JP2017178832A - 自己組織化し得る多環式芳香族化合物およびそれを用いた有機el素子 - Google Patents
自己組織化し得る多環式芳香族化合物およびそれを用いた有機el素子 Download PDFInfo
- Publication number
- JP2017178832A JP2017178832A JP2016067018A JP2016067018A JP2017178832A JP 2017178832 A JP2017178832 A JP 2017178832A JP 2016067018 A JP2016067018 A JP 2016067018A JP 2016067018 A JP2016067018 A JP 2016067018A JP 2017178832 A JP2017178832 A JP 2017178832A
- Authority
- JP
- Japan
- Prior art keywords
- derivatives
- group
- organic
- bis
- polycyclic aromatic
- 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.)
- Granted
Links
- -1 polycyclic aromatic compound Chemical class 0.000 title claims abstract description 253
- 239000000463 material Substances 0.000 claims abstract description 123
- 125000003118 aryl group Chemical group 0.000 claims abstract description 84
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 79
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 65
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 39
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 5
- 239000010410 layer Substances 0.000 claims description 208
- 150000001875 compounds Chemical class 0.000 claims description 118
- 238000002347 injection Methods 0.000 claims description 72
- 239000007924 injection Substances 0.000 claims description 72
- 229910052757 nitrogen Inorganic materials 0.000 claims description 65
- 238000005401 electroluminescence Methods 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052751 metal Inorganic materials 0.000 claims description 27
- 239000002184 metal Substances 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 14
- 238000000151 deposition Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 10
- 150000002910 rare earth metals Chemical class 0.000 claims description 10
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 6
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 5
- 150000005041 phenanthrolines Chemical class 0.000 claims description 4
- 150000003222 pyridines Chemical class 0.000 claims description 4
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 3
- 150000008045 alkali metal halides Chemical class 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 229910001404 rare earth metal oxide Inorganic materials 0.000 claims description 3
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 229910001507 metal halide Inorganic materials 0.000 claims description 2
- 150000005309 metal halides Chemical class 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 230000008859 change Effects 0.000 abstract description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 216
- 239000000543 intermediate Substances 0.000 description 167
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 108
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- 239000000203 mixture Substances 0.000 description 70
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 47
- 238000000034 method Methods 0.000 description 46
- 239000012299 nitrogen atmosphere Substances 0.000 description 45
- 239000000758 substrate Substances 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 42
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 34
- 238000001816 cooling Methods 0.000 description 33
- 238000007740 vapor deposition Methods 0.000 description 33
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 30
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 28
- 238000001914 filtration Methods 0.000 description 28
- 230000005525 hole transport Effects 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 238000000137 annealing Methods 0.000 description 27
- 229910052782 aluminium Inorganic materials 0.000 description 26
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 25
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 24
- 239000010408 film Substances 0.000 description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 21
- 235000019798 tripotassium phosphate Nutrition 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 20
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 20
- 239000002244 precipitate Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 125000004093 cyano group Chemical group *C#N 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
- 125000001181 organosilyl group Chemical class [SiH3]* 0.000 description 13
- 230000008569 process Effects 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 11
- 230000008021 deposition Effects 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 229910052750 molybdenum Inorganic materials 0.000 description 11
- 239000011733 molybdenum Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000000859 sublimation Methods 0.000 description 11
- 230000008022 sublimation Effects 0.000 description 11
- 125000003107 substituted aryl group Chemical group 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 10
- 235000011056 potassium acetate Nutrition 0.000 description 10
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 10
- 239000010409 thin film Substances 0.000 description 10
- 239000004305 biphenyl Substances 0.000 description 9
- 229910052792 caesium Inorganic materials 0.000 description 9
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 9
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 9
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000011159 matrix material Substances 0.000 description 8
- 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 8
- 229910052709 silver Inorganic materials 0.000 description 8
- 239000004332 silver Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 150000004775 coumarins Chemical class 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 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 7
- 230000003993 interaction Effects 0.000 description 7
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- IQTHEAQKKVAXGV-UHFFFAOYSA-N 4-ditert-butylphosphanyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1 IQTHEAQKKVAXGV-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 6
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- 0 CC(C)N([Al]*)[Al]* Chemical compound CC(C)N([Al]*)[Al]* 0.000 description 5
- 101150003085 Pdcl gene Proteins 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 150000001556 benzimidazoles Chemical class 0.000 description 5
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 5
- CVKBMWWNKUWISK-UHFFFAOYSA-L dichloromethane;dichloropalladium Chemical compound ClCCl.Cl[Pd]Cl CVKBMWWNKUWISK-UHFFFAOYSA-L 0.000 description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 5
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 150000004880 oxines Chemical class 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000001338 self-assembly Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 4
- NQMRYYAAICMHPE-UHFFFAOYSA-N (4-methoxyphenyl)boron Chemical compound [B]C1=CC=C(OC)C=C1 NQMRYYAAICMHPE-UHFFFAOYSA-N 0.000 description 3
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 3
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 3
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 3
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000944 Soxhlet extraction Methods 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- JCGRMAWAPVVHFK-UHFFFAOYSA-N chrysene-6,12-diamine Chemical compound C1=CC=C2C(N)=CC3=C(C=CC=C4)C4=C(N)C=C3C2=C1 JCGRMAWAPVVHFK-UHFFFAOYSA-N 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920005596 polymer binder Polymers 0.000 description 3
- 239000002491 polymer binding agent Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003252 quinoxalines Chemical class 0.000 description 3
- 229910052701 rubidium Inorganic materials 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 150000003577 thiophenes Chemical class 0.000 description 3
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- MEENTMAAPFUEFN-UHFFFAOYSA-N 1-dodecyl-4-phenylbenzene Chemical group C1=CC(CCCCCCCCCCCC)=CC=C1C1=CC=CC=C1 MEENTMAAPFUEFN-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- KIIGPNDJMVHUSL-UHFFFAOYSA-N 1-phenyl-2-benzofuran Chemical compound C=12C=CC=CC2=COC=1C1=CC=CC=C1 KIIGPNDJMVHUSL-UHFFFAOYSA-N 0.000 description 2
- IVYAYAWSXINSEF-UHFFFAOYSA-N 1-tert-butylperylene Chemical group C1=CC(C=2C(C(C)(C)C)=CC=C3C=2C2=CC=C3)=C3C2=CC=CC3=C1 IVYAYAWSXINSEF-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical class C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- WLODWTPNUWYZKN-UHFFFAOYSA-N 1h-pyrrol-2-ol Chemical class OC1=CC=CN1 WLODWTPNUWYZKN-UHFFFAOYSA-N 0.000 description 2
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- FZTBAQBBLSYHJZ-UHFFFAOYSA-N 2-phenyl-1,3-oxazol-4-ol Chemical class OC1=COC(C=2C=CC=CC=2)=N1 FZTBAQBBLSYHJZ-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 2
- YWKDIAQEJCJKHU-UHFFFAOYSA-N 4-anthracen-9-ylphenol Chemical compound C1=CC(O)=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 YWKDIAQEJCJKHU-UHFFFAOYSA-N 0.000 description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- WBKMMYIUBMHNEU-UHFFFAOYSA-N 6-bromo-2-[4-[10-[4-(2-chloroquinolin-6-yl)phenyl]anthracen-9-yl]phenyl]quinoline Chemical compound BrC=1C=C2C=CC(=NC2=CC=1)C1=CC=C(C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC=C(C=C1)C=1C=C2C=CC(=NC2=CC=1)Cl WBKMMYIUBMHNEU-UHFFFAOYSA-N 0.000 description 2
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 2
- NINQBHWYJMTLQG-UHFFFAOYSA-N 9-(4-methoxyphenyl)anthracene Chemical compound C1=CC(OC)=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 NINQBHWYJMTLQG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KWHWFTSHDPJOTG-UHFFFAOYSA-N Deazaflavin Chemical class C1=CC=C2C=C(C(=O)NC(=O)N3)C3=NC2=C1 KWHWFTSHDPJOTG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- NYXIPJBBAPFGIR-UHFFFAOYSA-K [Al+3].C1(=CC=CC=C1)C=1C=C(C=CC1)[O-].C1(=CC=CC=C1)C=1C=C(C=CC1)[O-].C1(=CC=CC=C1)C=1C=C(C=CC1)[O-] Chemical compound [Al+3].C1(=CC=CC=C1)C=1C=C(C=CC1)[O-].C1(=CC=CC=C1)C=1C=C(C=CC1)[O-].C1(=CC=CC=C1)C=1C=C(C=CC1)[O-] NYXIPJBBAPFGIR-UHFFFAOYSA-K 0.000 description 2
