WO2012141499A1 - 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
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- WO2012141499A1 WO2012141499A1 PCT/KR2012/002762 KR2012002762W WO2012141499A1 WO 2012141499 A1 WO2012141499 A1 WO 2012141499A1 KR 2012002762 W KR2012002762 W KR 2012002762W WO 2012141499 A1 WO2012141499 A1 WO 2012141499A1
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- Prior art keywords
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- substituted
- unsubstituted
- compound
- aryl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 172
- 239000012776 electronic material Substances 0.000 title description 8
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 32
- -1 andenylene Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000001072 heteroaryl 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 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000005382 boronyl group Chemical group 0.000 claims description 2
- 125000005566 carbazolylene group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005584 chrysenylene group Chemical group 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000005565 oxadiazolylene group Chemical group 0.000 claims description 2
- 125000005564 oxazolylene group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005550 pyrazinylene group Chemical group 0.000 claims description 2
- 125000005548 pyrenylene group Chemical group 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 125000005557 thiazolylene group Chemical group 0.000 claims description 2
- 125000005730 thiophenylene group Chemical group 0.000 claims description 2
- 125000005558 triazinylene group Chemical group 0.000 claims description 2
- 125000005559 triazolylene group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000011541 reaction mixture Substances 0.000 description 91
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- 238000002360 preparation method Methods 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
- 239000000203 mixture Substances 0.000 description 43
- 239000010410 layer Substances 0.000 description 38
- 239000012044 organic layer Substances 0.000 description 37
- 239000007787 solid Substances 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 30
- 239000000463 material Substances 0.000 description 30
- 230000002829 reductive effect Effects 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 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 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000012153 distilled water Substances 0.000 description 17
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 229910000029 sodium carbonate Inorganic materials 0.000 description 15
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 10
- TUQSVSYUEBNNKQ-UHFFFAOYSA-N 2,4-dichloroquinazoline Chemical compound C1=CC=CC2=NC(Cl)=NC(Cl)=C21 TUQSVSYUEBNNKQ-UHFFFAOYSA-N 0.000 description 9
- 0 CC(CC=C1*(c2ccccc2[N+]2)NC2[n](c(cccc2)c2c2c3)c2ccc3-c(cc2)cc(c3c4)c2[s]c3ccc4-c2ccccc2)c2c1[s]c1ccccc21 Chemical compound CC(CC=C1*(c2ccccc2[N+]2)NC2[n](c(cccc2)c2c2c3)c2ccc3-c(cc2)cc(c3c4)c2[s]c3ccc4-c2ccccc2)c2c1[s]c1ccccc21 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000008213 purified water Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 238000000151 deposition Methods 0.000 description 5
- 230000005484 gravity Effects 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 4
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 3
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 229910052741 iridium Inorganic materials 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
- 150000002739 metals Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-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
- 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
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052814 silicon oxide 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
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- 125000006835 (C6-C20) arylene group Chemical group 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 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
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 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
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-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
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 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
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- BHSYCNSLQFLRTD-UHFFFAOYSA-N C(C1)C=Cc2c1c(cccc1-c3cccc(-c4nc(-[n](c(cccc5)c5c5c6)c5ccc6-c(cc5c6c7cccc6)ccc5[n]7-c5ccccc5)nc5ccccc45)c3)c1[o]2 Chemical compound C(C1)C=Cc2c1c(cccc1-c3cccc(-c4nc(-[n](c(cccc5)c5c5c6)c5ccc6-c(cc5c6c7cccc6)ccc5[n]7-c5ccccc5)nc5ccccc45)c3)c1[o]2 BHSYCNSLQFLRTD-UHFFFAOYSA-N 0.000 description 1
- SFKCXEVXOFTRJY-UHFFFAOYSA-N C(C1c2c3ccc(C(C=C4)=CC(C5C=CC=CC55)C4N5C(NC4c5ccc6[o]c(cccc7)c7c6c5)=NC5C4=CC=CC5)c2)C=CCC1N3c1ccccc1 Chemical compound C(C1c2c3ccc(C(C=C4)=CC(C5C=CC=CC55)C4N5C(NC4c5ccc6[o]c(cccc7)c7c6c5)=NC5C4=CC=CC5)c2)C=CCC1N3c1ccccc1 SFKCXEVXOFTRJY-UHFFFAOYSA-N 0.000 description 1
- FHTBBXYAAHTQBV-UHFFFAOYSA-O C(CC1)CC11C2C=CC(C(C=CC34)=CC3c(cccc3)c3N4C3N=C(c4c5[s]c6ccccc6c5ccc4)c4ccccc4[NH2+]3)=CC2C2=CC=CCC12 Chemical compound C(CC1)CC11C2C=CC(C(C=CC34)=CC3c(cccc3)c3N4C3N=C(c4c5[s]c6ccccc6c5ccc4)c4ccccc4[NH2+]3)=CC2C2=CC=CCC12 FHTBBXYAAHTQBV-UHFFFAOYSA-O 0.000 description 1
- FYCCCRQUSYCLEC-UHFFFAOYSA-N C(CC1)Cc(c2c3CCC(c(cc4)cc(C5C6=CC=CC5)c4N6C4=CC=CCC4)=C2)c1[n]3C(N=C1c2c3[o]c(C(CC=C4)C5C=CC=CC5)c4c3ccc2)=NC2C1=CC=CC2 Chemical compound C(CC1)Cc(c2c3CCC(c(cc4)cc(C5C6=CC=CC5)c4N6C4=CC=CCC4)=C2)c1[n]3C(N=C1c2c3[o]c(C(CC=C4)C5C=CC=CC5)c4c3ccc2)=NC2C1=CC=CC2 FYCCCRQUSYCLEC-UHFFFAOYSA-N 0.000 description 1
- ZKWUACIEGQPCAS-UHFFFAOYSA-N C(CC1)Cc2c1[s]c1c2cc(C2NC([n]3c(C=CC(C4)C(C=CC56)=CC5c(cccc5)c5N6c5ccccc5)c4c4c3cccc4)=NC3C2=CCCC3)cc1 Chemical compound C(CC1)Cc2c1[s]c1c2cc(C2NC([n]3c(C=CC(C4)C(C=CC56)=CC5c(cccc5)c5N6c5ccccc5)c4c4c3cccc4)=NC3C2=CCCC3)cc1 ZKWUACIEGQPCAS-UHFFFAOYSA-N 0.000 description 1
- WLIZPTJFZVMSFU-UHFFFAOYSA-N CC(C1)(c2ccccc2N2c3ccccc3)C2=CC=C1C(C=CC12)=CC1(C)C1=CC=CCC1(C)N2C(N=C1c2c3[s]c(cccc4)c4c3ccc2)=NC2(C)C1=CC=CC2 Chemical compound CC(C1)(c2ccccc2N2c3ccccc3)C2=CC=C1C(C=CC12)=CC1(C)C1=CC=CCC1(C)N2C(N=C1c2c3[s]c(cccc4)c4c3ccc2)=NC2(C)C1=CC=CC2 WLIZPTJFZVMSFU-UHFFFAOYSA-N 0.000 description 1
- RJBSVEANEVPVRP-UHFFFAOYSA-N CC(C1)C(NC2=CC=CCC22C)=C2C=C1c(cc1)cc(C2(C)C=CC=CC22)c1N2c1ccccc1 Chemical compound CC(C1)C(NC2=CC=CCC22C)=C2C=C1c(cc1)cc(C2(C)C=CC=CC22)c1N2c1ccccc1 RJBSVEANEVPVRP-UHFFFAOYSA-N 0.000 description 1
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- LHCZQJPBRGPPCC-UHFFFAOYSA-O CC(CC=C1)c2c1[n](C1N=C(c3c4[o]c(cccc5)c5c4ccc3)c3ccccc3[NH2+]1)c(cc1)c2cc1-c1cc(-c2ccccc2C23c4cc(C)ccc4-c4ccccc24)c3cc1 Chemical compound CC(CC=C1)c2c1[n](C1N=C(c3c4[o]c(cccc5)c5c4ccc3)c3ccccc3[NH2+]1)c(cc1)c2cc1-c1cc(-c2ccccc2C23c4cc(C)ccc4-c4ccccc24)c3cc1 LHCZQJPBRGPPCC-UHFFFAOYSA-O 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VDYFFXPVIBDLOT-UHFFFAOYSA-N Cc1nc(C)nc2ccccc12 Chemical compound Cc1nc(C)nc2ccccc12 VDYFFXPVIBDLOT-UHFFFAOYSA-N 0.000 description 1
- MYFRZNHPJRVVKL-UHFFFAOYSA-N ClC1=NNC2C1=CC=CC2 Chemical compound ClC1=NNC2C1=CC=CC2 MYFRZNHPJRVVKL-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
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- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
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- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
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- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
