JPWO2016136425A1 - フッ素原子含有重合体及びその利用 - Google Patents
フッ素原子含有重合体及びその利用 Download PDFInfo
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- JPWO2016136425A1 JPWO2016136425A1 JP2017502028A JP2017502028A JPWO2016136425A1 JP WO2016136425 A1 JPWO2016136425 A1 JP WO2016136425A1 JP 2017502028 A JP2017502028 A JP 2017502028A JP 2017502028 A JP2017502028 A JP 2017502028A JP WO2016136425 A1 JPWO2016136425 A1 JP WO2016136425A1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- MQZFZDIZKWNWFX-UHFFFAOYSA-N osmium(2+) Chemical compound [Os+2] MQZFZDIZKWNWFX-UHFFFAOYSA-N 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006488 t-butyl benzyl group Chemical group 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XSVXWCZFSFKRDO-UHFFFAOYSA-N triphenyl-(3-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XSVXWCZFSFKRDO-UHFFFAOYSA-N 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- HITRWHKLCHWBNZ-UHFFFAOYSA-N triphenyl-[4-(9-phenylfluoren-9-yl)phenyl]silane Chemical compound C1=CC=CC=C1C1(C=2C=CC(=CC=2)[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 HITRWHKLCHWBNZ-UHFFFAOYSA-N 0.000 description 1
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Abstract
Description
1.下記式(1)で表される繰り返し単位を与えるフルオレン誘導体と、下記式(2)で表される繰り返し単位を与えるフルオレン誘導体と、下記式(3)で表される繰り返し単位を与えるフルオレン誘導体との縮合重合体であることを特徴とするフッ素原子含有重合体。
R3及びR4は、それぞれ独立に、非共役系の2価の有機基を表し;
R5は、水素原子、又は少なくとも1つの水素原子がフッ素原子で置換されていてもよい、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基、炭素数8〜20のアルキルアラルキル基、炭素数2〜20のヘテロアリール基、炭素数6〜20のアリールオキシ基若しくは炭素数2〜20のヘテロアリールオキシ基を表し;
R6は、少なくとも1つの水素原子がフッ素原子で置換された、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基、炭素数8〜20のアルキルアラルキル基、炭素数2〜20のヘテロアリール基、炭素数6〜20のアリールオキシ基又は炭素数2〜20のヘテロアリールオキシ基を表し;
Rは、それぞれ独立に、ハロゲン原子、ニトロ基、シアノ基、Z1で置換されていてもよい、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基若しくは炭素数2〜20のアルキニルオキシ基、又はZ2で置換されていてもよい、炭素数6〜20のアリール基、炭素数2〜20のヘテロアリール基、炭素数6〜20のアリールオキシ基若しくは炭素数2〜20のヘテロアリールオキシ基を表し;
