KR20210048018A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents
An electroluminescent compound and an electroluminescent device comprising the same Download PDFInfo
- Publication number
- KR20210048018A KR20210048018A KR1020190131576A KR20190131576A KR20210048018A KR 20210048018 A KR20210048018 A KR 20210048018A KR 1020190131576 A KR1020190131576 A KR 1020190131576A KR 20190131576 A KR20190131576 A KR 20190131576A KR 20210048018 A KR20210048018 A KR 20210048018A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- organic light
- layer
- carbon atoms
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 87
- 239000011368 organic material Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 24
- 238000002347 injection Methods 0.000 claims description 22
- 239000007924 injection Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 14
- 230000000903 blocking effect Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 229940125904 compound 1 Drugs 0.000 claims 1
- 239000010410 layer Substances 0.000 description 108
- -1 1-methylpentyl group Chemical group 0.000 description 45
- 230000015572 biosynthetic process Effects 0.000 description 42
- 238000003786 synthesis reaction Methods 0.000 description 42
- 239000000463 material Substances 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- 238000000605 extraction Methods 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 9
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 9
- 239000003446 ligand Substances 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 7
- 239000011521 glass Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RXKOKVQKECXYOT-UHFFFAOYSA-N 1,2,4,5-tetrabromo-3,6-dimethylbenzene Chemical group CC1=C(Br)C(Br)=C(C)C(Br)=C1Br RXKOKVQKECXYOT-UHFFFAOYSA-N 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 3
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 3
- ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 3
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 3
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 229940126086 compound 21 Drugs 0.000 description 3
- 229940126208 compound 22 Drugs 0.000 description 3
- 229940126540 compound 41 Drugs 0.000 description 3
- 229940126545 compound 53 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- JHBKHLUZVFWLAG-QDNHWIQGSA-N 1,2,4,5-tetrachloro-3,6-dideuteriobenzene Chemical compound [2H]C1=C(Cl)C(Cl)=C([2H])C(Cl)=C1Cl JHBKHLUZVFWLAG-QDNHWIQGSA-N 0.000 description 2
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-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
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 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 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-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
- 239000011787 zinc oxide Substances 0.000 description 2
- RCKXJCCFAPCZHH-UHFFFAOYSA-N (3-methylnaphthalen-1-yl)boronic acid Chemical compound C1=CC=CC2=CC(C)=CC(B(O)O)=C21 RCKXJCCFAPCZHH-UHFFFAOYSA-N 0.000 description 1
- CEEBDYOONUCGQB-UHFFFAOYSA-N (3-phenylquinolin-6-yl)boronic acid Chemical compound C=1C2=CC(B(O)O)=CC=C2N=CC=1C1=CC=CC=C1 CEEBDYOONUCGQB-UHFFFAOYSA-N 0.000 description 1
- UNEURVGVRYJOMG-UHFFFAOYSA-N (4-methoxynaphthalen-1-yl)boronic acid Chemical compound C1=CC=C2C(OC)=CC=C(B(O)O)C2=C1 UNEURVGVRYJOMG-UHFFFAOYSA-N 0.000 description 1
- XDKCHGWZDWHBQO-UHFFFAOYSA-N (6-phenylnaphthalen-2-yl)boronic acid Chemical compound C1=CC2=CC(B(O)O)=CC=C2C=C1C1=CC=CC=C1 XDKCHGWZDWHBQO-UHFFFAOYSA-N 0.000 description 1
- DHYPURXYFPOYQQ-UHFFFAOYSA-N 1,2,4,5-tetrabromo-3,6-diethylbenzene Chemical compound CCC1=C(Br)C(Br)=C(CC)C(Br)=C1Br DHYPURXYFPOYQQ-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- ZWXJKIDBODLOHM-UHFFFAOYSA-N 1,8-naphthyridin-4-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=NC2=N1 ZWXJKIDBODLOHM-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
- 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
- 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
- 125000006607 3,3-dimethylbutyloxy group Chemical group 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
- 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
- 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GQBJXDPQJRYIHO-UHFFFAOYSA-N [6-(trifluoromethyl)naphthalen-2-yl]boronic acid Chemical compound C1=C(C(F)(F)F)C=CC2=CC(B(O)O)=CC=C21 GQBJXDPQJRYIHO-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical group C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006622 cycloheptylmethyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 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
- 238000003618 dip coating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 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
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 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
- 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
- 125000000623 heterocyclic group Chemical group 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
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 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
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 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
- 125000005921 isopentoxy group Chemical group 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
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 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
- 125000006610 n-decyloxy group Chemical group 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
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000005484 neopentoxy group Chemical group 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 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
- 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
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- QIPHSSYCQCBJAX-UHFFFAOYSA-N propan-2-ylboronic acid Chemical compound CC(C)B(O)O QIPHSSYCQCBJAX-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
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ALHRJBIHMIAJAA-UHFFFAOYSA-N pyrido[2,3-b]pyrazin-7-ylboronic acid Chemical compound N1=CC=NC2=CC(B(O)O)=CN=C21 ALHRJBIHMIAJAA-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- PXRGMZVPWSQAJV-UHFFFAOYSA-N quinazolin-4-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=NC=NC2=C1 PXRGMZVPWSQAJV-UHFFFAOYSA-N 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- STOSPPMGXZPHKP-UHFFFAOYSA-N tetrachlorohydroquinone Chemical compound OC1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl STOSPPMGXZPHKP-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 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
- 238000012546 transfer Methods 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 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
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/001—Acyclic or carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
- C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
- C07C22/08—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/52—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of six-membered aromatic rings being part of condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
본 발명은 유기발광 화합물에 관한 것으로서, 더욱 상세하게는 유기발광소자의 발광층, 전자수송층, 광효율개선층 (Capping layer) 등의 유기물층 재료로 채용되는 것을 특징으로 하는 유기발광 화합물과 이를 채용하여 소자의 저전압 구동 특성 및 발광 효율 등의 발광 특성이 현저히 향상된 유기발광소자에 관한 것이다.The present invention relates to an organic light-emitting compound, and more particularly, an organic light-emitting compound, characterized in that it is employed as an organic material layer material such as a light-emitting layer, an electron transport layer, and a capping layer of an organic light-emitting device, and The present invention relates to an organic light-emitting device having remarkably improved light-emitting characteristics such as low-voltage driving characteristics and light-emitting efficiency.
유기발광소자는 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널 (Plasma Display Panel)이나 무기전계발광 (EL) 디스플레이에 비해 10 V 이하의 저전압 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있고, 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 최근에 차세대 디스플레이 소자로 많은 관심의 대상이 되고 있다.The organic light emitting device can not only form a device on a transparent substrate, but also can drive a low voltage of 10 V or less compared to a plasma display panel or an inorganic electroluminescent (EL) display, and consumes relatively little power. , It has the advantage of excellent color sense, and can display three colors of green, blue, and red, and has recently been a subject of much interest as a next-generation display device.
다만, 이러한 유기발광소자가 상기와 같은 특징으로 발휘하기 위해서는 소자 내 유기물층을 이루는 물질인 정공주입 물질, 정공수송 물질, 발광물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지는 안정하고 효율적인 유기발광소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다.However, in order for such an organic light emitting device to exhibit the above characteristics, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., which are materials that form the organic material layer in the device, are supported by a stable and efficient material. Although this should be preceded, the development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently achieved.
따라서, 더욱 안정적인 유기발광소자를 구현하고, 소자의 고효율, 장수명, 대형화 등을 위해서는 효율 및 수명 특성 측면에서 추가적인 개선이 요구되고 있는 상황이고, 특히 유기발광소자의 각 유기물층을 이루는 소재에 대한 개발이 절실히 필요한 실정이다.Therefore, in order to realize a more stable organic light emitting device and to achieve high efficiency, long life, and large size of the device, further improvement is required in terms of efficiency and lifespan characteristics. In particular, the development of materials constituting each organic material layer of the organic light emitting device is required. The situation is desperately needed.
또한, 최근에는 각 유기물층 재료의 성능 변화를 주어 유기발광소자의 특성을 향상시키는 연구뿐만 아니라, 애노드 (anode)와 캐소드 (cathode) 사이에서 최적화된 광학 두께에 의한 색순도 향상 및 발광 효율 증대 기술이 소자 성능을 향상시키는데 중요한 요소 중의 하나로 착안되고 있으며, 이러한 방법의 일 예로 전극에 캡핑층 (capping layer)을 사용하여 광효율 감소와 우수한 색순도를 거두기도 한다.In addition, in recent years, not only research to improve the characteristics of organic light emitting devices by changing the performance of each organic material layer material, but also technology to improve color purity and luminous efficiency by the optical thickness optimized between the anode and the cathode has been developed. It is being conceived as one of the important factors in improving the performance, and as an example of such a method, a capping layer is used on the electrode to reduce light efficiency and achieve excellent color purity.
따라서, 본 발명은 유기발광소자 내의 유기물층 재료로 채용되어 발광 효율 및 구동 전압 특성 등의 우수한 발광 특성을 구현할 수 있는 신규한 유기발광 화합물 및 이를 포함하는 유기발광소자를 제공하고자 한다.Accordingly, an object of the present invention is to provide a novel organic light-emitting compound and an organic light-emitting device including the same, which can be employed as an organic material layer material in an organic light-emitting device to realize excellent light-emitting characteristics such as luminous efficiency and driving voltage characteristics.
