JP2021528379A - ヘテロ環化合物、これを含む有機発光素子、有機発光素子の有機物層用組成物および有機発光素子の製造方法 - Google Patents
ヘテロ環化合物、これを含む有機発光素子、有機発光素子の有機物層用組成物および有機発光素子の製造方法 Download PDFInfo
- Publication number
- JP2021528379A JP2021528379A JP2020566741A JP2020566741A JP2021528379A JP 2021528379 A JP2021528379 A JP 2021528379A JP 2020566741 A JP2020566741 A JP 2020566741A JP 2020566741 A JP2020566741 A JP 2020566741A JP 2021528379 A JP2021528379 A JP 2021528379A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- group
- unsubstituted
- light emitting
- chemical formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 84
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 title claims abstract description 23
- 239000011368 organic material Substances 0.000 title claims description 29
- 239000000126 substance Substances 0.000 claims abstract description 166
- 239000010410 layer Substances 0.000 claims description 165
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000003118 aryl group Chemical group 0.000 claims description 74
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 239000012044 organic layer Substances 0.000 claims description 38
- 238000002347 injection Methods 0.000 claims description 26
- 239000007924 injection Substances 0.000 claims description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 230000005525 hole transport Effects 0.000 claims description 13
- 125000002950 monocyclic group Chemical group 0.000 claims description 13
- 150000002430 hydrocarbons Chemical group 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- 125000005580 triphenylene group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000001771 vacuum deposition Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 83
- 239000000463 material Substances 0.000 description 59
- -1 1-methylpentyl group Chemical group 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 34
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 22
- 239000012153 distilled water Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000002019 doping agent Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 16
- 238000000605 extraction Methods 0.000 description 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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
- 229940126062 Compound A Drugs 0.000 description 10
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000006267 biphenyl group Chemical group 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 8
- 0 C*(C(C1*(C)=C(*N)C=C1)=C)=C Chemical compound C*(C(C1*(C)=C(*N)C=C1)=C)=C 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910052741 iridium Inorganic materials 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229920000767 polyaniline Polymers 0.000 description 6
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical group C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- UJCQCUHXXOYHGI-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound ClC1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1.ClC1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 UJCQCUHXXOYHGI-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical group C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 3
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- FZTLLUYFWAOGGB-UHFFFAOYSA-N 1,4-dioxane dioxane Chemical compound C1COCCO1.C1COCCO1 FZTLLUYFWAOGGB-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 2
- IKJUIUCZEXVZMB-UHFFFAOYSA-N 1-bromo-5-chloro-3-fluoro-2-iodobenzene Chemical compound FC1=CC(Cl)=CC(Br)=C1I IKJUIUCZEXVZMB-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- 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 2
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 2
- GKTLHQFSIDFAJH-UHFFFAOYSA-N 3-(9h-carbazol-3-yl)-9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=C4C5=CC=CC=C5NC4=CC=3)C=C2C2=CC=CC=C21 GKTLHQFSIDFAJH-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- IAWRFMPNMXEJCK-UHFFFAOYSA-N 3-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=C(NC=2C3=CC=CC=2)C3=C1 IAWRFMPNMXEJCK-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 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 2
- 238000000427 thin-film deposition Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-N 0.000 description 1
- DSQMLISBVUTWJB-UHFFFAOYSA-N 2,6-diphenylaniline Chemical group NC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 DSQMLISBVUTWJB-UHFFFAOYSA-N 0.000 description 1
- BMNNKTUDZBYENZ-UHFFFAOYSA-N 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenethiol Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=C1S BMNNKTUDZBYENZ-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 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 1
- KAJMDIRNTNSOLE-UHFFFAOYSA-N 2-naphthalen-1-yl-1,3-benzoxazole Chemical compound C1=CC=C2C(C=3OC4=CC=CC=C4N=3)=CC=CC2=C1 KAJMDIRNTNSOLE-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SHBHYINHXNTBRP-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-methylsulfonylethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCS(=O)(=O)C)C=CC=1 SHBHYINHXNTBRP-UHFFFAOYSA-N 0.000 description 1
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- VJHVLELNDFVKMS-UHFFFAOYSA-N 3-methoxy-2-phenylpyridine Chemical compound COC1=CC=CN=C1C1=CC=CC=C1 VJHVLELNDFVKMS-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical group C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 1
- KCOYLRXCNKJSSC-UHFFFAOYSA-N 9h-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 KCOYLRXCNKJSSC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CAZACVILDVQAOE-AYMJVOPVSA-N C(C(C=C1)c2nc(C3=CC4Sc5ccccc5[C@@H]4C(c4ccccc4)=C3)nc(-c3ccccc3)n2)C=C1c1ccccc1 Chemical compound C(C(C=C1)c2nc(C3=CC4Sc5ccccc5[C@@H]4C(c4ccccc4)=C3)nc(-c3ccccc3)n2)C=C1c1ccccc1 CAZACVILDVQAOE-AYMJVOPVSA-N 0.000 description 1
- WAHRNZUKNHUXDZ-UHFFFAOYSA-N C(C(Cc1c2c3ccccc3[s]1)C(C=C1)=CCC1c1ccccc1)C2c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound C(C(Cc1c2c3ccccc3[s]1)C(C=C1)=CCC1c1ccccc1)C2c1nc(-c2ccccc2)nc(-c2ccccc2)n1 WAHRNZUKNHUXDZ-UHFFFAOYSA-N 0.000 description 1
- DCXMGVUHFVMYDO-UHFFFAOYSA-N C(C1)C=C(C2N=C(c3cc(-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)cc4c3c(cccc3)c3[s]4)N=C(C3C=CC=CC3)N2)c2c1c(cccc1)c1[s]2 Chemical compound C(C1)C=C(C2N=C(c3cc(-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)cc4c3c(cccc3)c3[s]4)N=C(C3C=CC=CC3)N2)c2c1c(cccc1)c1[s]2 DCXMGVUHFVMYDO-UHFFFAOYSA-N 0.000 description 1
