KR20210119196A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
- Publication number
- KR20210119196A KR20210119196A KR1020200035798A KR20200035798A KR20210119196A KR 20210119196 A KR20210119196 A KR 20210119196A KR 1020200035798 A KR1020200035798 A KR 1020200035798A KR 20200035798 A KR20200035798 A KR 20200035798A KR 20210119196 A KR20210119196 A KR 20210119196A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- compound
- formula
- light emitting
- independently
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 92
- -1 t-butylphenyl Chemical group 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005104 aryl silyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000006819 (C2-60) heteroaryl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 30
- 239000011368 organic material Substances 0.000 abstract description 30
- 238000000034 method Methods 0.000 abstract description 19
- 239000000126 substance Substances 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 86
- 238000002347 injection Methods 0.000 description 26
- 239000007924 injection Substances 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 239000000758 substrate Substances 0.000 description 13
- 230000032258 transport Effects 0.000 description 13
- 239000008199 coating composition Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 239000010405 anode material Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- NVCQMRCDIJQSAP-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)NC1=CC=2C(C3=CC=CC=C3C2C=C1)(C)C Chemical compound C(C)(C)(C)C1=CC=C(C=C1)NC1=CC=2C(C3=CC=CC=C3C2C=C1)(C)C NVCQMRCDIJQSAP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012044 organic layer Substances 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
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UPEIHONFONOAEW-UHFFFAOYSA-N 1,3-dimethyl-9H-fluoren-2-amine Chemical compound NC1=C(C=2CC3=CC=CC=C3C2C=C1C)C UPEIHONFONOAEW-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PFYHAAAQPNMZHO-UHFFFAOYSA-N Methyl 2-methoxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC PFYHAAAQPNMZHO-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 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
- 229930192474 thiophene Chemical group 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- YBNDRTRLXPEWKQ-UHFFFAOYSA-N (4-chloro-2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1F YBNDRTRLXPEWKQ-UHFFFAOYSA-N 0.000 description 1
- 0 *N(*)c1ccc(c(cc2[o]c(cc(c(c([o]3)c4)ccc4N(*)[Al])c3c3)c3c2c2)c2[o]2)c2c1 Chemical compound *N(*)c1ccc(c(cc2[o]c(cc(c(c([o]3)c4)ccc4N(*)[Al])c3c3)c3c2c2)c2[o]2)c2c1 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-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
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 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
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical group C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VFOUUTVFCMSSCY-NVVMKNGRSA-N C/C=C(\C[C@H]1[C@@H](C2)Nc3cccc4c3ccc(-c3cc(cccc5)c5[o]3)c4)/OC2=C1Oc1ccc2[o]c3cc(N(c(cc4)cc(C5(c6ccccc6)c6ccccc6)c4-c4c5cccc4)c4cccc5c4ccc(-c4cc(cccc6)c6[o]4)c5)ccc3c2c1 Chemical compound C/C=C(\C[C@H]1[C@@H](C2)Nc3cccc4c3ccc(-c3cc(cccc5)c5[o]3)c4)/OC2=C1Oc1ccc2[o]c3cc(N(c(cc4)cc(C5(c6ccccc6)c6ccccc6)c4-c4c5cccc4)c4cccc5c4ccc(-c4cc(cccc6)c6[o]4)c5)ccc3c2c1 VFOUUTVFCMSSCY-NVVMKNGRSA-N 0.000 description 1
- RCWVKEJVDOHUTJ-UHFFFAOYSA-N CC(C)(C)c(cc1)cc(c2cc(C(C)(C)C)ccc22)c1[n]2-c(cc1)ccc1N(c(cc1)cc2c1-c1ccccc1C2(c1ccccc1)c1ccccc1)c1ccc(c(cc(c(c2c3)c4)[o]c2cc2c3[o]c3cc(N(c(cc5)ccc5-[n]5c6ccc(C(C)(C)C)cc6c6cc(C(C)(C)C)ccc56)c(cc5)cc(C6(c7ccccc7)c7ccccc7)c5-c5c6cccc5)ccc23)c4[o]2)c2c1 Chemical compound CC(C)(C)c(cc1)cc(c2cc(C(C)(C)C)ccc22)c1[n]2-c(cc1)ccc1N(c(cc1)cc2c1-c1ccccc1C2(c1ccccc1)c1ccccc1)c1ccc(c(cc(c(c2c3)c4)[o]c2cc2c3[o]c3cc(N(c(cc5)ccc5-[n]5c6ccc(C(C)(C)C)cc6c6cc(C(C)(C)C)ccc56)c(cc5)cc(C6(c7ccccc7)c7ccccc7)c5-c5c6cccc5)ccc23)c4[o]2)c2c1 RCWVKEJVDOHUTJ-UHFFFAOYSA-N 0.000 description 1
- RJWTXKFITVUJLO-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c(cc1)cc(C2(C)C)c1-c1c2cccc1)c1ccc2c(c3c(cc4)[o]c5c(c(ccc(N(c6ccc(C(C)(C)C)cc6)c(cc6)cc(C7(C)C)c6-c6c7cccc6)c6)c6[o]6)c6ccc35)c4[o]c2c1 Chemical compound CC(C)(C)c(cc1)ccc1N(c(cc1)cc(C2(C)C)c1-c1c2cccc1)c1ccc2c(c3c(cc4)[o]c5c(c(ccc(N(c6ccc(C(C)(C)C)cc6)c(cc6)cc(C7(C)C)c6-c6c7cccc6)c6)c6[o]6)c6ccc35)c4[o]c2c1 RJWTXKFITVUJLO-UHFFFAOYSA-N 0.000 description 1
- NVKZSILRWBKCOD-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c(cc1)cc(C2(c3ccccc3)c3ccccc3)c1-c1c2cccc1)c(cc1)cc([o]c2c3)c1c2cc1c3c(cc2[o]c3cc(N(c4ccc(C(C)(C)C)cc4)c(cc4)cc(C5(c6ccccc6)c6ccccc6)c4-c4c5cccc4)ccc3c2c2)c2[o]1 Chemical compound CC(C)(C)c(cc1)ccc1N(c(cc1)cc(C2(c3ccccc3)c3ccccc3)c1-c1c2cccc1)c(cc1)cc([o]c2c3)c1c2cc1c3c(cc2[o]c3cc(N(c4ccc(C(C)(C)C)cc4)c(cc4)cc(C5(c6ccccc6)c6ccccc6)c4-c4c5cccc4)ccc3c2c2)c2[o]1 NVKZSILRWBKCOD-UHFFFAOYSA-N 0.000 description 1
- JPJWQDKKTBGWMH-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c(cc1)cc2c1-c1c(cccc3)c3ccc1C2(c1ccccc1)c1ccccc1)c(cc1)cc2c1c(cc1[o]c(cc(c(c([o]3)c4)ccc4N(c4ccc(C(C)(C)C)cc4)c(cc4)cc(C5(c6ccccc6)c6ccccc6)c4-c4c5ccc5c4cccc5)c3c3)c3c1c1)c1[o]2 Chemical compound CC(C)(C)c(cc1)ccc1N(c(cc1)cc2c1-c1c(cccc3)c3ccc1C2(c1ccccc1)c1ccccc1)c(cc1)cc2c1c(cc1[o]c(cc(c(c([o]3)c4)ccc4N(c4ccc(C(C)(C)C)cc4)c(cc4)cc(C5(c6ccccc6)c6ccccc6)c4-c4c5ccc5c4cccc5)c3c3)c3c1c1)c1[o]2 JPJWQDKKTBGWMH-UHFFFAOYSA-N 0.000 description 1
- GRDUEWCGXXTTIS-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1N(c(cc12)ccc1-c1cc(cccc3)c3cc1C2(c1ccccc1)c1ccccc1)c(cc1)cc([o]c2c3)c1c2cc([o]c1c2)c3c1cc([o]c1c3)c2c1ccc3N(c1ccc(C(C)(C)C)cc1)c(cc1)cc(C2(c3ccccc3)c3ccccc3)c1-c1c2cc(cccc2)c2c1 Chemical compound CC(C)(C)c(cc1)ccc1N(c(cc12)ccc1-c1cc(cccc3)c3cc1C2(c1ccccc1)c1ccccc1)c(cc1)cc([o]c2c3)c1c2cc([o]c1c2)c3c1cc([o]c1c3)c2c1ccc3N(c1ccc(C(C)(C)C)cc1)c(cc1)cc(C2(c3ccccc3)c3ccccc3)c1-c1c2cc(cccc2)c2c1 GRDUEWCGXXTTIS-UHFFFAOYSA-N 0.000 description 1
- LCEYPVXWPNHYKJ-UHFFFAOYSA-N CC(C)(C)c1ccc(C2(c(cc(cc3)N(c4ccccc4)c4ccc(c(c([o]5)c6)cc7c6c(cc6[o]c8cc(N(c9ccccc9)c(cc9)cc%10c9-c9ccccc9C%10(c9ccc(C(C)(C)C)cc9)c9ccc(C(C)(C)C)cc9)ccc8c6c6)c6[o]7)c5c4)c3-c3c2cccc3)c2ccc(C(C)(C)C)cc2)cc1 Chemical compound CC(C)(C)c1ccc(C2(c(cc(cc3)N(c4ccccc4)c4ccc(c(c([o]5)c6)cc7c6c(cc6[o]c8cc(N(c9ccccc9)c(cc9)cc%10c9-c9ccccc9C%10(c9ccc(C(C)(C)C)cc9)c9ccc(C(C)(C)C)cc9)ccc8c6c6)c6[o]7)c5c4)c3-c3c2cccc3)c2ccc(C(C)(C)C)cc2)cc1 LCEYPVXWPNHYKJ-UHFFFAOYSA-N 0.000 description 1
- MILSYCKGLDDVLM-UHFFFAOYSA-N CC(C)(c1ccccc1)c1ccccc1 Chemical compound CC(C)(c1ccccc1)c1ccccc1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 1