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 Ⅰ]로 표시되고, 이러한 특징적 골격의 Ar1 내지 Ar4에 각각 하기 [구조식 1]를 도입한 것을 특징으로 하는 유기발광 화합물 및 이를 포함하는 유기발광소자를 제공한다.In order to solve the above problems, the present invention is represented by the following [Chemical Formula I], and the following [Structural Formula 1] is introduced into each of Ar 1 to Ar 4 of the characteristic skeleton, and an organic light-emitting compound comprising the same It provides a light emitting device.
[화학식 Ⅰ][Chemical Formula Ⅰ]
[구조식 1][Structural Formula 1]
상기 [화학식 Ⅰ]과 [구조식 1]의 구조 및 치환기에 대해서는 후술한다.The structures and substituents of [Chemical Formula I] and [Structural Formula 1] will be described later.
본 발명에 따른 유기발광 화합물은 유기발광소자 내의 발광층, 전자수송층, 광효율개선층 등의 유기물층 재료로 채용할 경우에 소자의 구동전압 및 발광 효율 등에 있어서 우수한 발광 특성을 구현할 수 있어 다양한 디스플레이 소자에 유용하여 사용될 수 있다.When the organic light-emitting compound according to the present invention is used as an organic material layer material such as a light-emitting layer, an electron transport layer, and a light-efficiency improvement layer in an organic light-emitting device, it is useful for various display devices because it can realize excellent light-emitting characteristics in terms of driving voltage and light-emitting efficiency of the device. Can be used.
도 1은 본 발명에 따른 유기발광 화합물의 구조를 나타낸 대표도이다.1 is a representative diagram showing the structure of an organic light emitting compound according to the present invention.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 유기발광소자의 구동전압 및 발광 효율 등에 있어서 우수한 발광 특성을 거둘 수 있는 하기 [화학식 Ⅰ]로 표시되는 유기발광 화합물에 관한 것이다.The present invention relates to an organic light-emitting compound represented by the following [Chemical Formula I] capable of obtaining excellent light-emitting characteristics in driving voltage and light-emitting efficiency of an organic light-emitting device.
[화학식 Ⅰ][Chemical Formula Ⅰ]
상기 [화학식 Ⅰ]에서,In the above [Chemical Formula I],
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소 및 치환 또는 비치환된 탄소수 1 내지 20의 알킬기 중에서 선택된다.R 1 and R 2 are the same as or different from each other, and each independently selected from deuterium and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
또한, 본 발명에 따른 유기발광 화합물은 상기와 같은 골격의 Ar1 내지 Ar4에 특징적 구조체를 도입한 것으로서 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 하기 [구조식 1]로 표시되는 것으로 구현되는 모이어티를 도입한 것을 특징으로 한다.In addition, the organic light emitting compound according to the present invention is a characteristic structure introduced into Ar 1 to Ar 4 of the skeleton as described above, and Ar 1 to Ar 4 are the same as or different from each other, and each independently represented by the following [Structural Formula 1] It is characterized in that the introduction of a moiety that is implemented as.
[구조식 1][Structural Formula 1]
상기 [구조식 1]에서,In the [Structural Formula 1],
X1 내지 X8은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR이고, 상기 R은 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택된다.X 1 to X 8 are the same as or different from each other, each independently N or CR, wherein R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms It is selected from a group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
또한, 상기 X1 내지 X8 중 어느 하나는 C-*이고, '*'는 상기 Ar1 내지 Ar4 각각과 연결되는 것을 의미한다.In addition, any one of X 1 to X 8 is C-*, and'*' means that each of Ar 1 to Ar 4 is connected.
또한, 본 발명의 일 실시예에 의하면, 상기 Ar1 내지 Ar4는 서로 결합하거나 인접한 치환기와 연결되어 적어도 하나 이상의 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있고, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 질소 원자(N), 황 원자(S) 및 산소 원자 (O) 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있으며, 구체적인 예를 들면 하기와 같은 골격 구조 등을 가질 수 있으며, 이에 한정되는 것은 아니다.In addition, according to an embodiment of the present invention, the Ar 1 to Ar 4 may be bonded to each other or connected with an adjacent substituent to form at least one or more alicyclic, aromatic monocyclic or polycyclic rings, and the formed alicyclic, The carbon atom of an aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from a nitrogen atom (N), a sulfur atom (S) and an oxygen atom (O), and specific examples include the following skeletal structure, etc. It may have, but is not limited thereto.
한편, 본 발명에 따른 화합물에 있어서, '치환 또는 비치환'이란 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 실릴기, 탄소수 1 내지 20의 알킬기, 탄소수 1 내지 20의 할로겐화된 알킬기, 탄소수 3 내지 20의 시클로알킬기, 탄소수 1 내기 20의 알콕시기, 탄소수 1 내지 20의 할로겐화된 알콕시기, 탄소수 2 내지 20의 알케닐기, 탄소수 6 내지 30의 아릴기, 탄소수 3 내지 30의 헤테로아릴기 및 플루오레닐기로 로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.Meanwhile, in the compound according to the present invention,'substituted or unsubstituted' means deuterium, halogen group, cyano group, nitro group, hydroxy group, silyl group, alkyl group having 1 to 20 carbon atoms, halogenated alkyl group having 1 to 20 carbon atoms, carbon number A 3 to 20 cycloalkyl group, a C 1 to C 20 alkoxy group, a C 1 to C 20 halogenated alkoxy group, a C 2 to C 20 alkenyl group, a C 6 to C 30 aryl group, a C 3 to C 30 heteroaryl group, and It means that it is substituted with one or two or more substituents selected from the group consisting of a fluorenyl group, or is substituted with a substituent to which two or more substituents are connected, or does not have any substituents.
구체적인 예를 들면, 치환된 아릴기라 함은, 페닐기, 비페닐기, 나프탈렌기, 플루오레닐기, 파이레닐기, 페난트레닐기, 페릴렌기, 테트라세닐기, 안트라센닐기 등이 다른 1 종 이상의 치환기로 치환된 것을 의미하며, 치환된 헤테로아릴기라 함은, 피리딜기, 티오페닐기, 트리아진기, 퀴놀린기, 페난트롤린기, 이미다졸기, 티아졸기, 옥사졸기, 카바졸기 및 이들의 축합헤테로고리기, 예컨대 벤즈퀴놀린기, 벤즈이미다졸기, 벤즈옥사졸기, 벤즈티아졸기, 벤즈카바졸기, 디벤조티오페닐기, 디벤조퓨란기 등이 다른 1종 이상의 치환기로 치환된 것을 의미한다.For a specific example, the substituted aryl group means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetrasenyl group, an anthracenyl group, etc. are substituted with one or more other substituents. And the substituted heteroaryl group means a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group, and a condensed heterocyclic group thereof, such as It means that a benzquinoline group, a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, and the like are substituted with one or more other substituents.
본 발명에 있어서, 상기 치환기들의 예시들에 대해서 아래에서 구체적으로 설명하나, 이에 한정되는 것은 아니다.In the present invention, examples of the substituents will be described in detail below, but are not limited thereto.
본 발명에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 20인 것이 바람직하다. 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥틸메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이들에 한정되지 않는다.In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cycloheptylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but are not limited thereto.
본 발명에 있어서, 알콕시기는 직쇄 또는 분지쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 입체적 방해를 주지 않는 범위인 1 내지 20개인 것이 바람직하다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, i-프로필옥시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, the alkoxy group may be linear or branched. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferably 1 to 20 carbon atoms in a range that does not cause a steric hindrance. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , Benzyloxy group, p-methylbenzyloxy group, and the like, but are not limited thereto.
본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 30인 것이 바람직하다. 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌(fluoranthrene)기 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group, and examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, and tetrasenyl group. , A chrysenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, a fluoranthrene group, and the like, but the scope of the present invention is not limited to these examples.
본 발명에 있어서, 헤테로아릴기는 이종원자로 O, N 또는 S를 포함하는 헤테로아릴기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 30인 것이 바람직하다. 헤테로아릴기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the heteroaryl group is a heteroaryl group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole 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 triazine group, a triazole 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, dibenzofuranyl group, phenanthroline group, thiazolyl Group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, and the like, but are not limited thereto.
본 발명에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 구체적으로 시클로프로필기 시클로부틸기 시클로펜틸기 3-메틸시클로펜틸기 2,3-디메틸시클로펜틸기, 시클로헥실기, 3-메틸시클로헥실기, 4-메틸시클로헥실기, 2,3-디메틸시클로헥실기, 3,4,5-트리메틸시클로헥실기, 4-tert-부틸시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다.In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, and a cyclohexyl group. Sil group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo There are octyl groups and the like, but are not limited thereto.
본 발명에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 발명에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다.In the present invention, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
또한, 본 발명에 있어서, 플루오레닐기는 2개의 고리 유기 화합물이 1개의 원자를 통하여 연결된 구조로서, 예로는 
상기 [화학식 Ⅰ]로 표시되는 본 발명에 따른 유기발광 화합물은 그 구조적 특이성으로 인하여 유기발광소자의 유기물층으로 사용될 수 있고, 보다 구체적으로는 유기물층 내 발광층, 전자수송층, 광효율개선층 재료로 사용될 수 있다.The organic light-emitting compound according to the present invention represented by [Chemical Formula I] may be used as an organic material layer of an organic light-emitting device due to its structural specificity, and more specifically, as a material for a light-emitting layer, an electron transport layer, and a light efficiency improvement layer in the organic material layer. .
본 발명에 따른 [화학식 Ⅰ]로 표시되는 유기발광 화합물의 바람직한 구체예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred specific examples of the organic light-emitting compound represented by [Chemical Formula I] according to the present invention include the following compounds, but are not limited thereto.