Z1は、ハロゲン原子、ニトロ基、シアノ基、又はZ3で置換されていてもよい、炭素数6〜20のアリール基、炭素数2〜20のヘテロアリール基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基若しくは炭素数2〜20のヘテロアリール基を表し;
Z2は、ハロゲン原子、ニトロ基、シアノ基、又はZ3で置換されていてもよい、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基若しくは炭素数2〜20のヘテロアリール基を表し;
Z3は、ハロゲン原子、ニトロ基又はシアノ基を表し;
p及びqは、それぞれ独立に、0又は1を表す。]
2.重量平均分子量が、1,000〜200,000である1の重合体。
3.R1及びR2が、ともに炭素数1〜20のアルキル基又はともに少なくとも1つのエーテル構造を含む炭素数2〜20のアルキル基である1又は2の重合体。
4.R3及びR4が、−Rc−Ar−(式中、Rcは、炭素数1〜20のアルキレン基を表し、Arは、炭素数6〜20のアリーレン基を表す。)である1〜3のいずれかの重合体。
5.R5が、少なくとも1つの水素原子がフッ素原子で置換された、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基、炭素数8〜20のアルキルアラルキル基、炭素数2〜20のヘテロアリール基、炭素数6〜20のアリールオキシ基又は炭素数2〜20のヘテロアリールオキシ基である1〜4のいずれかの重合体。
6.1〜5のいずれかの重合体からなる電荷輸送性物質。
7.6の電荷輸送性物質、フッ素原子を含有しない電荷輸送性物質、ヘテロポリ酸からなるドーパント、及び有機溶媒を含む電荷輸送性ワニス。
8.前記フッ素原子を含有しない電荷輸送性物質が、アニリン誘導体である7の電荷輸送性ワニス。
9.7又は8の電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
10.9の電荷輸送性薄膜を有する電子デバイス。
11.9の電荷輸送性薄膜を有する有機エレクトロルミネッセンス素子。
12.7又は8の電荷輸送性ワニスを基材上に塗布し、溶媒を蒸発させることを特徴とする電荷輸送性薄膜の製造方法。
13.下記式(1')で表されるフルオレン誘導体と、下記式(2')で表されるフルオレン誘導体と、下記式(3')で表されるフルオレン誘導体とを縮合重合させることを特徴とする1のフッ素原子含有重合体の製造方法。
14.下記式で表されるフルオレン誘導体。
p及びqは、それぞれ独立に、0又は1を表す。]
15.下記式で表されるフルオレン誘導体。
XAは、それぞれ独立に、ハロゲン原子又は擬ハロゲン基を表し;
p及びqは、それぞれ独立に、0又は1を表す。]
16.下記式で表されるフルオレン誘導体。
17.下記式で表されるフルオレン誘導体。
本発明のフッ素原子含有重合体は、下記式(1)で表される繰り返し単位を与えるフルオレン誘導体と、下記式(2)で表される繰り返し単位を与えるフルオレン誘導体と、下記式(3)で表される繰り返し単位を与えるフルオレン誘導体との縮合重合体である。
−(RAO)r−RB (A)
−(CH2CH2O)r−CH3 (B)
(式中、RAは炭素数1〜4の直鎖状又は分岐状のアルキレン基を表し、RBは炭素数1〜[20−(RAの炭素数)×r]の直鎖状又は分岐状のアルキル基を表し、rは1〜9の整数である。rは、ドーパントとの相溶性の観点から、好ましくは2以上、より好ましくは3以上であり、原料化合物の入手容易性の観点から、好ましくは5以下、より好ましくは4以下である。)
-CH2CH2O(CH2)5CH3、-CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2OCH2CH(CH3)(CH2)2CH3、-CH2CH2O(CH2)2CH(CH3)CH2CH3、-CH2CH2O(CH2)3CH(CH3)2、-CH2CH2OC(CH3)2(CH2)2CH3、-CH2CH2OCH(CH2CH3)(CH2)2CH3、-CH2CH2OC(CH3)2CH(CH3)2、-CH2CH2O(CH2)6CH3、-CH2CH2O(CH2)7CH3、-CH2CH2OCH2CH(CH2CH3)(CH2)3CH3、-CH2CH2O(CH2)8CH3、-CH2CH2O(CH2)9CH3、-CH2CH2O(CH2)10CH3、-CH2CH2O(CH2)11CH3、-CH2CH2O(CH2)12CH3、-CH2CH2O(CH2)13CH3、-CH2CH2O(CH2)14CH3、-CH2CH2O(CH2)15CH3、-CH2CH2O(CH