TW201249960A - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents
Novel compounds for organic electronic material and organic electroluminescent device using the same Download PDFInfo
- Publication number
- TW201249960A TW201249960A TW101112951A TW101112951A TW201249960A TW 201249960 A TW201249960 A TW 201249960A TW 101112951 A TW101112951 A TW 101112951A TW 101112951 A TW101112951 A TW 101112951A TW 201249960 A TW201249960 A TW 201249960A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- substituted
- compound
- unsubstituted
- aryl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 157
- 239000012776 electronic material Substances 0.000 title description 5
- 125000003118 aryl group Chemical group 0.000 claims description 52
- -1 extension Chemical group 0.000 claims description 29
- 230000005684 electric field Effects 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 8
- 229910052796 boron Inorganic materials 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 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 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- PGBVLOMZZHYJFP-UHFFFAOYSA-N 3-methyldithietane Chemical group CC1CSS1 PGBVLOMZZHYJFP-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 210000000416 exudates and transudate Anatomy 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims 1
- 125000006836 terphenylene group Chemical group 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
- 239000011541 reaction mixture Substances 0.000 description 76
- 238000002360 preparation method Methods 0.000 description 53
- 239000000203 mixture Substances 0.000 description 52
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000010410 layer Substances 0.000 description 37
- 239000012044 organic layer Substances 0.000 description 36
- 239000000463 material Substances 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 32
- 239000007787 solid Substances 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000008213 purified water Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 5
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 5
- 229910052805 deuterium Inorganic materials 0.000 description 5
- 230000005484 gravity Effects 0.000 description 5
- 238000000227 grinding Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000001665 trituration Methods 0.000 description 5
- PSRYSSKJJRCOJV-UHFFFAOYSA-N 4H-1,3,2,4-benzodioxadiazine Chemical compound N1ONOC2=CC=CC=C12 PSRYSSKJJRCOJV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 238000004299 exfoliation Methods 0.000 description 2
- ATBKVKDEMSGMTQ-UHFFFAOYSA-N hydrazine triphenylphosphane Chemical compound NN.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 ATBKVKDEMSGMTQ-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- YKISYRCBRZDTLK-UHFFFAOYSA-N 2-phenylpyridine;pyridine Chemical compound C1=CC=NC=C1.C1=CC=CC=C1C1=CC=CC=N1 YKISYRCBRZDTLK-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- WHGMHGPIJZTKTI-UHFFFAOYSA-N 3h-1,2-benzodithiole Chemical compound C1=CC=C2CSSC2=C1 WHGMHGPIJZTKTI-UHFFFAOYSA-N 0.000 description 1
- ONOZPOGRUBSLQA-UHFFFAOYSA-N 4-(2-methylbutan-2-yl)phenol;2-phenylphenol Chemical group CCC(C)(C)C1=CC=C(O)C=C1.OC1=CC=CC=C1C1=CC=CC=C1 ONOZPOGRUBSLQA-UHFFFAOYSA-N 0.000 description 1
- UCZQXJKDCHCTAI-UHFFFAOYSA-N 4h-1,3-dioxine Chemical compound C1OCC=CO1 UCZQXJKDCHCTAI-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- UJASZVHDIGKVOK-UHFFFAOYSA-N 8-hydroxy-1h-quinoline-2-thione Chemical compound C1=CC(=S)NC2=C1C=CC=C2O UJASZVHDIGKVOK-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- OYGSACNMDOXCMN-UHFFFAOYSA-N C=1OC=C2OC=C3C=CC=C4C=CC1C2=C34 Chemical compound C=1OC=C2OC=C3C=CC=C4C=CC1C2=C34 OYGSACNMDOXCMN-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101710129170 Extensin Proteins 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000005584 chrysenylene group Chemical group 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 235000019529 tetraterpenoid Nutrition 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
- Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Manufacturing & Machinery (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
201249960 六、發明說明： 【發明所屬之技術領域】 本發明係關於一種用於右撬带 m用於有機電子材料之新穎化合物 及使用該化合物之有機電場發光裝置。 【先前技術】 電場發光（electr〇luminescent，EL)裝置係自發光裝 置，相較其他㈣之顯示器裝置，其在提供更寬視角、更 高對比度及更快響應時間方面具有優勢。#由使用芳族二 胺小分子以及㈣合物作為形成發光層之材料，Eastman Kodak第一個研發了有機EL裝置[Αρρ1· ρ_.匕咐.51， 913， 1987]。 用以確定有機EL裝置之發光效率的最重要因素為發光 材料。迄今為止，螢光材料業經廣泛用作發光材料。然而， 以電場發光機制之觀點看來，理論上磷光材料係顯示比螢光 材料咼4倍之發光效率。因此，近年業經研究碟光材料。銀 (ΠI)錯合物業經廣泛認知是鱗光材料，包括雙（(2’ 一笨 并噻吩基比啶-N，C3,）銥（乙醯丙酮）（（acac)Ir(btp)2)、 銮（2-苯基°比啶）銥（Ir(ppy)3)以及雙（4, 6-二氟苯基。比啶-N，C2)Dtt咬曱酸銀（Firpic)係分別作為紅光、綠光及藍光材 料。目前，4, 4’-N，Ν’-二咔唑-聯苯（CBP)係最廣為人知的 用於磷光物質之主體材料。再者，日本先鋒公司（Pi〇neer) 等研發了一種高效能有機EL裝置，該裝置採用浴銅靈 (bathocuproine，BCP)以及業經作為電洞阻擋層材料而使 用之雙（2-曱基-8-羥基喹啉）（4-苯基酚）鋁（in)(BAlq)作 95566 3 201249960 為主體材料。 儘管這些磷主體材料提供良好之發光特性，他們具有 下列劣勢：（1)由於他們的玻璃轉化溫度低且熱安定性極 差，他們可能於真空高溫沉積製程過程中出現降解。（2)有 機EL裝置之功率效率係藉由[(7Γ/電壓）x電流效率]計算， 且功率效率與電壓成反比，因此，爲了降低功率消耗，功 率效率應盡可能高。雖然包含磷光材料之有機EL裝置提供 比包含螢光材料者更高之電流效率（燭光（cd)/安培（A))， 當使用傳統材料如BAlq或CBP作為磷光主體材料時，與使 用螢光材料之有機EL裝置相比，更需要足夠高之驅動電 壓。因此，於功率效率（流明（lm)/瓦（W))方面無任何優勢 可言。（3)再者，有機EL裝置之使用壽命短，且仍需提升 其發光效率。 第W0 2006/049013公開號國際專利案揭露了具有經 稠合之雙環基作為骨架結構的用於有機電場發光材料之化 合物。然而，其並未揭露具有含氮之稠合雙環基、於3-位 及9-位處各皆經祠合有芳族環之環烷基或雜環烷基取代 之咔唑基、以及稠合有芳族環之雜環烷基或環烷基的化合 物。 【發明内容】 待解決之問題 本發明之目標係提供一種用於有機電子材料之化合 物，其係具有優異之結構，該結構賦予裝置以高發光效率 及長使用壽命且具有適宜之色座標；以及一種使用該化合 95566 4 201249960 物且具有高效率及長壽命之有機電場發光裝置。 解決問題之方法 本發明之發明人發現’可藉由下式1表示之化合物達 成上述目標：201249960 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a novel compound for a right enthalpy tape m for an organic electronic material and an organic electric field illuminating device using the same. [Prior Art] An electric field illuminating (EL) device is a self-illuminating device which has advantages in providing a wider viewing angle, higher contrast, and faster response time than other (4) display devices. # From the use of aromatic diamine small molecules and (tetra) compounds as materials for forming the light-emitting layer, Eastman Kodak first developed an organic EL device [Αρρ1· ρ_.匕咐.51, 913, 1987]. The most important factor for determining the luminous efficiency of the organic EL device is the luminescent material. Fluorescent materials have been widely used as luminescent materials to date. However, from the viewpoint of the electric field luminescence mechanism, the phosphorescent material is theoretically shown to have a luminous efficiency four times that of the fluorescent material. Therefore, in recent years, research has been conducted on disc materials. The silver (ΠI) mismatched property is widely recognized as a squama material, including bis((2'-phenyl)-thiophene-N,C3,) 醯(acetamidineacetone)((acac)Ir(btp)2) , 銮 (2-phenylpyridinium pyridine) 铱 (Ir (ppy) 3) and bis (4, 6-difluorophenyl. pyridine-N, C2) Dtt bite silver (Firpic) system as red Light, green and blue light materials. Currently, 4, 4'-N, Ν'-dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Furthermore, Japan Pioneer Company (Pi〇) Neer) et al. developed a high-performance organic EL device using bathocuproine (BCP) and bis(2-mercapto-8-hydroxyquinoline) (4-) used as a barrier material for holes. Phenylphenol) aluminum (in) (BAlq) is used as the host material for 95566 3 201249960. Although these phosphorous host materials provide good luminescent properties, they have the following disadvantages: (1) due to their low glass transition temperature and thermal stability Poor, they may degrade during the vacuum high temperature deposition process. (2) The power efficiency of the organic EL device is measured by [(7Γ/voltage) x current efficiency] And power efficiency is inversely proportional to voltage, therefore, in order to reduce power consumption, power efficiency should be as high as possible. Although organic EL devices containing phosphorescent materials provide higher current efficiency (candle (cd) / ampere than those containing fluorescent materials) (A)) When a conventional material such as BAlq or CBP is used as the phosphorescent host material, a sufficiently high driving voltage is required as compared with an organic EL device using a fluorescent material. Therefore, in terms of power efficiency (lumens (lm)/ There is no advantage in the aspect of the tile (W). (3) Furthermore, the organic EL device has a short service life and still needs to improve its luminous efficiency. The international patent case disclosed in WO Patent Application Publication No. WO 2006/049013 discloses that it has a condensed a bicyclic group as a skeleton structure for a compound of an organic electric field luminescent material. However, it does not disclose a nitrogen-containing fused bicyclic group, and each of the 3-position and the 9-position is coupled with an aromatic ring. A cycloalkyl or heterocycloalkyl-substituted carbazolyl group, and a compound fused with a heterocyclic alkyl group or a cycloalkyl group of an aromatic ring. SUMMARY OF THE INVENTION Problems to be Solved The object of the present invention is to provide a method for Organic electricity a compound of a material having an excellent structure which imparts high luminous efficiency and long service life to the device and has suitable color coordinates; and an organic electric field light having high efficiency and long life using the compound 95566 4 201249960 Means for Solving the Problem The inventors of the present invention found that 'the above-mentioned object can be achieved by the compound represented by the following formula 1:
其中， 1^與b係個別獨立表示單鍵、經取代或未經取代之2 員至30員伸雜芳基、經取代或未經取代之（C6—C30)伸芳 基、或經取代或未經取代之（[6_[30)伸％烧基’ Χι係表示CH或N ; Υι與Y2係個別獨立表示_〇-、_S-、-CReRg-或-NR1Q-; R,至Ri。係個別獨立表示氫、氘、鹵素、經取代或未經 取代之（C1-C30)烷基、經取代或未經取代之（C6-C30)芳 基、經取代或未經取代之3員至30員雜芳基、經取代或未 經取代之（C3-C30)環烷基、經取代或未經取代之5員至γ 員雜環烷基、經取代或未經取代之（C6-C30)芳基（(n-C30) 烷基、與至少二f固笔要多-或H取-代之(C6-C30)芳基稠合 之（C3-C30)環烷基 '與至少一個經取經、系代之 (C6-C30)芳族環稠合之5員至7員雜環烷基、與至少、一猶 95566 5 201249960 經取代或未經取代之（C6-C30)芳族環稠合之（C3-C30)環烷 基、-NR21R22、-SiR23R24R25、-SR26、-0R27、經取代或未經取 代之（C2-C30)烯基、經取代或未經取代之（C2-C30)炔基、 氰基、硝基、或羥基；或經由經取代或未經取代之（C3-C30) 伸烷基或（C3-C30)伸烯基鏈結至相鄰取代基以形成其中一 個或多個碳原子可經選自氮、氧及硫之至少一個雜原子替 代之單環或多環之脂環族或芳族環； R2]至R27係具有與Rl至Rio之一者相同之定義； a、b、e及g係個別獨立表示之整數1至4;其中， 當a、b、e或g係2或更大之整數時，每個Ri、每個R2、 每個Rs或每個R7係相同或不同； c、d及f係個別獨立表示之整數1至3;其中，當c、 d或f係2或更大之整數時，每個R3、每個R4、或每個R6 係相同或不同；以及 該雜環烷基及該（伸）雜芳基係含有選自B、N、0、S、 P(=0)、Si及P之至少一個雜原子。 發明之效果 根據本發明之用於有機電子材料之化合物可製造具 有高發光效率及長使用壽命的有機電場發光裝置。 【實施方式】 後文中，將詳細揭示本發明。然而，下述說明係欲以 解釋本發明，而非意指以任何方式限定本發明之範疇。 本發明係關於藉由上式1表示之用於有機電子材料之 化合物以及包含該化合物之有機電場發光裝置。 95566 6 201249960 本文中，「（Cl-C30)(伸）烷基」係意指具有1個至3〇 個碳原子之直鏈或分支鏈（伸）烧基，其中，碳原子之數目 較佳係1至20 ’更佳係1至10 ’且包括曱基、乙基、正丙 基、異丙基、正丁基、異丁基、第三丁基等；r (C2_C3〇)(伸） 烯基」係意指具有2個至30個碳原子之直鏈或分支鏈（伸） 埽基，其中，碳原子之數目較佳係2至2 0，更佳係2至1 〇， 且包括乙烯基、1-丙烯基、2-丙烯基、ι_丁烯基、2_丁婦 基、3-丁烯基、2-曱基丁-2-烯基等；「（C2-C3〇)炔基」係 具有2個至30個碳原子之直鏈或分支鏈炔基，其中，碳原 子之數目較佳係2至20,更佳係2至1〇，且包括乙炔基、 1-丙炔基、2-丙炔基、1-丁炔基、2_丁炔基、3_丁炔基、 1甲基戊-2-炔基等；「（C1-C30)烷氧基」係具有i個至3〇 個碳原子之直鏈或分支鏈烷氡基，其中’碳原子之數目較 佳係1至20,更佳係1至10,且包括甲氧基、乙氧基、丙 氧基、異丙氧基、1-乙基丙氧基等；r(C3_C3〇)環烷基」係 具有3個至30個碳原子之單環或多環烴基，其中，碳原子 之數目較佳係3至20，更佳係3至7，且包括環丙基、環 丁基、環戊基、環己基等；「（C6_C3〇)環伸院基」係藉由自 具有6個至30個、較佳係6個至2〇個，更佳係6個或7 個碳原子之環烧基移除一個氫所形成之基；以及，「5員至 7員雜環烧基」係具有選自B、N、〇、s、p(=〇)、^及p ,至少一個雜原子’較佳係N、〇及S，且具有5個至7個 %骨架原子之環院基’且包括四氫D夫喃"叫。定、四氮逢 吩（thiolan)、四氫哌喃等；「（C6_C3〇)(伸）芳基」係自具 95566 7 201249960 有6至30個碳原子之芳族烴衍生之單環或稠環，其中，碳 原子之數目較佳係6至20,更佳係6至12,且包括苯基、 聯苯基、聯三笨基（terphenyl)、萘基、苐基、菲基、蒽基、 茚基、聯伸三苯基、祐基、稍曱苯基（tetracenyl)、茈基、 蒯基（chrysenyl)、稠四苯基（naphthacenyl)、丙二烯合苐 基（fluoranthenyl)等。再者’「3員至30員（伸）雜芳基」 係具有至少一個，較佳1個至4個選自下列B、N、0、S、 P(=0)、Si及P組成之群組之雜原子以及3個至30個環骨 架原子的芳基；其係單環或與至少一個苯環稠合之稠合 環；較佳係具有5個至21個，更佳係5個至12個環骨架 原子；可為部份飽和；可藉由將至少一個雜芳基或芳基經 一個或多個單鍵與雜芳基鏈結而形成；以及，係包括單環 型雜芳基，包括°夫°南基、°塞吩基、°比p各基、味嗤基、η比嗤 基、噻唑基、噻二唑基、異噻唑基、異噚唑基、噚唑基、 口等二嗤基、三哄基、四卩井基、三峻基、四β坐基、咬咕基、 吡啶基、吡哄基、嘧啶基、嗒畊基等，以及稠環型雜芳基， 包括苯并呋喃基、笨并噻吩基、異苯并呋喃基、二苯并呋 喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并異 °塞唾基、苯并異卩琴嗤基、苯并曙嗤基、異,π朵基、,υ朵基、 。