- RUZJDRQZPRGGLO-UHFFFAOYSA-N C(C1)C=C(C=CC=C2)C2=C1c1cccc(C2=CC3Sc4ccccc4C3C(C3N=C(c4ccccc4)N=C(c4ccccc4)[N-]3)=C2)c1 Chemical compound C(C1)C=C(C=CC=C2)C2=C1c1cccc(C2=CC3Sc4ccccc4C3C(C3N=C(c4ccccc4)N=C(c4ccccc4)[N-]3)=C2)c1 RUZJDRQZPRGGLO-UHFFFAOYSA-N 0.000 description 1
- DAJGJDAIKLHBMT-UHFFFAOYSA-N C(C1)C=CC=C1C1=CCCC(C2=CC(c3cc(-c4nc(-c5ccccc5)nc(-c5ccccc5)n4)c(c4ccccc4[s]4)c4c3)=CCC2)=C1 Chemical compound C(C1)C=CC=C1C1=CCCC(C2=CC(c3cc(-c4nc(-c5ccccc5)nc(-c5ccccc5)n4)c(c4ccccc4[s]4)c4c3)=CCC2)=C1 DAJGJDAIKLHBMT-UHFFFAOYSA-N 0.000 description 1
- DKHMLQJAIISKGE-UHFFFAOYSA-N C(C1)C=CC=C1C1=NC(c2ccccc2)=NC(C(CC([n]2c3ccccc3c(C=C3)c2CC3c2ccccc2)=C2)c3c2[s]c2ccccc32)[N-]1 Chemical compound C(C1)C=CC=C1C1=NC(c2ccccc2)=NC(C(CC([n]2c3ccccc3c(C=C3)c2CC3c2ccccc2)=C2)c3c2[s]c2ccccc32)[N-]1 DKHMLQJAIISKGE-UHFFFAOYSA-N 0.000 description 1
- XQGKKVAZLRFWAP-UHFFFAOYSA-N C(C1)C=CC=C1C1N=C(c2ccc(c3ccccc3[o]3)c3c2)N=C(c2cc(-[n]3c(ccc(-c(cc4)cc5c4[s]c4c5cccc4)c4)c4c4ccccc34)c(c3ccccc3[s]3)c3c2)[N-]1 Chemical compound C(C1)C=CC=C1C1N=C(c2ccc(c3ccccc3[o]3)c3c2)N=C(c2cc(-[n]3c(ccc(-c(cc4)cc5c4[s]c4c5cccc4)c4)c4c4ccccc34)c(c3ccccc3[s]3)c3c2)[N-]1 XQGKKVAZLRFWAP-UHFFFAOYSA-N 0.000 description 1
- BXEZZPABMBJZEK-UHFFFAOYSA-N C(C1)C=CC=C1C1[N-]C(c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c3ccccc3[o]3)c3c2)=Nc2c1[s]c1c2cccc1 Chemical compound C(C1)C=CC=C1C1[N-]C(c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c3ccccc3[o]3)c3c2)=Nc2c1[s]c1c2cccc1 BXEZZPABMBJZEK-UHFFFAOYSA-N 0.000 description 1
- MRECPGVMYNENFI-UHFFFAOYSA-N C(C1)C=CC=C1[Si](c1ccccc1)(c1ccccc1)c1cccc(C(C=C(C23)c4nc(-c5ccccc5)nc(-c5ccccc5)n4)=CC2Sc2c3cccc2)c1 Chemical compound C(C1)C=CC=C1[Si](c1ccccc1)(c1ccccc1)c1cccc(C(C=C(C23)c4nc(-c5ccccc5)nc(-c5ccccc5)n4)=CC2Sc2c3cccc2)c1 MRECPGVMYNENFI-UHFFFAOYSA-N 0.000 description 1
- RQLQCWDCYCPTSR-UHFFFAOYSA-N C(C1)C=CC=C1c(cc1)cc(C2C=CC=CC22)c1N2c1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c(c2ccccc2[s]2)c2c1 Chemical compound C(C1)C=CC=C1c(cc1)cc(C2C=CC=CC22)c1N2c1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c(c2ccccc2[s]2)c2c1 RQLQCWDCYCPTSR-UHFFFAOYSA-N 0.000 description 1
- ISMHXQPJEACOQN-UHFFFAOYSA-N C(C1)C=CC=C1c1c(C2=CC=CCC2S2)c2cc(-c2nc(C3=CC=CCC3)nc(-c3cc(-c4ccccc4)ccc3)n2)c1 Chemical compound C(C1)C=CC=C1c1c(C2=CC=CCC2S2)c2cc(-c2nc(C3=CC=CCC3)nc(-c3cc(-c4ccccc4)ccc3)n2)c1 ISMHXQPJEACOQN-UHFFFAOYSA-N 0.000 description 1
- AMUWECLNVMALRE-UHFFFAOYSA-N C(C1)C=CC=C1c1cc(-c2cc(C3NC(c4ccccc4)N=C(c4ccccc4)NC3)c(c3ccccc3[o]3)c3c2)nc(-c2ccccc2)c1 Chemical compound C(C1)C=CC=C1c1cc(-c2cc(C3NC(c4ccccc4)N=C(c4ccccc4)NC3)c(c3ccccc3[o]3)c3c2)nc(-c2ccccc2)c1 AMUWECLNVMALRE-UHFFFAOYSA-N 0.000 description 1
- TYQBFBLSOJEBJU-UHFFFAOYSA-N C(C1)C=Cc(c(cc2)c3c4c2c(cccc2)c2[n]4-c2cc(C4=NC(c(cc5)cc6c5c(cccc5)c5[s]6)[N-]C(c5ccccc5)=N4)cc4c2c2ccccc2[s]4)c1[n]3-c1ccccc1 Chemical compound C(C1)C=Cc(c(cc2)c3c4c2c(cccc2)c2[n]4-c2cc(C4=NC(c(cc5)cc6c5c(cccc5)c5[s]6)[N-]C(c5ccccc5)=N4)cc4c2c2ccccc2[s]4)c1[n]3-c1ccccc1 TYQBFBLSOJEBJU-UHFFFAOYSA-N 0.000 description 1
- QDFNEPNSRCJQKG-UHFFFAOYSA-N C(C1)CC=CC1c1nc(C2=CCCC=C2)nc(-c2c(c(cccc3)c3[s]3)c3cc(-c(cccc3)c3-c3ccccc3-c3ccccc3)c2)n1 Chemical compound C(C1)CC=CC1c1nc(C2=CCCC=C2)nc(-c2c(c(cccc3)c3[s]3)c3cc(-c(cccc3)c3-c3ccccc3-c3ccccc3)c2)n1 QDFNEPNSRCJQKG-UHFFFAOYSA-N 0.000 description 1
- WKGDGTFEFVLNHD-UHFFFAOYSA-N C(C1)CC=CC1c1nc(C2=CCCC=C2)nc(-c2c(c3ccccc3[s]3)c3cc(-c(cccc3)c3-c3ccccc3)c2)n1 Chemical compound C(C1)CC=CC1c1nc(C2=CCCC=C2)nc(-c2c(c3ccccc3[s]3)c3cc(-c(cccc3)c3-c3ccccc3)c2)n1 WKGDGTFEFVLNHD-UHFFFAOYSA-N 0.000 description 1
- BOZFPJZKTYJKDL-UHFFFAOYSA-N C(C1)CC=CC1c1nc(C2=CCCC=C2)nc(C(CC(c2ccccc2)=C2)c3c2[s]c2ccccc32)n1 Chemical compound C(C1)CC=CC1c1nc(C2=CCCC=C2)nc(C(CC(c2ccccc2)=C2)c3c2[s]c2ccccc32)n1 BOZFPJZKTYJKDL-UHFFFAOYSA-N 0.000 description 1
- VNHZPQFJQLIUDH-UHFFFAOYSA-N C(C1)CC=CC1c1nc(C2C=CC=CC2)nc(-c2cc(-c3nc(-c4ccccc4)cc(-c4ccccc4)n3)c(c3ccccc3[o]3)c3c2)n1 Chemical compound C(C1)CC=CC1c1nc(C2C=CC=CC2)nc(-c2cc(-c3nc(-c4ccccc4)cc(-c4ccccc4)n3)c(c3ccccc3[o]3)c3c2)n1 VNHZPQFJQLIUDH-UHFFFAOYSA-N 0.000 description 1
- NZCIWKKRQDKPDF-UHFFFAOYSA-N C(C1Sc2ccccc2C1C(C1=NC(c2ccccc2)=NC(c2ccccc2)N1)=C1)=C1c1cc([Si](c2ccccc2)(c2ccccc2)c2ccccc2)ccc1 Chemical compound C(C1Sc2ccccc2C1C(C1=NC(c2ccccc2)=NC(c2ccccc2)N1)=C1)=C1c1cc([Si](c2ccccc2)(c2ccccc2)c2ccccc2)ccc1 NZCIWKKRQDKPDF-UHFFFAOYSA-N 0.000 description 1
- KYMIBLMCODSGHV-UHFFFAOYSA-N C(C1Sc2ccccc2C1C(C1N=C(c2ccccc2)N=C(c2ccccc2)[N-]1)=C1)=C1[n]1c(ccc(-c(cc2)cc3c2[s]c2ccccc32)c2)c2c2c1cccc2 Chemical compound C(C1Sc2ccccc2C1C(C1N=C(c2ccccc2)N=C(c2ccccc2)[N-]1)=C1)=C1[n]1c(ccc(-c(cc2)cc3c2[s]c2ccccc32)c2)c2c2c1cccc2 KYMIBLMCODSGHV-UHFFFAOYSA-N 0.000 description 1
- PGHUIAUPWSBCRB-UHFFFAOYSA-N C(C1Sc2ccccc2C1C(C1N=C(c2ccccc2)N=C(c2ccccc2)[N-]1)=C1)=C1[n]1c2ccccc2c2c1cccc2 Chemical compound C(C1Sc2ccccc2C1C(C1N=C(c2ccccc2)N=C(c2ccccc2)[N-]1)=C1)=C1[n]1c2ccccc2c2c1cccc2 PGHUIAUPWSBCRB-UHFFFAOYSA-N 0.000 description 1
- HTBIESMLIPFFQQ-UHFFFAOYSA-N C(C1Sc2ccccc2C1C(c1nc(-c2ccccc2)nc(-c2ccccc2)n1)=C1)=C1[n]1c(ccc(-c(cc2)cc3c2[o]c2ccccc32)c2)c2c2ccccc12 Chemical compound C(C1Sc2ccccc2C1C(c1nc(-c2ccccc2)nc(-c2ccccc2)n1)=C1)=C1[n]1c(ccc(-c(cc2)cc3c2[o]c2ccccc32)c2)c2c2ccccc12 HTBIESMLIPFFQQ-UHFFFAOYSA-N 0.000 description 1
- UAQKDBSYPAPVRS-UHFFFAOYSA-N C(C1Sc2ccccc2C1C(c1nc(-c2ccccc2)nc(-c2ccccc2)n1)=C1)=C1c(cc1)cc2c1c(cccc1)c1c1c2cccc1 Chemical compound C(C1Sc2ccccc2C1C(c1nc(-c2ccccc2)nc(-c2ccccc2)n1)=C1)=C1c(cc1)cc2c1c(cccc1)c1c1c2cccc1 UAQKDBSYPAPVRS-UHFFFAOYSA-N 0.000 description 1
- LJIRIFYELFYYOA-UHFFFAOYSA-N C(C1Sc2ccccc2C1C(c1nc(-c2ccccc2)nc(-c2ccccc2)n1)=C1)=C1c1cc(P(c2ccccc2)c2ccccc2)ccc1 Chemical compound C(C1Sc2ccccc2C1C(c1nc(-c2ccccc2)nc(-c2ccccc2)n1)=C1)=C1c1cc(P(c2ccccc2)c2ccccc2)ccc1 LJIRIFYELFYYOA-UHFFFAOYSA-N 0.000 description 1
- RPZUORRFDHSMIZ-UHFFFAOYSA-N C(C1c2ccccc22)=CC(c3ccccc3)=CC1N2C1=CC(c2nc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2)=CC2Sc3ccccc3C12 Chemical compound C(C1c2ccccc22)=CC(c3ccccc3)=CC1N2C1=CC(c2nc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)ccc2)=CC2Sc3ccccc3C12 RPZUORRFDHSMIZ-UHFFFAOYSA-N 0.000 description 1
