CN111936504A

CN111936504A - 环烷基取代多环芳香族化合物

环烷基取代多环芳香族化合物 Download PDF

Info

Publication number: CN111936504A
Authority: CN; China
Prior art keywords: group; ring; substituted; carbon atoms; aryl
Prior art date: 2018-04-12
Legal status : Pending

Application number

CN201980024052.3A

Other languages

English (en)

Chinese (zh)

Inventor

畠山琢次

枝连一志

笹田康幸

町田咏希

Current Assignee

Kansai College

SK Materials JNC Co Ltd

Original Assignee

Kansai College

JNC Corp

Priority date

2018-04-12

Filing date

2019-04-09

Publication date

2020-11-13

2019-04-09 Application filed by Kansai College, JNC Corp filed Critical Kansai College

2019-04-09 Priority claimed from PCT/JP2019/015410 external-priority patent/WO2019198699A1/ja

2020-11-13 Publication of CN111936504A publication Critical patent/CN111936504A/zh

Status Pending legal-status Critical Current

Links

-1 polycyclic aromatic compounds Chemical class 0.000 title claims abstract description 502
125000003118 aryl group Chemical group 0.000 claims abstract description 345
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 189
239000000463 material Substances 0.000 claims abstract description 177
229910052796 boron Inorganic materials 0.000 claims abstract description 15
150000001875 compounds Chemical class 0.000 claims description 361
125000004432 carbon atom Chemical group C* 0.000 claims description 324
239000010410 layer Substances 0.000 claims description 308
125000000217 alkyl group Chemical group 0.000 claims description 242
239000000243 solution Substances 0.000 claims description 215
125000001072 heteroaryl group Chemical group 0.000 claims description 176
229920000642 polymer Polymers 0.000 claims description 140
229910052739 hydrogen Inorganic materials 0.000 claims description 135
239000001257 hydrogen Substances 0.000 claims description 135
125000001424 substituent group Chemical group 0.000 claims description 127
239000000203 mixture Substances 0.000 claims description 110
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 87
239000012044 organic layer Substances 0.000 claims description 76
238000002347 injection Methods 0.000 claims description 72
239000007924 injection Substances 0.000 claims description 72
125000003545 alkoxy group Chemical group 0.000 claims description 60
150000002431 hydrogen Chemical class 0.000 claims description 44
125000004986 diarylamino group Chemical group 0.000 claims description 40
230000005525 hole transport Effects 0.000 claims description 34
229910052698 phosphorus Inorganic materials 0.000 claims description 34
125000005647 linker group Chemical group 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
229910052782 aluminium Inorganic materials 0.000 claims description 32
229910052736 halogen Chemical group 0.000 claims description 32
150000002367 halogens Chemical group 0.000 claims description 32
229910052751 metal Inorganic materials 0.000 claims description 32
239000002184 metal Substances 0.000 claims description 32
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 31
229910052799 carbon Inorganic materials 0.000 claims description 31
229920006037 cross link polymer Polymers 0.000 claims description 30
125000004104 aryloxy group Chemical group 0.000 claims description 29
239000003960 organic solvent Substances 0.000 claims description 29
125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 26
239000000178 monomer Substances 0.000 claims description 26
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
229910052805 deuterium Inorganic materials 0.000 claims description 25
229910052717 sulfur Inorganic materials 0.000 claims description 25
125000004093 cyano group Chemical group *C#N 0.000 claims description 24
229910052760 oxygen Inorganic materials 0.000 claims description 24
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
239000010409 thin film Substances 0.000 claims description 23
125000005240 diheteroarylamino group Chemical group 0.000 claims description 22
239000002019 doping agent Substances 0.000 claims description 22
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 21
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 19
229910052783 alkali metal Inorganic materials 0.000 claims description 17
150000001340 alkali metals Chemical class 0.000 claims description 17
125000002619 bicyclic group Chemical group 0.000 claims description 15
238000004132 cross linking Methods 0.000 claims description 15
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 15
125000005577 anthracene group Chemical group 0.000 claims description 14
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 13
150000001342 alkaline earth metals Chemical class 0.000 claims description 13
HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 12
230000005669 field effect Effects 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
150000004820 halides Chemical class 0.000 claims description 12
229910052761 rare earth metal Inorganic materials 0.000 claims description 12
150000002910 rare earth metals Chemical class 0.000 claims description 12
150000001454 anthracenes Chemical class 0.000 claims description 11
230000000379 polymerizing effect Effects 0.000 claims description 11
229910052733 gallium Inorganic materials 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
150000003222 pyridines Chemical class 0.000 claims description 9
229910052785 arsenic Inorganic materials 0.000 claims description 8
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 8
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 8
150000003918 triazines Chemical class 0.000 claims description 8
239000000539 dimer Substances 0.000 claims description 7
150000003230 pyrimidines Chemical class 0.000 claims description 7
229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 6
150000002219 fluoranthenes Chemical class 0.000 claims description 6
239000005267 main chain polymer Substances 0.000 claims description 6
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 6
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 5
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 claims description 4
150000005041 phenanthrolines Chemical class 0.000 claims description 4
229910052727 yttrium Inorganic materials 0.000 claims description 4
150000003384 small molecules Chemical class 0.000 claims description 3
125000000547 substituted alkyl group Chemical group 0.000 claims description 3
239000013638 trimer Substances 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 abstract description 11
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 8
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 117
239000010408 film Substances 0.000 description 104
238000000034 method Methods 0.000 description 98
238000006243 chemical reaction Methods 0.000 description 84
238000005401 electroluminescence Methods 0.000 description 81
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 74
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 68
239000000543 intermediate Substances 0.000 description 65
239000000758 substrate Substances 0.000 description 53
230000015572 biosynthetic process Effects 0.000 description 51
