WO2014058232A2 - Matériau organique de type spiro et dispositif électroluminescent organique le mettant en œuvre - Google Patents
Matériau organique de type spiro et dispositif électroluminescent organique le mettant en œuvre Download PDFInfo
- Publication number
- WO2014058232A2 WO2014058232A2 PCT/KR2013/009038 KR2013009038W WO2014058232A2 WO 2014058232 A2 WO2014058232 A2 WO 2014058232A2 KR 2013009038 W KR2013009038 W KR 2013009038W WO 2014058232 A2 WO2014058232 A2 WO 2014058232A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- phenyl
- substituted
- compound
- formula
- electroluminescent device
- Prior art date
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- 239000011368 organic material Substances 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- -1 cyano, phenyl Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 56
- 239000000543 intermediate Substances 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000010410 layer Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- 0 [*+]c(cccc1)c1N(c(cc1)ccc1F)c1cc(C2(c3ccccc3-c3c2cccc3)c2cc(N(c(cc3)ccc3F)c3ccccc3S)ccc2-2)c-2c2ccccc12 Chemical compound [*+]c(cccc1)c1N(c(cc1)ccc1F)c1cc(C2(c3ccccc3-c3c2cccc3)c2cc(N(c(cc3)ccc3F)c3ccccc3S)ccc2-2)c-2c2ccccc12 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000012300 argon atmosphere Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 8
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YKPUGSUIAVTFMB-UHFFFAOYSA-N FC(c1cc(N(c(cc2)ccc2F)c(cc2)cc(C34c5ccccc5-c5c3cccc5)c2-c(c2c3cccc2)c4cc3N(c(cc2)ccc2F)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc(C(F)(F)F)c1)(F)F Chemical compound FC(c1cc(N(c(cc2)ccc2F)c(cc2)cc(C34c5ccccc5-c5c3cccc5)c2-c(c2c3cccc2)c4cc3N(c(cc2)ccc2F)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc(C(F)(F)F)c1)(F)F YKPUGSUIAVTFMB-UHFFFAOYSA-N 0.000 description 2
- HJHDNWCDIJTMGE-UHFFFAOYSA-N Fc1ccccc1N(c(cc1C23c(cccc4)c4-c4ccccc24)ccc1-c(c1ccccc11)c3cc1N(c1ccccc1-c1ccccc1)c(cccc1)c1F)c(cccc1)c1-c1ccccc1 Chemical compound Fc1ccccc1N(c(cc1C23c(cccc4)c4-c4ccccc24)ccc1-c(c1ccccc11)c3cc1N(c1ccccc1-c1ccccc1)c(cccc1)c1F)c(cccc1)c1-c1ccccc1 HJHDNWCDIJTMGE-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000005108 dry cleaning Methods 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- PSBAIJVSCTZDDB-UHFFFAOYSA-N phenyl acetylsalicylate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 PSBAIJVSCTZDDB-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- DLXBGTIGAIESIG-UHFFFAOYSA-N 1,8-dibromonaphthalene Chemical compound C1=CC(Br)=C2C(Br)=CC=CC2=C1 DLXBGTIGAIESIG-UHFFFAOYSA-N 0.000 description 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 1
- OILLJMJVFMGJGD-UHFFFAOYSA-N Clc(cc1C2(c(cccc3)c3-c3c2cccc3)c2cccc3c22)ccc1-c2ccc3Br Chemical compound Clc(cc1C2(c(cccc3)c3-c3c2cccc3)c2cccc3c22)ccc1-c2ccc3Br OILLJMJVFMGJGD-UHFFFAOYSA-N 0.000 description 1
