KR101979917B1 - Iridium complex and organic light emitting device comprising the same - Google Patents
Iridium complex and organic light emitting device comprising the same Download PDFInfo
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- KR101979917B1 KR101979917B1 KR1020180001269A KR20180001269A KR101979917B1 KR 101979917 B1 KR101979917 B1 KR 101979917B1 KR 1020180001269 A KR1020180001269 A KR 1020180001269A KR 20180001269 A KR20180001269 A KR 20180001269A KR 101979917 B1 KR101979917 B1 KR 101979917B1
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- 229910052741 iridium Inorganic materials 0.000 title abstract description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000010410 layer Substances 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 45
- -1 or CD 3 Chemical class 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000011368 organic material Substances 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 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 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000002360 preparation method Methods 0.000 description 33
- 239000000463 material Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 16
- 239000000284 extract Substances 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000012300 argon atmosphere Substances 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 229940125904 compound 1 Drugs 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000010406 cathode material Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000032258 transport Effects 0.000 description 6
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 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
- 239000012153 distilled water Substances 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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
- 239000000460 chlorine Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YDMRDHQUQIVWBE-UHFFFAOYSA-N (2-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1O YDMRDHQUQIVWBE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 0 CC1(C)O*(c(cc2)c(C)c3c2c(cccc2)c2[o]3)OC1(C)C Chemical compound CC1(C)O*(c(cc2)c(C)c3c2c(cccc2)c2[o]3)OC1(C)C 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005241 heteroarylamino group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 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
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000007773 negative electrode material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 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
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 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
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
- 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
- YWNJQQNBJQUKME-UHFFFAOYSA-N 2-bromo-5-methylpyridine Chemical compound CC1=CC=C(Br)N=C1 YWNJQQNBJQUKME-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- ZYLPQYYLLRBVOK-FIBGUPNXSA-N 2-phenyl-5-(trideuteriomethyl)pyridine Chemical compound N1=CC(C([2H])([2H])[2H])=CC=C1C1=CC=CC=C1 ZYLPQYYLLRBVOK-FIBGUPNXSA-N 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
- 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
- ACEYZYYNAMWIIE-UHFFFAOYSA-N 4-iododibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(I)=CC=C2 ACEYZYYNAMWIIE-UHFFFAOYSA-N 0.000 description 1
- ZYLPQYYLLRBVOK-UHFFFAOYSA-N 5-methyl-2-phenylpyridine Chemical compound N1=CC(C)=CC=C1C1=CC=CC=C1 ZYLPQYYLLRBVOK-UHFFFAOYSA-N 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
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YCWFOPXDKLTMFH-UHFFFAOYSA-N Cc(c1c(cc2)c(cccc3)c3[o]1)c2Br Chemical compound Cc(c1c(cc2)c(cccc3)c3[o]1)c2Br YCWFOPXDKLTMFH-UHFFFAOYSA-N 0.000 description 1
- XLTFRTTTZWMJJQ-UHFFFAOYSA-N Cc1cccc2c1[o]c1c2cccc1 Chemical compound Cc1cccc2c1[o]c1c2cccc1 XLTFRTTTZWMJJQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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- 229910052688 Gadolinium Inorganic materials 0.000 description 1
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- 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
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- 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
- 229910052772 Samarium Inorganic materials 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
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000005332 alkyl sulfoxy group Chemical group 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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
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- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
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- 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
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 238000001771 vacuum deposition Methods 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
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
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- 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
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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Abstract
본 발명은 이리듐 착체 및 이를 이용한 유기발광 소자를 제공한다.The present invention provides an iridium complex and an organic light emitting device using the same.
Description
본 발명은 이리듐 착체 및 이를 이용한 유기 발광 소자에 관한 것이다. The present invention relates to an iridium complex and an organic light emitting device using 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, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research has been conducted.
유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 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. The organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. The organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.
상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다.There is a continuing need for the development of new materials for the organic materials used in such organic light emitting devices.
본 발명은 이리듐 착체 및 이를 이용한 유기 발광 소자에 관한 것이다. The present invention relates to an iridium complex and an organic light emitting device using the same.
본 발명은 하기 화학식 1 또는 하기 화학식 2로 표시되는 화합물을 제공한다:The present invention provides a compound represented by the following Formula 1 or 2:
[화학식 1][Chemical Formula 1]
[화학식 2](2)
상기 화학식 1 및 2에서, In the
X는 O, 또는 S이고, X is O, or S,
R1은 비치환되거나 또는 중수소로 치환된 C1-60 알킬; 탄소수 1 내지 60의 실릴; 또는 치환 또는 비치환된 C6-60 아릴이고, R 1 is C 1-60 alkyl unsubstituted or substituted by deuterium; Silyl having 1 to 60 carbon atoms; Or substituted or unsubstituted C 6-60 aryl,
R2 및 R3는 각각 독립적으로 수소; 또는 비치환되거나 또는 중수소로 치환된 C1-60 알킬이고, R 2 and R 3 are each independently hydrogen; Or C 1-6 0 alkyl substituted unsubstituted or substituted by deuterium,
n은 1 또는 2이다.n is 1 or 2;
또한, 본 발명은 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자에 있어서, 상기 유기물층은 상기 화합물을 포함하는 발광층을 포함하는, 유기 발광 소자를 제공한다.The present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer includes a light emitting layer containing the compound.
상술한 화학식 1 또는 2로 표시되는 화합물은 유기 발광 소자의 유기물 층, 특히 발광층의 재료로서 사용될 수 있으며, 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. The compound represented by Formula 1 or 2 described above can be used as an organic material layer of an organic light emitting device, particularly a material of a light emitting layer, and can improve the efficiency, the driving voltage and / or the lifetime characteristics of the organic light emitting device.