이와 같이, 본 발명에 따른 유기발광 화합물은 특징적인 골격에 치환기 고유의 특성을 갖는 모이어티 (moiety)를 도입하여 다양한 특성을 갖는 유기발광 화합물을 합성할 수 있고, 그 결과 본 발명에 따른 유기발광 화합물을 발광층, 전자수송층, 광효율 개선층 등 다양한 유기물층 물질로 적용할 경우에 소자의 발광효율 등의 발광 특성을 더욱 향상시킬 수 있다.As described above, the organic light-emitting compound according to the present invention can synthesize an organic light-emitting compound having various characteristics by introducing a moiety having inherent characteristics of a substituent to a characteristic skeleton, and as a result, the organic light-emitting compound according to the present invention When the compound is applied as a variety of organic material layer materials such as a light emitting layer, an electron transport layer, and a light efficiency improvement layer, light emission characteristics such as light emission efficiency of the device may be further improved.
또한, 본 발명의 화합물은 일반적인 유기발광소자 제조방법에 따라 소자에 적용할 수 있다.In addition, the compound of the present invention can be applied to a device according to a general method for manufacturing an organic light emitting device.
본 발명의 일 실시예에 따른 유기발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기물층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 유기발광 화합물을 소자의 유기물층에 사용한다는 것을 제외하고는 통상의 소자 제조방법 및 재료를 사용하여 제조될 수 있다.The organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode, a second electrode, and an organic material layer disposed therebetween, and that the organic light emitting compound according to the present invention is used for the organic material layer of the device. Except, it can be manufactured using conventional device manufacturing methods and materials.
본 발명에 따른 유기발광소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 저지층, 정공 저지층, 광효율 개선층(Cappinglayer) 등을 포함하는 구조를 가질 수 있다. 그러나, 이에 한정되지 않고 더 적은 수, 더 많은 수의 유기물층을 포함할 수도 있다.The organic material layer of the organic light emitting device according to 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, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a light efficiency improvement layer, and the like. However, the present invention is not limited thereto, and may include a smaller number or a larger number of organic material layers.
또한, 본 발명의 일 실시예에 따른 유기전기발광소자는 기판, 제1전극(양극), 유기물층, 제2전극(음극) 및 광효율 개선층을 포함하며, 상기 광효율 개선층은 제1 전극 하부 (Bottom emission) 또는 제2 전극 상부(Top emission)에 형성될 수 있다.In addition, the organic electroluminescent device according to an embodiment of the present invention includes a substrate, a first electrode (anode), an organic material layer, a second electrode (cathode), and a light efficiency improvement layer, and the light efficiency improvement layer is a lower portion of the first electrode ( It may be formed on the bottom emission or on the top emission of the second electrode.
제2 전극 상부(Top emission)에 형성되는 방식은 발광층에서 형성된 빛이 캐소드쪽으로 방출되는데 캐소드쪽으로 방출되는 빛이 굴절률이 상대적으로 높은 본 발명에 따른 화합물로 형성된 광효율 개선층(CPL)을 통과하면서 빛의 파장이 증폭되고 따라서 광효율이 상승하게 된다 또한, 제1 전극 하부 (Bottom emission)에 형성되는 방식 역시 마찬가지 원리에 의해 본 발명에 따른 화합물을 광효율 개선층에 채용하여 유기전기소자의 광효율이 향상된다.In the method of forming the top emission of the second electrode, light formed in the light emitting layer is emitted toward the cathode, and the light emitted toward the cathode passes through the light efficiency improvement layer (CPL) formed of the compound according to the present invention having a relatively high refractive index. The wavelength of is amplified and thus the light efficiency is increased. In addition, the method of forming the bottom emission under the first electrode also adopts the compound according to the present invention in the light efficiency improvement layer according to the same principle, so that the light efficiency of the organic electric device is improved. .
본 발명에 따른 바람직한 유기발광소자의 유기물층 구조 등에 대해서는 후술하는 실시예에서 보다 상세하게 설명한다.The structure of the organic material layer of the organic light emitting device according to the present invention will be described in more detail in Examples to be described later.
또한, 본 발명에 따른 유기발광소자는 스퍼터링 (sputtering)이나 전자빔 증발 (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, 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.In addition, the organic light-emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, 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 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기발광소자를 만들 수도 있다. 상기 유기물층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and the like, but is not limited thereto and may have a single layer structure. In addition, the organic material layer is made of a variety of polymeric materials, and is used in a solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.
상기 양극 물질로는 통상 유기물층으로 정공주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, 아연 산화물, 인듐 산화물, 인듐 주석 산화물(ITO), 인듐 아연 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](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the cathode material, a material having a large work function is preferable so that hole injection into the organic material layer can be smoothly performed. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT) , Polypyrrole and conductive polymers such as polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 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.It is preferable that the cathode material is 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, and multilayers such as LiF/Al or LiO 2 /Al Structural materials and the like, but are not limited thereto.
정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene, quinacridone-based organics, perylene-based organics, There are anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.
정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송 받아 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, 본 발명에 따른 유기발광 화합물을 이용하여 소자의 저전압 구동 특성, 발광효율 및 수명 특성을 더욱 향상시킬 수 있다.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion. However, using the organic light-emitting compound according to the present invention, low voltage driving characteristics, luminous efficiency, and lifetime characteristics of the device Can be further improved.
발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3), 카르바졸 계열 화합물, 이량체화 스티릴(dimerized styryl) 화합물, BAlq, 10-히드록시벤조 퀴놀린-금속 화합물, 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물, 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자, 스피로(spiro) 화합물, 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.As a light-emitting material, a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole, and There are benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but are not limited thereto.
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.As the electron 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 mobility for electrons is suitable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline , a complex including Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
본 발명에 따른 유기발광소자는 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 bottom emission type, or a double-sided emission type depending on the material used.
또한, 본 발명에 따른 유기발광 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다.In addition, the organic light-emitting compound according to the present invention can act on a principle similar to that applied to an organic light-emitting device in organic electronic devices, including organic solar cells, organic photoreceptors, and organic transistors.
이하, 본 발명의 이해를 돕기 위하여 바람직한 화합물의 합성예 및 소자 실시예를 제시한다. 그러나, 하기의 실시예는 본 발명을 예시하기 위한 것이며, 이에 의하여 본 발명의 범위가 한정되는 것은 아니다.Hereinafter, synthesis examples and device examples of preferred compounds are presented to aid in understanding the present invention. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereby.
합성예 1 : 화합물 6의 합성Synthesis Example 1: Synthesis of Compound 6
(1) 제조예 1 : 화합물 6의 합성(1) Preparation Example 1: Synthesis of Compound 6
2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), 6-(trifluoromethyl)naphthalen-2-ylboronic acid (25.0 g, 0.104 mol, mascot), potassium carbonate (32.8 g, 0.237 mol, sigma aldrich), Pd(PPh3)4 (5.48 g, 0.005 mol, sigma aldrich), toluene 350 mL와 H2O 80 mL와 ethanol 80 mL를 넣고 95 ℃에서 12시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 6을 14.8 g (수율 70.71%) 수득하였다.2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), 6-(trifluoromethyl)naphthalen-2-ylboronic acid (25.0 g, 0.104 mol, mascot), potassium carbonate (32.8 g, 0.237 mol, sigma aldrich), Pd(PPh 3 ) 4 (5.48 g, 0.005 mol, sigma aldrich), 350 mL of toluene, 80 mL of H 2 O, and 80 mL of ethanol were added, followed by reflux stirring at 95° C. for 12 hours to react. . After completion of the reaction, extraction was performed and column purification was performed to obtain 14.8 g of compound 6 (yield 70.71%).
H-NMR (200 MHz, CDCl3):δ ppm, 2H(2.34/s), 4H(8.23/d, 8.12/s, 7.95/d, 7.92/d, 7.62/d, 7.58/d)H-NMR (200 MHz, CDCl3): δ ppm, 2H (2.34/s), 4H (8.23/d, 8.12/s, 7.95/d, 7.92/d, 7.62/d, 7.58/d)
LC/MS: m/z=882[(M+1)+]LC/MS: m/z=882[(M+1) + ]
합성예 2 : 화합물 21의 합성Synthesis Example 2: Synthesis of Compound 21
(1) 제조예 1 : 화합물 21의 합성(1) Preparation Example 1: Synthesis of Compound 21
1,4-di-tert-butyl-2,3,5,6-tetrachlorobenzene (10 g, 0.031 mol, mascot), 3-methylnaphthalen-1-ylboronic acid (24.9 g, 0.134 mol, mascot), potassium carbonate (42.1 g, 0.3075 mol, sigma aldrich), 촉매 Pd(OAc)2 (4.23 g, 0.004 mol, sigma aldrich), 리간드 X-Phos (5.8 g, 0.012 mol, sigma aldrich)에 THF 350 mL와 H2O 80 mL와 ethanol 80 mL를 넣고 80 ℃에서 16시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 21을 15.1 g (수율 65.6%) 수득하였다.1,4-di-tert-butyl-2,3,5,6-tetrachlorobenzene (10 g, 0.031 mol, mascot), 3-methylnaphthalen-1-ylboronic acid (24.9 g, 0.134 mol, mascot), potassium carbonate ( 42.1 g, 0.3075 mol, sigma aldrich), catalyst Pd(OAc) 2 (4.23 g, 0.004 mol, sigma aldrich), ligand X-Phos (5.8 g, 0.012 mol, sigma aldrich) in THF 350 mL and H 2 O 80 mL and 80 mL of ethanol were added, and the mixture was stirred under reflux at 80° C. for 16 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 15.1 g (65.6% yield) of compound 21.