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- VZSNNUDOANMGNX-UHFFFAOYSA-K aluminum;4-phenylphenolate Chemical compound [Al+3].C1=CC([O-])=CC=C1C1=CC=CC=C1.C1=CC([O-])=CC=C1C1=CC=CC=C1.C1=CC([O-])=CC=C1C1=CC=CC=C1 VZSNNUDOANMGNX-UHFFFAOYSA-K 0.000 description 2
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001543 aryl boronic acids Chemical class 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 125000003609 aryl vinyl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 150000001907 coumarones Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000012351 deprotecting agent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000007946 flavonol Chemical class 0.000 description 2
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 2
- 235000011957 flavonols Nutrition 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical class C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 230000009878 intermolecular interaction Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- MBHQEXPGNCWWBP-UHFFFAOYSA-M magnesium;dodecane;bromide Chemical compound [Mg+2].[Br-].CCCCCCCCCCC[CH2-] MBHQEXPGNCWWBP-UHFFFAOYSA-M 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 150000004893 oxazines Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 150000002988 phenazines Chemical class 0.000 description 2
- GRJHONXDTNBDTC-UHFFFAOYSA-N phenyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC=C1 GRJHONXDTNBDTC-UHFFFAOYSA-N 0.000 description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 229920002492 poly(sulfone) Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- OWJJRQSAIMYXQJ-UHFFFAOYSA-N pyrene-1,6-diamine Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=C(N)C=CC2=C1 OWJJRQSAIMYXQJ-UHFFFAOYSA-N 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 2
- 150000005255 pyrrolopyridines Chemical class 0.000 description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002356 single layer Substances 0.000 description 2
- 239000005361 soda-lime glass Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- CYIFVRUOHKNECG-UHFFFAOYSA-N tridecan-2-one Chemical compound CCCCCCCCCCCC(C)=O CYIFVRUOHKNECG-UHFFFAOYSA-N 0.000 description 2
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- 229960003986 tuaminoheptane Drugs 0.000 description 2
- YKSGNOMLAIJTLT-UHFFFAOYSA-N violanthrone Chemical class C12=C3C4=CC=C2C2=CC=CC=C2C(=O)C1=CC=C3C1=CC=C2C(=O)C3=CC=CC=C3C3=CC=C4C1=C32 YKSGNOMLAIJTLT-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- IDCZNRDLRHDFHY-UHFFFAOYSA-N (10-phenylanthracen-9-yl)-bis(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1B(C=1C2=CC=CC=C2C(C=2C=CC=CC=2)=C2C=CC=CC2=1)C1=C(C)C=C(C)C=C1C IDCZNRDLRHDFHY-UHFFFAOYSA-N 0.000 description 1
- APHLSUBLNQBFTM-UHFFFAOYSA-N (2-aminophenyl)-(4-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C(Cl)C=C1 APHLSUBLNQBFTM-UHFFFAOYSA-N 0.000 description 1
- MGZOXZPZHVOXQB-UHFFFAOYSA-N (2-oxochromen-7-yl) acetate Chemical class C1=CC(=O)OC2=CC(OC(=O)C)=CC=C21 MGZOXZPZHVOXQB-UHFFFAOYSA-N 0.000 description 1
- KXTPESAKEXMGAZ-UHFFFAOYSA-N (4,5-diphenylanthracen-9-yl)-bis(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1B(C=1C2=CC=CC(=C2C=C2C(C=3C=CC=CC=3)=CC=CC2=1)C=1C=CC=CC=1)C1=C(C)C=C(C)C=C1C KXTPESAKEXMGAZ-UHFFFAOYSA-N 0.000 description 1
- CXQWSAFVQFTRHW-UHFFFAOYSA-N (6-dodecylnaphthalen-2-yl) trifluoromethanesulfonate Chemical compound CCCCCCCCCCCCC1=CC2=C(C=C1)C=C(C=C2)OS(=O)(=O)C(F)(F)F CXQWSAFVQFTRHW-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-UHFFFAOYSA-N 0.000 description 1
- LBIUMLHTGBTILM-UHFFFAOYSA-N 1,3-bis(2-methylphenyl)-2-benzofuran Chemical compound CC1=CC=CC=C1C1=C2C=CC=CC2=C(C=2C(=CC=CC=2)C)O1 LBIUMLHTGBTILM-UHFFFAOYSA-N 0.000 description 1
- JGOKQJGYALJSMZ-UHFFFAOYSA-N 1,3-bis[2-(trifluoromethyl)phenyl]-2-benzofuran Chemical compound FC(F)(F)C1=CC=CC=C1C1=C2C=CC=CC2=C(C=2C(=CC=CC=2)C(F)(F)F)O1 JGOKQJGYALJSMZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UKSZBOKPHAQOMP-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1.C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 UKSZBOKPHAQOMP-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- MTCVUGLPXSUGEU-UHFFFAOYSA-N 1-N,6-diphenyl-1-N,6-N-bis(4-trimethylsilylphenyl)-3H-pyrene-1,6-diamine Chemical compound C1(=CC=CC=C1)C1(C=CC2=CC=C3C(=CCC4=CC=C1C2=C34)N(C1=CC=C(C=C1)[Si](C)(C)C)C1=CC=CC=C1)NC1=CC=C(C=C1)[Si](C)(C)C MTCVUGLPXSUGEU-UHFFFAOYSA-N 0.000 description 1
- AQHFAFUHJCEELC-UHFFFAOYSA-N 1-N,8-N-diphenyl-1-N,8-N-bis(4-phenylphenyl)pyrene-1,8-diamine Chemical compound C1(=CC=C(C=C1)N(C1=CC=C2C=CC3=CC=C(C4=CC=C1C2=C34)N(C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 AQHFAFUHJCEELC-UHFFFAOYSA-N 0.000 description 1
- PHBJYIUTTPNUBD-UHFFFAOYSA-N 1-[4-(10-naphthalen-2-ylanthracen-9-yl)phenyl]-2-phenylbenzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1C1=CC=C(C=2C3=CC=CC=C3C(C=3C=C4C=CC=CC4=CC=3)=C3C=CC=CC3=2)C=C1 PHBJYIUTTPNUBD-UHFFFAOYSA-N 0.000 description 1
- DEKWFUNEGAIOKS-UHFFFAOYSA-N 1-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-2-phenylbenzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 DEKWFUNEGAIOKS-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- KTNZDANAUJJRBF-UHFFFAOYSA-N 1-bromo-4-(4-ethoxyphenyl)benzene Chemical group C1=CC(OCC)=CC=C1C1=CC=C(Br)C=C1 KTNZDANAUJJRBF-UHFFFAOYSA-N 0.000 description 1
- HKFZHFMWVDJBET-UHFFFAOYSA-N 1-dodecyl-4-(4-ethoxyphenyl)benzene Chemical group C(CCCCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)OCC HKFZHFMWVDJBET-UHFFFAOYSA-N 0.000 description 1
- HAZHJPAZVPNGOJ-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine Chemical compound C1=C(C)C(C)=CC=C1N(C=1C2=CC=C3C(C=4C=CC=CC=4)=CC(=C4C=CC(C2=C43)=C(C=2C=CC=CC=2)C=1)N(C=1C=C(C)C(C)=CC=1)C=1C=C(C)C(C)=CC=1)C1=CC=C(C)C(C)=C1 HAZHJPAZVPNGOJ-UHFFFAOYSA-N 0.000 description 1
- LQZLLITUEMNAAZ-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine Chemical compound C1=C(C)C(C)=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=C(C)C(C)=CC=1)C=1C=C(C)C(C)=CC=1)C1=CC=C(C)C(C)=C1 LQZLLITUEMNAAZ-UHFFFAOYSA-N 0.000 description 1
- UBHOJJRMAHJLMR-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetrakis(3-methylphenyl)pyrene-1,6-diamine Chemical compound CC1=CC=CC(N(C=2C=C(C)C=CC=2)C=2C3=CC=C4C=CC(=C5C=CC(C3=C54)=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 UBHOJJRMAHJLMR-UHFFFAOYSA-N 0.000 description 1
- AXQGZVANICBQBW-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetrakis(4-propan-2-ylphenyl)pyrene-1,6-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC(=CC=1)C(C)C)C=1C=CC(=CC=1)C(C)C)C1=CC=C(C(C)C)C=C1 AXQGZVANICBQBW-UHFFFAOYSA-N 0.000 description 1
- WTEJYGDMCOWSLV-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetraphenylpyrene-1,6-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 WTEJYGDMCOWSLV-UHFFFAOYSA-N 0.000 description 1
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 1
- BUENDBLPCACIGQ-UHFFFAOYSA-N 1-n,6-n-bis(4-ethylphenyl)-1-n,6-n-diphenylpyrene-1,6-diamine Chemical compound C1=CC(CC)=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC(CC)=CC=1)C1=CC=CC=C1 BUENDBLPCACIGQ-UHFFFAOYSA-N 0.000 description 1
- FWKFTAWTOFEJOW-UHFFFAOYSA-N 1-n,6-n-bis(4-methylphenyl)-1-n,6-n-diphenylpyrene-1,6-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC(C)=CC=1)C1=CC=CC=C1 FWKFTAWTOFEJOW-UHFFFAOYSA-N 0.000 description 1
- MNISZASKCGSTTD-UHFFFAOYSA-N 1-n,6-n-bis(4-tert-butylphenyl)-1-n,6-n-diphenylpyrene-1,6-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C(C)(C)C)C1=CC=CC=C1 MNISZASKCGSTTD-UHFFFAOYSA-N 0.000 description 1
- IKHFIMAZKKDZEF-UHFFFAOYSA-N 1-phenyl-2-[4-(10-phenylanthracen-9-yl)phenyl]benzimidazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)C=C1 IKHFIMAZKKDZEF-UHFFFAOYSA-N 0.000 description 1
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- KXVMTFADKIQXJR-UHFFFAOYSA-N 10-N-benzo[a]anthracen-1-ylanthracene-9,10-diamine Chemical compound C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)NC=1C2=CC=CC=C2C(=C2C=CC=CC12)N KXVMTFADKIQXJR-UHFFFAOYSA-N 0.000 description 1
- WQWKHNYXKZPARA-UHFFFAOYSA-N 10-[4-(4-methyl-n-(4-methylphenyl)anilino)naphthalen-1-yl]-n,n-bis(4-methylphenyl)anthracen-9-amine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC=CC=C2C(C=2C3=CC=CC=C3C(N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=C3C=CC=CC3=2)=CC=1)C1=CC=C(C)C=C1 WQWKHNYXKZPARA-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
- MVWPVABZQQJTPL-UHFFFAOYSA-N 2,3-diphenylcyclohexa-2,5-diene-1,4-dione Chemical class O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MVWPVABZQQJTPL-UHFFFAOYSA-N 0.000 description 1
- UXFZNPGAWHMSRK-UHFFFAOYSA-N 2,4-dimethylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC(C)=C21 UXFZNPGAWHMSRK-UHFFFAOYSA-N 0.000 description 1
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 1
- MGKWLYZIHCEOMN-UHFFFAOYSA-N 2,6-dicyclohexyl-9-n,10-n-bis(4-methylphenyl)-9-n,10-n-bis(4-propan-2-ylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC(=CC=C2C(N(C=2C=CC(C)=CC=2)C=2C=CC(=CC=2)C(C)C)=C2C=C(C=CC2=1)C1CCCCC1)C1CCCCC1)C1=CC=C(C)C=C1 MGKWLYZIHCEOMN-UHFFFAOYSA-N 0.000 description 1
- NXXYKOUNUYWIHA-UHFFFAOYSA-M 2,6-dimethylphenolate Chemical compound CC1=CC=CC(C)=C1[O-] NXXYKOUNUYWIHA-UHFFFAOYSA-M 0.000 description 1
- IGOGPMGAOBXQOP-UHFFFAOYSA-N 2,6-ditert-butyl-9-n,10-n-diphenyl-9-n,10-n-bis(4-propan-2-ylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC(=CC=C2C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C(C)C)=C2C=C(C=CC2=1)C(C)(C)C)C(C)(C)C)C1=CC=CC=C1 IGOGPMGAOBXQOP-UHFFFAOYSA-N 0.000 description 1
- HQQDLDVQOHARFC-UHFFFAOYSA-N 2,6-ditert-butyl-9-n,9-n,10-n,10-n-tetrakis(4-methylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC(=CC=C2C(N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C2C=C(C=CC2=1)C(C)(C)C)C(C)(C)C)C1=CC=C(C)C=C1 HQQDLDVQOHARFC-UHFFFAOYSA-N 0.000 description 1
