JP5371404B2 - 電子輸送性材料および発光素子 - Google Patents
電子輸送性材料および発光素子 Download PDFInfo
- Publication number
- JP5371404B2 JP5371404B2 JP2008315065A JP2008315065A JP5371404B2 JP 5371404 B2 JP5371404 B2 JP 5371404B2 JP 2008315065 A JP2008315065 A JP 2008315065A JP 2008315065 A JP2008315065 A JP 2008315065A JP 5371404 B2 JP5371404 B2 JP 5371404B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- light emitting
- electron
- light
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000463 material Substances 0.000 title claims abstract description 234
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 23
- 239000011737 fluorine Substances 0.000 claims abstract description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000004065 semiconductor Substances 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000010409 thin film Substances 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 239000010419 fine particle Substances 0.000 claims description 3
- 239000002073 nanorod Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 239000002070 nanowire Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 232
- 239000011799 hole material Substances 0.000 description 89
- 239000010408 film Substances 0.000 description 73
- 150000001875 compounds Chemical class 0.000 description 41
- 238000000034 method Methods 0.000 description 40
- 239000000758 substrate Substances 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 238000002347 injection Methods 0.000 description 33
- 239000007924 injection Substances 0.000 description 33
- 230000005525 hole transport Effects 0.000 description 26
- -1 oligothiophene Chemical compound 0.000 description 25
- 229910052751 metal Inorganic materials 0.000 description 24
- 239000002019 doping agent Substances 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 17
- 238000007740 vapor deposition Methods 0.000 description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 15
- 238000007639 printing Methods 0.000 description 15
- 238000000576 coating method Methods 0.000 description 13
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 13
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- 239000002096 quantum dot Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000000903 blocking effect Effects 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000001771 vacuum deposition Methods 0.000 description 10
- 229940126062 Compound A Drugs 0.000 description 9
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 239000002131 composite material Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 238000002161 passivation Methods 0.000 description 9
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 238000004544 sputter deposition Methods 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 150000001342 alkaline earth metals Chemical class 0.000 description 7
- 230000004888 barrier function Effects 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000000295 emission spectrum Methods 0.000 description 5
- 239000011888 foil Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000002861 polymer material Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 4
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 4
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010030 laminating Methods 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 4
- 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 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910000085 borane Inorganic materials 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- NJWNEWQMQCGRDO-UHFFFAOYSA-N indium zinc Chemical compound [Zn].[In] NJWNEWQMQCGRDO-UHFFFAOYSA-N 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 238000007733 ion plating Methods 0.000 description 3
- 238000007644 letterpress printing Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 3
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052761 rare earth metal Inorganic materials 0.000 description 3
- 150000002910 rare earth metals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 3
- 229910001930 tungsten oxide Inorganic materials 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 2
- CEBWCJILGIWCOV-UHFFFAOYSA-N 4-(4-carboxy-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluorobenzoic acid Chemical compound FC1=C(F)C(C(=O)O)=C(F)C(F)=C1C1=C(F)C(F)=C(C(O)=O)C(F)=C1F CEBWCJILGIWCOV-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QNPULLWMVWOJAM-UHFFFAOYSA-N CC(C)(C)C1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)C(C)(C)C)C1=C(F)C(F)=C(C(F)=C1F)C1=C(F)C(F)=C(C(F)=C1F)C1=NC(=NC(=N1)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C Chemical group CC(C)(C)C1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC=C(C=C1)C(C)(C)C)C1=C(F)C(F)=C(C(F)=C1F)C1=C(F)C(F)=C(C(F)=C1F)C1=NC(=NC(=N1)C1=CC=C(C=C1)C(C)(C)C)C1=CC=C(C=C1)C(C)(C)C QNPULLWMVWOJAM-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000001755 magnetron sputter deposition Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- VRRYFSUFPWWZEM-UHFFFAOYSA-N phenyl-di(pyren-1-yl)phosphane Chemical compound C1=CC=CC=C1P(C=1C2=CC=C3C=CC=C4C=CC(C2=C43)=CC=1)C1=CC=C(C=C2)C3=C4C2=CC=CC4=CC=C13 VRRYFSUFPWWZEM-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000002061 vacuum sublimation Methods 0.000 description 2
