KR102197612B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents
Organic compound and organic electroluminescent device comprising the same Download PDFInfo
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- KR102197612B1 KR102197612B1 KR1020140186422A KR20140186422A KR102197612B1 KR 102197612 B1 KR102197612 B1 KR 102197612B1 KR 1020140186422 A KR1020140186422 A KR 1020140186422A KR 20140186422 A KR20140186422 A KR 20140186422A KR 102197612 B1 KR102197612 B1 KR 102197612B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- inv
- formula
- carbazole
- synthesis
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title abstract description 7
- 239000011368 organic material Substances 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 87
- 238000000034 method Methods 0.000 claims description 39
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 111
- 238000003786 synthesis reaction Methods 0.000 description 110
- 239000010410 layer Substances 0.000 description 59
- 238000002360 preparation method Methods 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- -1 Metal complex compounds Chemical class 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- YCYSJVWZQQIVOY-UHFFFAOYSA-N 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound C1(=CC=CC=C1)C1=CC(=CC=2C3=CC=CC(=C3N(C1=2)C1=CC=CC=C1)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 YCYSJVWZQQIVOY-UHFFFAOYSA-N 0.000 description 8
- HVBKICOWNNJTRK-UHFFFAOYSA-N 8-chloro-1,3-diphenyl-9H-carbazole Chemical compound ClC=1C=CC=C2C=3C=C(C=C(C=3NC=12)C1=CC=CC=C1)C1=CC=CC=C1 HVBKICOWNNJTRK-UHFFFAOYSA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 4
- VEUNBDBSLKXMER-UHFFFAOYSA-N 8-chloro-1,3-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole Chemical compound ClC=1C=CC=C2C3CC(CC(C3NC=12)C1=CC=CC=C1)C1=CC=CC=C1 VEUNBDBSLKXMER-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- MRBZYVMZUBUDAX-UHFFFAOYSA-N (3,5-diphenylphenyl)boronic acid Chemical compound C=1C(B(O)O)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 MRBZYVMZUBUDAX-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 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
- MMTJRYAVTQORAA-UHFFFAOYSA-N 6-chloro-1,3-diphenyl-9H-carbazole Chemical compound ClC=1C=C2C=3C=C(C=C(C3NC2=CC1)C1=CC=CC=C1)C1=CC=CC=C1 MMTJRYAVTQORAA-UHFFFAOYSA-N 0.000 description 3
- OCQFNQDUZYHBEQ-UHFFFAOYSA-N 6-chloro-1,4-diphenyl-9H-carbazole Chemical compound ClC=1C=C2C=3C(=CC=C(C=3NC2=CC=1)C1=CC=CC=C1)C1=CC=CC=C1 OCQFNQDUZYHBEQ-UHFFFAOYSA-N 0.000 description 3
- YMZZJTAOWLQKPS-UHFFFAOYSA-N 7-chloro-1,3-diphenyl-9H-carbazole Chemical compound ClC1=CC=C2C=3C=C(C=C(C=3NC2=C1)C1=CC=CC=C1)C1=CC=CC=C1 YMZZJTAOWLQKPS-UHFFFAOYSA-N 0.000 description 3
- VDFOVKDVLKKVIX-UHFFFAOYSA-N 7-chloro-1,4-diphenyl-9H-carbazole Chemical compound ClC1=CC=C2C=3C(=CC=C(C=3NC2=C1)C1=CC=CC=C1)C1=CC=CC=C1 VDFOVKDVLKKVIX-UHFFFAOYSA-N 0.000 description 3
- NMFXHRZDSINBRO-UHFFFAOYSA-N 8-chloro-1,4-diphenyl-9H-carbazole Chemical compound ClC=1C=CC=C2C=3C(=CC=C(C=3NC=12)C1=CC=CC=C1)C1=CC=CC=C1 NMFXHRZDSINBRO-UHFFFAOYSA-N 0.000 description 3
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 3
- 0 Nc1ccc2-c3cc(-c4ccccc4)cc(-c4ccccc4)c3*c2c1 Chemical compound Nc1ccc2-c3cc(-c4ccccc4)cc(-c4ccccc4)c3*c2c1 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- DSRUKWZKBKKLOD-UHFFFAOYSA-N (2,5-diphenylphenyl)boronic acid Chemical compound OB(O)C1=CC(C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 DSRUKWZKBKKLOD-UHFFFAOYSA-N 0.000 description 2
- YCINRIIWEDLSHQ-UHFFFAOYSA-N 1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound C1(=CC=CC=C1)C1=CC=C(C=2C3=CC(=CC=C3N(C1=2)C1=CC=CC=C1)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 YCINRIIWEDLSHQ-UHFFFAOYSA-N 0.000 description 2
- DARXPSFNGQLCGP-UHFFFAOYSA-N 2,4-diphenylcyclohexan-1-one Chemical compound O=C1CCC(C=2C=CC=CC=2)CC1C1=CC=CC=C1 DARXPSFNGQLCGP-UHFFFAOYSA-N 0.000 description 2
- RZUQKDSKSNBEKS-UHFFFAOYSA-N 2,5-diphenylcyclohexan-1-one Chemical compound O=C1CC(C=2C=CC=CC=2)CCC1C1=CC=CC=C1 RZUQKDSKSNBEKS-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ZLQFWQOAQQBLLZ-UHFFFAOYSA-N 4-chloro-1-iodo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1I ZLQFWQOAQQBLLZ-UHFFFAOYSA-N 0.000 description 2
- OTLJSDATRAVVAV-UHFFFAOYSA-N 4-chloro-2-iodo-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1I OTLJSDATRAVVAV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- 229910045601 alloy Inorganic materials 0.000 description 2
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
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- AMHJZXDNOQNDJE-UHFFFAOYSA-N 1,2,3-triphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole Chemical compound C1(=CC=CC=C1)C=1C(=C(C=2NC3=CC(=CC=C3C=2C=1)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1)C1=CC=CC=C1 AMHJZXDNOQNDJE-UHFFFAOYSA-N 0.000 description 1
- BXKCUUZVDSMDDB-UHFFFAOYSA-N 1,2,3-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole Chemical compound C1(=CC=CC=C1)C=1C(=C(C=2NC3=C(C=CC=C3C=2C=1)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1)C1=CC=CC=C1 BXKCUUZVDSMDDB-UHFFFAOYSA-N 0.000 description 1
- KRVWTVYQGIOXQE-UHFFFAOYSA-N 1-(2,6-diphenoxyphenoxy)naphthalene Chemical group C=1C=CC(OC=2C=CC=CC=2)=C(OC=2C3=CC=CC=C3C=CC=2)C=1OC1=CC=CC=C1 KRVWTVYQGIOXQE-UHFFFAOYSA-N 0.000 description 1
- HYKFPJAARRNNRX-UHFFFAOYSA-N 2,3,4,4a,9,9a-hexahydro-1h-carbazole Chemical compound C1=CC=C2C3CCCCC3NC2=C1 HYKFPJAARRNNRX-UHFFFAOYSA-N 0.000 description 1
- ADODRSVGNHNKAT-UHFFFAOYSA-N 2-Chlorophenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1Cl ADODRSVGNHNKAT-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- JBEQRROTSDUCGC-UHFFFAOYSA-N 3-bromo-6,9-diphenylcarbazole Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 JBEQRROTSDUCGC-UHFFFAOYSA-N 0.000 description 1
- CYUADOXCIQUSCG-UHFFFAOYSA-N 8-chloro-1,4-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole Chemical compound ClC=1C=CC=C2C3C(CCC(C3NC=12)C1=CC=CC=C1)C1=CC=CC=C1 CYUADOXCIQUSCG-UHFFFAOYSA-N 0.000 description 1
- YMDUGVJLJVEVST-UHFFFAOYSA-N 9-(3,5-diphenylphenyl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound C1(=CC=CC=C1)C1=CC(=CC(=C1)N1C2=CC=C(C=C2C=2C(=CC=C(C1=2)C1=CC=CC=C1)C1=CC=CC=C1)B1OC(C(O1)(C)C)(C)C)C1=CC=CC=C1 YMDUGVJLJVEVST-UHFFFAOYSA-N 0.000 description 1
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
본 발명은 유기 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic compound and an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including it in one or more organic material layers.
Description
본 발명은 신규한 유기 화합물 및 이를 포함한 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device including the same.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 상기 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.In an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. Materials used as the organic material layer may be classified into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like, according to their functions.
현재까지 정공 주입 물질, 정공 수송 물질. 정공 차단 물질, 전자 수송 물질로는 NPB, BCP, Alq3 등이 알려져 있고, 발광 물질로는 안트라센 유도체와, Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물 등이 알려져 있다.To date, hole injection materials, hole transport materials. As a hole blocking material and an electron transport material, NPB, BCP, Alq 3, etc. are known, and as a light emitting material, an anthracene derivative and Ir, such as Firpic, Ir(ppy) 3 , (acac)Ir(btp) 2, etc. Metal complex compounds and the like are known.