- YDBRNCCSUQXIRY-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c(cc3)cc([o]c4ccc56)c3c4c5[o]c(cc3)c6c4c3[o]c3cc(N(c(cc5)cc(C6(C)C)c5-c5c6cccc5)c5cccc-6c5C5(C)c7ccccc-67)c5cc43)c3cccc-4c3C(C)(C)c3ccccc-43)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c(cc3)cc([o]c4ccc56)c3c4c5[o]c(cc3)c6c4c3[o]c3cc(N(c(cc5)cc(C6(C)C)c5-c5c6cccc5)c5cccc-6c5C5(C)c7ccccc-67)c5cc43)c3cccc-4c3C(C)(C)c3ccccc-43)c2-c2c1cccc2 YDBRNCCSUQXIRY-UHFFFAOYSA-N 0.000 description 1
- PWNSHUNKRFETOH-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3cc4ccccc4[o]3)c(cc3)cc4c3c3c(c5ccc6[o]c(cc(cc7)N(c(cc8)ccc8-c8cc9ccccc9[o]8)c(cc8)cc9c8-c8ccccc8C9(C)C)c7c6c5[o]5)c5ccc3[o]4)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c(cc3)ccc3-c3cc4ccccc4[o]3)c(cc3)cc4c3c3c(c5ccc6[o]c(cc(cc7)N(c(cc8)ccc8-c8cc9ccccc9[o]8)c(cc8)cc9c8-c8ccccc8C9(C)C)c7c6c5[o]5)c5ccc3[o]4)c2-c2c1cccc2 PWNSHUNKRFETOH-UHFFFAOYSA-N 0.000 description 1
- CIERLRAJKVLTPP-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c(cc3)ccc3[Si](c3ccccc3)(c3ccccc3)c3ccccc3)c(cc3)cc4c3c3c5[o]c6ccc7[o]c(cc(cc8)N(c(cc9)ccc9[Si+](c9ccccc9)(c9ccccc9)c9ccccc9)c(cc9)cc%10c9-c9ccccc9C%10(C)C)c8c7c6c5ccc3[o]4)c2-c2ccccc12 Chemical compound CC1(C)c(cc(cc2)N(c(cc3)ccc3[Si](c3ccccc3)(c3ccccc3)c3ccccc3)c(cc3)cc4c3c3c5[o]c6ccc7[o]c(cc(cc8)N(c(cc9)ccc9[Si+](c9ccccc9)(c9ccccc9)c9ccccc9)c(cc9)cc%10c9-c9ccccc9C%10(C)C)c8c7c6c5ccc3[o]4)c2-c2ccccc12 CIERLRAJKVLTPP-UHFFFAOYSA-N 0.000 description 1
- JXYDPXAIESJUEV-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c3ccc4c(c5c(cc6)[o]c7c(c(ccc(N(c(cc8C9(C)C)ccc8-c8c9cccc8)c8cccc9c8[o]c8ccccc98)c8)c8[o]8)c8ccc57)c6[o]c4c3)c3cccc4c3[o]c3c4cccc3)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c3ccc4c(c5c(cc6)[o]c7c(c(ccc(N(c(cc8C9(C)C)ccc8-c8c9cccc8)c8cccc9c8[o]c8ccccc98)c8)c8[o]8)c8ccc57)c6[o]c4c3)c3cccc4c3[o]c3c4cccc3)c2-c2c1cccc2 JXYDPXAIESJUEV-UHFFFAOYSA-N 0.000 description 1
- RGBHIIOBMUXXEH-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c3ccccc3)c(cc3)cc4c3c(c3c(cc5)[o]c6c3ccc3c6c(ccc(N(c6ccccc6)c(cc6)cc(C7(C)C)c6-c6c7cccc6)c6)c6[o]3)c5[o]4)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c3ccccc3)c(cc3)cc4c3c(c3c(cc5)[o]c6c3ccc3c6c(ccc(N(c6ccccc6)c(cc6)cc(C7(C)C)c6-c6c7cccc6)c6)c6[o]3)c5[o]4)c2-c2c1cccc2 RGBHIIOBMUXXEH-UHFFFAOYSA-N 0.000 description 1
- OVNHBDPZBGFZFK-UHFFFAOYSA-N CC1(C)c(cc(cc2)N(c3ccncc3)c(cc3)cc4c3c(c3c(cc5)[o]c6c(c(ccc(N(c7ccncc7)c(cc7C8(C)C)ccc7-c7c8cccc7)c7)c7[o]7)c7ccc36)c5[o]4)c2-c2c1cccc2 Chemical compound CC1(C)c(cc(cc2)N(c3ccncc3)c(cc3)cc4c3c(c3c(cc5)[o]c6c(c(ccc(N(c7ccncc7)c(cc7C8(C)C)ccc7-c7c8cccc7)c7)c7[o]7)c7ccc36)c5[o]4)c2-c2c1cccc2 OVNHBDPZBGFZFK-UHFFFAOYSA-N 0.000 description 1
- OXWXGMUGQLBDMX-UHFFFAOYSA-N CC1(C)c2cc(N(c3ccc(c(c([o]4)c5)cc([o]c6c7)c5c6cc5c7c(ccc(N(c(cc6)cc7c6-c6ccccc6C7(C)C)c6cc(cccc7)c7cc6)c6)c6[o]5)c4c3)c3cc(cccc4)c4cc3)ccc2-c2ccccc12 Chemical compound CC1(C)c2cc(N(c3ccc(c(c([o]4)c5)cc([o]c6c7)c5c6cc5c7c(ccc(N(c(cc6)cc7c6-c6ccccc6C7(C)C)c6cc(cccc7)c7cc6)c6)c6[o]5)c4c3)c3cc(cccc4)c4cc3)ccc2-c2ccccc12 OXWXGMUGQLBDMX-UHFFFAOYSA-N 0.000 description 1
- BVGVWCDUQMQILS-UHFFFAOYSA-N CCC(C)c(cc1)ccc1-c(cc1)ccc1N(c(cc1)cc2c1-c1ccccc1C2(c1ccccc1)c1ccccc1)c1ccc(c(c([o]2)c3)cc([o]c4c5)c3c4cc([o]c3c4)c5c3ccc4N(c(cc3)ccc3-c3ccc(C(C)CC)cc3)c(cc3)cc(C4(c5ccccc5)c5ccccc5)c3-c3c4cccc3)c2c1 Chemical compound CCC(C)c(cc1)ccc1-c(cc1)ccc1N(c(cc1)cc2c1-c1ccccc1C2(c1ccccc1)c1ccccc1)c1ccc(c(c([o]2)c3)cc([o]c4c5)c3c4cc([o]c3c4)c5c3ccc4N(c(cc3)ccc3-c3ccc(C(C)CC)cc3)c(cc3)cc(C4(c5ccccc5)c5ccccc5)c3-c3c4cccc3)c2c1 BVGVWCDUQMQILS-UHFFFAOYSA-N 0.000 description 1
- MODMXCDYQPAHRN-VGMSBNRJSA-N CCC1OC(CC)C(C[C@@H]2c(cccc3)c3OC2)C1 Chemical compound CCC1OC(CC)C(C[C@@H]2c(cccc3)c3OC2)C1 MODMXCDYQPAHRN-VGMSBNRJSA-N 0.000 description 1
- YZDGROPVYQGZTK-SSDOTTSWSA-N C[C@H]1c2ccccc2OC1 Chemical compound C[C@H]1c2ccccc2OC1 YZDGROPVYQGZTK-SSDOTTSWSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- HCIODZKJMXXMHC-UHFFFAOYSA-N Cc1ccc(c2cc(Oc(cc3)cc4c3[o]c3cc(Cl)ccc43)ccc2[o]2)c2c1 Chemical compound Cc1ccc(c2cc(Oc(cc3)cc4c3[o]c3cc(Cl)ccc43)ccc2[o]2)c2c1 HCIODZKJMXXMHC-UHFFFAOYSA-N 0.000 description 1
- FXAYUHQJGPHEIX-UHFFFAOYSA-N Cc1cccc(-c2cc(N(c(cc3C4(c5ccccc5)c5ccccc5)ccc3-c3c4cccc3)c3ccc(c(cc4[o]c(cc(c(c([o]5)c6)ccc6N(c(cc6)cc7c6-c6ccccc6C7(c6ccccc6)c6ccccc6)c6cccc(-c7cc(C)ccc7)c6)c5c5)c5c4c4)c4[o]4)c4c3)ccc2)c1 Chemical compound Cc1cccc(-c2cc(N(c(cc3C4(c5ccccc5)c5ccccc5)ccc3-c3c4cccc3)c3ccc(c(cc4[o]c(cc(c(c([o]5)c6)ccc6N(c(cc6)cc7c6-c6ccccc6C7(c6ccccc6)c6ccccc6)c6cccc(-c7cc(C)ccc7)c6)c5c5)c5c4c4)c4[o]4)c4c3)ccc2)c1 FXAYUHQJGPHEIX-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
- AHRRDRALUMKRCB-UHFFFAOYSA-N Clc1ccc(c(cc(c(c2c3)c4)[o]c2cc2c3[o]c3cc(Cl)ccc23)c4[o]2)c2c1 Chemical compound Clc1ccc(c(cc(c(c2c3)c4)[o]c2cc2c3[o]c3cc(Cl)ccc23)c4[o]2)c2c1 AHRRDRALUMKRCB-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- 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
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003974 aralkylamines Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005165 aryl thioxy group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- GQVWHWAWLPCBHB-UHFFFAOYSA-L beryllium;benzo[h]quinolin-10-olate Chemical compound [Be+2].C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21.C1=CC=NC2=C3C([O-])=CC=CC3=CC=C21 GQVWHWAWLPCBHB-UHFFFAOYSA-L 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229920001400 block copolymer Polymers 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
- 125000001246 bromo group Chemical group Br* 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
- RVOWEGBJQYOMSG-UHFFFAOYSA-N c1c(-c(cc2)cc(cc3)c2cc3Nc(cc2C3(c4ccccc4)c4ccccc4)ccc2-c2c3cccc2)[o]c2c1cccc2 Chemical compound c1c(-c(cc2)cc(cc3)c2cc3Nc(cc2C3(c4ccccc4)c4ccccc4)ccc2-c2c3cccc2)[o]c2c1cccc2 RVOWEGBJQYOMSG-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- 238000004440 column chromatography Methods 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 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
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 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
- 238000005137 deposition process Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 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
- 239000001177 diphosphate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 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
- 230000005283 ground state Effects 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
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 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
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 239000012535 impurity Substances 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002964 pentacenes Chemical class 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