- IVYDYYGKJIVLPE-UHFFFAOYSA-N FC(c(cc1)ccc1N(c(cc1)ccc1F)c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1ccc(C(F)(F)F)cc1)c(cc1)ccc1F)(F)F Chemical compound FC(c(cc1)ccc1N(c(cc1)ccc1F)c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1ccc(C(F)(F)F)cc1)c(cc1)ccc1F)(F)F IVYDYYGKJIVLPE-UHFFFAOYSA-N 0.000 description 1
- ZKCJXNYWXCBUFV-UHFFFAOYSA-N FC(c(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1ccc(C(F)(F)F)cc1)c(cccc1)c1F)c(cccc1)c1F)(F)F Chemical compound FC(c(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1ccc(C(F)(F)F)cc1)c(cccc1)c1F)c(cccc1)c1F)(F)F ZKCJXNYWXCBUFV-UHFFFAOYSA-N 0.000 description 1
- GTCLIKFVMDJTSN-UHFFFAOYSA-N FC(c(cccc1)c1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1c(C(F)(F)F)cccc1)c1c(cccc2)c2ccc1)c1cccc2c1cccc2)(F)F Chemical compound FC(c(cccc1)c1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1c(C(F)(F)F)cccc1)c1c(cccc2)c2ccc1)c1cccc2c1cccc2)(F)F GTCLIKFVMDJTSN-UHFFFAOYSA-N 0.000 description 1
- IKORHHMIRIFCLK-UHFFFAOYSA-N FC(c(cccc1)c1N(c(cc1C23c(cccc4)c4-c4ccccc24)ccc1-c(c1ccccc11)c3cc1N(c1ccccc1C(F)(F)F)c1c(cccc2)c2ccc1)c1cccc2c1cccc2)(F)F Chemical compound FC(c(cccc1)c1N(c(cc1C23c(cccc4)c4-c4ccccc24)ccc1-c(c1ccccc11)c3cc1N(c1ccccc1C(F)(F)F)c1c(cccc2)c2ccc1)c1cccc2c1cccc2)(F)F IKORHHMIRIFCLK-UHFFFAOYSA-N 0.000 description 1
- JZPDISJMEKJTJS-UHFFFAOYSA-N FC(c1cc(C(F)(F)F)cc(N(c(cc2C34c5ccccc5-c5c3cccc5)ccc2-c(c2ccccc22)c4cc2N(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccccc2-c2ccccc2)c(cccc2)c2-c2ccccc2)c1)(F)F Chemical compound FC(c1cc(C(F)(F)F)cc(N(c(cc2C34c5ccccc5-c5c3cccc5)ccc2-c(c2ccccc22)c4cc2N(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2ccccc2-c2ccccc2)c(cccc2)c2-c2ccccc2)c1)(F)F JZPDISJMEKJTJS-UHFFFAOYSA-N 0.000 description 1
- IUWQSBGFISRXMM-UHFFFAOYSA-N FC(c1cc(N(c(cc2C3(c4ccccc4-c4ccccc34)c3cccc4c33)ccc2-c3ccc4N(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2c(cccc3)c3ccc2)c2cccc3c2cccc3)cc(C(F)(F)F)c1)(F)F Chemical compound FC(c1cc(N(c(cc2C3(c4ccccc4-c4ccccc34)c3cccc4c33)ccc2-c3ccc4N(c2cc(C(F)(F)F)cc(C(F)(F)F)c2)c2c(cccc3)c3ccc2)c2cccc3c2cccc3)cc(C(F)(F)F)c1)(F)F IUWQSBGFISRXMM-UHFFFAOYSA-N 0.000 description 1
- IXLIZXZBGLQQPZ-UHFFFAOYSA-N FC(c1cc(N(c2ccccc2)c(cc2C34c(cccc5)c5-c5ccccc35)ccc2-c(c2ccccc22)c4cc2N(c2ccccc2)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc(C(F)(F)F)c1)(F)F Chemical compound FC(c1cc(N(c2ccccc2)c(cc2C34c(cccc5)c5-c5ccccc35)ccc2-c(c2ccccc22)c4cc2N(c2ccccc2)c2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc(C(F)(F)F)c1)(F)F IXLIZXZBGLQQPZ-UHFFFAOYSA-N 0.000 description 1
- OUOHODOXGCSFEB-UHFFFAOYSA-N FC(c1ccccc1N(c(cc1)ccc1F)c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(c1ccccc11)c3cc1N(c(cc1)ccc1F)c1c(C(F)(F)F)cccc1)(F)F Chemical compound FC(c1ccccc1N(c(cc1)ccc1F)c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(c1ccccc11)c3cc1N(c(cc1)ccc1F)c1c(C(F)(F)F)cccc1)(F)F OUOHODOXGCSFEB-UHFFFAOYSA-N 0.000 description 1
