WO2017111544A1 - 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 - Google Patents
유기 화합물 및 이를 포함하는 유기 전계 발광 소자 Download PDFInfo
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- WO2017111544A1 WO2017111544A1 PCT/KR2016/015200 KR2016015200W WO2017111544A1 WO 2017111544 A1 WO2017111544 A1 WO 2017111544A1 KR 2016015200 W KR2016015200 W KR 2016015200W WO 2017111544 A1 WO2017111544 A1 WO 2017111544A1
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- WO
- WIPO (PCT)
- Prior art keywords
- group
- aryl
- groups
- alkyl
- boron
- Prior art date
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- 150000002894 organic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 125000003118 aryl group Chemical group 0.000 claims description 176
- 125000000217 alkyl group Chemical group 0.000 claims description 114
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 98
- 125000001072 heteroaryl group Chemical group 0.000 claims description 72
- 125000003545 alkoxy group Chemical group 0.000 claims description 67
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 67
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 67
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 66
- 125000000304 alkynyl group Chemical group 0.000 claims description 66
- 125000004104 aryloxy group Chemical group 0.000 claims description 66
- 125000004429 atom Chemical group 0.000 claims description 64
- 125000003342 alkenyl group Chemical group 0.000 claims description 62
- 125000005264 aryl amine group Chemical group 0.000 claims description 62
- 125000001424 substituent group Chemical group 0.000 claims description 62
- 125000005104 aryl silyl group Chemical group 0.000 claims description 60
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 47
- 229910052805 deuterium Inorganic materials 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
- -1 alkyl boron Chemical compound 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 39
- 239000000126 substance Substances 0.000 claims description 31
- 239000011368 organic material Substances 0.000 claims description 28
- 229910052796 boron Inorganic materials 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 21
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 21
- 125000000061 phosphanyl group Chemical group [H]P([H])* 0.000 claims description 19
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 18
- 239000008280 blood Substances 0.000 claims description 18
- 210000004369 blood Anatomy 0.000 claims description 18
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical group CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 18
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 230000005525 hole transport Effects 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 150000004982 aromatic amines Chemical class 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000001336 alkenes Chemical group 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 239000010410 layer Substances 0.000 abstract description 104
- 239000012044 organic layer Substances 0.000 abstract description 24
- 230000002708 enhancing effect Effects 0.000 abstract 1
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- 238000003786 synthesis reaction Methods 0.000 description 81
- 239000000463 material Substances 0.000 description 50
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- 230000000052 comparative effect Effects 0.000 description 22
- 239000012153 distilled water Substances 0.000 description 21
- 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 19
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
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- 239000011734 sodium Substances 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 11
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- 238000003756 stirring Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 8
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- NFBOHOGPQUYFRF-UHFFFAOYSA-N oxanthrene Chemical compound C1=CC=C2OC3=CC=CC=C3OC2=C1 NFBOHOGPQUYFRF-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- 238000004506 ultrasonic cleaning Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- MDYDGUOQFUQOGE-UHFFFAOYSA-N 2-methylpropanethioic acid S-[7-oxo-7-[(4-phenyl-2-thiazolyl)amino]heptyl] ester Chemical compound S1C(NC(=O)CCCCCCSC(=O)C(C)C)=NC(C=2C=CC=CC=2)=C1 MDYDGUOQFUQOGE-UHFFFAOYSA-N 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 4
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- GSUCEGNAROQSGU-UHFFFAOYSA-N 2-bromodibenzo-p-dioxin Chemical compound C1=CC=C2OC3=CC(Br)=CC=C3OC2=C1 GSUCEGNAROQSGU-UHFFFAOYSA-N 0.000 description 3
- MCNFSXSJNZPTGE-UHFFFAOYSA-N 2-dibenzo-p-dioxin-2-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(OC=2C(=CC=CC=2)O2)C2=C1 MCNFSXSJNZPTGE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- BEBLXYZXQGRFKD-UHFFFAOYSA-N [4-(4-phenyl-n-(4-phenylphenyl)anilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(C=2C=CC=CC=2)C=C1 BEBLXYZXQGRFKD-UHFFFAOYSA-N 0.000 description 3
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- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 3
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
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- 125000005605 benzo group Chemical group 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- 229910052804 chromium Inorganic materials 0.000 description 1
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- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 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
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- DSSBJZCMMKRJTF-UHFFFAOYSA-N dibenzofuran-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3OC2=C1 DSSBJZCMMKRJTF-UHFFFAOYSA-N 0.000 description 1
- ZXHUJRZYLRVVNP-UHFFFAOYSA-N dibenzofuran-4-ylboronic acid Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2B(O)O ZXHUJRZYLRVVNP-UHFFFAOYSA-N 0.000 description 1
- CSLSCVHILGCSTE-UHFFFAOYSA-N dibenzothiophen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3SC2=C1 CSLSCVHILGCSTE-UHFFFAOYSA-N 0.000 description 1
- GOXNHPQCCUVWRO-UHFFFAOYSA-N dibenzothiophen-4-ylboronic acid Chemical compound C12=CC=CC=C2SC2=C1C=CC=C2B(O)O GOXNHPQCCUVWRO-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
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- 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