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- 125000003342 alkenyl group Chemical group 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 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 1
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- FWVISQOPXODCQT-UHFFFAOYSA-N c(cc12)ccc1[nH]nc2-c1cc(-c2cccc3c2[o]c2ccccc32)ccc1 Chemical compound c(cc12)ccc1[nH]nc2-c1cc(-c2cccc3c2[o]c2ccccc32)ccc1 FWVISQOPXODCQT-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 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
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 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
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=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
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
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- 229910052747 lanthanoid Inorganic materials 0.000 description 1
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000126 substance Substances 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
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
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- 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
- 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
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- 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
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- 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
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- 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
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- H—ELECTRICITY
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- 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
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- 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
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- 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
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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Definitions
- the present invention relates to novel compounds for organic electronic material and an organic electroluminescent device using the same.
- An electroluminescent (EL) device is a self-light-emitting device which has advantages over other types of display devices in that it provides a wider viewing angle, a greater contrast ratio, and has a faster response time.
- An organic EL device was first developed by Eastman Kodak, by using small molecules which are aromatic diamines, and aluminum complexes as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
- Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively.
- 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent substances.
- WO 2006/049013 discloses compounds for organic electroluminescent materials having a condensed bicyclic group as a backbone structure. However, it does not disclose a compound having a nitrogen-containing condensed bicyclic group, a carbazole group which is substituted with an aromatic ring-fused cycloalkyl or heterocycloalkyl group at each of the 3- and 9- positions, and an aromatic ring-fused heterocycloalkyl or cycloalkyl group.
- the objective of the present invention is to provide a compound for organic electronic material, which has an excellent structure imparting high luminous efficiency and a long operation lifetime to a device, and having proper color coordination; and an organic electroluminescent device, which has high efficiency and a long lifetime, using said compounds.
- L1 and L2 each independently represent a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;
- X1 represents CH or N
- Y1 and Y2 each independently represent -O-, -S-, -CR 8 R 9 - or -NR1 0 -;
- R1 to R 10 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring
- R 21 to R 27 have the same definition as one of R1 to R 10 ;
- a, b, e and g each independently represent an integer of 1 to 4; where a, b, e or g is an integer of 2 or more, each of R1, each of R 2 , each of R 5 or each of R 7 is the same or different;
- c, d and f each independently represent an integer of 1 to 3; where c, d or f is an integer of 2 or more, each of R 3 , each of R 4 , or each of R 6 is the same or different; and
- the compounds for organic electronic material according to the present invention can manufacture an organic electroluminescent device which has high luminous efficiency and a long operation lifetime.
- the present invention relates to a compound for organic electronic material represented by the above formula 1 and an organic electroluminescent device comprising the compound.
- (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.;
- (C2-C30) alkenyl(ene) is meant to be a linear or branched alkenyl(ene) having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
- “(C2-C30)alkynyl” is a linear or branched alkynyl having 2 to
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
- R1 to R 10 and R 21 to R 27 groups are each independently at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl substituted or unsubstituted with a halogen, a (C6-C30)aryl, a 5- to 30-membered heteroaryl substitute
- L1 and L2 each independently are preferably a single bond, a substituted or unsubstituted 5- to 21-membered heteroarylene group, a substituted or unsubstituted (C6-C20)arylene group, or a substituted or unsubstituted (C6-C20)cycloarylene group, more preferably one selected from group consisting of a single bond, phenylene, naphthylene, biphenylene, terphenylene, anthrylene, andenylene, fluorenylene, phenanthrylene, triphenylenylene, pyrenylene, phenylenylene, chrysenylene, naphthasenylene, fluorantenyl, furylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, ox
- Y1 and Y2 each independently represent -O-, -S-, -CR 8 R 9 - or -NR 10 -, wherein R 8 and R 9 preferably each independently a substituted or unsubstituted (C1-C30)alkyl group or a substituted or unsubstituted (C6-C30)aryl group, or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, more preferably each independently represent an unsubstituted (C1-C10)alkyl group or an unsubstituted (C6-C12)aryl group, or are linked to an adjacent substituent to form a mono- or polycyclic, (C1-C10)alicyclic or (C6-C15)aromatic ring.
- R 10 preferably represents a substituted or unsubstituted (C6-C30)aryl group or a substituted or unsubstituted 3- to 30-membered heteroaryl group, more preferably represents a (C6-C20)aryl group unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl or a (C6-C12)aryl, or a 5- to 21-membered heteroaryl group substituted with a (C6-C12)aryl.
- R1 to R 7 preferably each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl group or -SiR 23 R 24 R 25 , or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, more preferably each independently represent hydrogen, an unsubstituted (C6-C12)aryl group or -SiR 23 R 24 R 25 , or are linked to an adjacent substituent to form a mono- or polycyclic (C6-C12)aromatic ring.
- the representative compounds of the present invention include the following compounds:
- the compounds for organic electronic materials according to the present invention can be prepared according to the following reaction scheme.
- R1 to R 7 , Y1 and Y2, X1, L1 and L2, a, b, c, d, e, f and g are as defined in formula 1 above, and X represents a halogen.
- the present invention provides an organic electroluminescent device comprising the compound of formula 1.
- Said organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between said first and second electrodes.
- Said organic layer comprises at least one compound of formula 1 according to the present invention.
- said organic layer comprises a light-emitting layer in which the compound of formula 1 is comprised as a host material.