239000000126 substance Substances 0.000 description 43
238000007740 vapor deposition Methods 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 39
239000012043 crude product Substances 0.000 description 38
125000001624 naphthyl group Chemical group 0.000 description 37
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 36
YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 33
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 28
239000013078 crystal Substances 0.000 description 28
238000003786 synthesis reaction Methods 0.000 description 28
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
239000003480 eluent Substances 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 26
238000004519 manufacturing process Methods 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
125000003342 alkenyl group Chemical group 0.000 description 24
MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 description 23
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 23
238000001816 cooling Methods 0.000 description 23
229910052757 nitrogen Inorganic materials 0.000 description 23
239000012299 nitrogen atmosphere Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
239000000741 silica gel Substances 0.000 description 23
239000002904 solvent Substances 0.000 description 23
238000000576 coating method Methods 0.000 description 22
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
235000010290 biphenyl Nutrition 0.000 description 19
238000010438 heat treatment Methods 0.000 description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 description 19
238000003756 stirring Methods 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 18
239000011248 coating agent Substances 0.000 description 18
239000002994 raw material Substances 0.000 description 18
239000004305 biphenyl Substances 0.000 description 17
238000009835 boiling Methods 0.000 description 17
239000011521 glass Substances 0.000 description 17
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 16
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
239000008096 xylene Substances 0.000 description 16
238000000151 deposition Methods 0.000 description 15
230000008021 deposition Effects 0.000 description 15
229910052744 lithium Inorganic materials 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
239000004065 semiconductor Substances 0.000 description 14
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 14
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 13
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 13
229910052763 palladium Inorganic materials 0.000 description 13
125000005561 phenanthryl group Chemical group 0.000 description 13
125000000623 heterocyclic group Chemical group 0.000 description 12
239000004094 surface-active agent Substances 0.000 description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
150000001716 carbazoles Chemical class 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
238000001771 vacuum deposition Methods 0.000 description 11
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
125000003277 amino group Chemical group 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 10
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 10
238000001035 drying Methods 0.000 description 10
239000011159 matrix material Substances 0.000 description 10
229920005989 resin Polymers 0.000 description 10
239000011347 resin Substances 0.000 description 10
238000006467 substitution reaction Methods 0.000 description 10
238000010189 synthetic method Methods 0.000 description 10
125000005580 triphenylene group Chemical group 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
125000001931 aliphatic group Chemical group 0.000 description 9
229910052792 caesium Inorganic materials 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
125000004957 naphthylene group Chemical group 0.000 description 9
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 9
239000007858 starting material Substances 0.000 description 9
239000011593 sulfur Substances 0.000 description 9
125000001544 thienyl group Chemical group 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
239000002841 Lewis acid Substances 0.000 description 8
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
125000000732 arylene group Chemical group 0.000 description 8
125000004429 atom Chemical group 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
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 8
230000020169 heat generation Effects 0.000 description 8
150000007517 lewis acids Chemical class 0.000 description 8
239000001301 oxygen Substances 0.000 description 8
229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
125000001725 pyrenyl group Chemical group 0.000 description 8
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 8
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
239000001632 sodium acetate Substances 0.000 description 8
235000017281 sodium acetate Nutrition 0.000 description 8
238000001308 synthesis method Methods 0.000 description 8
239000003341 Bronsted base Substances 0.000 description 7
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 7
125000005110 aryl thio group Chemical group 0.000 description 7
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
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 7
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 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
125000001041 indolyl group Chemical group 0.000 description 7
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 7
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 7
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 7
238000006116 polymerization reaction Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
125000004076 pyridyl group Chemical group 0.000 description 7
230000001603 reducing effect Effects 0.000 description 7
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 6
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
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 6
150000001491 aromatic compounds Chemical class 0.000 description 6
239000011230 binding agent Substances 0.000 description 6
125000006267 biphenyl group Chemical group 0.000 description 6
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
238000009833 condensation Methods 0.000 description 6
230000005494 condensation Effects 0.000 description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
238000006263 metalation reaction Methods 0.000 description 6
150000002739 metals Chemical class 0.000 description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000002971 oxazolyl group Chemical group 0.000 description 6
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 6
125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
125000000168 pyrrolyl group Chemical group 0.000 description 6
229910052710 silicon Inorganic materials 0.000 description 6
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 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
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 5
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 5
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