- 229910001935 vanadium oxide Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 1
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- ZVWGMEDAEBTUIW-UHFFFAOYSA-N 3,10-diphenyloctacyclo[13.12.2.116,20.02,11.04,9.012,28.025,29.024,30]triaconta-1(28),2,4,6,8,10,12,14,16,18,20(30),21,23,25(29),26-pentadecaene Chemical group C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C=6C=CC=C7C=CC=C(C=67)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 ZVWGMEDAEBTUIW-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- PTBXOARBTPRBHN-UHFFFAOYSA-N 4-oxo-7h-thieno[2,3-b]pyridine-5-carboxylic acid Chemical compound O=C1C(C(=O)O)=CNC2=C1C=CS2 PTBXOARBTPRBHN-UHFFFAOYSA-N 0.000 description 1
- IPPWLNAOSSMFHW-UHFFFAOYSA-N 9-(4-ethenylphenyl)carbazole Chemical compound C1=CC(C=C)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 IPPWLNAOSSMFHW-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910016569 AlF 3 Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- QXNZFJSGYVMFCX-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3N(C1=2)C=CC=C Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C1=2)C=CC=C QXNZFJSGYVMFCX-UHFFFAOYSA-N 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910000881 Cu alloy Inorganic materials 0.000 description 1
- 229910000640 Fe alloy Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 240000002329 Inga feuillei Species 0.000 description 1
- 229910001374 Invar Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910001093 Zr alloy Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 230000032900 absorption of visible light Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000004840 adhesive resin Substances 0.000 description 1
- 229920006223 adhesive resin Polymers 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229910003481 amorphous carbon Inorganic materials 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- RHZWSUVWRRXEJF-UHFFFAOYSA-N indium tin Chemical compound [In].[Sn] RHZWSUVWRRXEJF-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000002650 laminated plastic Substances 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000007567 mass-production technique Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000005300 metallic glass Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910003465 moissanite Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 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
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
Images
Landscapes
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Description
2,2’,2’’−(1,3,5−ベンゼントリイル)−トリス(1−フェニル−1−H−ベンズイミダゾール)(TPBIと略)、またはトリアジン誘導体(特許文献1〜3)等の含窒素ヘテロ環化合物等が用いられている。しかし、これらの材料は平面的な分子構造で蒸着膜が結晶化し易く安定性が不十分な場合が多かった。また、溶液中では結晶化し易いために湿式成膜ができない場合が多かった。そのため、真空蒸着ができるだけでなく湿式成膜法を適用した場合においても平滑な膜が成膜できる高アモルファス性の電子輸送材料で、かつガラス転移温度が150℃以上の高耐熱性を有する材料が求められている。
Seth Coe,Wing-Keung Woo,Moungi Bawendland Vladlmir Bulovic, Nature,Vol402,800(2002). Sumit Chaudhary,Mihrimah Ozkan andWarren C.W.Chan, Applied physics letters,84,2925 (2004). M.Anni,L.Manna,R.Cingolani,D.Valerini,A.Creti and m.Lomascolo,Applied physics letters,85,4169(2004). Yanqin Li,Aurora Rizzo,Marco Mazzeo,Luigi Carbone, Liberato Manna,Roberto Cingolani and Giuseppe Gigli, Applied physics letters,97,113501(2005). Peter T.Kazlas, Jonathan S. Steckel, Marshall Cox, Caroline Roush, Dorai ramprasad, Craig Breen, Mead Misic,Vincent diFilippo, Maria Anc, John Ritter,and Seth Coe-Sullivan,SID07 DIGEST P-176(2007). Takashi Hirano,keisuke matsuo, Kokichi Kohinata, Koji Hanawa, Tatsuya Matsumi,Eisuke Matsuda, Ryoko Matsuura, Tadashi Ishibashi, Akihiko Yoshida, and Tatsuya Sasaoka, SID07 DIGEST 53.2(2007). M.Masuichi,M.Kawagoe,Y.Takamura,H.Adachi,Y,Fujimoto, and M.Ueno,SID05, DIGEST,30.1(2005). W.F.Feehery,SID07 DIGEST, 69.1(2007). T.FUNAMOTO, Y. Matsueda, O. Yokoyama, A. Tsuda, H. Takeshita, A. Miyashita, SID 02 DIGEST, 27.5L(2002). T. Shimoda, SID 03 DIGEST, 39.1(2003). David Albertalli, SID 05 DIGEST, 30.3(2005). Tadashi Gohda, Yuhki Kobayashi, Kiyoshi Okano, Satoshi Inoue, Ken Okamoto,Satoshi Hashimoto, Emi Yamamoto, Haruyuki Morita, Seiichi Mitsui and Mitsuhiro Koden, SID 06 DIGEST, 58.3(2006). E. Kitazume, K. Takeshita, K. Murata, Y. Qian, Y. Abe, M. Yokoo, K. Oota, T. Taguchi,SID06DIGEST, 41.2(2006).