- a phosphorescent dopant which is used for an organic electroluminescent device together with the host material according to the present invention, may be selected from compounds represented by the following formula 2:
- L 101 , L 102 and L 103 are each independently selected from the following structures:
- R 201 to R 203 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s), or a halogen;
- R 204 to R 219 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, SF 5 , a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)aryl
- R 220 to R 223 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s);
- R 224 and R 225 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a halogen, or R 224 and R 225 may be linked to each other via a (C3-C12)alkylene group or (C3-C12)alkenylene group with or without a fused ring, to form a mono- or polycyclic, alicyclic or aromatic ring;
- R 226 represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- or 30-membered heteroaryl group or a halogen;
- R 227 to R 229 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group or a halogen;
- R 231 to R 242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C1-C30)alkoxy group, a halogen, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C5-C30)cycloalkyl group, or each of R 231 to R 242 may be linked to an adjacent substituent via (C2-C30)alkylene group or (C2-C30)alkenylene group to form a spiro ring or a fused ring or may be linked to R 207 or R 208 via a (C2-C30)alkylene group or (C2-C30)alkenylene group to form a saturated or unsaturated fused ring.
- the dopants of formula 2 include the following, but are not limited thereto:
- the organic electroluminescent device according to the present invention may further comprise, in addition to the compounds represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
- the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
- the organic layer may comprise a light-emitting layer and a charge generating layer.
- the organic electroluminescent device may emit a white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, in addition to said organic layer comprising the compound according to the present invention.
- a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
- a chalcogenide(includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer.
- Such a surface layer provides operation stability for the organic electroluminescent device.
- said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
- the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transpor electrons from the mixed region to an electroluminescent medium.
- the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting a white light.
- Example 1 Production of an OLED device using the compound according to the present invention
- OLED device was produced using the compound according to the present invention.
- a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
- N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60nm on the ITO substrate.
- N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
- compound C-2 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material
- compound D-11 was introduced into another cell as a dopant.
- the two materials were evaporated at different rates and were deposited in a doping amount of 4 to 20wt% to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
- the produced OLED device showed red emission having a luminance of 1,020cd/m 2 and a current density of 14.0mA/cm 2 at a driving voltage of 4.0V. Further, the minimum time taken to be reduced to 90% of the luminance at a luminance of 5,000nit was 60 hours.
- Example 2 to 11 Production of an OLED device using the compound according to the present invention
- An OLED device was produced in the same manner as one of Example 1, except for using those shown in the below Table as a host material and a dopant.
- Comparative Example 1 Production of an OLED device using conventional electroluminescent compounds
- An OLED device was produced in the same manner as that of Example 1, except that a light-emitting layer having a thickness of 30 nm was deposited on the hole transport layer by using 4,4’-N,N’-dicarbazol-biphenyl (CBP) as a host material and compound D-11 as a dopant and that a hole blocking layer having a thickness of 10 nm was deposited by using aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate.
- CBP 4,4’-N,N’-dicarbazol-biphenyl
- the produced OLED device showed red emission having a luminance of 1,000cd/m 2 and a current density of 20.0mA/cm 2 at a driving voltage of 8.2V. Further, the minimum time taken to be reduced to 90% of the luminance at a luminance of 5,000nit was 10 hours.
- the compounds of the present invention have superior luminescent properties than the conventional materials. Further, the device using the compounds according to the present invention as a host material induces an increase in power efficiency by reducing a driving voltage, and thus can improve power consumption.
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Abstract
The present invention relates to a novel compound and an organic electroluminescent device containing the same. The compound according to the present invention has an advantage in manufacturing an organic electroluminescent device which has high luminous efficiency and a long operation lifetime.
Description
The present invention relates to novel compounds for organic electronic material and an organic electroluminescent device using the same.
An electroluminescent (EL) device is a self-light-emitting device which has advantages over other types of display devices in that it provides a wider viewing angle, a greater contrast ratio, and has a faster response time. An organic EL device was first developed by Eastman Kodak, by using small molecules which are aromatic diamines, and aluminum complexes as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
The most important factor to determine luminous efficiency in an organic EL device is a light-emitting material. Until now, fluorescent materials have been widely used as a light-emitting material. However, in view of electroluminescent mechanisms, phosphorescent materials theoretically show four (4) times higher luminous efficiency than fluorescent materials. Thus, recently, phosphorescent materials have been investigated. Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp)2), tris(2-phenylpyridine)iridium (Ir(ppy)3) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively. At present, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent substances. Further, Pioneer (Japan) et al. developed a high performance organic EL device employing, as a host material, bathocuproine (BCP) and aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq) which had been a material used for a hole blocking layer.
Though these phosphorous host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of an organic EL device is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage, and thus the power efficiency should be high in order to reduce power consumption. Although an organic EL device comprising phosphorescent materials provides higher current efficiency (cd/A) than one comprising fluorescent materials, when the conventional materials such as BAlq or CBP are used as phosphorescent host materials, a significantly high driving voltage is necessary compared to an organic EL device using a fluorescent material. Thus, there is no merit in terms of power efficiency (lm/W). (3) Further, the operation lifetime of an organic EL device is short and luminous efficiency is still required to be improved.
International Patent Publication No. WO 2006/049013 discloses compounds for organic electroluminescent materials having a condensed bicyclic group as a backbone structure. However, it does not disclose a compound having a nitrogen-containing condensed bicyclic group, a carbazole group which is substituted with an aromatic ring-fused cycloalkyl or heterocycloalkyl group at each of the 3- and 9- positions, and an aromatic ring-fused heterocycloalkyl or cycloalkyl group.
The objective of the present invention is to provide a compound for organic electronic material, which has an excellent structure imparting high luminous efficiency and a long operation lifetime to a device, and having proper color coordination; and an organic electroluminescent device, which has high efficiency and a long lifetime, using said compounds.
The present inventors found that the above objective can be achieved by a compound represented by the following formula 1:
wherein
L₁ and L₂ each independently represent a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;
X₁ represents CH or N;
Y₁ and Y₂ each independently represent -O-, -S-, -CR8R9- or -NR₁0-;
R₁ to R10 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, a (C3-C30)cycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, -NR21R22, -SiR23R24R25, -SR26, -OR27, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a cyano group, a nitro group, or a hydroxyl group; or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
R21 to R27 have the same definition as one of R₁ to R10;
a, b, e and g each independently represent an integer of 1 to 4; where a, b, e or g is an integer of 2 or more, each of R₁, each of R2, each of R5 or each of R7 is the same or different;
c, d and f each independently represent an integer of 1 to 3; where c, d or f is an integer of 2 or more, each of R3, each of R4, or each of R6 is the same or different; and
the heterocycloalkyl group and the heteroaryl(ene) group contain at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
The compounds for organic electronic material according to the present invention can manufacture an organic electroluminescent device which has high luminous efficiency and a long operation lifetime.
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The present invention relates to a compound for organic electronic material represented by the above formula 1 and an organic electroluminescent device comprising the compound.