2)16CH3、-CH2CH2O(CH2)17CH3、-CH2CH2CH2OCH3、-CH2CH2CH2OCH2CH3、-CH2CH2CH2O(CH2)2CH3、-CH2CH2CH2OCH(CH3)2、-CH2CH2CH2O(CH2)3CH3、-CH2CH2CH2OCH2CH(CH3)2、-CH2CH2CH2OC(CH3)3、-CH2CH2CH2O(CH2)4CH3、-CH2CH2CH2OCH(CH3)(CH2)2CH3、-CH2CH2CH2OCH2CH(CH3)2、-CH2CH2CH2O(CH2)2CH(CH3)2、-CH2CH2CH2OC(CH3)3、-CH2CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2CH2O(CH2)5CH3、-CH2CH2CH2OCH(CH3)(CH2)3CH3、-CH2CH2CH2OCH2CH(CH3)(CH2)2CH3、-CH2CH2CH2O(CH2)2CH(CH3)CH2CH3、-CH2CH2CH2O(CH2)3CH(CH3)2、-CH2CH2CH2OC(CH3)2(CH2)2CH3、-CH2CH2CH2OCH(CH2CH3)(CH2)2CH3、-CH2CH2CH2OC(CH3)2CH(CH3)2、-CH2CH2CH2O(CH2)6CH3、-CH2CH2CH2O(CH2)7CH3、-CH2CH2CH2OCH2CH(CH2CH3)(CH2)3CH3、-CH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH2CH2CH2OCH3、-CH2CH2CH2CH2OCH2CH2CH2CH2OCH2CH2CH2CH2OCH3、-CH2CH2CH2CH2OCH2CH2CH2CH2OCH2CH2CH2CH2OCH2CH2CH2CH2OCH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH3、-CH2CH2OCH2CH2OCH2CH2OCH2CH3、-CH2CH2CH2O(CH2)8CH3、-CH2CH2CH2O(CH2)9CH3、-CH2CH2CH2O(CH2)10CH3、-CH2CH2CH2O(CH2)11CH3、-CH2CH2CH2O(CH2)12CH3、-CH2CH2CH2O(CH2)13CH3、-CH2CH2CH2O(CH2)14CH3、-CH2CH2CH2O(CH2)15CH3、-CH2CH2CH2O(CH2)16CH3等が挙げられる。
本発明のフッ素原子含有重合体は、式(1)で表される繰り返し単位を与えるフルオレン誘導体と、式(2)で表される繰り返し単位を与えるフルオレン誘導体と、式(3)で表される繰り返し単位を与えるフルオレン誘導体との縮合重合によって合成することができる。
本発明のフッ素原子含有重合体は、電荷輸送性物質として好適に使用できる。本発明において、電荷輸送性とは、導電性と同義であり、正孔輸送性と同義である。電荷輸送性物質とは、それ自体に電荷輸送性があるものでもよく、ドーパントと共に用いた際に電荷輸送性があるものでもよい。電荷輸送性ワニスとは、それ自体に電荷輸送性があるものでもよく、それにより得られる固形膜が電荷輸送性を有するものでもよい。
本発明の電荷輸送性ワニスは、前記フッ素原子含有重合体からなる電荷輸送性物質、フッ素原子を含有しない電荷輸送性物質、ヘテロポリ酸からなるドーパント、及び有機溶媒を含む。
フッ素原子を含有しない電荷輸送性物質としては、アニリン誘導体、チオフェン誘導体、ピロール誘導体等の電荷輸送性オリゴマーが挙げられる。電荷輸送性オリゴマーの分子量は、通常、200〜5,000であるが、電荷輸送性の高い薄膜を与えるワニスを調製する観点から、好ましくは300以上、より好ましくは400以上、より一層好ましくは500以上であり、平坦性の高い薄膜を与える均一なワニスを調製する観点から、好ましくは4,000以下であり、より好ましくは3,000以下であり、より一層好ましくは2,000以下である。
本発明の電荷輸送性ワニスは、ドーパントとしてヘテロポリ酸を含む。それゆえ、インジウム錫酸化物(ITO)、インジウム亜鉛酸化物(IZO)に代表される透明電極からの高正孔受容能のみならず、アルミニウムに代表される金属陽極からの高正孔受容能を示す電荷輸送性に優れた薄膜を得ることができる。
電荷輸送性ワニスを調製する際に用いられる有機溶媒としては、電荷輸送性物質及びドーパントを良好に溶解し得る高溶解性溶媒を用いることができる。
