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4 protocols using butyl acetate

1

Solution-Processed Optoelectronic Devices

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Lead(ii) iodide powder (PbI2, 99.0%), oleic acid (OAc, 90.0%), and n-octylamine (OAm, 99.0%) were purchased from Aldrich. Hydroiodic acid (HI, 57 wt%), toluene (99.5%), mEthyl acetate (98.0%), and butyl acetate (99.0%) were purchased from Wako Pure Chemical Industries. Propyl acetate (98.0%) was purchased from Tokyo Chemical Industry. Ethyl acetate (99.3%) was purchased from Kanto Chemical Co., Inc. YTZ® balls (ZrO2 beads 50 μm in diameter) were purchased from Nikkato Co., Ltd. Poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate) (PEDOT:PSS, AI4083), poly(4-butylphenyl-diphenyl-amine) (poly-TPD), and tris-[1-phenyl-1H-benzimidazole] (TPBi) were purchased from Clevious and American Dye Source and e-Ray Optoelectronics Technology Co., Ltd. All chemicals were used without purification.
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2

Synthesis of Compound A-2 from Ditrimethylolpropane and Cyclohexane-1,2,4-tricarboxylic Acid Anhydride

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Example 4

A compound A-2 was synthesized as follows.

To a 200 mL flask were added 7.51 g (30 mmol) of ditrimethylolpropane (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 23.78 g (120 mmol) of cis,cis-cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride (manufactured by Mitsubishi Gas Chemical Company, Inc., H-TMAn-S (trade name)), and 31.29 g of butyl acetate (manufactured by FUJIFILM Wako Pure Chemical Corporation, reagent special grade), and the mixture was stirred at 100° C. for 6 hours under a nitrogen atmosphere. Thereafter, the mixture was cooled to room temperature (25° C.) to obtain a reaction solution.

As a result of 1H-NMR measurement of the obtained reaction solution, it was confirmed that the compound (A-2) represented by the formula (17) was contained.

In addition, the obtained reaction solution was subjected to GPC measurement under the same conditions as the GPC measurement described in the synthesis of the compound represented by the formula (16). As a result, the disappearance of the peak derived from ditrimethylolpropane and the peak derived from cis,cis-cyclohexane-1,2,4-tricarboxylic acid-1,2-anhydride was confirmed. As a result of calculating the GPC area fraction (content) of the compound (A-2) contained in the reaction solution, the content was 77%.

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3

Biphenyltetracarboxylic Dianhydride Synthesis

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3,4,3’,4’‐Biphenyltetracarboxylic dianhydride (BPDA, >98.0 % purity) was purchased from Tokyo Chemical Industry, Co., Ltd. 4,4’‐Oxydianiline (ODA, >98.0 % purity), the solvent N‐methylpyrrolidone (NMP, >97.0 % purity), xylene (>80.0 %), butyl acetate (>98.0 %), acetone (>99.0 %), isopropanol (>98.0 %), and methanol (>99.5 %) were purchased from Wako Pure Chemical Industries, Ltd. All reagents were used without further purification.
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4

Solvent Selection and Characterization

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The following 30 solvents (96.0%–99.0% pure) were used without purification: linear alkanes with different carbon chain length (n = 6–16); aromatic hydrocarbons; linear aliphatic alcohols with different carbon chain length (n = 1–9); aromatic alcohols with different carbon chain length of the alkyl group (n = 0–3); acetate esters; unsaturated hydrocarbons; and branched alkanes. Hexane, octane, nonane, decane, dodecane, tetradecane, hexadecane, toluene, styrene, methanol, ethanol, 1-heptanol, 1-octanol, 1,4-butanediol, benzyl alcohol, 2-phenylethanol, propyl acetate, iso -butyl acetate, tert -butyl acetate, butyl acetate, pentyl acetate, octyl acetate, 1-octadecene, and squalene were supplied by Wako Pure Chemical Industries, Ltd. (Osaka, Japan). Butylbenzene, tert-Butylbenzene, octylbenzene, 1-nonanol, and 3-phenyl-1-propanol were supplied by Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). Diluted ethane and ethylene (99.5% pure) and undiluted acetylene (0.1% in N2) were used as standard gases for gas chromatography. These gases were supplied by GL sciences Inc. (Tokyo, Japan). For the spin-trapping agent, we used 5,5-dimethyl-1-pyrroline N-oxide (DMPO; > 97.0% pure), which was supplied by Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan).
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