Herein, “(C1-C30)alkyl(ene)” is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.; “(C2-C30) alkenyl(ene)” is meant to be a linear or branched alkenyl(ene) having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.; “(C2-C30)alkynyl” is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.; “(C1-C30)alkoxy” is a linear or branched alkoxy having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, etc.; “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.; “(C6-C30)cycloalkylene” is one formed by removing a hydrogen from cycloalkyl having 6 to 30, preferably 6 to 20, more preferably 6 or 7 carbon atoms; and “5- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from B, N, O, S, P(=O), Si and P, preferably N, O and S, and 5 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.; “(C6-C30)aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 12, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. Further, “3- to 30-membered heteroaryl(ene)” is an aryl having at least one, preferably 1 to 4 heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, and 3 to 30 ring backbone atoms; is a monocyclic ring or fused ring condensed with at least one benzene ring; has preferably 5 to 21, more preferably 5 to 12 ring backbone atoms; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. “Halogen” includes F, Cl, Br and I.
Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent. Substituents of the substituted alkyl(ene) group, the substituted alkenyl group, the substituted alkynyl group, the substituted cycloalkylene group, the substituted cycloalkyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group, the substituted heteroaryl(ene) group and the substituted aromatic ring in said L₁ and L₂, R₁ to R10 and R21 to R27 groups are each independently at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl substituted or unsubstituted with a halogen, a (C6-C30)aryl, a 5- to 30-membered heteroaryl substituted or unsubstituted with a (C6-C30)aryl, a (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group, a (C1-C30)alkyl silyl group, a (C6-C30)aryl silyl group, a (C1-C30)alkyl (C6-C30)aryl silyl group, a (C2-C30)alkenyl group, a (C2-C30)alkynyl group, a cyano group, a carbazolyl group, a (C1-C30)alkyl amino group, a (C6-C30)aryl amino group, a (C1-C30)alkyl (C6-C30)aryl amino group, a (C6-C30)aryl boronyl group, a (C1-C30)alkyl boronyl, a (C1-C30)alkyl (C6-C30)aryl boronyl, a (C6-C30)aryl (C1-C30)alkyl group, a (C1-C30)alkyl (C6-C30)aryl group, a carbonyl group, a carboxyl group, a nitro group and a hydroxyl group.
In the above formula 1, L₁ and L₂ each independently are preferably a single bond, a substituted or unsubstituted 5- to 21-membered heteroarylene group, a substituted or unsubstituted (C6-C20)arylene group, or a substituted or unsubstituted (C6-C20)cycloarylene group, more preferably one selected from group consisting of a single bond, phenylene, naphthylene, biphenylene, terphenylene, anthrylene, andenylene, fluorenylene, phenanthrylene, triphenylenylene, pyrenylene, phenylenylene, chrysenylene, naphthasenylene, fluorantenyl, furylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridylene, pyrazinylene, pyrimidinylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzooxazolylene, isoindolylene, indolylene, indazolylene, benzothiadiazolylene, quinolylene, isoquinolylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenanthridinylene, benzodioxolylene, dibenzofuranylene and dibenzothiophenylene.
In the above formula 1, Y₁ and Y₂ each independently represent -O-, -S-, -CR8R9- or -NR10-, wherein R8 and R9 preferably each independently a substituted or unsubstituted (C1-C30)alkyl group or a substituted or unsubstituted (C6-C30)aryl group, or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, more preferably each independently represent an unsubstituted (C1-C10)alkyl group or an unsubstituted (C6-C12)aryl group, or are linked to an adjacent substituent to form a mono- or polycyclic, (C1-C10)alicyclic or (C6-C15)aromatic ring. And, R10 preferably represents a substituted or unsubstituted (C6-C30)aryl group or a substituted or unsubstituted 3- to 30-membered heteroaryl group, more preferably represents a (C6-C20)aryl group unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl or a (C6-C12)aryl, or a 5- to 21-membered heteroaryl group substituted with a (C6-C12)aryl.
In the above formula 1, R₁ to R7 preferably each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl group or -SiR23R24R25, or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, more preferably each independently represent hydrogen, an unsubstituted (C6-C12)aryl group or -SiR23R24R25, or are linked to an adjacent substituent to form a mono- or polycyclic (C6-C12)aromatic ring.
In the above formula 1, 
is selected from the followingstructures, but are not limited thereto:
The representative compounds of the present invention include the following compounds:
The compounds for organic electronic materials according to the present invention can be prepared according to the following reaction scheme.
[Reaction Scheme]
wherein R₁ to R7, Y₁ and Y₂, X₁, L₁ and L₂, a, b, c, d, e, f and g are as defined in formula 1 above, and X represents a halogen.
In addition, the present invention provides an organic electroluminescent device comprising the compound of formula 1. Said organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between said first and second electrodes. Said organic layer comprises at least one compound of formula 1 according to the present invention. Further, said organic layer comprises a light-emitting layer in which the compound of formula 1 is comprised as a host material.
In addition, a phosphorescent dopant, which is used for an organic electroluminescent device together with the host material according to the present invention, may be selected from compounds represented by the following formula 2:
wherein M₁ is selected from the group consisting of Ir, Pt, Pd and Os; L101, L102 and L103 are each independently selected from the following structures:
R201 to R203 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s), or a halogen;
R204 to R219 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, SF5, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a cyano group or a halogen;
R220 to R223 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s);
R224 and R225 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a halogen, or R224 and R225 may be linked to each other via a (C3-C12)alkylene group or (C3-C12)alkenylene group with or without a fused ring, to form a mono- or polycyclic, alicyclic or aromatic ring;
R226 represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- or 30-membered heteroaryl group or a halogen;
R227 to R229 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group or a halogen;
Q represents 
or 
;R231 to R242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C1-C30)alkoxy group, a halogen, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C5-C30)cycloalkyl group, or each of R231 to R242 may be linked to an adjacent substituent via (C2-C30)alkylene group or (C2-C30)alkenylene group to form a spiro ring or a fused ring or may be linked to R207 or R208 via a (C2-C30)alkylene group or (C2-C30)alkenylene group to form a saturated or unsaturated fused ring.
The dopants of formula 2 include the following, but are not limited thereto:
The organic electroluminescent device according to the present invention may further comprise, in addition to the compounds represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
In the organic electroluminescent device according to the present invention, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal. The organic layer may comprise a light-emitting layer and a charge generating layer.
The organic electroluminescent device according to the present invention may emit a white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, in addition to said organic layer comprising the compound according to the present invention.
Preferably, in the organic electroluminescent device according to the present invention, at least one layer (hereinafter, "a surface layer”) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s). Specifically, it is preferred that a chalcogenide(includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, said chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and said metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
Preferably, in the organic electroluminescent device according to the present invention, a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transpor electrons from the mixed region to an electroluminescent medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting a white light.
Hereinafter, the compound for organic electronic material, the preparation method of the compound, and the luminescent properties of the device comprising the compound of the present invention will be explained in detail with reference to the following examples:
Preparation Example 1: Preparation of compound C-2
Preparation of compound C-1-1
9-phenyl-9H-carbazol-3-yl boronic acid (14 g, 48.76 mmol), 3-bromo-9H-carbazole (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 toluene 200mL, EtOH 50mL and purified water 50mL. After stirring the reaction mixture for 3 hours at 90~100°C, the mixture was cooled to room temperature. An aqueous layer was removed from the mixture by a gravity separation. The obtained organic layer was concentrated, was triturated with methylene chloride (MC), and then was filtered to produce compound C-1-1 (12 g, 72%).