本発明の電荷輸送性ワニスを基材上に塗布して焼成することで、基材上に電荷輸送性薄膜を形成させることができる。
本発明の電荷輸送性ワニスを用いてOLED素子を作製する場合の使用材料や作製方法としては、下記のようなものが挙げられるが、これらに限定されない。
(1)1H-NMR:日本電子(株)製ECX-300
(2)LC/MS:Waters社製、ZQ 2000、AB Sciex社製、TripleTOF5600+
(3)MALDI-TOF-MS:ブルカー社製、autoflex III smartbeam
(4)基板洗浄:長州産業(株)製、基板洗浄装置(減圧プラズマ方式)
(5)ワニスの塗布:ミカサ(株)製、スピンコーターMS-A100
(6)膜厚測定:(株)小坂研究所製、微細形状測定機サーフコーダET-4000
(7)GPC測定:(株)島津製作所製(カラム:SHODEX GPC KF-804L+GPC KF-805L、カラム温度:40℃、検出器:UV検出器(254nm)及びRI検出器、溶離液:THF、カラム流速:1.0mL/min)
(8)EL素子の作製:長州産業(株)製、多機能蒸着装置システムC-E2L1G1-N
(9)EL素子の輝度等の測定:(有)テック・ワールド製、I-V-L測定システム
1H-NMR (300MHz, CDCl3): δ 2.33(app t, J=7.8Hz, 4H), 2.78(app t, J=7.8Hz, 4H), 3.19-3.22(m, 4H), 3.35(s, 6H), 3.37-3.41(m, 4H), 3.50-3.52(m, 8H), 7.46(dd, J=1.8, 8.4Hz, 2H), 7.51(d, J=8.4Hz, 2H), 7.53(d, J=1.8Hz, 2H).
LC/MS (ESI+) m/z; 634[M+NH4]+
1H-NMR (300MHz, CDCl3): δ 2.13(app t, J=7.2Hz, 4H), 2.88(app t, J=7.2Hz, 4H), 3.28-3.31(m, 4H), 3.34(s, 6H), 3.45-3.51(m, 8H), 3.54-3.58(m, 4H), 6.98-7.11(m, 16H), 7.22-7.27(m, 8H), 7.44(d, J=8.1Hz, 2H).
LC/MS (ESI+) m/z; 794[M+H]+
1H-NMR(300MHz, CDCL3): δ 2.14(app t, J=7.2Hz, 4H), 2.86(app t, J= 7.2Hz, 4H), 3.26-3.33(m, 4H), 3.35(s, 6H), 3.41-3.57(m, 12H), 6.83-7.05(m, 12H), 7.25-7.47(m, 10H).
LC/MS (ESI+) m/z; 1131[M+Na]+
1H-NMR(300MHz, CDCL3): δ 1.33(s, 12H), 7.01-7.12(m, 8H), 7.23-7.28(m, 4H), 7.66(d, J=8.7Hz, 2H).
LC/MS (ESI+) m/z; 372[M+H]+
1H-NMR(300MHZ,CDCl3): δ 2.45(app t, J=7.2Hz, 4H), 2.84(app t, J= 7.2Hz, 4H), 3.20-3.23(m, 4H), 3.29(s, 6H), 3.37-3.50(m, 12H), 7.02-7.07(m, 4H), 7.14-7.19(m, 12H), 7.24-7.31(m, 8H), 7.53-7.61(m,8H), 7.72(d, J=8.1Hz, 2H).
LC/MS (ESI+) m/z; 963[M+NH4]+
1H-NMR(300MHz, CDCl3): δ 2.46(app t, J=7.2Hz,4H), 2.84(app t, J=7.2Hz, 4H), 3.20-3.24(m, 4H), 3.30(s,6H), 3.37-3.50(m, 12H), 7.01(d, J=9.0Hz, 8H), 7.15(d, J=8.4Hz, 4H), 7.38(d, J=9.0Hz, 8H), 7.56-7.61(m, 8H), 7.73(d, J=7.8Hz, 2H).
LC/MS (ESI+) m/z; 1278[M+NH4]+
1H-NMR(300MHz, CDCl3): δ 3.31(s, 4H), 6.48(d, J=8.4Hz, 4H), 7.00(d, J=8.7Hz, 4H), 7.20-7.31(m, 4H), 7.39-7.42(m, 4H).