- 230000005281 excited state Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- BIFARHLBYAKSSN-UHFFFAOYSA-N methyl 2-bromo-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1Br BIFARHLBYAKSSN-UHFFFAOYSA-N 0.000 description 1
- BIECSXCXIXHDBC-UHFFFAOYSA-N methyl 2-bromo-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1Br BIECSXCXIXHDBC-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl 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
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/24—[b,e]-condensed with two six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/10—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 two hetero rings linked by a carbon chain containing aromatic 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
-
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Definitions
- the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
- the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
- a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB hole blocking layer
- BCP hole blocking layer
- electron transporting layer material anthracene derivatives have been reported as the light emitting layer material.
- metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
- the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.
- an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
- the present invention provides a compound represented by the following formula (1):
- At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 is condensed with a ring represented by the following formula (2) To form a condensed ring;
- R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group , C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphanyl group, C 6 ⁇ C 60 mono or diaryl
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- the dotted line means the part where condensation takes place
- Y 1 to Y 12 are each independently N or C (R 9 );
- R 9 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha
- a condensed ring may be formed by combining with or adjacent to a group selected from the group consisting of a silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60
- the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
- adjacent groups are adjacent to each other, such as R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , or R 7 and R 8, and the like. It means a substituent substituted on the carbon present.
- Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
- Alkenyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
- Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
- Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
- monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom for example, may have 8 to 60 carbon atoms
- the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity).
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycides such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl Click ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
- R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
- cycloalkyl in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
- examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- Heterocycloalkyl in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
- heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
- Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
- the compound of the present invention has excellent thermal stability, carrier transporting ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
- the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspect of light emission performance, driving voltage, lifespan, efficiency, etc. is greatly improved.
- the present invention provides a compound represented by Formula 1:
- At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 is condensed with a ring represented by the following formula (2) To form a condensed ring;
- R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group , C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphanyl group, C 6 ⁇ C 60 mono or diaryl
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- the dotted line means the part where condensation takes place
- Y 1 to Y 12 are each independently N or C (R 9 );
- R 9 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha
- a condensed ring may be formed by combining with or adjacent to a group selected from the group consisting of a silyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60
- novel compounds of the present invention have a structure in which a spirofluorene moiety is condensed to dibenzo [b, e] [1,4] dioxine to form a basic skeleton, and various substituents are bonded or condensed to such a basic skeleton. It is characterized by represented by the formula (1):
- At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 are each independently a ring represented by the following formula (2): Condensed to form a condensed ring, wherein at least two of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , and R 7 and R 8 When condensed with a ring represented by Formula 2 to form a condensed ring, the condensed rings are the same as or different from each other;
- R 1 to R 8 which do not form a ring and a condensed ring represented by the following formula (2) are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group , C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphanyl group, C 6 ⁇ C 60 mono or diaryl
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 1 to R 8 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- the dotted line means the part where condensation takes place
- Y 1 to Y 12 are each independently N or C (R 9 );
- R 9 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A condensed ring in combination with a group selected from, or adjacent to, an adjacent group (e.g., other R 9 , which is present adjacent), such as a nil group, a C 6 -C 60 mono or diarylphosphinyl
- the phosphorescent light emitting layer of the organic material layer included in the organic electroluminescent device includes a host and a dopant to increase the color purity and the luminous efficiency.
- the host should have a triplet energy gap higher than the dopant. That is, in order to effectively provide phosphorescence from the dopant, the energy of the lowest excited state of the host must be higher than the energy of the lowest emission state of the dopant.
- the dibenzo [b, e] [1,4] dioxin moiety has a wide singlet energy level and a high triplet energy level.