- YQTDEMGWQKWXRG-UHFFFAOYSA-N FC(c1ccccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1c(C(F)(F)F)cccc1)c(cccc1)c1-c1ccccc1)c(cccc1)c1-c1ccccc1)(F)F Chemical compound FC(c1ccccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1c(C(F)(F)F)cccc1)c(cccc1)c1-c1ccccc1)c(cccc1)c1-c1ccccc1)(F)F YQTDEMGWQKWXRG-UHFFFAOYSA-N 0.000 description 1
- FRDKQXNQBDWHTH-UHFFFAOYSA-N FC(c1ccccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1c(C(F)(F)F)cccc1)c(cccc1)c1F)c(cccc1)c1F)(F)F Chemical compound FC(c1ccccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1c(C(F)(F)F)cccc1)c(cccc1)c1F)c(cccc1)c1F)(F)F FRDKQXNQBDWHTH-UHFFFAOYSA-N 0.000 description 1
- GRGYFLFQWKROHW-UHFFFAOYSA-N Fc(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1F)c1c(cccc2)c2ccc1)c1cccc2c1cccc2 Chemical compound Fc(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1F)c1c(cccc2)c2ccc1)c1cccc2c1cccc2 GRGYFLFQWKROHW-UHFFFAOYSA-N 0.000 description 1
- IXKCFOKTBKLBLD-UHFFFAOYSA-N Fc(cccc1)c1N(c(cc1)cc(C23c4ccccc4-c4c2cccc4)c1-c(c1c2cccc1)c3cc2N(c1cc2ccccc2cc1)c1ccccc1F)c1ccc(cccc2)c2c1 Chemical compound Fc(cccc1)c1N(c(cc1)cc(C23c4ccccc4-c4c2cccc4)c1-c(c1c2cccc1)c3cc2N(c1cc2ccccc2cc1)c1ccccc1F)c1ccc(cccc2)c2c1 IXKCFOKTBKLBLD-UHFFFAOYSA-N 0.000 description 1
- JJUGJWSKZLRPJG-UHFFFAOYSA-N Fc(cccc1)c1Nc(cc1)ccc1S Chemical compound Fc(cccc1)c1Nc(cc1)ccc1S JJUGJWSKZLRPJG-UHFFFAOYSA-N 0.000 description 1
- OASCJSBEYSNXMR-UHFFFAOYSA-N Fc1ccccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1ccccc1-c1ccccc1)c(cccc1)c1F)c(cccc1)c1-c1ccccc1 Chemical compound Fc1ccccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1ccccc1-c1ccccc1)c(cccc1)c1F)c(cccc1)c1-c1ccccc1 OASCJSBEYSNXMR-UHFFFAOYSA-N 0.000 description 1
- MMAINNRYYZFXLJ-UHFFFAOYSA-N Fc1ccccc1N(c1ccccc1)c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1ccccc1)c(cccc1)c1F Chemical compound Fc1ccccc1N(c1ccccc1)c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1ccccc1)c(cccc1)c1F MMAINNRYYZFXLJ-UHFFFAOYSA-N 0.000 description 1
- UYKCBMANWHRUSK-UHFFFAOYSA-N N#Cc(cc1)ccc1N(c(cc1)ccc1F)c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(c1c2cccc1)c3cc2N(c(cc1)ccc1C#N)c(cc1)ccc1F Chemical compound N#Cc(cc1)ccc1N(c(cc1)ccc1F)c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(c1c2cccc1)c3cc2N(c(cc1)ccc1C#N)c(cc1)ccc1F UYKCBMANWHRUSK-UHFFFAOYSA-N 0.000 description 1
- BAKYNZKGDAXZTQ-UHFFFAOYSA-N N#Cc(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1C#N)c(cccc1)c1-c1ccccc1)c(cccc1)c1-c1ccccc1 Chemical compound N#Cc(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1C#N)c(cccc1)c1-c1ccccc1)c(cccc1)c1-c1ccccc1 BAKYNZKGDAXZTQ-UHFFFAOYSA-N 0.000 description 1
- SSESIDMFZGHNGV-UHFFFAOYSA-N N#Cc(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1C#N)c(cccc1)c1F)c(cccc1)c1F Chemical compound N#Cc(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1C#N)c(cccc1)c1F)c(cccc1)c1F SSESIDMFZGHNGV-UHFFFAOYSA-N 0.000 description 1
- GRPFCLDDNUJLQQ-UHFFFAOYSA-N N#Cc(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1C#N)c1cc(cccc2)c2cc1)c1cc2ccccc2cc1 Chemical compound N#Cc(cc1)ccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1C#N)c1cc(cccc2)c2cc1)c1cc2ccccc2cc1 GRPFCLDDNUJLQQ-UHFFFAOYSA-N 0.000 description 1