の構造で示される電子輸送性材料が提供される。
で示される化合物が提供される。
の構造で示されることを特徴とした電子輸送性材料が好ましい。
CdO、In2O3、SnO2、TiO2、SiC等の無機半導体をベースとする無機半導体の薄膜、または例えば直径10nm以下の無機半導体の微粒子や、例えば直径数nmから数百nmの無機半導体のナノロッドやナノワイヤ等の無機発光材料を含むこともできる。これら無機材料としては、背景技術に記載したような塗布可能な無機半導体の量子ドット発光材料を好ましく用いることができる。例えば、CdSeの直径2〜6nm程度の半導体ナノ粒子からなるコア(核)の周囲にZnSをエピタキシャル成長させ励起子閉じ込め用のシェル(殻)とし、さらに表面をトリオクチルホスフィンオキサイド等の鎖状分子で修飾し有機溶媒に分散可能にした材料である。
本発明の式(1)の電子輸送性材料は単独で湿式成膜性を有しており、また、実質的に可視光を吸収しないことから、発光層に用いる場合はホスト材料として用いることができる。具体的には表1のX1からX5と表2のY1からY45の任意の組み合わせの材料を用いることができる。
また、逆に本発明の電子輸送性材料を電子輸送性ドーパントとして用い、他の低分子および高分子発光材料や発光層用ホスト材料に5〜50wt%未満の濃度でドープすることもできる。
4,4’−ビス{2,4−ビス(4−tert−ブチルフェニル)−1,3,5−トリアジン−6−イル}−2,2’,3,3’,5,5’,6,6’−オクタフルオロビフェニル(化合物A)の合成
(中間体合成例1)
2,2’,3,3’,5,5’,6,6’−オクタフルオロビフェニル−4,4’−ジカルボン酸の合成
アルゴン雰囲気下、2,2’,3,3’,5,5’,6,6’−オクタフルオロビフェニル5.0g(16.8mmol)を脱水テトラヒドロフラン55mLに溶解した後、−70℃以下に冷却した。ここに1.6Mのn−ブチルリチウムのヘキサン溶液21ml(33.6mmol)を滴下し、同温度で1時間攪拌して熟成した。アニオン化終了後、−70℃で二酸化炭素をバブリングしながら5時間攪拌した。さらに室温に戻し12時間攪拌した。
2,2’,3,3’,5,5’,6,6’−オクタフルオロビフェニル−4,4’−ジカルボン酸クロリドの合成
2,2’,3,3’,5,5’,6,6’−オクタフルオロビフェニル−4,4’−ジカルボン酸4.0g(10.4mmol)と塩化チオニル12mlからなる懸濁液にN−ジメチルホルムアミド1〜2mlを加え、反応系が均一になるまで14時間還流攪拌した。
(合成例)
4,4’−ビス{2,4−ビス(4−tert−ブチルフェニル)−1,3,5−トリアジン−6−イル}−2,2’,3,3’,5,5’,6,6’−オクタフルオロビフェニル(化合物A)の合成
アルゴン雰囲気下、4−tert−ブチル−ベンゾ二トリル6.39g(40.2mmol)、2,2’,3,3’,5,5’,6,6’−オクタフルオロビフェニル−4,4’−ジカルボン酸クロリド4.05g(9.6mmol)およびクロロホルム40mlからなる溶液を0〜−5℃に冷却した。ここに5塩化アンチモン5.72g(19.1mmol)を滴下し、1時間掛けて徐々に室温に戻した。さらに、反応混合物を8時間還流攪拌した後、反応系内から減圧下で溶媒を留去し、オキサジアニウム塩を得た。このオキサジアニウムを粉砕し、0℃に冷却した後、攪拌下、28%アンモニア水100mlを滴下し、徐々に室温に戻しながら12時間攪拌した。
19F−NMR:(376MHz,d−CDCl3):δ:137(s、4F)、140(s、4F)
<化合物Aの吸収スペクトル>
化合物A30mgをバックスメタル社製Bu−6Moボートに入れ、真空蒸着装置にセットし1E−5Torr下385℃に通電加熱して、石英板上で約59nmの厚さで蒸着を行なうことにより、平滑で透明なアモルファス膜が得られた。この膜を島津社製UV−3600分光光度計で吸収スペクトルを測定した結果を図6に示す。吸収端波長375nm(3.31eV)で可視光の吸収が無かった。
化合物Aのガラス転移温度(Tg)と融点(Tm)を、セイコー電子工業製EXSTAR6000シリーズDSC6220により測定した。20℃/分の条件で昇温してTmは350℃〜364℃(ピーク365℃)であった。急冷し再度昇温しTgを測定した結果、Tgは177℃(転移始め)〜192℃(転移終わり)であった。
化合物Aは、室温でトルエン1mlに0.1gの濃度まで溶解し、インク化することが容易であった。
トルエンに1wt%の濃度で溶かしスピンコート成膜が可能で透明で平滑な膜が得られた。
化合物Aを1mlのトルエンに20mg溶解し、1000rpmでITO透明電極ガラス上にスピンコートし、住友重機械アドバンストマシナリー製イオン化ポテンシャル測定装置にてイオン化エネルギーを測定した結果、7.33eVであった。
厚さ0.7mmのガラス基板1上に、マグネトロンスパッタリング法により厚さ150nmのITO膜を成膜し陽極2とする。常法によりウエットエッチングを行い、ITO膜をパターニングした。この基板をアルカリ洗剤により超音波洗浄した後、さらに純水で洗浄し、乾燥させ、紫外線洗浄を行った。