- FMDQYLLFVYISCK-UHFFFAOYSA-N 2,7-bis(4-methoxyphenyl)-9,10-dihydrophenanthrene Chemical compound O(C)C1=CC=C(C2=CC=C3C4=CC=C(C5=CC=C(OC)C=C5)C=C4CCC3=C2)C=C1 FMDQYLLFVYISCK-UHFFFAOYSA-N 0.000 description 1
- LONBOJIXBFUBKQ-UHFFFAOYSA-N 2,7-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC(Br)=CC=C3C2=C1 LONBOJIXBFUBKQ-UHFFFAOYSA-N 0.000 description 1
- GBHMUSBVGVHVLQ-UHFFFAOYSA-N 2-(2'-benzo[h]quinolin-2-yl-9,9'-spirobi[fluorene]-2-yl)benzo[h]quinoline Chemical compound C1=CC=C2C3=NC(C4=CC=C5C=6C(C7(C8=CC(=CC=C8C8=CC=CC=C87)C=7N=C8C9=CC=CC=C9C=CC8=CC=7)C5=C4)=CC=CC=6)=CC=C3C=CC2=C1 GBHMUSBVGVHVLQ-UHFFFAOYSA-N 0.000 description 1
- TWZYORZPYCRVAX-UHFFFAOYSA-N 2-(2h-thiopyran-1-ylidene)propanedinitrile Chemical class N#CC(C#N)=S1CC=CC=C1 TWZYORZPYCRVAX-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- JHRBUQYIRGQOJR-UHFFFAOYSA-N 2-(4-anthracen-9-ylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C3=CC=CC=C3C=C3C=CC=CC3=2)C=C1 JHRBUQYIRGQOJR-UHFFFAOYSA-N 0.000 description 1
- MTQADTZTLQGIRT-UHFFFAOYSA-N 2-(4-dinaphthalen-1-ylphosphorylphenyl)-1,8-naphthyridine Chemical compound C1=CC=C2C(P(C=3C=CC(=CC=3)C=3N=C4N=CC=CC4=CC=3)(C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 MTQADTZTLQGIRT-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- LVXKJHDSZNWVEE-UHFFFAOYSA-N 2-[10-(1,10-phenanthrolin-2-yl)anthracen-9-yl]-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(C4=C5C=CC=CC5=C(C=5N=C6C7=NC=CC=C7C=CC6=CC=5)C5=CC=CC=C54)=CC=C3C=CC2=C1 LVXKJHDSZNWVEE-UHFFFAOYSA-N 0.000 description 1
- CBWNFXBCAUNTDZ-UHFFFAOYSA-N 2-[10-(4-methoxyphenyl)anthracen-9-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound COC1=CC=C(C=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)B1OC(C(O1)(C)C)(C)C CBWNFXBCAUNTDZ-UHFFFAOYSA-N 0.000 description 1
- QWKWMRMSNXMFOE-UHFFFAOYSA-N 2-[2,3-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 QWKWMRMSNXMFOE-UHFFFAOYSA-N 0.000 description 1
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 1
- HFBUZPXNXFVACY-UHFFFAOYSA-N 2-[3-(10-naphthalen-2-ylanthracen-9-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=CC(C=2C3=CC=CC=C3C(C=3C=C4C=CC=CC4=CC=3)=C3C=CC=CC3=2)=C1 HFBUZPXNXFVACY-UHFFFAOYSA-N 0.000 description 1
- DADLFHIINDDPDI-UHFFFAOYSA-N 2-[4-(4-dodecylphenyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound C(CCCCCCCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C DADLFHIINDDPDI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical class C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- AYFJBMBVXWNYLT-UHFFFAOYSA-N 2-bromo-6-methoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OC)=CC=C21 AYFJBMBVXWNYLT-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- AIZMFBKBVGEWMA-UHFFFAOYSA-N 2-dodecyl-6-methoxynaphthalene Chemical compound C1=C(OC)C=CC2=CC(CCCCCCCCCCCC)=CC=C21 AIZMFBKBVGEWMA-UHFFFAOYSA-N 0.000 description 1
- PSIBOPHNSUPJBE-UHFFFAOYSA-N 2-fluoro-6-(9-fluoro-1,10-phenanthrolin-5-yl)-1,10-phenanthroline Chemical group Fc1ccc2cc(-c3cc4ccc(F)nc4c4ncccc34)c3cccnc3c2n1 PSIBOPHNSUPJBE-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- GYUPAYHPAZQUMB-UHFFFAOYSA-N 2-phenyl-9-[3-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=2C3=NC(=CC=2)C=2C=C(C=CC=2)C=2N=C4C5=NC(=CC=C5C=CC4=CC=2)C=2C=CC=CC=2)C3=N1 GYUPAYHPAZQUMB-UHFFFAOYSA-N 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-M 2-phenylphenolate Chemical compound [O-]C1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-M 0.000 description 1
- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical class N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OVBXOMNANIKXCY-UHFFFAOYSA-N 3,10-bis(2,4,6-trimethylphenyl)perylene Chemical group CC1=CC(C)=CC(C)=C1C1=CC=C2C3=C1C=CC=C3C(C=CC=C13)=C1C2=CC=C3C1=C(C)C=C(C)C=C1C OVBXOMNANIKXCY-UHFFFAOYSA-N 0.000 description 1
- ONPGJYGFTLAKCZ-UHFFFAOYSA-N 3,10-bis(2,6-dimethylphenyl)perylene Chemical group CC1=CC=CC(C)=C1C1=CC=C2C3=C1C=CC=C3C(C=CC=C13)=C1C2=CC=C3C1=C(C)C=CC=C1C ONPGJYGFTLAKCZ-UHFFFAOYSA-N 0.000 description 1
- XJOZODMHGRYTRA-UHFFFAOYSA-N 3,10-diphenylperylene Chemical group C1=CC=CC=C1C1=CC=C2C3=C1C=CC=C3C(C=CC=C13)=C1C2=CC=C3C1=CC=CC=C1 XJOZODMHGRYTRA-UHFFFAOYSA-N 0.000 description 1
- HEEPXBSZBHTXLG-UHFFFAOYSA-N 3,4,9,10-tetraphenylperylene Chemical group C1=CC=CC=C1C1=CC=C2C3=C1C(C=1C=CC=CC=1)=CC=C3C(C=CC(=C13)C=4C=CC=CC=4)=C1C2=CC=C3C1=CC=CC=C1 HEEPXBSZBHTXLG-UHFFFAOYSA-N 0.000 description 1
- LINFGHPILLNINI-UHFFFAOYSA-N 3,4-diphenylperylene Chemical group C1=CC=CC=C1C1=CC=C2C3=C1C(C=1C=CC=CC=1)=CC=C3C1=C3C2=CC=CC3=CC=C1 LINFGHPILLNINI-UHFFFAOYSA-N 0.000 description 1
- JNGDCMHTNXRQQD-UHFFFAOYSA-N 3,6-dioxocyclohexa-1,4-diene-1,2,4,5-tetracarbonitrile Chemical compound O=C1C(C#N)=C(C#N)C(=O)C(C#N)=C1C#N JNGDCMHTNXRQQD-UHFFFAOYSA-N 0.000 description 1
- KMZRPGPWSFZJLB-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)chromen-2-one Chemical class C1=CC=C2SC(C3=CC=4C=CC=CC=4OC3=O)=NC2=C1 KMZRPGPWSFZJLB-UHFFFAOYSA-N 0.000 description 1
- ARRJAONCYUAPJR-UHFFFAOYSA-N 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN=C(C=CC=C2)C2=C1 ARRJAONCYUAPJR-UHFFFAOYSA-N 0.000 description 1
- TZHRDJMWCHOOCP-UHFFFAOYSA-N 3-dodecylisoquinoline Chemical compound C1=CC=C2C=NC(CCCCCCCCCCCC)=CC2=C1 TZHRDJMWCHOOCP-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 1
- KBNMXGQJNPGBML-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[4-[10-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]anthracen-9-yl]phenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C3=CC=CC=C3C(C=3C=CC(=CC=3)B3OC(C)(C)C(C)(C)O3)=C3C=CC=CC3=2)C=C1 KBNMXGQJNPGBML-UHFFFAOYSA-N 0.000 description 1
- PQQHEWUCMWFIJP-UHFFFAOYSA-N 4,5-dimethyl-9,10-dihydrophenanthrene Chemical compound C1CC2=CC=CC(C)=C2C2=C1C=CC=C2C PQQHEWUCMWFIJP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 1
- ARUBXNBYMCVENE-UHFFFAOYSA-N 4-(4-bromophenyl)phenol Chemical compound C1=CC(O)=CC=C1C1=CC=C(Br)C=C1 ARUBXNBYMCVENE-UHFFFAOYSA-N 0.000 description 1
- GBBJDAGBKWPVKH-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-undecylquinoline Chemical compound C(CCCCCCCCCC)C1=NC2=CC=CC=C2C(=C1)C1=CC=C(C=C1)Cl GBBJDAGBKWPVKH-UHFFFAOYSA-N 0.000 description 1
- WAFDROXRIDLRSU-UHFFFAOYSA-N 4-(4-dodecylphenyl)phenol Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1C1=CC=C(O)C=C1 WAFDROXRIDLRSU-UHFFFAOYSA-N 0.000 description 1
- OPKQAOBTBQLNCB-UHFFFAOYSA-N 4-[10-(4-hydroxyphenyl)anthracen-9-yl]phenol Chemical compound C1=CC(O)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(O)C=C1 OPKQAOBTBQLNCB-UHFFFAOYSA-N 0.000 description 1
- IRLQXBNYTPJBFI-UHFFFAOYSA-N 4-[10-[4-(2-undecylquinolin-4-yl)phenyl]anthracen-9-yl]phenol Chemical compound CCCCCCCCCCCC1=NC2=CC=CC=C2C(=C1)C3=CC=C(C=C3)C4=C5C=CC=CC5=C(C6=CC=CC=C64)C7=CC=C(C=C7)O IRLQXBNYTPJBFI-UHFFFAOYSA-N 0.000 description 1
- YVZYZHWUJOGQFF-UHFFFAOYSA-N 4-[7-(4-hydroxyphenyl)-9,9-dimethylfluoren-2-yl]phenol Chemical compound C1=C2C(C)(C)C3=CC(C=4C=CC(O)=CC=4)=CC=C3C2=CC=C1C1=CC=C(O)C=C1 YVZYZHWUJOGQFF-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- HQAIROMRVBVWSK-UHFFFAOYSA-N 4-chloro-2-methylquinoline Chemical compound C1=CC=CC2=NC(C)=CC(Cl)=C21 HQAIROMRVBVWSK-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- AOQKGYRILLEVJV-UHFFFAOYSA-N 4-naphthalen-1-yl-3,5-diphenyl-1,2,4-triazole Chemical compound C1=CC=CC=C1C(N1C=2C3=CC=CC=C3C=CC=2)=NN=C1C1=CC=CC=C1 AOQKGYRILLEVJV-UHFFFAOYSA-N 0.000 description 1
- FNERQQDCQZWYOC-UHFFFAOYSA-N 5-(10-naphthalen-2-ylanthracen-9-yl)-1,2-diphenylbenzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC(C=3C4=CC=CC=C4C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=3)=CC=C2N1C1=CC=CC=C1 FNERQQDCQZWYOC-UHFFFAOYSA-N 0.000 description 1
- YYLPUCXGNWKUDJ-UHFFFAOYSA-N 5-(9,10-dinaphthalen-2-ylanthracen-2-yl)-1,2-diphenylbenzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC(C=3C=C4C(C=5C=C6C=CC=CC6=CC=5)=C5C=CC=CC5=C(C=5C=C6C=CC=CC6=CC=5)C4=CC=3)=CC=C2N1C1=CC=CC=C1 YYLPUCXGNWKUDJ-UHFFFAOYSA-N 0.000 description 1
- DEYHZYIPSXJFEO-UHFFFAOYSA-N 5-[3,5-bis(1,10-phenanthrolin-5-yl)phenyl]-1,10-phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C=C1C1=CC(C=2C3=CC=CN=C3C3=NC=CC=C3C=2)=CC(C=2C3=CC=CN=C3C3=NC=CC=C3C=2)=C1 DEYHZYIPSXJFEO-UHFFFAOYSA-N 0.000 description 1
- CKOCSOGJXPVDMI-UHFFFAOYSA-N 5-[6-(1,10-phenanthrolin-5-yl)pyridin-2-yl]-1,10-phenanthroline Chemical compound C1=CC=C2C(C=3C=CC=C(N=3)C=3C4=CC=CN=C4C4=NC=CC=C4C=3)=CC3=CC=CN=C3C2=N1 CKOCSOGJXPVDMI-UHFFFAOYSA-N 0.000 description 1
- AUTCCMQRZFBGDK-UHFFFAOYSA-N 6-[4-[10-[4-(6-dodecylnaphthalen-2-yl)phenyl]anthracen-9-yl]phenyl]quinoline Chemical compound CCCCCCCCCCCCC1=CC2=C(C=C1)C=C(C=C2)C3=CC=C(C=C3)C4=C5C=CC=CC5=C(C6=CC=CC=C64)C7=CC=C(C=C7)C8=CC9=C(C=C8)N=CC=C9 AUTCCMQRZFBGDK-UHFFFAOYSA-N 0.000 description 1
- JJDDZRAITXMDLD-UHFFFAOYSA-N 6-bromo-2-[4-[10-[4-(6-bromoquinolin-2-yl)phenyl]anthracen-9-yl]phenyl]quinoline Chemical compound BrC=1C=C2C=CC(=NC2=CC=1)C1=CC=C(C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC=C(C=C1)C1=NC2=CC=C(C=C2C=C1)Br JJDDZRAITXMDLD-UHFFFAOYSA-N 0.000 description 1
- YXRDWUJAJLDABJ-UHFFFAOYSA-N 6-bromo-2-chloroquinoline Chemical compound C1=C(Br)C=CC2=NC(Cl)=CC=C21 YXRDWUJAJLDABJ-UHFFFAOYSA-N 0.000 description 1
- IFIHYLCUKYCKRH-UHFFFAOYSA-N 6-bromoquinoline Chemical compound N1=CC=CC2=CC(Br)=CC=C21 IFIHYLCUKYCKRH-UHFFFAOYSA-N 0.000 description 1
- WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 description 1
- IXTMYFVUSBTFMO-UHFFFAOYSA-N 6-chloro-3-heptylisoquinoline Chemical compound CCCCCCCC1=NC=C2C=CC(=CC2=C1)Cl IXTMYFVUSBTFMO-UHFFFAOYSA-N 0.000 description 1
- JFKUZDVNNMPPNN-UHFFFAOYSA-N 6-dodecylnaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(CCCCCCCCCCCC)=CC=C21 JFKUZDVNNMPPNN-UHFFFAOYSA-N 0.000 description 1