그러나 이러한 물질들은 유리전이온도가 낮고 열적 안정성이 좋지 않아 유기 전계 발광 소자의 수명 측면에서 만족할만한 수준이 되지 못하고 있다.However, these materials have a low glass transition temperature and poor thermal stability, so they are not at a satisfactory level in terms of the lifespan of an organic electroluminescent device.
본 발명은 유기 전계 발광 소자의 발광능을 높일 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다.An object of the present invention is to provide a novel organic compound capable of enhancing the luminous ability of an organic electroluminescent device.
또한 본 발명은 상기 신규 유기 화합물을 포함하는 유기 전계 발광 소자를 제공하는 것도 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound.
상기 목적을 달성하기 위하여 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
L은 단일결합, C6~C40의 아릴렌기, 또는 핵원자수 5 내지 40의 헤테로아릴렌기이고,L is a single bond, a C 6 ~ C 40 arylene group, or a heteroarylene group having 5 to 40 nuclear atoms,
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,R 1 and R 2 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, C of 6 ~ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C of 3 ~ C 40 cycloalkyl group, a nuclear atom A number of 3 to 40 heterocycloalkyl groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkyl boron groups, C 6 to C 40 aryl boron groups, C 6 to C 40 arylphosphine groups, C 6 ~ C 40 is selected from the group consisting of aryl phosphine oxide group and C 6 ~ C 40 arylsilyl group,
상기 L의 C6~C40의 아릴렌기, 핵원자수 5 내지 40의 헤테로아릴렌기와, 상기 R1 및 R2의 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기는, 각각 독립적으로 중수소, 할로겐기, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되는 하나 이상의 치환기로 치환 또는 비치환된다. 이때 치환기가 복수일 경우, 복수의 치환기는 서로 동일하거나 상이하다.The C 6 ~ C 40 arylene group of the L, a heteroarylene group having 5 to 40 nuclear atoms, the C 1 ~ C 40 alkyl group of the R 1 and R 2 , C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, 5 ~ 40 nuclear atoms heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 40 aryl boron group, C 6 to C 40 arylphosphine group, C 6 to C 40 arylphosphine oxide group and C 6 to C 40 arylsilyl group are each independently deuterium, halogen group, cyano group, C 1 to C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, nuclear atom number 5 ~ 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 to C 40 arylamine group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 1 to C 40 alkylsilyl group, C 1 to C 40 groups of an alkyl boron, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ from the group consisting arylsilyl of C 40 of It is unsubstituted or substituted with one or more selected substituents. In this case, when there is a plurality of substituents, the plurality of substituents are the same or different from each other.
또한, 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나가 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.In addition, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers comprises a compound represented by Formula 1 It provides an organic electroluminescent device including.
본 발명에서 알킬은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyl refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
본 발명에서 알케닐(alkenyl)은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkenyl means a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.
본 발명에서 알키닐(alkynyl)은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkynyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.
본 발명에서 아릴은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 40의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 40 carbon atoms in which a single ring or two or more rings are combined. In addition, a form in which two or more rings are simply attached to each other or condensed may be included. Examples thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.
본 발명에서 헤테로아릴은 핵원자수 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with heteroatoms such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples thereof include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycyclics such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 아릴옥시는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 40의 아릴을 의미한다. 이의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryloxy is a monovalent substituent represented by RO-, and R means an aryl having 6 to 40 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서 알킬옥시는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyloxy is a monovalent substituent represented by R'O-, and R'means alkyl having 1 to 40 carbon atoms, and includes a linear, branched, or cyclic structure. can do. Examples of the alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
본 발명에서 아릴아민은 탄소수 6 내지 40의 아릴로 치환된 아민을 의미한다.In the present invention, an arylamine means an amine substituted with an aryl having 6 to 40 carbon atoms.
본 발명에서 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, cycloalkyl refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서 헤테로시클로알킬은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, heterocycloalkyl refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or Se Is substituted with a hetero atom such as. Examples thereof include morpholine and piperazine, but are not limited thereto.
본 발명에서 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 40의 아릴로 치환된 실릴을 의미한다.In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms.
본 발명에서 축합고리는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, a condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. 특히, 본 발명의 화학식 1로 표시되는 화합물을 발광층의 인광 호스트로 사용할 경우 발광 성능, 구동전압 및 수명 특성이 우수한 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.Since the compound represented by Formula 1 of the present invention has excellent thermal stability and light emission properties, it can be used as a material for an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host of the light emitting layer, an organic electroluminescent device having excellent light emitting performance, driving voltage, and lifetime characteristics can be manufactured, and furthermore, a full color display panel with improved performance and lifespan Can be manufactured.
이하, 본 발명을 설명한다.
Hereinafter, the present invention will be described.
1. 유기 화합물1. Organic compounds
본 발명의 유기 화합물은 1 번 위치에 페닐기가 결합된 2개의 카바졸 모이어티(carbazole moiety)가 서로 결합되어 기본 골격을 이루는 화합물로, 상기 화학식 1로 표시된다.The organic compound of the present invention is a compound in which two carbazole moieties having a phenyl group bonded to each other are bonded to each other to form a basic skeleton, and is represented by Formula 1 above.
본 발명의 화학식 1로 표시되는 화합물은 카바졸 모이어티의 1번 위치에 페닐기가 결합(치환)되어 분자가 뒤틀리는 파이파이-스태킹(π-π-stacking) 구조를 가진다. 이러한 파이파이-스태킹(π-π-stacking) 구조를 가지는 본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 유기물층에 적용할 경우 여기 이합체(엑사이머, excimer) 형성이 방지되어 유기 전계 발광 소자의 발광 효율을 향상시킬 수 있다.The compound represented by Formula 1 of the present invention has a pi-pi-stacking structure in which a phenyl group is bonded (substituted) to the 1 position of the carbazole moiety and the molecule is distorted. When the compound represented by Formula 1 of the present invention having such a pi-pi-stacking structure is applied to the organic material layer of an organic electroluminescent device, the formation of excimers (excimers) is prevented and the organic electric field It is possible to improve the luminous efficiency of the light emitting device.
또한 카바졸 모이어티의 1번 위치에 페닐기가 결합된 본 발명의 화학식 1로 표시되는 화합물은 1번 위치에 페닐기가 결합되지 않은 카바졸 모이어티를 포함하는 화합물보다 분자의 열안정성이 높기 때문에 이를 유기 전계 발광 소자의 유기물층에 적용할 경우 유기 전계 발광 소자의 성능 및 수명 특성을 향상시킬 수 있다.In addition, the compound represented by Formula 1 of the present invention in which a phenyl group is bonded to the 1st position of the carbazole moiety is higher than that of the compound containing the carbazole moiety to which the phenyl group is not bonded to the 1st position. When applied to an organic material layer of an organic electroluminescent device, the performance and life characteristics of the organic electroluminescent device can be improved.
한편 본 발명의 화학식 1로 표시되는 화합물은 높은 삼중항 에너지를 갖기 때문에 이를 유기 전계 발광 소자의 발광 보조층(구체적으로, 정공 수송층과 발광층 사이에 구비되는 층), 또는 수명 개선층(구체적으로, 발광층과 전자 수송층 사이에 구비되는 층)에 적용할 경우 발광층에서 생성된 엑시톤이 인접하는 전자수송층, 또는 정공수송층으로 확산되는 것을 방지할 수 있다.Meanwhile, since the compound represented by Formula 1 of the present invention has a high triplet energy, it is a light emitting auxiliary layer (specifically, a layer provided between the hole transport layer and the light emitting layer) of the organic electroluminescent device, or a lifespan improvement layer (specifically, When applied to a layer provided between the light emitting layer and the electron transport layer), it is possible to prevent the excitons generated in the light emitting layer from being diffused into the adjacent electron transport layer or hole transport layer.
따라서 본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광 보조층, 또는 수명 개선층에 적용할 경우 내구성, 안정성 및 수명이 우수한 유기 전계 발광 소자를 제공할 수 있다.Accordingly, when the compound represented by Formula 1 of the present invention is applied to a light emitting auxiliary layer or a life improving layer of an organic electroluminescent device, an organic electroluminescent device having excellent durability, stability, and life can be provided.
이러한 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 7로 표시되는 화합물 중 어느 하나로 구체화될 수 있다.The compound represented by Formula 1 of the present invention may be embodied in any one of the compounds represented by the following Formulas 2 to 7.
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[화학식 7][Formula 7]
상기 화학식 2 내지 7에서,In Formulas 2 to 7,
L, R1 및 R2는 상기 화학식 1에서 정의한 바와 같다.L, R 1 and R 2 are as defined in Chemical Formula 1.
특히, 유기 전계 발광 소자의 특성을 고려할 때, 본 발명의 화학식 1로 표시되는 화합물에서 L은 단일결합 또는 페닐렌인 것이 바람직하다.In particular, when considering the characteristics of the organic electroluminescent device, it is preferable that L is a single bond or phenylene in the compound represented by Chemical Formula 1 of the present invention.