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical group [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000007774 positive electrode material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007650 screen-printing Methods 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
- 229910052710 silicon Inorganic materials 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 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
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 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
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000008096 xylene Substances 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
-
- H01L51/0052—
-
- H01L51/0061—
-
- H01L51/0072—
-
- H01L51/0073—
-
- H01L51/0094—
-
- H01L51/5012—
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present invention relates to a novel compound and an organic light emitting device comprising the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각, 우수한 콘트라스트, 빠른 응답 시간을 가지며, 휘도, 구동 전압 및 응답 속도 특성이 우수하여 많은 연구가 진행되고 있다. In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물층을 포함하는 구조를 가진다. 상기 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.The development of new materials for organic materials used in organic light emitting devices as described above is continuously required.
한편, 최근에는 공정 비용 절감을 위하여 기존의 증착 공정 대신 용액 공정, 특히 잉크젯 공정을 이용한 유기 발광 소자가 개발되고 있다. 초창기에는 모든 유기 발광 소자 층을 용액 공정으로 코팅하여 유기 발광 소자를 개발하려 하였으나 현재 기술로는 한계가 있어, 정구조 형태에서 HIL, HTL, EML만을 용액 공정으로 진행하고 추후 공정은 기존의 증착 공정을 활용하는 하이브리드(hybrid) 공정이 연구 중이다. Meanwhile, in order to reduce process costs, an organic light emitting diode using a solution process, particularly an inkjet process, has been developed instead of a conventional deposition process. In the early days, it was attempted to develop an organic light emitting device by coating all organic light emitting device layers with a solution process, but current technology has limitations. A hybrid process using
이에 본 발명에서는 유기 발광 소자에 사용될 수 있으면서 동시에 용액 공정에 사용 가능한 신규한 유기 발광 소자의 소재를 제공한다.Accordingly, the present invention provides a novel material for an organic light emitting device that can be used in an organic light emitting device and can be used in a solution process at the same time.
본 발명은 신규한 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present invention relates to a novel compound and an organic light emitting device comprising the same.
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다: The present invention provides a compound represented by the following formula (1):
[화학식 1] [Formula 1]
상기 화학식 1에서,In Formula 1,
A1 및 A2는 각각 인접한 두 개의 오각 고리와 융합된 벤젠 고리이고,A 1 and A 2 are each a benzene ring fused with two adjacent pentagonal rings,
Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고, Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
Ar3 및 Ar4는 각각 독립적으로, 하기 화학식 2 또는 화학식 3으로 표시되고, Ar 3 and Ar 4 are each independently represented by Formula 2 or Formula 3,
[화학식 2][Formula 2]
[화학식 3][Formula 3]
상기 화학식 2 및 화학식 3에서,In Formula 2 and Formula 3,
B1 및 B2는 각각 독립적으로, 인접한 오각 고리와 융합된 C6-60 방향족 고리; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로방향족 고리이고, 단, B1 및 B2는 각각 인접한 오각 고리와 융합되는 벤젠 고리를 포함하고,B 1 and B 2 are each independently a C 6-60 aromatic ring fused to an adjacent pentacyclic ring; Or a C 2-60 heteroaromatic ring containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S, provided that B 1 and B 2 are each fused with an adjacent pentacyclic ring a benzene ring;
R1 및 R2는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 C6-60 알킬; 또는 치환 또는 비치환된 C6-60 아릴이거나, 또는 R1 및 R2는 서로 연결되어 C3-60의 사이클로알칸 고리를 형성하고, R 1 and R 2 are each independently hydrogen; heavy hydrogen; substituted or unsubstituted C 6-60 alkyl; or substituted or unsubstituted C 6-60 aryl, or R 1 and R 2 are linked to each other to form a C 3-60 cycloalkane ring,
L은 단일 결합; O; 또는 Si(R3)(R4)이고,L is a single bond; O; or Si(R 3 )(R 4 ),
R3 내지 R4는 각각 독립적으로, 수소; 중수소; 또는 C1-10 알킬이다.R 3 to R 4 are each independently hydrogen; heavy hydrogen; or C 1-10 alkyl.
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층을 포함하는 유기 발광 소자로서, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and an emission layer provided between the first electrode and the second electrode, wherein the emission layer includes the compound represented by
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있으며, 또한 용액 공정에 사용이 가능하며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. The compound represented by Chemical Formula 1 described above can be used as a material for an organic material layer of an organic light emitting device, and can also be used in a solution process, and can improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device. have.
도 1은 기판(1), 양극(2), 유기물층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.
도 2는 기판(1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8), 전자주입층(9) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. FIG. 1 shows an example of an organic light emitting device including a
2 shows a
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, it will be described in more detail to help the understanding of the present invention.
(용어의 정의)(Definition of Terms)
본 명세서에서, 또는 는 다른 치환기에 연결되는 결합을 의미한다.In this specification, or means a bond connected to another substituent.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로아릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 비페닐기일 수 있다. 즉, 비페닐이기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수도 있다.As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; Or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more, or substituted or unsubstituted with two or more substituents of the above-exemplified substituents connected . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably from 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
본 명세서에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. However, the present invention is not limited thereto.
본 명세서에 있어서, 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸-부틸, 1-에틸-부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸-2-펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 사이클로펜틸메틸, 사이클로헥틸메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸-프로필, 1,1-디메틸-프로필, 이소헥실, 2-메틸펜틸, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 사이클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필, 사이클로부틸, 사이클로펜틸, 3-메틸사이클로펜틸, 2,3-디메틸사이클로펜틸, 사이클로헥실, 3-메틸사이클로헥실, 4-메틸사이클로헥실, 2,3-디메틸사이클로헥실, 3,4,5-트리메틸사이클로헥실, 4-tert-부틸사이클로헥실, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 비페닐이기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난쓰레닐기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, etc. can be However, the present invention is not limited thereto.