MALDI-TOF-MS m/z; 526[M+Na]+
1H-NMR (300MHz, CDCl3): δ 1.27(s, 24H), 3.34(s, 4H), 6.68(d, J=7.8Hz,4H), 7.17-7.26 (m,4H), 7.35-7.41(m, 8H).
LC/MS (APCI+) m/z; 598[m]+
1H-NMR(300MHz, CDCl3): δ 3.41(s, 4H), 6.73(d, J=8.4Hz, 4H), 7.19-7.22(m, 6H), 7.38(dd, J=1.8, 8.4Hz, 2H), 7.59(d, J=1.2Hz, 2H).
1H-NMR(300MHz, CDCl3): δ 1.41(s, 24H), 3.45(s, 4H), 6.71(d, J=7.8Hz, 4H), 7.13(d, J=7.8Hz, 4H), 7.43(d, J=7.5Hz, 2H), 7.70(d, J=7.8Hz, 2H), 7.83(s, 2H).
LC/MS (ESI+) m/z; 780[M+HCOO]-
[実施例1]電荷輸送性ワニスA
ポリマー1(64mg)、国際公開第2013/084664号記載の方法に従って合成したオリゴアニリン化合物1(18mg)及びリンタングステン酸(関東化学(株)製)(89mg)の混合物に、窒素循環型グローブボックス内で1,3−ジメチルイミダゾリジノン(2g)を加えて、50℃で加熱攪拌して、溶解させた。これにシクロヘキサノール(2g)を加えて攪拌し、緑色溶液を得た。この溶液を孔径0.2μmのシリンジフィルターでろ過して、電荷輸送性ワニスAを得た。
ポリマー1のかわりにポリマー2を用いた以外は、実施例1と同様の方法で電荷輸送性ワニスBを得た。
ポリマー1を用いず、オリゴアニリン化合物1及びリンタングステン酸の使用量を、20mg及び100mgとした以外は、実施例1と同様の方法で電荷輸送性ワニスCを得た。
電気特性を評価する際の基板には、インジウム錫酸化物が表面上に膜厚150nmでパターニングされた25mm×25mm×0.7tのガラス基板(以下ITO基板と略す)を用いた。ITO基板は、O2プラズマ洗浄装置(150W、30秒間)を用いて、表面上の不純物を除去してから使用した。
実施例1で得られた電荷輸送性ワニスAを、スピンコーターを用いてITO基板に塗布した後、80℃で1分間乾燥し、更に230℃で15分間焼成し、ITO基板上に30nmの均一な薄膜を形成した。
次いで、薄膜を形成したITO基板に対し、蒸着装置(真空度1.0×10-5Pa)を用いてトリス(8−キノリノラート)アルミニウム(III)(Alq3)、フッ化リチウム、及びアルミニウムの薄膜を順次積層し、OLED素子を得た。この際、蒸着レートは、Alq3及びアルミニウムについては0.2nm/秒、フッ化リチウムについては0.02nm/秒の条件でそれぞれ行い、膜厚は、それぞれ40nm、0.5nm及び100nmとした。
なお、空気中の酸素、水等の影響による特性劣化を防止するため、OLED素子は封止基板により封止した後、その特性を評価した。封止は、以下の手順で行った。
酸素濃度2ppm以下、露点−85℃以下の窒素雰囲気中で、有機EL素子を封止基板の間に収め、封止基板を接着材(ナガセケムテックス(株)製、XNR5516Z-B1)により貼り合わせた。この際、捕水剤(ダイニック(株)製、HD-071010W-40)をOLED素子と共に封止基板内に収めた。
貼り合わせた封止基板に対し、UV光を照射(波長:365nm、照射量:6,000mJ/cm2)した後、80℃で1時間、アニーリング処理して接着材を硬化させた。
電荷輸送性ワニスAのかわりに実施例2で得られた電荷輸送性ワニスBを用いた以外は、実施例3と同様の方法でOLED素子を作製した。
電荷輸送性ワニスAのかわりに比較例1で得られた電荷輸送性ワニスCを用いた以外は、実施例3と同様の方法でOLED素子を作製した。
Claims (17)
- 下記式(1)で表される繰り返し単位を与えるフルオレン誘導体と、下記式(2)で表される繰り返し単位を与えるフルオレン誘導体と、下記式(3)で表される繰り返し単位を与えるフルオレン誘導体との縮合重合体であることを特徴とするフッ素原子含有重合体。