- TXDMMGHSZDZDFQ-UHFFFAOYSA-N C(C1c2nc(-c3ccccc3)nc(-c3ccccc3)n2)C(c(cccc2)c2-c2ccccc2-c(cc2)cc3c2c2ccccc2c2c3cccc2)=Cc2c1c1ccccc1[s]2 Chemical compound C(C1c2nc(-c3ccccc3)nc(-c3ccccc3)n2)C(c(cccc2)c2-c2ccccc2-c(cc2)cc3c2c2ccccc2c2c3cccc2)=Cc2c1c1ccccc1[s]2 TXDMMGHSZDZDFQ-UHFFFAOYSA-N 0.000 description 1
- NKROKOHECVRRNJ-UHFFFAOYSA-N C(CC(c1ccccc1)=CC1c2ccccc22)C1N2C1=CC2Sc3ccccc3C2C(c2nc(-c3ccccc3)nc(-c3ccccc3)n2)=C1 Chemical compound C(CC(c1ccccc1)=CC1c2ccccc22)C1N2C1=CC2Sc3ccccc3C2C(c2nc(-c3ccccc3)nc(-c3ccccc3)n2)=C1 NKROKOHECVRRNJ-UHFFFAOYSA-N 0.000 description 1
- CDIUNAXWLDSZNW-UHFFFAOYSA-N C(CC1)CC=C1c1nc(C(CC(c2cc(-c3cc(-c4ccccc4)cc(-c4ccccc4)c3)ccc2)=C2)c3c2[s]c2c3cccc2)nc(C2=CCCC=C2)n1 Chemical compound C(CC1)CC=C1c1nc(C(CC(c2cc(-c3cc(-c4ccccc4)cc(-c4ccccc4)c3)ccc2)=C2)c3c2[s]c2c3cccc2)nc(C2=CCCC=C2)n1 CDIUNAXWLDSZNW-UHFFFAOYSA-N 0.000 description 1
- FLLVPBVLENSYPQ-UHFFFAOYSA-N C(CC1c2cc(cccc3)c3c3c2cccc3)CC=C1C1=CC2Sc3ccccc3C2C(c2nc(C3C=CC=CC3)cc(C3=CCCC=C3)n2)=C1 Chemical compound C(CC1c2cc(cccc3)c3c3c2cccc3)CC=C1C1=CC2Sc3ccccc3C2C(c2nc(C3C=CC=CC3)cc(C3=CCCC=C3)n2)=C1 FLLVPBVLENSYPQ-UHFFFAOYSA-N 0.000 description 1
- FORQAILJKITBOU-UHFFFAOYSA-N C(CC=CC1)C1c1nc(-c2cc(-[n]3c(ccc(-c(cc4)cc5c4[n](C4C=CC=CC4)c4c5cccc4)c4)c4c4ccccc34)c(c3ccccc3[s]3)c3c2)nc(-c2cccc3c2[s]c2c3cccc2)n1 Chemical compound C(CC=CC1)C1c1nc(-c2cc(-[n]3c(ccc(-c(cc4)cc5c4[n](C4C=CC=CC4)c4c5cccc4)c4)c4c4ccccc34)c(c3ccccc3[s]3)c3c2)nc(-c2cccc3c2[s]c2c3cccc2)n1 FORQAILJKITBOU-UHFFFAOYSA-N 0.000 description 1
- LVFQVODDMZSWNX-UHFFFAOYSA-N C(CC=CC1c(cc2)c3c4c2c(cccc2)c2[n]4-c2cc(-c4nc(-c5ccccc5)nc(C5=CCCC=C5)n4)c(c4ccccc4[s]4)c4c2)C1N3c1ccccc1 Chemical compound C(CC=CC1c(cc2)c3c4c2c(cccc2)c2[n]4-c2cc(-c4nc(-c5ccccc5)nc(C5=CCCC=C5)n4)c(c4ccccc4[s]4)c4c2)C1N3c1ccccc1 LVFQVODDMZSWNX-UHFFFAOYSA-N 0.000 description 1
- CMEAMERHRZGDFY-UHFFFAOYSA-N C(Cc1c2)C=Cc1ccc2-c1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c(c2ccccc2[s]2)c2c1 Chemical compound C(Cc1c2)C=Cc1ccc2-c1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c(c2ccccc2[s]2)c2c1 CMEAMERHRZGDFY-UHFFFAOYSA-N 0.000 description 1
- RHDSRDDWPGMTPN-UHFFFAOYSA-N C(Cc1c2[s]c3c1cccc3)C=C2C1=NC(C2C=CC=CC2)=NC(C(CC(c(cc2)cc3c2c(cccc2)c2c2c3cccc2)=C2)c3c2[s]c2c3cccc2)N1 Chemical compound C(Cc1c2[s]c3c1cccc3)C=C2C1=NC(C2C=CC=CC2)=NC(C(CC(c(cc2)cc3c2c(cccc2)c2c2c3cccc2)=C2)c3c2[s]c2c3cccc2)N1 RHDSRDDWPGMTPN-UHFFFAOYSA-N 0.000 description 1
- XHDZSTNCNPSKHX-KDJFERLWSA-N C/C(/c1nc(-c2cccc(-c3ccccc3)c2)nc(C2=CCCC(C3=CC=CCC3)=C2)n1)=C\c1c(C(c2ccccc2)N)c2ccccc2[s]1 Chemical compound C/C(/c1nc(-c2cccc(-c3ccccc3)c2)nc(C2=CCCC(C3=CC=CCC3)=C2)n1)=C\c1c(C(c2ccccc2)N)c2ccccc2[s]1 XHDZSTNCNPSKHX-KDJFERLWSA-N 0.000 description 1
- IVZWBEQEZRQIRU-UHFFFAOYSA-N C1(=CC=CC=C1)C=1C=CC=2NC3=CC=CC=C3C2C1.C1(=CC=CC=C1)C=1C=CC=2NC3=CC=CC=C3C2C1 Chemical compound C1(=CC=CC=C1)C=1C=CC=2NC3=CC=CC=C3C2C1.C1(=CC=CC=C1)C=1C=CC=2NC3=CC=CC=C3C2C1 IVZWBEQEZRQIRU-UHFFFAOYSA-N 0.000 description 1
- YUIVYVFBRORXIO-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2 Chemical group C1(=CC=CC=C1)NC1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2 YUIVYVFBRORXIO-UHFFFAOYSA-N 0.000 description 1
- IUOLIAZBHXKGQF-UHFFFAOYSA-N C1C(c(cc2)cc(C3C=CC=CC33)c2N3c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c3ccccc3[s]3)c3c2)=CC=C2Oc3ccccc3C12 Chemical compound C1C(c(cc2)cc(C3C=CC=CC33)c2N3c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c3ccccc3[s]3)c3c2)=CC=C2Oc3ccccc3C12 IUOLIAZBHXKGQF-UHFFFAOYSA-N 0.000 description 1
- WZHKAFKOOHLWBZ-UHFFFAOYSA-N C1C(c(cc2)cc(c3ccccc33)c2[n]3C2=CC3Sc4ccccc4C3C(c3nc(-c4ccccc4)nc(-c4ccccc4)n3)=C2)=CC=C2Sc3ccccc3C12 Chemical compound C1C(c(cc2)cc(c3ccccc33)c2[n]3C2=CC3Sc4ccccc4C3C(c3nc(-c4ccccc4)nc(-c4ccccc4)n3)=C2)=CC=C2Sc3ccccc3C12 WZHKAFKOOHLWBZ-UHFFFAOYSA-N 0.000 description 1
- RMGHTBFLCWZPMB-UHFFFAOYSA-N C1C(c2ccccc2)=NC(c2ccccc2)=NC1c1cccc(-c2cc(-c3cccc(-c4nc(-c5ccccc5)nc(-c5ccccc5)n4)c3)c(c3ccccc3[o]3)c3c2)c1 Chemical compound C1C(c2ccccc2)=NC(c2ccccc2)=NC1c1cccc(-c2cc(-c3cccc(-c4nc(-c5ccccc5)nc(-c5ccccc5)n4)c3)c(c3ccccc3[o]3)c3c2)c1 RMGHTBFLCWZPMB-UHFFFAOYSA-N 0.000 description 1
- NCYGNXZFPCTHNU-UHFFFAOYSA-N C1C2C(CCC=C3)=C3c3cc(-c(cccc4)c4C4=CC5Sc6ccccc6C5C(c5nc(C6C=CC=CC6)nc(C6=CCCC=C6)n5)=C4)ccc3C2C=CC1 Chemical compound C1C2C(CCC=C3)=C3c3cc(-c(cccc4)c4C4=CC5Sc6ccccc6C5C(c5nc(C6C=CC=CC6)nc(C6=CCCC=C6)n5)=C4)ccc3C2C=CC1 NCYGNXZFPCTHNU-UHFFFAOYSA-N 0.000 description 1
- JJIUVCJHKWMRAZ-UHFFFAOYSA-N C1C=C2Sc3ccccc3C2=CC1c1nc(-c2cc([s]c3c4cccc3)c4c(-[n](c3c4cccc3)c(cc3)c4c(c4ccccc44)c3[n]4-c3ccccc3)c2)nc(-c2ccccc2)n1 Chemical compound C1C=C2Sc3ccccc3C2=CC1c1nc(-c2cc([s]c3c4cccc3)c4c(-[n](c3c4cccc3)c(cc3)c4c(c4ccccc44)c3[n]4-c3ccccc3)c2)nc(-c2ccccc2)n1 JJIUVCJHKWMRAZ-UHFFFAOYSA-N 0.000 description 1
- REIZCNPNRNHJHW-UHFFFAOYSA-N C1C=CC(C2=NC(C3C=CC=CC3)=NC(c3c(c4ccccc4[s]4)c4cc(-c(cc4)ccc4-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)c3)[N-]2)=CC1 Chemical compound C1C=CC(C2=NC(C3C=CC=CC3)=NC(c3c(c4ccccc4[s]4)c4cc(-c(cc4)ccc4-c4cc5c(cccc6)c6c(cccc6)c6c5cc4)c3)[N-]2)=CC1 REIZCNPNRNHJHW-UHFFFAOYSA-N 0.000 description 1
- BJBWZDNSDBFSJH-UHFFFAOYSA-N C1C=CC(C2=NC(c3ccccc3)NC(c3c(c4ccccc4[s]4)c4cc(-c(cc4)ccc4-c(cc4)ccc4-c4cc(-c5ccccc5C5C=CC=CC55)c5cc4)c3)=N2)=CC1 Chemical compound C1C=CC(C2=NC(c3ccccc3)NC(c3c(c4ccccc4[s]4)c4cc(-c(cc4)ccc4-c(cc4)ccc4-c4cc(-c5ccccc5C5C=CC=CC55)c5cc4)c3)=N2)=CC1 BJBWZDNSDBFSJH-UHFFFAOYSA-N 0.000 description 1
- WVXIWTMEBFDESC-UHFFFAOYSA-N C1C=CC(C2N=C(c3ccccc3)N=C(c3c(c4ccccc4[s]4)c4cc([SiH-](c4ccccc4)(c4ccccc4)c4ccccc4)c3)N2)=CC1 Chemical compound C1C=CC(C2N=C(c3ccccc3)N=C(c3c(c4ccccc4[s]4)c4cc([SiH-](c4ccccc4)(c4ccccc4)c4ccccc4)c3)N2)=CC1 WVXIWTMEBFDESC-UHFFFAOYSA-N 0.000 description 1
- IANJOVVQBRQEES-UHFFFAOYSA-N C1C=CC(c2cccc(c3c4cccc3)c2[n]4C2=CC3Sc4ccccc4C3C(c3nc(C4C=CC=CC4)nc(-c4ccccc4)n3)=C2)=CC1 Chemical compound C1C=CC(c2cccc(c3c4cccc3)c2[n]4C2=CC3Sc4ccccc4C3C(c3nc(C4C=CC=CC4)nc(-c4ccccc4)n3)=C2)=CC1 IANJOVVQBRQEES-UHFFFAOYSA-N 0.000 description 1
- SSQFUCKMMSMXNE-UHFFFAOYSA-N C1C=CC(c2nc(-c3c(c4ccccc4[s]4)c4cc(-[n](c4c5cccc4)c4c5c(-c5ccccc5)ccc4)c3)nc(C3C=CC=CC3)n2)=CC1 Chemical compound C1C=CC(c2nc(-c3c(c4ccccc4[s]4)c4cc(-[n](c4c5cccc4)c4c5c(-c5ccccc5)ccc4)c3)nc(C3C=CC=CC3)n2)=CC1 SSQFUCKMMSMXNE-UHFFFAOYSA-N 0.000 description 1
- OITJIKKWLBTEJE-UHFFFAOYSA-N C1C=CC(c2nc(-c3c(c4ccccc4[s]4)c4cc(-c4cccc(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)c3)nc(C3C=CC=CC3)n2)=CC1 Chemical compound C1C=CC(c2nc(-c3c(c4ccccc4[s]4)c4cc(-c4cccc(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)c3)nc(C3C=CC=CC3)n2)=CC1 OITJIKKWLBTEJE-UHFFFAOYSA-N 0.000 description 1