弓丨嗤基、苯并°塞二嗤基、哇琳基、異啥琳基、增琳基 (cinnolinyl)、喹唑啉基、喹卩f琳基、咔唑基、啡畊基、 啡咬基、苯并二曙呃基（benzodioxoiyl)等。「鹵素」係包 括 F、Cl、Br及 I。 本文中，「經或未經取代」中表述之「經取代」係意 95566 8 201249960 指特定官能基之氫原子係經另一原子或基（亦即，取代基） 所替代。所述與L2、Ri至Rig及心至R27基中之該經取代 之（伸）烷基、該經取代之烯基、該經取代之炔基；^該經取 代之伸環提基、該經取代之環烧基、該經取代之雜環产美 該經取代之（伸）芳基、該經取代之（伸）雜芳基及該代 之芳族環上的取代基係個別獨立選自下列組成之群組之至 少一者：氘、鹵素、經鹵素取代或未經取代之（cl_C3〇)烷 基、（C6-C30)芳基、經（C6-C30)芳基取代或未經取代之^ 員至30員雜芳基、（C3-C30)環烧基、5員至7員雜變烧美、 (C1-C30)烷基矽烷基（&11^13丨171)、（〔6气30)芳基矽烷基、 (C1-C30)烷基（C6-C30)芳基矽烷基、（C2_C3〇)稀基' (C2-C30)炔基、氰基、咔唑基、（C1-C30)烷基胺基、（C6_C3〇) 方基fee基、（C1-C30)烧基（C6-C30)芳基胺基、（C6-C30)芳 基硼Ik基、（C1-C30)烧基蝴幾基、（C1-C30)烧基（C6-C30) ^•基棚％基、（C6-C30)芳基（C1-C30)烧基、（C1-C30)烧基 (C6-C30)芳基、羰基、羧基、硝基及羥基。 於上式1中，與b較佳係個別獨立為單鍵、經取 代或未經取代之5員至21員伸雜芳基、經取代或未經取 代之（C6-C20)伸芳基、或經取代或未經取代之（C6_C2〇) 伸環芳基’更佳係選自下列組成群組之一者：單鍵、伸笨 基、伸桌基、伸聯苯基、伸聯三苯基（terphenylene)、伸 蒽基、andenylene、伸第基、伸菲基、伸聯伸三苯基 (triphenylenylene)、伸芘基、phenylenylene、伸蒯基 (chrysenylene)、伸稠四苯基（naphthasenylene)、丙二烯 95566 9 201249960 合苐基（fluorantenyl)、伸呋喃基、伸噻吩基、伸吡π各基、 伸咪唑基、伸吡唑基、伸噻唑基、伸噻二唑基、伸異嘆喷 基、伸異噚唑基、伸噚唑基、伸卩f二唑基、伸三哄基、伸 四畊基、伸***基、伸四唑基、伸呋咕基、伸吡啶基、伸 吼畊基、伸°密啶基、伸嗒卩并基、伸苯并呋喃基、伸苯并嘆 吩基、伸異苯并呋喃基、伸苯并咪唑基、伸苯并噻唾基、 伸苯并異噻唑基、伸苯并異噚唑基、伸笨并卩萼唑基、伸異 吲哚基、伸吲哚基、伸吲唑基、伸苯并噻二唑基、伸啥琳 基、伸異喧淋基、伸01琳基（cinnol inylene)、伸啥峻琳基、 伸喧卩f琳基、伸啼唾基、伸啡咬基、伸苯并二卩萼呢基 (benzodioxolylene)、伸二苯并呋喃基及伸二苯并噻吩 基。 於上式1中，Y】與丫2係個別獨立表示-〇-、-S-、-cr8R卜 或-NRm-’其中’ Re與匕較佳係個別獨立為經取代或未經 取代之（Cl-C30)烷基或經取代或未經取代之（C6-C30)芳 基；或Rs與R9各經由經取代或未經取代之（C3-C30)伸烷基 或（C3-C30)伸烯基鏈結至相鄰取代基以形成單環或多環之 脂環族或芳族環，更佳係個別獨立表示未經取代之（c卜cl〇) 炫基或未經取代之（C6-C12)芳基、或鏈結至相鄰取代基以 形成單環或多環之（C1-C10)脂環族或（C6-C15)芳族環。以 及，“較佳係表示經取代或未經取代之（C6_C3〇)芳基或經 取代或未經取代之3員至30員雜芳基，更佳係表示經或未 經;11 _素、（C1-C6)烧基或（C6-C12)芳基取代之（C6—C20) 芳基，或經（C6-C12)芳基取代之5員至21員雜芳基。 95566 10 201249960 於上式1中’匕至R7較佳係個別獨立表示氫、經取代 或未經取代之（C6-C30)芳基或-SiR^M25、或經由經取代 或未經取代之（C3-C30)伸烧基或（C3-C30)伸烯基鏈結至相 鄰取代基以形成單環或多環之脂環族或芳族環，更佳係個 別獨立表示氫、未經取代之（C6-C12)芳基或-SiR23R24R25、 或鏈結至相鄰取代基以形成單環或多環（C6-C12)芳族環。Wherein, 1 and b are each independently represented by a single bond, substituted or unsubstituted 2 to 30 membered heteroaryl, substituted or unsubstituted (C6-C30) extended aryl, or substituted or Unsubstituted ([6_[30)extension%] Χι means CH or N; Υι and Y2 are individually independent _〇-, _S-, -CReRg- or -NR1Q-; R, to Ri. Individually independently represented by hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3 member 30-membered heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5 member to gamma heterocycloalkyl, substituted or unsubstituted (C6-C30 An aryl ((n-C30) alkyl group, a (C3-C30) cycloalkyl group fused to at least a di-f-type pen- or a H-substituted (C6-C30) aryl group, and at least one A 5- to 7-membered heterocycloalkyl group fused with a (C6-C30) aromatic ring, and a (C6-C30) aromatic ring thickened with at least one of the urethanes 95566 5 201249960 (C3-C30)cycloalkyl, -NR21R22, -SiR23R24R25, -SR26, -OR27, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) Or alkynyl, cyano, nitro, or hydroxy; or via a substituted or unsubstituted (C3-C30) alkyl or (C3-C30) alkyl group to an adjacent substituent to form one or The plurality of carbon atoms may pass through at least one of the impurities selected from the group consisting of nitrogen, oxygen and sulfur Substituted monocyclic or polycyclic alicyclic or aromatic ring; R2] to R27 have the same definition as one of R1 to Rio; a, b, e, and g are individually independent integers 1 to 4 Wherein, when a, b, e or g is an integer of 2 or more, each Ri, each R2, each Rs or each R7 is the same or different; c, d and f are individually independent representations Integer 1 to 3; wherein, when c, d or f is an integer of 2 or more, each R3, each R4, or each R6 is the same or different; and the heterocycloalkyl group and the (extension) The heteroaryl group contains at least one hetero atom selected from the group consisting of B, N, 0, S, P (=0), Si, and P. Effect of the Invention The compound for an organic electronic material according to the present invention can be manufactured to have high luminous efficiency. The present invention will be described in detail below. However, the following description is intended to explain the present invention, and is not intended to limit the scope of the invention in any way. A compound for an organic electronic material represented by the above formula 1 and an organic electric field light-emitting device comprising the same. 6 201249960 As used herein, "(Cl-C30) (alkyl)" means a straight or branched chain having from 1 to 3 carbon atoms, wherein the number of carbon atoms is preferably 1 to 20 'more preferably 1 to 10' and includes mercapto, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, etc.; r (C2_C3〇) (extension) The term "base" means a straight or branched chain thiol group having 2 to 30 carbon atoms, wherein the number of carbon atoms is preferably from 2 to 20, more preferably from 2 to 1 Å, and includes ethylene. , 1-propenyl, 2-propenyl, i-butenyl, 2-butenyl, 3-butenyl, 2-mercaptobut-2-enyl, etc.; "(C2-C3〇) alkyne And a linear or branched alkynyl group having 2 to 30 carbon atoms, wherein the number of carbon atoms is preferably 2 to 20, more preferably 2 to 1 Å, and includes ethynyl group, 1-propyne , 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.; "(C1-C30) alkoxy" has i a linear or branched alkane group of up to 3 carbon atoms, wherein the number of 'carbon atoms is preferably from 1 to 20, more preferably from 1 to 10 And includes methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, etc.; r(C3_C3〇)cycloalkyl" is a single ring having 3 to 30 carbon atoms Or a polycyclic hydrocarbon group, wherein the number of carbon atoms is preferably from 3 to 20, more preferably from 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.; "(C6_C3〇) ring extension "house-based" is a group formed by removing one hydrogen from a ring-burning group having 6 to 30, preferably 6 to 2, more preferably 6 or 7 carbon atoms; and, The 5- to 7-membered heterocyclic group has a group selected from the group consisting of B, N, 〇, s, p(=〇), ^ and p, and at least one hetero atom is preferably N, 〇 and S, and has 5 Up to 7% of the skeleton atoms of the ring courtyard 'and including tetrahydro Duffan " , thiolan, tetrahydropyran, etc.; "(C6_C3〇) (extension) aryl" is derived from 95566 7 201249960 aromatic hydrocarbon derived from 6 to 30 carbon atoms. a ring wherein the number of carbon atoms is preferably from 6 to 20, more preferably from 6 to 12, and includes a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group. , mercapto, triphenyl, ketone, tetracenyl, sulfhydryl, chrysenyl, naphthacenyl, fluoranthenyl, and the like. Further, '3 to 30 members (extended) heteroaryl group) has at least one, preferably 1 to 4, selected from the group consisting of B, N, 0, S, P (=0), Si and P. a hetero atom of the group and an aryl group of 3 to 30 ring skeleton atoms; which is a monocyclic ring or a fused ring fused to at least one benzene ring; preferably 5 to 21, more preferably 5 Up to 12 ring skeleton atoms; may be partially saturated; may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and, including monocyclic heteroaryls Base, including sulphate, septyl, °, p, sulphate, η, thiol, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, carbazolyl, Ordinary dimercapto, triterpene, tetraterpenoid, trisyl, tetra-beta, sulfhydryl, pyridyl, pyridyl, pyrimidinyl, hydrazine, etc., and fused ring heteroaryl , including benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benziso-saltyl, benzo Heteroquinone Group, isobutyl, [pi] yl flower flowers ,, υ group.丨嗤 丨嗤, benzo-dithiol, wahrine, isolinyl, cinnolinyl, quinazolinyl, quinoxaline, carbazolyl, phenyl phenyl, morphine Base, benzodioxoiyl and the like. "Halogen" includes F, Cl, Br and I. As used herein, the term "substituted" as used in "unsubstituted or unsubstituted" means that a hydrogen atom of a particular functional group is replaced by another atom or radical (i.e., a substituent). And the substituted (extended) alkyl group in the group of L2, Ri to Rig and the core to R27, the substituted alkenyl group, the substituted alkynyl group; a substituted cycloalkyl group, the substituted heterocyclic ring, the substituted (extended) aryl group, the substituted (extended) heteroaryl group, and the substituent on the aromatic ring of the generation are individually selected independently At least one of the group consisting of: hydrazine, halogen, halogen-substituted or unsubstituted (cl_C3 〇) alkyl, (C6-C30) aryl, substituted by (C6-C30) aryl or not Substituted to 30-membered heteroaryl, (C3-C30) cycloalkyl, 5- to 7-membered heterozygous, (C1-C30)alkyldecyl (&11^13丨171), ( [6 gas 30) aryl decyl, (C1-C30) alkyl (C6-C30) aryl decyl, (C2_C3 fluorene) dilute (C2-C30) alkynyl, cyano, carbazolyl, C1-C30)alkylamino group, (C6_C3〇) aryl Fee group, (C1-C30)alkyl (C6-C30) arylamine group, (C6-C30) aryl boron Ik group, (C1-C30 ) calcinyl group, (C1-C30) alkyl (C6-C30) ^• base steryl group, (C6-C30) aryl (C1-C30) alkyl group, (C1-C30 Carboxyl (C6-C30) aryl, carbonyl, carboxyl, nitro and hydroxy groups. In the above formula 1, it is preferred that b is independently a single bond, a substituted or unsubstituted 5 member to 21 member heteroaryl group, a substituted or unsubstituted (C6-C20) extended aryl group, Or substituted or unsubstituted (C6_C2〇) Cyclo-aryl aryl is more preferably selected from one of the following groups: single bond, extended base, extended base, extended phenyl, extended triphenyl Terphenylene, thiol, andenylene, thiophene, phenanthrene, triphenylenylene, phenylenylene, chrysenylene, naphthasenylene, Propadiene 95566 9 201249960 fluorantenyl, hexanyl, thienyl, pyridyl, imidazolium, pyrazolyl, thiazolyl, thiadiazole, sigh Base, exoisoxazole group, exocarbazole group, exfoliation f oxadiazole group, extensin trisyl group, four cultivating base, triazolyl group, tetrazolyl group, exofuranyl group, exopyridine group, exfoliation Base, extension of pyridine group, hydrazine, benzofuranyl, benzophenanthene, benzofuranyl, benzoimidazolyl, benzene And thiazino, benzoisothiazolyl, benzoxazole, stupid and carbazolyl, exo- hydrazino, hydrazino, carbazolyl, benzothiadiazole Basis, 啥 啥 基 基 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Benzodioxolylene, dibenzofuranyl and dibenzothiophenyl. In the above formula 1, Y] and 丫2 are each independently represented by -〇-, -S-, -cr8R or -NRm-', wherein 'Re and 匕 are preferably independently substituted or unsubstituted ( Cl-C30)alkyl or substituted or unsubstituted (C6-C30) aryl; or Rs and R9 each via substituted or unsubstituted (C3-C30) alkyl or (C3-C30) The alkenyl chain is bonded to an adjacent substituent to form a monocyclic or polycyclic alicyclic or aromatic ring, and more preferably independently represents an unsubstituted (c bcl〇) danthyl group or an unsubstituted group (C6 -C12) aryl, or linked to adjacent substituents to form a monocyclic or polycyclic (C1-C10) alicyclic or (C6-C15) aromatic ring. And, "preferably means a substituted or unsubstituted (C6_C3〇) aryl group or a substituted or unsubstituted 3 to 30 membered heteroaryl group, more preferably an or not; 11- (C1-C6) aryl or (C6-C12) aryl substituted (C6-C20) aryl, or substituted by (C6-C12) aryl from 5 to 21 membered heteroaryl. 95566 10 201249960 In the formula 1, '匕 to R7 are preferably independently represented by hydrogen, substituted or unsubstituted (C6-C30) aryl or -SiR^M25, or via substituted or unsubstituted (C3-C30) stretching. An alkyl group or a (C3-C30) chain extending to an adjacent substituent to form a monocyclic or polycyclic alicyclic or aromatic ring, more preferably independently hydrogen, unsubstituted (C6-C12 An aryl group or -SiR23R24R25, or linked to an adjacent substituent to form a monocyclic or polycyclic (C6-C12) aromatic ring.