実施例2と同様に電子ブロック正孔輸送層10までを形成した後に、式(A)の化合物中に式(M)で示すFirpicを8mol%の濃度で混合し、トルエンに約2wt%の濃度で溶かしたインクをスピンコート法により80nmの厚さで成膜して、不要な部分を拭き取り真空加熱乾燥し発光層4とした。
実施例2と同様に電子ブロック正孔輸送層10までを形成した後に、化合物(A)と2nmのCdSeを核としZnSを殻にした量子ドットと、トリオクチルホスフィンオキサイドとトリオクチルホスフィンでキャップした青色発光コロイド粒子とを重量比1:5で混合したクロロホルム溶液をインクジェット法により発光層4として80nmの厚さで積層し窒素中300℃でアニールした。
厚さ1mmのp型シリコン基板1をアルカリ洗剤により超音波洗浄した後、さらに純水で洗浄し、乾燥させ、紫外線洗浄を行った。
実施例2と同様に電子ブロック正孔輸送層までを形成した後に、式(H)で示す化合物と、式(Z)の正孔輸送性高分子青色発光材料と、電子輸送材料としてトリス(2,4,6−トリメチル−3−(ピリジル−3−イル)フェニル)ボランを重量比6:2:2で混合した固形分2wt%のトルエンインクをスピンコート法により成膜して不要な部分を拭き取り、真空加熱乾燥し、80nmの厚さの発光層4とした。
実施例6の式(H)で示す化合物に換えて表1のX3と表2のY1の組み合わせの化合物を用いた素子を作製し、同様に青色発光が得られる。
実施例4において、正孔ブロック電子輸送層11と電子輸送層12を除いた以外、同様の素子を作製した。この素子に12Vの直流電圧を印加すると、実施例6の素子に比べ電流密度が増大するが、発光はほとんど得られない。
実施例5において、正孔ブロック電子輸送層11と電子輸送層12を除いた以外、同様の素子を作製した。この素子に12Vの直流電圧を印加すると、実施例6の素子に比べ電流密度が増大するが、発光はほとんど得られない。
2…陽極
3…正孔注入層
4…発光層
5…陰極
6…配線
7…電源
8…端子部
9…配線
10…電子ブロック正孔輸送層
11…正孔ブロック電子輸送層
12…電子輸送層
13…パッシベーション層
14…封止板
15…接着材料
26…レジスト隔壁
27…赤色発光層
28…緑色発光層
29…青色発光層
Claims (7)
- 有機溶媒中に、請求項1〜3のいずれか一項に記載の電子輸送性材料を少なくとも1種以上を含むことを特徴とするインク組成物。
- 請求項1〜3のいずれか一項に記載の材料に加えて、他の種類のキャリア輸送材料および発光材料を少なくとも1種以上含むことを特徴とする請求項4に記載のインク組成物。
- 対向する電極間若しくは陽極と陰極との間の少なくとも1層に有機または無機の発光材料を含有する発光素子において、前記対向する電極間若しくは陽極と陰極との間に形成された少なくとも1層が請求項1〜3のいずれか一項に記載の電子輸送性材料を含むことを特徴とする発光素子。
- 前記無機の発光材料が無機半導体の薄膜、または無機半導体微粒子、または無機半導体からなるナノロッド若しくはナノワイヤを含有する発光素子であることを特徴とする請求項6に記載の発光素子。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008315065A JP5371404B2 (ja) | 2008-12-10 | 2008-12-10 | 電子輸送性材料および発光素子 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008315065A JP5371404B2 (ja) | 2008-12-10 | 2008-12-10 | 電子輸送性材料および発光素子 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010141059A JP2010141059A (ja) | 2010-06-24 |
JP5371404B2 true JP5371404B2 (ja) | 2013-12-18 |
Family
ID=42350949
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008315065A Expired - Fee Related JP5371404B2 (ja) | 2008-12-10 | 2008-12-10 | 電子輸送性材料および発光素子 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5371404B2 (ja) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012013272A1 (en) | 2010-07-26 | 2012-02-02 | Merck Patent Gmbh | Quantum dots and hosts |
EP2676305A4 (en) * | 2011-02-14 | 2015-11-11 | Du Pont | ELECTROACTIVE COMPOSITION |