도 1은 기판(1), 양극(2), 발광층(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) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.Fig. 1 shows an example of an organic light-emitting device comprising a
2 shows an example of an organic light emitting element comprising a
이하, 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention.
본 명세서에서, 
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 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 헤테로고리기로 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, 비페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다.As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and 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 carbon number of the carbonyl group is not particularly limited, but it is 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, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. 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 is preferably 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, But are 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, and a phenylboron group.
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 one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.
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 straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another 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, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
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. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are 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, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우, 
본 명세서에 있어서, 헤테로고리기는 이종 원소로 O, N, Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 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, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a hetero ring group containing at least one of O, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, an isoxazolyl group, A benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group,
본 명세서에 있어서, 아르알킬기, 아르알케닐기, 알킬아릴기, 아릴아민기 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 헤테로고리기에 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 헤테로고리기에 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 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group. In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group. In the present specification, the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.
상기 화학식 1 또는 2에서, 바람직하게는, R1은 비치환되거나 또는 중수소로 치환된 C1-5 알킬; 탄소수 3 내지 10의 실릴; 또는 치환 또는 비치환된 C6-10 아릴이다. 보다 바람직하게는, R1은 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, tert-부틸, 펜틸, 이소펜틸, tert-펜틸, 네오펜틸, sec-펜틸, 3-펜틸, CD3, Si(CH3)3, 또는 페닐이다. In the above formula (1) or (2), preferably, R 1 is C 1-5 alkyl which is unsubstituted or substituted by deuterium; Silyl having 3 to 10 carbon atoms; Or substituted or unsubstituted C 6-10 aryl. More preferably, R 1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert- butyl, pentyl, isopentyl, tert- pentyl, neo-pentyl, sec- pentyl, 3-pentyl, CD 3, Si It is (CH 3) 3, or phenyl.
바람직하게는, R2 및 R3는 각각 독립적으로 수소; 또는 비치환되거나 또는 중수소로 치환된 C1-5 알킬이다. 보다 바람직하게는, R2 및 R3는 각각 독립적으로 수소, 메틸, 또는 CD3이다. Preferably, R 2 and R 3 are each independently selected from the group consisting of hydrogen; Or C 1-5 alkyl unsubstituted or substituted by deuterium. More preferably, R 2 and R 3 are each independently hydrogen, methyl, or CD 3 .
상기 화학식 1 또는 2로 표시되는 화합물의 대표적인 예는 다음과 같다:Representative examples of the compound represented by the above formula (1) or (2) are as follows:
또한, 본 발명은, 일례로 하기 반응식 1과 같은 상기 화학식 1 또는 2로 표시되는 화합물(n이 2인 경우)의 제조 방법을 제공하며, n이 1인 경우에도 적용할 수 있다:The present invention also provides, for example, a process for preparing a compound represented by the above formula (1) or (2) (when n is 2) as shown in
[반응식 1][Reaction Scheme 1]
상기 제조 방법은 후술할 실시예에서 구체화할 수 있다. The above production method can be embodied in an embodiment to be described later.
또한, 본 발명은 상기 화학식 1 또는 2로 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 1층 이상의 유기물층을 포함하는 유기 발광 소자에 있어서, 상기 유기물층은 상기 화학식 1 또는 2로 표시되는 화합물을 포함하는 발광층을 포함하는, 유기 발광 소자를 제공한다. Also, the present invention provides an organic light emitting device comprising a compound represented by the above formula (1) or (2). In one embodiment, the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein the organic compound layer comprises a compound represented by
본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
또한, 본 발명에 따른 유기 발광 소자는, 기판 상에 양극, 1층 이상의 유기물 층 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 유기물 층 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.In addition, 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 layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS.
도 1은 기판(1), 양극(2), 발광층(3), 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1 또는 2로 표시되는 화합물은 상기 발광층에 포함될 수 있다. Fig. 1 shows an example of an organic light-emitting device comprising a
도 2는 기판 (1), 양극(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 음극(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화학식 1 또는 2로 표시되는 화합물은 발광층에 포함될 수 있다. 2 shows an example of an organic light emitting element comprising a
본 발명에 따른 유기 발광 소자는, 상기 화학식 1 또는 2로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한, 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. The organic electroluminescent device according to the present invention can be manufactured by materials and methods known in the art except for the compound represented by the above formula (1) or (2). In addition, when the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
예컨대, 본 발명에 따른 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 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. 이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode Forming an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and then depositing a material usable as a cathode on the organic material layer. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
또한, 상기 화학식 1 또는 2로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.The compound represented by
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 such a method, an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode 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 a cathode.
상기 양극 물질로는 통상 유기물 층으로 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 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted to the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SNO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
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 negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are 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 고분자 등이 있으나, 이들에만 한정 되는 것은 아니다. The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferred that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material. Is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
상기 발광층은 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송 받아 결합시킴으로써 가시광선 영역의 빛을 내는 층을 의미한다. 상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있으며, 상기 도펀트 재료로는 상술한 화학식 1 또는 2로 표시되는 화합물을 사용할 수 있다. The light emitting layer refers to a layer that emits light in a visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively. The light emitting layer may include a host material and a dopant material, and the dopant material may be a compound represented by the above formula (1) or (2).