H-NMR (200 MHz, CDCl3):δ ppm, 4H(8.56/d, 8.05/d, 7.95/s, 7.93/s, 7.54/m, 7.51/m, 2.45/m), 6H(1.35/m)H-NMR (200 MHz, CDCl3): δ ppm, 4H (8.56/d, 8.05/d, 7.95/s, 7.93/s, 7.54/m, 7.51/m, 2.45/m), 6H (1.35/m)
LC/MS: m/z=750[(M+1)+]LC/MS: m/z=750[(M+1) + ]
합성예 3 : 화합물 22의 합성Synthesis Example 3: Synthesis of Compound 22
(1) 제조예 1 : 화합물 22의 합성(1) Preparation Example 1: Synthesis of Compound 22
1,2,4,5-tetrachlorobenzene-d2 (10 g, 0.046 mol, mascot), 2-naphthylboronic acid (34.7 g, 0.202 mol, mascot), potassium carbonate (63.4 g, 0.459 mol, sigma aldrich), 촉매 Pd(OAc)2 (6.36 g, 0.006 mol, sigma aldrich), 리간드 X-Phos (8.8 g, 0.018 mol, sigma aldrich), THF 450 mL와 H2O 100 mL와 ethanol 100 mL를 넣고 95 ℃에서 17시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 22를 18.2 g (수율 67.8%) 수득하였다.1,2,4,5-tetrachlorobenzene-d2 (10 g, 0.046 mol, mascot), 2-naphthylboronic acid (34.7 g, 0.202 mol, mascot), potassium carbonate (63.4 g, 0.459 mol, sigma aldrich), catalyst Pd Add (OAc) 2 (6.36 g, 0.006 mol, sigma aldrich), ligand X-Phos (8.8 g, 0.018 mol, sigma aldrich), 450 mL of THF, 100 mL of H 2 O, and 100 mL of ethanol at 95 ℃ for 17 hours It was reacted by stirring during reflux. After completion of the reaction, extraction was performed and column purification was performed to give 18.2 g (67.8% yield) of compound 22.
H-NMR (200MHz, CDCl3):δppm, 4H(7.92/d, 7.73/d, 7.58/d), 8H(8.00/d, 7.59/m)H-NMR (200MHz, CDCl3): δppm, 4H (7.92/d, 7.73/d, 7.58/d), 8H (8.00/d, 7.59/m)
LC/MS: m/z=584[(M+1)+]LC/MS: m/z=584[(M+1) + ]
합성예 4 : 화합물 28의 합성Synthesis Example 4: Synthesis of Compound 28
(1) 제조예 1 : 화합물 28의 합성(1) Preparation Example 1: Synthesis of Compound 28
2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), naphthylboronic acid (17.9 g, 0.104 mol, sigma aldrich), potassium carbonate (32.8 g, 0.237 mol, sigma aldrich), Pd(PPh3)4 (5.48 g, 0.005 mol, sigma aldrich), toluene 300 mL와 H2O 70 mL와 ethanol 70 mL를 넣고 95 ℃에서 17시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 28을 12.1 g (수율 83.6%) 수득하였다.2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), naphthylboronic acid (17.9 g, 0.104 mol, sigma aldrich), potassium carbonate (32.8 g, 0.237 mol, sigma aldrich), Pd (PPh 3 ) 4 (5.48 g, 0.005 mol, sigma aldrich), 300 mL of toluene, 70 mL of H 2 O, and 70 mL of ethanol were added, followed by reflux stirring at 95° C. for 17 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 12.1 g (83.6% yield) of compound 28.
H-NMR (200MHz, CDCl3):δppm, 2H(2.34/s), 4H(8.55/d, 8.42/d, 8.08/d, 8.04/d, 7.61/m), 8H(7.55/m)H-NMR (200MHz, CDCl3): δppm, 2H(2.34/s), 4H(8.55/d, 8.42/d, 8.08/d, 8.04/d, 7.61/m), 8H(7.55/m)
LC/MS: m/z=610[(M+1)+]LC/MS: m/z=610[(M+1) + ]
합성예 5 : 화합물 35의 합성Synthesis Example 5: Synthesis of Compound 35
(1) 제조예 1 : 화합물 35의 합성(1) Preparation Example 1: Synthesis of Compound 35
1,4-di-tert-butyl-2,3,5,6-tetrachlorobenzene (10 g, 0.031 mol, mascot), 6-Phenylnaphthalene-2-boronic acid (33.3 g, 0.134 mol, alfa aesar), potassium carbonate (42.1 g, 0.305 mol, sigma aldrich), 촉매 Pd(OAc)2 (4.23 g, 0.004 mol, sigma aldrich), 리간드 X-Phos (5.8 g, 0.012 mol, sigma aldrich)에 THF 500 mL, ethanol 120 mL, H2O 120 mL 넣고 90 ℃에서 10시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 35를 19.3 g (수율63.4%) 수득하였다.1,4-di-tert-butyl-2,3,5,6-tetrachlorobenzene (10 g, 0.031 mol, mascot), 6-Phenylnaphthalene-2-boronic acid (33.3 g, 0.134 mol, alfa aesar), potassium carbonate (42.1 g, 0.305 mol, sigma aldrich), catalyst Pd(OAc) 2 (4.23 g, 0.004 mol, sigma aldrich), ligand X-Phos (5.8 g, 0.012 mol, sigma aldrich) in THF 500 mL, ethanol 120 mL Then, 120 mL of H 2 O was added and reacted by refluxing at 90° C. for 10 hours. After completion of the reaction, extraction was performed and column purification was performed to obtain 19.3 g (63.4% yield) of compound 35.
H-NMR (200MHz, CDCl3):δppm, 4H(7.41/m), 6H(1.35/m), 8H(7.92/d, 7.73/d, 7.58/m, 7.52/d, 7.51/m)H-NMR (200MHz, CDCl3): δppm, 4H(7.41/m), 6H(1.35/m), 8H(7.92/d, 7.73/d, 7.58/m, 7.52/d, 7.51/m)
LC/MS: m/z=998[(M+1)+]LC/MS: m/z=998[(M+1) + ]
합성예 6 : 화합물 41의 합성Synthesis Example 6: Synthesis of Compound 41
(1) 제조예 1 : 화합물 41의 합성(1) Preparation Example 1: Synthesis of Compound 41
1,2,4,5-tetrachlorobenzene-d2 (10 g, 0.046 mol, mascot), 4-methoxynaphthalen-1-ylboronic acid (40.8 g, 0.202 mol, mascot), potassium carbonate (63.4 g, 0.459 mol, sigma aldrich), 촉매 Pd(OAc)2 (6.36 g, 0.006 mol, sigma aldrich), 리간드 X-Phos (8.8 g, 0.018 mol, sigma aldrich)에 THF 500 mL, ethanol 120 mL, H2O 120 mL 넣고 90 ℃에서 10시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 41을 24.9 g (수율 77.0%) 수득하였다.1,2,4,5-tetrachlorobenzene-d2 (10 g, 0.046 mol, mascot), 4-methoxynaphthalen-1-ylboronic acid (40.8 g, 0.202 mol, mascot), potassium carbonate (63.4 g, 0.459 mol, sigma aldrich ), catalyst Pd(OAc) 2 (6.36 g, 0.006 mol, sigma aldrich), ligand X-Phos (8.8 g, 0.018 mol, sigma aldrich) in THF 500 mL, ethanol 120 mL, H 2 O 120 mL and 90 ℃ The reaction was carried out by stirring at reflux for 10 hours. After completion of the reaction, extraction was performed and column purification was performed to obtain 24.9 g (77.0% yield) of compound 41.
H-NMR (200MHz, CDCl3):δppm, 4H(8.54/d, 8.31/d, 7.86/d, 7.59/m, 7.58/m, 6.71/d, 3.83/s)H-NMR (200MHz, CDCl3): δppm, 4H (8.54/d, 8.31/d, 7.86/d, 7.59/m, 7.58/m, 6.71/d, 3.83/s)
LC/MS: m/z=998[(M+1)+]LC/MS: m/z=998[(M+1) + ]
합성예 7 : 화합물 53의 합성Synthesis Example 7: Synthesis of Compound 53
(1) 제조예 1 : 중간체 53-1의 합성(1) Preparation Example 1: Synthesis of Intermediate 53-1
Tetrachlorohydroquinone (10 g, 0.040 mol, TCI)을 CH2Cl2 300 mL에 녹인 후 pyridine (6.47 mL, 0.080 mol)을 0 ℃에서 첨가하였다. Trifluoromethanesulfonic anhydride (25.04 g, 0.089 mol, sigma aldrich)을 천천히 적가한 후 상온으로 올려 반응시켰다. 약 1시간 후 ethanol에 녹여 10% HCl 용액으로 quenching후 추출하고 컬럼 정제하여 <중간체 53-1>을 18.1 g (수율 87.6%) 수득하였다.Tetrachlorohydroquinone (10 g, 0.040 mol, TCI) into CH 2 Cl 2 After dissolving in 300 mL, pyridine (6.47 mL, 0.080 mol) was added at 0 °C. Trifluoromethanesulfonic anhydride (25.04 g, 0.089 mol, sigma aldrich) was slowly added dropwise and then heated to room temperature for reaction. After about 1 hour, it was dissolved in ethanol, quenched with 10% HCl solution, extracted and purified by column to give 18.1 g (yield 87.6%) of <Intermediate 53-1>.