또한 본 발명의 화학식 1로 표시되는 화합물에서 R1 및 R2는 모두 C6~C40의 아릴기인 것이 바람직하다.In addition, in the compound represented by Formula 1 of the present invention, it is preferable that both R 1 and R 2 are C 6 ~ C 40 aryl groups.
구체적으로, 본 발명의 화학식 1로 표시되는 화합물에서 R1 및 R2는 각각 독립적으로, 하기 S1 내지 S6으로 표시되는 구조(치환기)로 이루어진 군에서 선택되는 것이 더욱 바람직하다.Specifically, in the compound represented by Formula 1 of the present invention, R 1 and R 2 are each independently more preferably selected from the group consisting of structures (substituents) represented by the following S1 to S6.
이러한 본 발명의 화학식 1로 표시되는 화합물의 구체적인 예는 하기 화합물들을 들 수 있으나, 이에 한정되는 것은 아니다.Specific examples of the compound represented by Chemical Formula 1 of the present invention include the following compounds, but are not limited thereto.
2. 유기 전계 발광 소자2. Organic EL device
본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device including the compound represented by Chemical Formula 1.
구체적으로, 본 발명의른 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.Specifically, another organic electroluminescent device of the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by Formula 1. In this case, the compound may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 수명 개선층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 구체적으로 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층, 발광 보조층, 수명 개선층인 것이 바람직하다.The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, a life improvement layer, an electron transport layer, and an electron injection layer, of which at least one organic material layer is a compound represented by Formula 1 It may include. Specifically, it is preferable that the organic material layer including the compound represented by Formula 1 is a light emitting layer, a light emitting auxiliary layer, and a life improving layer.
한편, 상기 발광층은 호스트를 포함할 수 있는데, 이때 호스트로서 상기 화학식 1로 표시되는 화합물을 단독으로 포함하거나 상기 화학식 1로 표시되는 화합물과 함께 다른 화합물도 호스트로 포함할 수 있다.Meanwhile, the emission layer may include a host, and in this case, a compound represented by Formula 1 may be included as a host, or other compounds may be included as a host in addition to the compound represented by Formula 1 above.
본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 수명 개선층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 전자 수송층 위에는 전자 주입층이 추가로 적층될 수 있다. 또한 상기 전극(음극, 또는 양극)과 유기물층 계면에 절연층 또는 접착층이 더 적층될 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may have a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emission auxiliary layer, an emission layer, a life improvement layer, an electron transport layer, and a cathode are sequentially stacked. In this case, an electron injection layer may be additionally stacked on the electron transport layer. In addition, an insulating layer or an adhesive layer may be further laminated at the interface between the electrode (cathode or anode) and the organic material layer.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 제조할 수 있다.The organic electroluminescent device of the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers contains the compound represented by Chemical Formula 1.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
본 발명의 유기 전계 발광 소자 제조 시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 등을 사용할 수 있다.The substrate used in the manufacture of the organic electroluminescent device of the present invention is not particularly limited, but a silicon wafer, quartz, glass plate, metal plate, plastic film, or the like may be used.
또, 양극 물질은 특별히 한정되지 않으나, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 사용할 수 있다.In addition, the anode material is not particularly limited, but metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO2:Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black.
또, 음극 물질은 특별히 한정되지 않으나, 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등을 사용할 수 있다.In addition, the negative electrode material is not particularly limited, but a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof; And a multi-layered material such as LiF/Al or LiO2/Al.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.
In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.
Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited by the following examples.
[준비예 1] Core1의 합성[Preparation Example 1] Synthesis of Core1
<단계 1> 8-chloro-1,3-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole의 합성<Step 1> Synthesis of 8-chloro-1,3-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole
질소 기류 하에서 2,4-diphenylcyclohexan-1-one 50g (199.72 mmol), (2-chlorophenyl)hydrazine hydrochloride 35.7g (199.72 mmol) 및 Acetic acid 500ml를 넣고 120℃에서 12시간 동안 환류 교반하였다. 반응 종결 후 Acetic acid를 제거한 뒤, Sodium bicarbonate와 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼 크로마토그래피를 이용하여 목적 화합물인 8-chloro-1,3-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole (48 g, 수율: 66%)을 얻었다.In a nitrogen stream, 2,4-diphenylcyclohexan-1-one 50g (199.72 mmol), (2-chlorophenyl)hydrazine hydrochloride 35.7g (199.72 mmol) and Acetic acid 500ml were added and stirred under reflux for 12 hours at 120°C. After completion of the reaction, acetic acid was removed, extracted with sodium bicarbonate and dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. After distilling the filtered organic layer under reduced pressure, the target compound, 8-chloro-1,3-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole (48 g, yield: 66%).
1H-NMR: δ 2.20 (m, 2H), 2.83 (m, 2H), 3.12 (m, 1H), 4.05(m, 1H), 7.14 (m, 2H), 7.35(m, 10H), 7.55 (d, 1H), 12.12(s, 1H) 1 H-NMR: δ 2.20 (m, 2H), 2.83 (m, 2H), 3.12 (m, 1H), 4.05 (m, 1H), 7.14 (m, 2H), 7.35 (m, 10H), 7.55 ( d, 1H), 12.12(s, 1H)
<단계 2> 8-chloro-1,3-diphenyl-9H-carbazole의 합성<Step 2> Synthesis of 8-chloro-1,3-diphenyl-9H-carbazole
질소 기류 하에서 8-chloro-1,3-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 48 g (133.37 mmol) 및 Benzene 300ml를 넣은 후 30분 동안 5회에 걸쳐 DDQ 60.5 g (266.74 mmol)을 나누어 넣고 1시간 동안 교반하였다. 반응 종료 후 Silicagel 및 Celite에 필터한 뒤 Benzene을 제거하고 디클로로메탄으로 추출하였다. 추출된 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 한 뒤 컬럼크로마토그래피를 이용하여 목적 화합물인 8-chloro-1,3-diphenyl-9H-carbazole (35 g, 수율:74%)을 얻었다.Add 48 g (133.37 mmol) of 8-chloro-1,3-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole and 300 ml of Benzene under a nitrogen stream, and then DDQ 5 times for 30 minutes. 60.5 g (266.74 mmol) was added in portions and stirred for 1 hour. After the reaction was completed, the mixture was filtered through Silicagel and Celite, and Benzene was removed, followed by extraction with dichloromethane. The extracted organic layer was dried over MgSO 4 and filtered under reduced pressure. After distilling the filtered organic layer under reduced pressure, the target compound, 8-chloro-1,3-diphenyl-9H-carbazole (35 g, yield: 74%) was obtained by column chromatography.
1H-NMR: δ 7.18 (m, 6H), 7.52 (m, 4H), 7.78 (m, 3H), 8.05 (s, 1H), 8.12 (d, 1H), 12.25(s, 1H) 1 H-NMR: δ 7.18 (m, 6H), 7.52 (m, 4H), 7.78 (m, 3H), 8.05 (s, 1H), 8.12 (d, 1H), 12.25 (s, 1H)
<단계 3> Core1의 합성<Step 3> Synthesis of Core1
질소 기류 하에서 8-chloro-1,3-diphenyl-9H-carbazole 35 g (98.91 mmol), Iodobenzene 30.2 g (148.36 mmol), Cu powder 0.62 g (9.89 mmol), K2CO3 27.3 g (197.82 mmol) 및 nitrobenzene 300 ml를 혼합하고 190℃에서 12시간 동안 환류교반하였다. 반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 Core1 (35 g, 수율: 83%)을 얻었다.8-chloro-1,3-diphenyl-9H-carbazole 35 g (98.91 mmol), Iodobenzene 30.2 g (148.36 mmol), Cu powder 0.62 g (9.89 mmol), K 2 CO 3 27.3 g (197.82 mmol) under a nitrogen stream And 300 ml of nitrobenzene were mixed and stirred under reflux for 12 hours at 190°C. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent in the organic layer, it was purified by column chromatography to obtain the title compound Core1 (35 g, yield: 83%).
1H-NMR: δ 7.09 (d, 1H), 7.23 (m, 5H), 7.55 (m, 9H), 7.82 (m, 3H) 8.02(s, 1H), 8.15(d, 1H)
1 H-NMR: δ 7.09 (d, 1H), 7.23 (m, 5H), 7.55 (m, 9H), 7.82 (m, 3H) 8.02 (s, 1H), 8.15 (d, 1H)
[준비예 2] Core2의 합성[Preparation Example 2] Synthesis of Core2
<단계 1> 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl의 합성<Step 1> Synthesis of 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl
질소 기류 하에서 4-chloro-1-iodo-2-nitrobenzene 30g (105.84 mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid 34.8g (127 mmol), K2CO3 43.88g (317.52 mmol) 및 1,4-Dioxane/H2O 400ml/100 ml를 넣고 교반하였다. 40℃에서 Pd(PPh3)4 3.7 g (3.175 mmol)을 넣고 110℃에서 12시간 동안 환류 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조한 후 감압여과 하였다. 여과된 유기층을 감압증류한 뒤 컬럼크로마토그래피를 이용하여 목적 화합물인 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl (32 g, 수율: 78%)을 얻었다.4-chloro-1-iodo-2-nitrobenzene 30g (105.84 mmol), [1,1':3',1''-terphenyl]-5'-ylboronic acid 34.8g (127 mmol), K 2 under nitrogen stream CO 3 43.88g (317.52 mmol) and 1,4-Dioxane/H 2 O 400ml/100 ml were added and stirred. Pd(PPh 3 ) 4 3.7 g (3.175 mmol) was added at 40° C. and stirred at 110° C. for 12 hours under reflux. After completion of the reaction, extraction was performed with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. After distilling the filtered organic layer under reduced pressure, the target compound, 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl (32 g, yield: 78 %).