Preparation of compound C-1-2
After dissolving 2,4-dichloroquinazoline (30g, 151mmol), 9-phenyl-9H-carbazol-3-yl boronic acid (15.6g, 75.3mmol), Pd(PPh3)4 (2.6g, 2.3mmol) and Na2CO3 (16g, 150mmol) in a mixture of toluene (300mL) and distilled water (75mL), the reaction mixture was stirred for 2 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was triturated with MeOH. The obtained solid was dissolved in MC, was filtered through silica, and then was triturated with MC and hexane to produce compound C-1-2 (9.3g, 51.4%).
Preparation of compound C-2
After suspending compound C-1-1 (5.3 g, 14.7 mmol) and compound C-1-2 (6.4 g, 15.8 mmol) in dimethyl formamide (DMF) 80mL, 60% NaH (948 mg, 22 mmol) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, was dissolved in MC, was filtered through silica, and then was triturated with MC/n-hexane to obtain compound C-2 (1.9 g, 16.8%).
MS/FAB found 778; calculated 777.91
Preparation Example 2: Preparation of compound C-13
Preparation of compound C-2-1
After dissolving 2,4-dichloroquinazoline (50 g, 251 mmol) and dibenzo[b,d]furan-4-yl boronic acid (53.2g, 251 mmol) in a mixture of toluene (1 L) and water (200 mL), tetrakistriphenylphosphine palladium (14.5 g, 12.5 mmol) and sodium carbonate (80 g, 755 mmol) were added to the reaction mixture. The reaction mixture was stirred for 20 hours at 80°C, and cooled to room temperature. After terminating the reaction with ammonium chloride aqueous solution 200 mL, the reaction mixture was extracted with ethyl acetate 1 L, and further an aqueous layer was extracted with dichloromethane 1 L. An organic layer was dried with anhydrous magnesium sulfate, and removed under reduced pressure. The obtained solid was filtered through silica gel, and the solution was removed under reduced pressure. The obtained solid was washed with ethyl acetate (EtOAc) 100 mL to produce compound C-2-1 (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 added slowly to the reaction mixture. After stirring the reaction mixture for 1 hour at room temperature, compound C-2-1 (51 g, 147 mmol) was added to the reaction mixture. The reaction mixture was stirred for 20 hours at room temperature. Ice water was dropped slowly to the reaction mixture to terminate the reaction. And then, the reaction mixture was filtered to obtain the produced solid. The obtained solid was washed with water 1 L, and subsequently with MeOH 1 L. The obtained solid was dried, dissolved in CHCl3 4 L, and filtered through silica gel to remove an inorganic material. The solvent in the obtained solution was removed to obtain solid. The obtained solid was recrystallized in DMF to obtain compound C-13 (50 g, 58 %).
MS/FAB found 703; calculated 702.80
Preparation Example 3: Preparation of compound C-14
Preparation of compound C-3-1
After dissolving 2,4-dichloroquinazoline (50 g, 251 mmol) and dibenzo[b,d]thiophen-4-yl boronic acid (57.3g, 251 mmol) in a mixture of toluene (1 L) and water (200 mL), tetrakistriphenylphosphine palladium (14.5 g, 12.5 mmol) and sodium carbonate (80 g, 755 mmol) were added to the reaction mixture. The reaction mixture was stirred for 20 hours at 80°C, and cooled to room temperature. After terminating the reaction with ammonium chloride aqueous solution 200 mL, the reaction mixture was extracted with ethyl acetate 1 L, and further an aqueous layer was extracted with dichloromethane 1 L. An organic layer was dried with anhydrous magnesium sulfate, and removed under reduced pressure. The obtained solid was filtered through silica gel, and the solution was removed under reduced pressure. The obtained solid was washed with ethyl acetate (EtOAc) 100 mL to produce compound C-3-1 (50 g, 60 %).
Preparation of compound C-14
After dissolving compound C-1-1 (50 g, 122 mmol) in DMF, 60 % NaH (5.9 g, 148 mmol) was added slowly to the reaction mixture. After stirring the reaction mixture for 1 hour at room temperature, compound C-3-1 (51 g, 147 mmol) was added to the reaction mixture. The reaction mixture was stirred for 20 hours at room temperature. Ice water was dropped slowly to the reaction mixture to terminate the reaction. And then, the reaction mixture was filtered to obtain the produced solid. The obtained solid was washed with water 1 L, and subsequently with MeOH 1 L. The obtained solid was dried, dissolved in CHCl3 4 L, and filtered through silica gel to remove an inorganic material. The solvent in the obtained solution was removed to obtain solid. The obtained solid was recrystallized in DMF to obtain compound C-14 (50 g, 57 %).
MS/FAB found 729; calculated 718.87
Preparation Example 4: Preparation of compound C-20
Preparation of compound C-4-1
After dissolving dibenzo[b,d]furan-4-yl boronic acid (19 g, 89.6 mmol), bromobenzene (18.4 ml, 138 mmol), Pd(PPh3)4 (2.9 g, 2.5 mmol) and Na2CO3 (23.2 g, 219 mmol) in a mixture of toluene (375mL), EtOH (75mL) and distilled water (75mL), the reaction mixture was stirred for 4 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was filtered through column with MC and hexane to obtain compound C-4-1 (17 g, 77 %).
Preparation of compound C-4-2
After dissolving compound C-4-1 (17 g, 65.3 mmol) in tetrahydrofuran (THF) (500 ml), and adding 2.5 M n-BuLi in hexane (52.2 ml, 130 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours with adding B(Oi-Pr)₃ (21.8 ml, 195 mmol) slowly to the reaction mixture. After quenching the reaction mixture with adding 2 M HCl, the reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized with MC and hexane to obtain compound C-4-2 (6.4 g, 33%).
Preparation of compound C-4-3
After dissolving compound C-4-2 (4.9 g, 24.4 mmol), 2,4-dichloroquinazoline (6.4 g, 22.2 mmol), Pd(PPh3)4 (1.1 g, 2.5 mmol) and Na2CO3 (7.1 g, 66.6 mmol) in a mixture of toluene (300mL) and distilled water (75mL), the reaction mixture was stirred for 2 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was triturated with MeOH. The obtained solid was dissolved in MC and filtered through silica gel, and then was triturated with MC and hexane to obtain compound C-4-3 (4.1 g, 45%).
Preparation of compound C-20
After suspending compound C-4-3 (4.5 g, 10.9 mmol) and compound C-1-1 (4.1 g, 9.9 mmol) in DMF 80mL, 60% NaH (594 mg, 14.8 mmol) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, and with DMF, and then with EA/THF. The obtained solid was dissolved in MC, was filtered through silica, and then was triturated with MeOH/EA to obtain compound C-20 (3.4 g, 44 %).
MS/FAB found 779; calculated 778.90
Preparation Example 5: Preparation of compound C-21
Preparation of compound C-5-1
After dissolving dibenzo[b,d]thiophen-4-yl boronic acid (20 g, 87.7 mmol), bromobenzene (18.4 ml, 175 mmol), Pd(PPh3)4 (2.9 g, 2.5 mmol) and Na2CO3 (23.2 g, 219 mmol) in a mixture of toluene (375mL), EtOH (75mL) and distilled water (75mL), the reaction mixture was stirred for 4 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was filtered through column with MC and hexane to obtain compound C-5-1 (17 g, 75 %).