- JIUHDLOLPBIAEB-UHFFFAOYSA-N N#Cc(cc1)ccc1N(c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(c1c2cccc1)c3cc2N(c(cc1)ccc1C#N)c1cccc(C#N)c1)c1cccc(C#N)c1 Chemical compound N#Cc(cc1)ccc1N(c(cc1C23c4ccccc4-c4ccccc24)ccc1-c(c1c2cccc1)c3cc2N(c(cc1)ccc1C#N)c1cccc(C#N)c1)c1cccc(C#N)c1 JIUHDLOLPBIAEB-UHFFFAOYSA-N 0.000 description 1
- URRIMMDSCAUAEJ-UHFFFAOYSA-N N#Cc(cc1)ccc1N(c1ccc(C(F)(F)F)cc1)c(cc1C23c4ccccc4-c4c2cccc4)ccc1-c(c1c2cccc1)c3cc2N(c1ccc(C(F)(F)F)cc1)c(cc1)ccc1C#N Chemical compound N#Cc(cc1)ccc1N(c1ccc(C(F)(F)F)cc1)c(cc1C23c4ccccc4-c4c2cccc4)ccc1-c(c1c2cccc1)c3cc2N(c1ccc(C(F)(F)F)cc1)c(cc1)ccc1C#N URRIMMDSCAUAEJ-UHFFFAOYSA-N 0.000 description 1
- CDJDZWDNBFIGKY-UHFFFAOYSA-N N#Cc(cc1)ccc1Nc1ccccc1 Chemical compound N#Cc(cc1)ccc1Nc1ccccc1 CDJDZWDNBFIGKY-UHFFFAOYSA-N 0.000 description 1
- JOOPLYMJIDGRCS-UHFFFAOYSA-N N#Cc(cccc1)c1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1c(C(F)(F)F)cccc1)c(cccc1)c1C#N)c1ccccc1C(F)(F)F Chemical compound N#Cc(cccc1)c1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c1c(C(F)(F)F)cccc1)c(cccc1)c1C#N)c1ccccc1C(F)(F)F JOOPLYMJIDGRCS-UHFFFAOYSA-N 0.000 description 1
- PPJPBHJGLDOUKI-UHFFFAOYSA-N N#Cc(cccc1)c1N(c(cc1C23c(cccc4)c4-c4ccccc24)ccc1-c(c1ccccc11)c3cc1N(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1ccccc1C#N)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 Chemical compound N#Cc(cccc1)c1N(c(cc1C23c(cccc4)c4-c4ccccc24)ccc1-c(c1ccccc11)c3cc1N(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1ccccc1C#N)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 PPJPBHJGLDOUKI-UHFFFAOYSA-N 0.000 description 1
- KVITXDHOXVXUHN-UHFFFAOYSA-N N#Cc(cccc1)c1N(c(cc1C23c4ccccc4-c4c2cccc4)ccc1-c(c1ccccc11)c3cc1N(c1ccccc1C#N)c(cccc1)c1C#N)c1ccccc1C#N Chemical compound N#Cc(cccc1)c1N(c(cc1C23c4ccccc4-c4c2cccc4)ccc1-c(c1ccccc11)c3cc1N(c1ccccc1C#N)c(cccc1)c1C#N)c1ccccc1C#N KVITXDHOXVXUHN-UHFFFAOYSA-N 0.000 description 1
- MWCCBTDXTWGAPK-UHFFFAOYSA-N N#Cc1cc(Nc(cccc2)c2F)ccc1 Chemical compound N#Cc1cc(Nc(cccc2)c2F)ccc1 MWCCBTDXTWGAPK-UHFFFAOYSA-N 0.000 description 1
- TWSNUBWLKTWTGK-UHFFFAOYSA-N N#Cc1cccc(N(c(cc2)ccc2F)c(cc2C3(c4ccccc4-c4ccccc34)c3cccc4c33)ccc2-c3ccc4N(c(cc2)ccc2F)c2cc(C#N)ccc2)c1 Chemical compound N#Cc1cccc(N(c(cc2)ccc2F)c(cc2C3(c4ccccc4-c4ccccc34)c3cccc4c33)ccc2-c3ccc4N(c(cc2)ccc2F)c2cc(C#N)ccc2)c1 TWSNUBWLKTWTGK-UHFFFAOYSA-N 0.000 description 1
- JSCCTIBQWSLYPH-UHFFFAOYSA-N N#Cc1ccccc1N(c(cc1)ccc1F)c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1F)c(cccc1)c1C#N Chemical compound N#Cc1ccccc1N(c(cc1)ccc1F)c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cc1)ccc1F)c(cccc1)c1C#N JSCCTIBQWSLYPH-UHFFFAOYSA-N 0.000 description 1
- UKXBHKKGTXMUDL-UHFFFAOYSA-N N#Cc1ccccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cccc1)c1C#N)c(cccc1)c1F)c(cccc1)c1F Chemical compound N#Cc1ccccc1N(c(cc1C2(c3ccccc3-c3ccccc23)c2cccc3c22)ccc1-c2ccc3N(c(cccc1)c1C#N)c(cccc1)c1F)c(cccc1)c1F UKXBHKKGTXMUDL-UHFFFAOYSA-N 0.000 description 1