상기 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 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 host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
상기 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로, 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘, 바륨, 칼슘, 이테르븀 및 사마륨이고, 각 경우 알루미늄 층 또는 실버층이 뒤따른다.The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, and the like, but are 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But 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 front emission type, a back emission type, or a both-sided emission type, depending on the material used.
또한, 상기 화학식 1 또는 2로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.The compound represented by
상기 화학식 1 또는 2로 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 preparation of the compound represented by the above formula (1) or (2) and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
[[ 제조예Manufacturing example ]]
제조예Manufacturing example 1: 중간체 1의 제조 1: Preparation of intermediate 1
1) 중간체 1-1의 제조1) Preparation of intermediate 1-1
3구 플라스크에 4-아이오도디벤조[b,d]퓨란(30.0 g, 102.0 mmol), 포타슘 포스페이트(65.0 g, 306.0 mmol)를 톨루엔(600 ml), 및 물(60 ml)에 녹여 넣었다. 반응물을 20분간 질소 퍼징하고 2,4,6-트리메틸-1,3,5,2,4,6-트리옥사트리보리난(14.1 g, 112.2 mmol), Pd2(dba)3(0.9 g, 1.0 mmol) 및 S-Phos(1.7 g, 4.1 mmol)를 넣고, 아르곤 분위기 환류 조건 하에서 18시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 물(200 ml)을 넣고 분액 깔대기에 옮겨 유기층을 추출하였다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 1-1을 수득하였다(18.0 g, 수율 91%, MS:[M+H]+= 182).4-iododibenzo [b, d] furan (30.0 g, 102.0 mmol) and potassium phosphate (65.0 g, 306.0 mmol) were dissolved in toluene (600 ml) and water (60 ml). The reaction was purged with nitrogen for 20 minutes and 2,4,6-trimethyl-1,3,5,2,4,6-trioxatrifluoride (14.1 g, 112.2 mmol), Pd 2 (dba) 3 (0.9 g, 1.0 mmol) and S-Phos (1.7 g, 4.1 mmol) were added thereto, and the mixture was stirred under reflux in an argon atmosphere for 18 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (200 ml) was added to the separatory funnel to extract an organic layer. The extract was dried with MgSO 4 , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate 1-1 (18.0 g, yield 91%, MS: [M + H] + = 182) .
2) 중간체 1-2의 제조2) Preparation of intermediate 1-2
3구 플라스크에 중간체 1-1(15.0 g, 82.3 mmol), 소디움 카르보네이트(9.2 g, 86.4 mmol)을 n-헥산(150 ml)에 녹이고 여기에 브로민(4.4 ml, 86.4 mmol)을 적가하여 상온에서 72시간 동안 교반하였다. 반응이 종료되면 소디움 싸이오설페이트 수용액을 첨가한 후, 반응액을 분액 깔대기에 옮겨 유기층을 추출하였다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 1-2를 수득하였다(15.5 g, 수율 72%, MS:[M+H]+= 261).Intermediate 1-1 (15.0 g, 82.3 mmol) and sodium carbonate (9.2 g, 86.4 mmol) were dissolved in n-hexane (150 ml) and bromine (4.4 ml, 86.4 mmol) And the mixture was stirred at room temperature for 72 hours. After the reaction was completed, sodium thiosulfate aqueous solution was added, and the reaction solution was transferred to a separatory funnel to extract an organic layer. The extract was dried over MgSO4, filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate 1-2 (15.5 g, yield 72%, MS: [M + H] + = 261).
3) 중간체 1-3의 제조3) Preparation of intermediate 1-3
3구 플라스크에 중간체 1-2(15.0 g, 57.4 mmol), 비스(피나콜라토)디보론(17.5 g, 68.9 mmol), Pd(dba)2(0.7 g, 1.1 mmol), 트리사이클로헥실포스핀(0.6 g, 2.3 mmol), KOAc(11.3 g, 114.9 mmol), 및 1,4-디옥산(225 ml)을 넣고, 아르곤 분위기 환류 조건 하에서 12시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, 물(200 mL)을 가하여 에틸 아세테이트로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 1-3을 수득하였다(20.5 g, 수율 78%, MS:[M+H]+= 384).(15.0 g, 57.4 mmol), bis (pinacolato) diboron (17.5 g, 68.9 mmol), Pd (dba) 2 (0.7 g, 1.1 mmol), tricyclohexylphosphine (0.6 g, 2.3 mmol), KOAc (11.3 g, 114.9 mmol) and 1,4-dioxane (225 ml) were placed and stirred for 12 hours under reflux in an argon atmosphere. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and water (200 mL) was added thereto, followed by extraction with ethyl acetate. After drying the extract with MgSO 4, filtered and concentrated, then, the sample was purified to give the intermediate 1-3 by column chromatography on silica gel (20.5 g, yield 78%, MS: [M + H] + = 384) .
4) 중간체 1의 제조4) Preparation of intermediate 1
3구 플라스크에 중간체 1-3(14.0 g, 45.4 mmol), 2-브로모피리딘(7.9 g, 50.0 mmol)을 THF(210 ml)에 녹이고 K2CO3(25.1 g, 181.7 mmol)을 물(105 ml)에 녹여 넣었다. 여기에 Pd(PPh3)4(2.1 g, 1.8 mmol)를 넣고, 아르곤 분위기 환류 조건 하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, 물과 에틸 아세테이트로 추출하였다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 1을 수득하였다(8.6 g, 수율 73%, MS:[M+H]+= 259).The intermediate 1-3 (14.0 g, 45.4 mmol) and 2-bromopyridine (7.9 g, 50.0 mmol) were dissolved in THF (210 ml) and K 2 CO 3 (25.1 g, 181.7 mmol) 105 ml). Here, insert the Pd (PPh 3) 4 (2.1 g, 1.8 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried with MgSO 4 , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate 1 (8.6 g, yield 73%, MS: [M + H] + = 259).