於上式1中， 係選自下列結構，但並不 限於此：In the above formula 1, it is selected from the following structures, but is not limited thereto:
本發明之代表性化合物係包括下列化合物： 95566 11 201249960Representative compounds of the invention include the following compounds: 95566 11 201249960
95566 12 20124996095566 12 201249960
95566 13 20124996095566 13 201249960
95566 14 20124996095566 14 201249960
子材料之化合物可根據下 、、根據本㈣之用於有機電 述反應式製備之。 [反應式]The compound of the sub-material can be prepared according to the following (4) for the organic electrorheological reaction formula. [Reaction formula]
此外本發明係提供包含式i化合物之有機電場發光 裝置。該有機電場發光裝置係包含第一電極、第二電極、 以及介於該第一電極與該第二電極之間之至少一層有機 層。該有機層係包含至少一種根據本發明之式丨化合物。 再者，該有機層係包含發光層，該發光層係包含作為主體 材料之該式1化合物。 此外’與根據本發明之主體材料合用於有機電場發光 裝置中之碟光撸雜劑係可選自藉由下式2表示之化合物：Furthermore, the present invention provides an organic electric field illuminating device comprising a compound of formula i. The organic electric field light-emitting device includes a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode. The organic layer comprises at least one hydrazine compound according to the invention. Further, the organic layer contains a light-emitting layer containing the compound of the formula 1 as a host material. Further, the dishing agent used in the organic electroluminescence device in combination with the host material according to the present invention may be selected from the compounds represented by the following formula 2:
MlL10V0V03 --------------------- (2) 其中，Μ1係選自Ir、Pt、Pd及Os組成之群組；Lm、 95566 15 201249960 L1D2及Lm係個別獨立選自下列結構：MlL10V0V03 --------------------- (2) where Μ1 is selected from the group consisting of Ir, Pt, Pd and Os; Lm, 95566 15 201249960 L1D2 and The Lm series are individually selected from the following structures:
R2〇1至R2D3係個別獨立表示氫、氘、經一個或多個鹵素 取代或未經取代之（C1-C30)烷基、經一個或多個（C1-C30) 烷基取代或未經取代之（C6-C30)芳基、或_素； 尺2〇4至Rm係個別獨立表示氫、氘、經取代或未經取代 之（C1-C30)烷基、經取代或未經取代之（C1-C30)烷氧基、 經取代或未經取代之（C3-C30)環烷基、經取代或未經取代 之（C2-C30)烯基、經取代或未經取代之（C6-C30)芳基、經 95566 16 201249960 取代或未經取代之單（C1~C30)烷基胺基、經取代或未經取 代之二（C1-C30)烷基胺基、經取代或未經取代之單（C6-C30) 芳基胺基、經取代或未經取代之二（C6-C30)芳基胺基、SF5、 經取代或未經取代之三（C卜C30)烷基矽烷基、經取代或未 經取代之二（Cl-C30)烧基（C6-C30)芳基梦烧基、經取代或 未經取代之三（C6-C30)芳基矽烷基、氰基或鹵素； R22。至R223係個別獨立表示氫、氘、經一個或多個_素 取代或未經取代之（C1-C30)烧基、或經一個或多個 烷基取代或未經取代之（C6-C30)芳基； 尺224與R225係個別獨立表示氫、氣、經取代或未經取代 之（n-C30)烷基、經取代或未經取代之（C6_C3〇)芳基、或 鹵素’或1^4與R225可藉由具有或不具有稠環之（C3_C12) 伸烧基基或（C3-C12)伸烯基彼此鏈結，以形成單環或多環 之脂環族或芳族環； R226係表示經取代或未經取代之（C1-C30)烷基、經取代 或未經取代之（C6-C30)芳基、經取代或未經取代之5員或 30貝雜^•基、或鹵素； 至R229係個別獨立表示氫、氘、經取代或未經取代 之（C1-C30)烷基、經取代或未經取代之（C6-C30)芳基或鹵 素； R23^R232 係表示 、 只2成236或 R239尺240 ;R231至R242係個 別獨立表示氫、氣、經一個或多個齒素取代或未經取代之 (C1-C30)燒基、（Ci_c3〇)烷氧基、齒素、經取代或未經取 95566 17 201249960 代之（C6-C30)^r基、象基、或經取代或未經取代之（c5_c3〇) 環烷基，或至R242可個別經由（C2_C3〇)伸烷基基或 (C2-C30)伸烯基鏈結至相鄰取代基以形成螺環或稠合環， 或可經由（C2-C30)伸烷基基或（C2-C30)伸烯基鏈結至Rm 或Rm以形成飽和或不飽和之稠合環。 式2之摻雜劑係包括下列，但並不限於此：R2〇1 to R2D3 are each independently represented by hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl by one or more halogens, substituted or unsubstituted by one or more (C1-C30) alkyl groups. (C6-C30) aryl, or _ s; s. 2 〇 4 to Rm each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted ( C1-C30) alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30 Aryl, substituted or unsubstituted mono(C1~C30)alkylamino, substituted or unsubstituted bis(C1-C30)alkylamino, substituted or unsubstituted, 95566 16 201249960 Mono(C6-C30)arylamino, substituted or unsubstituted bis(C6-C30)arylamino, SF5, substituted or unsubstituted tris(CbC30)alkyldecyl, by Substituted or unsubstituted bis(Cl-C30)alkyl (C6-C30) aryl carbyl, substituted or unsubstituted tris(C6-C30) arylalkyl, cyano or halogen; R22. To R223, each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted with one or more alkyl groups (C6-C30) Aryl; 224 and R225 independently represent hydrogen, gas, substituted or unsubstituted (n-C30) alkyl, substituted or unsubstituted (C6_C3〇) aryl, or halogen 'or 1^ 4 and R225 may be linked to each other by a (C3_C12) alkylene group or a (C3-C12)alkylene group having a fused ring to form a monocyclic or polycyclic alicyclic or aromatic ring; R226 Is a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted 5 member or 30 Å, or Halogen; to R229 are each independently represented by hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen; R23^R232 is represented by Only 2 into 236 or R 239 ft. 240; R231 to R242 are each independently represented by hydrogen, gas, substituted or unsubstituted (C1-C30) alkyl, (Ci_c3〇) alkoxy, toothed by one or more dentants Prime Substituted or not taken 95566 17 201249960 (C6-C30)^r, yl, or substituted or unsubstituted (c5_c3〇) cycloalkyl, or to R242 may be individually extended via (C2_C3〇) An alkyl group or (C2-C30)alkylene chain to an adjacent substituent to form a spiro or fused ring, or may be extended via an alkyl group or a (C2-C30) alkyl group. Junction to Rm or Rm to form a saturated or unsaturated fused ring. The dopant of Formula 2 includes the following, but is not limited thereto:
<1<1
95566 20124996095566 201249960
根據本發明之有機電場發光裝置除了包含式1表示之 化合物外，可復包含至少一種選自芳基胺系化合物與苯乙 烯基芳基胺系化合物組成之群組的化合物。 於根據本發明之有機電場發光裝置中，該有機層可復 包含至少一種選自下列所組成群組之金屬：元素週期表第 1族之金屬、第2族之金屬、第4周期之過渡金屬、第5 周期之過渡金屬、鑭系金屬及d-過渡元素之有機金屬，或 至少一種包含該金屬之錯合物化合物。該有機層可包含發 光層及電荷產生層。 根據本發明之電場發光裝置藉由除了包含根據本發 明之化合物的有機層外，復包含至少一層包含藍色電場發 光化合物、紅色電場發光化合物或綠色電場發光化合物的 發光層，可發射白光。 於根據本發明之有機電場發光裝置中，較佳係將至少 一層（下文中稱為「表面層」）選自硫屬元素化合物層 (chalcogenide layer)、金屬鹵化物層與金屬氧化物層之 層體設置於一個或兩個電極之一個或多個内表面上。具體 而言，較佳係將石夕或銘之琉屬元素化合物（包含氧化物）層 設置於電場發光介質層之陽極表面上，並將金屬鹵化物層 或金屬氧化物層設置於EL介質層之陰極表面上。此表面層 95566 19 201249960 向該有機電場發光裝置提供操作安定性。較佳地，該硫屬 兀素化合物係包括 Si〇x(l^x^2)、Al〇x(lgx$15)、The organic electroluminescence device according to the present invention may further comprise, in addition to the compound represented by Formula 1, at least one compound selected from the group consisting of an arylamine compound and a styrene arylamine compound. In the organic electric field light-emitting device according to the present invention, the organic layer may further comprise at least one metal selected from the group consisting of a metal of Group 1 of the periodic table, a metal of Group 2, and a transition metal of the fourth cycle. , a transition metal of the fifth cycle, an organometallic of a lanthanide metal and a d-transition element, or at least one complex compound containing the metal. The organic layer may include a light emitting layer and a charge generating layer. The electric field light-emitting device according to the present invention emits white light by including at least one light-emitting layer containing a blue electric field light-emitting compound, a red electric field light-emitting compound or a green electric field light-emitting compound in addition to the organic layer containing the compound according to the present invention. In the organic electroluminescence device according to the present invention, at least one layer (hereinafter referred to as "surface layer") is preferably selected from the group consisting of a chalcogenide layer, a metal halide layer and a metal oxide layer. The body is disposed on one or more inner surfaces of one or both of the electrodes. Specifically, it is preferable to provide a layer of a cerium element compound (including an oxide) of Shi Xi or Ming on the anode surface of the electric field luminescent medium layer, and to provide a metal halide layer or a metal oxide layer on the EL medium layer. On the surface of the cathode. This surface layer 95566 19 201249960 provides operational stability to the organic electric field illuminating device. Preferably, the chalcogenide compound comprises Si〇x (l^x^2), Al〇x (lgx$15),
SiAlON 4，該金屬鹵化物係包括LiF、MgF2、、 稀土金屬之氟化物等；以及，該金屬氧化物係包括Cs2〇、 Li2〇、Mg〇、SrO、BaO、CaO 等。 於根據本發明之有機電場發光裝置中，較佳可將電子 傳輪化合物與還原性摻雜劑之混合區域、或電洞傳輸化合 物與氧化性摻雜劑之混合區域設置於成對電極的至少一個 表面上。於此例中，電子傳輸化合物被還原成陰離子，因 而電子自混合區域注入與傳輸至電場發光介質變得更加容 易。再者，電洞傳輸化合物被氧化而形成陽離子，因此電 /同自混合區域注入與傳輸至電場發光介質變得更加容易。 較佳地，氧化性摻雜劑包括各種路易士酸（Lewis acid)與 接又者化合物（acceptor compound);還原性摻雜劑包括鹼 ，屬、鹼金屬化合物、鹼土金屬、稀土金屬及其混合物。 可採用還原性摻雜劑層作為電荷產生層，以製備具有兩層 或更夕層電場發光層且發射白光之電場發光裝置。 後文中，將參照下述實施例詳細解釋本發明之用於有 機電子材料之化合物、該化合物之製備方法及包含該化合 物之裝置的發光特性·· 製備例1 :化合物C-2之製備 95566 20 201249960SiAlON 4, the metal halide includes LiF, MgF2, a fluoride of a rare earth metal, and the like; and the metal oxide includes Cs2〇, Li2〇, Mg〇, SrO, BaO, CaO, and the like. In the organic electric field light-emitting device according to the present invention, it is preferable that at least a mixed region of the electron transporting compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant is disposed on the pair of electrodes. On a surface. In this case, the electron transporting compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to the electric field illuminating medium. Furthermore, the hole transporting compound is oxidized to form a cation, and thus it becomes easier to inject and transport the electric/synthesis region to the electric field illuminating medium. Preferably, the oxidizing dopant comprises various Lewis acids and acceptor compounds; the reducing dopants include alkalis, genus, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof . A reducing dopant layer may be employed as the charge generating layer to prepare an electric field light-emitting device having two or more layers of an electric field light-emitting layer and emitting white light. Hereinafter, the compound for an organic electronic material, the method for producing the compound, and the luminescent property of the device comprising the same according to the present invention will be explained in detail with reference to the following examples. Preparation Example 1: Preparation of Compound C-2 95566 20 201249960