(2) 제조예 2 : 중간체 53-2의 합성(2) Preparation Example 2: Synthesis of Intermediate 53-2
중간체 53-1 (10 g, 0.020 mol), isopropylboronic acid (7.55 g, 0.086 mol, sigma aldrich), tripotassium phosphate (41.5 g, 0.195 mol, sigma aldrich), 촉매 Pd2(dba)3 (3.58 g, 0.004 mol, sigma aldrich), 리간드 S-Phos (16.0 g, 0.039 mol, sigma aldrich)에 toluene 200 mL을 넣고 90 ℃ 에서 16시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 <중간체 53-2>를 3.4 g (수율 58.0%) 수득하였다.Intermediate 53-1 (10 g, 0.020 mol), isopropylboronic acid (7.55 g, 0.086 mol, sigma aldrich), tripotassium phosphate (41.5 g, 0.195 mol, sigma aldrich), catalyst Pd 2 (dba) 3 (3.58 g, 0.004 mol, sigma aldrich), ligand S-Phos (16.0 g, 0.039 mol, sigma aldrich) was added to 200 mL of toluene and stirred under reflux at 90° C. for 16 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 3.4 g (yield 58.0%) of <Intermediate 53-2>.
(3) 제조예 3 : 화합물 53의 합성(3) Preparation Example 3: Synthesis of Compound 53
중간체 53-2 (10 g, 0.033 mol), 2-Naphthylboronic acid (25.2 g, 0.147 mol, sigma aldrich), potassium carbonate (46.1 g, 0.333 mol, sigma aldrich), 촉매 Pd(OAc)2 (4.62 g, 0.004 mol, sigma aldrich), 리간드 X-Phos (6.36 g, 0.013 mol, sigma aldrich)에 THF 350 mL, ethanol 80 mL, H2O 80 mL 넣고 90 ℃에서 17시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 53을 16.7 g (수율 75.1%) 수득하였다.Intermediate 53-2 (10 g, 0.033 mol), 2-Naphthylboronic acid (25.2 g, 0.147 mol, sigma aldrich), potassium carbonate (46.1 g, 0.333 mol, sigma aldrich), catalyst Pd(OAc) 2 (4.62 g, 0.004 mol, sigma aldrich) and ligand X-Phos (6.36 g, 0.013 mol, sigma aldrich) were added to 350 mL of THF, 80 mL of ethanol, and 80 mL of H 2 O, and stirred at 90° C. for 17 hours under reflux to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 16.7 g of compound 53 (yield 75.1%).
H-NMR (200MHz, CDCl3):δppm, 2H(2.87/s), 4H(7.92/d, 7.73/d, 7.58/s, 1.20/m), 8H(8.00/d, 7.59/m)H-NMR (200MHz, CDCl3): δppm, 2H(2.87/s), 4H(7.92/d, 7.73/d, 7.58/s, 1.20/m), 8H(8.00/d, 7.59/m)
LC/MS: m/z=666[(M+1)+]LC/MS: m/z=666[(M+1) + ]
합성예 8 : 화합물 60의 합성Synthesis Example 8: Synthesis of Compound 60
(1) 제조예 1 : 화합물 60의 합성(1) Preparation Example 1: Synthesis of Compound 60
2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), 6-methylquinolin-3-ylboronic acid (19.5 g, 0.104 mol, mascot), potassium carbonate (32.8 g, 0.237 mol, sigma aldrich), 촉매 Pd(PPh3)4 (5.5 g, 0.005 mol, sigma aldrich)에 toluene 300 mL, ethanol 70 mL, H2O 70 mL 넣고 90 ℃ 에서 19시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 60을 10.9 g (수율 68.5%) 수득하였다.2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), 6-methylquinolin-3-ylboronic acid (19.5 g, 0.104 mol, mascot), potassium carbonate (32.8 g, 0.237 mol, sigma aldrich), catalyst Pd(PPh 3 ) 4 (5.5 g, 0.005 mol, sigma aldrich) was added toluene 300 mL, ethanol 70 mL, H 2 O 70 mL, and stirred under reflux at 90° C. for 19 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 10.9 g (68.5% yield) of compound 60.
H-NMR (200MHz, CDCl3):δppm, 4H(8.53/s, 8.19/s, 7.92/d, 7.66/s, 7.51/d), 6H(2.34/m)H-NMR (200MHz, CDCl3): δppm, 4H(8.53/s, 8.19/s, 7.92/d, 7.66/s, 7.51/d), 6H(2.34/m)
LC/MS: m/z=670[(M+1)+]LC/MS: m/z=670[(M+1) + ]
합성예 9 : 화합물 78의 합성Synthesis Example 9: Synthesis of Compound 78
(1) 제조예 1 : 화합물 78의 합성(1) Preparation Example 1: Synthesis of Compound 78
1,4-di-tert-butyl-2,3,5,6-tetrachlorobenzene (10 g, 0.031 mol, mascot), quinazolin-4-ylboronic acid (23.3 g, 0.134 mol, mascot), potassium carbonate (42.1 g, 0.305 mol, sigma aldrich), 촉매 Pd(OAc)2 (4.23 g, 0.004 mol, sigma aldrich), 리간드 X-Phos (5.8 g, 0.012 mol, sigma aldrich)에 THF 300 mL, ethanol 70 mL, H2O 70 mL 넣고 90 ℃에서 13시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 78을 13.5 g (수율 63.0%) 수득하였다.1,4-di-tert-butyl-2,3,5,6-tetrachlorobenzene (10 g, 0.031 mol, mascot), quinazolin-4-ylboronic acid (23.3 g, 0.134 mol, mascot), potassium carbonate (42.1 g , 0.305 mol, sigma aldrich), catalyst Pd(OAc) 2 (4.23 g, 0.004 mol, sigma aldrich), ligand X-Phos (5.8 g, 0.012 mol, sigma aldrich) in THF 300 mL, ethanol 70 mL, H 2 Into 70 mL of O, the mixture was stirred under reflux at 90° C. for 13 hours to react. After completion of the reaction, extraction was performed and column purification was performed to obtain 13.5 g (63.0% yield) of compound 78.
H-NMR (200MHz, CDCl3):δppm, 4H(9.33/s, 8.16/d, 7.84/m, 7.83/m, 7.58/m), 6H(1.35/m)H-NMR (200MHz, CDCl3): δppm, 4H (9.33/s, 8.16/d, 7.84/m, 7.83/m, 7.58/m), 6H (1.35/m)
LC/MS: m/z=702[(M+1)+]LC/MS: m/z=702[(M+1) + ]
합성예 10 : 화합물 85의 합성Synthesis Example 10: Synthesis of Compound 85
(1) 제조예 1 : 화합물 85의 합성(1) Preparation Example 1: Synthesis of Compound 85
1,2,4,5-tetrabromo-3,6-diethylbenzene (10 g, 0.022 mol, mascot), 1,8-naphthyridin-4-ylboronic acid (17.0 g, 0.098 mol, mascot), potassium carbonate (30.7 g, 0.222 mol, sigma aldrich), 촉매 Pd(PPh3)4 (5.14 g, 0.004 mol, sigma aldrich)에 toluene 300 mL, ethanol 70 mL, H2O 70 mL를 넣고 90 ℃에서 12시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 85를 10.4 g (수율 72.3%) 수득하였다.1,2,4,5-tetrabromo-3,6-diethylbenzene (10 g, 0.022 mol, mascot), 1,8-naphthyridin-4-ylboronic acid (17.0 g, 0.098 mol, mascot), potassium carbonate (30.7 g , 0.222 mol, sigma aldrich), catalyst Pd(PPh 3 ) 4 (5.14 g, 0.004 mol, sigma aldrich) was added toluene 300 mL, ethanol 70 mL, H 2 O 70 mL, and stirred under reflux for 12 hours at 90°C. Reacted. After completion of the reaction, extraction was performed and column purification was performed to obtain 10.4 g (72.3% yield) of compound 85.
H-NMR (200MHz, CDCl3):δppm, 2H(2.60/m, 1.25/m), 4H(8.76/d, 8.70/d, 8.39/d, 7.67,d, 7.41/m)H-NMR (200MHz, CDCl3): δppm, 2H (2.60/m, 1.25/m), 4H (8.76/d, 8.70/d, 8.39/d, 7.67,d, 7.41/m)
LC/MS: m/z=646[(M+1)+]LC/MS: m/z=646[(M+1) + ]
합성예 11 : 화합물 91의 합성Synthesis Example 11: Synthesis of Compound 91
(1) 제조예 1 : 화합물 91의 합성(1) Preparation Example 1: Synthesis of Compound 91
2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), 2-tert-butylquinolin-3-ylboronic acid (23.2 g, 0.104 mol, mascot), potassium carbonate (32.8 g, 0.237 mol, sigma aldrich), 촉매 Pd(PPh3)4 (5.5 g, 0.005 mol, sigma aldrich)에 toluene 300 mL, ethanol 70 mL, H2O 70 mL를 넣고 90 ℃에서 11시간 동안 환류 교반하여 반응시켰다. 반응 종료 후 추출한 후 컬럼 정제하여 화합물 91을 13.9 g (수율 69.9%) 수득하였다.2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), 2-tert-butylquinolin-3-ylboronic acid (23.2 g, 0.104 mol, mascot), potassium carbonate (32.8 g, 0.237 mol, sigma aldrich), catalyst Pd (PPh 3 ) 4 (5.5 g, 0.005 mol, sigma aldrich) toluene 300 mL, ethanol 70 mL, H 2 O 70 mL was added to the reaction by reflux stirring at 90 ℃ for 11 hours. . After completion of the reaction, extraction was performed and column purification was performed to obtain 13.9 g (69.9% yield) of compound 91.