Preparation of compound C-5-2
After dissolving compound C-5-1 (17 g, 65.3 mmol) in (THF (500 ml), and adding 2.5 M n-BuLi in hexane (52.2 ml, 130 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours with adding B(Oi-Pr)₃ (21.8 ml, 195 mmol) slowly to the reaction mixture. After quenching the reaction mixture with adding 2 M HCl, the reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized with MC and hexane to obtain compound C-5-2 (11.5 g, 60%).
Preparation of compound C-5-3
After dissolving compound C-5-2 (8.3 g, 41.5 mmol), 2,4-dichloroquinazoline (11.5 g, 37.8 mmol), Pd(PPh3)4 (2.2 g, 2.5 mmol) and Na2CO3 (12 g, 113 mmol) in a mixture of toluene (300mL) and distilled water (75mL), the reaction mixture was stirred for 2 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was triturated with MeOH. The obtained solid was dissolved in MC and filtered through silica gel, and then was triturated with MC and hexane to obtain compound C-5-3 (10 g, 68%).
Preparation of compound C-21
After suspending compound C-5-3 (5 g, 11.8 mmol) and compound C-1-1 (4.8 g, 11.8 mmol) in DMF 80mL, 60% NaH (881 mg, 22 mmol) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, and with DMF, and then with EA/THF. The obtained solid was dissolved in MC, was filtered through silica, and then was triturated with MeOH/EA to obtain compound C-21 (4.8 g, 51 %).
MS/FAB found 795; calculated 794.96
Preparation Example 6: Preparation of compound C-33
Preparation of compound C-6-1
After dissolving dibenzo[b,d]furan-4-yl boronic acid (20 g, 94.34 mmol), 1-bromo-4-iodo-benzene (53.4 ml, 188.68 mmol), Pd(PPh3)4 (5.45 g, 4.72 mmol) and K2CO3 (39.1 g, 283.01 mmol) in a mixture of toluene (900mL), EtOH (200mL) and distilled water (200mL), the reaction mixture was stirred for 3 hours at 70~80°C. After terminating the reaction, an aqueous layer was removed from the mixture by a gravity separation. And then, the obtained organic layer was concentrated and purified through column to obtain compound C-6-1 (17 g, 56 %).
Preparation of compound C-6-2
After dissolving compound C-6-1 (17 g, 52.6 mmol) in THF (400 ml), and adding 2.5 M n-BuLi in hexane (31.5 ml, 78.9 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 12 hours with adding B(Oi-Pr)₃ (24.1 ml, 105.2 mmol) slowly to the reaction mixture. After terminating the reaction, purified water 20 mL was dropped slowly to the reaction mixture. The reaction mixture was extracted with EA/NH4Cl aqueous solution. The obtained organic layer was concentrated, was triturated with MC/hexane, and then was filtered to obtain compound C-6-2 (14.5 g, 96 %).
Preparation of compound C-6-3
After dissolving compound C-6-2 (4.5 g, 50.33 mmol), 2,4-dichloroquinazoline (11.5 g, 50.33 mmol), Na2CO3 (20.9 g, 150.99 mmol) and Pd(PPh3)4 (2.9 g, 2.52 mmol) in a mixture of toluene (300mL), EtOH (75mL) and distilled water (75mL), the reaction mixture was stirred for 12 hours at 75~80°C. After terminating the reaction, the reaction mixture was cooled to room temperature, and an aqueous layer was removed from the mixture by a gravity separation. The obtained organic layer was concentrated, was triturated with THF/MeOH, was filtered, and then was dried. The dried compound was dissolved in chloroform 3 L, and filtered through silica. The remaining solution was concentrated and triturated with EA to obtain compound C-6-3 (3.8 g, 19 %).
Preparation of compound C-33
After suspending compound C-1-1 (3.8 g, 9.34 mmol) and compound C-6-3 (3.8 g, 9.34 mmol) in DMF 80mL, 60% NaH (1.12 g, 28.02 mL) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, and with DMF, and then with EA/THF. The obtained solid was dissolved in MC, was filtered through silica, and then was triturated with MeOH/EA to obtain compound C-33 (2.9 g, 40 %).
MS/FAB found 779; calculated 778.90
Preparation Example 7: Preparation of compound C-34
Preparation of compound C-7-1
After dissolving 1-bromo-4-iodo-benzene (49.6 g, 0.17 mol), dibenzo[b,d]thiophen-4-yl boronic acid (20 g, 0.087 mol), Pd(PPh3)4 (5.0 g, 0.044 mol) and Na2CO3 (18.5 g, 0.18 mol) in a mixture of toluene (880mL) and H2O (200mL) in 2000 mL round-bottom flask, the reaction mixture was stirred for 12 hours at 80°C. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO4 and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through adsorption column to obtain white solid, compound C-7-1 (21.2 g, 71 %).
Preparation of compound C-7-2
After putting compound C-7-1 (21.4 g, 0.06 mol) and dry THF (1000 ml) in 2000 mL round-bottom flask under anhydrous conditions, n-BuLi in hexane (37 ml, 2.25 M solution) was added slowly to the reaction mixture at -78°C with stirring the mixture under nitrogen. The reaction mixture was stirred for 1 hour at -78°C. After adding B(Oi-Pr)₃ (29 ml, 0.13 mol) slowly to the reaction mixture at -78°C, the reaction mixture was heated to room temperature and reacted for 12 hours. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO4 and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through column to obtain white solid, compound C-7-2 (15.5 g, 81 %).
Preparation of compound C-7-3
After adding compound C-7-2 (15.5 g, 0.051 mol), 2,4-dichloroquinazoline (12.2 g, 0.06 mol), Na2CO3 (16.2 g, 0.153 mol) and Pd(PPh3)4 (2.94 g, 0.0025 mol) in a mixture of toluene (250mL), EtOH (40mL) and H2O (70mL) in 250 mL round-bottom flask, the reaction mixture was stirred for 12 hours at 80°C. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO4 and filtered. After removing a solvent from the organic layer under reduced pressure, the obtained solid was recrystallized to obtain compound C-7-3 (14 g, 65 %).
Preparation of compound C-34
NaH 60 % (0.62 g, 0.0154 mol) and DMF (60 ml) was put in 250 mL round-bottom flask under anhydrous conditions. After dissolving compound C-1-1 (4.83 g, 0.012 mol) in DMF (30 ml), the mixture was put in the round-bottom flask. The reaction mixture was stirred for 1 hour. After dissolving compound C-7-3 (5 g, 0.012 mol) in DMF (30 ml), the mixture was put in the round-bottom flask. After stirring the mixture for 12 hours, yellow solid was filtered, was washed with MeOH, was triturated with THF, and then was triturated with DMF to obtain compound C-34 (4.2 g, 45 %).
