CN111556865B - Polycyclic compound and organic electronic device including the same - Google Patents
Polycyclic compound and organic electronic device including the same Download PDFInfo
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- CN111556865B CN111556865B CN201980007580.8A CN201980007580A CN111556865B CN 111556865 B CN111556865 B CN 111556865B CN 201980007580 A CN201980007580 A CN 201980007580A CN 111556865 B CN111556865 B CN 111556865B
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- -1 Polycyclic compound Chemical class 0.000 title claims description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 239000010410 layer Substances 0.000 claims description 225
- 125000004432 carbon atom Chemical group C* 0.000 claims description 157
- 125000001424 substituent group Chemical group 0.000 claims description 106
- 125000003118 aryl group Chemical group 0.000 claims description 100
- 239000000126 substance Substances 0.000 claims description 87
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 76
- 229910052805 deuterium Inorganic materials 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 238000002347 injection Methods 0.000 claims description 62
- 239000007924 injection Substances 0.000 claims description 62
- 125000005843 halogen group Chemical group 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 49
- 239000012044 organic layer Substances 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 230000005525 hole transport Effects 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 29
- 125000001624 naphthyl group Chemical group 0.000 claims description 26
- 239000002019 doping agent Substances 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 16
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- 125000006267 biphenyl group Chemical group 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 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 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 3
- 238000004020 luminiscence type Methods 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 238000000034 method Methods 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- 238000005259 measurement Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 230000002194 synthesizing effect Effects 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 125000003367 polycyclic group Chemical group 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 230000001629 suppression Effects 0.000 description 8
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 125000005241 heteroarylamino group Chemical group 0.000 description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 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 5
- 239000012153 distilled water Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000001769 aryl amino group Chemical group 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000004957 naphthylene group Chemical group 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 3
- 125000005264 aryl amine group Chemical group 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- VBQVHWHWZOUENI-UHFFFAOYSA-N 1-phenyl-2H-quinoline Chemical compound C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 VBQVHWHWZOUENI-UHFFFAOYSA-N 0.000 description 2
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 150000003975 aryl alkyl amines Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000006616 biphenylamine group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 238000005304 joining Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 2
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 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 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [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 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical compound N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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- 229910052688 Gadolinium Inorganic materials 0.000 description 1
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- 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
-
- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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Abstract
The present specification provides a compound of formula 1 and an organic electronic device including the same.
Description
Technical Field
The present specification claims priority from korean patent application No. 10-2018-0039760, filed on the korean patent office on 5 th month 4 of 2018, the entire contents of which are included in the present specification.
The present specification relates to compounds and organic electronic devices comprising the same.
Background
As a representative example of the organic electronic device, there is an organic light emitting device. In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
Most of the materials used in the organic light emitting device are pure organic materials or complex compounds of organic materials and metal constituting complexes. The materials used in the organic light-emitting device may be classified into a hole-injecting material, a hole-transporting material, a light-emitting material, an electron-transporting material, an electron-injecting material, and the like according to the purpose. Here, as the hole injecting substance or the hole transporting substance, an organic substance having a p-type property, that is, an organic substance which is easily oxidized and has an electrochemically stable state when oxidized is mainly used. On the other hand, as the electron injecting substance or the electron transporting substance, an organic substance having n-type property, that is, an organic substance which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. As the light-emitting layer substance, a substance having both p-type property and n-type property, that is, a substance having a stable form in both an oxidation state and a reduction state is preferable, and a substance having high light emission efficiency for converting it into light when an excitation is formed is preferable.
In order to fully develop the excellent characteristics of the organic light-emitting device, development of a substance constituting an organic layer in the device is continuously required.
Disclosure of Invention
Technical problem
The present specification describes compounds and organic electronic devices comprising the same.
Solution to the problem
An embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, silyl, boron, hydroxyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkylamino, substituted or unsubstituted arylamino, substituted or unsubstituted heteroarylamino, substituted or unsubstituted arylalkylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkylheteroarylamino, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl,
ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,
n1 is an integer of 0 to 3, and when n1 is 2 or more, 2 or more R1 s are the same or different from each other,
n2 is an integer of 0 to 5, and when n2 is 2 or more, 2 or more R2 are the same or different from each other.
In addition, the present invention provides an organic electronic device, wherein the organic electronic device includes: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound.