제조예Manufacturing example 2: 중간체 2의 제조 2: Preparation of intermediate 2
2구 플라스크에 중간체 1(8.0 g, 30.9 mmol), 소디움 에톡사이드(4.2 g, 61.7 mmol), 및 에탄올-D6(130 ml)를 넣고, 환류 조건 하에서 72시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각하고 용매를 농축한 후, 물과 에틸 아세테이트를 넣고 분액 깔대기에 옮겨, 유기층을 추출하였다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 2를 수득하였다(6.1 g, 수율 75%, MS:[M+H]+= 262).Intermediate 1 (8.0 g, 30.9 mmol), sodium ethoxide (4.2 g, 61.7 mmol), and ethanol-D6 (130 ml) were placed in a two-necked flask and stirred under reflux for 72 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent was concentrated. Then, water and ethyl acetate were added to the separatory funnel, and the organic layer was extracted. The extract was dried with MgSO 4 , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate 2 (6.1 g, yield 75%, MS: [M + H] + = 262).
제조예Manufacturing example 3: 중간체 3의 제조 3: Preparation of intermediate 3
1) 중간체 3-1의 제조1) Preparation of intermediate 3-1
3구 플라스크에 1-아이오도디벤조[b,d]퓨란-2-올(20.0 g, 64.5 mmol), 페닐보론산(8.7 g, 70.9 mmol)을 THF(300 ml)에 녹이고, K2CO3(35.7 g, 258.0 mmol)을 물(150 ml)에 녹여 넣었다. 여기에 Pd(PPh3)4(3.0 g, 2.6 mmol)를 넣고, 아르곤 분위기 환류 조건 하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, 물과 에틸 아세테이트로 추출하였다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 3-1을 수득하였다(12.9 g, 수율 77%, MS:[M+H]+= 260).(20.0 g, 64.5 mmol) and phenylboronic acid (8.7 g, 70.9 mmol) were dissolved in THF (300 ml) and K 2 CO 3 (35.7 g, 258.0 mmol) was dissolved in water (150 ml). Here, insert the Pd (PPh 3) 4 (3.0 g, 2.6 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried with MgSO 4 , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate 3-1 (12.9 g, yield 77%, MS: [M + H] + = 260) .
2) 중간체 3-2의 제조2) Preparation of intermediate 3-2
3구 플라스크에 중간체 3-1(12.0 g, 46.1 mmol)를 아세토니트릴(340 ml)에 녹인 후, 트리에틸아민(20 ml, 73.8 mmol), 퍼플루오로-1-부탄술포닐 플루오라이드(12 ml, 69.2 mmol)를 넣고 상온에서 밤새 교반하였다. 반응이 종료되면 에틸 아세테이트로 묽히고 분액 깔대기에 옮겨 0.5 M 소디움 비설페이트 수용액을 이용해 씻어준 후, 유기층을 추출하였다. 추출액을 MgSO4로 건조하고, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 3-2를 수득하였다(18.8 g, 수율 75%, MS:[M+H]+= 542).Intermediate 3-1 (12.0 g, 46.1 mmol) was dissolved in acetonitrile (340 ml), and then triethylamine (20 ml, 73.8 mmol) and perfluoro-1-butanesulfonyl fluoride ml, 69.2 mmol), which was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was diluted with ethyl acetate, transferred to a separatory funnel, washed with a 0.5 M aqueous sodium bisulfate solution, and then extracted with an organic layer. The extract was dried over MgSO 4 , filtered and concentrated and the sample was purified by silica gel column chromatography to give intermediate 3-2 (18.8 g, yield 75%, MS: [M + H] + = 542) .
3) 중간체 3의 제조3) Preparation of intermediate 3
3구 플라스크에 중간체 3-2(18.0 g, 33.2 mmol), 피리딘-2-일보론산(4.5 g, 36.5 mmol)을 THF(270 ml)에 녹이고 K2CO3(18.3 g, 132.8 mmol)을 물(135 ml)에 녹여 넣었다. 여기에 Pd(PPh3)4(1.5 g, 1.3 mmol)를 넣고, 아르곤 분위기 환류 조건 하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, 물과 에틸 아세테이트로 추출하였다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 3-3을 수득하였다(8.3 g, 수율 78%, MS:[M+H]+= 321).(18.0 g, 33.2 mmol) and pyridine-2-ylboronic acid (4.5 g, 36.5 mmol) were dissolved in THF (270 ml) and K 2 CO 3 (18.3 g, 132.8 mmol) (135 ml). Here, insert the Pd (PPh 3) 4 (1.5 g, 1.3 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried with MgSO 4 , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain intermediate 3-3 (8.3 g, yield 78%, MS: [M + H] + = 321) .
