CN107698531B - 化合物及其有机电子装置 - Google Patents
化合物及其有机电子装置 Download PDFInfo
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- CN107698531B CN107698531B CN201710674271.9A CN201710674271A CN107698531B CN 107698531 B CN107698531 B CN 107698531B CN 201710674271 A CN201710674271 A CN 201710674271A CN 107698531 B CN107698531 B CN 107698531B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
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- 239000012044 organic layer Substances 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 230000000903 blocking effect Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000000543 intermediate Substances 0.000 description 104
- 125000004432 carbon atom Chemical group C* 0.000 description 55
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- 239000000463 material Substances 0.000 description 26
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- 229910052799 carbon Inorganic materials 0.000 description 24
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- 238000006243 chemical reaction Methods 0.000 description 17
- 125000000524 functional group Chemical group 0.000 description 17
- 239000000376 reactant Substances 0.000 description 17
- 238000000434 field desorption mass spectrometry Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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- 229910052805 deuterium Inorganic materials 0.000 description 13
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- 125000000217 alkyl group Chemical group 0.000 description 10
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- 125000003545 alkoxy group Chemical group 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000013086 organic photovoltaic Methods 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical group C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 2
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- NVFINOHFZXRPAD-UHFFFAOYSA-N 9h-fluorene-1,2-diamine Chemical class C1=CC=C2CC3=C(N)C(N)=CC=C3C2=C1 NVFINOHFZXRPAD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KHNYNFUTFKJLDD-UHFFFAOYSA-N Benzo[j]fluoranthene Chemical group C1=CC(C=2C3=CC=CC=C3C=CC=22)=C3C2=CC=CC3=C1 KHNYNFUTFKJLDD-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
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- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 235000019270 ammonium chloride Nutrition 0.000 description 2
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- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- 125000001246 bromo group Chemical group Br* 0.000 description 2
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 2
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- 238000007738 vacuum evaporation Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
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- QSKOTJJXLLHWCA-UHFFFAOYSA-N 3-[3-[2-[3-[2-(3-pyridin-3-yl-2H-pyridin-3-yl)phenyl]phenyl]phenyl]-2H-pyridin-3-yl]pyridine Chemical compound N=1CC(C=CC1)(C=1C=CC=NC1)C1=C(C=CC=C1)C1=CC(=CC=C1)C1=C(C=CC=C1)C1(CN=CC=C1)C=1C=CC=NC1 QSKOTJJXLLHWCA-UHFFFAOYSA-N 0.000 description 1
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- FHFJGNMPGCZWCW-UHFFFAOYSA-N 5,14-dibromotricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-one Chemical compound Brc1ccc2ccc3ccc(Br)cc3c(=O)c2c1 FHFJGNMPGCZWCW-UHFFFAOYSA-N 0.000 description 1
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Images
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/625—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
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- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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Abstract
Description
Claims (9)
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US201662372417P | 2016-08-09 | 2016-08-09 | |
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CN107698531A (zh) | 2018-02-16 |
US10693075B2 (en) | 2020-06-23 |
TWI644911B (zh) | 2018-12-21 |
KR101956660B1 (ko) | 2019-03-11 |
JP2018058823A (ja) | 2018-04-12 |
JP6498243B2 (ja) | 2019-04-10 |
US20180047918A1 (en) | 2018-02-15 |
CN107698570A (zh) | 2018-02-16 |
US10454039B2 (en) | 2019-10-22 |
KR20180018380A (ko) | 2018-02-21 |
TW201811774A (zh) | 2018-04-01 |
JP2018052919A (ja) | 2018-04-05 |
JP6475795B2 (ja) | 2019-02-27 |
KR101963675B1 (ko) | 2019-03-29 |
KR20180018381A (ko) | 2018-02-21 |
TWI644884B (zh) | 2018-12-21 |
TW201811719A (zh) | 2018-04-01 |
US20180047907A1 (en) | 2018-02-15 |
CN107698570B (zh) | 2021-02-23 |
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