본 명세서에 있어서, 헤테로아릴은 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로아릴로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로아릴의 예로는 잔텐(xanthene), 티오잔텐(thioxanthen), 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino Pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group ( phenanthroline), an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기, 아릴실릴기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서, 아르알킬기, 알킬아릴기, 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서, 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 탄화수소 고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로아릴에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group is the same as the examples of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group. In the present specification, as for heteroaryl among heteroarylamines, the description regarding heteroaryl described above may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group. In the present specification, the description of the above-described aryl group may be applied except that arylene is a divalent group. In the present specification, the description of heteroaryl described above may be applied, except that heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents. In the present specification, the heterocycle is not a monovalent group, and the description of the above-described heteroaryl may be applied, except that it is formed by combining two substituents.
(화합물)(compound)
본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. The present invention provides a compound represented by the above formula (1).
상기 화학식 1로 표시되는 화합물은 디벤조퓨란 및 벤조퓨란의 융합고리를 코어로 하고, 2 이상의 아민 치환기를 가지며, 각각의 아민 치환기에 적어도 1 이상의 플루오렌 유도체가 포함되는 구조를 갖는다. The compound represented by
이와 같은 구조로 인하여 화학식 1의 화합물은 우수한 용해도를 나타내어 용액 공정에 적합하게 사용될 수 있으며 유기발광소자의 유기물층, 바람직하게 발광층의 도펀트로 사용될 수 있고, 이 경우 향상된 수명 및 효율을 나타낼 수 있다.Due to such a structure, the compound of
바람직하게는, 상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 또는 화학식 1-2로 표시될 수 있다:Preferably, the compound represented by
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
상기 화학식 1-1 및 화학식 1-2에서 Ar1 내지 Ar4는 화학식 1에서 정의한 바와 같다.In Formulas 1-1 and 1-2, Ar 1 to Ar 4 are as defined in
바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-30 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-30 헤테로아릴이다.Preferably, Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted C 6-30 aryl; or C 2-30 heteroaryl including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
바람직하게는, Ar1 및 Ar2는 각각 독립적으로, 하기로 이루어지는 군으로부터 선택되는 어느 하나이다:Preferably, Ar 1 and Ar 2 are each independently any one selected from the group consisting of:
상기에서,above,
X1 내지 X5는 각각 독립적으로, CR'1 또는 N이고,X 1 To X 5 are each independently, CR' 1 or N,
R'1은 각각 독립적으로, 수소; 할로겐; C1-10 알킬; C1-10 알콕시; C6-20 아릴옥시; C1-10 알킬아미노; C6-20 아릴아미노; C1-10 알킬실릴; C6-20 아릴실릴; C6-20 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,R' 1 are each independently hydrogen; halogen; C 1-10 alkyl; C 1-10 alkoxy; C 6-20 aryloxy; C 1-10 alkylamino; C 6-20 arylamino; C 1-10 alkylsilyl; C 6-20 arylsilyl; C 6-20 aryl; or C 2-20 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S;
X6는 NR'2, C(R'3)(R'4), O, 또는 S이고,X 6 is NR′ 2 , C(R′ 3 )(R′ 4 ), O, or S;
R'2 내지 R'4는 각각 독립적으로, 수소; C1-10 알킬; C6-20 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,R' 2 To R' 4 are each independently hydrogen; C 1-10 alkyl; C 6-20 aryl; or C 2-20 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S;
p는 0 내지 7의 정수이고,p is an integer from 0 to 7,
R'5는 각각 독립적으로, 수소; C1-10 알킬; C6-20 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이다.R' 5 are each independently hydrogen; C 1-10 alkyl; C 6-20 aryl; or C 2-20 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.
상기에서, C1-10 알킬은 메틸 또는 t-부틸일 수 있다.In the above, C 1-10 alkyl may be methyl or t-butyl.
상기에서, C6-20 아릴옥시는 페녹시일 수 있다.In the above, C 6-20 aryloxy may be phenoxy.
상기에서, C1-10 알킬아미노는 디메틸아미노일 수 있고, C6-20 아릴아미노는 디페닐아미노일 수 있다. In the above, C 1-10 alkylamino may be dimethylamino, and C 6-20 arylamino may be diphenylamino.
상기에서, C1-10 알킬실릴은 트리메틸실릴일 수 있고, C6-20 아릴실릴은 트리페닐실릴일 수 있다.In the above, C 1-10 alkylsilyl may be trimethylsilyl, and C 6-20 arylsilyl may be triphenylsilyl.
상기에서, C6-20 아릴은 치환 또는 비치환될 수 있고, 예를 들어 나프틸 또는 t-부틸페닐일 수 있다.In the above, C 6-20 aryl may be substituted or unsubstituted, for example, naphthyl or t-butylphenyl.
상기에서, N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴은 치환 또는 비치환될 수 있고, 예를 들어 카바졸릴 또는 벤조퓨라닐일 수 있다. In the above, C 2-20 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S may be substituted or unsubstituted, for example, carbazolyl or benzofuranyl.
바람직하게는 Ar1 및 Ar2는 각각 독립적으로, 페닐, 비페닐, 터페닐, 나프틸, 나프틸페닐, 페닐나프틸, 피리디닐, 벤조퓨라닐, 벤조티오페닐, 디메틸플루오레닐, 디페닐플루오레닐, 디벤조퓨라닐, 디벤조티오페닐, 닐카바졸릴이고, 상기 Ar1 및 Ar2는 각각 독립적으로, 비치환되거나, 또는 메틸, 이소프로필, sec-부틸, t-부틸, 1,1,3,3-테트라메틸부틸, t-부틸페닐, 나프틸, 트리페닐실릴, 디메틸아미노, 디페닐아미노, 플루오로, 페녹시, 카바졸릴, 및 벤조퓨라닐로 구성되는 군으로부터 선택되는 하나 또는 두 개의 치환기로 치환된다.Preferably, Ar 1 and Ar 2 are each independently phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, pyridinyl, benzofuranyl, benzothiophenyl, dimethylfluorenyl, diphenyl fluorenyl, dibenzofuranyl, dibenzothiophenyl, nylcarbazolyl, wherein Ar 1 and Ar 2 are each independently, unsubstituted, or methyl, isopropyl, sec-butyl, t-butyl, 1, one selected from the group consisting of 1,3,3-tetramethylbutyl, t-butylphenyl, naphthyl, triphenylsilyl, dimethylamino, diphenylamino, fluoro, phenoxy, carbazolyl, and benzofuranyl or two substituents.
바람직하게는, Ar1 및 Ar2는 서로 동일할 수 있다.Preferably, Ar 1 and Ar 2 may be the same as each other.
상기 화학식 2 및 화학식 3에서, B1 및 B2는 각각 인접한 오각 고리와 융합되는 벤젠 고리를 포함한다. 즉, 화학식 2 및/또는 화학식 3에서 부분은 플루오렌 모이어티를 포함하며, B1 또는 B2가 벤젠 이외의 아릴이거나 헤테로아릴일 경우, 부분은 플루오렌에 융합된 고리를 더 포함하는 구조이다.In
바람직하게는, B1 및 B2는 각각 인접한 오각 고리와 융합된 C6-30 방향족 고리; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-30 헤테로방향족 고리이다. Preferably, B 1 and B 2 are each a C 6-30 aromatic ring fused with an adjacent pentacyclic ring; Or a C 2-30 heteroaromatic ring containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
바람직하게는, B1 내지 B4는 각각 독립적으로, 인접한 오각 고리와 융합된 벤젠; 나프탈렌; 페난트렌; 또는 디벤조퓨란이다. 이 경우, 화학식 2 및/또는 화학식 3의 부분은 각각 독립적으로 하기로 이루어지는 군에서 선택되는 어느 하나일 수 있다:Preferably, B 1 to B 4 are each independently benzene fused to an adjacent pentacyclic ring; naphthalene; phenanthrene; or dibenzofuran. In this case,
바람직하게는, Ar3 및 Ar4는 각각 독립적으로 하기로 이루어지는 군에서 선택되는 어느 하나일 수 있다:Preferably, Ar 3 and Ar 4 may each independently be any one selected from the group consisting of:
상기에서, R1 및 R2는 화학식 2에서 정의한 바와 같고, L은 화학식 3에서 정의한 바와 같다.In the above, R 1 and R 2 are as defined in
바람직하게는, R1 및 R2는 치환 또는 비치환된 C1-30 알킬; 치환 또는 비치환된 C6-30 아릴이거나, 또는 R1 및 R2는 서로 연결되어 C3-30의 사이클로알칸 고리를 형성한다.Preferably, R 1 and R 2 are substituted or unsubstituted C 1-30 alkyl; substituted or unsubstituted C 6-30 aryl, or R 1 and R 2 are linked to each other to form a C 3-30 cycloalkane ring.