- an organic material layer (hereinafter, referred to as a 'light emitting auxiliary layer') is formed between the hole transport layer and the light emitting layer by using the compound of Formula 1, or an organic material layer (hereinafter referred to as an 'electron transport auxiliary layer') between the light emitting layer and the electron transporting layer.
- the excitons Since the diffusion of the exciton is prevented by the compound, unlike the conventional organic electroluminescent device that does not include the light emitting auxiliary layer or the electron transporting auxiliary layer, the excitons substantially contribute to light emission in the light emitting layer. The number can be increased to improve the luminous efficiency of the device.
- the compound represented by the formula (1) can be adjusted HOMO and LUMO energy level according to the substituent introduced into the basic skeleton, it can have a wide bandgap and high carrier transport properties.
- the compounds of the present invention have a high electron donating group (EDG) in the base skeleton due to the high hole transport capacity of oxygen atoms in dibenzo [b, e] [1,4] dioxin. When is combined, it can be easily used as a hole transport layer material.
- EWG electron withdrawing group
- the entire molecule may have a bipolar characteristic to increase the binding force between holes and electrons.
- the compound represented by Formula 1 may be a compound represented by any one of the following Formulas 3 to 5, but is not limited thereto:
- Y 1 to Y 12 and R 1 to R 8 are the same as defined in Chemical Formula 1, respectively.
- At least one of Y 1 to Y 4 is C (R 9 ), when there are a plurality of R 9 They are the same or different from each other, R 9 is As defined in formula (2).
- Y 1 to Y 12 are all C (R 9 ), wherein a plurality of R 9 are the same or different from each other, R 9 is in the formula (2) As defined.
- R 9 is preferably a substituent represented by the following formula (6) in terms of luminous efficiency, but is not limited thereto:
- L 1 and L 2 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
- R 10 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A group selected from, or contiguous to, a C 6 -C 60 mono or diarylphosphinyl group and a C 6 -C 60 arylamine group (e.g., L 1 or L 2, or other adjacent R 9 Or R 10, etc.
- the arylene group and heteroarylene group of L 1 and L 2 an alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine of R 10 Group, alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphanyl group, mono or diaryl phosphinyl group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group , C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 60 arylamine group, C 3 to C 40 cycl
- R 10 is composed of hydrogen, deuterium (D), an aryl group of C 6 ⁇ C 60 , a heteroaryl group of 5 to 60 nuclear atoms and an arylamine group of C 6 ⁇ C 60 Can be selected from the group.
- the compound represented by Formula 1 of the present invention may be formed into an organic material layer material of an organic EL device, preferably an emission layer material (blue, green and / or red phosphorescent host material), an electron transport layer / injection layer material, a hole transport layer / When applied as an injection layer material, a light emission auxiliary layer material, or a life improvement layer material, the performance and life characteristics of the organic EL device may be greatly improved. As a result, the organic EL device may maximize the performance of the full color organic light emitting panel.
- L 1 and L 2 are each independently a linker represented by any one of the following formulas 7 to 11 preferably in terms of luminous efficiency, but is not limited thereto:
- X 1 is O, S, N (R 12 ) or C (R 13 ) (R 14 );
- X 2 is N or C (R 15 );
- p is an integer from 0 to 4.
- R 11 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , C 6 -C 60 mono or diarylphosphinyl groups and C 6 -C 60 arylamine groups selected from or adjacent to the group (e.g., L 1 or L 2, or other R
- R 12 to R 15 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of or, or adjacent groups of (for example, L 1 or L 2, Or another
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 11 to R 15 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- R 10 is preferably a substituent represented by any one of the following Chemical Formulas 12 to 14, but is not limited thereto:
- Z 1 to Z 5 are each independently N or C (R 18 );
- T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 19 ) (R 20 ), N (R 21 ), O and S, but not both T 1 and T 2 are single bonds;
- q and r are each independently integers of 0 to 4.
- R 16 and R 17 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ⁇ C 60, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, or
- R 18 to R 21 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to aryl phosphazene group, a mono- or diaryl phosphine of C 6 ⁇ C 60 of the C 60 blood group and a C 6 ⁇ C 60 selected from an aryl silyl group the group consisting of or of, the groups bonded to or adjacent to
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 16 to R 21 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
- the substituents represented by Formula 12 to 14 may be a substituent represented by any one of the following Formula A-1 to A-24, but is not limited thereto:
- t is an integer from 0 to 5
- u is an integer from 0 to 4.
