CN116762493A - Novel heterocyclic compound and organic light-emitting element comprising same - Google Patents
Novel heterocyclic compound and organic light-emitting element comprising same Download PDFInfo
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- CN116762493A CN116762493A CN202180088816.2A CN202180088816A CN116762493A CN 116762493 A CN116762493 A CN 116762493A CN 202180088816 A CN202180088816 A CN 202180088816A CN 116762493 A CN116762493 A CN 116762493A
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- aryl
- independently
- alkyl
- heteroaryl
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims description 72
- 239000010410 layer Substances 0.000 claims description 59
- 239000000126 substance Substances 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 30
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 239000012044 organic layer Substances 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 22
- 125000005549 heteroarylene group Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 7
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 7
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 6
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 6
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- -1 polycyclic heterocyclic compound Chemical class 0.000 abstract description 40
- 125000003367 polycyclic group Chemical group 0.000 abstract description 14
- 239000011368 organic material Substances 0.000 abstract description 5
- ZHXBTDJWYYJMDG-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1.C1=CC=C2C3=CC=CC=C3OC2=C1 ZHXBTDJWYYJMDG-UHFFFAOYSA-N 0.000 abstract description 4
- SVQWSOXBNXJGQK-UHFFFAOYSA-N 1,4-dihydropentalene Chemical compound C1=CCC2=C1CC=C2 SVQWSOXBNXJGQK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000463 material Substances 0.000 description 96
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 229910052741 iridium Inorganic materials 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002019 doping agent Substances 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- 239000007983 Tris buffer Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000012300 argon atmosphere Substances 0.000 description 7
- 239000004327 boric acid Substances 0.000 description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CWNKMHIETKEBCA-UHFFFAOYSA-N alpha-Ethylaminohexanophenone Chemical compound CCCCC(NCC)C(=O)C1=CC=CC=C1 CWNKMHIETKEBCA-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Chemical group 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229920000767 polyaniline Polymers 0.000 description 5
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 238000005576 amination reaction Methods 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 150000001639 boron compounds Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000004696 coordination complex Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 3
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- HUOUJYMIUQWENN-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetrakis(4-methylphenyl)-4-phenylcyclohexa-2,4-diene-1,1-diamine Chemical compound C1=CC(C)=CC=C1N(C1(C=CC(=CC1)C=1C=CC=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 HUOUJYMIUQWENN-UHFFFAOYSA-N 0.000 description 2
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 2
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 2
- VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 description 2
- QWNCDHYYJATYOG-UHFFFAOYSA-N 2-phenylquinoxaline Chemical compound C1=CC=CC=C1C1=CN=C(C=CC=C2)C2=N1 QWNCDHYYJATYOG-UHFFFAOYSA-N 0.000 description 2
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 229960003168 bronopol Drugs 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000003838 furazanyl group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetic acid ester Natural products CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- CBSFHSKFQDSSQB-UHFFFAOYSA-N n-[4-[3,5-bis[4-(3-methylanilino)phenyl]phenyl]phenyl]-3-methylaniline Chemical compound CC1=CC=CC(NC=2C=CC(=CC=2)C=2C=C(C=C(C=2)C=2C=CC(NC=3C=C(C)C=CC=3)=CC=2)C=2C=CC(NC=3C=C(C)C=CC=3)=CC=2)=C1 CBSFHSKFQDSSQB-UHFFFAOYSA-N 0.000 description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 2
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
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- 235000021286 stilbenes Nutrition 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Abstract
The present invention relates to a novel heterocyclic compound and an organic light-emitting device including the same, wherein the heterocyclic compound of the present invention is a polycyclic heterocyclic compound having a polycyclic skeleton as a parent nucleus and having at least one amino substituent introduced therein, and is useful as an organic material for an organic light-emitting device, wherein the polycyclic skeleton is centered on 1, 4-dihydro-pentalene (1, 4-dihydro-pentalene) and dibenzofuran (dibenzofuran) is condensed on both sides of 1, 4-dihydro-pentalene.
Description
Technical Field
The present invention relates to a novel heterocyclic compound and an organic light-emitting element including the same.
Background
Generally, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance. An organic electronic device utilizing an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic layer between the two electrodes. In order to improve efficiency and stability of the organic electronic device, the organic layer is often formed of a multilayer structure, in which the multilayer structure is formed of different materials, for example, the organic layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like.
Materials used as an organic layer in an organic electronic element can be classified into a light-emitting material and a charge-transporting material (e.g., a hole-injecting material, a hole-transporting material, an electron-transporting material, and an electron-injecting material) and the like according to functions. Further, the light emitting material may be classified into a high molecular type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from an electron singlet excited state and a phosphorescent material derived from an electron triplet excited state according to a light emitting mechanism. Furthermore, the light emitting materials can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials required to achieve better natural colors according to the light emitting colors.
In particular, for the excellent life characteristics of organic electronic elements, various studies of an organic substance inserted into a hole transport layer or buffer layer (buffer layer) are being conducted, and for this purpose, a hole injection layer material which imparts high hole movement characteristics from an anode to an organic layer, and which is high in uniformity and low in crystallinity when a thin film is formed after deposition is required.
It is required to develop a hole injection layer material which delays the diffusion of a metal oxide from an anode electrode (ITO) to an organic layer, which is one of the causes of a reduction in the life of an organic electronic element, and which has stable characteristics against Joule heat (Joule heating) generated when the element is driven, i.e., has a high glass transition temperature. Furthermore, it is reported that the lower glass transition temperature of the hole transport layer material has a greater effect on the lifetime of the element, depending on the characteristics of reduced uniformity of the film surface upon driving the element. In addition, among the methods of forming OLED elements, deposition methods are dominant, and thus a material having a strong heat resistance property capable of withstanding such deposition methods for a long period of time is required.
In addition, when only one kind of substance is used for the light emitting material, the maximum light emitting wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity is lowered or the element efficiency is lowered due to the light emission attenuation effect, so that the light emitting material may use a host/dopant class in order to increase the color purity and increase the light emitting efficiency based on energy transfer. The principle is as follows: when a small amount of a dopant having a smaller band gap than the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transferred to the dopant to emit light of higher efficiency. At this time, the wavelength of the host is shifted to the wavelength band of the dopant, so that light of a desired wavelength can be obtained according to the kind of dopant used.
In order to fully develop the excellent characteristics of the organic electronic device, the materials constituting the organic material layer in the device (for example, hole injecting materials, hole transporting materials, light emitting materials, electron transporting materials, and electron injecting materials) should be supported by stable and effective materials.
Disclosure of Invention
Technical problem
The present invention is directed to a novel structure of a heterocyclic compound which can be used as an organic layer material of an organic light-emitting element.
Further, an object of the present invention is to provide an organic light-emitting element including the heterocyclic compound as an organic layer material.
Means for solving the technical problems
The present invention relates to a novel heterocyclic compound and an organic light-emitting device including the same, wherein the heterocyclic compound of the present invention is a polycyclic heterocyclic compound having a polycyclic skeleton as a parent nucleus and having at least one amino substituent introduced therein, and is useful as an organic material for an organic light-emitting device, wherein the polycyclic skeleton is centered on 1, 4-dihydro-pentalene (1, 4-dihydro-pentalene) and dibenzofuran (dibenzofuran) is condensed on both sides of 1, 4-dihydro-pentalene.
