TWI660959B

TWI660959B - 金屬錯合物

金屬錯合物 Download PDF

Info

Publication number: TWI660959B
Authority: TW; Taiwan
Prior art keywords: group; groups; atoms; substituted; cyc
Prior art date: 2014-01-13

Application number

TW104100734A

Other languages

English (en)

Chinese (zh)

Other versions

TW201540720A (zh

Inventor

菲利普史托希爾

尼爾斯柯尼恩

Original Assignee

德商麥克專利有限公司

Priority date

2014-01-13

Filing date

2015-01-09

Publication date

2019-06-01

2015-01-09 Application filed by 德商麥克專利有限公司 filed Critical 德商麥克專利有限公司

2015-11-01 Publication of TW201540720A publication Critical patent/TW201540720A/zh

2019-06-01 Application granted granted Critical

2019-06-01 Publication of TWI660959B publication Critical patent/TWI660959B/zh

Links

229910052751 metal Inorganic materials 0.000 title claims abstract description 46
239000002184 metal Substances 0.000 title claims abstract description 46
238000005401 electroluminescence Methods 0.000 claims abstract description 9
239000000203 mixture Substances 0.000 claims description 137
150000001875 compounds Chemical class 0.000 claims description 113
-1 alkylcyano Chemical compound 0.000 claims description 105
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 101
239000003446 ligand Substances 0.000 claims description 101
125000003118 aryl group Chemical group 0.000 claims description 96
125000004432 carbon atom Chemical group C* 0.000 claims description 75
239000002904 solvent Substances 0.000 claims description 54
229920000642 polymer Polymers 0.000 claims description 33
238000000034 method Methods 0.000 claims description 32
125000001072 heteroaryl group Chemical group 0.000 claims description 30
229910052741 iridium Inorganic materials 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 27
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 26
229910052799 carbon Inorganic materials 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 20
150000004696 coordination complex Chemical class 0.000 claims description 20
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 18
229910052731 fluorine Inorganic materials 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
230000007935 neutral effect Effects 0.000 claims description 18
229910052794 bromium Inorganic materials 0.000 claims description 17
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
229910052805 deuterium Inorganic materials 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 14
125000002950 monocyclic group Chemical group 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000000412 dendrimer Substances 0.000 claims description 12
229920000736 dendritic polymer Polymers 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
238000006467 substitution reaction Methods 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000006165 cyclic alkyl group Chemical group 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 9
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
229910052697 platinum Chemical group 0.000 claims description 8
235000000621 Bidens tripartita Nutrition 0.000 claims description 7
240000004082 Bidens tripartita Species 0.000 claims description 7
239000005977 Ethylene Substances 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 7
208000006637 fused teeth Diseases 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
150000001450 anions Chemical class 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
125000003367 polycyclic group Chemical group 0.000 claims description 5
238000007363 ring formation reaction Methods 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
150000002430 hydrocarbons Chemical group 0.000 claims description 4
150000002504 iridium compounds Chemical class 0.000 claims description 4
MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical group [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 claims description 4
239000012948 isocyanate Substances 0.000 claims description 4
229910052762 osmium Inorganic materials 0.000 claims description 4
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
150000004703 alkoxides Chemical class 0.000 claims description 3
150000001409 amidines Chemical class 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
150000007942 carboxylates Chemical class 0.000 claims description 3
125000005266 diarylamine group Chemical group 0.000 claims description 3
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 claims description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
125000005015 aryl alkynyl group Chemical group 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
125000004986 diarylamino group Chemical group 0.000 claims description 2
125000005240 diheteroarylamino group Chemical group 0.000 claims description 2
230000005669 field effect Effects 0.000 claims description 2
125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
150000002466 imines Chemical class 0.000 claims description 2
150000002513 isocyanates Chemical class 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
230000001699 photocatalysis Effects 0.000 claims description 2
238000007146 photocatalysis Methods 0.000 claims description 2
108091008695 photoreceptors Proteins 0.000 claims description 2
238000010791 quenching Methods 0.000 claims description 2
230000000171 quenching effect Effects 0.000 claims description 2
239000010409 thin film Substances 0.000 claims description 2
125000002355 alkine group Chemical group 0.000 claims 1
150000002540 isothiocyanates Chemical class 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 156
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 124
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
239000007787 solid Substances 0.000 description 53
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 50
238000005160 1H NMR spectroscopy Methods 0.000 description 44
238000001816 cooling Methods 0.000 description 44
239000000243 solution Substances 0.000 description 44
238000000859 sublimation Methods 0.000 description 42
230000008022 sublimation Effects 0.000 description 42
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 40
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
239000000463 material Substances 0.000 description 37
238000010992 reflux Methods 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 29
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
239000012074 organic phase Substances 0.000 description 28
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
239000005909 Kieselgur Substances 0.000 description 25
229910052943 magnesium sulfate Inorganic materials 0.000 description 25
235000019341 magnesium sulphate Nutrition 0.000 description 25
239000011541 reaction mixture Substances 0.000 description 25
239000000741 silica gel Substances 0.000 description 24
229910002027 silica gel Inorganic materials 0.000 description 24
239000000725 suspension Substances 0.000 description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
230000015572 biosynthetic process Effects 0.000 description 21
239000011521 glass Substances 0.000 description 21
238000003756 stirring Methods 0.000 description 21
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
238000009835 boiling Methods 0.000 description 20
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 20
239000000706 filtrate Substances 0.000 description 19
238000003786 synthesis reaction Methods 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
239000000460 chlorine Substances 0.000 description 18
239000011159 matrix material Substances 0.000 description 17
239000012043 crude product Substances 0.000 description 16
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 16
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 16
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
239000012047 saturated solution Substances 0.000 description 15
239000011324 bead Substances 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
125000001246 bromo group Chemical group Br* 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
239000008096 xylene Substances 0.000 description 13
VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 12
SECXISVLQFMRJM-UHFFFAOYSA-N NMP Substances CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 11
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
239000003708 ampul Substances 0.000 description 10
230000000903 blocking effect Effects 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
125000004122 cyclic group Chemical group 0.000 description 10
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
238000000746 purification Methods 0.000 description 10
229910000404 tripotassium phosphate Inorganic materials 0.000 description 10
235000019798 tripotassium phosphate Nutrition 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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238000004128 high performance liquid chromatography Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
239000007858 starting material Substances 0.000 description 9
239000000758 substrate Substances 0.000 description 9
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
230000005525 hole transport Effects 0.000 description 8
238000002347 injection Methods 0.000 description 8
239000007924 injection Substances 0.000 description 8
238000007639 printing Methods 0.000 description 8
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 8
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000002585 base Substances 0.000 description 7
125000002619 bicyclic group Chemical group 0.000 description 7
239000004327 boric acid Substances 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
238000000605 extraction Methods 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
229940078552 o-xylene Drugs 0.000 description 7
150000003003 phosphines Chemical class 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
238000007740 vapor deposition Methods 0.000 description 7
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 6
229940093475 2-ethoxyethanol Drugs 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
241000208340 Araliaceae Species 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 6
235000003140 Panax quinquefolius Nutrition 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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 6
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 6
235000008434 ginseng Nutrition 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
150000002739 metals Chemical class 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
239000000178 monomer Substances 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
239000012071 phase Substances 0.000 description 6
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
229910052709 silver Inorganic materials 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
238000004528 spin coating Methods 0.000 description 6
239000012258 stirred mixture Substances 0.000 description 6
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