- ROIOUAMCRXQQRV-UHFFFAOYSA-N C1C=CC(c2nc(-c3cccc4c3CCC=C4c3cc(-[n]4c5ccccc5c5ccccc45)c(c4ccccc4[s]4)c4c3)nc(-c3ccccc3)n2)=CC1 Chemical compound C1C=CC(c2nc(-c3cccc4c3CCC=C4c3cc(-[n]4c5ccccc5c5ccccc45)c(c4ccccc4[s]4)c4c3)nc(-c3ccccc3)n2)=CC1 ROIOUAMCRXQQRV-UHFFFAOYSA-N 0.000 description 1
- FMHNUGJGAFHHLL-UHFFFAOYSA-N C1C=CC(c2nc(-c3ccccc3)nc(-c3c(c4ccccc4[s]4)c4cc(-c4cccc(-c5cc(-c6ccccc6)cc(-c6ccccc6)c5)c4)c3)n2)=CC1 Chemical compound C1C=CC(c2nc(-c3ccccc3)nc(-c3c(c4ccccc4[s]4)c4cc(-c4cccc(-c5cc(-c6ccccc6)cc(-c6ccccc6)c5)c4)c3)n2)=CC1 FMHNUGJGAFHHLL-UHFFFAOYSA-N 0.000 description 1
- HTGYDTXGPKWHHA-UHFFFAOYSA-N C1C=CC(c2nc(C3=CC([n](c4ccccc44)c5c4c(-c4ccccc4)ccc5)=CC4Sc5ccccc5C34)nc(C3C=CC=CC3)n2)=CC1 Chemical compound C1C=CC(c2nc(C3=CC([n](c4ccccc44)c5c4c(-c4ccccc4)ccc5)=CC4Sc5ccccc5C34)nc(C3C=CC=CC3)n2)=CC1 HTGYDTXGPKWHHA-UHFFFAOYSA-N 0.000 description 1
- ZCBDZZQASXOMHD-UHFFFAOYSA-N C1C=CC=CC1c1nc(-c2cccc3c2c(cccc2)c2[s]3)nc(C(CC2[n]3c4ccc(c5ccccc5[o]5)c5c4c4c3cccc4)=Cc3c2c2ccccc2[s]3)n1 Chemical compound C1C=CC=CC1c1nc(-c2cccc3c2c(cccc2)c2[s]3)nc(C(CC2[n]3c4ccc(c5ccccc5[o]5)c5c4c4c3cccc4)=Cc3c2c2ccccc2[s]3)n1 ZCBDZZQASXOMHD-UHFFFAOYSA-N 0.000 description 1
- KCGGNFYGABONTO-UHFFFAOYSA-N C1C=CC=CC1c1nc(-c2ccccc2)nc(-c2c(c3ccccc3[o]3)c3cc(-c3nc(-c4ccccc4)cc(-c4ccccc4)n3)c2)n1 Chemical compound C1C=CC=CC1c1nc(-c2ccccc2)nc(-c2c(c3ccccc3[o]3)c3cc(-c3nc(-c4ccccc4)cc(-c4ccccc4)n3)c2)n1 KCGGNFYGABONTO-UHFFFAOYSA-N 0.000 description 1
- NNEKSALJRODZTC-UHFFFAOYSA-N C1C=CC=CC1c1nc(-c2ccccc2)nc(-c2c(c3ccccc3[o]3)c3cc(C(C3)=CC=CC3c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c2)n1 Chemical compound C1C=CC=CC1c1nc(-c2ccccc2)nc(-c2c(c3ccccc3[o]3)c3cc(C(C3)=CC=CC3c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c2)n1 NNEKSALJRODZTC-UHFFFAOYSA-N 0.000 description 1
- LXFUAZOOACRQGD-UHFFFAOYSA-N C1C=CC=CC1c1nc(-c2ccccc2)nc(-c2c(c3ccccc3[s]3)c3cc(-c3cc(-c4cc(cccc5)c5c5ccccc45)ccc3)c2)n1 Chemical compound C1C=CC=CC1c1nc(-c2ccccc2)nc(-c2c(c3ccccc3[s]3)c3cc(-c3cc(-c4cc(cccc5)c5c5ccccc45)ccc3)c2)n1 LXFUAZOOACRQGD-UHFFFAOYSA-N 0.000 description 1
- YHHGSEPPYGEYFZ-UHFFFAOYSA-N C1C=CC=CC1c1nc(-c2ccccc2)nc(C2=CC(C(c3ccccc3)(c3ccccc3)c3ccccc3)=CC3Sc4ccccc4C23)n1 Chemical compound C1C=CC=CC1c1nc(-c2ccccc2)nc(C2=CC(C(c3ccccc3)(c3ccccc3)c3ccccc3)=CC3Sc4ccccc4C23)n1 YHHGSEPPYGEYFZ-UHFFFAOYSA-N 0.000 description 1
- GXVNROAEXBYUIO-UHFFFAOYSA-N C1C=CC=CC1c1nc(-c2ccccc2)nc(C2=CC(c3nc(cccc4)c4[n]3-c3ccccc3)=CC3Oc4ccccc4C23)n1 Chemical compound C1C=CC=CC1c1nc(-c2ccccc2)nc(C2=CC(c3nc(cccc4)c4[n]3-c3ccccc3)=CC3Oc4ccccc4C23)n1 GXVNROAEXBYUIO-UHFFFAOYSA-N 0.000 description 1
- BGQKARWNTIWHRE-CNKIZMDQSA-N C=C1C(C2=C[C@@H]3Oc4ccccc4C3C(c3nc(-c4ccccc4)nc(-c4ccccc4)n3)=C2)=CC=CC1c1nc2ccccc2[n]1-c1ccccc1 Chemical compound C=C1C(C2=C[C@@H]3Oc4ccccc4C3C(c3nc(-c4ccccc4)nc(-c4ccccc4)n3)=C2)=CC=CC1c1nc2ccccc2[n]1-c1ccccc1 BGQKARWNTIWHRE-CNKIZMDQSA-N 0.000 description 1
- LHINHDKXCSJUJO-UHFFFAOYSA-N CC(C)(C1C2)c(cccc3)c3C1=CC=C2C1=NC(c2ccccc2)NC(c2cc([s]c3ccccc33)c3c(-[n]3c(cccc4)c4c(C=CC45)c3C4c3ccccc3N5c3ccccc3)c2)=N1 Chemical compound CC(C)(C1C2)c(cccc3)c3C1=CC=C2C1=NC(c2ccccc2)NC(c2cc([s]c3ccccc33)c3c(-[n]3c(cccc4)c4c(C=CC45)c3C4c3ccccc3N5c3ccccc3)c2)=N1 LHINHDKXCSJUJO-UHFFFAOYSA-N 0.000 description 1
- ZWFUUVHWITTXGU-UHFFFAOYSA-N CC(C1(C)N=C(c2ccccc2)N=C(c2ccccc2)N1)(C([n]1c(c(C2=CCCC=C2)ccc2)c2c2ccccc12)=C1)c2c1[s]c1c2cccc1 Chemical compound CC(C1(C)N=C(c2ccccc2)N=C(c2ccccc2)N1)(C([n]1c(c(C2=CCCC=C2)ccc2)c2c2ccccc12)=C1)c2c1[s]c1c2cccc1 ZWFUUVHWITTXGU-UHFFFAOYSA-N 0.000 description 1
- BKZCSPUZGCCQOE-UHFFFAOYSA-N CC(C1=CC([n]2c3ccccc3c3c2cccc3)=CC2Sc3ccccc3C12)/N=C(/C1=CCCC=C1)\N=C(\c1ccccc1)/N Chemical compound CC(C1=CC([n]2c3ccccc3c3c2cccc3)=CC2Sc3ccccc3C12)/N=C(/C1=CCCC=C1)\N=C(\c1ccccc1)/N BKZCSPUZGCCQOE-UHFFFAOYSA-N 0.000 description 1
- INUSZOVDKFIGJD-UHFFFAOYSA-N CC(C1C=CC=C2)C2N(c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c3ccccc3[s]3)c3c2)c2c1ccc1c2[s]c2ccccc12 Chemical compound CC(C1C=CC=C2)C2N(c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c3ccccc3[s]3)c3c2)c2c1ccc1c2[s]c2ccccc12 INUSZOVDKFIGJD-UHFFFAOYSA-N 0.000 description 1
- LDLDMPNVKLALQJ-UHFFFAOYSA-N CC(CC(c1cccc(-c2cccc(-c3cc4c(cccc5)c5c(C=CCC5)c5c4cc3)c2)c1)=C1)(c2c1[s]c1ccccc21)c1nc(C2C=CC=CC2)nc(C2=CCCC=C2)n1 Chemical compound CC(CC(c1cccc(-c2cccc(-c3cc4c(cccc5)c5c(C=CCC5)c5c4cc3)c2)c1)=C1)(c2c1[s]c1ccccc21)c1nc(C2C=CC=CC2)nc(C2=CCCC=C2)n1 LDLDMPNVKLALQJ-UHFFFAOYSA-N 0.000 description 1
- VNXAGWPWDGTWBW-UHFFFAOYSA-N CC1(C)c(cc(c(c2c3cccc2)c2)[n]3-c3c(c4ccccc4[s]4)c4cc(C4=CC(c(cc5C67c(cccc8)c8C8=C6CCC=C8)ccc5-c5c7cccc5)NC(c5ccccc5)=N4)c3)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(c(c2c3cccc2)c2)[n]3-c3c(c4ccccc4[s]4)c4cc(C4=CC(c(cc5C67c(cccc8)c8C8=C6CCC=C8)ccc5-c5c7cccc5)NC(c5ccccc5)=N4)c3)c2-c2c1cccc2 VNXAGWPWDGTWBW-UHFFFAOYSA-N 0.000 description 1
- JGSMWZLDSDFDBH-UHFFFAOYSA-N CC1(C)c(cc(cc2)-c(cc3)cc(c4c5C=CCC4)c3[n]5C(CC3c4nc(-c5ccccc5)nc(-c5ccccc5)n4)=Cc4c3c3ccccc3[s]4)c2-c2ccccc12 Chemical compound CC1(C)c(cc(cc2)-c(cc3)cc(c4c5C=CCC4)c3[n]5C(CC3c4nc(-c5ccccc5)nc(-c5ccccc5)n4)=Cc4c3c3ccccc3[s]4)c2-c2ccccc12 JGSMWZLDSDFDBH-UHFFFAOYSA-N 0.000 description 1
- JTKYPCRCEGLWQL-UHFFFAOYSA-N CC1(C)c(cc(cc2)-c(cc3)cc(c4ccccc44)c3[n]4-c3cc(-c4nc(C5C=CC=CC5)nc(-c5ccccc5)n4)c(c4ccccc4[s]4)c4c3)c2-c2ccccc12 Chemical compound CC1(C)c(cc(cc2)-c(cc3)cc(c4ccccc44)c3[n]4-c3cc(-c4nc(C5C=CC=CC5)nc(-c5ccccc5)n4)c(c4ccccc4[s]4)c4c3)c2-c2ccccc12 JTKYPCRCEGLWQL-UHFFFAOYSA-N 0.000 description 1
- DHJGBHFWFAGOTO-UHFFFAOYSA-N CC1(c2ccccc2)N=C(c2ccccc2)N=C(c2cccc(-c3c(c4ccccc4[o]4)c4cc(-c4nc(-c5ccccc5)nc(-c5ccccc5)n4)c3)c2)N1 Chemical compound CC1(c2ccccc2)N=C(c2ccccc2)N=C(c2cccc(-c3c(c4ccccc4[o]4)c4cc(-c4nc(-c5ccccc5)nc(-c5ccccc5)n4)c3)c2)N1 DHJGBHFWFAGOTO-UHFFFAOYSA-N 0.000 description 1
- GQWZBUZVUZDXJN-ZSNJKBEMSA-N CCC/C=C(\C)/c1nc(C2=CC(c3cc(C(c4ccccc4)(c4ccccc4)c4ccccc4)ccc3)=CC3Sc4ccccc4C23)nc(C2C=CC=CC2)n1 Chemical compound CCC/C=C(\C)/c1nc(C2=CC(c3cc(C(c4ccccc4)(c4ccccc4)c4ccccc4)ccc3)=CC3Sc4ccccc4C23)nc(C2C=CC=CC2)n1 GQWZBUZVUZDXJN-ZSNJKBEMSA-N 0.000 description 1