R3及びR4は、それぞれ独立に、非共役系の2価の有機基を表し;
R5は、水素原子、又は少なくとも1つの水素原子がフッ素原子で置換されていてもよい、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基、炭素数8〜20のアルキルアラルキル基、炭素数2〜20のヘテロアリール基、炭素数6〜20のアリールオキシ基若しくは炭素数2〜20のヘテロアリールオキシ基を表し;
R6は、少なくとも1つの水素原子がフッ素原子で置換された、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基、炭素数8〜20のアルキルアラルキル基、炭素数2〜20のヘテロアリール基、炭素数6〜20のアリールオキシ基又は炭素数2〜20のヘテロアリールオキシ基を表し;
Rは、それぞれ独立に、ハロゲン原子、ニトロ基、シアノ基、Z1で置換されていてもよい、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基若しくは炭素数2〜20のアルキニルオキシ基、又はZ2で置換されていてもよい、炭素数6〜20のアリール基、炭素数2〜20のヘテロアリール基、炭素数6〜20のアリールオキシ基若しくは炭素数2〜20のヘテロアリールオキシ基を表し;
Z1は、ハロゲン原子、ニトロ基、シアノ基、又はZ3で置換されていてもよい、炭素数6〜20のアリール基、炭素数2〜20のヘテロアリール基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基若しくは炭素数2〜20のヘテロアリール基を表し;
Z2は、ハロゲン原子、ニトロ基、シアノ基、又はZ3で置換されていてもよい、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基若しくは炭素数2〜20のヘテロアリール基を表し;
Z3は、ハロゲン原子、ニトロ基又はシアノ基を表し;
p及びqは、それぞれ独立に、0又は1を表す。] - 重量平均分子量が、1,000〜200,000である請求項1記載の重合体。
- R1及びR2が、ともに炭素数1〜20のアルキル基又はともに少なくとも1つのエーテル構造を含む炭素数2〜20のアルキル基である請求項1又は2記載の重合体。
- R3及びR4が、−Rc−Ar−(式中、Rcは、炭素数1〜20のアルキレン基を表し、Arは、炭素数6〜20のアリーレン基を表す。)である請求項1〜3のいずれか1項記載の重合体。
- R5が、少なくとも1つの水素原子がフッ素原子で置換された、炭素数1〜20のアルキル基、炭素数2〜20のアルケニル基、炭素数2〜20のアルキニル基、炭素数1〜20のアルコキシ基、炭素数2〜20のアルケニルオキシ基、炭素数2〜20のアルキニルオキシ基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基、炭素数8〜20のアルキルアラルキル基、炭素数2〜20のヘテロアリール基、炭素数6〜20のアリールオキシ基又は炭素数2〜20のヘテロアリールオキシ基である請求項1〜4のいずれか1項記載の重合体。
- 請求項1〜5のいずれか1項記載の重合体からなる電荷輸送性物質。
- 請求項6記載の電荷輸送性物質、フッ素原子を含有しない電荷輸送性物質、ヘテロポリ酸からなるドーパント、及び有機溶媒を含む電荷輸送性ワニス。
- 前記フッ素原子を含有しない電荷輸送性物質が、アニリン誘導体である請求項7記載の電荷輸送性ワニス。
- 請求項7又は8記載の電荷輸送性ワニスを用いて作製される電荷輸送性薄膜。
- 請求項9記載の電荷輸送性薄膜を有する電子デバイス。
- 請求項9記載の電荷輸送性薄膜を有する有機エレクトロルミネッセンス素子。
- 請求項7又は8記載の電荷輸送性ワニスを基材上に塗布し、溶媒を蒸発させることを特徴とする電荷輸送性薄膜の製造方法。
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