JP5664311B2 (ja) * | 2011-02-15 | 2015-02-04 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子 |
TWI462917B (zh) * | 2012-02-27 | 2014-12-01 | Lg Chemical Ltd | 有機發光二極體 |
JP6007126B2 (ja) * | 2012-02-29 | 2016-10-12 | 株式会社半導体エネルギー研究所 | フルオレン化合物、発光素子、発光装置、電子機器、および照明装置 |
JP2014049696A (ja) * | 2012-09-03 | 2014-03-17 | Nippon Hoso Kyokai <Nhk> | 有機電界発光素子 |
US9614191B2 (en) | 2013-01-17 | 2017-04-04 | Kateeva, Inc. | High resolution organic light-emitting diode devices, displays, and related methods |
US9444050B2 (en) | 2013-01-17 | 2016-09-13 | Kateeva, Inc. | High resolution organic light-emitting diode devices, displays, and related method |
US10665786B2 (en) | 2013-03-08 | 2020-05-26 | Hitachi Chemical Company, Ltd. | Treatment liquid containing ionic compound, organic electronic element, and method for producing organic electronic element |
JP6252829B2 (ja) * | 2013-07-12 | 2017-12-27 | 凸版印刷株式会社 | 電荷輸送ポリマー、ならびにそれを用いた電荷輸送ポリマー組成物、発光性電荷輸送膜および有機el素子 |
KR102665000B1 (ko) | 2013-08-14 | 2024-05-10 | 가부시키가이샤 큐럭스 | 유기 일렉트로루미네선스 소자 |
JP6768534B2 (ja) * | 2016-07-20 | 2020-10-14 | 株式会社Joled | 有機電界発光素子、有機電界発光装置および電子機器 |
JP2018022862A (ja) * | 2016-07-20 | 2018-02-08 | 株式会社Joled | 有機電界発光素子、有機電界発光装置および電子機器 |
JP2020126795A (ja) * | 2019-02-06 | 2020-08-20 | 日本放送協会 | 量子ドット発光素子及び表示装置 |
CN115094458A (zh) * | 2021-05-26 | 2022-09-23 | 山东省科学院能源研究所 | 一种Cu掺杂NiO空穴传输层薄膜与制备方法及应用 |
WO2024028965A1 (ja) * | 2022-08-02 | 2024-02-08 | シャープディスプレイテクノロジー株式会社 | 発光素子、表示装置、および発光素子の製造方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6229012B1 (en) * | 1998-10-01 | 2001-05-08 | Xerox Corporation | Triazine compositions |
US6057048A (en) * | 1998-10-01 | 2000-05-02 | Xerox Corporation | Electroluminescent (EL) devices |
US6225467B1 (en) * | 2000-01-21 | 2001-05-01 | Xerox Corporation | Electroluminescent (EL) devices |
US7169482B2 (en) * | 2002-07-26 | 2007-01-30 | Lg.Philips Lcd Co., Ltd. | Display device with anthracene and triazine derivatives |
KR100670778B1 (ko) * | 2004-10-11 | 2007-01-17 | 한국전자통신연구원 | 트리아진 그룹을 갖는 유기 반도체 소자용 화합물과, 이를포함하는 유기 반도체 박막 및 유기 반도체 소자와,이들의 제조 방법 |
JP2006225321A (ja) * | 2005-02-17 | 2006-08-31 | Tosoh Corp | 1,3,5−トリアジン誘導体からなる薄膜及び製造方法 |
JP4907090B2 (ja) * | 2005-02-17 | 2012-03-28 | 東ソー株式会社 | 1,3,5−トリアジン誘導体 |