- NVQRKLILLFKQSL-UHNHYTNTSA-N CN1C(c2ccccc2)=NC(C(CC2[n]3c(ccc(C4C=CC=CC4)c4)c4c4ccccc34)Cc3c2c2ccccc2[s]3)=N[C@@H]1c1c2[o]c(cccc3)c3c2ccc1 Chemical compound CN1C(c2ccccc2)=NC(C(CC2[n]3c(ccc(C4C=CC=CC4)c4)c4c4ccccc34)Cc3c2c2ccccc2[s]3)=N[C@@H]1c1c2[o]c(cccc3)c3c2ccc1 NVQRKLILLFKQSL-UHNHYTNTSA-N 0.000 description 1
- FZAQLDBFSGKMOT-UHFFFAOYSA-N CN1C(c2ccccc2)=NC(C2=CCCC=C2)=NC1c1c(c2ccccc2[s]2)c2cc(-c2cc(P(c3ccccc3)c3ccccc3)ccc2)c1 Chemical compound CN1C(c2ccccc2)=NC(C2=CCCC=C2)=NC1c1c(c2ccccc2[s]2)c2cc(-c2cc(P(c3ccccc3)c3ccccc3)ccc2)c1 FZAQLDBFSGKMOT-UHFFFAOYSA-N 0.000 description 1
- QHKQNFLXBAVIIC-UHFFFAOYSA-N COC1=C(C=CC=C1)B(O)O.COC1=C(C=CC=C1)B(O)O Chemical compound COC1=C(C=CC=C1)B(O)O.COC1=C(C=CC=C1)B(O)O QHKQNFLXBAVIIC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- GJBYWSQGSWRPMB-UHFFFAOYSA-N O=P(c1ccccc1)(c1ccccc1)c1cccc(-c2c(c3ccccc3[s]3)c3cc(-c(cc3)c(CCC=C4)c4c3-c3nc(-c4ccccc4)nc(C4=CCCC=C4)n3)c2)c1 Chemical compound O=P(c1ccccc1)(c1ccccc1)c1cccc(-c2c(c3ccccc3[s]3)c3cc(-c(cc3)c(CCC=C4)c4c3-c3nc(-c4ccccc4)nc(C4=CCCC=C4)n3)c2)c1 GJBYWSQGSWRPMB-UHFFFAOYSA-N 0.000 description 1
- HNBMFZWQEXWRRC-UHFFFAOYSA-N OP(c1ccccc1)(c1ccccc1)c1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c(c2ccccc2[s]2)c2c1 Chemical compound OP(c1ccccc1)(c1ccccc1)c1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c(c2ccccc2[s]2)c2c1 HNBMFZWQEXWRRC-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000006193 alkinyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical group C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 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 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MTTZQFIQVHAFEH-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc2c1c(cccc1)c1[n]2-c1cc(C2N=C(c3ccccc3)N=C(c3ccccc3)[N-]2)c(c2ccccc2[s]2)c2c1 Chemical compound c(cc1)ccc1-c(cc1)cc2c1c(cccc1)c1[n]2-c1cc(C2N=C(c3ccccc3)N=C(c3ccccc3)[N-]2)c(c2ccccc2[s]2)c2c1 MTTZQFIQVHAFEH-UHFFFAOYSA-N 0.000 description 1
- DETKHFRLYOGXKO-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c(c2ccccc2[s]2)c2c1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c(cc1)ccc1-c1cc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c(c2ccccc2[s]2)c2c1 DETKHFRLYOGXKO-UHFFFAOYSA-N 0.000 description 1
- JOGAHMXSVUIEDK-UHFFFAOYSA-N c(cc1)ccc1-c1c(c2ccccc2[s]2)c2cc(-c2nc(-c3ccccc3)nc(-c3cccc4c3cccc4)n2)c1 Chemical compound c(cc1)ccc1-c1c(c2ccccc2[s]2)c2cc(-c2nc(-c3ccccc3)nc(-c3cccc4c3cccc4)n2)c1 JOGAHMXSVUIEDK-UHFFFAOYSA-N 0.000 description 1
- CFKPBYAJAKLCKX-UHFFFAOYSA-N c(cc1)ccc1-c1ccc(C2N=C(c(cc3)ccc3-c3ccccc3)N=C(c3cc([s]c4ccccc44)c4c(-c4ccccc4)c3)[N-]2)cc1 Chemical compound c(cc1)ccc1-c1ccc(C2N=C(c(cc3)ccc3-c3ccccc3)N=C(c3cc([s]c4ccccc44)c4c(-c4ccccc4)c3)[N-]2)cc1 CFKPBYAJAKLCKX-UHFFFAOYSA-N 0.000 description 1
- HMBLZVBCFJIWSB-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(-c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c(cccc3)c3[s]3)c3c2)c1 Chemical compound c(cc1)ccc1-c1cccc(-c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c(cccc3)c3[s]3)c3c2)c1 HMBLZVBCFJIWSB-UHFFFAOYSA-N 0.000 description 1
- LWEWLFDQONVWFK-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(cc2)cc3c2[o]c2c3cccc2)nc(-c2cc([s]c3c4cccc3)c4c(-[n](c3c4cccc3)c(cc3)c4c4c3c3ccccc3[n]4-c3ccccc3)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c(cc2)cc3c2[o]c2c3cccc2)nc(-c2cc([s]c3c4cccc3)c4c(-[n](c3c4cccc3)c(cc3)c4c4c3c3ccccc3[n]4-c3ccccc3)c2)n1 LWEWLFDQONVWFK-UHFFFAOYSA-N 0.000 description 1
- CCEVYUCZFMAOTG-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2c(c3ccccc3[o]3)c3cc(-c3nc(c(nccc4)c4cc4)c4cc3)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-c2c(c3ccccc3[o]3)c3cc(-c3nc(c(nccc4)c4cc4)c4cc3)c2)n1 CCEVYUCZFMAOTG-UHFFFAOYSA-N 0.000 description 1
- PISLYDJGBGXAPN-UHFFFAOYSA-N c1ccc(C(c2ccccc2)(c2ccccc2)c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c3ccccc3[s]3)c3c2)cc1 Chemical compound c1ccc(C(c2ccccc2)(c2ccccc2)c2cc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c(c3ccccc3[s]3)c3c2)cc1 PISLYDJGBGXAPN-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001716 carbazoles Chemical group 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 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 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 125000005303 dithiazolyl group Chemical group S1SNC(=C1)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- BSEKBMYVMVYRCW-UHFFFAOYSA-N n-[4-[3,5-bis[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]phenyl]-3-methyl-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=C(C=C(C=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 BSEKBMYVMVYRCW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical group C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005033 thiopyranyl group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
Abstract
Description
前記化学式1において、
N−Hetは、置換もしくは非置換であり、Nを1個以上含む単環または多環のヘテロ環基であり、
Xは、O;またはSであり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、直接結合;置換もしくは非置換の6員環が1個〜3個からなるアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、pおよびmは、1〜3の整数であり、pが2以上の場合、L1は、互いに同一または異なり、mが2以上の場合、L2は、互いに同一または異なり、
Zは、置換もしくは非置換のアルキル基;置換もしくは非置換の6員環が1個〜3個からなるアリール基;トリフェニレン基;P(=O)RR’;SiRR’R”;置換もしくは非置換のアミン基;Nを2以上含む置換もしくは非置換のヘテロアリール基;または下記化学式2で表され、nは、1〜5の整数であり、nが2以上の場合、Zは、互いに同一または異なり、
前記化学式2において、
R11〜R18は、互いに同一または異なり、それぞれ独立して、水素;または置換もしくは非置換のヘテロアリール基であるか;または互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の芳香族炭化水素環、または置換もしくは非置換のヘテロ環を形成し、
R1〜R4は、水素であり、
R5、R、R’およびR”は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のヘテロシクロアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;および置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の芳香族炭化水素環、または置換もしくは非置換のヘテロ環を形成し、aは、0〜2の整数であり、aが2以上の場合、R5は、互いに同一または異なる。
前記化学式3において、
RcおよびRdは、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のヘテロシクロアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;−SiR31R32R33;−P(=O)R31R32;および置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基または置換もしくは非置換のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の脂肪族または芳香族炭化水素環を形成し、
R31、R32およびR33は、互いに同一または異なり、それぞれ独立して、水素;重水素;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
R21およびR22は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
rおよびsは、0〜7の整数であり、rおよびsが2以上の整数の場合、括弧内の置換基は、互いに同一または異なる。
X1は、CR41またはNであり、X2は、CR42またはNであり、X3は、CR43またはNであり、X4は、CR44またはNであり、X5は、CR45またはNであり、
X1〜X5のうちの少なくとも1つは、Nであり、
Yは、NR51またはSであり、