Effects of the invention
The compounds described in the present specification can be used as materials for organic layers of organic electronic devices. In the case of manufacturing an organic electronic device including the compound according to at least one embodiment, an organic electronic device having high efficiency and long lifetime can be obtained.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
FIG. 3 illustrates MS measurement patterns of the compound BD-2.
FIG. 4 illustrates MS measurement patterns of the compound BD-3.
FIG. 5 illustrates the MS measurement profile of compound BD-6.
1: substrate board
2: anode
3: light-emitting layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: light-emitting layer
8: electron transport layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound represented by the following chemical formula 1. In the case where the compound represented by the following chemical formula 1 is used for the organic layer of the organic electronic device, the structure of the luminophore is simple and rigid, and thus the half width is relatively improved, so that high efficiency can be achieved. Further, since the organic electronic device is chemically more stable by containing dibenzofuran, in the case of manufacturing the organic electronic device containing the compound represented by chemical formula 1 of the present invention, the life characteristics of the organic electronic device are improved.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, silyl, boron, hydroxyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkenyl, substituted or unsubstituted alkylamino, substituted or unsubstituted arylamino, substituted or unsubstituted heteroarylamino, substituted or unsubstituted arylalkylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkylheteroarylamino, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl,
Ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,
n1 is an integer of 0 to 3, and when n1 is 2 or more, 2 or more R1 s are the same or different from each other,
n2 is an integer of 0 to 5, and when n2 is 2 or more, 2 or more R2 are the same or different from each other.
In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, cyano (-CN), nitro, silyl, boron group, hydroxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkylamino group, substituted or unsubstituted arylamino group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylalkylamino group, substituted or unsubstituted arylheteroarylamino group, substituted or unsubstituted alkylheteroarylamino group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heterocyclic group, or a substituent linked with 2 or more substituents among the above-exemplified substituents, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
Examples of the above substituents are described below, but are not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the silyl group may be represented by-SiY 1 Y 2 Y 3 The chemical formula of (A) is shown in the specification, Y is shown in the specification 1 、Y 2 And Y 3 Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, and vinyldimethylsilyl groupThe silane group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like, but are not limited thereto.
In the present specification, the boron group may be represented BY-BY 4 Y 5 The chemical formula of (A) is shown in the specification, Y is shown in the specification 4 And Y 5 Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, and the like.
In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy and the like are possible, but not limited thereto.
The alkyl groups, alkoxy groups, and other substituents containing an alkyl moiety described herein are all included in either straight or branched chain forms.
In this specification, the aryl group in the aryloxy group may be as described below with respect to the aryl group.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl and the like, but are not limited thereto.
In the present specification, the number of carbon atoms of the alkylamino group is not particularly limited, but may be 1 to 40, and according to an embodiment, may be 1 to 20. Specific examples of the alkylamino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, and the like.
In the specification, as examples of the arylamine group, there are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamino group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The above arylamine group containing 2 or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group.
Specific examples of the arylamino group include, but are not limited to, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a diphenylamino group, a phenylnaphthylamino group, a biphenylphenylamino group, a biphenylamino group, and a fluorenylphenylamino group.
In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted mono-heteroarylamino group, a substituted or unsubstituted di-heteroarylamino group, or a substituted or unsubstituted tri-heteroarylamino group. The heteroaryl group in the heteroarylamino group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The above-mentioned heteroarylamine group containing 2 or more heteroaryl groups may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or may contain both a monocyclic heteroaryl group and a polycyclic heteroaryl group.
In the present specification, arylalkylamine groups refer to amine groups substituted with aryl groups and alkyl groups.
In this specification, arylheteroarylamine refers to an amine group substituted with aryl and heteroaryl.
In the present specification, arylalkylamine groups refer to amine groups substituted with aryl groups and alkyl groups.
In this specification, alkylheteroaryl amine groups refer to amine groups substituted with alkyl and heteroaryl groups.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as phenyl, biphenyl, terphenyl, or tetrabiphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl, Examples of the group include, but are not limited to, a fluorenyl group, a benzofluorenyl group, and a triphenylene group.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.
In the case where the above fluorenyl group is substituted, it may beAn isospirofluorenyl group;(9, 9-dimethylfluorenyl) and +.>(9, 9-diphenylfluorenyl) and the like. However, the present invention is not limited thereto.