제조예Manufacturing example 4: 중간체 4의 제조 4: Preparation of intermediate 4
1) 중간체 4-1의 제조1) Preparation of intermediate 4-1
3구 플라스크에 1-플루오로-2-아이오도-3-메틸벤젠(25.0 g, 105.9 mmol), (2-하이드록시페닐)보론산(16.1 g, 116.5 mmol)을 THF(375 ml)에 녹이고 K2CO3(58.6 g, 423.7 mmol)을 물(190 ml)에 녹여 넣었다. 여기에 Pd(PPh3)4(4.9 g, 4.2 mmol)를 넣고, 아르곤 분위기 환류 조건 하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, 물과 에틸 아세테이트로 추출하였다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 4-1을 수득하였다(15.2 g, 수율 71%, MS:[M+H]+= 202).3-methylbenzene (25.0 g, 105.9 mmol) and (2-hydroxyphenyl) boronic acid (16.1 g, 116.5 mmol) were dissolved in THF (375 ml) K 2 CO 3 (58.6 g, 423.7 mmol) was dissolved in water (190 ml). Here, insert the Pd (PPh 3) 4 (4.9 g, 4.2 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried with MgSO 4 , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate 4-1 (15.2 g, yield 71%, MS: [M + H] + = 202) .
2) 중간체 4-2의 제조2) Preparation of intermediate 4-2
3구 플라스크에 중간체 4-1(15.0 g, 74.2 mmol), K2CO3(20.5 g, 148.3 mmol), NMP(200 ml)를 넣고 120℃에서 밤새 교반하였다. 반응이 종료되면 상온으로 냉각한 후 반응액에 물(150 ml)을 조금씩 적가하였다. 그 후 반응액을 분액 깔대기에 옮기고, 물과 에틸 아세테이트로 유기층을 추출하였다. 추출액을 MgSO4로 건조하고, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 4-2를 수득하였다(11.6 g, 수율 86%, MS:[M+H]+= 182).Intermediate 4-1 (15.0 g, 74.2 mmol), K 2 CO 3 (20.5 g, 148.3 mmol) and NMP (200 ml) were added to a three-necked flask and stirred overnight at 120 ° C. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (150 ml) was added dropwise to the reaction solution. The reaction solution was then transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO 4 , filtered and concentrated and the sample was purified by silica gel column chromatography to give Intermediate 4-2 (11.6 g, yield 86%, MS: [M + H] + = 182) .
3) 중간체 4-3의 제조3) Preparation of intermediate 4-3
2구 플라스크에 중간체 4-2(10.0 g, 54.9 mmol), NBS(10.3 g, 57.6 mmol), 및 DMF(200 ml)를 넣고, 아르곤 분위기 하에서 상온에서 8시간 동안 교반하였다. 반응 종료 후, 반응액을 분액 깔대기에 옮기고, 물과 에틸 아세테이트로 유기층을 추출하였다. 추출액을 MgSO4로 건조하고, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 4-3을 수득하였다(12.2 g, 수율 85%, MS:[M+H]+= 261).Intermediate 4-2 (10.0 g, 54.9 mmol), NBS (10.3 g, 57.6 mmol) and DMF (200 ml) were placed in a two-necked flask and stirred at room temperature for 8 hours under argon atmosphere. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and an organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO 4 , filtered and concentrated and the sample was purified by silica gel column chromatography to give Intermediate 4-3 (12.2 g, yield 85%, MS: [M + H] + = 261) .
4) 중간체 4-4의 제조4) Preparation of intermediate 4-4
3구 플라스크에 중간체 4-3(12.0 g, 46.0 mmol), 비스(피나콜라토)디보론(14.0 g, 55.1 mmol), Pd(dba)2(0.5 g, 0.9 mmol), 트리사이클로헥실포스핀(0.5 g, 0.9 mmol), KOAc(9.0 g, 91.9 mmol), 및 1,4-디옥산(180 ml)을 넣고, 아르곤 분위기 환류 조건 하에서 12시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, 물(200 mL)을 가하여 에틸 아세테이트로 추출했다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 4-4를 수득하였다(11.6 g, 수율 82%, MS:[M+H]+= 308).(12.0 g, 46.0 mmol), bis (pinacolato) diboron (14.0 g, 55.1 mmol), Pd (dba) 2 (0.5 g, 0.9 mmol), tricyclohexylphosphine (0.5 g, 0.9 mmol), KOAc (9.0 g, 91.9 mmol), and 1,4-dioxane (180 ml) were placed and stirred under an argon atmosphere reflux condition for 12 hours. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and water (200 mL) was added thereto, followed by extraction with ethyl acetate. The extract was dried with MgSO 4 , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate 4-4 (11.6 g, yield 82%, MS: [M + H] + = 308) .
5) 중간체 4의 제조5) Preparation of intermediate 4
3구 플라스크에 중간체 4-4(11.0 g, 35.7 mmol), 2-브로모-5-메틸피리딘(6.8 g, 39.3 mmol)을 THF(165 ml)에 녹이고 K2CO3(19.7 g, 142.8 mmol)을 물(83 ml)에 녹여 넣었다. 여기에 Pd(PPh3)4(1.6 g, 1.4 mmol)를 넣고, 아르곤 분위기 환류 조건 하에서 8시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, 반응액을 분액 깔대기에 옮기고, 물과 에틸 아세테이트로 추출하였다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 4을 수득하였다(7.0 g, 수율 72%, MS:[M+H]+= 273).(11.0 g, 35.7 mmol) and 2-bromo-5-methylpyridine (6.8 g, 39.3 mmol) were dissolved in THF (165 ml) and K 2 CO 3 (19.7 g, 142.8 mmol ) Was dissolved in water (83 ml). Here, insert the Pd (PPh 3) 4 (1.6 g, 1.4 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried with MgSO 4 , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate 4 (7.0 g, yield 72%, MS: [M + H] + = 273).