H-NMR (200MHz, CDCl3):δppm, 2H(2.34/m) 4H(8.16/s, 8.07/d, 7.95/d, 7.77/m, 7.56/m), 12H(1.35/m)H-NMR (200MHz, CDCl3): δppm, 2H(2.34/m) 4H(8.16/s, 8.07/d, 7.95/d, 7.77/m, 7.56/m), 12H(1.35/m)
LC/MS: m/z=839[(M+1)+]LC/MS: m/z=839[(M+1) + ]
합성예 12 : 화합물 107의 합성Synthesis Example 12: Synthesis of Compound 107
(1) 제조예 1 : 화합물 107의 합성(1) Preparation Example 1: Synthesis of Compound 107
중간체 53-2 (10 g, 0.033 mol), 3-phenylquinolin-6-ylboronic acid (36.5 g, 0.147 mol, mascot), potassium carbonate (46.1 g, 0.333 mol, sigma aldrich), 촉매 Pd(OAc)2 (4.62 g, 0.004 mol, sigma aldrich), 리간드 X-Phos (6.36 g, 0.013 mol, sigma aldrich)에 THF 500 mL, ethanol 120 mL, H2O 120 mL를 넣고 100 ℃에서 15시간 동안 환류 교반하여 반응시켰다. 반응 종료 추출한 후 컬럼 정제하여 화합물 107을 23.8 g (수율 73.2%) 수득하였다.Intermediate 53-2 (10 g, 0.033 mol), 3-phenylquinolin-6-ylboronic acid (36.5 g, 0.147 mol, mascot), potassium carbonate (46.1 g, 0.333 mol, sigma aldrich), catalyst Pd(OAc) 2 ( 4.62 g, 0.004 mol, sigma aldrich), and the ligand X-Phos (6.36 g, 0.013 mol, sigma aldrich) were added 500 mL of THF, 120 mL of ethanol, and 120 mL of H 2 O, followed by reflux stirring at 100 °C for 15 hours to react. Made it. After completion of the reaction, extraction was performed and column purification was performed to obtain 23.8 g (73.2% yield) of compound 107.
H-NMR (200MHz, CDCl3):δppm, 2H(2.87/m), 4H(8.57/s, 8.22/s, 8.21/d, 8.04/d, 7.90/s, 7.41/m), 8H(7.52/d, 7.51/m, 1.20/m)H-NMR (200MHz, CDCl3): δppm, 2H(2.87/m), 4H(8.57/s, 8.22/s, 8.21/d, 8.04/d, 7.90/s, 7.41/m), 8H(7.52/d , 7.51/m, 1.20/m)
LC/MS: m/z=974[(M+1)+]LC/MS: m/z=974[(M+1) + ]
합성예 13 : 화합물 110의 합성Synthesis Example 13: Synthesis of Compound 110
(1) 제조예 1 : 화합물 110의 합성(1) Preparation Example 1: Synthesis of Compound 110
2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), pyrido[2,3-b]pyrazin-7-ylboronic acid (18.3 g, 0.104 mol, mascot), potassium carbonate (32.8 g, 0.237 mol, sigma aldrich), 촉매 Pd(PPh3)4 (5.48 g, 0.005 mol, sigma aldrich)에 toluene 300 mL, ethanol 70 mL, H2O 70 mL를 넣고 100 ℃에서 18시간 동안 환류 교반하여 반응시켰다. 반응 종료 추출한 후 컬럼 정제하여 화합물 110을 12.1 g (수율 82.0%) 수득하였다.2,3,5,6-Tetrabromo-p-xylene (10 g, 0.024 mol, TCI), pyrido[2,3-b]pyrazin-7-ylboronic acid (18.3 g, 0.104 mol, mascot), potassium carbonate ( 32.8 g, 0.237 mol, sigma aldrich), catalyst Pd(PPh 3 ) 4 (5.48 g, 0.005 mol, sigma aldrich) in toluene 300 mL, ethanol 70 mL, H 2 O 70 mL, and refluxed for 18 hours at 100 ℃ It was stirred and reacted. After the reaction was completed, extraction was performed and column purification was performed to obtain 12.1 g (82.0% yield) of compound 110.
H-NMR (200MHz, CDCl3):δppm, 2H(2.34/s), 4H(9.24/s, 7.97/s), 8H(8.63/d)H-NMR (200MHz, CDCl3): δppm, 2H(2.34/s), 4H(9.24/s, 7.97/s), 8H(8.63/d)
LC/MS: m/z=622[(M+1)+]LC/MS: m/z=622[(M+1) + ]
소자 실시예 (HOST)Device Example (HOST)
본 발명에 따른 실시예에서 ITO 투명 전극은 25 mm × 25 mm × 0.7 mm의 ITO 투명 전극이 부착된 유리 기판을 이용하여, 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 베이스 압력이 1 × 10-6 torr 이상 되도록 한 후 상기 ITO 기판 위에 하기 구조로 유기물과 금속을 증착하였다.In the embodiment according to the present invention, the ITO transparent electrode was washed after patterning so that the light emitting area had a size of 2 mm × 2 mm using a glass substrate to which an ITO transparent electrode of 25 mm × 25 mm × 0.7 mm is attached. After the substrate was mounted in a vacuum chamber, the base pressure was 1 × 10 -6 torr or more, and then organic materials and metals were deposited on the ITO substrate in the following structure.
소자 실시예 1 내지 7Device Examples 1 to 7
본 발명에 따라 구현되는 [화합물 6, 15, 22, 29, 35, 42, 53]을 발광층의 호스트 화합물로 사용하였으며, 하기와 같은 소자 구조를 갖는 청색 유기발광소자를 제작하여 전류 효율을 포함한 발광 특성을 측정하였다.[Compounds 6, 15, 22, 29, 35, 42, 53] implemented according to the present invention were used as the host compound of the emission layer, and a blue organic light emitting device having the following device structure was manufactured to emit light including current efficiency. The properties were measured.
ITO / 정공주입층 (HAT-CN 5 nm) / 정공수송층 (α-NPB 100 nm) / 전자저지층 (EBL1 10 nm) / 발광층 (20 nm) / 전자수송층 (201:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)ITO / hole injection layer (HAT-CN 5 nm) / hole transport layer (α-NPB 100 nm) / electron blocking layer (EBL1 10 nm) / emitting layer (20 nm) / electron transport layer (201:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)
ITO 투명 전극 상부에 정공주입층을 형성하기 위해 [HAT-CN]을 5 nm의 두께로 성막하고, 이후 정공수송층은 [α-NPB]를 사용하여 100 nm 성막하였다. 정공저지층은 [EBL1]을 사용하여 10 nm의 두께로 증착하였다. 또한, 발광층은 본 발명에 따른 [화합물 6, 15, 22, 29, 35, 42, 53]을 호스트로 사용하고, 도판트 화합물은 [BD1]을 사용하여 20 nm 두께로 증착하였다. 추가로 전자수송층 (하기 [201] 화합물 Liq 50% 도핑) 30 nm 성막하였다. LiF 1 nm, Al 100 nm를 성막하여 유기발광소자를 제작하였다.In order to form a hole injection layer on the ITO transparent electrode, [HAT-CN] was deposited to a thickness of 5 nm, and then, the hole transport layer was deposited at 100 nm using [α-NPB]. The hole blocking layer was deposited to a thickness of 10 nm using [EBL1]. In addition, the light emitting layer was deposited using [Compounds 6, 15, 22, 29, 35, 42, 53] according to the present invention as a host, and the dopant compound was deposited to a thickness of 20 nm using [BD1]. Further, an electron transport layer (following [201] compound Liq doped 50%) 30 nm was formed. 1 nm of LiF and 100 nm of Al were formed to fabricate an organic light-emitting device.
소자 비교예 1Device Comparative Example 1
소자 비교예 1을 위한 유기발광소자는 상기 실시예 1 내지 7의 소자구조에서 발광층의 호스트 물질로 본 발명에 따른 화합물 대신 BH1을 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 1 was fabricated in the same manner as in the device structures of Examples 1 to 7 except that BH1 was used instead of the compound according to the present invention as the host material of the emission layer.
실험예 1: 소자 실시예 1 내지 7의 발광 특성Experimental Example 1: Light emission characteristics of device Examples 1 to 7
상기 실시예에 따라 제조된 유기발광소자는 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 구동 전압, 전류 효율 및 색좌표를 측정하였고, 1,000 nit 기준의 결과값은 하기 [표 1]와 같다.The organic light-emitting device manufactured according to the above example measured driving voltage, current efficiency, and color coordinates using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the result value based on 1,000 nit. Is as shown in the following [Table 1].
상기 [표 1]에 나타낸 결과를 살펴보면, 본 발명에 따른 화합물을 발광층의 호스트에 적용한 소자의 경우 종래 소자 (비교예 1)에 비하여 구동 전압이 감소하고, 전류 효율이 현저히 우수함을 확인할 수 있다.Looking at the results shown in Table 1, it can be seen that in the case of a device in which the compound according to the present invention is applied to the host of the emission layer, the driving voltage is reduced and the current efficiency is remarkably superior compared to the conventional device (Comparative Example 1).