R41〜R45およびR51〜R55は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;P(=O)RR’;SiRR’R”;および置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の芳香族炭化水素環、または置換もしくは非置換のヘテロ環を形成し、
R、R’およびR”の定義は、前記化学式1における定義と同じである。
X1、X2、X3、X5、R42およびR44の定義は、前記化学式6における定義と同じであり、
化学式8において、X1、X3およびX5のうちの1つ以上は、Nであり、
化学式9および10において、X1、X2およびX5のうちの1つ以上は、Nであり、
化学式11において、X1〜X3のうちの1つ以上は、Nであり、
R61〜R65は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;P(=O)RR’;SiRR’R”;および置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基、または置換もしくは非置換のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の脂肪族または芳香族炭化水素環を形成し、
eは、0〜7の整数であり、eが2以上の場合、括弧内の置換基は、互いに同一または異なる。
R11〜R14は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のヘテロアリール基;または互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の芳香族炭化水素環、または置換もしくは非置換のヘテロ環を形成し、
Y1は、O;S;NR81;またはCR82R83であり、
R71およびR81〜R83は、互いに同一または異なり、それぞれ独立して、水素;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
fは、0〜4の整数であり、fが2以上の整数の場合、括弧内の置換基は、互いに同一または異なる。
RcおよびRdは、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のヘテロシクロアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;−SiR31R32R33;−P(=O)R31R32;および置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基または置換もしくは非置換のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の脂肪族または芳香族炭化水素環を形成し、
R31、R32およびR33は、互いに同一または異なり、それぞれ独立して、水素;重水素;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
R21およびR22は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
rおよびsは、0〜7の整数であり、rおよびsが2以上の整数の場合、括弧内の置換基は、互いに同一または異なる。
1−ブロモ−5−クロロ−3−フルオロ−2−ヨードベンゼン(1−bromo−5−chloro−3−fluoro−2−iodobenzene)200.0g(596.4mM)、(2−メトキシフェニル)ボロン酸((2−methoxyphenyl)boronic acid)82.4g(542.2mM)、Pd(PPh3)4 31.3g(27.1mM)、K2CO3 150.0g(1084.4mM)を1,4−dioxane/H2O1L/200mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:10)で精製して、目的化合物1−5−5 137g(80%)を得た。
化合物1−5−5 82g(259.8mM)、BBr3 49mL(519.7mM)をDCM800mLに溶かした後、1時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:1)で精製して、目的化合物1−5−4 65.3g(83%)を得た。
化合物1−5−4 65.3g(216.5mM)、K2CO3 59.9g(433.1mM)をDMF300mLに溶かした後、4時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:5)で精製し、メタノールで再結晶して、目的化合物1−5−3 54.8g(90%)を得た。
化合物1−5−3 54g(191mM)、ビス(ピナコラト)ジボロン(bis(pinacolato)diboron)73.0g(287.7mM)、PdCl2(dppf)7.0g(9.5mM)、KOAc56.2g(573.0mM)を1,4−ジオキサン(1,4−dioxane)500mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物1−5−2 53g(85%)を得た。
化合物1−5−2 53g(161.3mM)、2−クロロ−4,6−ジフェニル−1,3,5−トリアジン(2−chloro−4,6−diphenyl−1,3,5−triazine)47.5g(177.4mM)、Pd(PPh3)4 9.3g(8.1mM)、K2CO3 44.6g(322.6mM)を1,4−dioxane/H2O300/60mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物1−5−1 57.3g(82%)を得た。
化合物1−5−1 57g(131.3mM)、トリフェニレン−2−イルボロン酸(triphenylen−2−ylboronic acid)42.9g(157.6mM)、Pd(PPh3)4 7.6g(6.6mM)、K2CO3 36.3g(262.6mM)を1,4−dioxane/H2O300/60mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物1−5 70.6g(86%)を得た。
化合物1−5−1 10g(23.0mM)、9H−カルバゾール(9H−carbazole)42.9g(4.2mM)、Pd2(dba)3 1.1g(1.2mM)、P(t−Bu)3 1.5mL(2.3mM)、NaOt−Bu4.4g(46mM)を1,4−ジオキサン(1,4−dioxane)200mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物1−30 11.2g(86%)を得た。
化合物1−5−3 10g(35.5mM)、トリフェニレン−2−イルボロン酸(triphenylen−2−ylboronic acid)10.6g(39.1mM)、Pd2(dba)3 1.6g(1.8mM)、SPhos1.5g(3.55mM)、K3PO4 15.1g(71.0mM)を1,4−dioxane/H2O200/40mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物2−5−2 13.1g(86%)を得た。
化合物2−5−2 13g(30.3mM)、ビス(ピナコラト)ジボロン(bis(pinacolato)diboron)73.0g(11.5mM)、Pd2(dba)3 2.8g(3.0mM)、PCy3 1.7g(6.1mM)、KOAc8.9g(90.9mM)を1,4−dioxane100mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物2−5−1 14g(89%)を得た。
化合物2−5−1 14g(26.9mM)、2−クロロ−4,6−ジフェニル−1,3,5−トリアジン(2−chloro−4,6−diphenyl−1,3,5−triazine)7.9g(29.6mM)、Pd(PPh3)4 1.5g(1.3mM)、K2CO3 7.4g(53.8mM)を1,4−dioxane/H2O200/40mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物2−5 13.8g(82%)を得た。
化合物1−5−3 10g(35.5mM)、3−フェニル−9H−カルバゾール(3−phenyl−9H−carbazole)7.2g(29.6mM)、Pd2(dba)3 1.4g(1.5mM)、P(t−Bu)3 2.0mL(3.0mM)、NaOt−Bu5.7g(59.2mM)を1,4−ジオキサン(1,4−dioxane)200mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物2−33−2 11.3g(86%)を得た。
化合物2−33−2 10g(22.5mM)、ビス(ピナコラト)ジボロン(bis(pinacolato)diboron)8.6g(33.7mM)、Pd2(dba)3 2.1g(2.3mM)、PCy3 1.3g(4.5mM)、KOAc6.6g(67.5mM)を1,4−dioxane200mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物2−33−1 10.7g(89%)を得た。
化合物2−33−1 10g(18.7mM)、2−クロロ−4,6−ジフェニル−1,3,5−トリアジン(2−chloro−4,6−diphenyl−1,3,5−triazine)5.5g(20.5mM)、Pd(PPh3)4 1.1g(0.9mM)、K2CO3 5.2g(37.4mM)を1,4−dioxane/H2O200/40mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物2−33 9.8g(82%)を得た。
1−ブロモ−5−クロロ−3フルオロ−2−ヨードベンゼン(1−bromo−5−chloro−3−fluoro−2−iodobenzene)20.0g(59.6mM)、2−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)ベンゼンチオール(2−(4,4,5,5−tetramethyl−1,3,2−dioxaborolan−2−yl)benzenethiol)12.8g(54.2mM)、Pd(PPh3)4 3.1g(2.7mM)、K2CO3 15.0g(108.4mM)を1,4−dioxane/H2O200/40mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:10)に精製して、目的化合物3−5−4 13.8g(80%)を得た。
化合物3−5−4 6.9g(21.6mM)、K2CO3 59.9g(43.3mM)をDMF60mLに溶かした後、4時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:5)で精製し、メタノールで再結晶して、目的化合物3−5−3 5.8g(90%)を得た。
3−ブロモ−1,1’−ビフェニル3.7g(15.8mM)、9−フェニル−9H,9’H−3,3’−ビカルバゾール6.5g(15.8mM)、CuI3.0g(15.8mM)、トランス−1,2−ジアミノシクロヘキサン1.9mL(15.8mM)、K3PO4 3.3g(31.6mM)を1,4−オキサン100mLに溶かした後、24時間還流した。反応が完了した後、室温で蒸留水とDCMを入れて抽出し、有機層はMgSO4で乾燥させた後、回転蒸発器で溶媒を除去した。反応物はカラムクロマトグラフィー(DCM:Hex=1:3)で精製し、メタノールで再結晶して、目的化合物5−3 7.5g(85%)を得た。
1,500Åの厚さにITOが薄膜コーティングされたガラス基板を蒸留水超音波洗浄した。蒸留水洗浄が終わると、アセトン、メタノール、イソプロピルアルコールなどの溶剤で超音波洗浄をし乾燥させた後、UV洗浄機でUVを用いて5分間UVO処理した。以後、基板をプラズマ洗浄機(PT)に搬送させた後、真空状態でITOの仕事関数および残膜除去のためにプラズマ処理をして、有機蒸着用熱蒸着装置に搬送した。
1,500Åの厚さにITOが薄膜コーティングされたガラス基板を蒸留水超音波洗浄した。蒸留水洗浄が終わると、アセトン、メタノール、イソプロピルアルコールなどの溶剤で超音波洗浄をし乾燥させた後、UV洗浄機でUVを用いて5分間UVO処理した。以後、基板をプラズマ洗浄機(PT)に搬送させた後、真空状態でITOの仕事関数および残膜除去のためにプラズマ処理をして、有機蒸着用熱蒸着装置に搬送した。
200:陽極
300:有機物層
301:正孔注入層
302:正孔輸送層
303:発光層
304:正孔阻止層
305:電子輸送層
306:電子注入層
400:陰極
Claims (17)
- 下記化学式1で表されるヘテロ環化合物:
前記化学式1において、
N−Hetは、置換もしくは非置換であり、Nを1個以上含む単環または多環のヘテロ環基であり、
Xは、O;またはSであり、
L1およびL2は、互いに同一または異なり、それぞれ独立して、直接結合;置換もしくは非置換の6員環が1個〜3個からなるアリーレン基;または置換もしくは非置換のヘテロアリーレン基であり、pおよびmは、1〜3の整数であり、pが2以上の場合、L1は、互いに同一または異なり、mが2以上の場合、L2は、互いに同一または異なり、
Zは、置換もしくは非置換のアルキル基;置換もしくは非置換の6員環が1個〜3個からなるアリール基;トリフェニレン基;P(=O)RR’;SiRR’R”;置換もしくは非置換のアミン基;Nを2以上含む置換もしくは非置換のヘテロアリール基;または下記化学式2で表され、nは、1〜5の整数であり、nが2以上の場合、Zは、互いに同一または異なり、
前記化学式2において、
R11〜R18は、互いに同一または異なり、それぞれ独立して、水素;または置換もしくは非置換のヘテロアリール基であるか;または互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の芳香族炭化水素環、または置換もしくは非置換のヘテロ環を形成し、
R1〜R4は、水素であり、