1H-NMR: δ 7.51 (m, 6H), 7.82 (m, 4H), 8.05 (m, 5H), 8.52 (s, 1H) 1 H-NMR: δ 7.51 (m, 6H), 7.82 (m, 4H), 8.05 (m, 5H), 8.52 (s, 1H)
<단계 2> 7-chloro-1,3-diphenyl-9H-carbazole의 합성<Step 2> Synthesis of 7-chloro-1,3-diphenyl-9H-carbazole
질소 기류 하에서 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 32 g (82.93 mmol), triphenylphosphine 43.5 g (165.86 mmol) 및 1,2-dichlorobenzene 300 ml를 넣은 후 180℃에서 12시간 동안 환류교반하였다. 반응 종료 후 디스틸레이션을 통해 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 추출하였다. 추출된 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼크로마토그래피를 이용하여 목적 화합물인 7-chloro-1,3-diphenyl-9H-carbazole (20 g, 수율:67%)을 얻었다.4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 32 g (82.93 mmol), triphenylphosphine 43.5 g (165.86 mmol) and 1,2-dichlorobenzene 300 under a nitrogen stream After adding ml, the mixture was stirred under reflux at 180° C. for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed through distillation and extracted with dichloromethane. The extracted organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure and then column chromatography to obtain the target compound, 7-chloro-1,3-diphenyl-9H-carbazole (20 g, yield: 67%).
1H-NMR: δ 6.98 (d, 1H), 7.18 (m, 4H), 7.45 (m, 5H), 7.78 (m, 3H), 8.05(m, 2H), 12.20(s, 1H) 1 H-NMR: δ 6.98 (d, 1H), 7.18 (m, 4H), 7.45 (m, 5H), 7.78 (m, 3H), 8.05 (m, 2H), 12.20 (s, 1H)
<단계 3> Core2의 합성<Step 3> Synthesis of Core2
8-chloro-1,3-diphenyl-9H-carbazole 대신 7-chloro-1,3-diphenyl-9H-carbazole 20 g (56.52 mmol)을 사용한 것을 제외하고는 준비예 1의 단계 3과 동일한 과정을 수행하여 목적 화합물인 Core2 (17 g, 수율: 77%)를 얻었다.The same procedure as in Step 3 of Preparation Example 1 was performed except that 20 g (56.52 mmol) of 7-chloro-1,3-diphenyl-9H-carbazole was used instead of 8-chloro-1,3-diphenyl-9H-carbazole. Thus, the target compound, Core2 (17 g, yield: 77%) was obtained.
1H-NMR: δ 7.02 (d, 1H), 7.18 (m, 4H), 7.58 (m, 10H), 7.78 (m, 3H) 8.02(s, 1H), 8.12(d, 1H)
1 H-NMR: δ 7.02 (d, 1H), 7.18 (m, 4H), 7.58 (m, 10H), 7.78 (m, 3H) 8.02 (s, 1H), 8.12 (d, 1H)
[준비예 3] Core3의 합성[Preparation Example 3] Synthesis of Core3
<단계 1> 5-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl의 합성<Step 1> Synthesis of 5-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl
4-chloro-1-iodo-2-nitrobenzene 대신 4-chloro-2-iodo-1-nitrobenzene 를 사용한 것을 제외하고는 준비예 2의 단계 1과 동일한 과정을 수행하여 목적 화합물인 5-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl (30 g, 수율: 75%)을 얻었다.Except that 4-chloro-2-iodo-1-nitrobenzene was used instead of 4-chloro-1-iodo-2-nitrobenzene, the target compound, 5-chloro-2- nitro-5'-phenyl-1,1':3',1''-terphenyl (30 g, yield: 75%) was obtained.
1H-NMR: δ 7.32 (m, 2H), 7.53 (m, 4H), 7.78 (m, 5H), 8.08(m, 3H), 8.25 (s, 1H), 8.44(d, 1H) 1 H-NMR: δ 7.32 (m, 2H), 7.53 (m, 4H), 7.78 (m, 5H), 8.08 (m, 3H), 8.25 (s, 1H), 8.44 (d, 1H)
<단계 2> 6-chloro-1,3-diphenyl-9H-carbazole의 합성<Step 2> Synthesis of 6-chloro-1,3-diphenyl-9H-carbazole
4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 대신 5-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 30 g (77.75 mmol)을 사용한 것을 제외하고는 준비예 2의 단계 2와 동일한 과정을 수행하여 목적 화합물인 6-chloro-1,3-diphenyl-9H-carbazole (18 g, 수율: 65%)을 얻었다.5-chloro-2-nitro-5'-phenyl-1,1':3',1' instead of 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl The target compound, 6-chloro-1,3-diphenyl-9H-carbazole (18 g, yield: 65) was carried out in the same manner as in Step 2 of Preparation Example 2, except that 30 g (77.75 mmol) of'-terphenyl was used. %).
1H-NMR: δ 7.15 (m, 5H), 7.58 (m, 6H), 7.75 (m, 3H), 8.03 (s, 1H), 12.25(s, 1H) 1 H-NMR: δ 7.15 (m, 5H), 7.58 (m, 6H), 7.75 (m, 3H), 8.03 (s, 1H), 12.25 (s, 1H)
<단계 3> Core3의 합성<Step 3> Synthesis of Core3
8-chloro-1,3-diphenyl-9H-carbazole 대신 6-chloro-1,3-diphenyl-9H-carbazole 18 g (50.87 mmol)을 사용한 것을 제외하고는 준비예 1의 단계 3과 동일한 과정을 수행하여 목적 화합물인 Core3 (17 g, 수율: 77%)을 얻었다.The same procedure as in Step 3 of Preparation Example 1 was performed except that 18 g (50.87 mmol) of 6-chloro-1,3-diphenyl-9H-carbazole was used instead of 8-chloro-1,3-diphenyl-9H-carbazole. Thus, the target compound, Core3 (17 g, yield: 77%) was obtained.
1H-NMR: δ 7.02 (d, 1H), 7.25 (m, 4H), 7.58 (m, 7H), 7.88 (m, 3H) 8.08(s, 1H)
1 H-NMR: δ 7.02 (d, 1H), 7.25 (m, 4H), 7.58 (m, 7H), 7.88 (m, 3H) 8.08 (s, 1H)
[준비예 4] Core4 의 합성[Preparation Example 4] Synthesis of Core4
<단계 1> 8-chloro-1,4-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole의 합성<Step 1> Synthesis of 8-chloro-1,4-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole
2,4-diphenylcyclohexan-1-one 대신 2,5-diphenylcyclohexan-1-one을 사용한 것을 제외하고는 준비예 1의 단계 1과 동일한 과정을 수행하여 목적 화합물인 8-chloro-1,4-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole (47 g, 수율: 65%)을 얻었다.Except that 2,5-diphenylcyclohexan-1-one was used instead of 2,4-diphenylcyclohexan-1-one, the target compound, 8-chloro-1,4-diphenyl-, was carried out in the same manner as in Step 1 of Preparation Example 1 2,3,4,4a,9,9a-hexahydro-1H-carbazole (47 g, yield: 65%) was obtained.
1H-NMR: δ 1.98 (m, 4H), 3.96 (t, 1H), 6.85 (m, 2H), 7.29 (m, 10H) 7.92(d, 1H), 12.22(s, 1H) 1 H-NMR: δ 1.98 (m, 4H), 3.96 (t, 1H), 6.85 (m, 2H), 7.29 (m, 10H) 7.92 (d, 1H), 12.22 (s, 1H)
<단계 2> 8-chloro-1,4-diphenyl-9H-carbazole의 합성<Step 2> Synthesis of 8-chloro-1,4-diphenyl-9H-carbazole
8-chloro-1,3-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 대신 8-chloro-1,4-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole 47 g (130.59 mmol)을 사용한 것을 제외하고는 준비예 1의 단계 2와 동일한 과정을 수행하여 목적 화합물인 8-chloro-1,4-diphenyl-9H-carbazole (33 g, 수율: 71%)을 얻었다.8-chloro-1,4-diphenyl-2,3,4,4a,9,9a- instead of 8-chloro-1,3-diphenyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole Except that hexahydro-1H-carbazole 47 g (130.59 mmol) was used, the same procedure as in Step 2 of Preparation Example 1 was performed, and the target compound, 8-chloro-1,4-diphenyl-9H-carbazole (33 g, yield : 71%) was obtained.