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/59—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- 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
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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
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
Definitions
- the present invention relates to a spiro-type organic material and an organic electroluminescent device using the same, and more particularly, a spiro-type organic material which can obtain a short wavelength light emission that can be used for an organic electroluminescent device, which is a kind of display, with high efficiency. And it relates to an organic electroluminescent device using the same.
- Organic semiconductors are being developed for numerous types of electronic equipment applications.
- the organic electroluminescent device is simpler in structure than other flat panel display devices such as liquid crystal display (LCD), plasma display panel (PDP) and field emission display (FED), has various advantages in manufacturing process, and has high luminance and viewing angle. Due to its excellent characteristics, fast response speed and low driving voltage, development is being actively conducted to be used as a light source for a flat panel display such as a wall-mounted TV or a back light of a display, an illumination, a billboard.
- LCD liquid crystal display
- PDP plasma display panel
- FED field emission display Due to its excellent characteristics, fast response speed and low driving voltage, development is being actively conducted to be used as a light source for a flat panel display such as a wall-mounted TV or a back light of a display, an illumination, a billboard.
- an organic electroluminescent device recombines holes injected from an anode and electrons injected from a cathode when a DC voltage is applied to form an exciton, an electron-hole pair, and is converted into light by transferring energy of the excitons to a light emitting material.
- spiro-type compounds are known to have excellent thermal stability and device properties.
- a material having a blue light emitting layer in a short wavelength region using a spiro form of the compound there is no report on a material having a blue light emitting layer in a short wavelength region using a spiro form of the compound.
- the present inventors completed the present invention by finding that a compound having an asymmetric spiro form could solve the above problems while studying an aromatic compound capable of obtaining light emission of short wavelength with high efficiency.
- the present invention is to provide a spiro-type organic material and an organic electroluminescent device using the same, which can obtain light emission of short wavelength with high efficiency.
- the present invention provides a compound represented by the following formula (1).