[HAT-CN] [α-NPB] [EBL1] [BH1] [BD1][HAT-CN] [α-NPB] [EBL1] [BH1] [BD1]
[201][201]
소자 실시예 (ETL)Device Example (ETL)
본 발명에 따른 실시예에서 ITO 투명 전극은 25 mm × 25 mm × 0.7 mm의 유리 기판 위에, ITO 투명 전극이 부착된 ITO 유리 기판을 이용하여, 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착하여 공정 압력이 1 × 10-6 torr 이상 되도록 한 후 ITO 기판 위에 각 기능층과 금속을 증착하였다.In the embodiment according to the present invention, the ITO transparent electrode was patterned to have a light emitting area of 2 mm × 2 mm on a glass substrate of 25 mm × 25 mm × 0.7 mm, using an ITO glass substrate with an ITO transparent electrode attached thereto. After washing. The substrate was mounted in a vacuum chamber so that the process pressure was 1 × 10 -6 torr or higher, and each functional layer and metal were deposited on the ITO substrate.
소자 실시예 8 내지 13Device Examples 8 to 13
본 발명에 따른 [화학식 60, 78, 85, 89, 100, 115]로 구현되는 화합물을 전자수송층에 사용하였으며, 하기와 같은 소자 구조를 갖는 청색 발광 유기발광소자를 제조하여, 발광 효율을 포함한 발광 특성을 측정하였다.The compound represented by [Chemical Formulas 60, 78, 85, 89, 100, 115] according to the present invention was used in the electron transport layer, and a blue light emitting organic light emitting device having the following device structure was manufactured, and light emission including luminous efficiency The properties were measured.
ITO / 정공주입층 (HAT-CN 5 nm) / 정공수송층 (α-NPB 100 nm) / 전자저지층 (EBL1 10 nm) / 발광층 (BH1:BD1 20 nm) / 전자수송층 (화합물:Liq 30 nm) / LiF (1 nm) / Al (100 nm)ITO / hole injection layer (HAT-CN 5 nm) / hole transport layer (α-NPB 100 nm) / electron blocking layer (EBL1 10 nm) / emitting layer (BH1:BD1 20 nm) / electron transport layer (compound: Liq 30 nm) / LiF (1 nm) / Al (100 nm)
ITO 투명 전극에 정공주입층을 형성하기 위해 [HAT-CN]을 5 nm의 두께로 성막하고, 정공수송층으로 α-NPB를 100 nm, 전자저지층은 [EBL1]을 사용하여 10 nm의 두께로 성막하였다. 또한, 발광층에는 호스트 화합물로는 [BH1]을 사용하고, 도판트 화합물로 [BD1]을 사용하여 두께가 20 nm가 되도록 성막하였으며, 추가로 전자 수송층은 본 발명에 따른 [화합물 60, 78, 85, 89, 100, 115]를 사용하여 30 nm (Liq 도핑) 두께로 성막하였다. 마지막으로 LiF 1 nm 및 Al 100 nm로 성막하여 유기발광소자를 제작하였다.To form a hole injection layer on the ITO transparent electrode, [HAT-CN] was deposited to a thickness of 5 nm, and α-NPB was used as a hole transport layer to a thickness of 10 nm, and [EBL1] was used for the electron blocking layer. The tabernacle was made. In addition, [BH1] was used as the host compound for the light emitting layer, and [BD1] was used as the dopant compound to form a film to have a thickness of 20 nm. , 89, 100, 115] to a thickness of 30 nm (Liq doping). Finally, an organic light emitting device was fabricated by forming a film with 1 nm of LiF and 100 nm of Al.
소자 비교예 2Element Comparative Example 2
소자 비교예 2를 위한 유기발광소자는 상기 실시예 8 내지 13의 소자구조에서 전자수송층을 본 발명으로 구현되는 화합물 대신 201을 사용한 것을 제외하고 동일하게 제작하였다.The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner as in the device structures of Examples 8 to 13, except that the electron transport layer 201 was used instead of the compound embodied in the present invention.
실험예 2 : 소자 실시예 8 내지 13의 발광 특성Experimental Example 2: Light emission characteristics of device Examples 8 to 13
상기 실시예 및 비교예에 따라 제조된 유기발광소자는 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 구동 전압, 전류 효율을 측정하였다. 1,000 nit 기준의 결과값은 하기 [표 2]와 같다.In the organic light emitting device manufactured according to the above Examples and Comparative Examples, driving voltage and current efficiency were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research). The result values based on 1,000 nit are shown in Table 2 below.
상기 [표 2]에 나타낸 결과를 살펴보면, 본 발명에 따른 화합물을 전자수송층으로 소자에 적용한 경우에 종래 소자 (비교예 2)에 비해 구동 전압이 감소하고, 전류 효율이 현저히 향상되는 것을 확인할 수 있다.Looking at the results shown in [Table 2], it can be seen that when the compound according to the present invention is applied to a device as an electron transport layer, compared to the conventional device (Comparative Example 2), the driving voltage is reduced and the current efficiency is remarkably improved. .
[HAT-CN] [α-NPB] [EBL1] [BH1] [BD1][HAT-CN] [α-NPB] [EBL1] [BH1] [BD1]
[201][201]
소자 실시예 (CPL)Device Example (CPL)
본 발명에 따른 실시예에서 ITO 투명 전극은 25 mm × 25 mm × 0.7 mm의 Ag를 포함하는 ITO 유리 기판을 이용하여, 발광 면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 베이스 압력이 1 × 10-6 torr 이상 되도록 한 후 상기 Ag를 포함하는 ITO 유리 기판 위에 하기 구조로 유기물과 금속을 증착하였다.In the embodiment according to the present invention, the ITO transparent electrode was washed after patterning so that the light emitting area was 2 mm × 2 mm using an ITO glass substrate containing Ag of 25 mm × 25 mm × 0.7 mm. After mounting the substrate in the vacuum chamber, the base pressure was 1 × 10 -6 torr or more, and then organic substances and metals were deposited on the ITO glass substrate containing Ag in the following structure.
소자 실시예 14 내지 22Device Examples 14 to 22
본 발명에 따라 구현되는 [화합물 21, 28, 41, 55, 67, 91, 101, 107, 110]을 광효율 개선층 화합물로 사용하였으며, 하기와 같은 소자 구조를 갖는 청색 유기발광소자를 제작하여, 발광 효율을 포함한 발광 특성을 측정하였다.[Compounds 21, 28, 41, 55, 67, 91, 101, 107, 110] implemented according to the present invention were used as the light efficiency improvement layer compound, and a blue organic light emitting device having the following device structure was manufactured, The luminescence properties including luminous efficiency were measured.
Ag/ITO / 정공주입층 (HAT-CN, 5 nm) / 정공수송층 (α-NPB, 100 nm) / 전자저지층 (TCTA, 10 nm) / 발광층 (BH1:BD1 20 nm) / 전자수송층 (201:Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / 광효율 개선층 1 (70 nm) / 광효율 개선층 2 (30 nm)Ag/ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (TCTA, 10 nm) / emitting layer (BH1:BD1 20 nm) / electron transport layer (201 :Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / Light efficiency improvement layer 1 (70 nm) / Light efficiency improvement layer 2 (30 nm)
유리 기판상에 Ag를 포함하는 ITO 투명 전극에 정공주입층을 형성하기 위해 [HAT-CN]을 5 nm 두께로 성막하고, 이후 정공수송층을 [α-NPB]를 사용하여 100 nm의 두께로 성막하였다. 전자저지층은 TCTA를 10 nm 두께로 성막하였다. 또한, 발광층에는 호스트 화합물로는 [BH1]을 사용하고, 도펀트 화합물로 [BD1]을 사용하여 20 nm로 성막하였다. 추가로 전자 수송층(하기 [201] 화합물 Liq 50% 도핑) 30 nm 및 LiF 1 nm로 성막하였다. 이어서 Mg:Ag (1:9) 15 nm의 두께로 성막하였다.[HAT-CN] was deposited to a thickness of 5 nm to form a hole injection layer on the ITO transparent electrode containing Ag on a glass substrate, and then the hole transport layer was deposited to a thickness of 100 nm using [α-NPB]. I did. As for the electron blocking layer, TCTA was deposited to a thickness of 10 nm. Further, for the light emitting layer, a film was formed at 20 nm using [BH1] as a host compound and [BD1] as a dopant compound. In addition, an electron transport layer (following [201] compound Liq doped 50%) was formed with 30 nm and 1 nm of LiF. Subsequently, a film was formed to a thickness of 15 nm Mg:Ag (1:9).
그리고, 광효율 개선층 1의 화합물로는 Alq3 를 70 nm 성막하고, 광효율 개선층 2로는 본 발명으로 구현되는 [화합물 21, 28, 41, 55, 67, 91, 101, 107, 110]을 30 nm의 두께로 성막하여 청색 유기발광소자를 제작하였다.In addition, as the compound of the light efficiency improvement layer 1, Alq3 was deposited at 70 nm, and the [Compounds 21, 28, 41, 55, 67, 91, 101, 107, 110] implemented by the present invention were deposited at 30 nm as the light efficiency improvement layer 2. The film was formed to a thickness of to fabricate a blue organic light emitting device.
소자 비교예 3Element Comparative Example 3
소자 비교예 3을 위한 유기발광소자는 상기 실시예 14 내지 22의 소자구조에서 본 발명에 따른 화합물을 포함하는 광효율 개선층 2 를 사용하지 않는 점을 제외하고 동일하게 제작하였다.The organic light-emitting device for Device Comparative Example 3 was fabricated in the same manner, except that the light efficiency improving layer 2 including the compound according to the present invention was not used in the device structures of Examples 14 to 22.