제조예Manufacturing example 5: 중간체 5의 제조 5: Preparation of intermediate 5
2구 플라스크에 중간체 4(7.0 g, 25.6 mmol), 소디움 에톡사이드(7.0 g, 102.4 mmol), 에탄올-D6(220 ml)를 환류 조건 하에서 72시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각하고 용매를 농축한 후, 물과 에틸 아세테이트를 넣고 분액 깔대기에 옮겨, 유기층을 추출하였다. 추출액을 MgSO4로 건조 후, 여과 및 농축한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 중간체 5를 수득하였다(4.4 g, 수율 62%, MS:[M+H]+= 279).Intermediate 4 (7.0 g, 25.6 mmol), sodium ethoxide (7.0 g, 102.4 mmol) and ethanol-D6 (220 ml) were stirred under reflux for 72 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent was concentrated. Then, water and ethyl acetate were added to the separatory funnel, and the organic layer was extracted. The extract was dried with MgSO 4 , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate 5 (4.4 g, yield 62%, MS: [M + H] + = 279).
제조예Manufacturing example 6: 중간체 A의 제조 6: Preparation of intermediate A
1) 중간체 A-1의 제조1) Preparation of intermediate A-1
3구 플라스크에 이리듐(III) 클로라이드 하이드레이트(15.0 g, 42.5 mmol), 및 2-페닐피리딘(2.2 g, 14.0 mmol)을 2-에톡시에탄올(140 ml), 물(47 ml)과 함께 넣고 아르곤 분위기 환류 조건 하에서 18시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각하고 침전물을 여과하여 메탄올과 헥산으로 씻어주고 건조한 후, 추가 정제 없이 다음 반응에 이용하였다(21.7 g, 수율 95%).(III) chloride hydrate (15.0 g, 42.5 mmol) and 2-phenylpyridine (2.2 g, 14.0 mmol) were placed in a three-necked flask together with 140 ml of 2-ethoxyethanol and 47 ml of water, And the mixture was stirred under an atmosphere of reflux for 18 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the precipitate was filtered, washed with methanol and hexane, dried and then used in the next reaction without further purification (21.7 g, yield 95%).
2) 중간체 A의 제조2) Preparation of intermediate A
3구 플라스크에 중간체 A-1(20.0 g, 18.7 mmol)을 CH2Cl2(1120 ml)에 넣고 상온에서 교반하고 여기에 실버 트리플레이트(10.1 g, 39.2 mmol)를 메탄올(560 ml)에 녹인 용액을 천천히 적가하여 밤새 교반하였다. 반응이 완료되면 반응액을 셀라이트 플러그를 이용하여 여과한 후, 여과액을 농축하여 얻은 고체를 추가 정제 없이 다음 반응에 이용하였다(25.8 g, 수율 97%).To the three-necked flask, 20.0 g (18.7 mmol) of Intermediate A-1 was added to 1120 ml of CH 2 Cl 2 and stirred at room temperature. Silver triflate (10.1 g, 39.2 mmol) was dissolved in methanol (560 ml) The solution was slowly added dropwise and stirred overnight. After completion of the reaction, the reaction solution was filtered using a celite plug, and the filtrate was concentrated to obtain a solid (25.8 g, yield 97%) without further purification.
제조예Manufacturing example 7: 중간체 B의 제조 7: Preparation of intermediate B
2-페닐피리딘 대신 5-메틸-2-페닐피리딘을 사용한 것을 제외하고는, 중간체 A의 제조 방법과 동일한 방법으로 중간체 B를 제조하였다.Intermediate B was prepared in the same manner as in the preparation of Intermediate A, except that 5-methyl-2-phenylpyridine was used instead of 2-phenylpyridine.
제조예Manufacturing example 8: 중간체 C의 제조 8: Preparation of intermediate C
2-페닐피리딘 대신 대신 5-(메틸-d3)-2-페닐피리딘을 사용한 것을 제외하고는, 중간체 A의 제조 방법과 동일한 방법으로 중간체 C를 제조하였다.Intermediate C was prepared in the same manner as in the preparation of Intermediate A, except for using 5- (methyl-d3) -2-phenylpyridine instead of 2-phenylpyridine.
[[ 실시예Example ]]
실시예Example
1: 화합물 1의 제조 1: Preparation of
3구 플라스크에 중간체 A(20.0g, 28.0mmol), 중간체 1(18.2 g, 70.1 mmol), 에탄올(140 ml), 및 메탄올(140 ml)를 넣고, 아르곤 분위기 환류 조건 하에서 20시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각하고 에탄올로 묽혀준 후, 셀라이트를 넣고 10분간 교반하였다. 이 후 혼합물을 실리카 플러그 상에서 여과하고 에탄올 및 헥산으로 세정한 후 여과액은 버렸다. 셀라이트/실리카 플러그는 CH2Cl2로 세정하여 생성물을 녹여내고, 이소프로판올을 이용하여 침전시켜 여과하였다. 여과한 침전물은 이소프로판올과 헥산으로 씻어주고 건조한 후, 시료를 실리카 겔 컬럼 크로마토그래피로 정제한 후, 최종적으로 승화 정제를 통해 화합물 1을 수득하였다(4.3 g, 수율 10%, MS:[M+H]+= 759).Intermediate A (20.0 g, 28.0 mmol), Intermediate 1 (18.2 g, 70.1 mmol), ethanol (140 ml) and methanol (140 ml) were placed in a three-necked flask and stirred under an argon atmosphere reflux condition for 20 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, diluted with ethanol, and then celite was added thereto, followed by stirring for 10 minutes. The mixture was then filtered over a silica plug, washed with ethanol and hexane, and the filtrate discarded. The celite / silica plug was rinsed with CH 2 Cl 2 to dissolve the product, precipitate with isopropanol and filter. The filtered precipitate was washed with isopropanol and hexane and dried. The sample was purified by silica gel column chromatography, and finally
실시예Example
2: 화합물 2의 제조 2: Preparation of
중간체 1 대신 중간체 2를 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 방법으로 화합물 2를 제조하였다.