바람직하게는, R1 및 R2는 각각 독립적으로, 메틸; 페닐; 메틸페닐; 또는 t-부틸페닐이거나, 또는 R1 및 R2가 서로 연결되어 사이클로헥산고리를 형성한다. Preferably, R 1 and R 2 are each independently methyl; phenyl; methylphenyl; or t-butylphenyl, or R 1 and R 2 are connected to each other to form a cyclohexane ring.
바람직하게는, L은 단일 결합, O, 또는 Si(CH3)2이다.Preferably, L is a single bond, O, or Si(CH 3 ) 2 .
바람직하게는, Ar3 및 Ar4는 서로 동일할 수 있다.Preferably, Ar 3 and Ar 4 may be the same as each other.
상기 화학식 1로 표시되는 화합물의 대표적인 예는 하기와 같다:Representative examples of the compound represented by
한편, 본 발명은 상기 화학식 1로 표시되는 화합물의 제조방법을 제공한다. 일례로, 화학식 1의 화합물은 하기 반응식 1과 같은 제조방법으로 제조될 수 있다:On the other hand, the present invention provides a method for preparing the compound represented by the above formula (1). For example, the compound of
[반응식 1] [Scheme 1]
상기 반응식 1에서, X'을 제외한 나머지 정의는 앞서 정의한 바와 같으며, X'은 할로겐이고, 바람직하게는 클로로 또는 브로모이다.In
상기 반응식 1은 아민 치환 반응으로서, 팔라듐 촉매와 염기 존재 하에 수행하는 것이 바람직하며, 아민 치환 반응을 위한 반응기는 당업계에 알려진 바에 따라 변경이 가능하다.
상기 제조 방법은 후술할 제조예에서 보다 구체화될 수 있다.The manufacturing method may be more specific in Preparation Examples to be described later.
(코팅 조성물)(Coating composition)
한편, 본 발명에 따른 화합물은 용액 공정으로 유기 발광 소자의 유기물 층, 특히 발광층을 형성할 수 있다. 구체적으로, 상기 화합물은 발광층의 도펀트 재료로 사용될 수 있다. 이를 위하여, 본 발명은 상술한 본 발명에 따른 화합물 및 용매를 포함하는 코팅 조성물을 제공한다. On the other hand, the compound according to the present invention can form an organic material layer, particularly, a light emitting layer of an organic light emitting device by a solution process. Specifically, the compound may be used as a dopant material of the emission layer. To this end, the present invention provides a coating composition comprising the above-described compound according to the present invention and a solvent.
상기 용매는 본 발명에 따른 화합물을 용해 또는 분산시킬 수 있는 용매이면 특별히 제한되지 않으며, 일례로 클로로포름, 염화메틸렌, 1,2-디클로로에탄, 1,1,2-트리클로로에탄, 클로로벤젠, o-디클로로벤젠 등의 염소계 용매; 테트라하이드로퓨란, 디옥산 등의 에테르계 용매; 톨루엔, 크실렌, 트리메틸벤젠, 메시틸렌 등의 방향족 탄화수소계 용매; 시클로헥산, 메틸시클로헥산, n-펜탄, n-헥산, n-헵탄, n-옥탄, n-노난, n-데칸 등의 지방족 탄화수소계 용매; 아세톤, 메틸에틸케톤, 시클로헥사논 등의 케톤계 용매; 아세트산에틸, 아세트산부틸, 에틸셀로솔브아세테이트 등의 에스테르계 용매; 에틸렌글리콜, 에틸렌글리콜모노부틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노메틸에테르, 디메톡시에탄, 프로필렌글리콜, 디에톡시메탄, 트리에틸렌글리콜모노에틸에테르, 글리세린, 1,2-헥산디올 등의 다가 알코올 및 그의 유도체; 메탄올, 에탄올, 프로판올, 이소프로판올, 시클로헥산올 등의 알코올계 용매; 디메틸술폭사이드 등의 술폭사이드계 용매; 및 N-메틸-2-피롤리돈, N,N-디메틸포름아미드 등의 아미드계 용매; 부틸벤조에이트, 메틸-2-메톡시벤조에이트 등의 벤조에이트계 용매; 테트랄린; 3-페녹시톨루엔 등의 용매를 들 수 있다. 또한, 상술한 용매를 1종 단독으로 사용하거나 2종 이상의 용매를 혼합하여 사용할 수 있다. 바람직하게는 상기 용매로 톨루엔을 사용할 수 있다. The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention, and for example, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o - Chlorine solvents, such as dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol alcohols and derivatives thereof; alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butyl benzoate and methyl-2-methoxy benzoate; tetralin; and solvents such as 3-phenoxytoluene. In addition, the above-mentioned solvents may be used alone or as a mixture of two or more solvents. Preferably, toluene may be used as the solvent.
또한, 상기 코팅 조성물은 호스트 재료로 사용되는 화합물을 더 포함할 수 있고, 상기 호스트 재료에 사용되는 화합물에 대한 설명은 후술한다.In addition, the coating composition may further include a compound used as a host material, and a description of the compound used for the host material will be described later.
또한, 상기 코팅 조성물의 점도는 1 cP 내지 10 cP가 바람직하며, 상기의 범위에서 코팅이 용이하다. 또한, 상기 코팅 조성물 내 본 발명에 따른 화합물의 농도는 0.1 wt/v% 내지 20 wt/v%인 것이 바람직하다. In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy in the above range. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt/v% to 20 wt/v%.
또한, 본 발명은 상술한 코팅 조성물을 사용하여 발광층을 형성하는 방법을 제공한다. 구체적으로, 양극 상에, 또는 양극 상에 형성된 정공 수송층 상에 상술한 본 발명에 따른 발광층을 용액 공정으로 코팅하는 단계; 및 상기 코팅된 코팅 조성물을 열처리하는 단계를 포함한다. In addition, the present invention provides a method of forming a light emitting layer using the above-described coating composition. Specifically, coating the light emitting layer according to the present invention on the anode or on the hole transport layer formed on the anode in a solution process; and heat-treating the coated coating composition.
상기 용액 공정은 상술한 본 발명에 따른 코팅 조성물을 사용하는 것으로, 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The solution process uses the coating composition according to the present invention described above, and refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
상기 열처리 단계에서 열처리 온도는 150 내지 230℃가 바람직하다. 또한, 상기 열처리 시간은 1분 내지 3시간이고, 보다 바람직하게는 10분 내지 1시간이다. 또한, 상기 열처리는 아르곤, 질소 등의 불활성 기체 분위기에서 수행하는 것이 바람직하다. The heat treatment temperature in the heat treatment step is preferably 150 to 230 ℃. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.
(유기 발광 소자)(organic light emitting element)
또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층을 포함하는 유기 발광 소자로서, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.In addition, the present invention provides an organic light emitting device including the compound represented by the formula (1). In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and an emission layer provided between the first electrode and the second electrode, wherein the emission layer includes the compound represented by
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. 예컨대, 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다.Also, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Also, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .
도 1은 기판(1), 양극(2), 유기물층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 유기물층에 포함될 수 있다. FIG. 1 shows an example of an organic light emitting device including a
도 2는 기판(1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8), 전자주입층(9) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다.2 shows a
본 발명에 따른 유기 발광 소자는, 상기 발광층이 본 발명에 따른 화합물을 포함하고, 상술한 방법과 같이 제조되는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조할 수 있다.The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that the light emitting layer includes the compound according to the present invention and is manufactured as described above.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 양극, 유기물층 및 음극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다(WO 2003/012890). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
일례로, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이거나, 또는 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다.In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SNO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 화합물 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SNO 2 :Sb; conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
상기 정공주입층은 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 화합물 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect with respect to the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive compounds, and the like, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 화합물, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material that can transport holes from the anode or the hole injection layer to the light emitting layer and transfer them to the light emitting layer. material is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion together.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 도펀트 재료로는 상술한 화학식 1로 표시되는 화합물이 사용될 수 있다. 또한, 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등을 사용할 수 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. The emission layer may include a host material and a dopant material. As the dopant material, the compound represented by the above-described
상기 전자 주입 및 수송층은 전극으로부터 전자를 주입하고, 수취된 전자를 발광층까지 수송하는 전자수송층 및 전자주입층의 역할을 동시에 수행하는 층으로, 상기 발광층 또는 상기 전자조절층 상에 형성된다. 이러한 전자 주입 및 수송물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 전자 주입 및 수송물질의 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물; 트리아진 유도체 등이 있으나, 이들에만 한정되는 것은 아니다. 또는 LiF, NaF, NaCl, CsF, Li2O, BaO, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물, 또는 질소 함유 5원환 유도체 등을 사용할 수도 있으나, 이에 한정되는 것은 아니다. The electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from the electrode and transporting the received electrons to the emission layer, and is formed on the emission layer or the electron control layer. As the electron injection and transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Examples of specific electron injection and transport materials include Al complex of 8-hydroxyquinoline; complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives, but is not limited thereto. or LiF, NaF, NaCl, CsF, Li 2 O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, pre Orenylidene methane, anthrone, etc. derivatives thereof, metal complex compounds, or nitrogen-containing 5-membered ring derivatives may be used, but the present invention is not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.