1H-NMR: δ 7.21 (m, 6H), 7.46 (m, 4H), 7.82 (m, 2H), 8.13 (m, 3H) 12.22(s, 1H) 1 H-NMR: δ 7.21 (m, 6H), 7.46 (m, 4H), 7.82 (m, 2H), 8.13 (m, 3H) 12.22 (s, 1H)
<단계 3> Core4의 합성<Step 3> Synthesis of Core4
8-chloro-1,3-diphenyl-9H-carbazole 대신 8-chloro-1,4-diphenyl-9H-carbazole 33 g (93.25 mmol)을 사용한 것을 제외하고는 준비예 1의 단계 3과 동일한 과정을 수행하여 목적 화합물인 Core4 (30 g, 수율: 75%)를 얻었다.The same procedure as in Step 3 of Preparation Example 1 was performed, except that 33 g (93.25 mmol) of 8-chloro-1,4-diphenyl-9H-carbazole was used instead of 8-chloro-1,3-diphenyl-9H-carbazole. Thus, the target compound, Core4 (30 g, yield: 75%) was obtained.
1H-NMR: δ 7.08 (d, 1H), 7.22 (m, 5H), 7.57 (m, 9H), 7.81 (m, 2H) 8.08(d, 1H), 8.43(d, 1H), 8.51(d, 1H)
1 H-NMR: δ 7.08 (d, 1H), 7.22 (m, 5H), 7.57 (m, 9H), 7.81 (m, 2H) 8.08 (d, 1H), 8.43 (d, 1H), 8.51 (d , 1H)
[준비예 5] Core5의 합성[Preparation Example 5] Synthesis of Core5
<단계 1> 4-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl의 합성<Step 1> Synthesis of 4-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl
[1,1':3',1''-terphenyl]-5'-ylboronic acid 대신 [1,1':4',1''-terphenyl]-2'-ylboronic acid을 사용한 것을 제외하고는 준비예 2의 단계 1과 동일한 과정을 수행하여 목적 화합물인 4-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl (30 g, 수율: 73%)을 얻었다.Preparation except that [1,1':4',1''-terphenyl]-2'-ylboronic acid was used instead of [1,1':3',1''-terphenyl]-5'-ylboronic acid By performing the same process as in Step 1 of Example 2, the target compound, 4-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl (30 g, yield: 73%) Got it.
1H-NMR: δ 7.46 (m, 7H), 7.78 (m, 4H), 8.02 (m, 2H), 8.18(m,2H), 8.55(s, 1H) 1 H-NMR: δ 7.46 (m, 7H), 7.78 (m, 4H), 8.02 (m, 2H), 8.18 (m,2H), 8.55 (s, 1H)
<단계 2> 7-chloro-1,4-diphenyl-9H-carbazole의 합성<Step 2> Synthesis of 7-chloro-1,4-diphenyl-9H-carbazole
4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 대신 4-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl 30g (77.75 mmol)을 사용한 것을 제외하고는 준비예 2의 단계 2와 동일한 과정을 수행하여 목적 화합물인 7-chloro-1,4-diphenyl-9H-carbazole (18 g, 수율: 65%)을 얻었다.4-chloro-2-nitro-5'-phenyl-1,1':2',1' instead of 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl The target compound, 7-chloro-1,4-diphenyl-9H-carbazole (18 g, yield: 65%) was performed in the same manner as in Step 2 of Preparation Example 2, except that 30 g (77.75 mmol) of'-terphenyl was used. ).
1H-NMR: δ 6.96 (d, 1H), 7.21 (m, 4H), 7.48 (m, 5H), 7.82(m, 2H), 8.13(m, 3H) 1 H-NMR: δ 6.96 (d, 1H), 7.21 (m, 4H), 7.48 (m, 5H), 7.82 (m, 2H), 8.13 (m, 3H)
<단계 3> Core5의 합성<Step 3> Synthesis of Core5
8-chloro-1,3-diphenyl-9H-carbazole 대신 7-chloro-1,4-diphenyl-9H-carbazole 18g (50.86 mmol)을 사용한 것을 제외하고는 준비예 1의 단계 3과 동일한 과정을 수행하여 목적 화합물인 Core5 (15 g, 수율: 68%)를 얻었다.Except for using 7-chloro-1,4-diphenyl-9H-carbazole 18g (50.86 mmol) instead of 8-chloro-1,3-diphenyl-9H-carbazole, the same procedure as in Step 3 of Preparation Example 1 was performed. The target compound, Core5 (15 g, yield: 68%) was obtained.
1H-NMR: δ 7.03 (d, 1H), 7.19 (m, 4H), 7.58 (m, 10H), 7.80 (m, 2H), 8.08 (d, 1H), 8.42 (d, 1H), 8.52 (d, 1H)
1 H-NMR: δ 7.03 (d, 1H), 7.19 (m, 4H), 7.58 (m, 10H), 7.80 (m, 2H), 8.08 (d, 1H), 8.42 (d, 1H), 8.52 ( d, 1H)
[준비예 6] Core6 의 합성[Preparation Example 6] Synthesis of Core6
<단계 1> 5-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl의 합성<Step 1> Synthesis of 5-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl
[1,1':3',1''-terphenyl]-5'-ylboronic acid 대신 [1,1':4',1''-terphenyl]-2'-ylboronic acid을 사용한 것을 제외하고는 준비예 3의 단계 1과 동일한 과정을 수행하여 목적 화합물인 5-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl (31 g, 수율: 75%)을 얻었다.Preparation except that [1,1':4',1''-terphenyl]-2'-ylboronic acid was used instead of [1,1':3',1''-terphenyl]-5'-ylboronic acid The target compound, 5-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl (31 g, yield: 75%), was prepared by performing the same process as in Step 1 of Example 3 Got it.
1H-NMR: δ 7.36 (m, 7H), 7.88 (m, 5H), 8.25 (m, 2H), 8.52(m, 2H) 1 H-NMR: δ 7.36 (m, 7H), 7.88 (m, 5H), 8.25 (m, 2H), 8.52 (m, 2H)
<단계 2> 6-chloro-1,4-diphenyl-9H-carbazole의 합성<Step 2> Synthesis of 6-chloro-1,4-diphenyl-9H-carbazole
4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl 대신 5-chloro-2-nitro-5'-phenyl-1,1':2',1''-terphenyl 31g (80.34 mmol)을 사용한 것을 제외하고는 준비예 2의 단계 2와 동일한 과정을 수행하여 목적 화합물인 6-chloro-1,4-diphenyl-9H-carbazole (28 g, 수율: 63%)을 얻었다.5-chloro-2-nitro-5'-phenyl-1,1':2',1' instead of 4-chloro-2-nitro-5'-phenyl-1,1':3',1''-terphenyl The target compound, 6-chloro-1,4-diphenyl-9H-carbazole (28 g, yield: 63%) was performed in the same manner as in Step 2 of Preparation Example 2, except that 31 g (80.34 mmol) of'-terphenyl was used. ).
1H-NMR: δ 7.12 (m, 5H), 7.48 (m, 6H), 7.82 (m, 2H), 8.23 (m, 2H), 12.18(s, 1H) 1 H-NMR: δ 7.12 (m, 5H), 7.48 (m, 6H), 7.82 (m, 2H), 8.23 (m, 2H), 12.18 (s, 1H)
<단계 3> Core6의 합성<Step 3> Synthesis of Core6
8-chloro-1,3-diphenyl-9H-carbazole 대신 6-chloro-1,4-diphenyl-9H-carbazole 18g (50.86 mmol)을 사용한 것을 제외하고는 준비예 1의 단계 3과 동일한 과정을 수행하여 목적 화합물인 Core6 (15 g, 수율: 68%)을 얻었다.Except for using 6-chloro-1,4-diphenyl-9H-carbazole 18g (50.86 mmol) instead of 8-chloro-1,3-diphenyl-9H-carbazole, the same procedure as in Step 3 of Preparation Example 1 was performed. The target compound, Core6 (15 g, yield: 68%) was obtained.
1H-NMR: δ 7.02 (d, 1H), 7.28 (m, 4H), 7.52 (m, 11H), 7.85 (m, 2H) 8.41(d, 1H), 8.52(d, 1H)
1 H-NMR: δ 7.02 (d, 1H), 7.28 (m, 4H), 7.52 (m, 11H), 7.85 (m, 2H) 8.41 (d, 1H), 8.52 (d, 1H)
[합성예 1] Inv 1의 합성[Synthesis Example 1] Synthesis of Inv 1
질소 기류 하에서 Core1 3 g (6.977 mmol), 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol), X-Phos 0.33g (0.697 mmol), Cs2CO3 6.81g (20.91 mmol) 및 100ml/25 ml의 1,4-Dioxane/H2O를 넣고 교반하였다. 40℃에서 Pd(OAc)2 0.24g (0.209mmol)을 넣고 110℃에서 12시간 동안 환류 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조한 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼크로마토그래피를 이용하여 목적 화합물인 Inv 1 (3.7g, 수율: 67%)을 얻었다.Core1 3 g (6.977 mmol), 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36 g under nitrogen stream (8.373 mmol), 0.33g (0.697 mmol) of X-Phos, 6.81g (20.91 mmol) of Cs 2 CO 3 and 1,4-Dioxane/H 2 O in 100ml/25ml were added and stirred. Pd(OAc) 2 0.24g (0.209mmol) was added at 40° C. and stirred under reflux at 110° C. for 12 hours. After completion of the reaction, extraction was performed with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure and then column chromatography to obtain the title compound Inv 1 (3.7g, yield: 67%).