MS/FAB found 795; calculated 794.96
Preparation Example 8: Preparation of compound C-36
Preparation of compound C-8-1
After dissolving dibenzo[b,d]furan-4-yl boronic acid (20 g, 94.34 mmol), 1,3-dibromobenzene (22.3 g, 94.34 mmol), Pd(PPh3)4 (5.45 g, 4.72 mmol) and K2CO3 (39.1 g, 283.01 mmol) in a mixture of toluene (800mL), EtOH (200mL) and distilled water (200mL), the reaction mixture was stirred for 3 hours at 70~80°C. After terminating the reaction, an aqueous layer was removed from the mixture by a gravity separation. And then, the obtained organic layer was concentrated and purified through silica column to obtain compound C-8-1 (13 g, 43 %).
Preparation of compound C-8-2
After dissolving compound C-8-1 (13 g, 40.23 mmol) in THF (300 ml), and adding 2.5 M n-BuLi in hexane (19 ml, 48.27 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 12 hours with adding B(Oi-Pr)₃ (13.9 ml, 60.34 mmol) slowly to the reaction mixture. After terminating the reaction, purified water 20 mL was dropped slowly to the reaction mixture. The reaction mixture was extracted with EA/NH4Cl aqueous solution. The obtained organic layer was concentrated, was triturated with MC/hexane, and then was filtered to obtain compound C-8-2 (6.8 g, 58.7 %).
Preparation of compound C-8-3
After dissolving compound C-8-2 (6.8 g, 23.6 mmol), 2,4-dichloroquinazoline (5.38 g, 23.6 mmol), Na2CO3 (9.8 g, 70.8 mmol) and Pd(PPh3)4 (1.36 g, 1.18 mmol) in a mixture of toluene (240mL) and distilled water (50mL), the reaction mixture was stirred for 12 hours at 90~100°C. After terminating the reaction, the reaction mixture was cooled to room temperature, and an aqueous layer was removed from the mixture by a gravity separation. The obtained organic layer was concentrated, was triturated with THF/MeOH, was filtered, and then was dried. The dried compound was dissolved in chloroform 3 L, and filtered through silica. The remaining solution was concentrated and triturated with THF/MeOH to obtain compound C-8-3 (3.8 g, 40 %).
Preparation of compound C-36
After suspending compound C-1-1 (3.8 g, 9.34 mmol) and compound C-8-3 (3.8 g, 9.34 mmol) in DMF 80mL, 60% NaH (1.12 g, 28.02 mL) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, was dissolved in MC, was filtered through silica, and then was triturated with MC/n-hexane to obtain compound C-36 (1.6 g, 21 %).
MS/FAB found 779; calculated 778.90
Preparation Example 9: Preparation of compound C-37
Preparation of compound C-9-1
After dissolving 1,3-dibromobenzene (16.5 g, 0.2 mol), dibenzo[b,d]thiophen-4-yl boronic acid (15 g, 0.06 mol), Pd(PPh3)4 (3.8 g, 0.003 mol) and Na2CO3 (14 g, 0.13 mol) in a mixture of toluene (330mL) and H2O (70mL) in 2000 mL round-bottom flask, the reaction mixture was stirred for 12 hours at 80°C. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO4 and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through column to obtain white solid, compound C-9-1 (8.4 g, 40 %).
Preparation of compound C-9-2
After putting compound C-9-1 (8.4 g, 0.025 mol) and dry THF (200 ml) in 500 mL round-bottom flask under anhydrous conditions, n-BuLi in hexane (15 ml, 2.25 M solution) was added slowly to the reaction mixture at -78°C with stirring the mixture under nitrogen. The reaction mixture was stirred for 1 hour at -78°C. After adding B(Oi-Pr)₃ (11.4 ml, 0.05 mol) slowly to the reaction mixture at -78°C, the reaction mixture was heated to room temperature and reacted for 12 hours. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO₄and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through column to obtain white solid, compound C-9-2 (6 g, 80 %).
Preparation of compound C-9-3
After adding compound C-9-2 (5.9 g, 0.02 mol), 2,4-dichloroquinazoline (4.6 g, 0.02 mol), Na2CO3 (6.2 g, 0.058 mol) and Pd(PPh3)4 (1.1 g, 0.00097 mol) in a mixture of toluene (100mL), EtOH (14mL) and H2O (30mL) in 250 mL round-bottom flask, the reaction mixture was stirred for 3 hours at 70°C. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO₄and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through column to obtain 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) was put in 250 mL round-bottom flask under anhydrous conditions. After dissolving compound C-1-1 (3.7 g, 0.009 mol) in DMF (30 ml), the mixture was put in the round-bottom flask. The reaction mixture was stirred for 1 hour. After dissolving compound C-9-3 (4 g, 0.0095 mol) in DMF (30 ml), the mixture was put in the round-bottom flask. After stirring the mixture for 12 hours, yellow solid was filtered, was washed with MeOH, was triturated with THF, and then was triturated with DMF to obtain compound C-37 (1.7 g, 20 %).
MS/FAB found 795; calculated 794.96
Preparation Example 10: Preparation of compound C-39
Preparation of compound C-10-1
After putting compound C-1-1 (14 g, 34.3 mmol) and 1-bromo-4-iodobenzene (48.5 g, 171.4 mmol), CuI (3.3 g, 17.1 mmol), K3PO4 (21.8 g, 102.9 mmol) and ethylene diamine (EDA) (2.3 ml, 34.3 mmol) into toluene (500 ml), the reaction mixture was stirred under reflux for 1 day. The reaction mixture was extracted with EA, was distilled under reduced pressure, and then was filtered through column with MC/hexane to obtain compound C-10-1 (15.5 g, 80.1 %)
Preparation of compound C-10-2
After dissolving compound C-10-1 (15.5 g, 27.5 mmol) in THF (250 ml), and adding 2.5 M n-BuLi in hexane (17.6 ml, 44 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours with adding B(Oi-Pr)₃ (12.6 ml, 55 mmol) slowly to the reaction mixture. After quenching the reaction mixture with adding 2 M HCl, the reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized with MC and hexane to obtain compound C-10-2 (8.7 g, 60 %).
Preparation of compound C-39
After dissolving compound C-3-1 (3.2 g, 9.2 mmol), compound C-10-2 (4.9 g, 9.2 mmol), Pd(PPh3)4 (532 mg, 0.46 mmol) and Na2CO3 (2.9 g, 27.6 mmol) in a mixture of toluene (55 ml), EtOH (14 ml) and distilled water (14 ml), the reaction mixture was stirred for 2 hours at 90°C. The reaction mixture was extracted with distilled water and EA, and then was filtered through column with MC and hexane to obtain compound C-39 (5.5 g, 75 %).
MS/FAB found 795; calculated 794.96
Preparation Example 11: Preparation of compound C-40
Preparation of compound C-40
After dissolving 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) and Na2CO3 (2.9 g, 27.6 mmol) in a mixture of toluene (55 ml), EtOH (14 ml) and distilled water (14 ml), the reaction mixture was stirred for 2 hours at 90°C. The reaction mixture was extracted with distilled water and EA, and then was filtered through column with MC and hexane to obtain compound C-40 (5.5 g, 75 %).