또한, 본 발명에 따른 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며, 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다.The compound represented by
[합성예][Synthesis Example]
합성예 1: 화합물 BD1의 제조Synthesis Example 1: Preparation of compound BD1
합성예 1-1) 중간체 1의 제조Synthesis Example 1-1) Preparation of
질소 분위기에서 500 mL 둥근바닥 플라스크에 3,7-디브로모벤젠[b,d]퓨란-2,8-디올 (14.3 g, 40 mmol), (4-클로로-2-플루오로페닐)보론산 (16.5 g, 48 mmol), 테트라키스(트리페닐포스핀)팔라듐 (2.3 g, 2 mmol), 포타슘카보네이트 (16.6 g, 60 mmol)을 넣고 테트라하이드로퓨란 300 mL, 물 60 mL를 넣었다. 반응기의 온도를 80 oC로 승온시키고 12 시간 교반시켰다. 반응이 종료되면 실온으로 낮추고 유기층을 추출하였다. 얻어진 유기층을 농축시킨 후 헥산/에틸아세테이트 크로마토그래피 분리법을 이용해 중간체 1을 (15.3 g, 수율 84 %)수득하였다.3,7-dibromobenzene [b, d] furan-2,8-diol (14.3 g, 40 mmol), (4-chloro-2-fluorophenyl) boronic acid in a 500 mL round-bottom flask under nitrogen atmosphere (16.5 g, 48 mmol), tetrakis (triphenylphosphine) palladium (2.3 g, 2 mmol), potassium carbonate (16.6 g, 60 mmol) were added, and tetrahydrofuran 300 mL and water 60 mL were added. The temperature of the reactor was raised to 80 o C and stirred for 12 hours. When the reaction was completed, the temperature was lowered to room temperature and the organic layer was extracted. After the obtained organic layer was concentrated, intermediate 1 (15.3 g, yield 84%) was obtained by hexane/ethyl acetate chromatography separation method.
합성예 1-2) 중간체 2의 제조Synthesis Example 1-2) Preparation of
질소 분위기에서 500 mL 둥근바닥 플라스크에 중간체 1 (15.3 g, 33.6 mmol), 포타슘카보네이트 (10.2 g, 74 mmol)을 넣고 N-메틸-2-피롤리돈 180 mL를 넣었다. 반응기의 온도를 120 oC로 승온시키고 4 시간 교반시켰다. 반응이 종료된 후 온도를 실온으로 낮추고 물을 넣어 고체를 석출시켜 여과시킨 후 에탄올과 테트라하이드로퓨란으로 씻어주어 불순물을 제거하고 중간체 2를 (9.3 g, 수율 66 %)수득하였다.Intermediate 1 (15.3 g, 33.6 mmol) and potassium carbonate (10.2 g, 74 mmol) were placed in a 500 mL round-bottom flask in a nitrogen atmosphere, and 180 mL of N-methyl-2-pyrrolidone was added. The temperature of the reactor was raised to 120 ° C and stirred for 4 hours. After completion of the reaction, the temperature was lowered to room temperature, water was added to precipitate a solid, filtered, washed with ethanol and tetrahydrofuran to remove impurities, and Intermediate 2 (9.3 g, yield 66%) was obtained.
합성예 1-3) 화합물 BD 1의 제조Synthesis Example 1-3) Preparation of
질소 분위기에서 250 mL 플라스크에 중간체 2 (1.2 g, 3.7 mmol), N-(4-(터트-부틸)페닐)-9,9-디메틸-플루오렌-2-아민 (2.8 g, 8.1 mmol), 비스(트리-터트-뷰틸포스핀)팔라듐(0) (0.23 g, 0.4 mmol), 소듐터트뷰톡사이드 (0.8 g, 8.1 mmol) 및 톨루엔 100 mL를 넣고 105℃에서 16시간 동안 교반하였다. 반응 종료 후, 반응 혼합물을 상온으로 식히고 물을 첨가한 다음, 헥산으로 침전물이 생기게 하였다. 상기 침전물을 여과한 후, 메탄올, 톨루엔으로 세척하여 유기물을 수득하였다. 생성된 유기물은 디클로로메탄에 녹이고 산성 알루미나, 셀라이트 필터를 통과시킨 뒤 농축시켰다. 노르말헥산과 다이클로로메탄을 이용하여 컬럼크로마토그래피 분리법으로 정제한 후 용매를 제거해 화합물 BD 1(2.6 g, 수율 71%)을 얻었다. MS[M+H]+= 999.44Intermediate 2 (1.2 g, 3.7 mmol), N-(4-(tert-butyl)phenyl)-9,9-dimethyl-fluoren-2-amine (2.8 g, 8.1 mmol), in a 250 mL flask under nitrogen atmosphere, Bis(tri-tert-butylphosphine)palladium(0) (0.23 g, 0.4 mmol), sodium tert-butoxide (0.8 g, 8.1 mmol) and 100 mL of toluene were added and stirred at 105° C. for 16 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added, and then a precipitate was formed with hexane. After filtering the precipitate, it was washed with methanol and toluene to obtain an organic material. The resulting organic material was dissolved in dichloromethane, passed through an acid alumina filter and a Celite filter, and then concentrated. After purification by column chromatography separation using normal hexane and dichloromethane, the solvent was removed to obtain compound BD 1 (2.6 g, yield 71%). MS[M+H] + = 999.44
합성예 2: 화합물 BD 2의 제조Synthesis Example 2: Preparation of
합성예 1-3에서 N-(4-(터트-부틸)페닐)-9,9-디메틸-플루오렌-2-아민 대신 9,9-디메틸-N-(2-나프틸)-플루오렌-2-아민을 사용한 것을 제외하고는 상기 화합물 BD 1의 제조 방법과 동일한 방법으로 화합물 BD 2 (2.3 g, 수율 67 %)를 얻었다. MS[M+H]+= 1015.38In Synthesis Example 1-3, 9,9-dimethyl-N-(2-naphthyl)-fluorene- instead of N-(4-(tert-butyl)phenyl)-9,9-dimethyl-fluoren-2-amine Compound BD 2 (2.3 g, yield 67%) was obtained in the same manner as in the preparation of
합성예 3: 화합물 BD 3의 제조Synthesis Example 3: Preparation of
합성예 1-3에서 N-(4-(터트-부틸)페닐)-9,9-디메틸-플루오렌-2-아민 대신 비스(9,9-디메틸플루오렌)-2-아민을 사용한 것을 제외하고는 상기 화합물 BD 1의 제조 방법과 동일한 방법으로 화합물 BD 3 (2.7 g, 수율 60 %)를 얻었다. MS[M+H]+= 1119.44Except for using bis(9,9-dimethylfluorene)-2-amine instead of N-(4-(tert-butyl)phenyl)-9,9-dimethyl-fluoren-2-amine in Synthesis Example 1-3 Then, compound BD 3 (2.7 g, yield 60%) was obtained in the same manner as in the preparation method of
합성예 4: 화합물 BD 5의 제조Synthesis Example 4: Preparation of
합성예 1-3에서 N-(4-(터트-부틸)페닐)-9,9-디메틸-플루오렌-2-아민 대신 N-(4-(벤조퓨란-2-)페닐)-9,9-디메틸플루오렌-2-아민을 사용한 것을 제외하고는 상기 화합물 BD 1의 제조 방법과 동일한 방법으로 화합물 BD 4 (2. g, 수율 61 %)를 얻었다. MS[M+H]+= 1147.40In Synthesis Example 1-3, N-(4-(benzofuran-2-)phenyl)-9,9 instead of N-(4-(tert-butyl)phenyl)-9,9-dimethyl-fluoren-2-amine - Compound BD 4 (2. g, yield 61%) was obtained in the same manner as in the preparation of
합성예 5) 화합물 BD 5의 제조Synthesis Example 5) Preparation of
합성예 1-3에서 N-(4-(터트-부틸)페닐)-9,9-디메틸-플루오렌-2-아민 대신 N-(3-(카바졸-9-)페닐)-9,9-디메틸플루오렌-2-아민을 사용한 것을 제외하고는 상기 화합물 BD 1의 제조 방법과 동일한 방법으로 화합물 BD 5 (1.9 g, 수율 56 %)를 얻었다. MS[M+H]+= 1245.47In Synthesis Example 1-3, N-(3-(carbazole-9-)phenyl)-9,9 instead of N-(4-(tert-butyl)phenyl)-9,9-dimethyl-fluoren-2-amine -Compound BD 5 (1.9 g, yield 56%) was obtained in the same manner as in the preparation of
합성예 6) 화합물 BD 6의 제조Synthesis Example 6) Preparation of