- v is an integer from 0 to 3;
- w is an integer from 0 to 2;
- R 22 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, A C 6 -C 60 mono or diarylphosphinyl group and a C 6 -C 60 arylsilyl group, or an adjacent group (e.g., one of L 1 or L 2 , or another adjacent R 22 Or
- R 16 to R 21 , p and q are the same as defined in Chemical Formulas 12 to 14.
- the R 10 is a substituent represented by the following formula (15) is preferable to increase the luminous efficiency, but is not limited thereto:
- R 23 and R 24 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 selected from the group consisting of aryl silyl, or of, the adjacent groups (e.g., R 23 and R 24 are
- alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group and aryl of R 23 and R 24 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms
- R 23 and R 24 are each independently hydrogen, an alkyl group of C 1 ⁇ C 40 , an aryl group of C 6 ⁇ C 60 , a heteroaryl group of 5 to 60 nuclear atoms and It may be selected from the group consisting of C 6 ⁇ C 60 arylamine group.
- R 23 and R 24 are each independently selected from the group consisting of hydrogen, a phenyl group, a biphenyl group, a terphenyl group, a naphthalenyl group, a fluorenyl group, and a substituent represented by the following formula (16): May be, but is not limited to:
- L 3 is each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
- R 25 and R 26 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3- C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ group is selected from the group consisting of an aryl amine of the C 60 or adjacent (e.
- Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
- the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
- organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
- the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
- the compound may be used alone or mixed two or more.
- the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.
- the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer or a light emitting auxiliary layer.
- the light emitting layer of the organic electroluminescent device may include a host material, and may include a compound represented by Chemical Formula 1 as the host material.
- the compound represented by Chemical Formula 1 when included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.
- the structure of the organic EL device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
- an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer.
- At least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer or the light emitting auxiliary layer It may include a compound represented by the formula (1).
- the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
- the organic EL device of the present invention is a material and method known in the art, except that at least one or more of the organic material layer (for example, the light emitting layer or the light emitting auxiliary layer) is formed to include the compound represented by the formula (1) It can be prepared by forming other organic material layer and electrode using.
- the organic material layer for example, the light emitting layer or the light emitting auxiliary layer
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
- examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
- metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
- Conductive polymers such as polythiophene, poly (3-methylthiophene
- the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
- Methyl 5-chloro-2- (dibenzo [b, e] [1,4] dioxin-2-yl) benzoate (75.4 g, 0.214 mol) obtained in ⁇ Step 2> was added to THF (1 L). After heating, 350 ml of methanesulfonic acid was added, followed by stirring for 4 hours. 500 ml of water was added thereto, and the resulting solid was filtered, washed with 600 ml of water and 200 ml of ethanol and dried to give compound 9-chloro-11H-benzo [b] fluoreno [2,3-e] [1,4] di. Auxin-11-one (53.0 g, yield 78%) was obtained.
- Methyl 5-chloro-2- (dibenzo [b, e] [1,4] dioxin-2-yl) benzoate (75.4 g, 0.214 mol) obtained in ⁇ Step 2> was added to THF (1 L). After heating, 350 ml of methanesulfonic acid was added, followed by stirring for 4 hours. 500 ml of water was added thereto, and the resulting solid was filtered, washed with 600 ml of water and 200 ml of ethanol and dried to give compound 8-chloro-11H-benzo [b] fluoreno [2,3-e] [1,4] di. Auxin-11-one (53.0 g, yield 78%) was obtained.
- a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then the substrate using UV for 5 minutes The substrate was cleaned and transferred to a vacuum evaporator.
- ITO Indium tin oxide
- a green organic electroluminescent device was manufactured in the same manner as in Example 1, except for using the compounds shown in Table 1 below instead of the compounds Cpd148 used in Example 1.
- a green organic EL device was manufactured in the same manner as in Example 1, except that Compound Cpd148, which was used in Example 1, was not used.