- R 1 is phenyl, said phenyl is unsubstituted or substituted with one or two substituents independently selected from the group consisting of halogen, C 1-4 haloalkyl, cyano, phenyl and trimethylsilyl,
- R 2 is phenyl or naphthyl, said phenyl is substituted with one or two substituents independently selected from the group consisting of halogen, C 1-4 haloalkyl, cyano and trimethylsilyl.
- the compound represented by the formula (1) has a structure of spiro [benzo [c] fluorene-7,9'-fluorene] (spiro [benzo [c] fluorene-7,9'-fluorene]), It is more robust and harder to crystallize than conventional spyrophoric compounds. In addition, it has an asymmetric structure, and the secondary amine derivative is substituted, it is characterized in that the blue light emission is possible.
- R 1 is phenyl and the phenyl is unsubstituted or substituted with one or two substituents independently selected from the group consisting of fluoro, trifluoromethyl, cyano, phenyl and trimethylsilyl do.
- the phenyl is substituted with any one substituent selected from the group consisting of fluoro, trifluoromethyl, cyano, phenyl and trimethylsilyl.
- the phenyl is substituted with two trifluoromethyls.
- R 2 is phenyl and the phenyl is substituted with any one or two substituents independently selected from the group consisting of fluoro, trifluoromethyl, cyano and trimethylsilyl.
- the phenyl is substituted with any substituent selected from the group consisting of fluoro, trifluoromethyl, cyano and trimethylsilyl.
- the phenyl is substituted with two trifluoromethyls.
- the present invention provides a method for producing a compound represented by the formula (1), as shown in Scheme 1-1.
- R 1 and R 2 are as defined above.
- Step 1 is a step of preparing a compound represented by Chemical Formula 1 by reacting the compound represented by Chemical Formula 1-2 with the compound represented by Chemical Formula 1-3.
- Toluene may be used as the solvent, and the reaction is preferably performed in the presence of palladium acetate (II), tri-t-butylphosphine, sodium t-butoxide, and the like.
- the compound represented by Chemical Formula 1-2 may be prepared as, for example, the following Scheme 1-2, and in the present invention, the compound represented by Chemical Formula 1-2 in the following Preparation Example was used.
- the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
- the present invention also provides an organic electroluminescent device in which an organic thin film layer composed of a single layer or a plurality of layers including at least one light emitting layer is sandwiched between a cathode and an anode, wherein at least one layer of the organic thin film layer is represented by Chemical Formula 1
- An organic electroluminescent device comprising an organic light emitting device comprising a compound is provided.
- the present invention provides a compound represented by the following formula (2).
- R 1 is phenyl, said phenyl is unsubstituted or substituted with one or two substituents independently selected from the group consisting of halogen, C 1-4 haloalkyl, cyano, phenyl and trimethylsilyl,
- R 2 is phenyl or naphthyl, said phenyl is substituted with one or two substituents independently selected from the group consisting of halogen, C 1-4 haloalkyl, cyano and trimethylsilyl.
- the compound represented by the formula (2) has a structure of spiro [benzo [de] anthracene-7,9'-fluorene] (spiro [benzo [de] anthracene-7,9'-fluorene]), and As a spy, the structure of the compound is more robust and difficult to crystallize. In addition, it has an asymmetric structure, and the secondary amine derivative is substituted, it is characterized in that the blue light emission is possible.
- R 1 is phenyl and the phenyl is unsubstituted or substituted with one or two substituents independently selected from the group consisting of fluoro, trifluoromethyl, cyano, phenyl and trimethylsilyl do.
- the phenyl is substituted with any one substituent selected from the group consisting of fluoro, trifluoromethyl, cyano, phenyl and trimethylsilyl.
- the phenyl is substituted with two trifluoromethyls.
- R 2 is phenyl and the phenyl is substituted with any one or two substituents independently selected from the group consisting of fluoro, trifluoromethyl, cyano and trimethylsilyl.
- the phenyl is substituted with any substituent selected from the group consisting of fluoro, trifluoromethyl, cyano and trimethylsilyl.
- the phenyl is substituted with two trifluoromethyls.