R5、R、R’およびR”は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のヘテロシクロアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;および置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の芳香族炭化水素環、または置換もしくは非置換のヘテロ環を形成し、aは、0〜2の整数であり、aが2以上の場合、R5は、互いに同一または異なる。 - 前記N−Hetは、下記化学式6または7で表されるものである、請求項1に記載のヘテロ環化合物:
前記化学式6および7において、
X1は、CR41またはNであり、X2は、CR42またはNであり、X3は、CR43またはNであり、X4は、CR44またはNであり、X5は、CR45またはNであり、
X1〜X5のうちの少なくとも1つは、Nであり、
Yは、NR51またはSであり、
R41〜R45およびR51〜R55は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;P(=O)RR’;SiRR’R”;および置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基または置換もしくは非置換のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の芳香族炭化水素環、または置換もしくは非置換のヘテロ環を形成し、
R、R’およびR”の定義は、前記化学式1における定義と同じである。 - 前記化学式6は、下記化学式8〜12のいずれか1つで表されるものである、請求項3に記載のヘテロ環化合物:
前記化学式8〜12において、
X1、X2、X3、X5、R42およびR44の定義は、前記化学式6における定義と同じであり、
化学式8において、X1、X3およびX5のうちの1つ以上は、Nであり、
化学式9および10において、X1、X2およびX5のうちの1つ以上は、Nであり、
化学式11において、X1〜X3のうちの1つ以上は、Nであり、
R61〜R65は、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;P(=O)RR’;SiRR’R”;および置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基または置換もしくは非置換のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の脂肪族または芳香族炭化水素環を形成し、
eは、0〜7の整数であり、eが2以上の場合、括弧内の置換基は、互いに同一または異なる。 - 第1電極と、前記第1電極に対向して備えられた第2電極と、前記第1電極と前記第2電極との間に備えられた1層以上の有機物層とを含む有機発光素子であって、前記有機物層のうちの1層以上は、請求項1〜5のいずれか1項に記載のヘテロ環化合物を含む有機発光素子。
- 前記化学式1で表されるヘテロ環化合物を含む有機物層は、下記化学式3で表されるヘテロ環化合物をさらに含むものである、請求項6に記載の有機発光素子:
前記化学式3において、
RcおよびRdは、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のヘテロシクロアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;−SiR31R32R33;−P(=O)R31R32;および置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基または置換もしくは非置換のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の脂肪族または芳香族炭化水素環を形成し、
R31、R32およびR33は、互いに同一または異なり、それぞれ独立して、水素;重水素;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
R21およびR22は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
rおよびsは、0〜7の整数であり、rおよびsが2以上の整数の場合、括弧内の置換基は、互いに同一または異なる。 - 前記R21およびR22は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のC6〜C40のアリール基である、請求項7に記載の有機発光素子。
- 前記有機物層は、発光層を含み、前記発光層は、前記ヘテロ環化合物を含む、請求項6に記載の有機発光素子。
- 前記有機物層は、発光層を含み、前記発光層は、ホスト物質を含み、前記ホスト物質は、前記ヘテロ環化合物を含む、請求項6に記載の有機発光素子。
- 前記有機物層は、電子注入層または電子輸送層を含み、前記電子注入層または電子輸送層は、前記ヘテロ環化合物を含む、請求項6に記載の有機発光素子。
- 前記有機物層は、電子阻止層または正孔阻止層を含み、前記電子阻止層または正孔阻止層は、前記ヘテロ環化合物を含む、請求項6に記載の有機発光素子。
- 前記有機発光素子は、発光層、正孔注入層、正孔輸送層、電子注入層、電子輸送層、電子阻止層、および正孔阻止層からなる群より選択される1層または2層以上をさらに含む、請求項6に記載の有機発光素子。
- 請求項1〜5のいずれか1項に記載のヘテロ環化合物、および下記化学式3で表されるヘテロ環化合物を含む有機発光素子の有機物層用組成物:
前記化学式3において、
RcおよびRdは、互いに同一または異なり、それぞれ独立して、水素;重水素;ハロゲン基;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のアルケニル基;置換もしくは非置換のアルキニル基;置換もしくは非置換のアルコキシ基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のヘテロシクロアルキル基;置換もしくは非置換のアリール基;置換もしくは非置換のヘテロアリール基;−SiR31R32R33;−P(=O)R31R32;および置換もしくは非置換のアルキル基、置換もしくは非置換のアリール基または置換もしくは非置換のヘテロアリール基で置換もしくは非置換のアミン基からなる群より選択されるか、互いに隣接する2以上の基は、互いに結合して置換もしくは非置換の脂肪族または芳香族炭化水素環を形成し、
R31、R32およびR33は、互いに同一または異なり、それぞれ独立して、水素;重水素;−CN;置換もしくは非置換のアルキル基;置換もしくは非置換のシクロアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
R21およびR22は、互いに同一または異なり、それぞれ独立して、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロアリール基であり、
rおよびsは、0〜7の整数であり、rおよびsが2以上の整数の場合、括弧内の置換基は、互いに同一または異なる。 - 基板を用意するステップと、
前記基板上に第1電極を形成するステップと、
前記第1電極上に1層以上の有機物層を形成するステップと、
前記有機物層上に第2電極を形成するステップとを含み、
前記有機物層を形成するステップは、請求項15に記載の有機物層用組成物を用いて1層以上の有機物層を形成するステップを含む有機発光素子の製造方法。 - 前記有機物層を形成するステップは、前記化学式1のヘテロ環化合物、および前記化学式3のヘテロ環化合物を予備混合(pre−mixed)して、熱真空蒸着方法を利用して形成する、請求項16に記載の有機発光素子の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020180072029A KR102322698B1 (ko) | 2018-06-22 | 2018-06-22 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 및 유기 발광 소자의 제조 방법 |
KR10-2018-0072029 | 2018-06-22 | ||
PCT/KR2019/007333 WO2019245262A1 (ko) | 2018-06-22 | 2019-06-18 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 및 유기 발광 소자의 제조 방법 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2021528379A true JP2021528379A (ja) | 2021-10-21 |
Family
ID=68984248
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020566741A Pending JP2021528379A (ja) | 2018-06-22 | 2019-06-18 | ヘテロ環化合物、これを含む有機発光素子、有機発光素子の有機物層用組成物および有機発光素子の製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20210179596A1 (ja) |
EP (1) | EP3812381A4 (ja) |
JP (1) | JP2021528379A (ja) |
KR (2) | KR102322698B1 (ja) |
CN (1) | CN112313225A (ja) |
TW (1) | TWI826473B (ja) |
WO (1) | WO2019245262A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2022519980A (ja) * | 2018-12-11 | 2022-03-28 | エルティー・マテリアルズ・カンパニー・リミテッド | ヘテロ環化合物、これを含む有機発光素子、その製造方法および有機物層用組成物 |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102328684B1 (ko) * | 2019-01-08 | 2021-11-18 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
CN111072637B (zh) * | 2019-12-27 | 2023-04-07 | 吉林奥来德光电材料股份有限公司 | 有机发光化合物、其制备方法及有机发光器件 |
CN111303134A (zh) * | 2020-03-25 | 2020-06-19 | 烟台显华化工科技有限公司 | 一种有机发光材料及有机电致发光器件 |
CN111410655B (zh) * | 2020-03-30 | 2021-09-24 | 北京绿人科技有限责任公司 | 一种有机化合物及其应用、一种有机电致发光器件 |
WO2021221475A1 (ko) * | 2020-04-29 | 2021-11-04 | 주식회사 엘지화학 | 유기 발광 소자 |
CN111848493B (zh) * | 2020-08-28 | 2022-10-14 | 长春海谱润斯科技股份有限公司 | 一种含有螺二芴的衍生物及其有机电致发光器件 |
WO2022231322A1 (ko) * | 2021-04-27 | 2022-11-03 | 주식회사 엘지화학 | 유기 발광 소자 |
KR20230000949A (ko) * | 2021-06-24 | 2023-01-03 | 엘티소재주식회사 | 헤테로고리 화합물, 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 |
WO2023149718A1 (ko) * | 2022-02-04 | 2023-08-10 | 엘티소재주식회사 | 헤테로고리 화합물을 포함하는 유기 발광 소자, 상기 유기 발광 소자의 유기물층용 조성물 및 상기 유기 발광 소자의 제조방법 |
KR102552268B1 (ko) * | 2022-02-24 | 2023-07-07 | 삼성디스플레이 주식회사 | 헤테로고리 화합물을 포함한 발광 소자, 상기 발광 소자를 포함한 전자 장치 및 상기 헤테로고리 화합물 |
KR20240025997A (ko) * | 2022-08-19 | 2024-02-27 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기물층용 조성물 |
KR102651354B1 (ko) * | 2022-10-31 | 2024-03-27 | 엘티소재주식회사 | 유기 발광 소자 및 유기물층 형성용 조성물 |
CN116283943B (zh) * | 2023-05-23 | 2023-08-04 | 苏州驳凡熹科技有限公司 | 一种有机化合物、电致发光材料及电致发光器件 |
CN116761450A (zh) * | 2023-08-18 | 2023-09-15 | 苏州驳凡熹科技有限公司 | 一种有机电致发光元件 |
Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008135498A (ja) * | 2006-11-28 | 2008-06-12 | Toray Ind Inc | 発光素子 |
WO2012108388A1 (ja) * | 2011-02-07 | 2012-08-16 | 出光興産株式会社 | ビスカルバゾール誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
KR20130083817A (ko) * | 2012-01-13 | 2013-07-23 | 덕산하이메탈(주) | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
US20150318487A1 (en) * | 2014-05-02 | 2015-11-05 | Samsung Display Co., Ltd. | Organic light-emitting device |