- Example 1 Cpd148 6.75 518 41.8
- Example 2 Cpd149 6.80 517 41.5
- Example 3 Cpd150 6.77 518 42.0
- Example 4 Cpd152 6.72 520 41.9
- Example 5 Cpd154 6.80 518 41.5
- Example 6 Cpd155 6.69 520 41.8
- Example 7 Cpd156 6.82 517 41.8
- Example 8 Cpd158 6.75 518 41.8
- Example 9 Cpd179 6.80 520 42.0
- Example 10 Cpd180 6.77 518 42.0 Comparative Example 1 - 6.93 516 38.2
- the green organic electroluminescent devices of Examples 1 to 10 using the compounds represented by Formula 1 according to the present invention (Compounds Cpd148 to Cpd180) as light emitting auxiliary layer materials, only CBP without a light emitting auxiliary layer
- the driving voltage was slightly lower than that of the green organic electroluminescent device of Comparative Example 1, which was used as the light emitting layer material, and the current efficiency was better than that of the green organic electroluminescent device of Comparative Example 1.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, etc.
- UV OZONE cleaner Powersonic 405, Hwasin Tech
- a red organic electroluminescent device was manufactured in the same manner as in Example 11 except for using the compounds shown in Table 2 below instead of the compounds Cpd 148 used in Example 11.
- a red organic electroluminescent device was manufactured in the same manner as in Example 11, except that Compound Cpd 148, which was used in Example 11, was not used.
- Example 11 Sample Luminous auxiliary layer material Driving voltage (V) Current efficiency (cd / A) Example 11 Cpd148 5.13 11.1 Example 12 Cpd149 5.16 11.5 Example 13 Cpd150 5.17 11.6 Example 14 Cpd152 5.14 11.0 Example 15 Cpd154 5.15 10.8 Example 16 Cpd155 5.10 11.2 Example 17 Cpd156 5.15 11.0 Example 18 Cpd158 5.20 11.3 Example 19 Cpd179 5.15 11.0 Example 20 Cpd180 5.10 11.3 Comparative Example 2 - 5.25 8.2
- the red organic electroluminescent devices of Examples 11 to 20 using the compounds represented by Formula 1 according to the present invention (Compounds Cpd148 to Cpd180) as the light emitting auxiliary layer material, CBP only without the light emitting auxiliary layer
- the driving voltage was slightly lower than that of the red organic electroluminescent device of Comparative Example 2 used as the light emitting layer material, and the current efficiency was better.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, and drying was carried out, and then transferred to a UV OZONE cleaner (Powersonic 405, Hwasin Tech).
- the substrate was transferred to the evaporator.
- DS-205 Doosan (80 nm) / NPB (15 nm) / Compound Cpd 148 (15 nm) / ADN + 5% DS-405 (Doosan) (300 nm) / BCP (10 nm
- a blue organic electroluminescent device was manufactured by laminating in order of) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
- the BCP used was as described in Example 1, and the structures of NPB and ADN are as follows.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 21, except for using the compounds shown in Table 3 below instead of the compounds Cpd 148 used in Example 21.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 21, except that Compound Cpd 148, which was used in Example 21, was not used.
- Example 21 Cpd148 5.50 6.9
- Example 22 Cpd149 5.60 6.6
- Example 23 Cpd150 5.55 6.8
- Example 24 Cpd152 5.60 6.9
- Example 25 Cpd154 5.51 6.6
- Example 26 Cpd155 5.55 6.8
- Example 27 Cpd156 5.51 6.0
- Example 28 Cpd158 5.55 6.4
- Example 29 Cpd179 5.60 6.5
- Example 30 Cpd180 5.65 6.8 Comparative Example 3 - 5.60 4.8
- the red organic electroluminescent device of Examples 21 to 30 using the compound represented by Chemical Formula 1 according to the present invention (Compounds Cpd148 to Cpd180) as a light emitting auxiliary layer material, ADN without a light emitting auxiliary layer
- the driving voltage was similar to that of the blue organic electroluminescent device of Comparative Example 3 used as the light emitting layer material, it was found that the current efficiency was superior to that of the organic electroluminescent device of Comparative Example 3.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, and drying
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- M-MTDATA 60 nm) / TCTA (80 nm) / Compound Cpd50 + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF ( 1 nm) / Al (200 nm) was laminated in order to produce an organic electroluminescence.
- a green organic electroluminescent device was manufactured in the same manner as in Example 31, except for using the compounds shown in Table 4 below instead of the compounds Cpd50 used in Example 31.
- a green organic electroluminescent device was manufactured in the same manner as in Example 31, except that CBP was used instead of the compound Cpd50 used as the light emitting host material in forming the emission layer in Example 31.