化合物C-l-l之製備 將9-苯基-9H-咔唑-3-基硼酸（14公克（g), 48.76毫 莫耳（mmol))、3-漠 _911-〇卡嗤（10 g, 40.63 mmol)、K2CO3 (13. 5 g，97. 52 mmol)及 Pd(PPh3)4(2.35 g, 2. 03 mmol) 加入甲苯200毫升（mL)、EtOH 50 mL及純化水50 mL的混 合物中。將該反應混合物於90至100°C攪拌3小時後，將 該混合物冷卻至室溫。藉由重力分離而自該混合物移除水 層。濃縮所得有機層，與二氯甲烷（MC)—起研磨，隨後過 濾以獲得化合物C-l-l(12g，72%)。 化合物C-1-2之製備 將 2, 4-二氣喹唑啉（30 g，151 mmol)、9-苯基-9H-咔唑~3—基硼酸d5.6g，75.3mmol)、P(i(PPh3)4(2.6g，2. 3 咖〇1)及 Na2C〇3(i6 g，150 mmol)溶解於曱苯（300 mL)與蒸 餾水（75mL)之混合物中後，將該反應混合物於⑽它攪拌2 夺於減墨下蒸顧所得有機層，隨後與MeOH—起研磨。 =所传固體溶解於MC中，透過⑦膠過遽，隨後與及己 元起研磨以獲得化合物C-l-2(9.3g，51.4%)。 化合物C-2之製備 將化合物 C~l — 1(5.3 g，14. 7 mmol)及化合物 c-1-2 •4S’ 15·8_ο1)懸浮於二曱基甲醯胺（MF)8()mL之後， 95566 21 201249960 於室溫將60°/〇 NaH (948毫克（mg)，22 mmol)加入該混合物 中。攒拌所得反應混合物12小時。加入純化水（1公升（l)) 之後，於減壓下過濾混合物。將所得固體與乙酸乙 酯一起研磨，溶解於MC中，透過矽膠過濾，隨後與MC/正 己烷一起研磨以獲得化合物C-2(1.9 g，16.8%)。 MS/FAB測量值為778 ;計算值為777. 91 製備例2 :化合物C-13之製備Preparation of Compound C11 9-Phenyl-9H-indazol-3-ylboronic acid (14 g (g), 48.76 mmol (mmol)), 3-Day _911-〇卡嗤 (10 g, 40.63 mmol) K2CO3 (13.5 g, 97.52 mmol) and Pd(PPh3)4 (2.35 g, 2.03 mmol) were added to a mixture of 200 ml (mL) of toluene, 50 mL of EtOH and 50 mL of purified water. After the reaction mixture was stirred at 90 to 100 ° C for 3 hours, the mixture was cooled to room temperature. The aqueous layer is removed from the mixture by gravity separation. The obtained organic layer was concentrated, triturated with dichloromethane (MC), and then filtered to afford Compound C-1 (12 g, 72%). Preparation of compound C-1-2 2,4-dioxaquinazoline (30 g, 151 mmol), 9-phenyl-9H-carbazole~3-boronic acid d5.6 g, 75.3 mmol), P ( After i(PPh3)4 (2.6g, 2.3 gurry 1) and Na2C〇3 (i6 g, 150 mmol) were dissolved in a mixture of toluene (300 mL) and distilled water (75 mL), the reaction mixture was (10) It agitates 2 to obtain the organic layer obtained by steaming under reduced ink, and then grinds with MeOH. = The solid is dissolved in MC, passed through 7 gel, and then ground with H1 to obtain compound Cl-2. (9.3g, 51.4%) Preparation of Compound C-2 Compound C~l-1 (5.3 g, 14.7 mmol) and compound c-1-2 •4S' 15·8_ο1) were suspended in diterpene After guanamine (MF) 8 () mL, 95566 21 201249960 60 ° / 〇 NaH (948 mg (mg), 22 mmol) was added to the mixture at room temperature. The resulting reaction mixture was stirred for 12 hours. After adding purified water (1 liter (l)), the mixture was filtered under reduced pressure. The obtained solid was triturated with ethyl acetate, dissolved in MC, filtered through silica gel, and then triturated with MC/n-hexane to obtain Compound C-2 (1.9 g, 16.8%). The MS/FAB measurement was 778; the calculated value was 777. 91 Preparation 2: Preparation of Compound C-13
化合物C-2-1之製備 將2, 4-二氣喹唑啉（50 g，251 mmol)及二苯并[b，d] 呋喃-4-基硼酸（53.2 g，251 mmol)溶解於曱苯（1 l)與水 (200 mL)之混合物中之後，將肆（三苯基膦）合鈀（14. 5 g， 12. 5 mmol)及碳酸鈉（8〇 g，755 mmol)加入該反應混合物 中。將該反應混合物於80°C攪拌20小時，冷卻至室溫。 以氯化敍水溶液200 mL終止反應後，以乙酸乙酯1 [萃 取反應混合物，並以二氯甲烷1 L進一步萃取水層。以無 水硫酸鎂乾燥有機層，並於減壓下移除。透過矽膠過濾所 得固體，並於減壓下移除溶劑。以乙酸乙酯（Et〇Ac) 1〇〇mL 洗滌所得固體以獲得化合物C-2-l(50 g，74 %)。 化合物C-13之製備 將化合物C-1-1 (50 g，122 mmol)溶解於DMF中後， 將60 % NaH (5. 9 g，148 mmol)緩慢加入該反應混合物中。 95566 22 201249960 將該反應混合物於室溫攪拌1小時後，將化合物C_2_K51 g，147 mmol)加入該反應混合物中。將反應混合物於室溫 攪拌20小時。將冰水緩慢滴加至反應混合物中，以終止反 應。隨後’過慮反應混合物以獲付所生成之固體。以水1L 洗條所得固體，接著以MeOH 1L洗蘇。乾燥所得固體，將 其溶解於CHCldL中，透過矽膠過濾以移除無機質。移除 所得溶液中之溶劑以獲得固體。於DMF中再結晶所得固體 以獲得化合物C-13(50 g，58 »。 MS/FAB測量值為703 ;計算值為702. 80 製備例3 :化合物C-14之製備 B(〇H)2 0¾Preparation of Compound C-2-1 2,4-Dioxaquinazoline (50 g, 251 mmol) and dibenzo[b,d]furan-4-ylboronic acid (53.2 g, 251 mmol) were dissolved in hydrazine. After a mixture of benzene (1 l) and water (200 mL), hydrazine (triphenylphosphine) palladium (14.5 g, 12.5 mmol) and sodium carbonate (8 〇g, 755 mmol) were added. In the reaction mixture. The reaction mixture was stirred at 80 ° C for 20 hours and cooled to room temperature. After the reaction was quenched with 200 mL of chlorinated aqueous solution, the mixture was extracted with ethyl acetate 1 [yield, and the aqueous layer was further extracted with 1 L of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and removed under reduced pressure. The solid obtained was filtered through silica gel and the solvent was removed under reduced pressure. The obtained solid was washed with 1 mL of ethyl acetate (EtOAc) to afford Compound C-2-l (50 g, 74%). Preparation of Compound C-13 After dissolving Compound C-1-1 (50 g, 122 mmol) in DMF, 60% NaH (5.9 g, 148 mmol) was slowly added to the reaction mixture. 95566 22 201249960 After the reaction mixture was stirred at room temperature for 1 hour, compound C 2 -K 51 g, 147 mmol) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 20 hours. Ice water was slowly added dropwise to the reaction mixture to terminate the reaction. The reaction mixture was then taken care of to yield the solid formed. The resulting solid was washed with 1 L of water and then washed with MeOH 1L. The resulting solid was dried, dissolved in CHCldL and filtered through a silica gel to remove inorganic material. The solvent in the resulting solution was removed to obtain a solid. The obtained solid was recrystallized from DMF to give Compound C-13 (50 g, 58). MS/FAB: 703. calc. 702. 80 Preparation Example 3: Preparation of Compound C-14 B (〇H) 2 03⁄4
C-3-1C-3-1
化合物C-3-1之製備 將2,4-二氣喹唑淋（5〇8，251111111〇1)及二苯并|^，(1] 噻吩-4-基硼酸（57.3 g，251 mmol)溶解於甲苯（1L)與水 (200 mL)之混合物中後，將肆（三笨基膦）合把（14. 5 g， 12· 5 mmol)及碳酸鈉（80 g，755 mmol)加入該反應混合物 中。將反應混合物於80°C擾拌20小時，冷卻至室溫。以 氣化銨水溶液200 inL終止反應後，以乙酸乙酯1L萃取反 應混合物，以二氣曱烷1L進一步萃取水層。以無水硫酸鎂 乾燥有機層，並於減壓下移除。透過矽膠過濾所得固體， 並於減壓下移除溶劑。以乙酸乙酯（EtOAc) 100 mL洗滌所 得固體以獲得化合物C-3-l(50g，60%)。 95566 23 201249960 化合物C-14之製備 將化合物C-l-l(50 g，122 mmol)溶解於DMF中後， 將60 % NaH(5. 9 g，148 mmol)緩慢加入該反應混合物中。 將該反應混合物於室溫攪拌1小時後，將化合物C-3-1 (51 g，147 mmol)加入該反應混合物中。將反應混合物於室溫 攪拌20小時。將冰水緩慢滴加至反應混合物中，以終止反 應。隨後，過濾反應混合物以獲得所生成之固體。以水1L 洗滌所得固體，接著以MeOH 1L洗滌。乾燥所得固體，將 其溶解於CHCh 4L中，透過矽膠過濾以移除無機質。移除 所得溶液中之溶劑以獲得固體。於DMF中再結晶所得固體 以獲得化合物C-14(50 g，57%)。 MS/FAB測量值為729 ;計算值為718. 87 製備例4 :化合物C-20之製備Preparation of compound C-3-1 2,4-dioxaquinazoline (5〇8,251111111〇1) and dibenzo-[^,(1] thiophen-4-ylboronic acid (57.3 g, 251 mmol) After dissolving in a mixture of toluene (1 L) and water (200 mL), hydrazine (triphenylphosphine) (14. 5 g, 12.5 mmol) and sodium carbonate (80 g, 755 mmol) were added. In the reaction mixture, the reaction mixture was stirred at 80 ° C for 20 hours, and cooled to room temperature. After quenching with 200 ml of aqueous ammonium chloride solution, the reaction mixture was extracted with 1 L of ethyl acetate, and water was further extracted with dioxane 1 L. The organic layer was dried over anhydrous MgSO.sub. 3-l (50g, 60%). 95566 23 201249960 Preparation of Compound C-14 After compound C11 (50 g, 122 mmol) was dissolved in DMF, 60% NaH (5.9 g, 148 mmol) was slowly added. In the reaction mixture, after the reaction mixture was stirred at room temperature for 1 hour, compound C-3-1 (51 g, 147 mmol) was added to the reaction mixture. The mixture was stirred at room temperature for 20 hours, and ice water was slowly added dropwise to the reaction mixture to terminate the reaction. Subsequently, the reaction mixture was filtered to obtain a solid which was formed. The obtained solid was washed with 1 L of water, followed by washing with MeOH 1 L. The obtained solid was dissolved in CHCh 4L and filtered through a silica gel to remove the inorganic substance. The solvent in the obtained solution was removed to obtain a solid. The obtained solid was recrystallized from DMF to obtain Compound C-14 (50 g, 57%) The MS/FAB measurement was 729; the calculated value was 718. 87 Preparation 4: Preparation of Compound C-20