GC-Mass (이론치: 788.99 g/mol, 측정치: 788 g/mol)
GC-Mass (Theoretical: 788.99 g/mol, Found: 788 g/mol)
[합성예 2] Inv 2의 합성[Synthesis Example 2] Synthesis of Inv 2
1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-4-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 2 (3.5 g, 수율: 58%)을 얻었다.9-([1,1'-biphenyl]- instead of 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole Except using 4-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol) Was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Inv 2 (3.5 g, yield: 58%).
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 3] Inv 41의 합성[Synthesis Example 3] Synthesis of Inv 41
1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 1,3,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 41 (3.5 g, 수율: 63%)을 얻었다.1,3,9-triphenyl-6-(4 instead of 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole Except for using,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol), the target compound was Inv 41 (3.5 g, yield: 63%) was obtained.
GC-Mass (이론치: 788.99 g/mol, 측정치: 788 g/mol)
GC-Mass (Theoretical: 788.99 g/mol, Found: 788 g/mol)
[합성예 4] Inv 42의 합성[Synthesis Example 4] Synthesis of Inv 42
1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-4-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 42 (3.4 g, 수율: 56%)를 얻었다.9-([1,1'-biphenyl]- instead of 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol) Except for the same procedure as in Synthesis Example 1, the target compound Inv 42 (3.4 g, yield: 56%) was obtained.
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 5] Inv 50의 합성[Synthesis Example 5] Synthesis of Inv 50
Core1 대신 Core3 (3g, mmol)을 사용하고 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 (9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 50 (3.5 g, 수율: 58%)을 얻었다.Instead of Core1, use Core3 (3g, mmol) and instead of 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole ( 9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H The target compound Inv 50 (3.5 g, yield: 58%) was obtained by performing the same procedure as in Synthesis Example 1, except for using -carbazole 5.0 g (8.373 mmol).
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 6] Inv 59의 합성[Synthesis Example 6] Synthesis of Inv 59
Core1 대신 Core3 (3g, mmol)을 사용하고 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 1,3,9-triphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 59 (3.7 g, 수율: 67%)을 얻었다.Use Core3 (3g, mmol) instead of Core1 and 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole instead of 1 Synthetic except for using ,3,9-triphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol) The same procedure as in Example 1 was carried out to obtain the title compound Inv 59 (3.7 g, yield: 67%).
GC-Mass (이론치: 788.99 g/mol, 측정치: 788 g/mol)
GC-Mass (Theoretical: 788.99 g/mol, Found: 788 g/mol)
[합성예 7] Inv 60의 합성[Synthesis Example 7] Synthesis of Inv 60
1,3,9-triphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-4-yl)-1,3-diphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Inv 60 (3.8 g, 수율: 63%)을 얻었다.9-([1,1'-biphenyl]- instead of 1,3,9-triphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4-yl)-1,3-diphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol) Except for the same procedure as in Synthesis Example 6, the target compound Inv 60 (3.8 g, yield: 63%) was obtained.
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 8] Inv 99의 합성[Synthesis Example 8] Synthesis of Inv 99
9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 1,3,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Inv 99 (4.0 g, 수율 72%)을 얻었다.9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H Using 1,3,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol) instead of -carbazole Except for the same procedure as in Synthesis Example 5, the target compound Inv 99 (4.0 g, yield 72%) was obtained.
GC-Mass (이론치: 788.99 g/mol, 측정치: 788 g/mol)
GC-Mass (Theoretical: 788.99 g/mol, Found: 788 g/mol)
[합성예 9] Inv 100의 합성[Synthesis Example 9] Synthesis of Inv 100
9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-4-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Inv 100 (4.2 g, 수율: 70%)을 얻었다.9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H 9-([1,1'-biphenyl]-4-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl instead of -carbazole )-9H-carbazole 5.0 g (8.373 mmol) was used, and the same procedure as in Synthesis Example 5 was carried out to obtain the target compound Inv 100 (4.2 g, yield: 70%).
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 10] Inv 101의 합성[Synthesis Example 10] Synthesis of Inv 101
9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Inv 101 (4.9 g, 수율: 65%)을 얻었다.9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H 9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl instead of -carbazole )-9H-carbazole 5.0 g (8.373 mmol) was carried out in the same manner as in Synthesis Example 5, except that the target compound Inv 101 (4.9 g, yield: 65%) was obtained.
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 11] Inv 102의 합성[Synthesis Example 11] Synthesis of Inv 102
9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1':3',1''-terphenyl]-5'-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.6 g (8.373 mmol)를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Inv 102 (4.5 g, 수율: 69%)를 얻었다.9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H 9-([1,1':3',1''-terphenyl]-5'-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3 instead of -carbazole ,2-dioxaborolan-2-yl)-9H-carbazole 5.6 g (8.373 mmol) was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Inv 102 (4.5 g, yield: 69%). Got it.
GC-Mass (이론치: 941.19 g/mol, 측정치: 941 g/mol)
GC-Mass (theoretical value: 941.19 g/mol, found: 941 g/mol)
[합성예 12] Inv 129의 합성[Synthesis Example 12] Synthesis of Inv 129
Core1 대신 Core4를 사용하고 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 1,4,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 129 (3.2 g, 수율: 58%)를 얻었다.Use Core4 instead of Core1 and 1,4,9- instead of 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole The same procedure as in Synthesis Example 1, except that triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol) was used. To obtain the target compound Inv 129 (3.2 g, yield: 58%).
GC-Mass (이론치: 788.99 g/mol, 측정치: 788 g/mol)
GC-Mass (Theoretical value: 788.99 g/mol, Measured value: 788 g/mol)
[합성예 13] Inv 130의 합성[Synthesis Example 13] Synthesis of Inv 130
1,4,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-4-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 12와 동일한 과정을 수행하여 목적 화합물인 Inv 130 (3.5 g, 수율: 58%)을 얻었다.9-([1,1'-biphenyl]- instead of 1,4,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol) Except for the same procedure as in Synthesis Example 12, the target compound Inv 130 (3.5 g, yield: 58%) was obtained.
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 14] Inv 149의 합성[Synthesis Example 14] Synthesis of Inv 149
Core1 대신 Core5를 사용하고 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 1,4,9-triphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 149 (3.8 g, 수율: 69%)를 얻었다.Use Core5 instead of Core1 and 1,4,9- instead of 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole The same procedure as in Synthesis Example 1, except that triphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol) was used. To obtain the title compound Inv 149 (3.8 g, yield: 69%).
GC-Mass (이론치: 788.99 g/mol, 측정치: 788 g/mol)
GC-Mass (Theoretical: 788.99 g/mol, Found: 788 g/mol)
[합성예 15] Inv 151의 합성[Synthesis Example 15] Synthesis of Inv 151
1,4,9-triphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-3-yl)-1,4-diphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 14와 동일한 과정을 수행하여 목적 화합물인 Inv 151 (3.8 g, 수율: 63%)을 얻었다.9-([1,1'-biphenyl]- instead of 1,4,9-triphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 3-yl)-1,4-diphenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol) Except for the same procedure as in Synthesis Example 14, the title compound Inv 151 (3.8 g, yield: 63%) was obtained.
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 16] Inv 165의 합성[Synthesis Example 16] Synthesis of Inv 165
Core1 대신 Core6를 사용하고 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 165 (3.5 g, 수율: 63%)를 얻었다.Use Core6 instead of Core1 and 1,4,9- instead of 1,3,9-triphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole The same procedure as in Synthesis Example 1, except that triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol) was used. To obtain the target compound Inv 165 (3.5 g, yield: 63%).
GC-Mass (이론치: 788.99 g/mol, 측정치: 788 g/mol)
GC-Mass (Theoretical: 788.99 g/mol, Found: 788 g/mol)
[합성예 17] Inv 166의 합성[Synthesis Example 17] Synthesis of Inv 166
1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-4-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 16과 동일한 과정을 수행하여 목적 화합물인 Inv 166 (3.7 g, 수율: 61%)을 얻었다.9-([1,1'-biphenyl]- instead of 1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol) Except for the same procedure as in Synthesis Example 16, the target compound Inv 166 (3.7 g, yield: 61%) was obtained.