실험예 3: 소자 실시예 14 내지 22의 발광 특성Experimental Example 3: Light emission characteristics of device Examples 14 to 22
상기 실시예에 따라 제조된 유기발광소자는 Source meter (Model 237, Keithley)와 휘도계 (PR-650, Photo Research)를 이용하여 구동 전압, 전류 효율 및 색좌표를 측정하였고, 1,000 nit 기준의 결과값은 하기 [표 3]와 같다.The organic light-emitting device manufactured according to the above example measured driving voltage, current efficiency, and color coordinates using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the result value based on 1,000 nit. Is as shown in [Table 3] below.
상기 [표 3]에 나타낸 결과를 살펴보면, 본 발명에 따른 화합물을 광효율 개선층으로 소자에 적용한 경우에 종래 소자(비교예 3)에 비하여 구동 전압이 감소하고, 전류 효율이 향상되는 것을 확인할 수 있다.Looking at the results shown in [Table 3], it can be seen that when the compound according to the present invention is applied to a device as a light efficiency improvement layer, compared to the conventional device (Comparative Example 3), the driving voltage is reduced and the current efficiency is improved. .
[HAT-CN] [α-NPB] [BH1] [BD1] [201][HAT-CN] [α-NPB] [BH1] [BD1] [201]
[TCTA][TCTA]
Claims (11)
[화학식 Ⅰ]
상기 [화학식 Ⅰ]에서,
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소 및 치환 또는 비치환된 탄소수 1 내지 20의 알킬기 중에서 선택되며,
Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 하기 [구조식 1]로 표시되는 것을 특징으로 하고,
[구조식 1]
상기 [구조식 1]에서,
X1 내지 X8은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR이고, 상기 R은 수소, 중수소, 치환 또는 비치환된 탄소수 1 내지 20의 알킬기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 헤테로아릴기 중에서 선택되며,
상기 X1 내지 X8 중 어느 하나는 C-*이고, '*'는 상기 Ar1 내지 Ar4 각각과 연결되는 것을 의미한다.Organic light-emitting compound represented by the following [Chemical Formula I]:
[Chemical Formula Ⅰ]
In the above [Chemical Formula I],
R 1 and R 2 are the same as or different from each other, and each independently selected from deuterium and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
Ar 1 to Ar 4 are the same as or different from each other, and each independently is characterized in that it is represented by the following [Structural Formula 1],
[Structural Formula 1]
In the [Structural Formula 1],
X 1 to X 8 are the same as or different from each other, each independently N or CR, wherein R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms Is selected from a group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
Any one of X 1 to X 8 is C-*, and'*' means that each of Ar 1 to Ar 4 is connected.
상기 Ar1 내지 Ar4는 서로 결합하거나 인접한 치환기와 연결되어 적어도 하나 이상의 지환족, 방향족의 단일환 또는 다환 고리를 형성할 수 있고, 상기 형성된 지환족, 방향족의 단일환 또는 다환 고리의 탄소원자는 질소 원자(N), 황 원자(S) 및 산소 원자(O) 중에서 선택되는 어느 하나 이상의 헤테로원자로 치환될 수 있는 것을 특징으로 하는 유기발광 화합물.The method of claim 1,
The Ar 1 to Ar 4 may be bonded to each other or connected with an adjacent substituent to form at least one alicyclic, aromatic monocyclic or polycyclic ring, and the carbon atom of the formed alicyclic, aromatic monocyclic or polycyclic ring is nitrogen An organic light-emitting compound, characterized in that it can be substituted with one or more heteroatoms selected from an atom (N), a sulfur atom (S) and an oxygen atom (O).
상기 치환 또는 비치환이란 중수소, 할로겐기, 시아노기, 니트로기, 히드록시기, 실릴기, 탄소수 1 내지 20의 알킬기, 탄소수 1 내지 20의 할로겐화된 알킬기, 탄소수 3 내지 20의 시클로알킬기, 탄소수 1 내기 20의 알콕시기, 탄소수 1 내지 20의 할로겐화된 알콕시기, 탄소수 2 내지 20의 알케닐기, 탄소수 6 내지 30의 아릴기, 탄소수 3 내지 30의 헤테로아릴기 및 플루오레닐기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되거나, 상기 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것인 것을 특징으로 하는 유기발광 화합물.The method of claim 1,
The substituted or unsubstituted means deuterium, halogen group, cyano group, nitro group, hydroxy group, silyl group, alkyl group having 1 to 20 carbon atoms, halogenated alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, 1 to 20 carbon atoms 1 or 2 selected from the group consisting of an alkoxy group, a halogenated alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 carbon atoms, and a fluorenyl group An organic light-emitting compound, characterized in that it is substituted with the above substituents, substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.
상기 [화학식 Ⅰ]은 하기 [화합물 1] 내지 [화합물 133] 중에서 선택되는 어느 하나인 것을 특징으로 하는 유기발광 화합물:
[Chemical Formula I] is an organic light-emitting compound, characterized in that any one selected from the following [Compound 1] to [Compound 133]:
상기 유기물층 중 1 층 이상은 제1항에 따른 [화학식 Ⅰ]로 구현되는 유기발광 화합물을 하나 이상 포함하는 것을 특징으로 하는 유기발광소자.An organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
At least one of the organic material layers includes at least one organic light emitting compound represented by [Chemical Formula I] according to claim 1.
상기 유기물층은 정공 주입층, 정공 수송층, 정공 주입과 정공 수송 기능을 동시에 하는 층, 전자 수송층, 전자 주입층, 전자 수송과 전자 주입 기능을 동시에 하는 층, 전자 저지층, 정공 저지층 및 발광층 중에서 선택되는 1층 이상을 포함하고,
상기 층들 중 1층 이상이 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.The method of claim 5,
The organic material layer is selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer, and a light emitting layer. Including the first floor or more,
An organic light-emitting device, wherein at least one of the layers includes an organic light-emitting compound represented by [Chemical Formula I].
상기 발광층은 1종 이상의 호스트 화합물을 포함하고, 상기 호스트 화합물 중 하나는 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물인 것을 특징으로 하는 유기발광소자.The method of claim 6,
The light-emitting layer includes one or more host compounds, and one of the host compounds is an organic light-emitting compound represented by [Chemical Formula I].
상기 전자수송층이 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.The method of claim 6,
An organic light-emitting device, characterized in that the electron transport layer comprises an organic light-emitting compound represented by [Chemical Formula I].
상기 전자수송층은 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물 외에, 1종 이상의 전자수송 화합물을 더 혼합하여 포함하거나, 상기 전자수송층이 복수의 전자수송층으로 이루어지고, 상기 어느 하나의 전자수송층이 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.The method of claim 6,
In addition to the organic light-emitting compound represented by the above [Chemical Formula I], the electron transport layer may further include one or more electron transport compounds, or the electron transport layer is composed of a plurality of electron transport layers, and any one of the electron transport layers comprises the An organic light-emitting device comprising an organic light-emitting compound represented by [Chemical Formula I].
상기 제1 전극과 제2 전극의 상부 또는 하부 중에서 상기 유기물층과 반대되는 적어도 일측에 형성되는 광효율 개선층 (Capping layer)을 더 포함하고,
상기 광효율 개선층은 상기 [화학식 Ⅰ]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기발광소자.The method of claim 5,
Further comprising a capping layer formed on at least one side opposite to the organic material layer among the upper or lower portions of the first electrode and the second electrode,
The organic light-emitting device, characterized in that the light-efficiency improvement layer includes an organic light-emitting compound represented by [Chemical Formula I].
상기 광효율 개선층은 상기 제1 전극의 하부 또는 상기 제2 전극의 상부 중 적어도 하나에 형성되는 것을 특징으로 하는 유기발광소자.The method of claim 10,
The organic light-emitting device, wherein the light efficiency improvement layer is formed on at least one of a lower portion of the first electrode or an upper portion of the second electrode.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020190131576A KR20210048018A (en) | 2019-10-22 | 2019-10-22 | An electroluminescent compound and an electroluminescent device comprising the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020190131576A KR20210048018A (en) | 2019-10-22 | 2019-10-22 | An electroluminescent compound and an electroluminescent device comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20210048018A true KR20210048018A (en) | 2021-05-03 |
Family
ID=75910966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020190131576A KR20210048018A (en) | 2019-10-22 | 2019-10-22 | An electroluminescent compound and an electroluminescent device comprising the same |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR20210048018A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023017900A1 (en) * | 2021-08-13 | 2023-02-16 | (주)피엔에이치테크 | Organic compound and organic light-emitting device comprising same |
| WO2023043164A1 (en) * | 2021-09-15 | 2023-03-23 | (주)피엔에이치테크 | Organic compound and organic light-emitting device comprising same |
-
2019
- 2019-10-22 KR KR1020190131576A patent/KR20210048018A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023017900A1 (en) * | 2021-08-13 | 2023-02-16 | (주)피엔에이치테크 | Organic compound and organic light-emitting device comprising same |
| WO2023043164A1 (en) * | 2021-09-15 | 2023-03-23 | (주)피엔에이치테크 | Organic compound and organic light-emitting device comprising same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR102046983B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR102080737B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR102210267B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20200100972A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20190140233A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR102192691B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210089294A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR102170558B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210090389A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR102251836B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210048018A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210112608A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210072660A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210123922A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210008218A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR102665301B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210113775A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210146628A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20220084564A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20220004334A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20220005264A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20220086804A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20210105042A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20220003680A (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR20200091986A (en) | An electroluminescent compound and an electroluminescent device comprising the same |