化合物C-4-1之製備 將二苯并[b，d]呋喃-4-基棚酸（19 g，89.6 mmol)、 溴苯（18.4 mL，138 mmol)、Pd(PPh3)4(2.9 g，2.5 mmol) 及 Na2C〇3(23. 2 g，219 mmol)溶解於曱苯（375 mL)、EtOH (75 mL)與蒸镏水（75 mL)之混合物中後，將該反應混合物於 90°C攪拌4小時。於減壓下蒸餾所獲有機層，隨後以MC 及己烷透過管柱過濾以獲得化合物C-4-K17 g，77%)。 95566 24 201249960 化合物C-4-2之製備 將化s物C-4〜1(17 g，65.3 mmol)溶解於四氫吱喃 (THF)(5Q() mL)中之後，於-78°C 將 2. 5M 正丁基链（n-BuLi) 之己烷冷液（52. 2 mL，130 mmol)加入該反應混合物中，將 反應混ά物授拌1小時。將反應混合物授拌2小時，同時 將B(0i Pr)3(2l.8 mL，195 mmQl)缓慢加入該反應混合物 中加人2 M HC1 ,粹滅該反應混合物，以蒸顧水及EA萃取 反應此〇物。以及己烷再結晶所得固體以獲得化合物 C-4-2(6.4 g，33°/。）。 化合物（^4-3之製備 將化合物C-4~2(4. 9 g，24.4随〇1)、2,4-二氯喹唑 琳（6·4 S，22.2 mnml)、Pd(PPh3)4(11 g，2 5 顏⑷及 MO^7·1 g’ 66.6咖。1)溶解於甲笨（30G mL)與蒸餾水 (75 物中後’將該反應混合物於9代授摔2小 時二於減壓下洛餾所獲有機層’隨後與MeQH 研磨。將 斤得口體a解於mc中並透過;^膠過渡，隨後與MC及己说 一起研磨以獲得化合物C-4-3(4.1 g，45%)β 化合物C-20之製備 將化合物C+3(4.5 g，10.9 mraQl)與化合物c-h (4. 1 g，9, 9 mmol)懸浮於 DMF 80mL 中後，於室溫將 6〇% Ν&Η «Μ mg，14. 8 mmol)加入該混合物中。攪拌所得反應混合 物12小時。加入純化水（1L)後，於減壓下過濾該混合物.。 將所得固體與Me〇H/乙酸乙酯一起研磨’之後與DMF 一起 研磨，隨後與EA/THF —起研磨。將所得固體溶解於MC中， 95566 25 201249960 透過碎膠過滤’隨後與Me0H/EA —起研磨以獲得化合物 C-20 (3. 4 g，44 %)。 MS/FAB測量值為779 ;計算值為778. 9〇 製備例5 ··化合物C-21之製備Preparation of Compound C-4-1 Dibenzo[b,d]furan-4-yl succinic acid (19 g, 89.6 mmol), bromobenzene (18.4 mL, 138 mmol), Pd(PPh3)4 (2.9 g , 2.5 mmol) and Na2C〇3 (23.2 g, 219 mmol) were dissolved in a mixture of toluene (375 mL), EtOH (75 mL) and distilled water (75 mL). Stir at °C for 4 hours. The obtained organic layer was distilled under reduced pressure, and then filtered through a column of MC and hexane to obtain compound C-4-K17 g, 77%). 95566 24 201249960 Preparation of compound C-4-2 After dissolving the s material C-4~1 (17 g, 65.3 mmol) in tetrahydrofuran (THF) (5Q () mL), at -78 ° C A 2. 5M n-butyl chain (n-BuLi) in hexane cold (52.2 mL, 130 mmol) was added to the mixture and mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours while B (0i Pr) 3 (21.8 mL, 195 mm Ql) was slowly added to the reaction mixture to add 2 M HCl, and the reaction mixture was quenched to extract water and EA. Reacts this cockroach. The solid obtained was recrystallized from hexane to obtain Compound C-4-2 (6.4 g, 33°/.). Compound (^4-3) will be prepared as compound C-4~2 (4.9 g, 24.4 with 〇1), 2,4-dichloroquinazoline (6·4 S, 22.2 mnml), Pd(PPh3)4 (11 g, 2 5 颜(4) and MO^7·1 g' 66.6 咖. 1) Dissolved in a solution of stupid (30G mL) and distilled water (75 after the reaction mixture was given in the 9th generation for 2 hours) The organic layer obtained by reduction under reduced pressure was then ground with MeQH. The solution of the capsule was solved in mc and passed through; the gel transition, followed by grinding with MC and the same to obtain compound C-4-3 (4.1 g, 45%) Preparation of β compound C-20 After compound C+3 (4.5 g, 10.9 mraQl) and compound ch (4.1 g, 9, 9 mmol) were suspended in DMF 80 mL, 6 at room temperature 〇% Ν&Η «Μ mg, 14. 8 mmol) was added to the mixture. The resulting reaction mixture was stirred for 12 hours. After adding purified water (1 L), the mixture was filtered under reduced pressure. /Ethyl acetate was ground together' and then ground with DMF, followed by grinding with EA/THF. The obtained solid was dissolved in MC, 95566 25 201249960 was filtered through a gelatinous gel, followed by grinding with MeOH/EA to obtain compound C. -20 (3. 4 g, 44 %) The MS/FAB measurement was 779; the calculated value was 778. 9 制备 Preparation 5 · Preparation of Compound C-21
化合物C-5-1之製備 將二苯并[b，d]嘆吩-4-基蝴酸（2〇 g，87 7咖〇1)、 漠苯（18.4H1L，175_l)、Pd(PPh3)4(2 9g，2 5_υ 及 Na2C〇3(23.2 g，219 mmol)溶解於甲苯（375mL)、Et〇H (75mL)與蒸德水（75mL)之混合物中後’將該反應混合物於 90°C攪拌4小時。於減壓下蒸餾所獲有機層，隨後以MC 及己烷透過管柱過濾以獲得化合物〇5_1(17 g，75%)。 化合物C-5-2之製備 將化合物 C-5-1 (17 g, 65. 3 mmol)溶解於（THF(500 mL) 中之後’於-78°C將2. 5Mn-BuLi之己烷溶液（52.2mL，130 顏〇1)加入該反應混合物中，攪拌該反應混合物1小時。伴 隨攪拌該反應混合物2小時’同時將B(0i-Pr)3(21.8mL， 195 mmol)緩慢加入該反應混合物中。加入2M HC1粹滅反 應混合物之後，以蒸餾水及EA萃取反應混合物。以MC及 己烷再結晶所得固體以獲得化合物C-5-2 (11. 5 g，60%)。 化合物C-5-3之製備 95566 26 201249960 將化合物c_5_2(8. 3 g，41.5舰Μ)、〗，*—二氯喹唑 琳（11. 5 g’ 37. 8 mmol)、Pd(PPh3)4(2. 2 g，2. 5 mmol)及 ^2〇)3(12 g’ il3匪〇1)溶解於曱苯（3〇〇mL)與蒸餾水（75此) 之此合物中之後，將該反應混合物於9(TC攪拌2小時。於 減壓下瘵餾所獲有機層，隨後與MeOH —起研磨。將所得固 體〉谷解於MC中’透過矽膠過濾，隨後與MC與己烷一起研 磨以獲得化合物05-3(10 g，68%)。 化合物C-21之製備Preparation of compound C-5-1 will be dibenzo[b,d]-indol-4-ylfolic acid (2〇g, 87 7 curry 1), desert benzene (18.4H1L, 175_l), Pd (PPh3) 4(2 9g, 2 5_υ and Na2C〇3 (23.2 g, 219 mmol) were dissolved in a mixture of toluene (375 mL), EtH (75 mL) and distilled water (75 mL). The mixture was stirred for 4 hours. The obtained organic layer was evaporated under reduced pressure, and then filtered through a column of MC and hexane to obtain compound 〇5_1 (17 g, 75%). Preparation of Compound C-5-2 Compound C- 5-1 (17 g, 65. 3 mmol) was dissolved in THF (500 mL). A solution of 2.5 Mn-BuLi in hexane (52.2 mL, 130 〇1) was added to the reaction at -78 °C. In the mixture, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours while B (0i-Pr) 3 (21.8 mL, 195 mmol) was slowly added to the reaction mixture. After the 2M HCl was quenched, The reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized from MC and hexane to afford compound C-5-2 (11.5 g, 60%). Preparation of Compound C-5-3 95566 26 201249960 Compound c_5_2 ( 8. 3 g, 41.5 ship)), , *-dichloroquinazoline (11. 5 g' 37. 8 mmol), Pd (PPh3) 4 (2.2 g, 2.5 mmol) and ^2〇) 3 (12 g' il3匪〇1) After dissolving in this mixture of toluene (3 〇〇mL) and distilled water (75%), the reaction mixture was stirred at 9 (TC for 2 hours. The organic layer was obtained by distillation under reduced pressure, followed by MeOH. Grinding was carried out. The obtained solid was dissolved in MC and filtered through a silica gel, followed by grinding with MC and hexane to obtain Compound 05-3 (10 g, 68%). Preparation of Compound C-21
將化合物 C-5-3(5 g，11. 8 mmol)與化合物 C-1-1 (4. 8 δ’ 11. & mmol)懸浮於DMF 80mL中之後，於室溫將60% NaH mg，22 mmol)加入該混合物中。攪拌所得反應混合物 12小時。加入純化水uL)後，於減壓下過濾該混合物。將 所得固體與MeOH/乙酸乙酯一起研磨，之後與DMF —起研 磨，隨後與EA/THF —起研磨。將所得固體溶解於MC中， 透過矽膠過濾，隨後與MeOH/EA —起研磨以獲得化合物 c一21(4. 8 g，51%)。 MS/FAB測量值為795 ;計算值為794. 96 製備例6 :化合物C-33之製備After compound C-5-3 (5 g, 11.8 mmol) and compound C-1-1 (4.8 δ' 11. & mmol) were suspended in DMF 80 mL, 60% NaH mg at room temperature , 22 mmol) was added to the mixture. The resulting reaction mixture was stirred for 12 hours. After adding purified water uL), the mixture was filtered under reduced pressure. The resulting solid was triturated with MeOH / ethyl acetate then triturated with DMF and then triturated with EA / THF. The obtained solid was dissolved in MC, filtered through silica gel, and then triturated with MeOH/EA to afford compound c- 21 (4.8 g, 51%). MS/FAB measurement was 795; calculated 794. 96 Preparation 6: Preparation of compound C-33
化合物C-6-1之製備 95566 27 201249960 將一^本并[b，d]n夫喃-4-基棚酸（20 g，94. 34 mmol)、 卜溴-4-蛾-苯（53. 4 ml，188. 68 mmol)、Pd(PPh3)4(5. 45 g， 4.72 mmol)及 K2C〇3(39，l g，283. 01 mmol)溶解於甲苯 (900mL)、EtOH(200mL)與蒸鶴水（2〇〇mL)之混合物中之後， 將該反應混合物於70至8(TC攪拌3小時。終止反應後， 藉由重力分離而自該混合物移除水層。隨後，將所得有機 層濃縮並透過管柱純化以獲得化合物C-6-l(17 g，56 %)。 化合物C-6-2之製備 將化合物 C-6-1 (17 g，52. 6 mmol)溶解於中 THF (400 1111〇之後，於_78〇將2.5河11-3111^之己烧溶液（31.5 1111, 78. 9 mmol)加入該反應混合物中，擾拌該反應混合物1小 時。將反應混合物攪拌12小時，同時wB(〇i_Pr)3(24.丨ml， 10 5. 2 imo 1)緩‘fe加入該反應混合物中。終止反應後，將純 化水20 mL緩慢加入該反應混合物中。以ea/nh4C1水溶液 卒取该反應混合物。濃縮所得有機層，與MC/己烧一起研 磨，隨後過濾以獲得化合物C-6-2 5 g 96%)。 化合物C-6-3之製備Preparation of Compound C-6-1 95566 27 201249960 A benzo[b,d]n-fol-4-yl succinic acid (20 g, 94.34 mmol), bromo-4-moth-benzene (53) 4 ml, 188. 68 mmol), Pd(PPh3)4 (5. 45 g, 4.72 mmol) and K2C〇3 (39, lg, 283.1 mmol) dissolved in toluene (900 mL), EtOH (200 mL) After distilling the mixture of crane water (2 〇〇 mL), the reaction mixture was stirred at 70 to 8 (TC for 3 hours. After the reaction was terminated, the aqueous layer was removed from the mixture by gravity separation. Subsequently, the obtained organic layer was obtained. Concentrate and purify through a column to obtain compound C-6-1 (17 g, 56%). Preparation of Compound C-6-2 Compound C-6-1 (17 g, 52.6 mmol) was dissolved in THF (After 400 1111 Torr, 2.5 liters of 11-3111 hexane solution (31.5 1111, 78. 9 mmol) was added to the reaction mixture at _78 Torr, and the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 12 hours. At the same time, wB(〇i_Pr)3 (24.丨ml, 10 5. 2 imo 1) was added to the reaction mixture. After the reaction was terminated, 20 mL of purified water was slowly added to the reaction mixture to ea/nh4C1. The aqueous mixture is drawn to the reaction mixture. The organic layer was obtained by trituration with MC/hexane, followed by filtration to obtain Compound C-6-2 5 g 96%). Preparation of Compound C-6-3
將化合物 06-2(4. 5 g，50. 33 mmol)、2, 4-二氣啥唾 ^(11.5 g, 50.33 nin,ol)^Na2C〇3(20.9 g, 150.99 mmol) 及 Pd(PPh3)4(2. 9 g，2· 52 πιιηοΐ)溶解於曱笨（go。此）、Et〇H (75 mL)及蒸潑水（75 mL)之/¾合物中後，於75至授 拌該反應混合物12小m反應後’將該反應混合物冷 部至室溫’藉由重力分離而自該混合物移除水層。濃縮所 得有機層，與THF/MeOH -起研磨，過濾、’隨後乾燥。將經 95566 28 201249960 乾燥之化合物溶解於氯仿3L中，透過矽膠過濾。濃縮剩餘 溶液並與EA —起研磨以獲得化合物C-6-3 (3. 8 g，19 %)。 化合物C-33之製備 將化合物 8 g，9.34 mmol)與化合物 C-6-3 (3. 8 g，9. 34 mmol)懸浮於DMF 80 mL中之後，於室溫將 60% NaH(l· 12 g，28. 02 mL)加入該混合物中。攪拌所得反 應混合物12小時。加入純化水（il)後，於減壓下過濾該 混合物。將所得固體與Me〇H/乙酸乙酯一起研磨，之後與 DMF 一起研磨’隨後與EA/THF —起研磨。將所得固體溶解 於MC中’透過矽膠過濾，隨後與MeOH/EA —起研磨以獲得 化合物 C-33(2. 9 g，40 %)。 MS/FAB測量值為779 ;計算值為778. 90 製備例7 :化合物C-34之製備Compound 06-2 (4.5 g, 50.33 mmol), 2, 4-dioxapyrene (11.5 g, 50.33 nin, ol)^Na2C〇3 (20.9 g, 150.99 mmol) and Pd (PPh3) 4(2. 9 g, 2· 52 πιιηοΐ) dissolved in 曱 ( (go.), Et 〇 H (75 mL) and steamed water (75 mL) in /3⁄4 compound, after 75 to mix The reaction mixture was subjected to a reaction of 12 m after the reaction of the reaction mixture to a room temperature to remove the aqueous layer from the mixture by gravity separation. The resulting organic layer was concentrated, triturated with THF / MeOH - filtered, then dried. The dried compound of 95566 28 201249960 was dissolved in 3 L of chloroform and filtered through silica gel. The remaining solution was concentrated and triturated with EA to give compound C-6-3 (3.8 g, 19%). Preparation of Compound C-33 After compound 8 g, 9.34 mmol) and compound C-6-3 (3.8 g, 9.34 mmol) were suspended in DMF 80 mL, 60% NaH (l· at room temperature) 12 g, 28.02 mL) was added to the mixture. The resulting reaction mixture was stirred for 12 hours. After adding purified water (il), the mixture was filtered under reduced pressure. The resulting solid was triturated with Me〇H/ethyl acetate, then triturated with DMF and then triturated with EA/THF. The obtained solid was dissolved in MC to be filtered through EtOAc, and then triturated with MeOH/EA to obtain Compound C-33 (2.9 g, 40%). MS/FAB measured 779; calculated 778. 90 Preparation 7: Preparation of compound C-34