The present invention provides a heterocyclic compound represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
R a to R d Each independently hydrogen, C1-C60 alkyl or C6-C60 aryl;
L 1 to L 4 Each independently a single bond, a C6-C60 arylene group, or a C3-C60 heteroarylene group;
R 1 to R 8 Separately, independently of R 1 And R is 2 ；R 3 And R is 4 ；R 5 And R is 6 The method comprises the steps of carrying out a first treatment on the surface of the R is R 7 And R is 8 Can be linked to each other independently to form an aromatic ring-fused or unfused heterocyclic ring;
R 21 to R 24 Independently of one another, C1-C60 alkyl, halogenated C1-C60 alkylDeuterium, halogen, cyano, C3-C60 cycloalkyl, C1-C60 alkoxy, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl, C3-C60 heteroaryl, -NR 12 R 13 Nitro or hydroxy;
R 12 r is R 13 Each independently hydrogen, C1-C60 alkyl, C6-C60 aryl, or C3-C60 heteroaryl;
X 1 is NR (NR) 31 O or S;
R 31 is hydrogen, C1-C60 alkyl, C6-C60 aryl or C3-C60 heteroaryl;
the L is 1 To L 4 Arylene and heteroarylene of (2), and R 21 To R 24 The aryl and heteroaryl groups of (a) may be further substituted with one or more selected from the group consisting of C1-C60 alkyl, halo C1-C60 alkyl, deuterium, halogen, cyano, C3-C60 cycloalkyl, C1-C60 alkoxy, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl, C3-C60 heteroaryl, -NR' R ", nitro and hydroxy;
r 'and R' are each independently hydrogen, C1-C60 alkyl, C6-C60 aryl or C3-C60 heteroaryl;
a is an integer of 0 to 5, and when a is an integer of 2 or more, each R 21 May be the same or different from each other;
b is an integer of 0 to 7, and when b is an integer of 2 or more, each R 22 May be the same or different from each other;
c is an integer of 0 to 3, and when c is an integer of 2 or more, each R 23 May be the same or different from each other;
d is an integer of 0 to 4, and when d is an integer of 2 or more, each R 24 May be the same or different from each other;
p and q are each independently an integer from 0 to 4, r and s are each independently an integer from 0 to 2, provided that p, q, r and s are not all 0 at the same time;
the heteroarylene and the heteroaryl group include one or more heteroatoms selected from N, O, S and Se.
The present invention also provides an organic light-emitting element including an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contains the heterocyclic compound of formula 1.
Effects of the invention
The heterocyclic compound of the present invention is a polycyclic heterocyclic compound having a polycyclic skeleton as a parent nucleus, and at least one amino substituent introduced therein, and being useful as an organic material layer for an organic light-emitting element, wherein the polycyclic skeleton is centered on 1, 4-dihydro-cyclopentadiene (1, 4-dihydro-cyclopentadiene) and dibenzofuran (dibenzofuran) is condensed on both sides of the 1, 4-dihydro-cyclopentadiene. The heterocyclic compound can play a role of a light-emitting material, a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, and the like in an organic light-emitting element.
The heterocyclic compound of the present invention can be used as an organic material layer material for a light-emitting material, a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, etc. due to structural particularities, and an organic light-emitting element using the material has a high degree of hole mobility, and thus has a high efficiency, a low driving voltage, and surprisingly has improved life characteristics.
That is, the heterocyclic compound of the present invention has excellent electron mobility due to structural specificity, and thus improves the current characteristics of the element to strengthen the driving voltage, and further, leads to an increase in the electrical efficiency, thereby enabling the production of an organic light-emitting element having improved power consumption.
Detailed Description
The present invention will be described below, but unless otherwise defined, technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs, and descriptions of well-known functions and structures that may unnecessarily obscure the gist of the present invention will be omitted hereinafter.
Throughout this specification, unless the context requires otherwise, the word "comprise", and variations such as "comprises" or "comprising", will be understood to imply the inclusion of a stated step or feature or group of steps or features but not the exclusion of any other step or feature or group of steps or features.
In the present specification, "substituent", "radical", "group", "moiety" and "fragment" are used interchangeably.
In the present specification, "C A -C B "means" the number of carbon atoms is A or more and B or less ".
In this specification, "alkyl", "alkoxy" and other substituents including "alkyl" moieties include both straight or branched forms.
In the present specification, "alkyl" includes straight or branched chains having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 30, or specifically 1 to 20, preferably 1 to 10.
In the present specification, "alkenyl" includes straight or branched chains having 2 to 60 carbon atoms, and may be further substituted with other substituents. The alkenyl group may have a carbon number of 2 to 60, specifically 2 to 30, or specifically 2 to 20, preferably 2 to 10.
In the present specification, "alkynyl" includes straight or branched chains having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 30, or specifically 2 to 20, preferably 2 to 10.
In the present specification, "cycloalkyl" includes a single ring or multiple rings having 3 to 60 carbon atoms, and may be further substituted with other substituents. Wherein polycyclic refers to a group in which a cycloalkyl group is directly linked to or fused with another cycloalkyl group. The other cyclic group may be a cycloalkyl group, but may be other kinds of cyclic groups such as a heterocycloalkyl group, an aryl group, a heterocycle, and the like. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 30, or specifically 5 to 20.
In the present specification, "heterocycloalkyl group" includes a single ring or multiple rings having 2 to 60 carbon atoms including at least one hetero atom selected from N, O, S and Se, which may be further substituted with other substituents. Wherein polycyclic refers to a group in which a heterocycloalkyl group is directly connected to or fused with another cyclic group. Other cyclic groups may be heterocycloalkyl groups, but may also be other kinds of cyclic groups, such as cycloalkyl groups, aryl groups, heterocycles, and the like. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 30, or specifically 3 to 20.
In the present specification, "aryl" is an organic radical derived from aromatic hydrocarbons by removing one hydrogen, and includes a single ring or multiple rings having 6 to 60 carbon atoms, which may be further substituted with other substituents. Wherein polycyclic refers to a group in which an aryl group is directly linked or fused to another cyclic group. Other cyclic groups may be aryl groups, but may also be other kinds of cyclic groups, such as cycloalkyl groups, heterocycloalkyl groups, heterocyclo groups, and the like. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 30, or specifically 6 to 25, or specifically 6 to 20, or specifically 6 to 12. Specific examples of aryl groups include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, A group, a phenanthryl group (phenanthryl), a perylenyl group, a fluoranthenyl group (fluoranthenyl), a triphenylenyl group, a phenalenyl group (phenalenyl), a pyrenyl group (pyrenyl group), a tetracenyl group (tetracenyl group), a pentacenyl group (pentacenyl group), a fluorenyl group, an indenyl group, an acetylnaphthyl group, a fluorenyl group, or the like, or condensed rings thereof, but is not limited thereto.
In the present specification, "arylene" means a divalent organic radical derived from the above aryl group by removal of one hydrogen, the definition of which follows the definition of the above aryl group.
In the present specification, "heterocyclic group" includes a single ring or multiple rings having 2 to 60 carbon atoms which contain at least one hetero atom selected from N, O, S and Se, and which may be further substituted with other substituents. Heteroaryl groups are included within the scope of heterocyclic groups, which are heteroaromatic ring groups. Wherein polycyclic refers to a group in which a heterocyclic group is directly connected to or condensed with another cyclic group. Other cyclic groups may be heterocyclic groups, but may be other kinds of cyclic groups, such as cycloalkyl, heterocycloalkyl, aryl, and the like. The number of carbon atoms of the heterocyclic group may be 2 to 60, specifically 2 to 30, or specifically 3 to 25. Specific examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolidinyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl (furazanyl), oxadiazolyl (oxadizolyl), thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl (dioxanyl), triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridyl, naphthyridinyl, indolizinyl, indolyl, benzothiazyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, porphyrazinyl, and the like, or a fused ring thereof.
In the present specification, "heteroaryl" means an aryl group in which at least one heteroatom selected from N, O, S, and Se is included as an aromatic ring skeleton atom and the remaining aromatic ring skeleton atoms are carbon, which is a 5-to 6-membered monocyclic heteroaryl group, and a polycyclic heteroaryl group condensed with one or more benzene rings, and may be partially saturated. Furthermore, heteroaryl groups in the present invention also include forms in which more than one heteroaryl group is linked by a single bond. As a specific example, the method includes: monocyclic heteroaryl groups such as furyl, thienyl, pyrrolidinyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, isoxazolyl, oxazolyl, triazinyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like; polycyclic heteroaryl groups such as benzofuranyl, benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, and the like; etc., but is not limited thereto.
In the present specification, "heteroarylene" means a divalent organic radical derived from the above heteroaryl group by removal of one hydrogen, and its definition follows the definition of the above heteroaryl group.