MS:[M+H]+= 762MS: [M + H] < + > = 762
실시예Example
3: 화합물 3의 제조 3: Preparation of
중간체 A 대신 중간체 B를 사용하고, 중간체 1 대신 중간체 3을 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 방법으로 화합물 3을 제조하였다.
MS:[M+H]+= 849MS: [M + H] < + > = 849
실시예Example
4: 화합물 4의 제조 4: Preparation of
중간체 A 대신 중간체 B를 사용하고, 중간체 1 대신 중간체 4를 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 방법으로 화합물 4를 제조하였다.
MS:[M+H]+= 800MS: [M + H] < + > = 800
실시예Example
5: 화합물 5의 제조 5: Preparation of
중간체 A 대신 중간체 C를 사용하고, 중간체 1 대신 중간체 2를 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 방법으로 화합물 5를 제조하였다.
MS:[M+H]+= 796MS: [M + H] < + > = 796
실시예Example
6: 화합물 6의 제조 6: Preparation of
중간체 A 대신 중간체 C를 사용하고, 중간체 1 대신 중간체 5를 사용한 것을 제외하고는, 화합물 1의 제조 방법과 동일한 방법으로 화합물 6을 제조하였다.
MS:[M+H]+= 813MS: [M + H] < + > = 813
[[ 실험예Experimental Example ]]
실험예Experimental Example 1 One
ITO(Indium Tin Oxide)가 1,400 Å의 두께로 박막 코팅된 유리기판을 세제에 녹인 증류수에 넣고 초음파로 세척하였다. 이때 세제로는 피셔사(Fischer Co.)의 Decon™ CON705 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 0.22 ㎛ sterilizing filter로 2차 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필 알코올, 아세톤 및 메탄올의 용제로 각각 10분간 초음파 세척하고, 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후, 진공 증착기로 기판을 수송시켰다.The glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1,400 Å was immersed in distilled water dissolved in detergent and washed with ultrasonic waves. As a detergent, Decon (TM) CON705 product of Fischer Co. was used, and distilled water which was secondly filtered with a 0.22 μm sterilizing filter manufactured by Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol for 10 minutes, dried, and then transported to a plasma cleaner. The substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
이렇게 준비된 ITO 투명전극 위에 하기 HT-A 화합물 95 중량%와 하기 P-DOPANT 화합물 5 중량%의 혼합물을 100 Å의 두께로 열 진공 증착하고, 이어서 하기 HT-A 화합물만 1150 Å의 두께로 증착하여 정공수송층을 형성하였다. 상기 정공수송층 위에 하기 HT-B 화합물을 450 Å의 두께로 열 진공 증착하여 전자저지층을 형성하였다. 이어서, 상기 전자저지층 위에, 호스트로 하기 GH 화합물(94 중량%)과 도판트로 앞서 제조한 화합물 1(6 중량%)의 혼합물을 400 Å의 두께로 진공 증착하여 발광층을 형성하였다. 이어서, 상기 발광층 위에, 하기 ET-A 화합물을 50 Å의 두께로 진공 증착하여 정공저지층을 형성하였다. 상기 정공저지층 위에 하기 ET-B 화합물과 하기 Liq 화합물을 2:1의 중량비로 혼합하여 250 Å의 두께로 열 진공 층착하여 전자수송층을 형성하고, 이어서 LiF와 마그네슘을 1:1의 중량비로 혼합하여 30 Å의 두께로 진공 증착하여 전자주입층을 형성하였다. 상기 전자 주입층 위에 마그네슘과 은을 1:4의 중량비로 혼합 후 160 Å의 두께로 증착하여 음극을 형성함으로써, 유기 발광 소자를 제작하였다.On this ITO transparent electrode, a mixture of 95% by weight of the following HT-A compound and 5% by weight of the following P-DOPANT compound was thermally vacuum deposited to a thickness of 100 Å. Then, only the following HT-A compound was deposited to a thickness of 1150 Å Thereby forming a hole transporting layer. The HT-B compound was thermally vacuum deposited on the hole transport layer to a thickness of 450 Å to form an electron blocking layer. Subsequently, a mixture of the following GH compound (94% by weight) and the compound 1 (6% by weight) prepared above as a dopant was vacuum deposited on the electron blocking layer to a thickness of 400 Å to form a light emitting layer. Then, the following ET-A compound was vacuum deposited on the light emitting layer to a thickness of 50 A to form a hole blocking layer. On the hole blocking layer, the following ET-B compound and the following Liq compound were mixed at a weight ratio of 2: 1, and the resulting mixture was thermally vacuum deposited to a thickness of 250 ANGSTROM to form an electron transport layer. Then, LiF and magnesium were mixed at a weight ratio of 1: And vacuum evaporated at a thickness of 30 Å to form an electron injection layer. Magnesium and silver were mixed on the electron injecting layer at a weight ratio of 1: 4, followed by deposition to a thickness of 160 ANGSTROM to form a cathode. Thus, an organic light emitting device was fabricated.