In the present specification, the heterocyclic group is a ring group containing 1 or more heteroatoms in N, O, P, S, si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, and benzonaphthothienyl.
In the present specification, the hydrocarbon ring group may be an aromatic group, an aliphatic group, or a condensed ring of an aromatic group and an aliphatic group, the description of the aryl group may be applied to the aromatic hydrocarbon ring except for the 1-valent group, and the description of the cycloalkyl group may be applied to the aliphatic hydrocarbon ring except for the 1-valent group. Further, as an example of the condensed rings of the above aromatic and aliphatic, hydrogenated naphthalene, specifically, 1,2,3, 4-tetrahydronaphthalene may be mentioned
In this specification, the heteroaryl group is not aromatic, and the above description about the heterocyclic group can be applied.
According to an embodiment of the present invention, the maximum luminescence peak of the compound of the present invention may be in the range of 430nm to 470nm, and blue light may be emitted in the case that the compound is contained in the light emitting layer of the organic electronic device.
According to an embodiment of the present invention, R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, silyl, boron, hydroxyl, substituted or unsubstituted alkyl having 1 to 60 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 60 carbon atoms, substituted or unsubstituted alkenyl having 2 to 40 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms, or substituted or unsubstituted heterocyclyl having 2 to 60 carbon atoms.
According to another embodiment, the above R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, silyl, boron, hydroxyl, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
In another embodiment, R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, silyl, substituted or unsubstituted alkyl of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, or substituted or unsubstituted aryl of 6 to 30 carbon atoms.
According to another embodiment, R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, silyl, alkyl of 1 to 20 carbon atoms, cycloalkyl of 3 to 30 carbon atoms, or aryl of 6 to 30 carbon atoms.
In another embodiment, R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, trimethylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted cyclohexyl, or substituted or unsubstituted phenyl.
According to another embodiment, R1 and R2 above are the same or different from each other and are each independently hydrogen, deuterium, trimethylsilyl, methyl, cyclohexyl, or phenyl.
According to an embodiment of the present invention, n1 is an integer of 0 to 2.
According to another embodiment, n1 is 0 or 1.
According to an embodiment of the present invention, n2 is an integer of 0 to 2.
According to another embodiment, n2 is 0 or 1.
According to an embodiment of the present invention, ar1 to Ar4 mentioned above are the same as or different from each other, and each is independently hydrogen, deuterium, silyl, boron group, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted hydrocarbon ring group having 3 to 60 carbon atoms, or substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
In another embodiment, ar1 to Ar4 are the same as or different from each other, and each is independently hydrogen, deuterium, silyl, boron, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 3 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to another embodiment, ar1 to Ar4 mentioned above are the same as or different from each other, and each is independently a substituted or unsubstituted hydrocarbon ring group of 3 to 60 or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
In another embodiment, ar1 to Ar4 are the same as or different from each other, and each is independently a substituted or unsubstituted hydrocarbon ring group having 3 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to another embodiment, the above Ar1 to Ar4 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted hydronaphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.
In another embodiment, ar1 to Ar4 are the same or different from each other, and each is independently a substituted or unsubstituted phenyl group which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted biphenyl group which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted terphenyl group which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, halogen group, silyl group, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group and substituted or unsubstituted heterocyclic group; a substituted or unsubstituted naphthyl group which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted fluorenyl group which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted benzofluorenyl group which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted phenanthryl group which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted hydrogenated naphthyl group which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted dibenzofuranyl group which is bonded to 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted carbazolyl group in which 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group are bonded.