The present invention relates to a novel heterocyclic compound and an organic light-emitting element including the same, and more particularly, the heterocyclic compound of the present invention can be represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
R a to R d Each independently hydrogen, C1-C60 alkyl or C6-C60 aryl;
L 1 to L 4 Each independently a single bond, a C6-C60 arylene group, or a C3-C60 heteroarylene group;
R 1 to R 8 Are respectively and independently Or R is 1 And R is 2 ；R 3 And R is 4 ；R 5 And R is 6 The method comprises the steps of carrying out a first treatment on the surface of the R is R 7 And R is 8 Can be linked to each other independently to form an aromatic ring-fused or unfused heterocyclic ring;
R 21 to R 24 Independently of one another, C1-C60 alkyl, halogenated C1-C60 alkyl, deuterium, halogen, cyano, C3-C60 cycloalkyl, C1-C60 alkoxy, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylC 1-C60 alkyl, C1-C60 alkyl C6-C60 aryl, C3-C60 heteroaryl, -NR 12 R 13 Nitro or hydroxy;
R 12 r is R 13 Each independently hydrogen, C1-C60 alkyl, C6-C60 aryl, or C3-C60 heteroaryl;
X 1 is NR (NR) 31 O or S;
R 31 is hydrogen, C1-C60 alkyl, C6-C60 aryl or C3-C60 heteroaryl;
the L is 1 To L 4 Arylene and heteroarylene of (2), and R 21 To R 24 The aryl and heteroaryl groups of (a) may be further substituted with one or more selected from the group consisting of C1-C60 alkyl, halo C1-C60 alkyl, hydrogen, halogen, cyano, C3-C60 cycloalkyl, C1-C60 alkoxy, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl, C3-C60 heteroaryl, -NR' R ", nitro and hydroxy;
R 'and R' are each independently hydrogen, C1-C60 alkyl, C6-C60 aryl or C3-C60 heteroaryl;
a is an integer of 0 to 5, and when a is an integer of 2 or more, each R 21 May be the same or different from each other;
b is an integer of 0 to 7, and when b is an integer of 2 or more, each R 22 May be the same or different from each other;
c is an integer of 0 to 3, and when c is an integer of 2 or more, each R 23 May be the same or different from each other;
d is an integer of 0 to 4, and when d is an integer of 2 or more, each R 24 May be the same or different from each other;
p and q are each independently an integer from 0 to 4, r and s are each independently an integer from 0 to 2, provided that p, q, r and s are not all 0 at the same time;
the heteroarylene and the heteroaryl group include one or more heteroatoms selected from N, O, S and Se.
Specifically, the heterocyclic compound of chemical formula 1 is a polycyclic heterocyclic compound having a polycyclic skeleton as a parent nucleus and incorporating at least one amino substituent of a specific structure, and is advantageously used as an organic layer material of an organic light-emitting element, wherein the polycyclic skeleton is centered on 1, 4-dihydro-cyclopentadiene (1, 4-dihydro-cyclopentadiene) and dibenzofuran (dibenzofuran) is condensed on both sides of the 1, 4-dihydro-cyclopentadiene.
The heterocyclic compound of chemical formula 1, by the above structural features, can reduce driving voltage, improve luminous efficiency and color purity, and exhibit surprisingly improved lifetime characteristics when used as an organic layer of an organic light-emitting element, particularly as a hole transporting substance of an organic light-emitting element.
In one embodiment, formula 1, the R a To R d Each independently is C1-C60 alkyl or C6-C60 aryl; l (L) 1 To L 4 Each independently is a single bond, a C6-C60 arylene or a C3-C60 heteroarylene group, the L 1 To L 4 The arylene and heteroarylene groups of (a) may be further substituted with one or more groups selected from C1-C60 alkyl, C6-C60 aryl and-NR 'R'; r 'and R' are each independently C6-C60 aryl or C3-C60 heteroaryl; r is R 1 To R 8 Are respectively and independentlyOr R is 1 And R is 2 ；R 3 And R is 4 ；R 5 And R is 6 The method comprises the steps of carrying out a first treatment on the surface of the R is R 7 And R is 8 Can be independently linked to each other to form an aromatic ring-fused heterocyclic ring; r is R 31 To R 35 Independently of one another, hydrogen, C1-C60 alkyl, deuterium, C6-C60 aryl, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl, C3-C60 heteroaryl or-NR 12 R 13 ；R 12 R is R 13 Each independently is a C6-C60 aryl or C3-C60 heteroaryl group; x is X 1 Is O or S; the R is 31 To R 35 The aryl and heteroaryl groups of (a) may be further substituted with one or more groups selected from the group consisting of C1-C60 alkyl, deuterium, C6-C60 aryl, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl and C3-C60 heteroaryl; p, q, r and s are integers from 0 to 2 independently of each other and 1.ltoreq.p+q+r+s.ltoreq.4 may be satisfied.
In order to achieve further improved element characteristics, the heterocyclic compound p+q+r+s may be an integer of 1 or 2.
In a specific example, the p+q+r+s may be an integer of 1.
In a specific example, the p+q+r+s may be an integer of 2.
In a specific example, q and s may be integers of 0, p and r may be integers of 0 to 2, and p+r may be an integer of 1 or 2, independently of each other.
In a specific example, p can be an integer of 1, and q, r, and s are integers of 0.
In a specific example, p can be an integer of 2, and q, r, and s are integers of 0.
In a specific example, r can be an integer of 1, and p, q, and s are integers of 0.
In a specific example, r can be an integer of 2, and p, q, and s are integers of 0.
In one embodiment, the heterocyclic compound may be represented by one of chemical formula 2 or chemical formula 3 below.
[ chemical formula 2]
[ chemical formula 3]
In the chemical formula 2 and the chemical formula 3,
R a to R d Each independently is a C1-C30 alkyl group;
L 1 l and L 3 Each independently is a single bond, a C6-C30 arylene or a C3-C30 heteroarylene group, the L 1 L and L 3 The arylene and heteroarylene groups of (a) may be further substituted with one or more groups selected from C1-C30 alkyl, C6-C30 aryl and-NR 'R';
r 'and R' are each independently C6-C30 aryl or C3-C30 heteroaryl;
R 1 、R 2 、R 5 R is R 6 Are respectively and independently Or R is 1 And R 5 And R is 6 Can be independently linked to each other to form an aromatic ring-fused heterocyclic ring;
R 31 to R 35 Independently of one another, are hydrogenC1-C30 alkyl, C6-C30 aryl, C6-C30 arylC 1-C30 alkyl, C1-C30 alkylC 6-C30 aryl, C3-C30 heteroaryl or-NR 12 R 13 ；
R 12 R is R 13 Each independently is a C6-C30 aryl or C3-C30 heteroaryl group;
the R is 31 To R 35 The aryl and heteroaryl groups of (a) may be further substituted with one or more groups selected from the group consisting of C1-C30 alkyl, C6-C30 aryl, C6-C30 arylC 1-C30 alkyl, C1-C30 alkylC 6-C30 aryl and C3-C30 heteroaryl;
p and r are each independently an integer of 1 or 2.
In one embodiment, the R a To R d May each independently be a C1-C20 alkyl group, and preferably may be a C1-C10 alkyl group.
In one embodiment, the heterocyclic compound may be represented by one of chemical formula 4 and chemical formula 5.
[ chemical formula 4]
[ chemical formula 5]
In the chemical formula 4 and the chemical formula 5,
L 1 l and L 3 Each independently is a single bond, a C6-C20 arylene or a C3-C20 heteroarylene group, the L 1 L and L 3 Arylene and heteroarylene groups of (a) may be further substituted with one or more groups selected from C1-C20 alkyl, C6-C20 aryl and-NR 'R';
r 'and R' are each independently C6-C20 aryl or C3-C20 heteroaryl;
R 1 、R 2 、R 5 R is R 6 Are respectively and independently
R 31 To R 35 Independently of one another, hydrogen, C6-C20-aryl, C3-C20-heteroaryl or-NR 12 R 13 ；
R 12 R is R 13 Each independently is a C6-C20 aryl or C3-C20 heteroaryl group;
the R is 31 To R 35 The aryl and heteroaryl groups of (a) may be further substituted with one or more selected from the group consisting of C1-C20 alkyl, C6-C20 aryl, C6-C20 arylC 1-C20 alkyl, C1-C20 alkylC 6-C20 aryl and C3-C20 heteroaryl.