化合物C-7-1之製備Preparation of Compound C-7-1
於2000 mL圓底燒瓶中，將卜溴-4-碘-笨（49.6 g， 〇· 17mol)、二苯并[b，d]噻吩-4-基硼酸（20g，0.087 mol)、 Pd(PPh3)4 (5. 0 g，〇. 044 mol)及 Na2C〇3 (18. 5 g, 0. 18 mol) 办解於曱苯（880 mL)與h2〇 (200 mL)之混合物中後，於80°C 搜摔該反應混合物12小時。終止反應後，以乙酸乙酯萃取 95566 29 201249960 反應混合物。隨後，以MgS〇4乾燥所得有機層並過濾。於 減壓下自該有機層移除溶劑，透過吸附管柱過濾該有機層 以獲得白色固體化合物C-7-1 (21.2 g，71 %)。 化合物C-7-2之製備 於無水條件下將化合物07-1(21.4 g，〇.〇6 mol)及 乾THF(1000 mL)放入2000 mL圓底燒瓶中後，於_78°C將 n-BuLi之己烷溶液（37 mL，2.25 Μ溶液）緩慢加入該反應 混合物中，同時於氮氣氛下攪拌該混合物。於-78°C攪拌該 反應混合物 1 小時。於-78°C 將 B(0i_PrM29 mL，0. 13 mol) 緩慢加入該反應混合物中後，將反應混合物加熱至室溫並 反應12小時。終止反應後，以乙酸乙酯萃取反應混合物。 隨後，以MgS〇4乾燥所得有機層並過濾。於減壓下自有機 層移除溶劑後，透過管柱過濾該有機層以獲得白色固體化 合物 C-7-2(15. 5 g，81 %)。 化合物C-7-3之製備 於250 mL圓底燒瓶中，將化合物C-7-2 (15. 5 g，0. 051 111〇1)、2,4-二氯喹唑啉（12.2舀，0.06 111〇1)、仙2(：03(16.2 g，0.153 mol)及 Pd(PPh3)4(2· 94 g，0.0025 mol)加入甲 苯（250 mL)、EtOH(40 mL)及 H2〇(70 mL)之混合物中後， 於80°C攪拌該反應混合物12小時。終止反應後，以乙酸 乙酯萃取反應混合物。隨後，以MgS〇4乾燥所得有機層並 過濾。於減壓下自有機層移除溶劑後，再結晶所得固體以 獲得化合物07-3(14 g，65%)。 化合物C-34之製備 95566 30 201249960 於無水條件下將 NaH 60%(0. 62 g，〇. 0154 mol)與 DMF (60mL)放入250 mL圓底燒瓶中。將化合物C-l-1 (4. 83g， 0. 012 mol)溶解於DMF(3G mL)中之後’將該混合物放入該 圓底燒瓶中。攪拌反應混合物1小時。將化合物c_7_3 (5 g，0.012 mol)溶解於DMF(30 mL)中之後’將該混合物放 入該圓底燒瓶中。攪拌該混合物12小時後，過濾黃色固 體’以MeOH洗滌，與THF —起研磨，隨後與一起研磨 以獲得化合物C-34(4. 2g，45%)。 MS/FAB測量值為795 ;計算值為794. 96 製備例8 ··化合物C-36之製備In a 2000 mL round bottom flask, bromo-4-iodo-stupid (49.6 g, 〇17 mol), dibenzo[b,d]thiophen-4-ylboronic acid (20 g, 0.087 mol), Pd (PPh3) 4 (5. 0 g, 〇. 044 mol) and Na2C〇3 (18. 5 g, 0. 18 mol) after the mixture of benzene (880 mL) and h2 〇 (200 mL), The reaction mixture was searched at 80 ° C for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate 95566 29 2012499. Subsequently, the resulting organic layer was dried with MgS 4 and filtered. The solvent was removed from the organic layer under reduced pressure, and the organic layer was filtered through a column to obtain white solid compound C-7-1 (21.2 g, 71%). Preparation of Compound C-7-2 After compound 07-1 (21.4 g, 〇.〇6 mol) and dry THF (1000 mL) were placed in a 2000 mL round bottom flask under anhydrous conditions, at _78 ° C A n-BuLi hexane solution (37 mL, 2.25 hydrazine solution) was slowly added to the reaction mixture while stirring the mixture under a nitrogen atmosphere. The reaction mixture was stirred at -78 °C for 1 hour. After B (0i_PrM29 mL, 0.13 mol) was slowly added to the reaction mixture at -78 °C, the reaction mixture was heated to room temperature and reacted for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. Subsequently, the resulting organic layer was dried with MgS 4 and filtered. After removing the solvent from the organic layer under reduced pressure, the organic layer was filtered through column to afford white solid compound C-7-2 (15. 5 g, 81%). Preparation of compound C-7-3 in a 250 mL round bottom flask, compound C-7-2 (15.5 g, 0.051 111 〇1), 2,4-dichloroquinazoline (12.2 舀, 0.06) 111〇1), Xian 2(:03 (16.2 g, 0.153 mol) and Pd(PPh3)4 (2·94 g, 0.0025 mol) were added toluene (250 mL), EtOH (40 mL) and H2 (70 mL) After the mixture was stirred, the reaction mixture was stirred at 80 ° C for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. Then the organic layer was dried with MgSO 4 and filtered. After removal of the solvent, the obtained solid was recrystallized to give compound 07-3 (14 g, 65%). Preparation of Compound C-34 95566 30 201249960 NaH 60% (0. 62 g, 〇. 0154 mol) under anhydrous conditions The mixture was placed in a 250 mL round bottom flask with DMF (60 mL). After the compound Cl-1 (4.83 g, 0. 012 mol) was dissolved in DMF (3G mL), the mixture was placed in the round bottom flask. The reaction mixture was stirred for 1 hour. After compound c_7_3 (5 g, 0.012 mol) was dissolved in DMF (30 mL), the mixture was placed in the round bottom flask. After stirring the mixture for 12 hours, the yellow solid was filtered. Trituration, trituration with THF, followed by trituration to obtain compound C-34 (4.2 g, 45%). MS/FAB measured 795. Calculated value 794. 96 Preparation Example 8 · Compound C-36 Preparation
將二苯并[b，d]°夫嗔-4-基棚酸（20 g, 94. 34 mmol)、 1，3-二溴苯（22.3轻，94.34 _〇1)、？(1(??113)4(5.45运，4.72 mmol)及 K2C〇3(39· 1 g，283.01 mmol)溶解於甲苯（8〇〇mL)、 EtOH(200 mL)及蒸顧水（200 mL)之混合物中後，於70至 80°C攪拌反應混合物3小時。終止反應後，藉由重力分離 而自該混合物移除水層。隨後，濃縮所得有.機層並透過矽 膠管柱純化以獲得化合物C-8-K13 g，43%)。 化合物C-8-2之製備 95566 31 201249960 將化合物 08-1 (13 g，40. 23 mmol)溶解於 THF (300 mL)中之後，於-78°C將2.5M n-BuLi之己烷溶液（19 ml, 48.27 mmol)加入該反應混合物中，攪拌該反應混合物i 小時。授拌反應混合物12小時，同時將B(〇i—pr)3 (13. 9 raL，60.34 ramol)緩慢加入該反應混合物中。終止反應後， 將純化水20 mL緩慢滴加至該反應混合物。以ea/nh4C1水 溶液萃取反應混合物。濃縮所得有機層，與己烷一起 研磨，隨後過遽以獲得化合物C-8-2(6. 8 g, 58. 7 。 化合物C-8-3之製備 將化合物 C-8-2(6. 8 g，23. 6 mmol)、2, 4-二氯喹唑啉 (5.38g，23. 6mmol)、Na2C〇3(9. 8g，70.8mmol)&Pd(PPh3)4 (1.36 g，1.18 mmol)溶解於甲苯（24〇mL)與蒸餾水（5〇此） 之混合物中後’於90至100¾攪拌該反應混合物12小時。 終止反應後，將反應混合物冷卻至室溫，藉由重力分離而 自4混合物移除水層。濃縮所得有機層，與THF/Me〇H 一起 研磨、’過濾，隨後乾燥。將乾燥之化合物溶解於氯仿3 L· 中，並透過矽膠過濾。濃縮剩餘溶液並與THF/MeOH —起研 磨以獲得化合物C-8-3(3. 8g，40%)。 化合物C-36之製備 將化合物 C-1-1 (3.8 g，9.34 mmol)與化合物 c-8-3 (3· 8 g’ 9. 34 mmol)懸浮於DMF 80 mL中後，於室溫將Dibenzo[b,d]°fusin-4-yl benzoic acid (20 g, 94.34 mmol), 1,3-dibromobenzene (22.3 light, 94.34 _〇1), ? (1(??113)4(5.45 transport, 4.72 mmol) and K2C〇3 (39·1 g,283.01 mmol) dissolved in toluene (8〇〇mL), EtOH (200 mL) and steamed water (200 mL) After the mixture was stirred, the reaction mixture was stirred at 70 to 80 ° C for 3 hours. After the reaction was terminated, the aqueous layer was removed from the mixture by gravity separation. Subsequently, the obtained organic layer was concentrated and purified through a silica gel column. Compound C-8-K13 g, 43%) was obtained. Preparation of Compound C-8-2 95566 31 201249960 After dissolving Compound 08-1 (13 g, 40.23 mmol) in THF (300 mL), 2.5 M n-BuLi in hexanes at -78 ° C (19 ml, 48.27 mmol) was added to the reaction mixture and the mixture was stirred for one hour. The reaction mixture was stirred for 12 hours while B (〇i-pr) 3 (13.9 raL, 60.34 ramol) was slowly added to the reaction mixture. After the reaction was terminated, 20 mL of purified water was slowly added dropwise to the reaction mixture. The reaction mixture was extracted with an ea/nh4C1 aqueous solution. The obtained organic layer was concentrated, triturated with hexane, and then purified to afford compound C-8-2 (6. 8 g, 58. 7. Preparation of compound C-8-3 Compound C-8-2 (6. 8 g, 23.6 mmol, 2, 4-dichloroquinazoline (5.38 g, 23.6 mmol), Na2C〇3 (9.8 g, 70.8 mmol) & Pd(PPh3)4 (1.36 g, 1.18 mmol) After dissolving in a mixture of toluene (24 〇mL) and distilled water (5 〇), the reaction mixture was stirred at 90 to 1003⁄4 for 12 hours. After the reaction was terminated, the reaction mixture was cooled to room temperature and separated by gravity. 4 The aqueous layer was removed from the mixture. The obtained organic layer was concentrated, triturated with THF/Me EtOAc, filtered, and then dried. The dried compound was dissolved in chloroform 3 L· and filtered through silica gel. /MeOH - trituration to obtain compound C-8-3 (3.8 g, 40%). Preparation of compound C-36 Compound C-1-1 (3.8 g, 9.34 mmol) and compound c-8-3 ( 3· 8 g' 9. 34 mmol) after suspension in DMF 80 mL, at room temperature
NaH (1·12 g，28. 02 mL)加入該混合物中。授拌所得反應 此δ物12小時。加入純化水（丨L)之後，於減壓下過濾該混 合物。將所得固體與Me〇H/乙酸乙酯一起研磨，溶解於MC 95566 32 201249960 中，透過矽膠過濾，隨後與MC/正己烷一起研磨以獲得化 合物 C-36(l. 6 g，21%)。 MS/FAB測量值為779 ;計算值為778. 90 製備例9 :化合物C-37之製備NaH (1·12 g, 28.02 mL) was added to the mixture. The resulting reaction was stirred for 12 hours. After adding purified water (丨L), the mixture was filtered under reduced pressure. The resulting solid was triturated with EtOAc / EtOAc (EtOAc)EtOAc. MS/FAB measured 779; calculated 778. 90 Preparation 9: Preparation of compound C-37
於2000 mL圓底燒瓶中，將1，3-二漠苯（16. 5 g，0. 2 mol)、二苯并[b, d]D塞吩-4-基侧酸（15 g, 0.06 mol)、 Pd(PPh3)4(3.8 g，0.003 mol)及 Na2C〇3(14 g，0.13 mol) 溶解於曱苯（330 mL)與H2〇 (70 mL)之混合物中後，於80°C 攪拌反應混合物12小時。終止反應後，以乙酸乙酯萃取反 應混合物。隨後，以1^8〇4乾燥所得有機層並過濾。於減 壓下自該有機層移除溶劑後，透過管柱過濾該有機層以獲 得白色固體化合物C-9-l(8.4g，40%)。 化合物C-9-2之製備 於無水條件下將化合物C-9-l(8.4 g，0.025 mol)與 乾THF(200 mL)放入500 mL圓底燒瓶中後，於-78°C將 n-BuLi之己烧溶液（15 mL, 2.25 Μ溶液）緩慢加入該反應 混合物中，同時於氮氣氛下攪拌該混合物。於-78°C攪拌反 應混合物 1 小時。於-78°C 將 B(0i-Pr)3 (11.4 mL, 0. 05 mol) 95566 33 201249960 緩慢加入該反應混合物中後，將反應混合物加熱至室溫並 反應12小時。終止反應後，以乙酸乙酯萃取反應混合物。 隨後’以MgS〇4乾燥所得有機層並過濾。於減壓下自有機 層移除溶劑後，透過管柱過濾該有機層以獲得白色固體化 合物 C-9-2(6 g，80 %)。 化合物C-9-3之製備In a 2000 mL round bottom flask, 1,3-dioxabenzene (16.5 g, 0.2 mol), dibenzo[b, d]D-cephen-4-yl acid (15 g, 0.06) Mol), Pd(PPh3)4 (3.8 g, 0.003 mol) and Na2C〇3 (14 g, 0.13 mol) dissolved in a mixture of toluene (330 mL) and H2 (70 mL) at 80 ° C The reaction mixture was stirred for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. Subsequently, the resulting organic layer was dried at 1^8 〇4 and filtered. After removing the solvent from the organic layer under reduced pressure, the organic layer was filtered through a column to afford white solid compound C-9-1 (8.4 g, 40%). Preparation of Compound C-9-2 After compound C-9-1 (8.4 g, 0.025 mol) and dry THF (200 mL) were placed in a 500 mL round bottom flask under anhydrous conditions, n at -78 ° C A solution of -BuLi hexane (15 mL, 2.25 hydrazine solution) was slowly added to the reaction mixture while stirring the mixture under a nitrogen atmosphere. The reaction mixture was stirred at -78 ° C for 1 hour. After B (0i-Pr) 3 (11.4 mL, 0.05 mol) 95566 33 201249960 was slowly added to the reaction mixture at -78 ° C, the reaction mixture was heated to room temperature and reacted for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. The resulting organic layer was then dried with MgS 4 and filtered. After removing the solvent from the organic layer under reduced pressure, the organic layer was filtered through a column to obtain a white solid compound C-9-2 (6 g, 80%). Preparation of Compound C-9-3
