'':5'',2'''- 4,7-Bis(5-n-octyl-2-thienyl)- 2,3,6,7,10,11-Hexakis(hexyloxy)- 2,3,6,7,10,11-Hexakis[(n-octyl)- quaterthiophene quaterthiophene 2,1,3-benzothiadiazole oxy]triphenylene CAS RN: 514188-77-3 CAS RN: 153561-79-6 CAS RN: 1171974-28-9 CAS RN: 70351-86-9 CAS RN: 70351-87-0

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