- JBSGIWZNUUUNBB-UHFFFAOYSA-N 6-n,12-n-bis(4-ethylphenyl)-6-n,12-n-diphenylchrysene-6,12-diamine Chemical compound C1=CC(CC)=CC=C1N(C=1C2=CC=CC=C2C2=CC(=C3C=CC=CC3=C2C=1)N(C=1C=CC=CC=1)C=1C=CC(CC)=CC=1)C1=CC=CC=C1 JBSGIWZNUUUNBB-UHFFFAOYSA-N 0.000 description 1
- IPJHGORFBMOUGA-UHFFFAOYSA-N 6-n,12-n-bis(4-methylphenyl)-6-n,12-n-bis(4-propan-2-ylphenyl)chrysene-6,12-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC=CC=C2C2=CC(=C3C=CC=CC3=C2C=1)N(C=1C=CC(C)=CC=1)C=1C=CC(=CC=1)C(C)C)C1=CC=C(C)C=C1 IPJHGORFBMOUGA-UHFFFAOYSA-N 0.000 description 1
- ULXXGNOISOWXCJ-UHFFFAOYSA-N 6-n,12-n-diphenyl-6-n,12-n-bis(4-propan-2-ylphenyl)chrysene-6,12-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC=CC=C2C2=CC(=C3C=CC=CC3=C2C=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C(C)C)C1=CC=CC=C1 ULXXGNOISOWXCJ-UHFFFAOYSA-N 0.000 description 1
- MRTINRUFHXEJHO-UHFFFAOYSA-N 6-n,6-n,12-n,12-n-tetrakis(3-methylphenyl)chrysene-6,12-diamine Chemical compound CC1=CC=CC(N(C=2C=C(C)C=CC=2)C=2C3=CC=CC=C3C3=CC(=C4C=CC=CC4=C3C=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 MRTINRUFHXEJHO-UHFFFAOYSA-N 0.000 description 1
- ADPTUNPKYGZJMJ-UHFFFAOYSA-N 6-n,6-n,12-n,12-n-tetrakis(4-propan-2-ylphenyl)chrysene-6,12-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC=CC=C2C2=CC(=C3C=CC=CC3=C2C=1)N(C=1C=CC(=CC=1)C(C)C)C=1C=CC(=CC=1)C(C)C)C1=CC=C(C(C)C)C=C1 ADPTUNPKYGZJMJ-UHFFFAOYSA-N 0.000 description 1
- FYSCMYSZCIZQIY-UHFFFAOYSA-N 6-n,6-n,12-n,12-n-tetranaphthalen-2-ylchrysene-6,12-diamine Chemical compound C1=CC=CC2=CC(N(C=3C=C4C=CC=CC4=CC=3)C3=C4C=CC=CC4=C4C=C(C5=CC=CC=C5C4=C3)N(C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 FYSCMYSZCIZQIY-UHFFFAOYSA-N 0.000 description 1
- QZMRZMUXFCMRJU-UHFFFAOYSA-N 6-n,6-n,12-n,12-n-tetraphenylchrysene-6,12-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C2=CC(=C3C=CC=CC3=C2C=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 QZMRZMUXFCMRJU-UHFFFAOYSA-N 0.000 description 1
- XWQHSZLJSZGULC-UHFFFAOYSA-N 6-octyl-2-[4-[10-[4-(6-octylquinolin-2-yl)phenyl]anthracen-9-yl]phenyl]quinoline Chemical compound C(CCCCCCC)C=1C=C2C=CC(=NC2=CC=1)C1=CC=C(C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC=C(C=C1)C1=NC2=CC=C(C=C2C=C1)CCCCCCCC XWQHSZLJSZGULC-UHFFFAOYSA-N 0.000 description 1
- ZVNJIMAISJIRBB-UHFFFAOYSA-N 7-(4-anthracen-9-ylphenyl)-3-dodecylisoquinoline Chemical compound CCCCCCCCCCCCC1=NC=C2C=C(C=CC2=C1)C3=CC=C(C=C3)C4=C5C=CC=CC5=CC6=CC=CC=C64 ZVNJIMAISJIRBB-UHFFFAOYSA-N 0.000 description 1
- YILORWIUGAYTHR-UHFFFAOYSA-N 7-[4-(10-bromoanthracen-9-yl)phenyl]-3-dodecylisoquinoline Chemical compound BrC1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=C(C=C1)C1=CC=C2C=C(N=CC2=C1)CCCCCCCCCCCC YILORWIUGAYTHR-UHFFFAOYSA-N 0.000 description 1
- JZRRWOJNMVCCKU-UHFFFAOYSA-N 7-chloro-3-dodecylisoquinoline Chemical compound CCCCCCCCCCCCC1=NC=C2C=C(C=CC2=C1)Cl JZRRWOJNMVCCKU-UHFFFAOYSA-N 0.000 description 1
- RHNRCJIZNFJJPU-UHFFFAOYSA-N 7-chloro-3-hexylisoquinoline Chemical compound CCCCCCC1=NC=C2C=C(C=CC2=C1)Cl RHNRCJIZNFJJPU-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical class C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- SZNIOXYCNCSUBC-UHFFFAOYSA-N 7-piperidin-1-ylchromen-2-one Chemical class C1=C2OC(=O)C=CC2=CC=C1N1CCCCC1 SZNIOXYCNCSUBC-UHFFFAOYSA-N 0.000 description 1
- YYBCFFUVEXWJIU-UHFFFAOYSA-N 8-N-benzo[a]anthracen-1-ylpyrene-1,8-diamine Chemical compound C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)NC1=CC=C2C=CC3=CC=C(C4=CC=C1C2=C34)N YYBCFFUVEXWJIU-UHFFFAOYSA-N 0.000 description 1
- KTYCXBAOXVVIMM-UHFFFAOYSA-N 9,10-bis(4-methoxyphenyl)anthracene Chemical compound C1=CC(OC)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(OC)C=C1 KTYCXBAOXVVIMM-UHFFFAOYSA-N 0.000 description 1
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 1
- GJWBRYKOJMOBHH-UHFFFAOYSA-N 9,9-dimethyl-n-[4-(9-phenylcarbazol-3-yl)phenyl]-n-(4-phenylphenyl)fluoren-2-amine Chemical compound C1=C2C(C)(C)C3=CC=CC=C3C2=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 GJWBRYKOJMOBHH-UHFFFAOYSA-N 0.000 description 1
- LSMKKSHCLCSFQZ-UHFFFAOYSA-N 9-[4-(trifluoromethyl)phenyl]anthracene Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 LSMKKSHCLCSFQZ-UHFFFAOYSA-N 0.000 description 1
- DXPJZZIPJNCWLH-UHFFFAOYSA-N 9-bromo-10-(4-methoxyphenyl)anthracene Chemical compound C1=CC(OC)=CC=C1C1=C(C=CC=C2)C2=C(Br)C2=CC=CC=C12 DXPJZZIPJNCWLH-UHFFFAOYSA-N 0.000 description 1
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 1
- LMTXHBDTVAIIQY-UHFFFAOYSA-N 9-n,10-n-bis(3-methylphenyl)-9-n,10-n-diphenylanthracene-9,10-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C(N(C=3C=CC=CC=3)C=3C=C(C)C=CC=3)=C3C=CC=CC3=2)=C1 LMTXHBDTVAIIQY-UHFFFAOYSA-N 0.000 description 1
- NEKCGUVVHQZBGZ-UHFFFAOYSA-N 9-n,10-n-bis(4-ethylphenyl)-9-n,10-n-diphenylanthracene-9,10-diamine Chemical compound C1=CC(CC)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC=CC=2)C=2C=CC(CC)=CC=2)=C2C=CC=CC2=1)C1=CC=CC=C1 NEKCGUVVHQZBGZ-UHFFFAOYSA-N 0.000 description 1
- XDGZJXIRKASDIR-UHFFFAOYSA-N 9-n,10-n-bis(4-methylphenyl)-9-n,10-n-bis(4-propan-2-ylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC(C)=CC=2)C=2C=CC(=CC=2)C(C)C)=C2C=CC=CC2=1)C1=CC=C(C)C=C1 XDGZJXIRKASDIR-UHFFFAOYSA-N 0.000 description 1
- HTJPPQKJCPTAED-UHFFFAOYSA-N 9-n,10-n-bis(4-methylphenyl)-9-n,10-n-diphenylanthracene-9,10-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC=CC=2)C=2C=CC(C)=CC=2)=C2C=CC=CC2=1)C1=CC=CC=C1 HTJPPQKJCPTAED-UHFFFAOYSA-N 0.000 description 1
- RZHKAHGXIVQQME-UHFFFAOYSA-N 9-n,10-n-bis(4-tert-butylphenyl)-2,6-dicyclohexyl-9-n,10-n-bis(4-propan-2-ylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC(=CC=C2C(N(C=2C=CC(=CC=2)C(C)C)C=2C=CC(=CC=2)C(C)(C)C)=C2C=C(C=CC2=1)C1CCCCC1)C1CCCCC1)C1=CC=C(C(C)(C)C)C=C1 RZHKAHGXIVQQME-UHFFFAOYSA-N 0.000 description 1
- CZBKCKYVTCQGGV-UHFFFAOYSA-N 9-n,10-n-bis(4-tert-butylphenyl)-9-n,10-n-diphenylanthracene-9,10-diamine Chemical compound C1=CC(C(C)(C)C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C(C)(C)C)=C2C=CC=CC2=1)C1=CC=CC=C1 CZBKCKYVTCQGGV-UHFFFAOYSA-N 0.000 description 1
- VIISMVUXLKQDHC-UHFFFAOYSA-N 9-n,10-n-diphenyl-9-n,10-n-bis(4-propan-2-ylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C(C)C)=C2C=CC=CC2=1)C1=CC=CC=C1 VIISMVUXLKQDHC-UHFFFAOYSA-N 0.000 description 1
- ANWJEKBFPXUTHF-UHFFFAOYSA-N 9-n,9-n,10-n,10-n-tetrakis(3-methylphenyl)anthracene-9,10-diamine Chemical compound CC1=CC=CC(N(C=2C=C(C)C=CC=2)C=2C3=CC=CC=C3C(N(C=3C=C(C)C=CC=3)C=3C=C(C)C=CC=3)=C3C=CC=CC3=2)=C1 ANWJEKBFPXUTHF-UHFFFAOYSA-N 0.000 description 1
- FWXNJWAXBVMBGL-UHFFFAOYSA-N 9-n,9-n,10-n,10-n-tetrakis(4-methylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C2C=CC=CC2=1)C1=CC=C(C)C=C1 FWXNJWAXBVMBGL-UHFFFAOYSA-N 0.000 description 1
- PLONQNQFKOWLGH-UHFFFAOYSA-N 9-n,9-n,10-n,10-n-tetrakis(4-propan-2-ylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C(C)C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC(=CC=2)C(C)C)C=2C=CC(=CC=2)C(C)C)=C2C=CC=CC2=1)C1=CC=C(C(C)C)C=C1 PLONQNQFKOWLGH-UHFFFAOYSA-N 0.000 description 1
- RRFSDXVQFGASBQ-UHFFFAOYSA-N 9-phenyl-10-(4-phenylnaphthalen-1-yl)anthracene Chemical compound c1ccc(cc1)-c1ccc(-c2c3ccccc3c(-c3ccccc3)c3ccccc23)c2ccccc12 RRFSDXVQFGASBQ-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical group C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- ALJVGGQTKYIEOV-UHFFFAOYSA-N C(#N)N1C=2C=3N=C(C=NC3C3=NC(=C(N=C3C2N=C(C1C#N)C#N)C#N)C#N)C#N Chemical compound C(#N)N1C=2C=3N=C(C=NC3C3=NC(=C(N=C3C2N=C(C1C#N)C#N)C#N)C#N)C#N ALJVGGQTKYIEOV-UHFFFAOYSA-N 0.000 description 1
- GZWHZAOUGAAPLJ-UHFFFAOYSA-N C(CCCCCCCCCCC)C1=CC2=CC=C(C=C2C=C1)C1=CC=C(C=C1)OC Chemical compound C(CCCCCCCCCCC)C1=CC2=CC=C(C=C2C=C1)C1=CC=C(C=C1)OC GZWHZAOUGAAPLJ-UHFFFAOYSA-N 0.000 description 1
- DLQUVERMPCHLML-UHFFFAOYSA-N C(CCCCCCCCCCC)C=1C=C2C=CC(=CC2=CC=1)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C Chemical compound C(CCCCCCCCCCC)C=1C=C2C=CC(=CC2=CC=1)C1=CC=C(C=C1)B1OC(C(O1)(C)C)(C)C DLQUVERMPCHLML-UHFFFAOYSA-N 0.000 description 1
- CBQJGOGIHKZPDK-UHFFFAOYSA-N C(CCCCCCCCCCC)C=1C=C2C=CC(=CC2=CC=1)C1=CC=C(C=C1)O Chemical compound C(CCCCCCCCCCC)C=1C=C2C=CC(=CC2=CC=1)C1=CC=C(C=C1)O CBQJGOGIHKZPDK-UHFFFAOYSA-N 0.000 description 1
- XOSDLJAQCAVZBE-UHFFFAOYSA-N C1(=CC=C(C=C1)C1=C(C=2C=CC3=CC=C(C=4C=CC(=C1)C2C43)N)N)C Chemical compound C1(=CC=C(C=C1)C1=C(C=2C=CC3=CC=C(C=4C=CC(=C1)C2C43)N)N)C XOSDLJAQCAVZBE-UHFFFAOYSA-N 0.000 description 1
- SQDWRQRZWKAFMF-UHFFFAOYSA-N C1(=CC=CC=C1)N(C1=CC=C(C2=CC=CC=C12)C1=C(C=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical group C1(=CC=CC=C1)N(C1=CC=C(C2=CC=CC=C12)C1=C(C=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 SQDWRQRZWKAFMF-UHFFFAOYSA-N 0.000 description 1
- PRINGLWXBBJDAZ-UHFFFAOYSA-N C1(=CC=CC=C1)N(C=1C=C2C=CC(=CC2=CC1)C=1C2=CC=CC=C2C=C2C=CC=CC12)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)N(C=1C=C2C=CC(=CC2=CC1)C=1C2=CC=CC=C2C=C2C=CC=CC12)C1=CC=CC=C1 PRINGLWXBBJDAZ-UHFFFAOYSA-N 0.000 description 1
- WNNZNHXEESAWDO-UHFFFAOYSA-N CCCCCCC(N=CC1=C2)=CC1=CC=C2C(C=C1)=CC=C1C(C=CC1=C2CCC3=CC=CC=C13)=C2C(C=C1)=CC=C1C1=CC=C(C=C(CCCCCC)N=C2)C2=C1 Chemical compound CCCCCCC(N=CC1=C2)=CC1=CC=C2C(C=C1)=CC=C1C(C=CC1=C2CCC3=CC=CC=C13)=C2C(C=C1)=CC=C1C1=CC=C(C=C(CCCCCC)N=C2)C2=C1 WNNZNHXEESAWDO-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JWXYEXKKOMBZBH-UHFFFAOYSA-N Cc(cc1)cc(cc2)c1cc2OC Chemical compound Cc(cc1)cc(cc2)c1cc2OC JWXYEXKKOMBZBH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- XDKAALBPVUYIGO-UHFFFAOYSA-N FC(S(=O)(=O)OC1=CC=C(C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F)(F)F Chemical compound FC(S(=O)(=O)OC1=CC=C(C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC=C(C=C1)OS(=O)(=O)C(F)(F)F)(F)F XDKAALBPVUYIGO-UHFFFAOYSA-N 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 0.000 description 1