- the present invention provides a method for producing a compound represented by the formula (2), for example, Reaction Scheme 2-1.
- R 1 and R 2 are as defined above.
- Step 1 is a step of preparing a compound represented by Chemical Formula 2 by reacting the compound represented by Chemical Formula 2-2 with the compound represented by Chemical Formula 2-3.
- Toluene may be used as the solvent, and the reaction is preferably performed in the presence of palladium acetate (II), BINAP (2,2'-bis (diphenylphosphino) -1,1'-binaphthyl), sodium t-butoxide and the like.
- the compound represented by Chemical Formula 2-2 may be prepared, for example, as in Scheme 2-2.
- the compound represented by Chemical Formula 2-2 is used in the following Preparation Example.
- the present invention also provides an organic light emitting device comprising the compound represented by the formula (2).
- the present invention is an organic electroluminescent device in which an organic thin film layer consisting of a single layer or a plurality of layers including at least one light emitting layer is sandwiched between a cathode and an anode, wherein at least one layer of the organic thin film layer is represented by the formula (2)
- An organic electroluminescent device comprising an organic light emitting device comprising a compound is provided.
- the compound of the spiro structure and the organic electroluminescent device using the same according to the present invention can obtain a short wavelength of light emission with high efficiency, and can be applied to various organic electroluminescent devices such as flat panel displays such as wall-mounted TVs, lighting or back light of displays. Can be used.
- 4-aminobenzonitrile (15 g) was added to a 2 L three-necked round bottom flask and stirred for 30 minutes under an argon atmosphere. After stirring for 30 minutes, bromobenzene (18.1 g) was added, dissolved in toluene (1 L), tris (dibenzylideneacetone) dipalladium (0) (1.06g), and tri-t-butylphosphine (0.23 g). , Sodium-t-butoxide (24.4 g) was added thereto and stirred at reflux for 18 hours. Filtration in hot state, the solid on the filter was washed with hot toluene, dichloromethane and the filtrate was concentrated under reduced pressure.
- reaction solution was extracted with water and methylene chloride, dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent.
- Example 2 to 76 The compound of Example 2 to 76 was prepared in the same manner as in Example 1, using Intermediates 2-2 to 2-76 instead of Intermediate 2-1. Structures and NMR data of Examples 2 to 76, respectively, are shown in Tables 6 to 20 below.
- the ITO transparent electrode having a thin film thickness of 100 nm was 40 mm ⁇ 40 mm ⁇ 0.7 m in size, and the substrate was ultrasonically cleaned in a distilled shoe in which detergent was dissolved for 10 minutes, and washed twice in distilled water for 10 minutes.
- a layer of a compound represented by the following formula (B) capable of hole transport on the compound layer represented by the formula (A) was formed by vacuum deposition at 80 nm.
- Example 1 of the present invention was mixed and deposited at a concentration of 5% as a blue dopant together with the compound represented by the following Formula C as a light emitting host on the compound layer represented by Formula B to form a light emitting layer having a thickness of 20 nm.
- a compound represented by the following Formula D which serves to inject and transport electrons on the emission layer, was vacuum deposited to a thickness of 25 nm.
- LiF lithium fluoride
- 120 nm thick aluminum were sequentially deposited on the electron injection and transport layer to form a cathode.
- the organic electroluminescent device was manufactured by the same method as Experimental Example 1, except that the compound of Example 10 was used instead of the compound of Example 1, which is a light emitting dopant material.
- the organic electroluminescent device was manufactured by the same method as Experimental Example 1, except that the compound of Example 71 was used instead of the compound of Example 1, which is a light emitting dopant material.
- the organic electroluminescent device was manufactured by the same method as Experimental Example 1, but using a compound represented by the following Formula E instead of the compound of Example 1, which is a light emitting dopant material.
- 1,8-dibromonaphthalene 50 g
- 4-chlorophenylboronic acid 30.1 g
- toluene 500 mL
- potassium carbonate 132.9 g
- water 250 mL
- Tetrakis (triphenylphosphine) palladium (0) 2.22 g
- the reaction solution was cooled to room temperature and extracted twice with ethyl acetate.