於250 mL圆底燒瓶中，將化合物c-9-2 (5. 9 g，0. 02 mol)、2, 4-二氣喹唑啉（4· 6 g，0· 02 mol)、Na2C〇3(6· 2 g， 0.058 mol)及 Pd(PPh3)4(l.l g，0.00097 m〇i)加入曱苯 (100mL)、EtOH (14mL)及 H2〇 (30mL)之混合物中後，於 70°C 攪拌該反應混合物3小時。反應終止後，以乙酸乙酯萃取 反應混合物。隨後’以MgS〇4乾燥所得有機層並過濾。於 減麗下自有機層移除溶劑後，透過管柱過濾該有機層以獲 得化合物 C-9-3(7. 0g, 85%)。 化合物C-37之製備 於無水條件下將NaH 60%(0.5 g，0.013 mol)與DMF (40 mL)放入250 mL圓底燒瓶中。將化合物7 g， 〇‘ 009 mol)溶解於DMF(30 mL)中之後，將該混合物放入該 圓底燒瓶中。攪拌反應混合物1小時。將化合物C_9_3 (4 g，0.G095 mol)溶解於DMF(3〇 mL)中之後，將該混合物放 入該圓底燒瓶中。攪拌混合物12小時後，過濾黃色固體， 以MeOH洗滌，與THF —起研磨，隨後與DMF 一起研磨以獲 得化合物 037(1. 7 g，20%)。 MS/FAB測量值為795 ;計算值為794. 96 95566 34 201249960 製備例10 :化合物C-39之製備In a 250 mL round bottom flask, compound c-9-2 (5.9 g, 0.02 mol), 2,4-dioxaquinazoline (4.6 g, 0.02 mol), Na2C〇 3 (6·2 g, 0.058 mol) and Pd(PPh3)4 (ll g, 0.00097 m〇i) were added to a mixture of toluene (100 mL), EtOH (14 mL) and H2 (30 mL) at 70°. C The reaction mixture was stirred for 3 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. The resulting organic layer was then dried with MgS 4 and filtered. After the solvent was removed from the organic layer, the organic layer was filtered through a column to afford compound C-9-3 (7.0 g, 85%). Preparation of Compound C-37 NaH 60% (0.5 g, 0.013 mol) and DMF (40 mL) were placed in a 250 mL round bottom flask under anhydrous conditions. After dissolving the compound 7 g, 〇 '009 mol, in DMF (30 mL), the mixture was placed in the round bottom flask. The reaction mixture was stirred for 1 hour. After dissolving Compound C_9_3 (4 g, 0. G095 mol) in DMF (3 mL), the mixture was placed in the round bottom flask. After the mixture was stirred for 12 hours, a yellow solid was filtered, washed with MeOH, EtOAc EtOAc (EtOAc) MS/FAB measurement was 795; calculated 794. 96 95566 34 201249960 Preparation 10: Preparation of compound C-39
化合物C-10-1之製備 將化合物C-1-1 (14 2，34. 3则1〇1)與1-溴-4-碘苯 (48.5g, 171. 4 ramol)'CuI(3. 3 g, 17. 1 mmol)' K3P〇4 (21. 8 g，102. 9 mmol)及伸乙二胺（EDA)(2,3 mL, 34. 3 mmol)放 入曱苯（500 mL)中後，於回流下攪拌該反應混合物1天？ 以EA萃取反應混合物，於減壓下蒸餾，隨後以MC/己烷透 過管柱過遽以獲得化合物C_l〇_l(15. 5 g, 80. 1%)。 化合物C-10-2之製備 將化合物 C-10-l(15. 5 g，27· 5 mmol)溶解於 THF (250 mL)中之後，於-78°C將2. 5 M n-BuLi之己烧溶液（17. 6 mL， 44 mmol)加入該反應混合物中，攪拌反應混合物1小時。 伴隨攪拌反應混合物2小時’同時將B(〇i-Pr)3 (12. 6 raL， 55 mmol)緩慢加入該反應混合物中。加入2M HC1粹滅反應 混合物後，以蒸餾水及EA萃取反應混合物。以MC及己烷 再結晶所得固體以獲得化合物C-10-2(8.7 g，60°/。）。 化合物C-39之製備 將化合物〇3_l(3. 2 g，9.2細1〇1)、化合物C-10-2 (4.9g，9. 2mmol)、Pd(PPh3)4(532 mg，〇.46minol)&Na2C〇3 (2.9 g，27·6 mmol)溶解於甲苯（55 mL)、Et0H(14 mL)及 95566 35 201249960 蒸餾水（14 mL)之混合物中後，於90t：攪拌反應混合物2 小時。以蒸飽水及EA萃取反應混合物，隨後以mc及己烧 透過管柱過濾以獲得化合物C-39(5. 5g，75%)。 MS/FAB測量值為795 ;計算值為794. 96 製備例11 :化合物C-40之製備Preparation of Compound C-10-1 Compound C-1-1 (14 2,34. 3 〇1) and 1-bromo-4-iodobenzene (48.5 g, 171.4 molol) 'CuI (3. 3 g, 17. 1 mmol) 'K3P〇4 (21. 8 g, 102.9 mmol) and ethylenediamine (EDA) (2,3 mL, 34.3 mmol) in benzene (500 mL) After the middle, the reaction mixture was stirred under reflux for 1 day? The reaction mixture was extracted with EtOAc, EtOAc (EtOAc m.) The preparation of the compound C-10-2, after dissolving the compound C-10-l (15. 5 g, 27.5 mmol) in THF (250 mL), at -78 ° C, 2. 5 M n-BuLi A hexane solution (17.6 mL, 44 mmol) was added to the reaction mixture and the mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours while B (〇i-Pr) 3 (12.6 raL, 55 mmol) was slowly added to the reaction mixture. After the 2M HCl purged mixture was added, the reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized from MC and hexane to obtain Compound C-10-2 (8.7 g, 60%). Preparation of Compound C-39 The compound 〇3_l (3.2 g, 9.2 fine 1〇1), compound C-10-2 (4.9 g, 9.2 mmol), Pd(PPh3)4 (532 mg, 〇.46minol ) &Na2C〇3 (2.9 g, 27·6 mmol) was dissolved in a mixture of toluene (55 mL), Et0H (14 mL) and 95566 35 201249960 distilled water (14 mL). . The reaction mixture was extracted with EtOAc (EtOAc) EtOAc (EtOAc). MS/FAB measured 795; calculated 794. 96 Preparation 11: Preparation of compound C-40
化合物C-40之製備 將化合物 C-2-l(3.2 g，9.2 mmol)、化合物 C-10-2 (4.9g，9. 2mmol)、Pd(PPh3)4(532 mg，0.46mmol)&NazC〇3 (2. 9 g，27. 6 _ol)溶解於曱笨（55 mL)、EtOH(14 mL)及 蒸餾水（14 mL)之混合物中後，於9〇°c攪拌反應混合物2 小時。以蒸餾水及EA萃取反應混合物，以MC及己烷透過 管柱過濾以獲得化合物C-40 (5.5 g，75 %)。 MS/FAB測量值為779 ;計算值為778. 90 實施例1 :使用根據本發明之化合物製造0LED裝置 使用根據本發明之化合物製造了 〇LED裝置。以三氯 乙稀·、丙酮、乙醇及蒸鶴水依序使用超音波洗條於有機發 光二極體（0LED)裝置用玻璃基板上之透明電極氧化銦錫 (IT0)薄膜（15 Q/sq)(Samsung Corning，Republic of Korea)，隨後存儲於異丙醇中。隨後，將該ITO基板裝備 於真空氣相沉積設備之基板炎持器上。將Ν1-(萘-2-基）-95566 36 201249960 糾，财-雙（4-(萘-2-基（苯基）胺基）苯基）-則-苯基苯-1，4-二胺引入該真空氣相沉積設備之一小室中，隨後將該設備 之該腔之壓力控制為1(Γ6托（torr)。之後，對該小室施以 電流以揮發上述引入之材料，從而於該ΙΤ0基板上形成厚 度為60奈米（nm)之電洞注入層。隨後，將Ν，Ν’ -二（4-聯 苯）-Ν，Ν’ -二（4-聯苯）-4, 4’ -二胺基聯苯引入該真空氣相 沉積設備之另一小室中，藉由施用電流至該小室而揮發之， 從而於該電洞注入層上形成厚度為20 nm之電洞傳輸層。 之後，將化合物C-2引入該真空氣相沉積設備之一小室中 作為主體材料，將化合物D-11引入另一小室中作為摻雜劑。 以不同速率揮發兩種材料，並以4至20wt%之摻雜量沉積 以於該電洞傳輸層上形成厚度為30 nm之發光層。隨後， 將9, 10-二（1-萘基）-2-(4-苯基-1-苯基-1H-苯并[d]咪唑） 蒽引入一小室中並將8-經基啥琳鋰（1 ithium quinolate)引 入另一小室中。以不同速率揮發兩種材料，並以30至70wt% 摻雜量沉積以於該發光層上形成厚度為30 nm之電子傳輸 層。隨後，於該電子傳輸層上沉積厚度為1至2 nm之8-羥基喹啉鋰作為電子注入層之後，藉由另一真空氣相沉積 設備於該電子注入層上沉積厚度為150 nm之鋁（A1)陰極。 由是，製造0LED裝置。用於製造該0LED裝置之全部材料 係彼等藉由在1(T6 torr真空昇華而純化者。 所製造之0LED裝置顯示，驅動電壓為4. 0伏特(V)時， 照度為1，020 cd/m2之紅色發光，電流密度為14. 0 mA/cm2。 再者，對於5, 000尼特（nit)之照度而言，該照度降低至其 95566 37 201249960 9〇%所耗之最短時faU6G小時。 實施例2至11 :使 以膏祐似！ 據本發明之化合物製造0LED裝置 中顯㈣ 作為主體材料及摻雜劑。Preparation of Compound C-40 Compound C-2-1 (3.2 g, 9.2 mmol), Compound C-10-2 (4.9 g, 9.2 mmol), Pd(PPh3)4 (532 mg, 0.46 mmol) & NazC〇3 (2.9 g, 27.6 _ol) was dissolved in a mixture of EtOAc (EtOAc) (EtOAc) (EtOAc) The reaction mixture was extracted with distilled water and EA, and then filtered, and then filtered through silica gel to afford compound C-40 (5.5 g, 75%). The MS/FAB measurement was 779; the calculated value was 778. 90. Example 1: Manufacture of an OLED device using the compound according to the present invention A ruthenium LED device was fabricated using the compound according to the present invention. Transparent electrode indium tin oxide (IT0) film (15 Q/sq) on a glass substrate for organic light-emitting diode (0LED) device using ultrasonic cleaning with trichloroethylene, acetone, ethanol and steamed crane water (Samsung Corning, Republic of Korea), then stored in isopropanol. Subsequently, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Ν1-(naphthalen-2-yl)-95566 36 201249960 ,,财-双(4-(naphthalen-2-yl(phenyl)amino)phenyl)--phenylbenzene-1,4-di An amine is introduced into one of the chambers of the vacuum vapor deposition apparatus, and then the pressure of the chamber of the apparatus is controlled to 1 (Γ6 torr). Thereafter, the chamber is subjected to an electric current to volatilize the introduced material, thereby A hole injection layer having a thickness of 60 nm is formed on the substrate of ΙΤ0. Subsequently, Ν, Ν'-bis(4-biphenyl)-Ν, Ν'-bis(4-biphenyl)-4, 4 '-Diaminobiphenyl is introduced into another chamber of the vacuum vapor deposition apparatus, and is volatilized by applying a current to the chamber to form a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, Compound C-2 was introduced into one of the chambers of the vacuum vapor deposition apparatus as a host material, and Compound D-11 was introduced into another chamber as a dopant. The two materials were volatilized at different rates and were 4 to 20 wt. A doping amount of % is deposited to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Subsequently, 9, 10-bis(1-naphthyl)-2-(4-phenyl-1-phenyl) -1H- And [d]imidazole) is introduced into a small chamber and introduced into another chamber by 8-ionium quinolate. The two materials are volatilized at different rates and deposited at a doping amount of 30 to 70 wt%. An electron transport layer having a thickness of 30 nm is formed on the light-emitting layer. Subsequently, lithium 8-hydroxyquinolate having a thickness of 1 to 2 nm is deposited on the electron transport layer as an electron injection layer, and another vacuum gas phase is used. A deposition apparatus deposits an aluminum (A1) cathode having a thickness of 150 nm on the electron injecting layer. Thus, an OLED device is fabricated. All of the materials used to fabricate the OLED device are purified by 1 (T6 torr vacuum sublimation) The OLED device manufactured shows that when the driving voltage is 4.0 volts (V), the illuminance is 1,020 cd/m2 of red light, and the current density is 14. 0 mA/cm 2. Furthermore, for 5,000. In terms of illuminance of nit, the illuminance is reduced to the shortest faU6G hour consumed by its 95566 37 201249960 9〇%. Examples 2 to 11: making it a paste! The compound of the present invention is manufactured in an OLED device. (4) as a host material and dopant.