US20160111657A1 (en) * | 2014-10-17 | 2016-04-21 | Samsung Electronics Co., Ltd., | Carbazole-based compound and organic light emitting device including the same |
KR20160080090A (ko) * | 2014-12-29 | 2016-07-07 | 주식회사 동진쎄미켐 | 신규한 화합물 및 이를 포함하는 유기발광소자 |
JP2016149473A (ja) * | 2015-02-13 | 2016-08-18 | コニカミノルタ株式会社 | 芳香族複素環誘導体、それを用いた有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
WO2017018795A2 (ko) * | 2015-07-27 | 2017-02-02 | 희성소재(주) | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
KR20170057660A (ko) * | 2015-11-17 | 2017-05-25 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 전자 소자 |
JP2017524707A (ja) * | 2014-07-29 | 2017-08-31 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
KR20170111387A (ko) * | 2016-03-28 | 2017-10-12 | 에스에프씨 주식회사 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
WO2017178311A1 (de) * | 2016-04-11 | 2017-10-19 | Merck Patent Gmbh | Heterocyclische verbindungen mit dibenzofuran- und/oder dibenzothiophen-strukturen |
KR20170136440A (ko) * | 2016-06-01 | 2017-12-11 | 주식회사 엘지화학 | 신규한 화합물 및 이를 포함하는 유기 발광 소자 |
KR20180012199A (ko) * | 2016-07-26 | 2018-02-05 | 주식회사 엘지화학 | 유기 발광 소자 |
KR20180031224A (ko) * | 2016-09-19 | 2018-03-28 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
US20180123055A1 (en) * | 2015-04-23 | 2018-05-03 | Sfc Co., Ltd. | Compound for organic light-emitting device and organic light-emitting device including same |
WO2018190516A1 (ko) * | 2017-04-13 | 2018-10-18 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4356429A (en) | 1980-07-17 | 1982-10-26 | Eastman Kodak Company | Organic electroluminescent cell |
US9732069B2 (en) * | 2014-05-21 | 2017-08-15 | Samsung Electronics Co., Ltd. | Carbazole compound and organic light emitting device including the same |
KR101907103B1 (ko) | 2016-12-20 | 2018-10-12 | (주)한국거래소 | 장외주식 거래 지원시스템 |
-
2018
- 2018-06-22 KR KR1020180072029A patent/KR102322698B1/ko active IP Right Grant
-
2019
- 2019-06-18 WO PCT/KR2019/007333 patent/WO2019245262A1/ko active Application Filing
- 2019-06-18 EP EP19823085.6A patent/EP3812381A4/en active Pending
- 2019-06-18 CN CN201980040698.0A patent/CN112313225A/zh active Pending
- 2019-06-18 JP JP2020566741A patent/JP2021528379A/ja active Pending
- 2019-06-18 US US17/058,199 patent/US20210179596A1/en active Pending
- 2019-06-20 TW TW108121430A patent/TWI826473B/zh active
-
2021
- 2021-06-10 KR KR1020210075411A patent/KR102360681B1/ko active IP Right Review Request
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008135498A (ja) * | 2006-11-28 | 2008-06-12 | Toray Ind Inc | 発光素子 |
WO2012108388A1 (ja) * | 2011-02-07 | 2012-08-16 | 出光興産株式会社 | ビスカルバゾール誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
KR20130083817A (ko) * | 2012-01-13 | 2013-07-23 | 덕산하이메탈(주) | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
US20150318487A1 (en) * | 2014-05-02 | 2015-11-05 | Samsung Display Co., Ltd. | Organic light-emitting device |
JP2017524707A (ja) * | 2014-07-29 | 2017-08-31 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
US20160111657A1 (en) * | 2014-10-17 | 2016-04-21 | Samsung Electronics Co., Ltd., | Carbazole-based compound and organic light emitting device including the same |
KR20160080090A (ko) * | 2014-12-29 | 2016-07-07 | 주식회사 동진쎄미켐 | 신규한 화합물 및 이를 포함하는 유기발광소자 |
JP2016149473A (ja) * | 2015-02-13 | 2016-08-18 | コニカミノルタ株式会社 | 芳香族複素環誘導体、それを用いた有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
US20180123055A1 (en) * | 2015-04-23 | 2018-05-03 | Sfc Co., Ltd. | Compound for organic light-emitting device and organic light-emitting device including same |
WO2017018795A2 (ko) * | 2015-07-27 | 2017-02-02 | 희성소재(주) | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
KR20170057660A (ko) * | 2015-11-17 | 2017-05-25 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 전자 소자 |
KR20170111387A (ko) * | 2016-03-28 | 2017-10-12 | 에스에프씨 주식회사 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
WO2017178311A1 (de) * | 2016-04-11 | 2017-10-19 | Merck Patent Gmbh | Heterocyclische verbindungen mit dibenzofuran- und/oder dibenzothiophen-strukturen |
KR20170136440A (ko) * | 2016-06-01 | 2017-12-11 | 주식회사 엘지화학 | 신규한 화합물 및 이를 포함하는 유기 발광 소자 |
KR20180012199A (ko) * | 2016-07-26 | 2018-02-05 | 주식회사 엘지화학 | 유기 발광 소자 |
KR20180031224A (ko) * | 2016-09-19 | 2018-03-28 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
WO2018190516A1 (ko) * | 2017-04-13 | 2018-10-18 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2022519980A (ja) * | 2018-12-11 | 2022-03-28 | エルティー・マテリアルズ・カンパニー・リミテッド | ヘテロ環化合物、これを含む有機発光素子、その製造方法および有機物層用組成物 |
Also Published As
Publication number | Publication date |
---|---|
TWI826473B (zh) | 2023-12-21 |
US20210179596A1 (en) | 2021-06-17 |
EP3812381A1 (en) | 2021-04-28 |
TW202000862A (zh) | 2020-01-01 |
KR102360681B9 (ko) | 2023-06-12 |
KR20210071929A (ko) | 2021-06-16 |
KR102322698B1 (ko) | 2021-11-09 |
WO2019245262A1 (ko) | 2019-12-26 |
KR20200000122A (ko) | 2020-01-02 |
EP3812381A4 (en) | 2022-03-09 |
CN112313225A (zh) | 2021-02-02 |
KR102360681B1 (ko) | 2022-02-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP7062305B2 (ja) | 有機発光素子および有機発光素子の有機物層用組成物 | |
TWI726241B (zh) | 雜環化合物與包含其的有機發光裝置 | |
KR102360681B1 (ko) | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 및 유기 발광 소자의 제조 방법 | |
TWI703201B (zh) | 有機發光裝置、其製造方法以及用於有機發光裝置之有機材料層的組成物 | |
KR101959821B1 (ko) | 유기 발광 소자, 이의 제조방법 및 유기 발광 소자의 유기물층용 조성물 | |
TWI735047B (zh) | 有機發光元件、組成物以及製造有機發光元件的方法 | |
JP2022519980A (ja) | ヘテロ環化合物、これを含む有機発光素子、その製造方法および有機物層用組成物 | |
TWI795780B (zh) | 有機發光元件、其製造方法以及有機發光元件之有機層的組成物 | |
JP2021528408A (ja) | ヘテロ環化合物、これを含む有機発光素子、有機発光素子の有機物層用組成物および有機発光素子の製造方法 | |
JP2022101491A (ja) | ヘテロ環化合物、これを含む有機発光素子、その製造方法および有機物層用組成物 | |
CN115515950A (zh) | 杂环化合物、含其的有机发光装置及其制法及用于有机层的组成物 | |
TWI821316B (zh) | 雜環化合物、有機發光元件及其製造方法以及用於有機發光元件的有機材料層的組成物 | |
TWI795694B (zh) | 雜環化合物、包括其的有機發光元件、用於有機發光元件之有機層的組成物以及有機發光元件製造方法 | |
JP2021516656A (ja) | ヘテロ環化合物およびこれを含む有機発光素子 | |
JP7040817B2 (ja) | ヘテロ環化合物およびこれを含む有機発光素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20220513 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20230518 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20230530 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230824 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20231031 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20240130 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20240402 |