MS/FAB found 779; calculated 778.90
Example 1: Production of an OLED device using the compound according to the present invention
OLED device was produced using the compound according to the present invention. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60nm on the ITO substrate. Then, N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound C-2 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-11 was introduced into another cell as a dopant. The two materials were evaporated at different rates and were deposited in a doping amount of 4 to 20wt% to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 9,10-di(1-naphthyl)-2-(4-phenyl-1-phenyl-1H-benzo[d]imidazole)anthracene was introduced into one cell and lithium quinolate was introduced into another cell. The two materials were evaporated at different rates and were deposited in a doping amount of 30 to 70wt% to form an electron transport layer having a thickness of 30nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 1 to 2nm on the electron transport layer, an Al cathode having a thickness of 150nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the material used for producing the OLED device were those purified by vacuum sublimation at 10-6 torr.
The produced OLED device showed red emission having a luminance of 1,020cd/m2 and a current density of 14.0mA/cm2 at a driving voltage of 4.0V. Further, the minimum time taken to be reduced to 90% of the luminance at a luminance of 5,000nit was 60 hours.
Example 2 to 11: Production of an OLED device using the compound according to the present invention
An OLED device was produced in the same manner as one of Example 1, except for using those shown in the below Table as a host material and a dopant.
Comparative Example 1: Production of an OLED device using conventional electroluminescent compounds
An OLED device was produced in the same manner as that of Example 1, except that a light-emitting layer having a thickness of 30 nm was deposited on the hole transport layer by using 4,4’-N,N’-dicarbazol-biphenyl (CBP) as a host material and compound D-11 as a dopant and that a hole blocking layer having a thickness of 10 nm was deposited by using aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate.
The produced OLED device showed red emission having a luminance of 1,000cd/m2 and a current density of 20.0mA/cm2 at a driving voltage of 8.2V. Further, the minimum time taken to be reduced to 90% of the luminance at a luminance of 5,000nit was 10 hours.
The results of examples and comparative example are shown in the following Table.
The compounds of the present invention have superior luminescent properties than the conventional materials. Further, the device using the compounds according to the present invention as a host material induces an increase in power efficiency by reducing a driving voltage, and thus can improve power consumption.
Claims (6)
- A compound represented by the following formula 1:---------- (1)
whereinL₁ and L₂ each independently represent a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;X₁ represents CH or N;Y₁ and Y₂ each independently represent -O-, -S-, -CR8R9- or -NR10-;R₁ to R10 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, a (C3-C30)cycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, -NR21R22, -SiR23R24R25, -SR26, -OR27, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a cyano group, a nitro group, or a hydroxyl group; or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;R21 to R27 have the same definition as one of R₁ to R10;a, b, e and g each independently represent an integer of 1 to 4; where a, b, e or g is an integer of 2 or more, each of R₁, each of R2, each of R5 or each of R7 is the same or different;c, d and f each independently represent an integer of 1 to 3; where c, d or f is an integer of 2 or more, each of R3, each of R4, or each of R6 is the same or different; andthe heterocycloalkyl group and the heteroaryl(ene) group contain at least one hetero atom selected from B, N, O, S, P(=O), Si and P. - The compound according to claim 1, characterized in that substituents of the substituted alkyl(ene) group, the substituted alkenyl group, the substituted alkynyl group, the substituted cycloalkylene group, the substituted cycloalkyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group, the substituted heteroaryl(ene) group and the substituted aromatic ring in said L₁ and L₂, R₁ to R10 and R21 to R27 groups each independently are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl group substituted or unsubstituted with a halogen, a (C6-C30)aryl group, a 5- to 30-membered heteroaryl group substituted or unsubstituted with a (C6-C30)aryl, a (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group, a (C1-C30)alkyl silyl group, a (C6-C30)aryl silyl group, a (C1-C30)alkyl (C6-C30)aryl silyl group, a (C2-C30)alkenyl group, a (C2-C30)alkynyl group, a cyano group, a carbazolyl group, a (C1-C30)alkyl amino group, a (C6-C30)aryl amino group, a (C1-C30)alkyl (C6-C30)aryl amino group, a (C6-C30)aryl boronyl group, a (C1-C30)alkyl boronyl, a (C1-C30)alkyl (C6-C30)aryl boronyl, a (C6-C30)aryl (C1-C30)alkyl group, a (C1-C30)alkyl (C6-C30)aryl group, a carbonyl group, a carboxyl group, a nitro group and a hydroxyl group.
- The compound according to claim 1, characterized in that X₁ represents CH or N; and L₁ and L₂ each independently is selected from the group consisting of a single bond, phenylene, naphthylene, biphenylene, terphenylene, anthrylene, andenylene, fluorenylene, phenanthrylene, triphenylenylene, pyrenylene, phenylenylene, chrysenylene, naphthasenylene, fluorantenyl, furylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridylene, pyrazinylene, pyrimidinylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzooxazolylene, isoindolylene, indolylene, indazolylene, benzothiadiazolylene, quinolylene, isoquinolylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenanthridinylene, benzodioxolylene, dibenzofuranylene and dibenzothiophenylene.
- The compound according to claim 1, characterized in thatin formula 1 is selected from the following structures:
- The compound according to claim 1, characterized in that the compound represented by formula 1 is selected from the group consisting of:
- An organic electroluminescent device comprising the compound according to claim 1.
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2012
- 2012-04-12 JP JP2014505079A patent/JP2014513083A/en active Pending
- 2012-04-12 WO PCT/KR2012/002762 patent/WO2012141499A1/en active Application Filing
- 2012-04-12 CN CN201280028741.XA patent/CN103619833A/en active Pending
- 2012-04-12 TW TW101112951A patent/TW201249960A/en unknown
- 2012-04-12 EP EP12771699.1A patent/EP2697216A4/en not_active Withdrawn
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| KR101007516B1 (en) * | 2010-04-23 | 2011-01-14 | 주식회사 이엘엠 | Organic light emitting material and organic light emitting diode having the same |
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| 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 |
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| EP2675867A4 (en) * | 2011-06-20 | 2014-11-19 | Cheil Ind Inc | Material for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode |
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| JPWO2015137471A1 (en) * | 2014-03-12 | 2017-04-06 | 出光興産株式会社 | COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE, INK COMPOSITION, ORGANIC ELECTROLUMINESCENT DEVICE, AND ELECTRONIC DEVICE |
| WO2015137471A1 (en) * | 2014-03-12 | 2015-09-17 | 出光興産株式会社 | Compound, material for organic electroluminescence element, ink composition, organic electroluminescence element, and electronic device |
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| WO2016198144A1 (en) | 2015-06-10 | 2016-12-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| WO2017016667A1 (en) * | 2015-07-29 | 2017-02-02 | Merck Patent Gmbh | Compounds having fluorene structures |
| US11201296B2 (en) | 2015-07-29 | 2021-12-14 | Merck Patent Gmbh | Compounds having fluorene structures |
| US11685859B2 (en) | 2017-12-12 | 2023-06-27 | Lg Chem, Ltd. | Organic light emitting device |
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Also Published As
| Publication number | Publication date |
|---|---|
| CN103619833A (en) | 2014-03-05 |
| EP2697216A1 (en) | 2014-02-19 |
| KR20120116269A (en) | 2012-10-22 |
| TW201249960A (en) | 2012-12-16 |
| EP2697216A4 (en) | 2014-10-15 |
| JP2014513083A (en) | 2014-05-29 |
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