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 18] Inv 167의 합성[Synthesis Example 18] Synthesis of Inv 167
1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-3-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 16과 동일한 과정을 수행하여 목적 화합물인 Inv 167 (3.6 g, 수율: 60%)을 얻었다.9-([1,1'-biphenyl]- instead of 1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 3-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol) Except for the same procedure as in Synthesis Example 16, the target compound Inv 167 (3.6 g, yield: 60%) was obtained.
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 19] Inv 168의 합성[Synthesis Example 19] Synthesis of Inv 168
1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1':3',1''-terphenyl]-5'-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.6 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 16과 동일한 과정을 수행하여 목적 화합물인 Inv 168 (4.2 g, 수율: 64%)을 얻었다.1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole instead of 9-([1,1':3', 1''-terphenyl]-5'-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.6 g Except for the use of (8.373 mmol), the same procedure as in Synthesis Example 16 was carried out to obtain the target compound Inv 168 (4.2 g, yield: 64%).
GC-Mass (이론치: 941.19 g/mol, 측정치: 941 g/mol)
GC-Mass (theoretical value: 941.19 g/mol, found: 941 g/mol)
[합성예 20] Inv 261의 합성[Synthesis Example 20] Synthesis of Inv 261
(9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Inv 261 (3.6 g, 수율: 65%)을 얻었다.(9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- Using 1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 4.36g (8.373 mmol) instead of 9H-carbazole Except that, the same procedure as in Synthesis Example 5 was performed to obtain the target compound Inv 261 (3.6 g, yield: 65%).
GC-Mass (이론치: 788.99 g/mol, 측정치: 788 g/mol)
GC-Mass (Theoretical: 788.99 g/mol, Found: 788 g/mol)
[합성예 21] Inv 262의 합성[Synthesis Example 21] Synthesis of Inv 262
(9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-4-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Inv 262 (3.8 g, 수율: 63%)를 얻었다.(9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9-([1,1'-biphenyl]-4-yl)-1,4-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- instead of 9H-carbazole Except for using yl)-9H-carbazole 5.0 g (8.373 mmol), the same procedure as in Synthesis Example 5 was performed to obtain the target compound Inv 262 (3.8 g, yield: 63%).
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 22] Inv 271의 합성[Synthesis Example 22] Synthesis of Inv 271
1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 16과 동일한 과정을 수행하여 목적 화합물인 Inv 271 (3.6 g, 수율: 60%)을 얻었다.9-([1,1'-biphenyl]- instead of 1,4,9-triphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 3-yl)-1,3-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 5.0 g (8.373 mmol) Except for the same procedure as in Synthesis Example 16, the target compound Inv 271 (3.6 g, yield: 60%) was obtained.
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 23] Inv 289의 합성[Synthesis Example 23] Synthesis of Inv 289
(9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 1,3,9-triphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole 2.21 g (7.66 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Inv 289 (3.8 g, 수율: 63%)를 얻었다.(9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 1,3,9-triphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole 2.21 g (7.66) instead of 9H-carbazole mmol) was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Inv 289 (3.8 g, yield: 63%).
GC-Mass (이론치: 865.09 g/mol, 측정치: 865 g/mol)
GC-Mass (Theoretical value: 865.09 g/mol, Measured value: 865 g/mol)
[합성예 24] Inv 290의 합성[Synthesis Example 24] Synthesis of Inv 290
(9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 9-([1,1'-biphenyl]-4-yl)-1,3-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole 5.0 g (8.373 mmol)을 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Inv 290 (4.3 g, 수율: 66%)을 얻었다.(9-([1,1'-biphenyl]-3-yl)-1,3-diphenyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 9-([1,1'-biphenyl]-4-yl)-1,3-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan instead of 9H-carbazole Except for the use of -2-yl)phenyl)-9H-carbazole 5.0 g (8.373 mmol), the same procedure as in Synthesis Example 5 was performed to obtain the target compound Inv 290 (4.3 g, yield: 66%).
GC-Mass (이론치: 941.19 g/mol, 측정치: 941 g/mol)
GC-Mass (theoretical value: 941.19 g/mol, found: 941 g/mol)
[비교합성예] C-1의 합성[Comparative Synthesis Example] Synthesis of C-1
질소 기류 하에서 3-bromo-6,9-diphenyl-9H-carbazole 10g (25.1 mmol), 3,9-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole acid 13.4g (30.12 mmol), K2CO3 10.4g (75.3 mmol) 및 1,4-Dioxane/H2O 120ml/40 ml를 넣고 교반하였다. 40℃에서 Pd(PPh3)4 0.87g (0.75 mmol)을 넣고 110℃에서 12시간 동안 환류 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조한 후 감압여과 하였다. 여과된 유기층을 감압증류한 뒤 컬럼크로마토그래피를 이용하여 목적 화합물인 C-1 (12 g, 수율: 75%)을 얻었다.3-bromo-6,9-diphenyl-9H-carbazole 10g (25.1 mmol), 3,9-diphenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 under nitrogen stream -yl)-9H-carbazole acid 13.4g (30.12 mmol), K 2 CO 3 10.4g (75.3 mmol) and 1,4-Dioxane/H 2 O 120ml/40ml were added and stirred. Pd(PPh 3 ) 4 0.87g (0.75 mmol) was added at 40°C and stirred at 110°C for 12 hours under reflux. After completion of the reaction, extraction was performed with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure and then column chromatography to give the title compound C-1 (12 g, yield: 75%).
GC-Mass (이론치: 636.9 g/mol, 측정치: 636 g/mol)
GC-Mass (Theoretical: 636.9 g/mol, Found: 636 g/mol)
[실시예 1 내지 24] 녹색 유기 전계 발광 소자의 제조[Examples 1 to 24] Preparation of green organic electroluminescent device
합성예 1 내지 24에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제조하였다.After the compounds synthesized in Synthesis Examples 1 to 24 were subjected to high-purity sublimation purification by a conventionally known method, a green organic electroluminescent device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, ITO (Indium tin oxide) was ultrasonically cleaned with distilled water on a glass substrate coated with a thin film with a thickness of 1500Å. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV and a vacuum evaporator. The substrate was transferred to the furnace.
이렇게 준비된 ITO 투명 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/합성예 1 내지 24에서 합성된 각각의 화합물 (40nm)/CBP + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 소자를 제조하였다. On the thus prepared ITO transparent substrate (electrode) m-MTDATA (60 nm)/TCTA (80 nm)/each compound synthesized in Synthesis Examples 1 to 24 (40 nm)/CBP + 10% Ir(ppy) 3 (30 nm) A device was manufactured by stacking in the order of /BCP (10 nm)/Alq 3 (30 nm)/LiF (1 nm)/Al (200 nm).
상기 m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of the m-MTDATA, TCTA, Ir(ppy) 3 , CBP and BCP are as follows.
[비교예 1] 녹색 유기 전계 발광 소자의 제조[Comparative Example 1] Preparation of green organic electroluminescent device
합성예 1에서 합성된 Inv 1을 사용하지 않은 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.
A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that Inv 1 synthesized in Synthesis Example 1 was not used.
[비교예 2] 녹색 유기 전계 발광 소자의 제조[Comparative Example 2] Preparation of green organic electroluminescent device
합성예 1에서 합성된 Inv 1 대신 비교합성예에서 합성된 C-1을 사용한 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.
A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that C-1 synthesized in Comparative Synthesis Example was used instead of Inv 1 synthesized in Synthesis Example 1.
[평가예 1][Evaluation Example 1]
실시예 1 내지 24 및 비교예 1, 2에서 각각 제조한 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For the green organic electroluminescent devices prepared in Examples 1 to 24 and Comparative Examples 1 and 2, respectively, the driving voltage, current efficiency and emission peak were measured at a current density of 10 mA/cm 2, and the results are shown in Table 1 below. .
상기 표 1에 나타낸 바와 같이, 본 발명의 화합물을 녹색 유기 전계 발광 소자의 발광 보조층에 적용할 경우(실시예 1 내지 24) 전류효율 및 구동전압이 우수한 것을 확인할 수 있었다.
As shown in Table 1, when the compound of the present invention is applied to the light emitting auxiliary layer of a green organic electroluminescent device (Examples 1 to 24), it was confirmed that the current efficiency and driving voltage were excellent.
[실시예 25 내지 48] 적색 유기 전계 발광 소자의 제조[Examples 25 to 48] Preparation of red organic electroluminescent device
합성예 1 내지 24에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제조하였다.After the compounds synthesized in Synthesis Examples 1 to 24 were subjected to high-purity sublimation purification by a commonly known method, a red organic electroluminescent device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, ITO (Indium tin oxide) was ultrasonically cleaned with distilled water on a glass substrate coated with a thin film with a thickness of 1500Å. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV and a vacuum evaporator. The substrate was transferred to the furnace.