합성예 1-3에서 N-(4-(터트-부틸)페닐)-9,9-디메틸-플루오렌-2-아민 대신 N-(6-(벤조퓨란-2-)나프탈렌-2)-9,9-디페닐플루오렌-2-아민을 사용한 것을 제외하고는 상기 화합물 BD 1의 제조 방법과 동일한 방법으로 화합물 BD 6 (3.1 g, 수율 63 %)를 얻었다. MS[M+H]+= 1495.50In Synthesis Example 1-3, N-(6-(benzofuran-2-)naphthalene-2)-9 instead of N-(4-(tert-butyl)phenyl)-9,9-dimethyl-fluoren-2-amine Compound BD 6 (3.1 g, yield 63%) was obtained in the same manner as in the preparation method of
합성예 7) 화합물 BD 7의 제조Synthesis Example 7) Preparation of
합성예 1-3에서 N-(4-(터트-부틸)페닐)-9,9-디메틸-플루오렌-2-아민 대신 11,11-디메틸-N-(나프탈렌-2)-벤조플루오렌-2-아민을 사용한 것을 제외하고는 상기 화합물 BD 1의 제조 방법과 동일한 방법으로 화합물 BD 7 (1.8 g, 수율 63 %)를 얻었다. MS[M+H]+= 963.28In Synthesis Example 1-3, 11,11-dimethyl-N-(naphthalene-2)-benzofluorene- instead of N-(4-(tert-butyl)phenyl)-9,9-dimethyl-fluoren-2-amine Compound BD 7 (1.8 g, yield 63%) was obtained in the same manner as in the preparation of
합성예 8) 화합물 BD 8의 제조Synthesis Example 8) Preparation of
합성예 1-3에서 N-(4-(터트-부틸)페닐)-9,9-디메틸-플루오렌-2-아민 대신 N-(4’-이소프로필-[1,1’-비페닐]-4)-9,9-디메틸플루오렌-3-아민을 사용한 것을 제외하고는 상기 화합물 BD 1의 제조 방법과 동일한 방법으로 화합물 BD 8 (2.5 g, 수율 65 %)를 얻었다. MS[M+H]+= 1115.41In Synthesis Example 1-3, N-(4'-isopropyl-[1,1'-biphenyl] instead of N-(4-(tert-butyl)phenyl)-9,9-dimethyl-fluoren-2-amine Compound BD 8 (2.5 g, yield 65%) was obtained in the same manner as in the preparation of
[실시예][Example]
실시예 1Example 1
ITO(indium tin oxide)가 1,500 Å의 두께로 박막 증착된 유리 기판을, 세제를 녹인 증류수에 넣고, 30분간 초음파로 세척하였다. 이후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜 및 아세톤의 용제로 초음파 세척을 각각 30분씩 하고 건조시킨 후, 상기 기판을 글러브박스로 수송시켰다. A glass substrate on which indium tin oxide (ITO) was deposited to a thickness of 1,500 Å was placed in distilled water in which detergent was dissolved, and then washed with ultrasonic waves for 30 minutes. Thereafter, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing with a solvent of isopropyl alcohol and acetone was performed for 30 minutes each and dried, and then the substrate was transported to a glove box.
이렇게 준비된 ITO 투명 전극 위에 하기 화합물 A 및 화합물 IB (p-도판트)를 8:2의 중량비로 시클로헥사논(용매)에 2 wt%로 용해시킨 코팅 조성물을 스핀 코팅하여 300 Å 두께의 정공주입층을 형성하고, 질소 분위기 하에 핫플레이트에서 220℃ 및 30분 조건으로 코팅 조성물을 경화시켰다. 상기 정공주입층 상에, 하기 화합물 A를 톨루엔에 1 wt%로 녹인 조성물을 스핀 코팅하여 400 Å 두께의 정공수송층을 형성하였다. 이후, 질소 분위기 하에 핫플레이트에서 230℃ 및 30분 조건으로 코팅 조성물을 경화시켰다. 상기 정공수송층 상에, 하기 화합물 B와 앞서 제조한 화합물 BD 1을 톨루엔에 0.6 wt%로 용해시킨 조성물(화합물 B: 화합물 BD 1의 중량비 = 98:2)을 스핀 코팅하여 200 Å 두께의 발광층을 형성하고, 질소 분위기 하에 핫플레이트에서 120℃ 및 10분 조건으로 코팅 조성물을 경화시켰다. 이후, 진공증착기로 옮겨 상기 발광층 위에 하기 화합물 G(전자수송층, 200 Å), LiF(전자주입층, 12 Å) 및 Al(2000 Å)를 순차적으로 증착하여 유기 발광 소자를 제조하였다. A coating composition in which the following compound A and compound IB (p-dopant) were dissolved in cyclohexanone (solvent) at 2 wt% in a weight ratio of 8:2 on the thus prepared ITO transparent electrode was spin-coated to inject a hole having a thickness of 300 Å A layer was formed, and the coating composition was cured at 220° C. and 30 minutes on a hot plate under a nitrogen atmosphere. On the hole injection layer, a composition obtained by dissolving the following compound A in toluene at 1 wt% was spin-coated to form a hole transport layer having a thickness of 400 Å. Thereafter, the coating composition was cured at 230° C. and 30 minutes on a hot plate under a nitrogen atmosphere. On the hole transport layer, a composition obtained by dissolving the following compound B and the previously
상기의 과정에서 유기물의 증착 속도는 0.4 내지 0.7 Å/sec를 유지하였고, 캐소드의 LiF는 0.3 Å/ sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10-7 내지 5×10-8 torr를 유지하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of LiF of the cathode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2×10 -7 to 5×10 −8 torr were maintained.
실시예 2 내지 8Examples 2 to 8
화합물 BD 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다.An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of
비교예 1 내지 3Comparative Examples 1 to 3
화합물 BD 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는, 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 화합물 C 내지 E는 각각 하기와 같다. An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of
실험예Experimental example
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 대하여, 10 mA/cm2의 전류 밀도에서 구동 전압, 최대 발광파장, 전류 효율, 및 양자 효율을 측정하여 그 결과를 하기 표 1에 나타내었다.For the organic light-emitting devices prepared in Examples and Comparative Examples, the driving voltage, the maximum emission wavelength, the current efficiency, and the quantum efficiency were measured at a current density of 10 mA/cm 2 , and the results are shown in Table 1 below.
(V)drive voltage
(V)
(cd/A)current efficiency
(cd/A)
(%)quantum efficiency
(%)
상기 표 1에 나타난 바와 같이, 본 발명의 화합물을 발광층의 도펀트로 사용한 유기 발광 소자는 구동 전압, 전류 효율 또는 양자 효율 면에서 현저한 효과를 나타내는 것으로 확인되었다.As shown in Table 1, it was confirmed that the organic light emitting device using the compound of the present invention as a dopant of the light emitting layer exhibited remarkable effects in terms of driving voltage, current efficiency, or quantum efficiency.
1: 기판
2: 양극
3: 유기물층
4: 음극
5: 정공주입층
6: 정공수송층
7: 발광층
8: 전자수송층
9: 전자주입층1: Substrate 2: Anode
3: organic layer 4: cathode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: electron transport layer
9: electron injection layer
Claims (11)
[화학식 1]
상기 화학식 1에서,
A1 및 A2는 각각 인접한 두 개의 오각 고리와 융합된 벤젠 고리이고,
Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이고,
Ar3 및 Ar4는 각각 독립적으로, 하기 화학식 2 또는 화학식 3으로 표시되고,
[화학식 2]
[화학식 3]
상기 화학식 2 및 화학식 3에서,
B1 및 B2는 각각 독립적으로, 인접한 오각 고리와 융합된 C6-60 방향족 고리; 또는 치환 또는 비치환된 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로방향족 고리이고, 단, B1 및 B2는 각각 인접한 오각 고리와 융합되는 벤젠 고리를 포함하고,
R1 및 R2는 각각 독립적으로, 수소; 중수소; 치환 또는 비치환된 C6-60 알킬; 또는 치환 또는 비치환된 C6-60 아릴이거나, 또는 R1 및 R2는 서로 연결되어 C3-60의 사이클로알칸 고리를 형성하고,
L은 단일 결합; O; 또는 Si(R3)(R4)이고,
R3 내지 R4는 각각 독립적으로, 수소; 중수소; 또는 C1-10 알킬이다.