JP4878819B2 (ja) * | 2005-11-18 | 2012-02-15 | ケミプロ化成株式会社 | 新規なトリアジン誘導体およびそれを含む有機エレクトロルミネッセンス素子 |
-
2008
- 2008-12-10 JP JP2008315065A patent/JP5371404B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2010141059A (ja) | 2010-06-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5371404B2 (ja) | 電子輸送性材料および発光素子 | |
KR101311934B1 (ko) | 유기광전소자용 조성물 및 이를 이용한 유기광전소자 | |
KR101974233B1 (ko) | 유기 전계 발광 소자 | |
JP7431162B2 (ja) | 有機電界発光素子 | |
KR101247626B1 (ko) | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 | |
JP5742092B2 (ja) | 有機化合物、電荷輸送材料、有機電界発光素子用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 | |
KR101373587B1 (ko) | 용액공정용 나프틸페닐 유도체 및 이를 채용한 유기 전계 발광 소자 | |
KR20160101908A (ko) | 이리듐 착물 화합물, 그 화합물의 제조 방법, 그 화합물을 함유하는 조성물, 유기 전계 발광 소자, 표시 장치 및 조명 장치 | |
CN110838549B (zh) | 一种基于激基复合物和激基缔合物体系的有机电致发光器件 | |
JP2009191232A (ja) | 蛍光性化合物、発光性インク組成物および有機el素子 | |
KR20150040912A (ko) | 이리듐 착물 화합물, 그리고 그 화합물을 포함하는 조성물, 유기 전계 발광 소자, 표시 장치 및 조명 장치 | |
WO2011024922A1 (ja) | モノアミン化合物、電荷輸送材料、電荷輸送膜用組成物、有機電界発光素子、有機el表示装置及び有機el照明 | |
JP2009194042A (ja) | カルバゾリル基を含有する有機エレクトロルミネッセンス素子用電荷輸送材料およびその用途 | |
KR20100075079A (ko) | 신규한 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 | |
KR101831270B1 (ko) | 유기전계발광소자 | |
JP5669539B2 (ja) | キノリノ[3,2,1−kl]フェノキサジン化合物及びこれを用いた有機発光素子 | |
KR102152012B1 (ko) | 형광 화합물 및 이를 이용한 유기발광다이오드소자 | |
KR101297162B1 (ko) | 유기광전소자용 조성물 및 이를 이용한 유기광전소자 | |
CN110857296A (zh) | 具有空穴阻挡层的有机电致发光器件 | |
JP5617202B2 (ja) | 有機化合物、電荷輸送材料、有機電界発光素子用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 | |
KR20160047297A (ko) | 유기 전계 발광 소자 | |
KR20150077587A (ko) | 유기 전계 발광 소자 | |
KR20160076461A (ko) | 유기 전계 발광 소자 | |
US20240147833A1 (en) | Iridium Complex Compound, Iridium Complex Compound-Containing Composition, Organic Electroluminescent Element, and Method for Manufacturing the Same | |
JP4802671B2 (ja) | 低分子有機薄膜を備える有機el素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20111118 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130704 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130820 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130917 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5371404 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |