KR102289321B1

KR102289321B1 - 환축합 플루오렌 화합물 또는 플루오렌 화합물을 포함하는 발광보조층용 재료

환축합 플루오렌 화합물 또는 플루오렌 화합물을 포함하는 발광보조층용 재료 Download PDF

Info

Publication number: KR102289321B1
Authority: KR; South Korea
Prior art keywords: formula; compound; light emitting; layer; aryl
Prior art date: 2013-07-10

Application number

KR1020167003104A

Other languages

English (en)

Korean (ko)

Other versions

KR20160040198A (ko

Inventor

아츠시 오노

토시히로 코이케

신타로 노무라

Original Assignee

에스케이머티리얼즈제이엔씨 주식회사

Priority date

2013-07-10

Filing date

2014-07-10

Publication date

2021-08-11

2014-07-10 Application filed by 에스케이머티리얼즈제이엔씨 주식회사 filed Critical 에스케이머티리얼즈제이엔씨 주식회사

2016-04-12 Publication of KR20160040198A publication Critical patent/KR20160040198A/ko

2021-08-11 Application granted granted Critical

2021-08-11 Publication of KR102289321B1 publication Critical patent/KR102289321B1/ko

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-1 fluorene compound Chemical class 0.000 title claims abstract description 413
239000000463 material Substances 0.000 title claims description 270
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title abstract description 77
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 105
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 38
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 25
125000003118 aryl group Chemical group 0.000 claims description 144
125000001424 substituent group Chemical group 0.000 claims description 99
125000004432 carbon atom Chemical group C* 0.000 claims description 94
239000002019 doping agent Substances 0.000 claims description 66
150000001412 amines Chemical class 0.000 claims description 43
238000000034 method Methods 0.000 claims description 34
125000001624 naphthyl group Chemical group 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
125000005561 phenanthryl group Chemical group 0.000 claims description 22
150000003220 pyrenes Chemical class 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 19
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 19
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 18
125000005504 styryl group Chemical group 0.000 claims description 17
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
150000001454 anthracenes Chemical class 0.000 claims description 12
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 11
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
150000001846 chrysenes Chemical class 0.000 claims description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
150000007979 thiazole derivatives Chemical class 0.000 claims description 7
150000002391 heterocyclic compounds Chemical class 0.000 claims description 6
150000003222 pyridines Chemical class 0.000 claims description 6
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 5
125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 3
150000005041 phenanthrolines Chemical class 0.000 claims description 3
229930194845 Bahia Natural products 0.000 claims description 2
235000017858 Laurus nobilis Nutrition 0.000 claims description 2
241000132007 Bahia Species 0.000 claims 1
239000010410 layer Substances 0.000 description 395
150000001875 compounds Chemical class 0.000 description 265
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 213
125000000217 alkyl group Chemical group 0.000 description 85
238000002347 injection Methods 0.000 description 74
239000007924 injection Substances 0.000 description 74
125000000753 cycloalkyl group Chemical group 0.000 description 66
239000002904 solvent Substances 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
230000015572 biosynthetic process Effects 0.000 description 47
238000003786 synthesis reaction Methods 0.000 description 47
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 39
229910052782 aluminium Inorganic materials 0.000 description 39
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 38
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
238000000746 purification Methods 0.000 description 33
239000000243 solution Substances 0.000 description 32
229910052739 hydrogen Inorganic materials 0.000 description 31
239000001257 hydrogen Substances 0.000 description 31
239000012299 nitrogen atmosphere Substances 0.000 description 31
238000001308 synthesis method Methods 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
239000000758 substrate Substances 0.000 description 27
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 26
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
230000005525 hole transport Effects 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
239000012044 organic layer Substances 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
239000012043 crude product Substances 0.000 description 21
239000000203 mixture Substances 0.000 description 21
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 21
NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 20
229910002027 silica gel Inorganic materials 0.000 description 20
239000000741 silica gel Substances 0.000 description 20
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
238000010438 heat treatment Methods 0.000 description 19
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
239000002994 raw material Substances 0.000 description 19
239000010408 film Substances 0.000 description 18
125000001072 heteroaryl group Chemical group 0.000 description 18
239000007787 solid Substances 0.000 description 18
238000007740 vapor deposition Methods 0.000 description 18
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 17
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 17
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 16
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 16
229910052805 deuterium Inorganic materials 0.000 description 16
150000002431 hydrogen Chemical class 0.000 description 16
238000004519 manufacturing process Methods 0.000 description 16
239000012046 mixed solvent Substances 0.000 description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 14
125000003277 amino group Chemical group 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
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 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 12
229910052751 metal Inorganic materials 0.000 description 12
239000002184 metal Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 11
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 11
0 C1C=CC=*C1c(cc1)ccc1-c1ccc(C2c3ccccc3C([C@]3C=CC(c4ccccc4)=CC3)=CC2C2(c3ccccc3)c3ccccc3)c2c1 Chemical compound C1C=CC=*C1c(cc1)ccc1-c1ccc(C2c3ccccc3C([C@]3C=CC(c4ccccc4)=CC3)=CC2C2(c3ccccc3)c3ccccc3)c2c1 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 11
239000007983 Tris buffer Substances 0.000 description 11
239000011521 glass Substances 0.000 description 11
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 11
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
125000005346 substituted cycloalkyl group Chemical group 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
230000000052 comparative effect Effects 0.000 description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 10
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
238000000859 sublimation Methods 0.000 description 10
230000008022 sublimation Effects 0.000 description 10
125000005577 anthracene group Chemical group 0.000 description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
238000000151 deposition Methods 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
125000001931 aliphatic group Chemical group 0.000 description 8
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 8
230000008021 deposition Effects 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 8
239000011159 matrix material Substances 0.000 description 8
229910052750 molybdenum Inorganic materials 0.000 description 8
239000011733 molybdenum Substances 0.000 description 8
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 8
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
229910000160 potassium phosphate Inorganic materials 0.000 description 8
235000011009 potassium phosphates Nutrition 0.000 description 8
230000006798 recombination Effects 0.000 description 8
238000005215 recombination Methods 0.000 description 8
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
239000010409 thin film Substances 0.000 description 8
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 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 7
230000004888 barrier function Effects 0.000 description 7
229910052792 caesium Inorganic materials 0.000 description 7
150000002739 metals Chemical class 0.000 description 7
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 7
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
125000004076 pyridyl group Chemical group 0.000 description 7
238000001228 spectrum Methods 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
125000005580 triphenylene group Chemical group 0.000 description 7
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 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
239000011259 mixed solution Substances 0.000 description 6
125000005581 pyrene group Chemical group 0.000 description 6
230000001603 reducing effect Effects 0.000 description 6
125000006413 ring segment Chemical group 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 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 5
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 5
238000009792 diffusion process Methods 0.000 description 5
230000005281 excited state Effects 0.000 description 5
239000011737 fluorine Substances 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
229910052749 magnesium Inorganic materials 0.000 description 5
239000011777 magnesium Substances 0.000 description 5
KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 5
125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 5
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 5
229920000642 polymer Polymers 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000047 product 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
238000003756 stirring Methods 0.000 description 5
238000000967 suction filtration Methods 0.000 description 5
229910000404 tripotassium phosphate Inorganic materials 0.000 description 5
235000019798 tripotassium phosphate Nutrition 0.000 description 5
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 4
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
125000003545 alkoxy group Chemical group 0.000 description 4
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
125000005013 aryl ether group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
239000004305 biphenyl Substances 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
150000004696 coordination complex Chemical class 0.000 description 4
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