In one embodiment, the L 1 To L 4 Can each independently be a single bond or a C6-C20 arylene group, said L 1 To L 4 May be further substituted with one or more groups selected from C6-C20 aryl and-NR 'R'; r 'and R' may each independently be a C6-C20 aryl or a C3-C20 heteroaryl.
In one embodiment, the R 1 、R 3 、R 5 R is R 7 Can be respectively and independently R 2 、R 4 、R 6 R is R 8 Can be independently-> R 31a 、R 31b 、R 31c 、R 33a 、R 33b 、R 34 R is R 35 Can be hydrogen or C6-C20 aryl independently of one another; r is R 12 R is R 13 May each independently be a C6-C20 aryl or C3-C20 heteroaryl group; x is X 1 May be O or S.
In one placeIn an embodiment, the L 1 To said L 4 Each independently is a single bond or a structure selected from the following, but is not limited thereto.
In the above-described structure, the first and second heat exchangers,
R L1 、R L2 r is R L3 Each independently hydrogen, C6-C20 aryl or NR 'R';
r 'and R' are each independently C6-C20 aryl or C3-C20 heteroaryl;
Z is CR Z1 R Z2 、NR Z3 O or S;
R Z1 r is R Z2 Each independently is C1-C20 alkyl or C6-C20 aryl;
R Z3 is a C6-C20 aryl group.
In a specific example, the L 1 To said L 4 Can be independently a single bond, R L1 R is R L2 Can each independently be hydrogen or NR 'R'; r 'and R' may each independently be a C6-C12 aryl or a C3-C12 heteroaryl.
In a specific example, the R 1 、R 3 、R 5 R is R 7 Can be respectively and independently R 2 ，R 4 ，R 6 R is R 8 Can be independently-> R 41 To R 43 R is R 51 To R 54 Can be hydrogen or C6-C12 aryl independently of one another; r is R 12 R is R 13 Can each independently be a C6-C12 aryl or C3-C12 heteroaryl group.
In one embodiment, in either the chemical formula 4 or the chemical formula 5, the L 1 L and L 3 Can each independently be a single bond or a C6-C12 arylene group, said L 1 L and L 3 May be further substituted with one or more groups selected from C6-C12 aryl and-NR 'R'; r 'and R' may each independently be a C6-C12 aryl or C3-C12 heteroaryl group; r is R 1 R is R 5 Can be respectively and independently R 2 R is R 6 Can be respectively and independently R 41 To R 43 R is R 51 To R 54 Can be hydrogen or C6-C12 aryl independently of one another; r is R 12 R is R 13 Can each independently be a C6-C12 aryl or C3-C12 heteroaryl group.
In one embodiment, the heterocyclic compound may be selected from the following structures, but is not limited thereto.
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The heterocyclic compound of one embodiment of the present invention is useful for an organic layer of an organic light-emitting element due to its structural specificity, and is particularly useful as a hole transport layer forming material in the organic layer.
The aforementioned compounds can be prepared based on the preparation examples/examples described later. Although representative examples are described in the preparation examples/examples described later, substituents may be added or removed as needed, and the positions of the substituents may be changed. The starting materials, the reaction conditions, and the like may be changed based on techniques well known in the art. Those skilled in the art will be able to perform the substitution of the remaining positions as desired by the type or position of the substituents using techniques well known in the art.
Further, the present invention provides an organic light emitting element comprising the heterocyclic compound of chemical formula 1.
Specifically, the organic light-emitting element of the present invention includes an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contains the heterocyclic compound of chemical formula 1.
However, the present invention is applicable to the structure of an organic light emitting element well known in the art. The scope of the present invention is not limited to such a laminated structure.
The organic light emitting element of the present invention may be prepared using materials and methods well known in the art, except that the heterocyclic compound of chemical formula 1 is contained in one or more layers in the organic layer.
The heterocyclic compound of chemical formula 1 may independently constitute one or more layers of the organic light-emitting element. However, the organic layer may be formed by mixing other substances as needed.
The heterocyclic compound of chemical formula 1 is useful as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like in an organic light emitting element. The heterocyclic compound can be used as a material for at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. As an example, the heterocyclic compound can be used as a hole injection and transport layer material for an organic light-emitting element. As an example, the heterocyclic compound may be used as an electron injection and transport layer material for an organic light-emitting element. As yet another example, the heterocyclic compound may be used as a light-emitting layer material of an organic light-emitting element. As another example, the heterocyclic compound can be used as a host material for a phosphorescent light-emitting layer of an organic light-emitting element. Preferably, the heterocyclic compound may be used as a hole transport layer material of an organic light-emitting element.
Hereinafter, although materials other than the above heterocyclic compounds are illustrated in the organic light-emitting element of the present invention, these materials are merely illustrative and not intended to limit the scope of the present invention, and these materials may be replaced with materials well known in the art.
The anode material may be a material having a large work function, and as a specific example, a metal such as vanadium, chromium, copper, zinc, gold, or an alloy thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO); such as ZnO: al or SnO2: a combination of metals and oxides of Sb; such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDT), polypyrrole, and polyaniline, but not limited thereto. In addition, the anode layer may be formed of only one type of the foregoing materials, or may be formed of a mixture of a plurality of materials, and a multilayer structure composed of a plurality of layers of the same composition or different compositions may be formed.
As the cathode material, a material having a low work function can be used, and as a specific example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof can be used; such as LiF/Al or LiO 2 Multi-layer structure of Al, etc.
As the hole injecting material, a known hole injecting material can be used, and for example, a phthalocyanine compound such as copper phthalocyanine (CuPc, copper phthalocyanine) disclosed in U.S. Pat. No. 4,356,429, or a star burst type amine derivative such as TCTA (tris (4-carbazol-9-ylphenyl) amine), m-MTDATA (4, 4',4″ -tris (methylphenylamino) triphenylamine, 4',4″ -tris (3-Methylphenylphenylamino) triphenylamine), m-MTDAPB (1, 3,5-tris [4- (3-methylphenylamino) phenyl ] benzene, 1,3,5-tris [4- (3-methylphenylamino) phenyl ] benzene), a conductive polymer having solubility such as tris (4-carbazol-9-ylphenyl) amine), or poly (p-phenylene) 84: PSS (Poly (3, 4-ethylenedioxythiophene) -Poly (styrenesulfonate), poly (3, 4-ethylenedioxythiophene) -Poly (styrnesulfonate)), pani/CSA (Polyaniline/camphorsulfonic acid, polyanline/Camphor sulfonic acid) or PANI/PSS (Polyaniline/Poly (4-styrene-sulfonate)), polyanline/Poly (4-styrene-sulfonate)), and the like.
The hole-transporting material may contain the heterocyclic compound of an embodiment of the present invention alone or in combination with a known hole-transporting material.
Specifically, the hole transporting material may contain the heterocyclic compound of an embodiment of the present invention, but may be used together with pyrazoline derivatives, aromatic amine derivatives, stilbene-based derivatives, triphenyldiamine derivatives, and the like, and may also be used together with a low-molecular or high-molecular material. Specific examples thereof include NPB (N, N '-Bis (naphthalen-1-yl) -N, N' -Bis (phenyl) -benzidine, N, N '-Bis (naphthalen-1-yl) -N, N' -Bis (phenyl) -benzoine), NPD (N, N '-Bis (naphthalen-1-yl) -N, N' -Bis (phenyl) -2,2'-dimethylbenzidine, N, N' -Bis (naphthalen-1-yl) -N, N '-Bis (phenyl) -2,2' -dimethyllbenzidine), mCP (1, 3-Bis (N-carbazolyl) benzene, 1,3-Bis (N-carbazolyl) benzone) and TPD (N, N '-Bis (3-methylphenyl) -N, N' -diphenyl benzidine, N, N '-Bis (3-methylphenyl) -N, N' -diphenylbenzizidine), TTB (N, N, N ', N' -tetrakis (4-methylphenyl) - (1, 1 '-biphenyl) -4,4-diamine, N, N, N', N '-tetrakis (4-methylphenyl) - (1, 1' -biphenyl) -4, 4-diamine), TTP (N1, N4-diphenyl-N1, N4-Bis-m-toluene-1, 4-diamine, N1, N4-diphenyl-N1, N4-dim-tolyllbenzen-1, 4-diamine), ETPD (N, n ' -bis (4-methylphenyl) -N, N ' -bis (4-ethylphenyl) - [1,1' - (3, 3' -dimethyl) biphenyl ] -4,4' -diamine, N, N ' -bis (4-methylphenyl) -N, N ' -bis (4-ethylphenyl) - [1,1' - (3, 3' -dimethyl) biphenyl ] -4,4' -diamine), VNPB (N4, N4' -bis (naphthalen-1-yl) -N4, N4' -bis (4-vinylphenyl) biphenyl-4,4' -diamine, N4, N4' -di (nanothalen-1-yl) -N4, N4' -bis (4-vinylphenyl) biphen-4, 4' -diamine), ONPB (N4, N4' -bis (4- (6- ((3-ethyloxetan-3-yl) methoxy) hexyl) phenyl) -N4, N4' -diphenyl biphenyl-4,4' -diamine, N4, N4' -bis (4- (6- ((3-ethyloetan-3-yl) method) phenyl) -N4, N4' -diphenylbiphenyl-4,4' -diamine), OTPD (N4, N4' -bis (4- (6- ((3-ethyloxetan-3-yl) methoxy) hexyl) phenyl) -N4, low molecular hole transporting substances such as N4' -diphenyl biphenyl-4,4' -diamine, N4' -bis (4- (6- ((3-ethyloxy-3-yl) method) hexyl) phenyl) -N4, N4' -diphenylbiphenyl-4,4' -diamine; PVK (poly-N-vinylcarbazole), polyaniline, (phenylmethyl) polysilane, and the like.
Examples of the electron transporting material include an oxazole derivative, anthraquinone dimethane and its derivative, benzoquinone and its derivative, naphthalenone and its derivative, anthraquinone and its derivative, tetracyanoanthraquinone dimethane and its derivative, fluoroenone derivative, diphenyldicyanoethylene and its derivative, diphenylquinone derivative, and metal complex of 8-hydroxyquinoline and its derivative, and not only a low molecular substance but also a high molecular substance can be used. As a specific example, TSPO1 (diphenyl [4- (triphenylsilyl) phenyl)]Phosphine oxide, diphenyl [4- (triphenylsilyl) phenyl ]]phospholane oxide), TPBI (1, 3,5-tris (N-phenylbenzimidazol-2-yl) benzene, 1,3,5-tris (N-phenylbenzozinmidazol-2-yl) benzene); alq 3 (tris (8-hydroxyquinoline) aluminum, tris (8-hydroxyquinoline) aluminum); BCP (2, 9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthrine); such as PBD (2- (4-biphenyl) -5- (4-tert-butyl-phenyl) -1,3, 4-oxadiazole, 2- (4-biphenyl) -5- (4-tert-butyl-phenyl) -1,3, 4-oxadifole), TAZ (3- (4-biphenyl) -4-phenyl-5- (4-tert-butyl-phenyl) -1,2,4-triazole, 3- (4-biphenyl) -4-phenyl-5- (4-tert-butyl-phenyl) -1,2, 4-triazole), OXD-7 (1, 3-bis [2- (4-tert-butylphenyl) -1,3, 4-oxadiazol-5-yl) ]Benzene, 1,3-bis [2- (4-tert-butyl phenyl) -1,3,4-oxadiazo-5-yl]benzene) azole compound; tris (phenylquinoxaline) (tris (phenylquinoxaline), TPQ); tmPyPB (3, 3'- [5' - [3- (3-pyridyl) phenyl)][1,1':3',1' -triphenylene]-3, 3' -diyl]Bipyridine, 3'- [5' - [3- (3-Pyridinyl) phenyl ]][1,1’:3’,1”-terphenyl]-3,3”-diyl]bispyridine), and the like, but is not limited thereto.
As the electron injection material, LIF or Liq (lithium quinolinate, lithium quinolate) is typically used in the art, for example, but is not limited thereto.
The light-emitting material may be a red, green or blue light-emitting material, and two or more light-emitting materials may be mixed as necessary. In addition, a fluorescent material may be used as the light emitting material, but a phosphorescent material may also be used. As the light-emitting material, a material that emits light by combining holes and electrons injected from the anode and the cathode, respectively, may be used alone, but a material in which a host material and a dopant material participate in light emission together may also be used.
The light-emitting layer may be formed of a light-emitting material by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, and more specifically, in forming the light-emitting layer by a vacuum deposition method, deposition conditions thereof may be generally selected from a range of conditions almost identical to those of forming the hole injection layer, although they differ depending on the compound used. In addition, as a light-emitting layer material, a known compound can be used as a host or a dopant.
In addition, as an example, as the fluorescent dopant of the light-emitting layer material, IDE102 or IDE105, BD-331 or BD-142 (N) 6 ,N 12 -bis (3, 4-dimethylphenyl) -N 6 ,N 12 -a di-rice base-6,12-diamine, N 6 ,N 12 -bis(3,4-dimethylphenyl)-N 6 ,N 12 -dimesityl chrysene-6, 12-diamine); phosphorescent dopants as materials for the light-emitting layer can be formed from green phosphorescent dopants Ir (ppy) 3 (tris (2-phenylpyridine) iridium), blue phosphorescent dopant F2Irpic (iridium (III) bis [4, 6-difluorophenyl) -pyridinato-N, C2']Pyridine methylAcid salt) and red phosphorescent dopant RD61 from UDC company.
The phosphorescent dopant is a compound capable of emitting light from triplet excitons, and is not particularly limited as long as light is emitted from triplet excitons. As a specific example, a metal complex containing one or more metals selected from Ir, ru, pd, pt, os, re, and the like may be used, and a porphyrin metal complex or a orthometalated metal complex may be used.
The porphyrin metal complex may specifically be a porphyrin platinum metal complex.
The orthometalated metal complex may be a substance containing 2-phenylpyridine (2-phenyl pyridine, ppy) derivative, 7, 8-benzoquinoline derivative, 2- (2-thienyl) pyridine (2- (2-thienyl) pyridine, tp) derivative, 2- (1-naphthyl) pyridine (2- (1-naphthyl) pyridine, npy) derivative, 2-phenylquinoline (2-phenyl quinoline, pq) derivative, or the like as a ligand. In this case, these derivatives may have a substituent as required. Ligands other than the above-mentioned ligands, such as acetylacetonate (acac), picric acid (picric acid) and the like, may be further contained as auxiliary ligands. Specific examples thereof include iridium bithiophene acetylacetonate (bisthienylpyridine acetylacetonate Iridium) and bis (2-benzo [ b ] ]Thiophen-2-yl-pyridine) (acetylacetonate) iridium (III) (bis (2-benzob)]thiophen-2-yl-pyridine)(acetylacetonato)iridium(III)，Ir(btp) 2 (acac)), bis (2-phenylbenzothiazole) (acetylacetonate) iridium (bis (2-phenylbenzothiazole) iridium (III), ir (bt) 2 (acac)), bis (1-phenylisoquinoline) (acetylacetonate) Iridium (III) (bis (1-phenylisoquinoline) (acetoacetonato) Iridium (III), ir (piq) 2 (acac)), tris (1-phenylisoquinoline) iridium (III), ir (piq) 3 ) Tris (2-phenylpyridine) iridium (III), ir (ppy) 3 ) Tris (2-biphenylpyridine) iridium (tris (2-biphenylpyridine) iridium), tris (3-biphenylpyridine) iridium (tris (3-biphenylpyridine) iridium), tris (4-biphenylpyridine) iridium (tris (4-biphenylpyridine) iridium), and the like, but are not limited thereto.
In addition, when used together with phosphorescent dopants in the light-emitting layer, in order to prevent diffusion of triplet excitons or holes to the electron transport layer, a hole-inhibiting material (HBL) may be further laminated by a vacuum deposition method or a spin coating method. The hole-inhibiting material that can be used at this time is not particularly limited, but may be arbitrarily selected from known hole-inhibiting materials. For example, oxadiazole derivatives and triazole derivatives such as phenanthroline derivatives may be used, and Balq (bis (8-hydroxy-2-methylquinoline) -aluminum bisphenolate, bis (8-hydroxy-2-methylquinoline) -aluminium biphenoxide), phenanthroline (phenanthroline) compounds (BCP (bathocuproine) of UDC).
The present invention will be described in more detail with reference to examples, which are given by way of illustration only and are not intended to limit the scope of the invention.
EXAMPLE 1 preparation of Compound P1 and Compound P2
Preparation of Compound P-8
To 290mL of DMF (dimethylformamide) was added 10g (57.14 mmol) of 1-bromo-4-iodobenzene (1-bromo-4-iodobenzene), 5.77g (68.57 mmol) of 2-methyl-3-butin-2-ol (2-methyl-3-yne-2-ol), 0.64g (2.86 mmol) of palladium (II) acetate, pd (OAc) 2 ) 1.63g (8.57 mmol) of copper (I) Iodide (CuI), 2.29g (8.57 mmol) of triphenylphosphine (PPh) 3 ) 12mL (114.28 mmol) of diethylamine (Et) 2 NH), the mixture was stirred under a nitrogen atmosphere at 30 ℃ for 10 minutes. The reaction solution was then stirred under reflux. After the completion of the reaction, after extraction with ethylenediamine aqueous solution and MC (dichloromethane, methylene chloride), magnesium sulfate was added to the MC layer to control moisture, followed by filtration. After the solvent was removed, column chromatography purification was performed using EA (ethyl acetate) and Hex (hexane) to obtain 8.86g (87%) of the target compound P-8.
Preparation of Compound P-7
After 10g (56.11 mmol) of Compound P-8 was dissolved in 170mL of MC, 17.09g (67.33 mmol) of iodine (iodine, I) 2 ) And stirred at room temperature. After the completion of the reaction, extraction was performed using an aqueous solution of sodium thiosulfate, and an organic layer was collected. After the solvent was removed from the organic layer, column chromatography purification was performed using EA and Hex, thereby obtaining 17.66g (76%) of the target compound P-7.
Preparation of Compound P-6
10g (24.15 mmol) of Compound P-7 are stirred in 120mL of diethyl ether under argon and the temperature is reduced to-78 ℃. At this temperature, 19mL (28.98 mmol) of butyllithium (n-butylllithium/1.6M solution in hex.) was slowly added while stirring. After one hour, 2.3mL (31.40 mmol) of acetone was added at the same temperature and stirred under argon atmosphere for one hour. Then, the temperature was slowly raised for 24 hours until room temperature was reached, and stirring was performed. After the completion of the reaction, the reaction was completed with 1N aqueous HCl, and the organic layer was collected by MC extraction. After the solvent was removed from the organic layer, column chromatography purification was performed using EA and Hex, thereby obtaining 5.18g (62%) of the target compound P-6.
Preparation of Compound P-5
To toluene/ethanol/water (volume ratio 4:1:1, 110 mL) was added 10g (28.89 mmol) of compound P-6, 7.70g (34.66 mmol) of 2- (4-fluorophenyl) -4, 5-tetramethyl-1,3, 2-dioxapentaborane (2- (4-fluorophenyl) -4, 5-tetramethy-1, 3, 2-dioxaborolane), 7.99g (57.78 mmol) of potassium carbonate (potassium carbonate, K) 2 CO 3 ) After that, the mixture was stirred under nitrogen at 30℃for 10 minutes. Then, 1.67g (1.45 mmol) of tetrakis (triphenylphosphine) palladium (Pd (PPh) 3 ) 4 ) After that, reflux was performed at 120 ℃. After the reaction was completed, filtration was performed using celite (celite) and florisil (florisil), and washing was performed using MC. Column chromatography purification was performed using MC and Hex, thereby obtaining 7.56g (85%) of the target compound P-5.
Preparation of Compound P-4
To 160mL of MC was added 10g (31.81 mmol) of Compound P-5, and the temperature was lowered to 0℃while stirring. To this was added 4.7mL (38.17 mmol) of boron trifluoride diethyl etherate (boron trifluoride diethyl etherate, BF) 3 OEt 2 ) And stirred at 0 ℃ for one hour. Then, the temperature was slowly raised to room temperature while stirring for 24 hours. After completion of the reaction, EA and H were used 2 O was extracted, followed by removal of the solvent and column chromatography purification using Hex and EA, to obtain 6.98g (74%) of the target compound P-4.
Preparation of Compound P-3
To 170mL of NMP (N-methyl-2-pyrrolidone, N-methyl-2-pyrrosidone) was added 10g (33.74 mmol) of compound P-4 and stirred under argon atmosphere. To this was added 4.30mL (40.49 mmol) of 2-bromophenol (2-bronopol) and 5.60g (40.49 mmol) of K 2 CO 3 After that, the mixture was stirred under nitrogen at 30℃for 10 minutes. Then stirred at 80℃for 24 hours. After the reaction was completed, filtration was performed using celite (celite) and florisil (florisil), followed by washing with MC. Column chromatography purification was performed using MC and Hex, thereby obtaining 11.52g (76%) of the target compound P-3.
Preparation of Compound P-2
To 170mL of NMP was added 10g (33.74 mmol) of compound P-3 and stirred under argon atmosphere. To this was added 8.40g (40.49 mmol) of 2-bromo-6-chlorophenol (2-bromo-6-chlorophenol) and 5.60g (40.49 mmol) of K 2 CO 3 After that, the mixture was stirred under nitrogen at 30℃for 10 minutes. Then, the mixture was stirred at 140℃for 24 hours. After the reaction was completed, filtration was performed using celite (celite) and florisil (florisil), followed by washing with MC. Column chromatography purification was performed using MC and Hex, thereby obtaining 13.97g (65%) of the target compound P-2.
Preparation of Compound P-1
To 80mL of DMF was added 10g (15.70 mmol) of Compound P-2 and the mixture was stirred inStirring and dissolving in argon atmosphere and room temperature. To this was added 0.53g (2.36 mmol) of Pd (OAc) 2 And 4.34g (31.4 mmol) of K 2 CO 3 And stirred at 150℃under reflux for 24 hours. After the reaction was completed, water was added to terminate the reaction. The resulting solid was filtered and washed multiple times with Hex. Column chromatography purification was performed using MC and Hex, thereby obtaining 4.55g (61%) of the target compound P-1.
Preparation of Compound P1
The target compound P1 was obtained by a Suzuki coupling reaction using the compound P-1 and a boron compound and a palladium catalyst.
To toluene/ethanol/water (volume ratio 4:1:1, 100 mL) was added compound P-1 (1 equivalent), substituted boric acid or boric acid ester compound (1, 2 equivalents (eq.)), pd (PPh) 3 ) 4 (0.05 eq.) and K 2 CO 3 (2 equivalents) and stirring under reflux at 120℃under a nitrogen atmosphere. After completion of the reaction, filtration was performed using celite (celite) and florisil, and washing was performed using MC. The target compound P1 was obtained by recrystallization purification using EA and Hex.
Preparation of Compound P2
The target compound P2 was obtained by palladium amination (palladium amination) using a compound P-1 and a secondary amine compound and a palladium catalyst.
To toluene was added compound P-1 (1 equivalent), secondary amine (secondary amine) compound (1, 2 equivalent), tris (dibenzylideneacetone) dipalladium (Pd) 2 (dba) 3 ) (0.05 eq.) tris (t-butyl) phosphine (P (t-Bu) 3 ) (0.15 eq.) and sodium t-butoxide (NaOt-Bu) (2 eq.) were stirred under reflux in an argon atmosphere at 120 ℃. After the reaction was completed, filtration was performed using celite (celite) and florisil (florisil), followed by washing with MC. The target compound P2 was obtained by recrystallization purification using EA and Hex.
The structures of the substituted boric acid, boric acid ester and secondary amine compounds as reactants, and the structures and yields of the compounds P1 and P2 after the preparation are shown in table 1 below. However, the structures of the boron compound and the secondary amine compound as reactants are not limited to the following structures.
TABLE 1
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EXAMPLE 2 preparation of Compound P3 and Compound P4
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Preparation of Compound Q-3
To 170mL of NMP was added 10g (33.74 mmol) of compound P-4 and stirred under argon. 7.52mL (70.85 mmol) of 2-bromophenol (2-bronopol) and 13.99g (101.22 mmol) of K were added thereto 2 CO 3 After that, the mixture was stirred under nitrogen at 30℃for 10 minutes. Then, the mixture was stirred at 150℃for 24 hours. After the reaction was completed, filtration was performed using celite (celite) and florisil (florisil), followed by washing with MC. Column chromatography purification was performed using MC and Hex, thereby obtaining 12.40g (61%) of the target compound Q-3.
Preparation of Compound Q-2
To 80mL of DMF was added 10g (16.60 mmol) of the target compound Q-3, and the mixture was stirred under argon at room temperature to dissolve the compound. To this was added 0.56g (2.49 mmol) of Pd (OAc) 2 And 5.74g (41.5 mmol) of K 2 CO 3 And stirred at 150℃under reflux for 24 hours. After the reaction was completed, water was added to terminate the reaction. For the generated solidFiltration was performed and washed multiple times with Hex. Column chromatography purification was performed using MC and Hex, thereby obtaining 4.55g (61%) of the target compound Q-2.
Preparation of Compound Q-1
To 80mL of tetrachloromethane (CCl) 4 ) To this solution, 10g (22.70 mmol) of Compound Q-2 was added and the mixture was stirred and dissolved in an argon atmosphere at room temperature. To this was added 4.56g (20.43 mmol) of copper (II) bromide, cuBr 2 ) And 4.64g (45.40 mmol) of alumina (Al 2 O 3 ) And stirred at 40℃for 24 hours. After the reaction was completed, water was added to terminate the reaction. The resulting solid was filtered and washed multiple times with Hex. Column chromatography purification was performed using MC and Hex, thereby obtaining 6.25g (53%) of the target compound Q-1.
Preparation of Compound P3
The target compound P3 was obtained by a Suzuki coupling reaction using compound Q-1 and a boron compound and a palladium catalyst.
To toluene/ethanol/water (volume ratio 4:1:1, 100 mL) was added compound Q-1 (1 eq), substituted boric acid or borate compound (1, 2 eq), pd (PPh) 3 ) 4 (0.05 eq.) and K 2 CO 3 (2 equivalents) and stirring under reflux at 120℃under a nitrogen atmosphere. After completion of the reaction, filtration was performed using celite (celite) and florisil, and washing was performed using MC. The target compound P3 was obtained by recrystallization purification using EA and Hex.
Preparation of Compound P4
The target compound P4 was obtained by palladium amination (palladium amination) using the compound Q-1 and a secondary amine compound and a palladium catalyst.
Adding compound Q-1 (1 equivalent), secondary amine (1, 2 equivalent), pd to toluene 2 (dba) 3 (0.05 eq), P (t-Bu) 3 (0.15 eq.) and NaOt-Bu (2 eq.) were stirred under reflux in an argon atmosphere at 120 ℃. After the completion of the reaction, the reaction mixture,filtration was performed using celite (celite) and florisil (florisil), followed by washing with MC. The target compound P4 was obtained by recrystallization purification using EA and Hex.
The structures of the substituted boric acid, boric acid ester and secondary amine compounds as reactants, and the structures and yields of the compounds P3 and P4 after the preparation are shown in table 2 below. However, the structures of the boron compound and the secondary amine compound as reactants are not limited to the following structures.
TABLE 2
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The compounds prepared in the above examples are shown in Table 3 below 1 H NMR and MS values.
TABLE 3
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Example 3 preparation and evaluation of organic light-emitting element
The compounds obtained in examples were used as hole transport layers, respectively, and organic light-emitting elements were fabricated by a conventional method.
First, an ITO substrate was set on a substrate holder of a vacuum deposition apparatus, and 2-TNATA (4, 4',4"-Tris [2-naphthyl (phenyl) amino ] triphenylamine, 4',4" -Tris [2-naphthyl (phenyl) amino ] triphenylamine) was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer of 10nm thickness, and then the heterocyclic compound prepared in the examples of the present invention was vacuum deposited to form a hole transport layer of 20nm thickness.
Next, BD-331 (Idemitsu corporation) was used as a light-emitting dopant and ADN (9, 10-Bis (2-naphthyl) anthracene, 9,10-Bis (2-naphthalenyl)) was used as a host material, and the doping concentration was fixed at 4%, and a light-emitting layer was deposited on the hole transport layer to a thickness of 30 nm.
Next, alq3 (tris (8-hydroxyquinoline) aluminum) was vacuum deposited on the light emitting layer at a thickness of 40nm as an electron transporting layer. Then, after depositing an alkali metal halide LiF at a thickness of 0.2nm and then depositing Al at a thickness of 150nm, al/LiF was used as a cathode, thereby manufacturing an organic light emitting element.
Comparative examples 1 to 3
An organic light-emitting element was manufactured in the same manner as in example 3 above, except that the hole-transporting substance used the following comparative compound a, comparative compound B, or comparative compound C instead of the heterocyclic compound of the present invention.
The organic light-emitting elements manufactured by example 3 and comparative examples 1 to 3 of the present invention were applied with a forward DC bias voltage, and Electroluminescent (EL) characteristics were measured using PR-650 of the company Photoesearch, and at 300cd/m 2 The T95 lifetime was measured by a lifetime meter manufactured by mcscience company. The measurement results are shown in table 4 below. T95 represents a time until the luminance of the light emitting element becomes 95% of the initial luminance.
TABLE 4
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As is clear from table 4 above, the heterocyclic compound developed in the present invention has a superior light-emitting property as a hole-transporting material compared with the conventional hole-transporting material, and can induce an increase in power efficiency by reducing the driving voltage, thereby improving the power consumption, and also shows a significant increase in life characteristics.
Therefore, the heterocyclic compound of the present invention can be used as an organic layer forming material such as a hole transporting material, etc., so that an organic electroluminescent element exhibiting low driving voltage, excellent color purity, high luminous efficiency and long lifetime characteristics can be produced. It is also apparent that the same effect can be obtained even when the compound of the present invention is used in other organic layers of an organic electroluminescent element, for example, a light-emitting layer, a hole injection layer, an electron transport layer, and the like.
Claims (9)
1. A heterocyclic compound represented by the following chemical formula 1,
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
R a to R d Each independently hydrogen, C1-C60 alkyl or C6-C60 aryl;
L 1 to L 4 Each independently a single bond, a C6-C60 arylene group, or a C3-C60 heteroarylene group;
R 1 to R 8 Respectively, independently of Or R is 1 And R is 2 ；R 3 And R is 4 ；R 5 And R is 6 The method comprises the steps of carrying out a first treatment on the surface of the R is R 7 And R is 8 Can be linked to each other independently to form an aromatic ring-fused or unfused heterocyclic ring;
R 21 to R 24 Independently of one another, C1-C60 alkyl, halogenated C1-C60 alkyl, deuterium, halogen, cyano, C3-C60 cycloalkyl, C1-C60 alkoxy, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylC 1-C60 alkyl, C1-C60 alkyl C6-C60 aryl, C3-C60 heteroaryl, -NR 12 R 13 Nitro or hydroxy;
R 12 r is R 13 Each independently hydrogen, C1-C60 alkyl, C6-C60 aryl, or C3-C60 heteroaryl;
X 1 is NR (NR) 31 O or S;
R 31 is hydrogen, C1-C60 alkyl, C6-C60 aryl or C3-C60 heteroaryl;
the L is 1 To L 4 Arylene and heteroarylene of (2), and R 21 To R 24 The aryl and heteroaryl groups of (C1-C60) can be further substituted with a member selected from the group consisting of C1-C60 alkyl, halo-C1-C60 alkyl, deuterium, halogen, cyano, C3-C60 cycloalkyl, C1-C60 alkoxy, C6-C60 aryl, C6-C60 aryloxy, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl, C3-C60 heteroaryl, -NR 'R', one or more substitutions of nitro and hydroxy;
r 'and R' are each independently hydrogen, C1-C60 alkyl, C6-C60 aryl or C3-C60 heteroaryl;
a is an integer of 0 to 5, and when a is an integer of 2 or more, each R 21 The same or different from each other;
b is an integer of 0 to 7, and when b is an integer of 2 or more, each R 22 The same or different from each other;
c is an integer of 0 to 3, and when c is an integer of 2 or more, each R 23 The same or different from each other;
d is an integer of 0 to 4, and when d is an integer of 2 or more, each R 24 The same or different from each other;
p and q are each independently an integer from 0 to 4, r and s are each independently an integer from 0 to 2, provided that p, q, r and s are not all 0 at the same time;
the heteroarylene and the heteroaryl group include one or more heteroatoms selected from N, O, S and Se.
2. The heterocyclic compound according to claim 1, wherein,
the R is a To R d Each independently is C1-C60 alkyl or C6-C60 aryl;
L 1 to L 4 Each independently is a single bond, a C6-C60 arylene or a C3-C60 heteroarylene group, the L 1 To L 4 The arylene and heteroarylene groups of (a) may be further substituted with one or more groups selected from C1-C60 alkyl, C6-C60 aryl and-NR 'R';
r 'and R' are each independently C6-C60 aryl or C3-C60 heteroaryl;
R 1 To R 8 Are respectively and independentlyOr R is 1 And R is 2 ；R 3 And R is 4 ；R 5 And R is 6 The method comprises the steps of carrying out a first treatment on the surface of the R is R 7 And R is 8 Can be independently linked to each other to form an aromatic ring-fused heterocyclic ring;
R 31 to R 35 Independently of one another, hydrogen, C1-C60 alkyl, deuterium, C6-C60 aryl, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl, C3-C60 heteroaryl or-NR 12 R 13 ；
R 12 R is R 13 Each independently is a C6-C60 aryl or C3-C60 heteroaryl group;
X 1 is O or S;
the R is 31 To R 35 Can be further substituted with one or more selected from the group consisting of C1-C60 alkyl, deuterium, C6-C60 aryl, C6-C60 arylC 1-C60 alkyl, C1-C60 alkylC 6-C60 aryl, and C3-C60 heteroaryl;
p, q, r and s are each independently integers from 0 to 2, provided that 1.ltoreq.p+q+r+s.ltoreq.4 is satisfied.
3. The heterocyclic compound according to claim 2, wherein,
the heterocyclic compound is represented by any one of chemical formula 2 and chemical formula 3 below;
[ chemical formula 2]
[ chemical formula 3]
In the chemical formula 2 and the chemical formula 3,
R a to R d Each independently is a C1-C30 alkyl group;
L 1 l and L 3 Each independently is a single bond, a C6-C30 arylene or a C3-C30 heteroarylene group, the L 1 L and L 3 The arylene and heteroarylene groups of (a) may be further substituted with one or more groups selected from C1-C30 alkyl, C6-C30 aryl and-NR 'R';
R 'and R' are each independently C6-C30 aryl or C3-C30 heteroaryl;
R 1 、R 2 、R 5 r is R 6 Are respectively and independently Or R is 1 And R is 2 R is R 5 And R is 6 Can be independently linked to each other to form an aromatic ring-fused heterocyclic ring;
R 31 to R 35 Independently of one another, hydrogen, C1-C30 alkyl, C6-C30 aryl, C6-C30 arylC 1-C30 alkyl, C1-C30 alkylC 6-C30 aryl, C3-C30 heteroaryl or-NR 12 R 13 ；
R 12 R is R 13 Each independently is a C6-C30 aryl or C3-C30 heteroaryl group;
the R is 31 To R 35 Can be further substituted with one or more selected from the group consisting of C1-C30 alkyl, C6-C30 aryl, C6-C30 arylC 1-C30 alkyl, C1-C30 alkylC 6-C30 aryl, and C3-C30 heteroaryl;
p and r are each independently an integer of 1 or 2.
4. The heterocyclic compound according to claim 3, wherein,
the heterocyclic compound is represented by any one of chemical formula 4 and chemical formula 5 below;
[ chemical formula 4]
[ chemical formula 5]
In the chemical formula 4 and the chemical formula 5,
L 1 l and L 3 Each independently is a single bond, a C6-C20 arylene or a C3-C20 heteroarylene group, the L 1 L and L 3 The arylene and heteroarylene groups of (a) may be further substituted with one or more groups selected from C1-C20 alkyl, C6-C20 aryl and-NR 'R';
r 'and R' are each independently C6-C20 aryl or C3-C20 heteroaryl;
R 1 、R 2 、R 5 R is R 6 Are respectively and independently
R 31 To R 35 Independently of one another, hydrogen, C6-C20-aryl, C3-C20-heteroaryl or-NR 12 R 13 ；
R 12 R is R 13 Each independently is a C6-C20 aryl or C3-C20 heteroaryl group;
the R is 31 To R 35 The aryl and heteroaryl groups of (a) can be further substituted with one or more selected from the group consisting of C1-C20 alkyl, C6-C20 aryl, C6-C20 arylC 1-C20 alkyl, C1-C20 alkylC 6-C20 aryl and C3-C20 heteroaryl.
5. The heterocyclic compound according to claim 2, wherein,
the L is 1 To L 4 Each independently is a single bond or a structure selected from the group consisting of:
in the above-described structure, the first and second heat exchangers,
R L1 、R L2 r is R L3 Each independently hydrogen, C6-C20 aryl or NR 'R';
r 'and R' are each independently C6-C20 aryl or C3-C20 heteroaryl;
z is CR Z1 R Z2 、NR Z3 O or S;
R Z1 r is R Z2 Each independently is C1-C20 alkyl or C6-C20 aryl;
R Z3 is a C6-C20 aryl group.
6. The heterocyclic compound according to claim 4, wherein,
the L is 1 L and L 3 Each independently is a single bond or a C6-C12 arylene group, said L 1 L and L 3 Can be further substituted with one or more selected from the group consisting of C6-C12 aryl and-NR 'R';
r 'and R' are each independently C6-C12 aryl or C3-C12 heteroaryl;
R 1 r is R 5 Are respectively and independently
R 2 R is R 6 Are respectively and independently
R 41 To R 43 R is R 51 To R 54 Are independently of one another hydrogen or C6-C12 aryl; r is R 12 R is R 13 Each independently is a C6-C12 aryl or C3-C12 heteroaryl group.
7. The heterocyclic compound according to claim 1, wherein,
the heterocyclic compound is selected from the following structures:
8. an organic light-emitting element comprising an anode, a cathode, and one or more organic layers provided between the anode and the cathode, one or more of the organic layers comprising the heterocyclic compound selected from any one of claims 1 to 7.
9. The organic light-emitting device according to claim 8, wherein,
the organic layer is at least one layer selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
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| KR10-2021-0152032 | 2021-11-08 | ||
| KR1020210152032A KR102541384B1 (en) | 2020-12-30 | 2021-11-08 | Novel heterocyclic compound and organic light emitting device comprising the same |
| PCT/KR2021/018889 WO2022145806A1 (en) | 2020-12-30 | 2021-12-13 | Novel heterocyclic compound and organic light-emitting device comprising same |
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