- the organic layer was dried over magnesium sulfate and concentrated under reduced pressure to remove the solvent.
- the material produced by concentration was separated by column using hexane and washed with methanol to obtain 35 g of a white powder.
- intermediate 1-4 (33.5 g) was added to 335 mL of carbon tetrachloride, and the mixture was stirred until it was completely dissolved. After confirming that intermediate 1-4 was completely dissolved, bromine (13.4 mL) was added thereto, and the mixture was refluxed for 72 hours. After completion of the reaction, the mixture was filtered under reduced pressure at room temperature, washed with an aqueous sodium hydroxide solution, and the filtered solid was vacuum dried to obtain 40.1 g of Intermediate 1.
- Example 2 to 76 The compound of Example 2 to 76 was prepared in the same manner as in Example 1, using Intermediates 2-2 to 2-76 instead of Intermediate 2-1. Structures and NMR data of the prepared Examples 2 to 76 are shown in Tables 21 to 35, respectively.
- the ITO transparent electrode having a thin film thickness of 100 nm was 40 mm ⁇ 40 mm ⁇ 0.7 m in size, and the substrate was ultrasonically cleaned in a distilled shoe in which detergent was dissolved for 10 minutes, and washed twice in distilled water for 10 minutes.
- a layer of a compound represented by the following formula (B) capable of hole transport on the compound layer represented by the formula (A) was formed by vacuum deposition at 80 nm.
- Example 1 of the present invention was mixed and deposited at a concentration of 5% as a blue dopant together with the compound represented by the following Formula C as a light emitting host on the compound layer represented by Formula B to form a light emitting layer having a thickness of 20 nm.
- a compound represented by the following Formula D which serves to inject and transport electrons on the emission layer, was vacuum deposited to a thickness of 25 nm.
- LiF lithium fluoride
- 120 nm thick aluminum were sequentially deposited on the electron injection and transport layer to form a cathode.
- the organic electroluminescent device was manufactured by the same method as Experimental Example 1, except that the compound of Example 10 was used instead of the compound of Example 1, which is a light emitting dopant material.
- the organic electroluminescent device was manufactured by the same method as Experimental Example 1, except that the compound of Example 71 was used instead of the compound of Example 1, which is a light emitting dopant material.
- the organic electroluminescent device was manufactured by the same method as Experimental Example 1, but using a compound represented by the following Formula E instead of the compound of Example 1, which is a light emitting dopant material.
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- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La présente invention concerne un matériau organique de type spiro et un dispositif électroluminescent organique le mettant en œuvre. Plus particulièrement, l'invention concerne un matériau organique de type spiro et un dispositif électroluminescent organique le mettant en œuvre assurant l'obtention d'une luminescence à ondes courtes hautement efficace.
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KR20120112611A KR101482632B1 (ko) | 2012-10-10 | 2012-10-10 | 스파이로형 유기 재료 및 이를 이용한 유기 전기발광 소자 |
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KR20120112610A KR101490446B1 (ko) | 2012-10-10 | 2012-10-10 | 스파이로형 유기 재료 및 이를 이용한 유기 전기발광 소자 |
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WO2016131521A1 (fr) * | 2015-02-16 | 2016-08-25 | Merck Patent Gmbh | Matériaux à base de dérivés de spirobifluorène pour dispositifs électroniques |
WO2016137148A1 (fr) * | 2015-02-27 | 2016-09-01 | 덕산네오룩스 주식회사 | Nouveau composé pour élément électronique organique, élément électronique organique utilisant ce composé et dispositif électronique associé |
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WO2016129861A1 (fr) * | 2015-02-09 | 2016-08-18 | 덕산네오룩스 주식회사 | Nouveau composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit composé |
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WO2016137148A1 (fr) * | 2015-02-27 | 2016-09-01 | 덕산네오룩스 주식회사 | Nouveau composé pour élément électronique organique, élément électronique organique utilisant ce composé et dispositif électronique associé |
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US10411191B2 (en) | 2016-09-20 | 2019-09-10 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
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