- Example 31 Cpd50 6.79 517 40.8
- Example 32 Cpd51 6.81 518 41.1
- Example 33 Cpd52 6.79 517 40.8
- Example 34 Cpd53 6.78 515 42.4
- Example 35 Cpd54 6.81 518 41.1
- Example 36 Cpd77 6.79 517 40.8
- Example 37 Cpd83 6.81 518 41.1
- Example 38 Cpd92 6.79 517 40.8
- Example 39 Cpd95 6.79 517 40.8
- Example 40 Cpd96 6.81 518 41.1
- Example 41 Cpd97 6.79 517 40.8
- Example 42 Cpd98 6.79 517 40.8 Comparative Example 4 CBP 6.93 516 38.2
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol, and drying
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- a green organic electroluminescent device was manufactured in the same manner as in Example 43, except for using the compounds shown in Table 5 below instead of the compound Cpd50 used in Example 1.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 43, except for using CBP instead of the compound Cpd50 used as the light emitting host material in forming the emission layer in Example 43.
- the blue organic electroluminescent device of Examples 43 to 47 using the compound (compounds Cpd50 to Cpd54) according to the present invention as a light emitting layer material was a blue organic electroluminescent device of Comparative Example 5 using a conventional CBP. Compared with the current efficiency and driving voltage, it was found to be superior.
- the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
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Abstract
Description
샘플 | 발광보조층 재료 | 구동 전압(V) | 발광 피크(nm) | 전류효율(cd/A) |
실시예 1 | Cpd148 | 6.75 | 518 | 41.8 |
실시예 2 | Cpd149 | 6.80 | 517 | 41.5 |
실시예 3 | Cpd150 | 6.77 | 518 | 42.0 |
실시예 4 | Cpd152 | 6.72 | 520 | 41.9 |
실시예 5 | Cpd154 | 6.80 | 518 | 41.5 |
실시예 6 | Cpd155 | 6.69 | 520 | 41.8 |
실시예 7 | Cpd156 | 6.82 | 517 | 41.8 |
실시예 8 | Cpd158 | 6.75 | 518 | 41.8 |
실시예 9 | Cpd179 | 6.80 | 520 | 42.0 |
실시예 10 | Cpd180 | 6.77 | 518 | 42.0 |
비교예 1 | - | 6.93 | 516 | 38.2 |
샘플 | 발광보조층 재료 | 구동 전압 (V) | 전류효율 (cd/A) |
실시예 11 | Cpd148 | 5.13 | 11.1 |
실시예 12 | Cpd149 | 5.16 | 11.5 |
실시예 13 | Cpd150 | 5.17 | 11.6 |
실시예 14 | Cpd152 | 5.14 | 11.0 |
실시예 15 | Cpd154 | 5.15 | 10.8 |
실시예 16 | Cpd155 | 5.10 | 11.2 |
실시예 17 | Cpd156 | 5.15 | 11.0 |
실시예 18 | Cpd158 | 5.20 | 11.3 |
실시예 19 | Cpd179 | 5.15 | 11.0 |
실시예 20 | Cpd180 | 5.10 | 11.3 |
비교예 2 | - | 5.25 | 8.2 |
샘플 | 발광보조층 재료 | 구동 전압 (V) | 전류효율 (cd/A) |
실시예 21 | Cpd148 | 5.50 | 6.9 |
실시예 22 | Cpd149 | 5.60 | 6.6 |
실시예 23 | Cpd150 | 5.55 | 6.8 |
실시예 24 | Cpd152 | 5.60 | 6.9 |
실시예 25 | Cpd154 | 5.51 | 6.6 |
실시예 26 | Cpd155 | 5.55 | 6.8 |
실시예 27 | Cpd156 | 5.51 | 6.0 |
실시예 28 | Cpd158 | 5.55 | 6.4 |
실시예 29 | Cpd179 | 5.60 | 6.5 |
실시예 30 | Cpd180 | 5.65 | 6.8 |
비교예 3 | - | 5.60 | 4.8 |
샘플 | 호스트 | 구동 전압(V) | 발광 피크(nm) | 전류효율(cd/A) |
실시예 31 | Cpd50 | 6.79 | 517 | 40.8 |
실시예32 | Cpd51 | 6.81 | 518 | 41.1 |
실시예33 | Cpd52 | 6.79 | 517 | 40.8 |
실시예34 | Cpd53 | 6.78 | 515 | 42.4 |
실시예35 | Cpd54 | 6.81 | 518 | 41.1 |
실시예36 | Cpd77 | 6.79 | 517 | 40.8 |