- QNUDGIMHDHMXKY-UHFFFAOYSA-N Oc(cc1)ccc1-c(cc1CC2)ccc1-c(cc1)c2cc1-c(cc1)ccc1O Chemical compound Oc(cc1)ccc1-c(cc1CC2)ccc1-c(cc1)c2cc1-c(cc1)ccc1O QNUDGIMHDHMXKY-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Chemical class C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- MYKTYGDXTWLXAG-UHFFFAOYSA-N [10-(4-carbazol-9-ylphenyl)anthracen-9-yl]-bis(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1B(C=1C2=CC=CC=C2C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)=C2C=CC=CC2=1)C1=C(C)C=C(C)C=C1C MYKTYGDXTWLXAG-UHFFFAOYSA-N 0.000 description 1
- HEDOCDOUMOZTKC-UHFFFAOYSA-N [10-(4-phenylphenyl)anthracen-9-yl]-bis(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1B(C=1C2=CC=CC=C2C(C=2C=CC(=CC=2)C=2C=CC=CC=2)=C2C=CC=CC2=1)C1=C(C)C=C(C)C=C1C HEDOCDOUMOZTKC-UHFFFAOYSA-N 0.000 description 1
- GYGSBQRCLZEEPH-UHFFFAOYSA-N [4-(4-carbazol-9-ylphenyl)naphthalen-1-yl]-bis(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1B(C=1C2=CC=CC=C2C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=1)C1=C(C)C=C(C)C=C1C GYGSBQRCLZEEPH-UHFFFAOYSA-N 0.000 description 1
- PYQBNSSKFSDQOT-UHFFFAOYSA-K [Al+3].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-] Chemical compound [Al+3].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-].C(C)(C)(C)C=1C=C(C=C(C1)C(C)(C)C)[O-] PYQBNSSKFSDQOT-UHFFFAOYSA-K 0.000 description 1
- HEDVYVLDUQAGPT-UHFFFAOYSA-K [Al+3].C1(=CC=CC=C1)C1=C(C(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)[O-].C1(=CC=CC=C1)C1=C(C(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)[O-].C1(=CC=CC=C1)C1=C(C(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)[O-] Chemical compound [Al+3].C1(=CC=CC=C1)C1=C(C(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)[O-].C1(=CC=CC=C1)C1=C(C(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)[O-].C1(=CC=CC=C1)C1=C(C(=CC(=C1)C1=CC=CC=C1)C1=CC=CC=C1)[O-] HEDVYVLDUQAGPT-UHFFFAOYSA-K 0.000 description 1
- YTTZYYBKYGKPKU-UHFFFAOYSA-K [Al+3].CC1=C(C(=C(C(=C1)C)C)C)[O-].CC1=C(C(=C(C(=C1)C)C)C)[O-].CC1=C(C(=C(C(=C1)C)C)C)[O-] Chemical compound [Al+3].CC1=C(C(=C(C(=C1)C)C)C)[O-].CC1=C(C(=C(C(=C1)C)C)C)[O-].CC1=C(C(=C(C(=C1)C)C)C)[O-] YTTZYYBKYGKPKU-UHFFFAOYSA-K 0.000 description 1
- COEBMFJNDKHWJJ-UHFFFAOYSA-K [Al+3].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-] Chemical compound [Al+3].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-].CC1=C(C(=CC(=C1)C)C)[O-] COEBMFJNDKHWJJ-UHFFFAOYSA-K 0.000 description 1
- XNQHTZNYBVULHJ-UHFFFAOYSA-K [Al+3].CC=1C=C(C=CC1C)[O-].CC=1C=C(C=CC1C)[O-].CC=1C=C(C=CC1C)[O-] Chemical compound [Al+3].CC=1C=C(C=CC1C)[O-].CC=1C=C(C=CC1C)[O-].CC=1C=C(C=CC1C)[O-] XNQHTZNYBVULHJ-UHFFFAOYSA-K 0.000 description 1
- JZXXUZWBECTQIC-UHFFFAOYSA-N [Li].C1=CC=CC2=NC(O)=CC=C21 Chemical compound [Li].C1=CC=CC2=NC(O)=CC=C21 JZXXUZWBECTQIC-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001251 acridines Chemical class 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 1
- OJZUGISYZNONCF-UHFFFAOYSA-K aluminum;2,3-dimethylphenolate Chemical compound [Al+3].CC1=CC=CC([O-])=C1C.CC1=CC=CC([O-])=C1C.CC1=CC=CC([O-])=C1C OJZUGISYZNONCF-UHFFFAOYSA-K 0.000 description 1
- CKRHKYHOTKICCR-UHFFFAOYSA-K aluminum;2,6-diphenylphenolate Chemical compound [Al+3].[O-]C1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1.[O-]C1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1.[O-]C1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 CKRHKYHOTKICCR-UHFFFAOYSA-K 0.000 description 1
- PSYWRPCLOJXWEN-UHFFFAOYSA-K aluminum;2-phenylphenolate Chemical compound [Al+3].[O-]C1=CC=CC=C1C1=CC=CC=C1.[O-]C1=CC=CC=C1C1=CC=CC=C1.[O-]C1=CC=CC=C1C1=CC=CC=C1 PSYWRPCLOJXWEN-UHFFFAOYSA-K 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- VCICMBWXNBMICE-UHFFFAOYSA-N anthracen-9-yl-bis(2,4,6-trimethylphenyl)borane Chemical compound CC1=CC(C)=CC(C)=C1B(C=1C2=CC=CC=C2C=C2C=CC=CC2=1)C1=C(C)C=C(C)C=C1C VCICMBWXNBMICE-UHFFFAOYSA-N 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000007980 azole derivatives Chemical class 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- ZJHMRPBTRSQNPI-UHFFFAOYSA-N benzo[b][1]benzosilole Chemical compound C1=CC=C2[Si]C3=CC=CC=C3C2=C1 ZJHMRPBTRSQNPI-UHFFFAOYSA-N 0.000 description 1
- TUAHORSUHVUKBD-UHFFFAOYSA-N benzo[c]phenanthrene Chemical compound C1=CC=CC2=C3C4=CC=CC=C4C=CC3=CC=C21 TUAHORSUHVUKBD-UHFFFAOYSA-N 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000005885 boration reaction Methods 0.000 description 1
- 125000000707 boryl group Chemical group B* 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N caesium oxide Chemical compound [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 229910001942 caesium oxide Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 1
- 125000003991 chrysen-1-yl group Chemical group [H]C1=C([H])C2=C(C([H])=C1[H])C1=C([H])C([H])=C3C(*)=C([H])C([H])=C([H])C3=C1C([H])=C2[H] 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- JBPCDMSEJVCNGV-UHFFFAOYSA-N coumarin 334 Chemical compound C1CCC2=C(OC(C(C(=O)C)=C3)=O)C3=CC3=C2N1CCC3 JBPCDMSEJVCNGV-UHFFFAOYSA-N 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 description 1
- YEIOLSIOGKBJAR-UHFFFAOYSA-L cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+);nickel(2+);dichloride Chemical compound [Fe+2].Cl[Ni]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YEIOLSIOGKBJAR-UHFFFAOYSA-L 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- JNTHRSHGARDABO-UHFFFAOYSA-N dibenzo[a,l]pyrene Chemical compound C1=CC=CC2=C3C4=CC=CC=C4C=C(C=C4)C3=C3C4=CC=CC3=C21 JNTHRSHGARDABO-UHFFFAOYSA-N 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- ZBQUMMFUJLOTQC-UHFFFAOYSA-L dichloronickel;3-diphenylphosphanylpropyl(diphenyl)phosphane Chemical compound Cl[Ni]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 ZBQUMMFUJLOTQC-UHFFFAOYSA-L 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- NNNFHIWKVLLMKH-UHFFFAOYSA-N ditert-butyl-[1-(2-ditert-butylphosphanylnaphthalen-1-yl)naphthalen-2-yl]phosphane Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3P(C(C)(C)C)C(C)(C)C)=C(P(C(C)(C)C)C(C)(C)C)C=CC2=C1 NNNFHIWKVLLMKH-UHFFFAOYSA-N 0.000 description 1
- MUPGNOONALUUNP-UHFFFAOYSA-N ditert-butyl-[1-(2-methoxynaphthalen-1-yl)naphthalen-2-yl]phosphane Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3OC)=C(P(C(C)(C)C)C(C)(C)C)C=CC2=C1 MUPGNOONALUUNP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003993 fluoranthen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C1=C([H])C([H])=C([H])C3=C([H])C([H])=C(*)C2=C13 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical class O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical class C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 150000002258 gallium Chemical class 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [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 1
- LIIALPBMIOVAHH-UHFFFAOYSA-N herniarin Chemical class C1=CC(=O)OC2=CC(OC)=CC=C21 LIIALPBMIOVAHH-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000005232 imidazopyridines Chemical class 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- LBAIJNRSTQHDMR-UHFFFAOYSA-N magnesium phthalocyanine Chemical compound [Mg].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 LBAIJNRSTQHDMR-UHFFFAOYSA-N 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- IOOQQIVFCFWSIU-UHFFFAOYSA-M magnesium;octane;bromide Chemical compound [Mg+2].[Br-].CCCCCCC[CH2-] IOOQQIVFCFWSIU-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- UVEAFTFQMHUWEY-UHFFFAOYSA-N methane;1,2,4,5-tetrafluoro-3,6-dioxocyclohexane-1,2,4,5-tetracarbonitrile Chemical compound C.C.N#CC1(F)C(=O)C(F)(C#N)C(F)(C#N)C(=O)C1(F)C#N UVEAFTFQMHUWEY-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- XNLCINMGJXZRCL-UHFFFAOYSA-N n,n-bis(4-phenylphenyl)-4-[2-[4-(4-phenyl-n-(4-phenylphenyl)anilino)phenyl]ethenyl]aniline Chemical compound C=1C=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C(C=C1)=CC=C1C1=CC=CC=C1 XNLCINMGJXZRCL-UHFFFAOYSA-N 0.000 description 1
- LKGJCLPKCSMVMU-UHFFFAOYSA-N n,n-diphenyl-10-[4-(n-phenylanilino)naphthalen-1-yl]anthracen-9-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C(C=2C3=CC=CC=C3C(N(C=3C=CC=CC=3)C=3C=CC=CC=3)=C3C=CC=CC3=2)=CC=1)C1=CC=CC=C1 LKGJCLPKCSMVMU-UHFFFAOYSA-N 0.000 description 1
- VMYGJDWWPZOCGV-UHFFFAOYSA-N n,n-diphenyl-4-[10-[4-(n-phenylanilino)phenyl]anthracen-9-yl]aniline Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C2=CC=CC=C2C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C2C=CC=CC2=1)C1=CC=CC=C1 VMYGJDWWPZOCGV-UHFFFAOYSA-N 0.000 description 1
- ZUXHZYJQZZKWHO-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]naphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C2=CC=CC=C2C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 ZUXHZYJQZZKWHO-UHFFFAOYSA-N 0.000 description 1
- BBPWMDBTJRZHJF-UHFFFAOYSA-N n,n-diphenyl-6-[4-(n-phenylanilino)phenyl]naphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=C2C=CC(=CC2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 BBPWMDBTJRZHJF-UHFFFAOYSA-N 0.000 description 1
- FWORJTDMYDOYQR-UHFFFAOYSA-N n,n-diphenyl-6-[4-[4-[4-[6-(n-phenylanilino)naphthalen-2-yl]phenyl]phenyl]phenyl]naphthalen-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=CC(=CC2=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=C2C=CC(=CC2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 FWORJTDMYDOYQR-UHFFFAOYSA-N 0.000 description 1
- NKECJJVYVFYJRK-UHFFFAOYSA-N n,n-diphenyl-6-[4-[4-[6-(n-phenylanilino)naphthalen-2-yl]phenyl]phenyl]naphthalen-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=CC(=CC2=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)C=1C=C2C=CC(=CC2=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 NKECJJVYVFYJRK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- RHQMPGSJRXCZBK-UHFFFAOYSA-N n-[4-[2-[4-(dinaphthalen-2-ylamino)phenyl]ethenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=C4C=CC=CC4=CC=3)C3=CC=C(C=C3)C=CC=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)=CC=C21 RHQMPGSJRXCZBK-UHFFFAOYSA-N 0.000 description 1