실험예Experimental Example 2 내지 6 2 to 6
화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는 상기 실험예 1과 동일한 방법을 이용하여 유기 발광 소자를 각각 제작하였다.An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of
비교실험예Comparative Experimental Example 1 내지 5 1 to 5
화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는 상기 실험예 1과 동일한 방법을 이용하여 유기 발광 소자를 각각 제작하였다. 하기 표 1에서, GD-1 내지 GD-5는 각각 다음과 같다.An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of
상기 실험예 및 비교 실험예에서 제조한 유기 발광 소자에 전류를 인가하여 전압, 효율 및 수명(T95)를 각각 측정하고, 그 결과를 하기 표 1에 나타내었다. 이때, 전압 및 효율은 10 mA/cm2의 전류 밀도를 인가하여 측정하였으며, 수명(T95)는 20 mA/cm2의 전류 밀도에서 초기 휘도가 95%로 저하할 때까지의 시간을 의미한다.The voltage, efficiency, and lifetime (T95) were measured by applying current to the organic light emitting device manufactured in the Experimental Examples and Comparative Experimental Examples, and the results are shown in Table 1 below. In this case, the voltage and the efficiency were measured by applying a current density of 10 mA / cm 2 , and the lifetime (T95) means a time until the initial luminance decreased to 95% at a current density of 20 mA / cm 2 .
(@10mA/cm2)Voltage (V)
(@ 10 mA / cm 2 )
(@10mA/cm2)Efficiency (cd / A)
(@ 10 mA / cm 2 )
(@20mA/cm2)Life (T95, hr)
(@ 20 mA / cm 2 )
상기 표 1에 나타난 바와 같이, 본 발명의 화학식 1의 R1의 위치가 수소인 경우에 비해 화학식 1의 구조를 갖는 물질들은 이리듐과 직접 결합하는 페닐 고리의 전자 밀도를 변화시키고 이는 발광 효율을 증가시킨다. 따라서, 본 발명의 화학식 1의 화합물을 유기 발광 소자의 발광층 도펀트로 사용할 경우, 고효율, 및 장수명의 유기 발광 소자를 얻을 수 있다.As shown in Table 1, when the position of R 1 in
1: 기판 2: 양극
3: 발광층 4: 음극
5: 정공주입층 6: 정공수송층
7: 발광층 8: 전자수송층1: substrate 2: anode
3: light emitting layer 4: cathode
5: Hole injection layer 6: Hole transport layer
7: light emitting layer 8: electron transporting layer
Claims (7)
[화학식 1]
[화학식 2]
상기 화학식 1 및 2에서,
X는 O, 또는 S이고,
R1은 비치환되거나 또는 중수소로 치환된 C1-60 알킬; 탄소수 1 내지 60의 실릴; 또는 치환 또는 비치환된 C6-60 아릴이고,
R2 및 R3는 각각 독립적으로 수소; 또는 비치환되거나 또는 중수소로 치환된 C1-60 알킬이고,
n은 1 또는 2이다.
A compound represented by the following formula 1 or 2:
[Chemical Formula 1]
(2)
In the above Formulas 1 and 2,
X is O, or S,
R 1 is C 1-60 alkyl unsubstituted or substituted by deuterium; Silyl having 1 to 60 carbon atoms; Or substituted or unsubstituted C 6-60 aryl,
R 2 and R 3 are each independently hydrogen; Or C 1-6 0 alkyl substituted unsubstituted or substituted by deuterium,
n is 1 or 2;
R1은 비치환되거나 또는 중수소로 치환된 C1-5 알킬; 탄소수 3 내지 10의 실릴; 또는 치환 또는 비치환된 C6-10 아릴인,
화합물.
The method according to claim 1,
R 1 is C 1-5 alkyl, unsubstituted or substituted by deuterium; Silyl having 3 to 10 carbon atoms; Or substituted or unsubstituted C 6-10 aryl,
compound.
R1은 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, tert-부틸, 펜틸, 이소펜틸, tert-펜틸, 네오펜틸, sec-펜틸, 3-펜틸, CD3, Si(CH3)3, 또는 페닐인,
화합물.
The method according to claim 1,
R 1 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert- butyl, pentyl, isopentyl, tert- pentyl, neo-pentyl, sec- pentyl, 3-pentyl, CD 3, Si (CH 3 ) 3 , Or phenyl,
compound.
R2 및 R3는 각각 독립적으로 수소; 또는 비치환되거나 또는 중수소로 치환된 C1-5 알킬인,
화합물.
The method according to claim 1,
R 2 and R 3 are each independently hydrogen; Or C 1-5 alkyl unsubstituted or substituted by deuterium,
compound.
R2 및 R3는 각각 독립적으로 수소, 메틸, 또는 CD3인,
화합물.
The method according to claim 1,
R 2 and R 3 are each independently hydrogen, methyl, or CD 3 ,
compound.
상기 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인,
화합물:
The method according to claim 1,
Wherein said compound is any one selected from the group consisting of:
compound:
상기 유기물층은 제1항 내지 제6항 중 어느 하나의 항에 따른 화합물을 포함하는 발광층을 포함하는,
유기 발광 소자.A first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode,
Wherein the organic layer comprises a luminescent layer comprising a compound according to any one of claims 1 to 6,
Organic light emitting device.
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| KR102466672B1 (en) * | 2014-11-28 | 2022-11-15 | 삼성전자주식회사 | Organometallic compound and organic light emitting device including the same |
| JP6582540B2 (en) * | 2015-05-15 | 2019-10-02 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENT ELEMENT, METHOD FOR PRODUCING ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2018138548A (en) | 2013-02-21 | 2018-09-06 | ユニバーサル ディスプレイ コーポレイション | Phosphorescent compound |
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| KR20180080699A (en) | 2018-07-12 |
| CN109311922A (en) | 2019-02-05 |
| WO2018128425A1 (en) | 2018-07-12 |
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