실시예37 | Cpd83 | 6.81 | 518 | 41.1 |
실시예38 | Cpd92 | 6.79 | 517 | 40.8 |
실시예39 | Cpd95 | 6.79 | 517 | 40.8 |
실시예40 | Cpd96 | 6.81 | 518 | 41.1 |
실시예41 | Cpd97 | 6.79 | 517 | 40.8 |
실시예42 | Cpd98 | 6.79 | 517 | 40.8 |
비교예 4 | CBP | 6.93 | 516 | 38.2 |
샘플 | 호스트 | 구동 전압(V) | 발광 피크(nm) | 전류효율(cd/A) |
실시예 43 | Cpd50 | 7.29 | 473 | 6.90 |
실시예 44 | Cpd51 | 7.30 | 474 | 6.34 |
실시예 45 | Cpd52 | 7.24 | 475 | 6.55 |
실시예 46 | Cpd53 | 7.15 | 471 | 6.94 |
실시예 47 | Cpd54 | 7.23 | 472 | 6.25 |
비교예 5 | CBP | 7.80 | 474 | 5.80 |
Claims (13)
- 하기 화학식 1로 표시되는 화합물:[화학식 1]상기 화학식 1에서,R1과 R2, R2와 R3, R3와 R4, R5와 R6, R6와 R7, 및 R7과 R8 중 적어도 하나는 각각 독립적으로 하기 화학식 2로 표시되는 고리와 축합되어 축합 고리를 형성하고;하기 화학식 2로 표시되는 고리와 축합 고리를 형성하지 않는 R1 내지 R8은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;상기 R1 내지 R8의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며;[화학식 2]상기 화학식 2에서,점선은 축합이 이루어지는 부분을 의미하고;Y1 내지 Y12는 각각 독립적으로 N 또는 C(R9)이며;R9는 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R9가 복수 개인 경우 이들은 서로 동일하거나 상이하며;상기 R9의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.
- 제1항에 있어서,상기 R9는 하기 화학식 6으로 표시되는 치환기인 화합물:[화학식 6]상기 화학식 6에서,*은 결합이 이루어지는 부분을 의미하고;L1 및 L2는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;R10은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, R10의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.
- 제3항에 있어서,상기 L1 및 L2는 각각 독립적으로 하기 화학식 7 내지 11 중 어느 하나로 표시되는 링커인 화합물:[화학식 7][화학식 8][화학식 9][화학식 10][화학식 11]상기 화학식 7 내지 11에서,*은 결합이 이루어지는 부분을 의미하고;X1은 O, S, N(R12) 또는 C(R13)(R14)이며;X2는 N 또는 C(R15)이며;p는 0 내지 4의 정수이며;R11은 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R11이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R12 내지 R15는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고;상기 R11 내지 R15의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.
- 제3항에 있어서,상기 R10은 수소, 중수소(D), C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 화합물.
- 제3항에 있어서,상기 R10은 하기 화학식 12 내지 14 중 어느 하나로 표시되는 치환기인 화합물:[화학식 12][화학식 13][화학식 14]상기 화학식 12 내지 14에서,*은 결합이 이루어지는 부분을 의미하고;Z1 내지 Z5는 각각 독립적으로 N 또는 C(R18)이며;T1 및 T2는 각각 독립적으로 단일결합, C(R19)(R20), N(R21), O 및 S로 이루어진 군에서 선택되나, T1 및 T2 모두가 단일결합은 아니며;q 및 r은 각각 독립적으로 0 내지 4의 정수이며;R16 및 R17은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R16 및 R17 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R18 내지 R21은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R18 내지 R21 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;상기 R16 내지 R21의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.
- 제3항에 있어서,상기 R10은 하기 화학식 A-1 내지 A-24 중 어느 하나로 표시되는 치환기인 화합물:상기 화학식 A-1 내지 A-24에서,*은 결합이 이루어지는 부분을 의미하고;t는 0 내지 5의 정수이며,u는 0 내지 4의 정수이며;v는 0 내지 3의 정수이며;w는 0 내지 2의 정수이며;q 및 r은 각각 독립적으로 0 내지 4의 정수이며;R16, R17 및 R22는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R16, R17 및 R22 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R18 내지 R21은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;상기 R16 내지 R22의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.
- 제3항에 있어서,상기 R10은 하기 화학식 15로 표시되는 치환기인 화합물:[화학식 15]상기 화학식 15에서,*은 결합이 이루어지는 부분을 의미하고;R23 및 R24는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;상기 R23 및 R24의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.
- 제8항에 있어서,상기 R23 및 R24는 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 화합물.
- 제8항에 있어서,상기 R23 및 R24는 각각 독립적으로 수소, 페닐기, 비페닐기, 터페닐기, 나프탈레닐기, 플루오레닐기, 및 하기 화학식 16으로 표시되는 치환기로 이루어진 군에서 선택되는 화합물;[화학식 16]상기 화학식 16에서,*은 결합이 이루어지는 부분을 의미하고;L3은 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며;R25 및 R26은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;상기 L3의 아릴렌기 및 헤테로아릴렌기와, R25 및 R26의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.
- (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.
- 제12항에 있어서,상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 전자 수송층, 전자 수송 보조층, 전자 주입층, 수명 개선층, 발광층 및 발광 보조층으로 이루어진 군에서 선택되는 유기 전계 발광 소자.
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---|---|---|---|---|
KR102360108B1 (ko) * | 2017-05-23 | 2022-02-09 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102075732B1 (ko) * | 2017-09-12 | 2020-02-10 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
KR102109789B1 (ko) * | 2017-10-19 | 2020-05-12 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
KR102103503B1 (ko) * | 2017-10-30 | 2020-04-22 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
KR102092266B1 (ko) * | 2018-07-20 | 2020-03-23 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
WO2020106028A1 (ko) * | 2018-11-19 | 2020-05-28 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
CN109535168A (zh) * | 2018-12-05 | 2019-03-29 | 烟台九目化学制品有限公司 | 一种二噁英类有机化合物及其应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130078439A (ko) * | 2011-12-30 | 2013-07-10 | 제일모직주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
WO2014010910A1 (ko) * | 2012-07-13 | 2014-01-16 | 덕산하이메탈(주) | 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR20140042554A (ko) * | 2012-09-28 | 2014-04-07 | 제일모직주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
WO2015012618A1 (en) * | 2013-07-25 | 2015-01-29 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107814820B (zh) | 2011-07-29 | 2020-08-11 | 默克专利有限公司 | 用于电子器件的化合物 |
KR101614599B1 (ko) | 2014-04-09 | 2016-04-21 | 주식회사 두산 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102436175B1 (ko) | 2014-05-09 | 2022-08-26 | 에스에프씨주식회사 | 신규한 방향족 유기발광 화합물 및 이를 포함하는 유기 발광 소자 |
WO2015174682A1 (ko) | 2014-05-13 | 2015-11-19 | 에스에프씨 주식회사 | 방향족아민기를 포함하는 헤테로고리 화합물및 이를 포함하는 유기 발광 소자 |
-
2015
- 2015-12-24 KR KR1020150185976A patent/KR101829108B1/ko active IP Right Grant
-
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- 2016-12-23 US US15/781,862 patent/US11066382B2/en active Active
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20130078439A (ko) * | 2011-12-30 | 2013-07-10 | 제일모직주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
WO2014010910A1 (ko) * | 2012-07-13 | 2014-01-16 | 덕산하이메탈(주) | 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR20140042554A (ko) * | 2012-09-28 | 2014-04-07 | 제일모직주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
WO2015012618A1 (en) * | 2013-07-25 | 2015-01-29 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
Non-Patent Citations (1)
Title |
---|
DATABASE CAS 13 March 2013 (2013-03-13), retrieved from STN Database accession no. RN 1423138-63-9 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110494430A (zh) * | 2017-10-19 | 2019-11-22 | 株式会社Lg化学 | 新型化合物及利用其的有机发光元件 |
CN110494430B (zh) * | 2017-10-19 | 2022-05-27 | 株式会社Lg化学 | 新型化合物及利用其的有机发光元件 |
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CN108349931B (zh) | 2022-08-05 |
KR101829108B1 (ko) | 2018-02-13 |
CN108349931A (zh) | 2018-07-31 |
US20180346439A1 (en) | 2018-12-06 |
US11066382B2 (en) | 2021-07-20 |
KR20170076117A (ko) | 2017-07-04 |
JP6942707B2 (ja) | 2021-09-29 |
JP2019503364A (ja) | 2019-02-07 |
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