JP5786578B2

JP5786578B2 - 発光層用材料およびこれを用いた有機電界発光素子

発光層用材料およびこれを用いた有機電界発光素子 Download PDF

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Publication number: JP5786578B2
Authority: JP; Japan
Prior art keywords: derivatives; formula; compound; light emitting; emitting layer
Prior art date: 2010-10-15
Legal status : Active

Application number

JP2011201298A

Other languages

English (en)

Japanese (ja)

Other versions

JP2012104806A (ja

Inventor

俊弘小池

国防王

Current Assignee

JNC Corp

Original Assignee

JNC Corp

Priority date

2010-10-15

Filing date

2011-09-15

Publication date

2015-09-30

2011-09-15 Application filed by JNC Corp filed Critical JNC Corp

2011-09-15 Priority to JP2011201298A priority Critical patent/JP5786578B2/ja

2012-05-31 Publication of JP2012104806A publication Critical patent/JP2012104806A/ja

2015-09-30 Application granted granted Critical

2015-09-30 Publication of JP5786578B2 publication Critical patent/JP5786578B2/ja

Status Active legal-status Critical Current

2031-09-15 Anticipated expiration legal-status Critical

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239000000463 material Substances 0.000 title claims description 127
150000001875 compounds Chemical class 0.000 claims description 194
-1 biphenylyl Chemical group 0.000 claims description 133
238000002347 injection Methods 0.000 claims description 77
239000007924 injection Substances 0.000 claims description 77
125000004432 carbon atom Chemical group C* 0.000 claims description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 21
150000002431 hydrogen Chemical class 0.000 claims description 13
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000001624 naphthyl group Chemical group 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
125000005561 phenanthryl group Chemical group 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
150000004982 aromatic amines Chemical class 0.000 claims description 8
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 8
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
150000001342 alkaline earth metals Chemical class 0.000 claims description 7
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 7
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
229910052805 deuterium Inorganic materials 0.000 claims description 6
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 claims description 5
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 claims description 4
150000004696 coordination complex 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
229910001507 metal halide Inorganic materials 0.000 claims description 2
150000005309 metal halides Chemical class 0.000 claims description 2
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
239000010410 layer Substances 0.000 description 253
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 159
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
238000006243 chemical reaction Methods 0.000 description 81
238000007740 vapor deposition Methods 0.000 description 75
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
229910052757 nitrogen Inorganic materials 0.000 description 62
239000000758 substrate Substances 0.000 description 52
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239000010408 film Substances 0.000 description 43
238000000151 deposition Methods 0.000 description 42
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 41
238000005401 electroluminescence Methods 0.000 description 41
125000003118 aryl group Chemical group 0.000 description 40
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 39
230000008021 deposition Effects 0.000 description 39
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 38
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 37
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 37
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239000011733 molybdenum Substances 0.000 description 37
229910052782 aluminium Inorganic materials 0.000 description 35
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
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238000000034 method Methods 0.000 description 30
239000012046 mixed solvent Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 30
230000005525 hole transport Effects 0.000 description 29
238000000746 purification Methods 0.000 description 29
230000015572 biosynthetic process Effects 0.000 description 28
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 28
239000012043 crude product Substances 0.000 description 27
238000003786 synthesis reaction Methods 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
229910052751 metal Inorganic materials 0.000 description 25
239000002184 metal Substances 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
239000002244 precipitate Substances 0.000 description 24
125000001424 substituent group Chemical group 0.000 description 22
239000012299 nitrogen atmosphere Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 20
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 20
239000002019 doping agent Substances 0.000 description 20
238000010438 heat treatment Methods 0.000 description 20
229910052749 magnesium Inorganic materials 0.000 description 20
239000011777 magnesium Substances 0.000 description 20
229910052709 silver Inorganic materials 0.000 description 20
239000004332 silver Substances 0.000 description 20
239000000243 solution Substances 0.000 description 19
229910000160 potassium phosphate Inorganic materials 0.000 description 17
235000011009 potassium phosphates Nutrition 0.000 description 17
238000012360 testing method Methods 0.000 description 17
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 16
230000000052 comparative effect Effects 0.000 description 15
239000011521 glass Substances 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
238000005160 1H NMR spectroscopy Methods 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 12
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 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
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
238000001228 spectrum Methods 0.000 description 12
125000003107 substituted aryl group Chemical group 0.000 description 12
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
239000000126 substance Substances 0.000 description 11
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
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 10
229910052792 caesium Inorganic materials 0.000 description 9
125000004435 hydrogen atom Chemical group [H]* 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
239000010409 thin film Substances 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 8
239000011159 matrix material Substances 0.000 description 8
238000005259 measurement Methods 0.000 description 8
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 8
238000000859 sublimation Methods 0.000 description 8
230000008022 sublimation Effects 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
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 7
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 7
150000001543 aryl boronic acids Chemical class 0.000 description 7
150000004775 coumarins Chemical class 0.000 description 7
125000004093 cyano group Chemical group *C#N 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
238000004544 sputter deposition Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
NWUWLVCEYBABOV-UHFFFAOYSA-N [7-(trifluoromethylsulfonyloxy)naphthalen-2-yl] trifluoromethanesulfonate Chemical compound C1=CC(OS(=O)(=O)C(F)(F)F)=CC2=CC(OS(=O)(=O)C(F)(F)F)=CC=C21 NWUWLVCEYBABOV-UHFFFAOYSA-N 0.000 description 6
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
239000004305 biphenyl Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
125000000753 cycloalkyl group Chemical group 0.000 description 6
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
150000002739 metals Chemical class 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
125000000623 heterocyclic group Chemical group 0.000 description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
238000005498 polishing Methods 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 4
JCYLGNNXACDGDA-UHFFFAOYSA-N (7-methoxynaphthalen-2-yl) trifluoromethanesulfonate Chemical compound C1=CC(OS(=O)(=O)C(F)(F)F)=CC2=CC(OC)=CC=C21 JCYLGNNXACDGDA-UHFFFAOYSA-N 0.000 description 4
YVKKYTCMGJRCRS-UHFFFAOYSA-N 9-(7-methoxynaphthalen-2-yl)-10-phenylanthracene Chemical class COC1=CC=C2C=CC(=CC2=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C2)C2=CC=CC=C12 YVKKYTCMGJRCRS-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
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 4
0 CC(C)(N([Al])[Al]*)I=* Chemical compound CC(C)(N([Al])[Al]*)I=* 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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000006069 Suzuki reaction reaction Methods 0.000 description 4
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 4
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
150000001716 carbazoles Chemical class 0.000 description 4
239000012295 chemical reaction liquid Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000010432 diamond Substances 0.000 description 4
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 4
239000007789 gas Substances 0.000 description 4
230000009477 glass transition Effects 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
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
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 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
239000000047 product Substances 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000000547 substituted alkyl group Chemical group 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 4
HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 3
YCHOQCUJHCRPGK-UHFFFAOYSA-N (7-phenylnaphthalen-2-yl) trifluoromethanesulfonate Chemical compound FC(S(=O)(=O)OC1=CC2=CC(=CC=C2C=C1)C1=CC=CC=C1)(F)F YCHOQCUJHCRPGK-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
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
NFENWQTZSBIIPT-UHFFFAOYSA-N 7-(10-phenylanthracen-9-yl)naphthalen-2-ol Chemical compound C1(=CC=CC=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=C2C=CC(=CC2=C1)O NFENWQTZSBIIPT-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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