A compound represented by the following formula (1):
[Formula 1]
In Formula 1,
A 1 and A 2 are each a benzene ring fused with two adjacent pentagonal rings,
Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-60 aryl; Or substituted or unsubstituted C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
Ar 3 and Ar 4 are each independently represented by Formula 2 or Formula 3,
[Formula 2]
[Formula 3]
In Formula 2 and Formula 3,
B 1 and B 2 are each independently a C 6-60 aromatic ring fused to an adjacent pentacyclic ring; Or a C 2-60 heteroaromatic ring containing at least one heteroatom selected from the group consisting of substituted or unsubstituted N, O and S, provided that B 1 and B 2 are each fused with an adjacent pentacyclic ring a benzene ring;
R 1 and R 2 are each independently hydrogen; heavy hydrogen; substituted or unsubstituted C 6-60 alkyl; or substituted or unsubstituted C 6-60 aryl, or R 1 and R 2 are linked to each other to form a C 3-60 cycloalkane ring,
L is a single bond; O; or Si(R 3 )(R 4 ),
R 3 to R 4 are each independently hydrogen; heavy hydrogen; or C 1-10 alkyl.
상기 화학식 1은 하기 화학식 1-1 또는 화학식 1-2로 표시되는,
화합물:
[화학식 1-1]
[화학식 1-2]
상기 화학식 1-1 및 화학식 1-2에서 Ar1 내지 Ar4는 제1항에서 정의한 바와 같다.
According to claim 1,
Formula 1 is represented by the following Formula 1-1 or Formula 1-2,
compound:
[Formula 1-1]
[Formula 1-2]
In Formulas 1-1 and 1-2, Ar 1 to Ar 4 are as defined in claim 1.
Ar1 및 Ar2는 각각 독립적으로, 하기로 이루어지는 군으로부터 선택되는 어느 하나인,
화합물:
상기에서,
X1 내지 X5는 각각 독립적으로, CR'1 또는 N이고,
R'1은 각각 독립적으로, 수소; 할로겐; C1-10 알킬; C1-10 알콕시; C6-20 아릴옥시; C1-10 알킬아미노; C6-20 아릴아미노; C1-10 알킬실릴; C6-20 아릴실릴; C6-20 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,
X6는 NR'2, C(R'3)(R'4), O, 또는 S이고,
R'2 내지 R'4는 각각 독립적으로, 수소; C1-10 알킬; C6-20 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이고,
p는 0 내지 7의 정수이고,
R'5는 각각 독립적으로, 수소; C1-10 알킬; C6-20 아릴; 또는 N, O 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-20 헤테로아릴이다.
According to claim 1,
Ar 1 and Ar 2 are each independently any one selected from the group consisting of
compound:
above,
X 1 To X 5 are each independently, CR' 1 or N,
R' 1 are each independently hydrogen; halogen; C 1-10 alkyl; C 1-10 alkoxy; C 6-20 aryloxy; C 1-10 alkylamino; C 6-20 arylamino; C 1-10 alkylsilyl; C 6-20 arylsilyl; C 6-20 aryl; or C 2-20 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S;
X 6 is NR′ 2 , C(R′ 3 )(R′ 4 ), O, or S;
R' 2 To R' 4 are each independently hydrogen; C 1-10 alkyl; C 6-20 aryl; or C 2-20 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S;
p is an integer from 0 to 7,
R' 5 are each independently hydrogen; C 1-10 alkyl; C 6-20 aryl; or C 2-20 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.
B1 및 B2는 각각 독립적으로, 인접한 오각 고리와 융합된 벤젠; 나프탈렌; 페난트렌; 또는 디벤조퓨란인,
화합물.
According to claim 1,
B 1 and B 2 are each independently benzene fused to an adjacent pentacyclic ring; naphthalene; phenanthrene; or dibenzofuran,
compound.
화학식 2 및/또는 화학식 3의 부분은 각각 독립적으로 하기로 이루어지는 군에서 선택되는 어느 하나인,
화합물:
According to claim 1,
Formula 2 and/or Formula 3 Each part is independently any one selected from the group consisting of
compound:
Ar3 및 Ar4는 각각 독립적으로 하기로 이루어지는 군에서 선택되는 어느 하나인, 화합물:
상기에서, R1, R2, 및 L은 제1항에서 정의한 바와 같다
According to claim 1,
Ar 3 and Ar 4 are each independently any one selected from the group consisting of:
In the above, R 1 , R 2 , and L are as defined in claim 1
R1 및 R2는 각각 독립적으로, 치환 또는 비치환된 C1-30 알킬; 치환 또는 비치환된 C6-30 아릴이거나, 또는 R1 및 R2는 서로 연결되어 C3-30의 사이클로알칸 고리를 형성하는,
화합물.
According to claim 1,
R 1 and R 2 are each independently, substituted or unsubstituted C 1-30 alkyl; substituted or unsubstituted C 6-30 aryl, or R 1 and R 2 are linked to each other to form a C 3-30 cycloalkane ring,
compound.
R1 및 R2는 각각 독립적으로, 메틸; 페닐; 메틸페닐; 또는 t-부틸페닐이거나, 또는 R1 및 R2가 서로 연결되어 사이클로헥산고리를 형성하는,
화합물.
According to claim 1,
R 1 and R 2 are each independently methyl; phenyl; methylphenyl; or t-butylphenyl, or R 1 and R 2 are linked to each other to form a cyclohexane ring,
compound.
L은 단일 결합, O, 또는 Si(CH3)2인,
화합물.
According to claim 1,
L is a single bond, O, or Si(CH 3 ) 2 ;
compound.
화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
compound:
a first electrode; a second electrode provided to face the first electrode; and a light emitting layer provided between the first electrode and the second electrode, wherein the light emitting layer comprises the compound according to any one of claims 1 to 10. .
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200035798A KR20210119196A (en) | 2020-03-24 | 2020-03-24 | Novel compound and organic light emitting device comprising the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200035798A KR20210119196A (en) | 2020-03-24 | 2020-03-24 | Novel compound and organic light emitting device comprising the same |
Publications (1)
Publication Number | Publication Date |
---|---|
KR20210119196A true KR20210119196A (en) | 2021-10-05 |
Family
ID=78077809
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020200035798A KR20210119196A (en) | 2020-03-24 | 2020-03-24 | Novel compound and organic light emitting device comprising the same |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR20210119196A (en) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20000051826A (en) | 1999-01-27 | 2000-08-16 | 성재갑 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
-
2020
- 2020-03-24 KR KR1020200035798A patent/KR20210119196A/en active Search and Examination
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20000051826A (en) | 1999-01-27 | 2000-08-16 | 성재갑 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR20210118041A (en) | Novel compound and organic light emitting device comprising the same | |
KR102639105B1 (en) | Novel compound and organic light emitting device comprising the same | |
KR102589892B1 (en) | Novel hetero-cyclic compound and organic light emitting device comprising the same | |
KR20220003913A (en) | Novel compound and organic light emitting device comprising the same | |
KR20210117521A (en) | Novel compound and organic light emitting device comprising the same | |
KR20210111573A (en) | Novel compound and organic light emitting device comprising the same | |
KR20200067043A (en) | Novel compound and organic light emitting device comprising the same | |
KR102665292B1 (en) | Novel compound and organic light emitting device comprising the same | |
KR102689532B1 (en) | Novel compound and organic light emitting device comprising the same | |
KR102623891B1 (en) | Novel compound and organic light emitting device comprising the same | |
KR102690833B1 (en) | Novel compound and organic light emitting device comprising the same | |
KR102630138B1 (en) | Novel compound and organic light emitting device comprising the same | |
KR102690832B1 (en) | Novel compound and organic light emitting device comprising the same | |
KR102673282B1 (en) | Novel compound and organic light emitting device comprising the same | |
KR20210119196A (en) | Novel compound and organic light emitting device comprising the same | |
KR102601118B1 (en) | Novel compound and organic light emitting device comprising the same | |
KR102617879B1 (en) | Novel Iridium complex and organic light emitting device comprising the same | |
KR20210119195A (en) | Novel compound and organic light emitting device comprising the same | |
KR20210123661A (en) | Novel compound and organic light emitting device comprising the same | |
KR20210120727A (en) | Novel compound and organic light emitting device comprising the same | |
KR20210133010A (en) | Novel compound and organic light emitting device comprising the same | |
KR20210125839A (en) | Novel compound and organic light emitting device comprising the same | |
KR20210125838A (en) | Novel compound and organic light emitting device comprising the same | |
KR20210089526A (en) | Novel compound and organic light emitting device comprising the same | |
KR20210155430A (en) | Novel compound and organic light emitting device comprising the same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination |