JP6123895B2

JP6123895B2 - 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

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 Download PDF

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Publication number: JP6123895B2
Authority: JP; Japan
Prior art keywords: compound; light emitting; layer; aryl; formula
Prior art date: 2013-07-10
Legal status : Active

Application number

JP2015526409A

Other languages

English (en)

Japanese (ja)

Other versions

JPWO2015005440A1 (ja

Inventor

小野　敦史

敦史小野

俊弘小池

真太朗野村

Current Assignee

JNC Corp

Original Assignee

JNC Corp

Priority date

2013-07-10

Filing date

2014-07-10

Publication date

2017-05-10

2014-07-10 Application filed by JNC Corp filed Critical JNC Corp

2017-03-02 Publication of JPWO2015005440A1 publication Critical patent/JPWO2015005440A1/ja

2017-05-10 Application granted granted Critical

2017-05-10 Publication of JP6123895B2 publication Critical patent/JP6123895B2/ja

Status Active legal-status Critical Current

2034-07-10 Anticipated expiration legal-status Critical

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-1 fluorene compound Chemical class 0.000 title claims description 397
239000000463 material Substances 0.000 title claims description 265
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title description 65
150000001875 compounds Chemical class 0.000 claims description 266
125000003118 aryl group Chemical group 0.000 claims description 159
125000004432 carbon atom Chemical group C* 0.000 claims description 114
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
125000001424 substituent group Chemical group 0.000 claims description 82
239000002019 doping agent Substances 0.000 claims description 65
150000001412 amines Chemical class 0.000 claims description 46
125000003107 substituted aryl group Chemical group 0.000 claims description 41
125000001624 naphthyl group Chemical group 0.000 claims description 31
125000000547 substituted alkyl group Chemical group 0.000 claims description 25
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 24
125000005561 phenanthryl group Chemical group 0.000 claims description 23
HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 22
150000003220 pyrenes Chemical class 0.000 claims description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
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
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 15
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 15
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 13
150000001454 anthracenes Chemical class 0.000 claims description 12
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
150000001846 chrysenes Chemical class 0.000 claims description 9
238000005401 electroluminescence Methods 0.000 claims description 9
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
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
229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 4
150000005041 phenanthrolines Chemical class 0.000 claims description 3
239000010410 layer Substances 0.000 description 390
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 216
125000000217 alkyl group Chemical group 0.000 description 92
230000032258 transport Effects 0.000 description 90
238000002347 injection Methods 0.000 description 73
239000007924 injection Substances 0.000 description 73
125000000753 cycloalkyl group Chemical group 0.000 description 65
238000000034 method Methods 0.000 description 61
239000002904 solvent Substances 0.000 description 55
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 42
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
229910052739 hydrogen Inorganic materials 0.000 description 32
239000001257 hydrogen Substances 0.000 description 32
239000000243 solution Substances 0.000 description 32
239000012299 nitrogen atmosphere Substances 0.000 description 31
238000001308 synthesis method Methods 0.000 description 30
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
238000000746 purification Methods 0.000 description 29
239000000758 substrate Substances 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
239000012043 crude product Substances 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 26
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
229910052782 aluminium Inorganic materials 0.000 description 25
230000005525 hole transport Effects 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 24
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 23
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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
239000007787 solid Substances 0.000 description 21
238000007740 vapor deposition Methods 0.000 description 20
125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 19
239000002994 raw material Substances 0.000 description 19
125000001072 heteroaryl group Chemical group 0.000 description 17
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 17
229910052751 metal Inorganic materials 0.000 description 17
239000002184 metal Substances 0.000 description 17
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
229910052805 deuterium Inorganic materials 0.000 description 16
239000010408 film Substances 0.000 description 16
238000010438 heat treatment Methods 0.000 description 16
150000002431 hydrogen Chemical class 0.000 description 16
238000004519 manufacturing process Methods 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
229910052757 nitrogen Inorganic materials 0.000 description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
238000010992 reflux Methods 0.000 description 15
125000005346 substituted cycloalkyl group Chemical group 0.000 description 15
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
125000003277 amino group Chemical group 0.000 description 13
239000012046 mixed solvent Substances 0.000 description 13
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
229910052799 carbon Inorganic materials 0.000 description 12
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
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 11
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
238000005481 NMR spectroscopy Methods 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
238000000859 sublimation Methods 0.000 description 11
230000008022 sublimation Effects 0.000 description 11
239000000126 substance Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
125000005577 anthracene group Chemical group 0.000 description 9
229910052792 caesium Inorganic materials 0.000 description 9
238000009833 condensation Methods 0.000 description 9
230000005494 condensation Effects 0.000 description 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
239000010409 thin film Substances 0.000 description 9
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 8
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 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
238000000151 deposition Methods 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
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 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
238000001953 recrystallisation 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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
239000007983 Tris buffer Substances 0.000 description 7
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 7
230000004888 barrier function Effects 0.000 description 7
230000008021 deposition Effects 0.000 description 7
150000002739 metals Chemical class 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
125000004076 pyridyl group Chemical group 0.000 description 7
230000006798 recombination Effects 0.000 description 7
238000005215 recombination Methods 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
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 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
239000000047 product Substances 0.000 description 6
125000006413 ring segment Chemical group 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 6
SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical class C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 6
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
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
239000004305 biphenyl Substances 0.000 description 5
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
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 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
239000011259 mixed solution 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
229910052763 palladium Inorganic materials 0.000 description 5
125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 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
229910052700 potassium Inorganic materials 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
125000005581 pyrene group Chemical group 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
125000004178 (C1-C4) 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
238000006069 Suzuki reaction reaction Methods 0.000 description 4
239000002253 acid Substances 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
239000012141 concentrate Substances 0.000 description 4
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000005281 excited state Effects 0.000 description 4
239000007789 gas Substances 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
125000002883 imidazolyl group Chemical group 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
125000003136 n-heptyl 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])* 0.000 description 4
HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 4
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-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
238000010791 quenching Methods 0.000 description 4
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
239000004065 semiconductor Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
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