- WMBKUKCCQLBJRE-UHFFFAOYSA-N n-[4-[2-[4-(n-naphthalen-2-ylanilino)phenyl]ethenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 WMBKUKCCQLBJRE-UHFFFAOYSA-N 0.000 description 1
- ZFIQKTXFWZQWDV-UHFFFAOYSA-N n-[4-[2-[4-(n-phenanthren-9-ylanilino)phenyl]ethenyl]phenyl]-n-phenylphenanthren-9-amine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C3=CC=CC=C3C=2)C=CC=1C=CC(C=C1)=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1)C1=CC=CC=C1 ZFIQKTXFWZQWDV-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 125000000913 palmityl 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])C([H])([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 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000002958 pentadecyl 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])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 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004225 phenalen-1-yl group Chemical group [H]C1=C([H])C2=C3C(C([H])=C([H])C([H])(*)C3=C([H])C([H])=C2[H])=C1[H] 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- FIZIRKROSLGMPL-UHFFFAOYSA-N phenoxazin-1-one Chemical group C1=CC=C2N=C3C(=O)C=CC=C3OC2=C1 FIZIRKROSLGMPL-UHFFFAOYSA-N 0.000 description 1
- 125000001644 phenoxazinyl group Chemical class C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001732 pyren-2-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C3C([H])=C(*)C([H])=C4C([H])=C([H])C(=C1[H])C2=C34 0.000 description 1
- 125000001486 pyren-4-yl group Chemical group [H]C1=C(C2=C34)C([H])=C([H])C([H])=C2C([*])=C([H])C3=C([H])C([H])=C([H])C4=C1[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- BXEMXLDMNMKWPV-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1 BXEMXLDMNMKWPV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- KATIRQRAVXTBNY-UHFFFAOYSA-N quinolin-4-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=NC2=C1 KATIRQRAVXTBNY-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 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
- 150000003839 salts Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KJVQYDYPDFFJMP-UHFFFAOYSA-N sulfamethylthiazole Chemical compound CC1=CSC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 KJVQYDYPDFFJMP-UHFFFAOYSA-N 0.000 description 1
- 229950005939 sulfamethylthiazole Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 125000005756 tetralinylene group Chemical group 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000011135 tin Substances 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
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000005580 triphenylene group Chemical class 0.000 description 1
- WGWZJNILGYTDHU-UHFFFAOYSA-K tris(3,5-dimethylphenoxy)alumane Chemical compound CC=1C=C([O-])C=C(C1)C.[Al+3].CC=1C=C([O-])C=C(C1)C.CC=1C=C([O-])C=C(C1)C WGWZJNILGYTDHU-UHFFFAOYSA-K 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical class C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Ar1、Ar2およびAr3は、それぞれ独立して、炭素数7〜20の2価の芳香族基またはヘテロ芳香族基であり、Ar2およびAr3は共に芳香族基であるかまたは共にヘテロ芳香族基であり、Ar1、Ar2およびAr3における少なくとも1つの水素は炭素数1〜4のアルキル基で置換されていてもよく、
Ar1、Ar2、およびAr3の炭素数の合計は24〜38であり、
上記式(1)中に図示した2つのp−フェニレン基における少なくとも1つの水素はメチル基で置換されていてもよく、
Ar1と結合する2つのp−フェニレン基の間の結合軸が成す角度は120〜240度であり、
R1およびR2は、それぞれ独立して、水素または炭素数1〜20のアルキル基であり、当該アルキル基における任意のメチレン基(−CH2−)は−O−または−S−で置き換わっていてもよく、R1およびR2の炭素数の合計は8〜20であり、R1およびR2のうちの炭素数の多い方の炭素数は5〜20である。)
前記多環式芳香族化合物を含有する有機材料を0.01〜20.0nm/秒で蒸着することにより、自己組織化した多環式芳香族化合物を含有する有機層を形成する、有機電界発光素子の製造方法。
本願発明は、下記一般式(1)で表される多環式芳香族化合物である。
Ar1、Ar2およびAr3は、それぞれ独立して、炭素数7〜20の2価の芳香族基またはヘテロ芳香族基であり、Ar2およびAr3は共に芳香族基であるかまたは共にヘテロ芳香族基であり、Ar1、Ar2およびAr3における少なくとも1つの水素は炭素数1〜4のアルキル基で置換されていてもよく、
Ar1、Ar2、およびAr3の炭素数の合計は24〜38であり、
上記式(1)中に図示した2つのp−フェニレン基における少なくとも1つの水素はメチル基で置換されていてもよく、
Ar1と結合する2つのp−フェニレン基の間の結合軸が成す角度は120〜240度であり、
R1およびR2は、それぞれ独立して、水素または炭素数1〜20のアルキル基であり、当該アルキル基における任意のメチレン基(−CH2−)は−O−または−S−で置き換わっていてもよく、R1およびR2の炭素数の合計は8〜20であり、R1およびR2のうちの炭素数の多い方の炭素数は5〜20である。
Ar1、Ar2およびAr3は、炭素数7〜20の2価の芳香族基またはヘテロ芳香族基であり、脂肪族環が縮合していてもよいが構造全体として平面性が高いか、または平面的であることが必要である。二環以上からなる場合には全て芳香族環が縮合してできた構造が好ましく、これにより縮環式芳香族基の平面性をより高めることができるため、分子間力がより高まって耐アニール性をより向上させることができる。一方で、一部に脂肪族環が縮合した構造の場合は、発光効率を高めることができる場合もあるため、Ar1、Ar2およびAr3の全体構造はこれらのバランスを考慮して設計することが好ましく、Ar1、Ar2、およびAr3の炭素数の合計は、24〜38であり、30〜35がより好ましい。
式(1)中に図示した2つのp−フェニレンとしては、それぞれ独立して、1,4−フェニレン、2−メチル−1,4−フェニレン、3−メチル−1,4−フェニレン、2,3−ジメチル−1,4−フェニレン、2,5−ジメチル−1,4−フェニレン、2,6−ジメチル−1,4−フェニレン、または3,5−ジメチル−1,4−フェニレンであり、1,4−フェニレン、2,5−ジメチル−1,4−フェニレン、2,6−ジメチル−1,4−フェニレンまたは3,5−ジメチル−1,4−フェニレンが好ましく、1,4−フェニレンが特に好ましい。
Ar1と結合する2つのp−フェニレン基の間の結合軸が成す角度は120〜240度であり、好ましくは140〜220度であり、より好ましくは160〜200度であり、特に好ましくは180度である。2つの結合軸が成す角度を120〜240度にすると、分子配向の乱れが減り、熱によるモルフォロジー変化の減少が期待できる。
R1およびR2は、それぞれ独立して、水素または炭素数1〜20の直鎖アルキル基であり、水素または炭素数1〜14の直鎖アルキル基が好ましく、水素または炭素数1〜12の直鎖アルキル基がより好ましい。R1およびR2の炭素数の合計は、8〜20であり、9〜16が好ましく、10〜14がより好ましい。また、このアルキル基における少なくとも1つの水素はメチル基で置換されていてもよい。メチル基が置換する場合には、置換基数は1〜3個が好ましく、1〜2個がより好ましく、1個が特に好ましい。
本発明の多環式芳香族化合物は、分子の適切な位置に、適切な数の、適切な鎖長の、直鎖のアルキル基を配置し、分子の適切な位置に、適切な数の、適切な大きさの芳香族基を対称的に配置し、また複数のヘテロ原子を対称的に配置することによって安定性の高い自己組織化が可能となる。アルキル基または芳香族基(以下、ここではヘテロ原子を含有するヘテロ芳香族基を含む)が配置される適切な位置や数とは、分子のアルキル基または芳香族環部分同士の相互作用が有効に働く距離に自己組織化させるのに適した位置や数であり、多環式芳香族化合物の構造に応じて異なる。不適切な位置に置換したアルキル基または芳香族基、必要以上の数のアルキル基または芳香族基は、アルキル基同士または芳香族環同士の相互作用の方向を制限したり、アルキル基同士または芳香族環同士の相互作用を弱めてしまったり、不均衡な相互作用により組織化の安定性が低下する要因となる。また、アルキル基の適切な鎖長とは、アルキル基が短すぎる場合には自己組織化が起こりにくく、アルキル基が長すぎる場合はアルキル基の折りたたみにより自己組織化の効果が薄れ、すなわち分子の芳香族環部分同士の相互作用が弱くなるため、これらの間の鎖長が適切な鎖長である。適切な大きさの芳香族基も安定な自己組織化のために不可欠であり、組織化後に加えられる熱エネルギーに耐える必要がある。大きな芳香族基の数が多くなると分子間相互作用が大きくなりすぎ、昇華エネルギーが熱分解エネルギーを超えて蒸着時に材料の分解を引き起こすことになる。芳香族基を分子内で適度に対称的に配置することは熱によって変化しにくい安定な組織を形成させることに重要であり、ヘテロ原子を分子内で対称的に配置させることは分子の双極子モーメントを小さくし、誘電分極による駆動電圧上昇の抑制に寄与する。
自己組織化を行わせるために必要なエネルギーは、蒸着時の分子の衝突または素子作製中に加えられる熱エネルギーにより賄われる。分子の衝突とは、蒸着源から飛び出た分子が基板または基板上に成膜された分子と衝突することである。飛行分子の運動エネルギーが衝突によって熱エネルギーに変換され、放熱分を差し引いた熱エネルギーが自己組織化に用いられる。従って、成膜速度が速いほど、熱が貯えられ、自己組織化が促進される。また材料分子の炭素数が多いほど昇華潜熱が大きくなり、蒸着源から飛び出た分子の熱エネルギーも大きくなるため、自己組織化が促進される。但し、昇華潜熱は分子の熱分解エネルギーを超えてはならず、材料分子の炭素数には上限がある。成膜速度は、材料分子の構造やアルキル鎖長などによっても異なり、特に限定されることはないが、0.01nm/秒〜20.0nm/秒である。成膜速度を好ましくは0.2nm/秒以上、より好ましくは0.5nm/秒以上、さらに好ましくは1nm/秒以上とすることで自己組織化の程度を高めることができる。
一般式(1)で表される多環式芳香族化合物は、公知の方法によりハロゲン化アリール(またはアリールトリフラート)とアリールボロン酸(またはアリール金属化合物やボロン酸エステル)を出発原料として、鈴木・宮浦カップリング、熊田・玉尾・コリューカップリング、根岸カップリング、薗頭・萩原カップリング、ハロゲン化反応、脱保護反応、トリフラート化反応、またはホウ酸化反応などを適宜組み合わせて合成することができる。
本発明に係る多環式芳香族化合物は、例えば、有機電界発光素子の材料として用いることができる。以下に、本実施形態に係る有機EL素子について図面に基づいて詳細に説明する。図1は、本実施形態に係る有機EL素子を示す概略断面図である。
図1に示された有機電界発光素子100は、基板101と、基板101上に設けられた陽極102と、陽極102の上に設けられた正孔注入層103と、正孔注入層103の上に設けられた正孔輸送層104と、正孔輸送層104の上に設けられた発光層105と、発光層105の上に設けられた電子輸送層106と、電子輸送層106の上に設けられた電子注入層107と、電子注入層107の上に設けられた陰極108とを有する。
基板101は、有機電界発光素子100の支持体となるものであり、通常、石英、ガラス、金属、プラスチックなどが用いられる。基板101は、目的に応じて板状、フィルム状、またはシート状に形成され、例えば、ガラス板、金属板、金属箔、プラスチックフィルム、プラスチックシートなどが用いられる。なかでも、ガラス板、および、ポリエステル、ポリメタクリレート、ポリカーボネート、ポリスルホンなどの透明な合成樹脂製の板が好ましい。ガラス基板であれば、ソーダライムガラスや無アルカリガラスなどが用いられ、また、厚みも機械的強度を保つのに十分な厚みがあればよいので、例えば、0.2mm以上あればよい。厚さの上限値としては、例えば、2mm以下、好ましくは1mm以下である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、SiO2などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用することができる。また、基板101には、ガスバリア性を高めるために、少なくとも片面に緻密なシリコン酸化膜などのガスバリア膜を設けてもよく、特にガスバリア性が低い合成樹脂製の板、フィルムまたはシートを基板101として用いる場合にはガスバリア膜を設けるのが好ましい。
陽極102は、発光層105へ正孔を注入する役割を果たすものである。なお、陽極102と発光層105との間に正孔注入層103および/または正孔輸送層104が設けられている場合には、これらを介して発光層105へ正孔を注入することになる。
正孔注入層103は、陽極102から移動してくる正孔を、効率よく発光層105内または正孔輸送層104内に注入する役割を果たすものである。正孔輸送層104は、陽極102から注入された正孔または陽極102から正孔注入層103を介して注入された正孔を、効率よく発光層105に輸送する役割を果たすものである。正孔注入層103および正孔輸送層104は、それぞれ、正孔注入・輸送材料の一種または二種以上を積層、混合するか、正孔注入・輸送材料と高分子結着剤の混合物により形成される。また、正孔注入・輸送材料に塩化鉄(III)のような無機塩を添加して層を形成してもよい。
発光層105は、電界を与えられた電極間において、陽極102から注入された正孔と、陰極108から注入された電子とを再結合させることにより発光するものである。発光層105を形成する材料としては、正孔と電子との再結合によって励起されて発光する化合物(発光性化合物)であればよく、安定な薄膜形状を形成することができ、かつ、固体状態で強い発光(蛍光)効率を示す化合物であるのが好ましい。本発明では、発光層用の材料として、上記一般式(1)で表される多環式芳香族化合物を用いることができる。
また、特開2003-347056号公報、および特開2001-307884号公報などに記載されたスチルベン構造を有するアミンを用いてもよい。
また、特開平11-97178号公報、特開2000-133457号公報、特開2000-26324号公報、特開2001-267079号公報、特開2001-267078号公報、特開2001-267076号公報、特開2000-34234号公報、特開2001-267075号公報、および特開2001-217077号公報などに記載されたペリレン誘導体を用いてもよい。
また、国際公開第2000/40586号パンフレットなどに記載されたボラン誘導体を用いてもよい。
また、特開2006-156888号公報などに記載された芳香族アミン誘導体を用いてもよい。
また、特開2004-43646号公報、特開2001-76876号公報、および特開平6-298758号公報などに記載されたクマリン誘導体を用いてもよい。
電子注入層107は、陰極108から移動してくる電子を、効率よく発光層105内または電子輸送層106内に注入する役割を果たすものである。電子輸送層106は、陰極108から注入された電子または陰極108から電子注入層107を介して注入された電子を、効率よく発光層105に輸送する役割を果たすものである。電子輸送層106および電子注入層107は、それぞれ、電子輸送・注入材料の一種または二種以上を積層、混合するか、電子輸送・注入材料と高分子結着剤の混合物により形成される。
陰極108は、電子注入層107および電子輸送層106を介して、発光層105に電子を注入する役割を果たすものである。
以上の正孔注入層、正孔輸送層、発光層、電子輸送層および電子注入層に用いられる材料は単独で各層を形成することができるが、高分子結着剤としてポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリ(N−ビニルカルバゾール)、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルホン、ポリフェニレンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリアミド、エチルセルロース、酢酸ビニル樹脂、ABS樹脂、ポリウレタン樹脂などの溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂などの硬化性樹脂などに分散させて用いることも可能である。
有機電界発光素子を構成する各層は、各層を構成すべき材料を蒸着法、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、印刷法、スピンコート法またはキャスト法、コーティング法などの方法で薄膜とすることにより、形成することができる。このようにして形成された各層の膜厚については特に限定はなく、材料の性質に応じて適宜設定することができるが、通常2nm〜5000nmの範囲である。膜厚は通常、水晶発振式膜厚測定装置などで測定できる。蒸着法を用いて薄膜化する場合、その蒸着条件は、材料の種類、膜の目的とする結晶構造および会合構造などにより異なる。蒸着条件は一般的に、蒸着用ルツボの加熱温度+50〜+400℃、真空度10−6〜10−3Pa、蒸着速度0.01〜50nm/秒、基板温度−150〜+300℃、膜厚2nm〜5μmの範囲で適宜設定することが好ましい。
また、本発明は、有機電界発光素子を備えた表示装置または有機電界発光素子を備えた照明装置などにも応用することができる。
有機電界発光素子を備えた表示装置または照明装置は、本実施形態にかかる有機電界発光素子と公知の駆動装置とを接続するなど公知の方法によって製造することができ、直流駆動、パルス駆動、交流駆動など公知の駆動方法を適宜用いて駆動することができる。
1H−NMR(CDCl3):δ=0.89(t,3H,J=6.9Hz),1.27−1.46(m,18H),1.83−1.89(m,2H),2.98(t,2H,J=7.Hz),7.39−7.42(m,4H),7.55(s,1H),7.62−7.69(m,5H),7.76−7.84(m,5H),7.91−8.00(m,6H),8.10−8.12(m,1H),8.21(d,1H,J=8.5Hz),8.32(s,1H),8.51(d,1H,J=2.1Hz),9.34(s,1H),9.39(d,1H,J=2.3Hz).
1H−NMR(CDCl3):δ=0.91(t,6H,J=7.1Hz),1.33−1.48(m,12H),1.60−1.90(m,4H),2.99(t,4H,J=7.7Hz),7.38−7.41(m,4H),7.55(s,2H),7.64(d,4H,J=8.3Hz),7.81−7.84(m,4H),7.92(d,2H,J=8.7Hz),7.98(d,4H,J=8.3Hz),8.10−8.12(m,2H),8.32(s,2H),9.33(s,2H).
1H−NMR(CDCl3):δ=0.90(t,6H,J=7.0Hz),1.30−1.47(m,16H),1.84−1.90(m,4H),2.99(t,4H,J=7.6Hz),7.39−7.42(m,4H),7.58(s,2H),7.64−7.66(m,4H),7.80−7.84(m,4H),7.96−7.99(m,6H),8.09−8.13(m,4H),9.28(s,2H).
1H−NMR(CDCl3):δ=0.90(t,6H,J=6.9Hz),1.30−1.42(m,20H),1.73−1.79(m,4H),2.84(t,4H,J=7.7Hz),7.36−7.39(m,4H),7.58−7.69(m,8H),7.81−7.83(m,4H),8.01(d,2H,J=8.5Hz),8.16(d,2H,J=8.5Hz),8.25(d,2H,J=8.5Hz),8.40(d,4H,J=8.3Hz).
1H−NMR(CDCl3):δ=0.89(t,3H,J=6.9Hz),1.27−1.52(m,18H),1.90−1.96(m,2H),3.08(t,2H,J=7.9Hz),7.44−7.48(m,5H),7.55−7.59(m,2H),7.63−7.70(m,5H),7.75−7.83(m,6H),7.85−7.88(m,4H),8.15−8.27(m,4H),9.06(d,1H,J=4.3Hz).
1H−NMR(CDCl3):δ=0.90(t,6H,J=7.0Hz),1.24−1.42(m,16H),1.82−1.85(m,4H),2.96(t,4H,J=6.8Hz),3.02(s,4H),7.50−7.68(m,10H),7.80−7.99(m,10H),8.19(s,2H),9.29(s,2H).
1H−NMR(CDCl3):δ=0.89(t,6H,J=6.9Hz),1.30−1.42(m,12H),1.83−1.86(m,4H),2.96(t,4H,J=7.8Hz),3.05(s,4H),7.54(s,2H),7.59(s,2H),7.65(d,2H,J=8.0Hz),7.80−7.86(m,10H),7.91(d,2H,J=8.2Hz),7.99−8.04(m,4H),9.23(s,2H).
1H−NMR(CDCl3):δ=0.89(t,6H,J=7.1Hz),1.31−1.44(m,12H),1.64(s,6H),1.81−1.87(m,4H),2.96(t,4H,J=7.7Hz),7.51(s,2H),7.67−7.69(m,2H),7.75(d,2H,J=1.2Hz),7.81−7.86(m,12H),7.98−8.00(m,2H),8.20(s,2H),9.29(s,2H).
1H−NMR(CDCl3):δ=0.89(t,3H,J=6.9Hz),1.27−1.41(m,18H),1.72−1.78(m,2H),2.82(t,2H,J=7.6Hz),7.37−7.42(m,5H),7.51−7.69(m,7H),7.83−8.02(m,15H),8.20(s,1H),8.24(s,1H).
1H−NMR(CDCl3):δ=0.93(t,6H,J=7.1Hz),1.38−1.46(m,8H),1.85−1.91(m,4H),2.99(t,4H,J=7.6Hz),7.38−7.42(m,4H),7.58(s,2H),7.64−7.66(m,4H),7.80−7.84(m,4H),7.96−7.99(m,6H),8.08−8.13(m,4H),9.28(s,2H).
1H−NMR(CDCl3):δ=0.94(t,6H,J=7.1Hz),1.40−1.46(m,8H),1.84−1.91(m,4H),2.99(t,4H,J=7.7Hz),7.38−7.41(m,4H),7.55(s,2H),7.64(dd,4H,J=6.4Hz,1.8Hz),7.81−7.84(m,4H),7.92(d,2H,J=8.6Hz),7.98(dd,4H,J=6.4Hz,1.9Hz),8.11(dd,2H,J=8.6Hz,1.8Hz),8.32(s,2H),9.34(s,2H).
1H−NMR(CDCl3):δ=0.89(t,3H,J=6.9Hz),1.27−1.42(m,18H),1.72−1.78(m,2H),2.81(t,2H,J=7.6Hz),7.38−7.42(m,5H),7.47−7.49(m,1H),7.60−7.69(m,5H),7.81−7.99(m,11H),8.17−8.21(m,3H),8.27−8.30(m,2H),8.96−8.97(m,1H).
1H−NMR(CDCl3):δ=0.89(t,3H,J=6.9Hz),1.28−1.38(m,18H),1.67−1.72(m,2H),2.70(t,2H,J=7.7Hz),2.86(s,3H),7.33−7.47(m,7H),7.56−7.78(m,10H),7.82−7.86(m,6H),8.14−8.17(m,2H).
実施例1〜8および比較例1〜3に係る有機EL素子を作製し、それぞれ電流密度10mA/cm2印加時の駆動電圧(V)および外部量子効率(%)を測定した後、定電流駆動したときの輝度保持時間を測定した。また、アニール処理した後の有機EL素子についても、電流密度10mA/cm2印加時の駆動電圧(V)を測定した。以下、実施例および比較例について詳細に説明する。
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置(昭和真空(株)製)の基板ホルダーに固定し、HI−1を入れたモリブデン製蒸着用ボート、HI−2を入れたモリブデン製蒸着用ボート、HTを入れたモリブデン製蒸着用ボート、BHを入れたモリブデン製蒸着用ボート、BDを入れたモリブデン製蒸着用ボート、化合物(1−424)を入れたモリブデン製蒸着用ボート、Liqを入れたモリブデン製蒸着用ボート、マグネシウムを入れたモリブデン製蒸着用ボートおよび銀を入れたモリブデン製蒸着用ボートを装着した。
電子輸送材料である化合物(1−424)を化合物(1−264)に替えた以外は実施例1に準じた方法で有機EL素子を得た。実施例1と同様にして、電流密度10mA/cm2印可時の特性を測定すると、駆動電圧は3.69V、外部量子効率は4.1%であった。電流密度10mA/cm2を印可し、定電流駆動試験を実施した結果、初期輝度の90%以上の輝度を保持する時間は48時間であった。また、アニール処理を行った素子の電流密度10mA/cm2印可時の駆動電圧は3.93Vであり、アニール処理前と比較して0.24V上昇した(約1.07倍であった)。
電子輸送材料である化合物(1−424)を化合物(1−249)に替えた以外は実施例1に準じた方法で有機EL素子を得た。実施例1と同様にして、電流密度10mA/cm2印可時の特性を測定すると、駆動電圧は4.18V、外部量子効率は6.9%であった。電流密度10mA/cm2を印可し、定電流駆動試験を実施した結果、初期輝度の90%以上の輝度を保持する時間は4時間であった。また、アニール処理を行った素子の電流密度10mA/cm2印可時の駆動電圧は4.53Vであり、アニール処理前と比較して0.35V上昇した(約1.08倍であった)。
電子輸送材料である化合物(1−424)を化合物(1−409)に替えた以外は実施例1に準じた方法で有機EL素子を得た。実施例1と同様にして、電流密度10mA/cm2印可時の特性を測定すると、駆動電圧は4.10V、外部量子効率は5.7%であった。電流密度10mA/cm2を印可し、定電流駆動試験を実施した結果、初期輝度の90%以上の輝度を保持する時間は2時間であった。また、アニール処理を行った素子の電流密度10mA/cm2印可時の駆動電圧は4.25Vであり、アニール処理前と比較して0.15V上昇した(約1.04倍であった)。
電子輸送材料である化合物(1−424)を化合物(1−456)に替えた以外は実施例1に準じた方法で有機EL素子を得た。実施例1と同様にして、電流密度10mA/cm2印可時の特性を測定すると、駆動電圧は6.24V、外部量子効率は3.8%であった。電流密度10mA/cm2を印可し、定電流駆動試験を実施した結果、初期輝度の90%以上の輝度を保持する時間は10時間であった。また、アニール処理を行った素子の電流密度10mA/cm2印可時の駆動電圧は6.15Vであり、アニール処理前と比較して0.09V下降した(約0.99倍であった)。
電子輸送材料である化合物(1−424)を化合物(1−473)に替えた以外は実施例1に準じた方法で有機EL素子を得た。実施例1と同様にして、電流密度10mA/cm2印可時の特性を測定すると、駆動電圧は3.43V、外部量子効率は5.1%であった。電流密度10mA/cm2を印可し、定電流駆動試験を実施した結果、初期輝度の90%以上の輝度を保持する時間は500時間以上であった。また、アニール処理を行った素子の電流密度10mA/cm2印可時の駆動電圧は3.43Vであり、アニール処理前と比較して変化しなかった。
電子輸送材料である化合物(1−424)を比較化合物(A)に替えた以外は実施例1に準じた方法で有機EL素子を得た。実施例1と同様にして、電流密度10mA/cm2印可時の特性を測定すると、駆動電圧は4.74V、外部量子効率は4.4%であった。電流密度10mA/cm2を印可し、定電流駆動試験を実施した結果、初期輝度の90%以上の輝度を保持する時間は1時間以下であった。また、アニール処理を行った素子の電流密度10mA/cm2印可時の駆動電圧は5.78Vであり、アニール処理前と比較して1.04V上昇した(約1.22倍であった)。
電子輸送材料である化合物(1−424)を比較化合物(B)に替えた以外は実施例1に準じた方法で有機EL素子を得た。実施例1と同様にして、電流密度10mA/cm2印可時の特性を測定すると、駆動電圧は4.25V、外部量子効率は6.9%であった。電流密度10mA/cm2を印可し、定電流駆動試験を実施した結果、初期輝度の90%以上の輝度を保持する時間は1時間以下であった。また、アニール処理を行った素子の電流密度10mA/cm2印可時の駆動電圧は5.61Vであり、アニール処理前と比較して1.36V上昇した(約1.32倍であった)。
電子輸送材料である化合物(1−424)を化合物(1−249)とLiqとの混合物に替えた以外は実施例1に準じた方法で有機EL素子を得た。すなわち、電子輸送層として、化合物(1−249)の入った蒸着用ボートとLiqの入った蒸着用ボートを同時に加熱して膜厚30nmになるように蒸着して電子輸送層を形成した。化合物(1−249)とLiqの重量比がおよそ1:1になるように蒸着速度を調節した。
電子輸送材料である化合物(1−249)を化合物(1−264)に替えた以外は実施例7に準じた方法で有機EL素子を得た。実施例1と同様にして、電流密度10mA/cm2印可時の特性を測定すると、駆動電圧は3.28V、外部量子効率は5.8%であった。電流密度10mA/cm2を印可し、定電流駆動試験を実施した結果、初期輝度の90%以上の輝度を保持する時間は500時間以上であった。また、アニール処理を行った素子の電流密度10mA/cm2印可時の駆動電圧は3.22Vであり、アニール処理前と比較して0.06V下降した(約0.98倍であった)。
電子輸送材料である化合物(1−249)を比較化合物(A)に替えた以外は実施例7に準じた方法で有機EL素子を得た。実施例1と同様にして、電流密度10mA/cm2印可時の特性を測定すると、駆動電圧は4.25V、外部量子効率は5.7%であった。電流密度10mA/cm2を印可し、定電流駆動試験を実施した結果、初期輝度の90%以上の輝度を保持する時間は500時間以上であった。また、アニール処理を行った素子の電流密度10mA/cm2印可時の駆動電圧は3.11Vであり、アニール処理を行う前と比較して1.14V下降した(約0.73倍であった)。
101 基板
102 陽極
103 正孔注入層
104 正孔輸送層
105 発光層
106 電子輸送層
107 電子注入層
108 陰極
Claims (19)
- 下記一般式(1)で表される多環式芳香族化合物。
Ar1、Ar2およびAr3は、それぞれ独立して、炭素数7〜20の2価の芳香族基またはヘテロ芳香族基であり、Ar2およびAr3は共に芳香族基であるかまたは共にヘテロ芳香族基であり、Ar1、Ar2およびAr3における少なくとも1つの水素は炭素数1〜4のアルキル基で置換されていてもよく、
Ar1、Ar2、およびAr3の炭素数の合計は24〜38であり、
上記式(1)中に図示した2つのp−フェニレン基における少なくとも1つの水素はメチル基で置換されていてもよく、
Ar1と結合する2つのp−フェニレン基の間の結合軸が成す角度は120〜240度であり、
R1およびR2は、それぞれ独立して、水素または炭素数1〜20の直鎖アルキル基であり、当該直鎖アルキル基における任意のメチレン基(−CH2−)は−O−または−S−で置き換わっていてもよく、当該直鎖アルキル基における少なくとも1つの水素はメチル基で置換されていてもよく、R1およびR2の炭素数の合計は8〜20であり、R1およびR2のうちの炭素数の多い方の炭素数は5〜20である。) - Ar1、Ar2およびAr3がヘテロ芳香族基である場合のそのヘテロ元素は、それぞれ独立して、窒素、酸素および硫黄からなる群から選択される少なくとも1つである、請求項1に記載の多環式芳香族化合物。
- Ar1は炭素数7〜20の2価の芳香族基であり、Ar1における少なくとも1つの水素はメチル基で置換されていてもよい、請求項2に記載の多環式芳香族化合物。
- Ar2およびAr3は、それぞれ独立して、炭素数7〜13かつヘテロ元素数1〜2の含窒素芳香族基、含酸素芳香族基または含硫黄芳香族基であり、Ar2およびAr3における少なくとも1つの水素は炭素数1〜4のアルキル基で置換されていてもよい、請求項3に記載の多環式芳香族化合物。
- Ar1、Ar2およびAr3の炭素数の合計は30〜35である、請求項1〜4のいずれかに記載の多環式芳香族化合物。
- Ar1は、アントラセンジイル、フェナンスレンジイル、フルオレンジイルまたはジヒドロフェナンスレンジイルであり、Ar1における少なくとも1つの水素はメチル基で置換されていてもよい、請求項1〜5のいずれかに記載の多環式芳香族化合物。
- Ar2およびAr3は、それぞれ独立して、キノリンジイルまたはイソキノリンジイルであり、Ar2およびAr3における少なくとも1つの水素はメチル基で置換されていてもよい、請求項1〜6のいずれかに記載の多環式芳香族化合物。
- R1およびR2の炭素数の合計は10〜16である、請求項1〜7のいずれかに記載の多環式芳香族化合物。
- 請求項1〜9のいずれかに記載の多環式芳香族化合物が自己組織化した材料。
- 請求項10に記載の自己組織化した材料を含有する電子輸送材料。
- 陽極および陰極からなる一対の電極と、請求項1〜9のいずれかに記載の多環式芳香族化合物を含有する有機層とを有する、有機電界発光素子。
- 前記多環式芳香族化合物が自己組織化した化合物である、請求項12に記載の有機電界発光素子。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置される発光層と、前記陰極と該発光層との間に配置され、請求項11に記載の電子輸送材料を含有する電子輸送層および/または電子注入層とを有する、有機電界発光素子。
- 前記電子輸送層および電子注入層の少なくとも1つは、さらに、キノリノール系金属錯体、ピリジン誘導体、ビピリジン誘導体、フェナントロリン誘導体、ボラン誘導体およびベンゾイミダゾール誘導体からなる群から選択される少なくとも1つを含有する、請求項14に記載する有機電界発光素子。
- 前記電子輸送層および電子注入層の少なくとも1つは、さらに、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属の酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属の酸化物、アルカリ土類金属のハロゲン化物、希土類金属の酸化物、希土類金属のハロゲン化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体および希土類金属の有機錯体からなる群から選択される少なくとも1つを含有する、請求項14または15に記載する有機電界発光素子。
- 請求項12〜16のいずれかに記載する有機電界発光素子を備えた表示装置。
- 請求項12〜16のいずれかに記載する有機電界発光素子を備えた照明装置。
- 陽極および陰極からなる一対の電極と、請求項1〜9のいずれかに記載の多環式芳香族化合物を含有する有機層とを有する有機電界発光素子の製造方法であって、
前記多環式芳香族化合物を含有する有機材料を0.01〜20.0nm/秒で蒸着することにより、自己組織化した多環式芳香族化合物を含有する有機層を形成する、有機電界発光素子の製造方法。
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016067018A JP6638517B2 (ja) | 2016-03-30 | 2016-03-30 | 自己組織化し得る多環式芳香族化合物およびそれを用いた有機el素子 |
KR1020170033014A KR102353035B1 (ko) | 2016-03-30 | 2017-03-16 | 자기 조직화 가능한 다환식 방향족 화합물 및 이를 사용한 유기 el 소자 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016067018A JP6638517B2 (ja) | 2016-03-30 | 2016-03-30 | 自己組織化し得る多環式芳香族化合物およびそれを用いた有機el素子 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017178832A true JP2017178832A (ja) | 2017-10-05 |
JP6638517B2 JP6638517B2 (ja) | 2020-01-29 |
Family
ID=60005024
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016067018A Active JP6638517B2 (ja) | 2016-03-30 | 2016-03-30 | 自己組織化し得る多環式芳香族化合物およびそれを用いた有機el素子 |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP6638517B2 (ja) |
KR (1) | KR102353035B1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115521253A (zh) * | 2022-11-28 | 2022-12-27 | 烟台显华科技集团股份有限公司 | 一种双联喹啉衍生物化合物及其应用 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007072889A1 (en) * | 2005-12-20 | 2007-06-28 | Canon Kabushiki Kaisha | Fluorene compound and organic electroluminescence device |
JP2008069100A (ja) * | 2006-09-13 | 2008-03-27 | Tdk Corp | 有機el素子用化合物及び有機el素子 |
JP2009120582A (ja) * | 2007-10-26 | 2009-06-04 | Toyo Ink Mfg Co Ltd | カルバゾリル基を有する化合物およびその用途 |
JP2009173642A (ja) * | 2007-12-27 | 2009-08-06 | Chisso Corp | ピリジルフェニル基を有するアントラセン誘導体化合物及び有機電界発光素子 |
JP2009203203A (ja) * | 2008-02-29 | 2009-09-10 | Toyo Ink Mfg Co Ltd | アントラセン誘導体及びその用途 |
CN101597259A (zh) * | 2009-07-07 | 2009-12-09 | 清华大学 | 有机材料及其在有机电致发光器件中的应用 |
WO2011086864A1 (ja) * | 2010-01-15 | 2011-07-21 | 富士フイルム株式会社 | 有機電界発光素子 |
KR20130135162A (ko) * | 2012-05-31 | 2013-12-10 | 주식회사 엘지화학 | 함질소 헤테로환 화합물 및 이를 포함하는 유기 전자 소자 |
WO2014024880A1 (ja) * | 2012-08-10 | 2014-02-13 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子、および電子機器 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05182764A (ja) | 1992-01-08 | 1993-07-23 | Sekisui Chem Co Ltd | 有機電界発光素子及びその製造方法 |
JPH10284248A (ja) | 1997-04-03 | 1998-10-23 | Toyota Motor Corp | 有機el素子の製造方法 |
JPH1140352A (ja) | 1997-07-11 | 1999-02-12 | Tdk Corp | 有機el素子およびその製造方法 |
JP4310843B2 (ja) | 1999-04-26 | 2009-08-12 | 株式会社豊田中央研究所 | 有機電界発光素子の製造方法 |
JP5114952B2 (ja) | 2000-03-31 | 2013-01-09 | セイコーエプソン株式会社 | エレクトロルミネッセンス素子、及びエレクトロルミネッセンス素子の製造方法 |
JP4407102B2 (ja) | 2001-08-06 | 2010-02-03 | 三菱化学株式会社 | アントラセン系化合物、その製造方法および有機電界発光素子 |
JP4138282B2 (ja) | 2001-09-14 | 2008-08-27 | シャープ株式会社 | 有機エレクトロルミネッセンス素子の製造方法 |
JP3926180B2 (ja) | 2002-03-26 | 2007-06-06 | シャープ株式会社 | 有機el発光素子およびそれを用いた液晶表示装置 |
JP4374174B2 (ja) | 2002-09-18 | 2009-12-02 | 日本放送協会 | 有機薄膜デバイスおよび有機elディスプレイ |
JP2005170911A (ja) | 2003-12-15 | 2005-06-30 | Idemitsu Kosan Co Ltd | 芳香族化合物およびそれを用いた有機エレクトロルミネッセンス素子 |
JP4826081B2 (ja) | 2004-09-29 | 2011-11-30 | 株式会社豊田中央研究所 | 有機半導体材料、それを用いた半導体装置及び電界効果トランジスタ |
JP4801907B2 (ja) | 2005-01-27 | 2011-10-26 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子用透明電極、有機エレクトロルミネッセンス素子及びその製造方法 |
JP2007109524A (ja) | 2005-10-14 | 2007-04-26 | Fujifilm Corp | 有機el材料及びその製造方法 |
JP5335379B2 (ja) | 2008-11-12 | 2013-11-06 | 学校法人東海大学 | 有機半導体材料及びこれを使用する有機電子デバイス |
JP2011102271A (ja) | 2009-11-11 | 2011-05-26 | Japan Science & Technology Agency | ヘキサベンゾコロネン−ジアリールエテン連結分子からなる同軸ナノチューブによる光導電性の変調 |
-
2016
- 2016-03-30 JP JP2016067018A patent/JP6638517B2/ja active Active
-
2017
- 2017-03-16 KR KR1020170033014A patent/KR102353035B1/ko active IP Right Grant
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007072889A1 (en) * | 2005-12-20 | 2007-06-28 | Canon Kabushiki Kaisha | Fluorene compound and organic electroluminescence device |
JP2008069100A (ja) * | 2006-09-13 | 2008-03-27 | Tdk Corp | 有機el素子用化合物及び有機el素子 |
JP2009120582A (ja) * | 2007-10-26 | 2009-06-04 | Toyo Ink Mfg Co Ltd | カルバゾリル基を有する化合物およびその用途 |
JP2009173642A (ja) * | 2007-12-27 | 2009-08-06 | Chisso Corp | ピリジルフェニル基を有するアントラセン誘導体化合物及び有機電界発光素子 |
JP2009203203A (ja) * | 2008-02-29 | 2009-09-10 | Toyo Ink Mfg Co Ltd | アントラセン誘導体及びその用途 |
CN101597259A (zh) * | 2009-07-07 | 2009-12-09 | 清华大学 | 有机材料及其在有机电致发光器件中的应用 |
WO2011086864A1 (ja) * | 2010-01-15 | 2011-07-21 | 富士フイルム株式会社 | 有機電界発光素子 |
KR20130135162A (ko) * | 2012-05-31 | 2013-12-10 | 주식회사 엘지화학 | 함질소 헤테로환 화합물 및 이를 포함하는 유기 전자 소자 |
WO2014024880A1 (ja) * | 2012-08-10 | 2014-02-13 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子、および電子機器 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115521253A (zh) * | 2022-11-28 | 2022-12-27 | 烟台显华科技集团股份有限公司 | 一种双联喹啉衍生物化合物及其应用 |
Also Published As
Publication number | Publication date |
---|---|
JP6638517B2 (ja) | 2020-01-29 |
KR102353035B1 (ko) | 2022-01-19 |
KR20170113125A (ko) | 2017-10-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5786578B2 (ja) | 発光層用材料およびこれを用いた有機電界発光素子 | |
JP5796582B2 (ja) | 新規アントラセン化合物およびこれを用いた有機電界発光素子 | |
JP5982966B2 (ja) | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 | |
TW201926760A (zh) | 有機元件用材料、有機電場發光元件、顯示裝置及照明裝置 | |
TW201703305A (zh) | 有機電場發光元件 | |
WO2018146962A1 (ja) | 有機電界発光素子 | |
JP6156389B2 (ja) | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 | |
JP5824827B2 (ja) | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 | |
WO2013077141A1 (ja) | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 | |
WO2015005440A1 (ja) | 環縮合フルオレン化合物またはフルオレン化合物を含む発光補助層用材料 | |
JP2011037838A (ja) | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 | |
JP6341315B2 (ja) | 発光層用材料およびこれを用いた有機電界発光素子 | |
TWI631094B (zh) | 蒽系化合物、發光層用材料、使用其的有機電致發光元件、顯示裝置及照明裝置 | |
JP5949779B2 (ja) | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 | |
JP6464985B2 (ja) | 自己組織化し得る多環式芳香族化合物およびそれを用いた有機el素子 | |
JP5794155B2 (ja) | 新規な2,7−ビスアントリルナフタレン化合物およびこれを用いた有機電界発光素子 | |
WO2018146894A1 (ja) | 有機電界発光素子 | |
JP5776384B2 (ja) | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 | |
JP6349902B2 (ja) | アントラセン誘導体および有機el素子 | |
JP6638517B2 (ja) | 自己組織化し得る多環式芳香族化合物およびそれを用いた有機el素子 | |
JP5867269B2 (ja) | ベンゾフルオレン化合物、該化合物を用いた発光層用材料および有機電界発光素子 | |
JP5920432B2 (ja) | 縮合ピロール多環化合物、発光層用材料およびこれを用いた有機電界発光素子 | |
JP6610447B2 (ja) | 自己組織化し得る多環式芳香族化合物およびそれを用いた有機el素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20181015 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190716 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20190711 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190905 |
|
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: 20191126 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20191209 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6638517 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |