CN111699191A - Heterocyclic compound and organic light emitting device including the same - Google Patents
Heterocyclic compound and organic light emitting device including the same Download PDFInfo
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- CN111699191A CN111699191A CN201980012175.5A CN201980012175A CN111699191A CN 111699191 A CN111699191 A CN 111699191A CN 201980012175 A CN201980012175 A CN 201980012175A CN 111699191 A CN111699191 A CN 111699191A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 27
- 239000000126 substance Substances 0.000 claims abstract description 96
- 239000012044 organic layer Substances 0.000 claims abstract description 33
- 239000010410 layer Substances 0.000 claims description 77
- 125000001424 substituent group Chemical group 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000002560 nitrile group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000002019 doping agent Substances 0.000 claims description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 8
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 160
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 84
- 239000007787 solid Substances 0.000 description 81
- -1 dimethylfluorene Chemical class 0.000 description 79
- 125000004432 carbon atom Chemical group C* 0.000 description 75
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 52
- 239000000203 mixture Substances 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 42
- 238000001816 cooling Methods 0.000 description 29
- 239000012047 saturated solution Substances 0.000 description 28
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 26
- 238000000746 purification Methods 0.000 description 26
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 26
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- 230000032258 transport Effects 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
- 229910052786 argon Inorganic materials 0.000 description 13
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 13
- 238000004949 mass spectrometry Methods 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 125000006267 biphenyl group Chemical group 0.000 description 9
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- HVKCZUVMQPUWSX-UHFFFAOYSA-N 1-bromo-2,3-dichlorobenzene Chemical compound ClC1=CC=CC(Br)=C1Cl HVKCZUVMQPUWSX-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 125000003367 polycyclic group Chemical group 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000005264 aryl amine group Chemical group 0.000 description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000010406 cathode material Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SZVQKPOSSXUGKS-UHFFFAOYSA-N 1-bromo-2,3-dichloro-5-iodobenzene Chemical compound ClC1=CC(I)=CC(Br)=C1Cl SZVQKPOSSXUGKS-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- HQUCSZSXCSPONV-UHFFFAOYSA-N 1-bromo-2,3-dichloro-5-phenylbenzene Chemical group ClC1=CC(=CC(Br)=C1Cl)C1=CC=CC=C1 HQUCSZSXCSPONV-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- BUWXUSLQPDDDSD-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-yloxy)butane Chemical compound CCC(C)(C)OC(C)(C)CC BUWXUSLQPDDDSD-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- RPDMJOSIJDCXFJ-UHFFFAOYSA-N 3-bromo-1,2-dichloro-4-iodobenzene Chemical compound BrC1=C(C=CC(=C1Cl)Cl)I RPDMJOSIJDCXFJ-UHFFFAOYSA-N 0.000 description 1
- BRSISBFBCAPIIK-UHFFFAOYSA-N 3-bromo-4,5-dichlorophenol Chemical compound Oc1cc(Cl)c(Cl)c(Br)c1 BRSISBFBCAPIIK-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
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- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
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- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052792 caesium Inorganic materials 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- 230000003993 interaction Effects 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001505 phosphinoxide group Chemical group 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 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 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
Abstract
The present specification provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or 2 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include a heterocyclic compound represented by chemical formula 1.
Description
Technical Field
The present specification claims priority from korean patent application No. 10-2018-0124532, which was filed in 2018, 10, 18 and 18 to the korean patent office, the entire contents of which are incorporated herein by reference.
The present specification relates to a heterocyclic compound and an organic light-emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. In the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
There is a continuing demand for the development of new materials for organic light emitting devices as described above.
U.S. patent application publication No. 2004-0251816
Disclosure of Invention
Technical subject
The present specification provides heterocyclic compounds and organic light emitting devices comprising the same.
Means for solving the problems
The present invention provides a heterocyclic compound represented by the following chemical formula 1.
[ chemical formula 1]
[ chemical formula 2]
In the above chemical formula 1 and chemical formula 2,
R11to R14、R21To R24、R31To R35、R41To R43、R51To R55And R61To R64The same or different from each other, each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or combines with an adjacent substituent to form a substituted or unsubstituted ring,
r is as defined above11To R14、R21To R24、R31To R35、R41To R43And R51To R55Adjacent 2 substituent groups; and the above R11To R14、R21To R24、R31To R35、R41To R43And R51To R55Wherein 1 or more groups among adjacent 2 substituent groups of the substituted or unsubstituted ring formed by bonding adjacent substituents are bonded to the dotted line of chemical formula 2.
In addition, the present specification provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or 2 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include the heterocyclic compound.
Effects of the invention
The heterocyclic compound according to one embodiment of the present specification can be used as a material for an organic layer of an organic light-emitting device, and by using the heterocyclic compound, improvement in efficiency, low driving voltage, and/or improvement in lifetime characteristics can be achieved in the organic light-emitting device.
The heterocyclic compound of the present specification can exhibit high efficiency characteristics in a device by having a small half width in structure.
Drawings
Fig. 1 illustrates an organic light emitting device according to an embodiment of the present specification.
Fig. 2 illustrates an organic light emitting device according to an embodiment of the present description.
Fig. 3 illustrates an organic light emitting device according to an embodiment of the present description.
1: substrate
2: a first electrode
3: organic material layer
4: second electrode
5: luminescent layer
6: hole injection layer
7: hole transport layer-1
8: hole transport layer-2
9: electron transport layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides heterocyclic compounds represented by the above chemical formula 1.
The conventional spiro ring structure has a limit in the characteristic of improving the luminous efficiency by forming a right angle based on a carbon atom positioned at the center or by adjusting the wavelength and suppressing the interaction between molecules using a simple cyclized compound such as dimethylfluorene, and the efficiency and the lifetime of the OLED device can be improved by controlling the electrical characteristics and the luminous characteristics using a new substance including adamantane (adamantane).
In addition, in the case of a core containing boron and nitrogen, by having a small half width, high efficiency characteristics are exhibited in the device.
In the present specification, examples of the substituent are described below, but not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, the "substituent in which 2 or more substituents are bonded" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethylpropyl group, 1-dimethylpropyl group, isohexyl group, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and more preferably a cycloalkyl group having 3 to 20 carbon atoms. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 30. Specifically, the number of carbon atoms is preferably 1 to 20. More specifically, the number of carbon atoms is preferably 1 to 10. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.
In the present specification, the amine group may be represented by the formula of — NRdRe, and Rd and Re may be the same or different from each other, and each independently may be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or the like, but is not limited thereto. The number of carbon atoms of the amine group is not limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methylanthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrenylfluorenylamino group, and an N-biphenylfluorenylamino group.
In the present specification, the silyl group may be represented by the formula of — SiRaRbRc, and the above Ra, Rb and Rc may be the same or different from each other, and each independently may be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or the like. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and more preferably an aryl group having 6 to 30 carbon atoms. The above aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. More specifically, the number of carbon atoms is preferably 6 to 20. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto. In the case where the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30, more specifically, 10 to 20. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a perylene group,
and a fluorenyl group, but is not limited thereto.
When the fluorenyl group is substituted, 2 substituents of the 9 th carbon atom of the fluorenyl group may be bonded to each other to form a spiro structure such as a 9, 9-dimethylfluorenyl group, a 9, 9-diphenylfluorenyl group, or the like, but the invention is not limited thereto.
In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest in steric structure to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as groups "adjacent" to each other.
In the present specification, in the substituted or unsubstituted ring formed by bonding to each other, "ring" means a hydrocarbon ring or a heterocyclic ring.
The hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and may be selected from the cycloalkyl groups and the aryl groups described above, in addition to the 2-valent group described above.
In the present specification, the aromatic hydrocarbon ring may have a valence of 2, and the above description about the aryl group may be applied.
The heterocyclic group may be substituted with a 2-valent heterocyclic group as described below.
In the present specification, as examples of the arylamine group, there are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more of the above-mentioned aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group.
In the present specification, the heterocyclic group contains 1 or more heteroatoms other than carbon atoms, specifically, the heteroatoms may contain 1 or more atoms selected from O, N, Se, SO2And S, etc. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of the above-mentioned heteroaryl group include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, a thienyl group,
Azolyl group,
Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Examples of the heterocyclic group include, but are not limited to, an azole group, a thiadiazole group, a phenothiazine group, and a dibenzofuran group.
According to an embodiment of the present disclosure, R is11To R14、R21To R24、R31To R35、R41To R43、R51To R55And R61To R64The above R's are the same as or different from each other, and each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or combine with an adjacent substituent to form a substituted or unsubstituted ring11To R14、R21To R24、R31To R35、R41To R43And R51To R55Adjacent 2 substituent groups; and the above R11To R14、R21To R24、R31To R35、R41To R43And R51To R55Wherein 1 or more groups among adjacent 2 substituent groups of the substituted or unsubstituted ring formed by bonding adjacent substituents are bonded to the dotted line of chemical formula 2.
The above-mentioned "R11To R14、R21To R24、R31To R35、R41To R43And R51To R55The adjacent 2 substituent groups "means 2 substituents substituted at the ortho position (ortho) in the above chemical formula 1. Specifically, in the above chemical formula 1, R11And R12、R12And R13、R13And R14、R21And R22、R22And R23、R23And R24、R31And R32、R32And R33、R33And R34、R34And R35、R41And R42、R42And R43、R51And R52、R52And R53、R53And R54And R54And R55Each of the adjacent 2 substituents corresponds to one group. Further, the above-mentioned "R" is11To R14、R21To R24、R31To R35、R41To R43And R51To R55The adjacent 2 substituent groups of the substituted or unsubstituted ring formed by combining the adjacent substituents in (1) means that R of chemical formula 1 is as follows23And R24When they are bonded to each other to form a benzene ring, the following R25And R26、R26And R27And R27And R28Each of the adjacent 2 substituents corresponds to one group.
According to an embodiment of the present disclosure, R is11To R14、R21To R24、R31To R35、R41To R43And R51To R55Adjacent 2 substituent groups; and the above R11To R14、R21To R24、R31To R35、R41To R43And R51To R55Wherein 1 to 4 groups among adjacent 2 substituent groups of the substituted or unsubstituted ring formed by combining adjacent substituents are combined with the dotted line of the above chemical formula 2.
According to an embodiment of the present disclosure, R is11To R14、R21To R24、R31To R35、R41To R43And R51To R55Adjacent 2 substituent groups; and the above R11To R14、R21To R24、R31To R35、R41To R43And R51To R55Wherein 1 or more groups among adjacent 2 substituent groups of the substituted or unsubstituted ring formed by bonding adjacent substituents are bonded to the dotted line of chemical formula 2, wherein R is as defined above11To R14、R21To R24、R31To R35、R41To R43And R51To R55Wherein the substituent not bound to chemical formula 2 and R61To R64The same or different from each other, each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or combines with an adjacent substituent to form a substituted or unsubstituted ring.
In one embodiment of the present specification, R is11To R14、R21To R24、R31To R35、R41To R43And R51To R55Wherein the substituent not bound to chemical formula 2 and R61To R64The same as or different from each other, each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group having 1 to 60 carbon atoms, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or is combined with adjacent substituents to each other to form a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms. The above "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium, a nitrile group, a halogen group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a silyl group having 1 to 30 carbon atoms, an amino group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, R is11To R14、R21To R24、R31To R35、R41To R43And R51To R55Wherein the substituent not bound to chemical formula 2 and R61To R64The same or different from each other, each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted ethoxy group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted dibenzofuranylanilino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl anilino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenylA substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted pyridyl group, or an aromatic or aliphatic hydrocarbon ring having 3 to 30 carbon atoms which is substituted or unsubstituted and is bonded to an adjacent substituent; or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms and containing 1 or more of N, O and S as a hetero atom. The above-mentioned "substituted or unsubstituted" means substituted or unsubstituted with one or more groups selected from deuterium, a nitrile group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted ethoxy group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted dibenzofuranylanilino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenyl group, substituted or unsubstituted dibenzothienyl and substituted or unsubstituted pyridyl are substituted or unsubstituted by 1 or more substituents bonded together.
In one embodiment of the present specification, the above chemical formula 1 is represented by one of the following chemical formulas 1-1 to 1-7.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1 to 4]
[ chemical formulas 1 to 5]
[ chemical formulas 1 to 6]
[ chemical formulas 1 to 7]
In the above chemical formulas 1-1 to 1-7,
R11to R14、R21To R24、R31To R35、R41To R43、R51To R55And R61To R64As defined in chemical formulas 1 and 2,
R71to R74、R81To R84、R91To R94And Ra to Re are the same as or different from each other, and each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent substituent to form a substituted or unsubstituted ring,
a and c are each an integer of 0 to 3,
b and f are each 0 or 1,
d and e are each an integer of 0 to 2,
a. and c to e are each 2 or more, the substituents in parentheses may be the same or different from each other.
According to an embodiment of the present disclosure, R is71To R74、R81To R84、R91To R94And Ra to Re are the same as or different from each other, and each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group having 1 to 60 carbon atoms, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or combines with adjacent substituents to form a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms. The above "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium, a nitrile group, a halogen group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a silyl group having 1 to 30 carbon atoms, an amino group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, R is71To R74、R81To R84、R91To R94And Ra to Re are the same or different from each other and each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted ethoxy group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted dibenzofuranylanilino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted ethoxy group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamino group, a substituted orA substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted aromatic or aliphatic hydrocarbon ring having 3 to 30 carbon atoms which is bonded to an adjacent substituent; or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms and containing 1 or more of N, O and S as a hetero atom. The above-mentioned "substituted or unsubstituted" means substituted or unsubstituted with one or more groups selected from deuterium, a nitrile group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted ethoxy group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted dibenzofuranylanilino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenyl group, substituted or unsubstituted dibenzothienyl and substituted or unsubstituted pyridyl are substituted or unsubstituted by 1 or more substituents bonded together.
In one embodiment of the present specification, the above chemical formula 1 is represented by one of the following chemical formulas 2-1 to 2-5.
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
[ chemical formulas 2-4]
[ chemical formulas 2 to 5]
In the above chemical formulas 2-1 to 2-5,
R11to R14、R21To R24、R31To R35、R41To R43And R51To R55As defined in chemical formulas 1 and 2,
X1and X2Equal to or different from each other, each independently O, S or NR,
R、R101to R111And R201To R228The same or different from each other, each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group,
n1 to n9 are each an integer of 0 to 2,
n10 and n11 are each an integer of 0 to 4,
when n1 to n11 are each 2 or more, the substituents in parentheses may be the same or different from each other.
According to one embodiment of the present disclosure, the R, R is101To R111And R201To R228The same or different from each other, each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbonA cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group having 1 to 60 carbon atoms, a substituted or unsubstituted amino group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or a substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms is formed by bonding adjacent substituents to each other. The above "substituted or unsubstituted" means substituted or unsubstituted with 1 or more substituents selected from deuterium, a nitrile group, a halogen group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a silyl group having 1 to 30 carbon atoms, an amino group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms.
In one embodiment of the present specification, the R, R is101To R111And R201To R228The same or different from each other, each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted ethoxy group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted dibenzofuranylanilino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenylthio group, A substituted or unsubstituted dibenzothienyl group or a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted aromatic or aliphatic hydrocarbon ring having 3 to 30 carbon atoms, which is bonded to an adjacent substituent; or a substituted or unsubstituted C2-30 compound containing N, O and 1 or more of S as hetero atomsThe heterocyclic ring of (1). The above-mentioned "substituted or unsubstituted" means substituted or unsubstituted with one or more groups selected from deuterium, a nitrile group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted cyclopropyl group, a substituted or unsubstituted cyclobutyl group, a substituted or unsubstituted cyclopentyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted ethoxy group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted dibenzofuranylanilino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenyl group, substituted or unsubstituted dibenzothienyl and substituted or unsubstituted pyridyl are substituted or unsubstituted by 1 or more substituents bonded together.
In one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.
In the above specific examples, D is deuterium, Me is methyl, and Ph is phenyl.
In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.
In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the another member but also a case where the other member exists between the two members.
The organic light emitting device of the present invention comprises: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or 2 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers may include the heterocyclic compound.
For example, the structure of the organic light emitting device of the present invention may have the structure shown in fig. 1 to 3, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.
The organic light emitting device is illustrated in fig. 1, but is not limited thereto.
Fig. 2 illustrates a structure of an organic light emitting device in which a first electrode 2, a light emitting layer 5, and a second electrode 4 are sequentially stacked on a substrate 1.
The organic light emitting device illustrated in fig. 2 is not limited thereto, and an additional organic layer may be further included between the first electrode 2 and the light emitting layer 5 and between the light emitting layer 5 and the second electrode 4.
Fig. 3 illustrates a structure of an organic light emitting device in which a first electrode 2, a hole injection layer 6, a hole transport layer-1 (7), a hole transport layer-2 (8), a light emitting layer 5, an electron transport layer 9, and a second electrode 4 are sequentially stacked on a substrate 1.
In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound of chemical formula 1.
The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer may include a host and a dopant at a mass ratio of 99.9:0.1 to 90: 10.
The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer may include a host and a dopant in a mass ratio of 99.5:0.5 to 95: 5.
In one embodiment of the present invention, the organic layer includes a light emitting layer including the heterocyclic compound of chemical formula 1 as a dopant.
In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound of chemical formula 1 as a dopant of the light emitting layer.
In one embodiment of the present invention, the organic layer includes 1 or more of a hole injection layer, a hole transport layer, and a hole injection and transport layer, and 1 or more of the hole injection layer, the hole transport layer, and the hole injection and transport layer may include the heterocyclic compound of chemical formula 1.
In one embodiment of the present invention, the organic layer includes 1 or more of an electron injection layer, an electron transport layer, and an electron injection and transport layer, and the 1 or more of the electron injection layer, the electron transport layer, and the electron injection and transport layer may include the heterocyclic compound of chemical formula 1.
In one embodiment of the present invention, the organic layer includes 1 or more of an electron blocking layer and a hole blocking layer, and the electron blocking layer and/or the hole blocking layer may include the heterocyclic compound of chemical formula 1.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that 1 or more of the organic layers are formed using the heterocyclic compound.
The present specification also provides a method for manufacturing an organic light-emitting device using the heterocyclic compound.
For example, the organic light emitting device according to the present invention can be manufactured as follows: the organic el device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and the like, and an organic layer including the compound of the above chemical formula 1 on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to these methods, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
As the substance capable of injecting holes from the anode at a low voltage, the hole-injecting substance preferably has a HOMO (highest occupied molecular orbital) between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrine), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole-transporting substance is a substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) Carbazole-based compounds, dimerized styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; a polyfluorene; rubrene, etc., but not limited thereto.
As the dopant material, there are an aromatic compound, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic compound is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, perylene, and the like having an arylamino group,
And diindenopyrene, and the like, and the styrylamine compound is a compound substituted with at least 1 arylvinyl group in a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. Furthermore, as metal complexesThere are iridium complexes, platinum complexes, and the like, but the present invention is not limited thereto.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can inject electrons well from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathodes are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The hole-blocking layer is a layer that prevents holes from reaching the cathode and can be formed under the same conditions as those of the hole-injecting layer. Specifically, there are
An oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
Modes for carrying out the invention
Hereinafter, in order to specifically explain the present specification, the details are explained by referring to examples. However, the embodiments described herein may be modified into various forms, and the scope of the present description is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.
< production example >
Production example 1.
1)
The reaction mixture was charged with 1-bromo-2, 3-dichlorobenzene (22.6g), intermediate A-1(16.9g), Pd (PtBu)3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate A-2(25.5g) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 315.
2)
The intermediate A-2(20.0g), intermediate A-3(24.0g), Pd (PtBu) were charged3)2A flask of (0.33g), NaOtBu (12.23g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate a-4(13.35 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 378.
3)
To a flask containing intermediate A-4(9.76g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 1(3.2 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z629 was confirmed.
Production example 2.
1)
The reaction mixture was charged with 1-bromo-2, 3-dichlorobenzene (22.6g), intermediate B-1(19.7g), Pd (PtBu)3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirredFor 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate B-2(24.0g) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 343.
2)
The intermediate B-2(15.0g), the intermediate B-3(20.7g) and Pd (PtBu) were charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate B-4(17.1 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak 780.
3)
To a flask containing intermediate B-4(11.6g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, and the mixture was stirred at room temperature for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 2(3.8 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z753 was confirmed.
Production example 3.
1)
The reaction mixture was charged with 1-bromo-2, 3-dichlorobenzene (22.6g), intermediate C-1(19.7g), Pd (PtBu)3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate C-2(24.0g) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 343.
2)
The intermediate C-2(15.0g), intermediate C-3(17.2g), Pd (PtBu) were charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate C-4(14.2 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 698.
3)
To a flask containing intermediate C-4(10.4g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 3(3.5 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z671 was confirmed.
Production example 4.
1)
The reaction mixture was charged with 1-bromo-2, 3-dichlorobenzene (22.6g), intermediate D-1(45.5g), Pd (PtBu)3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate D-2(28.5g) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 600.
2)
The intermediate D-2(26.3g), the intermediate D-3(19.9g) and Pd (PtBu) were charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and after separation, the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate D-4(18.1 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 1018.
3)
To a flask containing intermediate D-4(15.2g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to the solution to obtain compound 4(5.0 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z992 was confirmed.
Production example 5.
1)
The reaction mixture was charged with 1-bromo-2, 3-dichlorobenzene (22.6g), intermediate E-1(48.3g), Pd (PtBu)3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate E-2(28.0g) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 628.
2)
The intermediate E-2(27.5g), intermediate E-3(20.1g), Pd (PtBu) were charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Chromatography on silica gel column (developing solution: hexane/ethyl acetate)Purification of the ester 50%/50% (v/v)) gave intermediate E-4(23.0 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 1051.
3)
To a flask containing intermediate E-4(15.7g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 5(8.8 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z1025 was confirmed.
Production example 6.
1)
The reaction mixture was charged with 1-bromo-2, 3-dichlorobenzene (22.6g), intermediate F-1(120.0g), Pd (PtBu)3)2A flask of (1.02g), NaOtBu (38.4g) and toluene (800ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate F-2(50.1g) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]1309 peak.
2)
To a flask containing intermediate F-2(19.5g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 6(9.8 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z1282 was confirmed.
Production example 7.
1)
The reaction mixture was charged with 1-bromo-2, 3-dichlorobenzene (22.6G), intermediate G-1(16.9G), Pd (PtBu)3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate G-2(25.5G) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 315.
2)
The intermediate G-2(13.8G), intermediate G-3(40.0G), Pd (PtBu) were charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Column chromatography over silica gel (developing solution: hexane/ethyl acetate 50%/50%(volume ratio)) was purified, thereby obtaining intermediate G-4 (26.6G). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 1191.
3)
To a flask containing intermediate G-4(17.7G) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 7(6.6 g). As a result of mass spectrometry of the obtained solid, a peak at 1164 was confirmed.
Production example 8.
1)
The reaction mixture containing 3-bromo-4, 5-dichloro-1, 1' -biphenyl (30.2g), intermediate H-1(47.0g), Pd (PtBu)3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane) to obtain intermediate H-2(55.9 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak 691.
2)
The intermediate H-2(30.3g), intermediate H-3(9.6g), Pd (PtBu) were charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate H-4(23.7 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 874.
3)
To a flask containing intermediate H-4(13.0g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 8(8.7 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z847 was confirmed.
Production example 9.
1)
The reaction mixture was charged with 1-bromo-2, 3-dichloro-5-toluene (24.0g), intermediate I-1(37.8g), Pd (PtBu)3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. By recrystallization of (methyl tert-butyl)Ether/hexane) to give intermediate I-2(40.2 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak 537.
2)
The intermediate I-2(23.5g), intermediate I-3(16.5g), Pd (PtBu) were charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate I-4(19.3 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 878.
3)
To a flask containing intermediate I-4(13.1g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 9(6.9 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z851 was confirmed.
Production example 10.
1)
The mixture was charged with 1-bromo-2, 3-dichloro-5-iodobenzene (70.4g), intermediate J-1(54.4g), Pd (PPh)3)2(0.51g)、K2CO3A flask of (55.2g) and 200mL of tetrahydrofuran (1000mL) as water was heated under reflux and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and tetrahydrofuran, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (ethyl acetate/hexane) to give intermediate J-2(73.3 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]The peak at 453.
2)
Will contain intermediate J-2(67.8g), CH3SO2A flask of OH (96mL) and toluene (600mL) was stirred for 5 hours. The reaction solution was cooled to room temperature, and after the reaction was poured into water, the resultant solid was filtered, and the resultant solid was purified with chloroform and ethanol, thereby obtaining intermediate J-3(59.9 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 435.
3)
The intermediate J-3(43.4g), intermediate J-4(16.9g), Pd (PtBu) were charged3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), thereby obtaining intermediate J-5(40.8 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]The peak at 523.
4)
The intermediate J-5(22.9g), intermediate J-6(8.6g) and Pd (PtBu) are charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate J-7(19.4 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak 684.
5)
To a flask containing intermediate J-7(10.2g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 10(6.5 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z657 was confirmed.
Production example 11.
1)
The mixture was charged with 1-bromo-2, 3-dichloro-5-iodobenzene (70.4g), intermediate K-1(58.0g), Pd (PPh)3)2(0.51g)、K2CO3A flask of (55.2g) and 200mL of tetrahydrofuran (1000mL) as water was heated under reflux and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. N)H4Cl) and tetrahydrofuran, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (ethyl acetate/hexane) to give intermediate K-2(73.3 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 471.
2)
The intermediate K-2(70.5g) and CH are charged3SO2A flask of OH (96mL) and toluene (600mL) was stirred for 5 hours. The reaction solution was cooled to room temperature, and after the reaction mixture was poured into water, the resultant solid was filtered, and the resultant solid was purified with chloroform and ethanol, thereby obtaining intermediate K-3(61.0 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]The peak at 453.
3)
The intermediate K-3(45.2g), the intermediate K-4(52.6g) and Pd (PtBu) are charged3)2A flask of (1.02g), NaOtBu (38.4g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate K-5(40.5g) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 862.
4)
To a flask containing intermediate K-5(12.8g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 11(4.8 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z835 was confirmed.
Production example 12.
1)
The mixture was charged with 2-bromo-3, 4-dichloro-1-iodobenzene (70.4g), intermediate L-1(54.4g), Pd (PPh)3)2(0.51g)、K2CO3A flask of (55.2g) and 200mL of tetrahydrofuran (1000mL) as water was heated under reflux and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and tetrahydrofuran, and the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (ethyl acetate/hexane) to obtain intermediate L-2(68.1 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]The peak at 453.
2)
Will contain intermediate L-2(67.8g), CH3SO2A flask of OH (96mL) and toluene (600mL) was stirred for 5 hours. The reaction solution was cooled to room temperature, and after the reaction mixture was poured into water, the resultant solid was filtered, and the resultant solid was purified with chloroform and ethanol, thereby obtaining intermediate L-3(60.1 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 435.
3)
The intermediate L-3(43.4g), intermediate L-4(40.6g), Pd (PtBu) were charged3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate L-5(37.9g) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 759.
4)
The intermediate L-5(33.2g), intermediate L-6(17.8g), Pd (PtBu) were charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate L-7(18.8 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak 1129.
5)
To a flask containing intermediate L-7(16.8g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to obtain compound 12(6.9 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z1102 was confirmed.
Production example 13.
1)
The mixture containing 3-bromo-4, 5-dichlorophenol (24.2g), intermediate M-1(16.9g) and Pd (PtBu)3)2A flask of (0.51g), NaOtBu (19.2g) and toluene (400ml) was heated and stirred at 110 ℃ for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by recrystallization (methyl t-butyl ether/hexane), whereby intermediate M-2(28.1g) was obtained. Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 331.
2)
The intermediate M-2(14.5g), intermediate M-3(16.5g) and Pd (PtBu) are charged3)2A flask of (0.22g), NaOtBu (8.42g) and toluene (400ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain intermediate M-4(17.9 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 672.
3)
To a flask containing intermediate M-4(10.0g) and tert-butylbenzene (160ml) was added 1.7M t-butyllithium pentane solution (9.2ml) under argon at 0 ℃. After the end of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 4 hours, and the pentane was distilled off. Cooled to-40 ℃, boron tribromide (1.6ml) was added, the temperature was raised to room temperature, and stirring was carried out for 4 hours. Then, the mixture was cooled to 0 ℃ again, N-diisopropylethylamine (6.6ml) was added thereto, and the mixture was stirred at room temperature and then at 80 ℃ for 4 hours. The reaction solution was cooled to room temperature, water and ethyl acetate were added to separate the reaction solution, and then the solvent was distilled off under reduced pressure. Acetonitrile was added to the solution to obtain intermediate M-5(4.8 g). As a result of mass spectrometry of the obtained solid, a peak at M/Z645 was confirmed.
4)
Intermediate M-5(4.1g), nonafluorobutane-1-sulfonylfluoride (2.2g) and potassium carbonate (1.5g) were dissolved in acetonitrile (40ml), heated to 50 ℃ and then stirred for 4 hours. After cooling to normal temperature, distilled water was poured in to remove potassium carbonate, thereby obtaining intermediate M-6(5.5 g).
5)
The intermediate M-6(13.8g), intermediate M-7(6.4g) and Pd (PtBu) are charged3)2A flask of (0.10g), NaOtBu (3.0g) and toluene (100ml) was heated at 110 ℃ and stirred for 30 minutes. Cooling the reaction solution to room temperature, and adding NH4Saturated solution of Cl (sat. aq. NH)4Cl) and toluene, and then the solvent was distilled off under reduced pressure. Purification was performed by silica gel column chromatography (developing solution: hexane/ethyl acetate 50%/50% (volume ratio)) to obtain compound 13(11.2 g). Mass spectrometric determination of the solid obtained confirms that the solid is at [ M + H +]Peak at 1055.
< Experimental example >
Example 1.
Indium Tin Oxide (ITO) and a process for producing the same
Glass coated with a thin filmThe substrate was washed with ultrasonic waves by placing the substrate in distilled water containing a detergent dissolved therein. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared, HAT was added to
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, as a first hole transport layer, the following compound HT-A was vacuum-deposited
Next, as a second hole transport layer, the following compound HT-B was vapor-deposited
Formed by vacuum vapor deposition of BH-A as a host and Compound 1 as a dopant in a weight ratio of 95:5
A thick light emitting layer.
N mutext, as a layer for simultaneously performing electron injection and electron transport, the following compound ET-A and the following compound Liq were vapor-deposited at a ratio of 1:1
On the above layer where electron injection and electron transport are simultaneously performed, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the cathode is formed by vapor deposition to produce an organic light-emitting device.
In the above process, the evaporation speed of the organic material is maintained
Sec, maintenance of lithium fluoride at the cathode
Vapor deposition speed/sec, aluminum maintenance
A vapor deposition rate of sec, and a degree of vacuum of 1 × 10 was maintained during vapor deposition-7To 5 × 10-8And supporting to thereby fabricate an organic light emitting device.
Examples 2 to 14
An organic light-emitting device was produced in the same manner as in example 1, except that in example 1, the host and dopant compounds described in table 1 below were used as the light-emitting layer material.
Comparative examples 1 to 4
An organic light-emitting device was produced in the same manner as in example 1, except that in example 1, the host and dopant compounds described in table 1 below were used as the light-emitting layer material.
Examples 15 to 19 and comparative example 5
An organic light-emitting device was produced in the same manner as in example 1, except that in example 1, the host and dopant compounds described in table 1 below were used as the light-emitting layer material. Specifically, for the bodies, the first body and the second body were used in a weight ratio of 1:1 in place of BH-a of example 1.
The organic light emitting devices fabricated according to the above examples 1 to 19 and comparative examples 1 to 5 were measured at 10mA/cm2The driving voltage and efficiency at the current density of (2) were measured at 20mA/cm2The time required for the initial luminance to be 97% at the current density of (D) (T97). The results are shown in table 1 below.
[ Table 1]
As shown in table 1 above, it can be confirmed that the devices of examples 1 to 19 using the compound having the structure of chemical formula 1 have characteristics of low voltage, high efficiency, and long life as compared with the devices of comparative examples 1 to 5.
Claims (8)
1. A heterocyclic compound represented by the following chemical formula 1:
chemical formula 1
Chemical formula 2
In the chemical formulas 1 and 2,
R11to R14、R21To R24、R31To R35、R41To R43、R51To R55And R61To R64The same or different from each other, each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent substituent to form a substituted or unsubstituted ring,
the R is11To R14、R21To R24、R31To R35、R41To R43And R51To R55Adjacent 2 substituent groups; and said R11To R14、R21To R24、R31To R35、R41To R43And R51To R55Wherein 1 or more groups among adjacent 2 substituent groups of the substituted or unsubstituted ring formed by combining adjacent substituents are combined with the dotted line of chemical formula 2.
2. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-7:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1 to 3
Chemical formulas 1 to 4
Chemical formulas 1 to 5
Chemical formulas 1 to 6
Chemical formulas 1 to 7
In the chemical formulas 1-1 to 1-7,
R11to R14、R21To R24、R31To R35、R41To R43、R51To R55And R61To R64As defined in chemical formulas 1 and 2,
R71to R74、R81To R84、R91To R94And Ra to Re are the same as or different from each other, and each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combines with an adjacent substituent to form a substituted or unsubstituted ring,
a and c are each an integer of 0 to 3,
b and f are each 0 or 1,
d and e are each an integer of 0 to 2,
a. and c to e are each 2 or more, the substituents in parentheses may be the same or different from each other.
3. The heterocyclic compound according to claim 1, wherein R is11To R14、R21To R24、R31To R35、R41To R43And R51To R55Adjacent 2 substituent groups; and said R11To R14、R21To R24、R31To R35、R41To R43And R51To R55Wherein 1 to 4 groups among adjacent 2 substituent groups of the substituted or unsubstituted ring formed by combining adjacent substituents are combined with the dotted line of chemical formula 2.
4. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 2-1 to 2-5:
chemical formula 2-1
Chemical formula 2-2
Chemical formula 2-3
Chemical formula 2-4
Chemical formula 2-5
In the chemical formulas 2-1 to 2-5,
R11to R14、R21To R24、R31To R35、R41To R43And R51To R55As defined in the chemical formulas 1 and 2,
X1and X2Equal to or different from each other, each independently O, S or NR,
R、R101to R111And R201To R228The same or different from each other, each independently is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group,
n1 to n9 are each an integer of 0 to 2,
n10 and n11 are each an integer of 0 to 4,
when n1 to n11 are each 2 or more, the substituents in parentheses may be the same or different from each other.
5. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is any one selected from the following compounds:
6. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or 2 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the heterocyclic compound according to any one of claims 1 to 5.
7. The organic light-emitting device according to claim 6, wherein the organic layer comprises a light-emitting layer containing a host and a dopant at a mass ratio of 99.9:0.1 to 80: 20.
8. The organic light-emitting device according to claim 6, wherein the organic layer comprises a light-emitting layer containing the heterocyclic compound.
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2020080872A1 (en) | 2020-04-23 |
| CN111699191B (en) | 2023-11-07 |
| KR20200043923A (en) | 2020-04-28 |
| KR102225908B1 (en) | 2021-03-10 |
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