이렇게 준비된 ITO 투명 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/합성예 1 내지 24에서 합성된 각각의 화합물 (40nm)/CBP + 10 % (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 소자를 제조하였다.On the thus prepared ITO transparent substrate (electrode) m-MTDATA (60 nm) / TCTA (80 nm) / each compound synthesized in Synthesis Examples 1 to 24 (40 nm) / CBP + 10% (piq) 2 Ir (acac) (30nm)/BCP (10 nm)/Alq 3 (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in this order to manufacture a device.
상기 m-MTDATA, CBP 및 BCP의 구조는 상기와 같고 (piq)2Ir(acac)의 구조는 하기와 같다.The structures of m-MTDATA, CBP and BCP are as described above, and the structure of (piq) 2 Ir(acac) is as follows.
[비교예 3] 적색 유기 전게 발광 소자의 제조[Comparative Example 3] Preparation of red organic electroluminescent device
합성예 1에서 합성된 Inv 1을 사용하지 않은 것을 제외하고는, 실시예 25와 동일하게 수행하여 적색 유기 전계 발광 소자를 제조하였다.
A red organic electroluminescent device was manufactured in the same manner as in Example 25, except that Inv 1 synthesized in Synthesis Example 1 was not used.
[비교예 4] 적색 유기 전계 발광 소자의 제조[Comparative Example 4] Preparation of red organic electroluminescent device
합성예 1에서 합성된 Inv 1 대신 비교합성예에서 합성된 C-1을 사용한 것을 제외하고는, 실시예 25와 동일하게 수행하여 적색 유기 전계 발광 소자를 제조하였다.
A red organic electroluminescent device was manufactured in the same manner as in Example 25, except that C-1 synthesized in Comparative Synthesis Example was used instead of Inv 1 synthesized in Synthesis Example 1.
[평가예 2][Evaluation Example 2]
실시예 25 내지 48 및 비교예 3, 4에서 각각 제조한 적색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.For the red organic electroluminescent devices prepared in Examples 25 to 48 and Comparative Examples 3 and 4, respectively, the driving voltage and current efficiency were measured at a current density of 10 mA/cm 2, and the results are shown in Table 2 below.
상기 표 2에 나타낸 바와 같이, 본 발명의 화합물을 적색 유기 전계 발광 소자의 발광 보조층에 적용할 경우(실시예 25 내지 48) 전류효율 및 구동전압이 우수한 것을 확인할 수 있었다.
As shown in Table 2, when the compound of the present invention is applied to the light emitting auxiliary layer of a red organic electroluminescent device (Examples 25 to 48), it was confirmed that the current efficiency and driving voltage were excellent.
[실시예 49 내지 72] 청색 유기 전계 발광 소자의 제조[Examples 49 to 72] Preparation of blue organic electroluminescent device
합성예 1 내지 24에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 청색 유기 전계 발광 소자를 제조하였다.The compounds synthesized in Synthesis Examples 1 to 24 were subjected to high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, ITO (Indium tin oxide) was ultrasonically cleaned with distilled water on a glass substrate coated with a thin film with a thickness of 1500Å. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV and a vacuum evaporator. The substrate was transferred to the furnace.
상기와 같이 준비된 ITO 투명 기판(전극) 위에, DS-205 (두산社) (80 nm)/NPB (15 nm)/ 합성예 1 내지 24에서 합성된 각각의 화합물(15nm)/ADN + 5 % DS-405 (두산社) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 소자를 제조하였다.On the ITO transparent substrate (electrode) prepared as above, DS-205 (Doosan Corporation) (80 nm) / NPB (15 nm) / each of the compounds synthesized in Synthesis Examples 1 to 24 (15 nm) / ADN + 5% DS -405 (Doosan Corporation) (30nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in the order to manufacture a device.
상기 ADN의 구조는 하기와 같다.The structure of the ADN is as follows.
[비교예 5] 청색 유기 전계 발광 소자의 제조[Comparative Example 5] Preparation of blue organic electroluminescent device
합성예 1에서 합성된 Inv 1을 사용하지 않은 것을 제외하고는, 실시예 49와 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.
A blue organic electroluminescent device was manufactured in the same manner as in Example 49, except that Inv 1 synthesized in Synthesis Example 1 was not used.
[비교예 6] 청색 유기 전계 발광 소자의 제조[Comparative Example 6] Preparation of blue organic electroluminescent device
합성예 1에서 합성된 Inv 1 대신 비교합성예에서 합성된 C-1을 사용한 것을 제외하고는, 실시예 49와 동일하게 수행하여 청색 유기 전계 발광 소자를 제조하였다.
A blue organic electroluminescent device was manufactured in the same manner as in Example 49, except that C-1 synthesized in Comparative Synthesis Example was used instead of Inv 1 synthesized in Synthesis Example 1.
[평가예 3][Evaluation Example 3]
실시예 49 내지 72 및 비교예 5, 6에서 각각 제조한 청색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 3에 나타내었다.For the blue organic electroluminescent devices prepared in Examples 49 to 72 and Comparative Examples 5 and 6, respectively, the driving voltage and current efficiency were measured at a current density of 10 mA/cm 2, and the results are shown in Table 3 below.
상기 표 3에 나타낸 바와 같이, 본 발명의 화합물을 청색 유기 전계 발광 소자의 발광 보조층에 적용할 경우(실시예 49 내지 72) 전류효율 및 구동전압이 우수한 것을 확인할 수 있었다.As shown in Table 3, when the compound of the present invention is applied to the light emitting auxiliary layer of a blue organic electroluminescent device (Examples 49 to 72), it was confirmed that the current efficiency and driving voltage were excellent.
Claims (6)
[화학식 1]
상기 화학식 1에서,
L은 단일결합, C6~C40의 아릴렌기, 또는 핵원자수 5 내지 40의 헤테로아릴렌기이고,
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,
상기 L의 C6~C40의 아릴렌기, 핵원자수 5 내지 40의 헤테로아릴렌기와, 상기 R1 및 R2의 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기, C6~C40의 아릴실릴기는, 각각 독립적으로 중수소, 할로겐기, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되는 하나 이상의 치환기로 치환 또는 비치환되며, 상기 치환기가 복수일 경우, 복수의 치환기는 서로 동일하거나 상이하다.Compound represented by the following formula (1):
[Formula 1]
In Formula 1,
L is a single bond, a C 6 ~ C 40 arylene group, or a heteroarylene group having 5 to 40 nuclear atoms,
R 1 and R 2 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, C of 6 ~ C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C of 3 ~ C 40 cycloalkyl group, a nuclear atom A number of 3 to 40 heterocycloalkyl groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkyl boron groups, C 6 to C 40 aryl boron groups, C 6 to C 40 arylphosphine groups, C 6 ~ C 40 is selected from the group consisting of aryl phosphine oxide group and C 6 ~ C 40 arylsilyl group,
The C 6 ~ C 40 arylene group of the L, a heteroarylene group having 5 to 40 nuclear atoms, the C 1 ~ C 40 alkyl group of the R 1 and R 2 , C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, 5 ~ 40 nuclear atoms heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 3 ~ C 40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclear atoms, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 40 aryl boron group, C 6 to C 40 arylphosphine group, C 6 ~ C 40 arylphosphine oxide group, C 6 ~ C 40 arylsilyl group, each independently deuterium, halogen group, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, nuclear atom number 5 ~ 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C group 40 arylboronic of, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl group one or more unsubstituted or substituted with substituents selected from the group consisting of a silyl group for the And, when the number of the substituents is plural, the plurality of substituents are the same as or different from each other.
상기 화학식 1로 표시되는 화합물이 하기 화학식 2 내지 7로 표시되는 화합물로 이루어진 군에서 선택되는 화합물:
[화학식 2]
[화학식 3]
[화학식 4]
[화학식 5]
[화학식 6]
[화학식 7]
상기 화학식 2 내지 7에서,
L, R1 및 R2는 제1항에서 정의한 바와 같다.The method of claim 1,
The compound represented by Formula 1 is a compound selected from the group consisting of compounds represented by Formulas 2 to 7:
[Formula 2]
[Formula 3]
[Formula 4]
[Formula 5]
[Formula 6]
[Formula 7]
In Formulas 2 to 7,
L, R 1 and R 2 are as defined in claim 1.
상기 L이 단일결합, 또는 페닐렌인 화합물.The method of claim 1,
The compound wherein L is a single bond or phenylene.
상기 R1 및 R2는 모두 C6~C40의 아릴기인 화합물.The method of claim 1,
The compounds R 1 and R 2 are both C 6 ~ C 40 aryl group.
상기 R1 및 R2가 각각 독립적으로 하기 S1 내지 S6으로 표시되는 구조로 이루어진 군에서 선택되는 화합물.
The compounds R 1 and R 2 are each independently selected from the group consisting of a structure represented by the following S1 to S6.
상기 1층 이상의 유기물층 중 적어도 하나가 제1항 내지 제5항 중 어느 한 항의 화합물을 포함하는 유기 전계 발광 소자.An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
An organic electroluminescent device in which at least one of the one or more organic material layers comprises the compound of any one of claims 1 to 5.
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| KR102450436B1 (en) | 2017-08-01 | 2022-10-04 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic electroluminescence device including the same |
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