比較例1:使用傳幼你 雅J 、，^ 電場發光化合物製造0LED裝置 以貫施例1之士 目同方式製造0LED裝置，但係藉由使 田 1 4’ —N，N —。上， 相’、〜卡唑—聯苯（CBP)作為主體材料以及化合 物D 11作為^雜劑將厚度為3〇⑽之發光層沉積於該電洞 傳輸層上’且藉由使用雙（2-甲基-8-羥基喹啉）-4-苯基酚 鋁（III)沉積厚度為10 nm之電洞阻擋層。 所製造之0LED裝置顯示，驅動電壓為8.2伏特（V)時， 稱度為1 000 ^^2之紅色發光’電流密度為2〇.〇mA/cm2。 存表，對於5, 000 nit之照度而言，該照度降低至其90% 斤择之最短時間為10小時。 主體 材料 摻雜 劑 驅動電 壓(V) 電流密度 (inA/cm2) 照度 (cd/mz) /顏色 照度自5, 000 nit降至90%所 需之最短時間 C-2 D-11 4.0 14.0 1020/紅 60 C-4 D-7 3.9 7.7 1030/紅 200 飞-13 D-7 3.9 7.1 1050/紅 150 C-14 D-7 4.0 7.2 1090/紅 150 C-21 D-11 4.3 13.2 1010/紅 150 C-33 D-7 4.2 7.2 1040/紅 130 飞-34 D-11 4.3 12.8 1010/紅 130 C-36 D-7 Γ4.1 7.3 「 1080/紅 150 C-37 D-7 4.1 7.5 1080/紅 150 C-39 D-7 4.0 6.7 1050/紅 120 飞-40 D-7 4.0 6.8 1070/紅 120 —CBP D-11 「8.2 20.0 1000/紅 10 95566 38 201249960 本發明之化合物係具有較傳統材料傑出之發光特性。 再者，使用根據本發明之化合物作為主體材料之裝置，藉 由降低驅動電壓而引起功率效率之增加，因此可改進功率 損耗。 【圖式簡單說明】 益 【主要元件符號說明】 無 95566 39Comparative Example 1: Using the Younger You ya, J, and the electric field luminescent compound to manufacture the OLED device The OLED device was fabricated in the same manner as in Example 1, but by making the field 1 4' - N, N -. Above, phase ', ~carbazole-biphenyl (CBP) as a host material and compound D 11 as a dopant to deposit a light-emitting layer having a thickness of 3 Å (10) on the hole transport layer' and by using double (2) -Methyl-8-hydroxyquinoline)-4-phenylphenol aluminum (III) deposits a hole barrier layer having a thickness of 10 nm. The manufactured OLED device showed a red illuminating current density of 2 〇.〇mA/cm2 when the driving voltage was 8.2 volts (V). For the illuminance of 5,000 nit, the illuminance is reduced to 90%. The shortest time is 10 hours. Host material dopant driving voltage (V) Current density (inA/cm2) Illuminance (cd/mz) / Color illumination from 5,000 nit to 90% minimum time required C-2 D-11 4.0 14.0 1020/ Red 60 C-4 D-7 3.9 7.7 1030/Red 200 Fly-13 D-7 3.9 7.1 1050/Red 150 C-14 D-7 4.0 7.2 1090/Red 150 C-21 D-11 4.3 13.2 1010/Red 150 C-33 D-7 4.2 7.2 1040/Red 130 Fly-34 D-11 4.3 12.8 1010/Red 130 C-36 D-7 Γ4.1 7.3 "1080/Red 150 C-37 D-7 4.1 7.5 1080/Red 150 C-39 D-7 4.0 6.7 1050/Red 120 Fly-40 D-7 4.0 6.8 1070/Red 120 —CBP D-11 “8.2 20.0 1000/Red 10 95566 38 201249960 The compounds of the present invention are superior to traditional materials. Further, the device using the compound according to the present invention as a host material can increase the power efficiency by lowering the driving voltage, thereby improving power loss. [Simplified Schematic] Benefits [Main Component Symbol Description] No 95566 39
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020110033910A KR20120116269A (en) | 2011-04-12 | 2011-04-12 | Novel compounds for organic electronic material and organic electroluminescence device using the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201249960A true TW201249960A (en) | 2012-12-16 |
Family
ID=47009548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW101112951A TW201249960A (en) | 2011-04-12 | 2012-04-12 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP2697216A4 (en) |
| JP (1) | JP2014513083A (en) |
| KR (1) | KR20120116269A (en) |
| CN (1) | CN103619833A (en) |
| TW (1) | TW201249960A (en) |
| WO (1) | WO2012141499A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI679199B (en) * | 2017-12-15 | 2019-12-11 | 大陸商廣東阿格蕾雅光電材料有限公司 | Photoelectric material containing 4-thiosulfone aryl dibenzofuran and application thereof |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101478000B1 (en) * | 2010-12-21 | 2015-01-05 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| US9287512B2 (en) | 2011-03-08 | 2016-03-15 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds, layers and organic electroluminescent device using the same |
| KR101354638B1 (en) * | 2011-06-20 | 2014-01-22 | 제일모직주식회사 | MATERIAL for organic OPTOELECTRONIC device, ORGANIC LIGHT EMITTING DIODE INCLUDING THE SAME and DISPLAY INCLUDING THE organic LIGHT EMITTING DIODE |
| KR102028940B1 (en) * | 2012-03-26 | 2019-10-07 | 도레이 카부시키가이샤 | Material for luminescent element, and luminescent element |
| KR101513006B1 (en) * | 2012-06-13 | 2015-04-17 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
| WO2014017484A1 (en) * | 2012-07-25 | 2014-01-30 | 東レ株式会社 | Light emitting element material and light emitting element |
| JPWO2014024750A1 (en) * | 2012-08-09 | 2016-07-25 | 東レ株式会社 | Light emitting device material and light emitting device |
| KR20170127065A (en) * | 2012-12-10 | 2017-11-20 | 코니카 미놀타 가부시키가이샤 | Material for organic electroluminescent element, organic electroluminescent element, illumination device, and display device |
| KR102149450B1 (en) * | 2013-02-15 | 2020-09-01 | 에스에프씨주식회사 | Deuterated organic compounds for organic light-emitting diode and organic light-emitting diode including the same |
| KR102153039B1 (en) | 2013-11-28 | 2020-09-07 | 삼성전자주식회사 | Carbazole-based compound and organic light emitting diode including the same |
| US20170018719A1 (en) * | 2014-03-12 | 2017-01-19 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescence element, ink composition, organic electroluminescence element, and electronic device |
| KR20150108330A (en) * | 2014-03-17 | 2015-09-25 | 롬엔드하스전자재료코리아유한회사 | Electron buffering material and organic electroluminescent device comprising the same |
| KR101764976B1 (en) * | 2014-09-18 | 2017-08-04 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR102648475B1 (en) * | 2014-09-26 | 2024-03-19 | 롬엔드하스전자재료코리아유한회사 | Organic Electroluminescent Compound, and Organic Electroluminescent Material and Organic Electroluminescent Device Comprising the Same |
| WO2016048109A1 (en) * | 2014-09-26 | 2016-03-31 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound, and organic electroluminescent material and organic electroluminescent device comprising the same |
| KR102290914B1 (en) * | 2014-11-10 | 2021-08-17 | 엘지디스플레이 주식회사 | Hetero compounds and organic light emitting devices comprising the same |
| KR102242140B1 (en) * | 2014-11-10 | 2021-04-20 | 엘지디스플레이 주식회사 | Hetero compounds and organic light emitting devices comprising the same |
| CN107683281A (en) | 2015-06-10 | 2018-02-09 | 默克专利有限公司 | Material for organic electroluminescence device |
| TWI734694B (en) * | 2015-07-29 | 2021-08-01 | 德商麥克專利有限公司 | Compounds having fluorene structures |
| CN106478535A (en) * | 2015-08-31 | 2017-03-08 | 上海和辉光电有限公司 | A kind of material for being applied to OLED field |
| JP6954275B2 (en) * | 2017-03-28 | 2021-10-27 | 東レ株式会社 | Compounds, electronic devices containing them, organic thin film light emitting devices, display devices and lighting devices |
| JP7120015B2 (en) * | 2017-07-10 | 2022-08-17 | 東レ株式会社 | light emitting element |
| CN108424420B (en) * | 2017-09-30 | 2021-01-12 | 北京绿人科技有限责任公司 | Triazine compound containing silicon atom, application thereof and organic electroluminescent device |
| KR102134383B1 (en) * | 2017-12-12 | 2020-07-15 | 주식회사 엘지화학 | Organic light emitting device |
| KR102206482B1 (en) | 2018-04-24 | 2021-01-22 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN112513035A (en) * | 2018-10-04 | 2021-03-16 | 株式会社Lg化学 | Compound and organic light emitting diode comprising same |
| CN114031609A (en) * | 2021-12-14 | 2022-02-11 | 北京燕化集联光电技术有限公司 | Compound containing carbazole and quinazoline structure and application thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101431644B1 (en) * | 2009-08-10 | 2014-08-21 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| NZ602040A (en) * | 2010-03-24 | 2014-12-24 | Genentech Inc | Anti-lrp6 antibodies |
| CN104592206B (en) * | 2010-04-20 | 2019-12-31 | 出光兴产株式会社 | Bicarbazole derivative, material for organic electroluminescent element, and organic electroluminescent element using same |
| KR101007516B1 (en) * | 2010-04-23 | 2011-01-14 | 주식회사 이엘엠 | Organic light emitting material and organic light emitting diode having the same |
| KR101477614B1 (en) * | 2010-09-17 | 2014-12-31 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
-
2011
- 2011-04-12 KR KR1020110033910A patent/KR20120116269A/en not_active Application Discontinuation
-
2012
- 2012-04-12 WO PCT/KR2012/002762 patent/WO2012141499A1/en active Application Filing
- 2012-04-12 TW TW101112951A patent/TW201249960A/en unknown
- 2012-04-12 JP JP2014505079A patent/JP2014513083A/en active Pending
- 2012-04-12 EP EP12771699.1A patent/EP2697216A4/en not_active Withdrawn
- 2012-04-12 CN CN201280028741.XA patent/CN103619833A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI679199B (en) * | 2017-12-15 | 2019-12-11 | 大陸商廣東阿格蕾雅光電材料有限公司 | Photoelectric material containing 4-thiosulfone aryl dibenzofuran and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103619833A (en) | 2014-03-05 |
| JP2014513083A (en) | 2014-05-29 |
| KR20120116269A (en) | 2012-10-22 |
| EP2697216A1 (en) | 2014-02-19 |
| WO2012141499A1 (en) | 2012-10-18 |
| EP2697216A4 (en) | 2014-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW201249960A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| JP6543211B2 (en) | Electroluminescent device using electroluminescent compound as luminescent material | |
| TWI634113B (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| JP6278894B2 (en) | Organic electroluminescence device | |
| JP6046701B2 (en) | Novel organic electroluminescent compound and organic electroluminescent device using the same | |
| KR102406323B1 (en) | Nitrogen-containing compounds, electronic devices and electronic devices | |
| JP2017031169A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| TW201307329A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| WO2017135510A1 (en) | Compound for organic optoelectronic device, organic optoelectronic device and display apparatus | |
| KR20110049217A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20130094903A (en) | Novel organic electroluminescent compounds | |
| KR20110049244A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20100118700A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| TW201439277A (en) | Organic electroluminescent compounds and an organic electroluminescent device comprising the same | |
| KR20120104086A (en) | Nitrogen-containing aromatic heterocyclic derivative and organic electroluminescent element using the same | |
| KR20120038060A (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| KR20110112098A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20110013220A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| TW201600521A (en) | New materials with aza-dibenzothiophene or aza-dibenzofuran core for PHOLED | |
| JP2013528927A (en) | Novel organic electroluminescent compound and organic electroluminescent device using the same | |
| TW201118150A (en) | Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same | |
| KR20120122812A (en) | Novel organic electroluminescence compounds and organic electroluminescence device using the same | |
| TW201302973A (en) | Novel organic electroluminescent compounds and an organic electroluminescent device using the same | |
| KR20110008784A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| KR20120009984A (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same |