In another embodiment, ar1 to Ar4 are the same or different from each other, and each is independently a substituted or unsubstituted phenyl group which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a substituted or unsubstituted biphenyl group which is substituted with a substituent of 1 or more or a substituent of 2 or more selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; substituted or unsubstituted terphenyl groups bonded with 1 or more substituents or 2 or more substituents selected from deuterium, halogen groups, silyl groups, cyano groups, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic groups having 2 to 30 carbon atoms; a substituted or unsubstituted naphthyl group which is substituted with a substituent group formed by joining 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a substituted or unsubstituted fluorenyl group which is substituted with a substituent of 1 or more or a substituent of 2 or more selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a substituted or unsubstituted benzofluorenyl group which is bonded by a substituent of 1 or more or a substituent of 2 or more selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a substituted or unsubstituted phenanthryl group which is substituted with a substituent group formed by connecting 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a substituted or unsubstituted hydrogenated naphthyl group which is bonded to 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; substituted or unsubstituted dibenzofuranyl groups bonded with 1 or more substituents or 2 or more substituents selected from deuterium, halogen groups, silyl groups, cyano groups, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic groups having 2 to 30 carbon atoms; or a substituted or unsubstituted carbazolyl group which is formed by connecting 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
In another embodiment, ar1 to Ar4 are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with a substituent formed by joining 1 or more substituents selected from deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group, and a carbazolyl group, or 2 or more substituents; biphenyl groups substituted or unsubstituted with 1 or more substituents or 2 or more substituents selected from deuterium, halogen groups, cyano groups, trimethylsilyl groups, trifluoromethyl groups, methyl groups, ethyl groups, t-butyl groups, phenyl groups, t-butylphenyl groups and carbazolyl groups; a substituted or unsubstituted terphenyl group which is substituted with 1 or more substituents or 2 or more substituents selected from deuterium, halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, t-butyl group, phenyl group, t-butylphenyl group and carbazolyl group; a naphthyl group which is substituted or unsubstituted with a substituent group in which 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, t-butyl group, phenyl group, t-butylphenyl group and carbazolyl group are bonded; a fluorenyl group which is substituted or unsubstituted with a substituent group in which 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, t-butyl group, phenyl group, t-butylphenyl group and carbazolyl group are bonded; a benzofluorenyl group which is substituted or unsubstituted with a substituent group in which 1 or more substituents or 2 or more substituents selected from deuterium, halogen groups, cyano groups, trimethylsilyl groups, trifluoromethyl groups, methyl groups, ethyl groups, t-butyl groups, phenyl groups, t-butylphenyl groups and carbazolyl groups are bonded; a phenanthryl group which is substituted or unsubstituted with a substituent group in which 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, t-butyl group, phenyl group, t-butylphenyl group and carbazolyl group are bonded; hydrogenated naphthyl substituted or unsubstituted by a substituent which is bonded with 1 or more substituents or 2 or more substituents selected from deuterium, halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, t-butyl group, phenyl group, t-butylphenyl group and carbazolyl group; a dibenzofuranyl group which is substituted or unsubstituted with a substituent group in which 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, t-butyl group, phenyl group, t-butylphenyl group and carbazolyl group are bonded; or a carbazolyl group which is substituted or unsubstituted with a substituent group in which 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, cyano group, trimethylsilyl group, trifluoromethyl group, methyl group, ethyl group, t-butyl group, phenyl group, t-butylphenyl group and carbazolyl group are bonded.
According to an embodiment of the present invention, the above chemical formula 1 may be represented by any one of the following compounds.
The compound of the above chemical formula 1 may manufacture a core structure through a process shown in the following reaction formula. The substituents may be bonded by a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art.
< reaction >
The above reaction formula is merely an example of a method for producing a core structure of the compound according to an embodiment of the present invention and connecting substituents, and is not limited thereto.
The conjugation length of the compound has a close relationship with the energy band gap. Specifically, the longer the conjugate length of the compound, the smaller the energy band gap.
In the present invention, as described above, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure. In addition, in the present invention, by introducing various substituents into the core structure of the structure shown above, HOMO and LUMO energy levels of the compound can also be adjusted.
In addition, by introducing various substituents into the core structure of the structure described above, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, a substance satisfying the conditions required in each organic layer can be synthesized by introducing substituents mainly used in a hole injection layer substance, a hole transport substance, an electron suppression substance, a light-emitting layer substance, and an electron transport layer substance, which are used in manufacturing an organic light-emitting device, into the above-described core structure.
In addition, the organic electronic device according to the present invention is characterized by comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the above-mentioned compound.
The organic electronic device of the present invention can be manufactured by a general method and material for manufacturing an organic electronic device, except that one or more organic layers are formed using the above-described compound.
According to an embodiment of the present invention, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an Organic Photoconductor (OPC), and a glass transistor.
The organic light emitting device is exemplified below.
The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that performs electron injection and electron transport simultaneously, and the like as the organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller or larger number of organic layers.
In the organic light emitting device of the present invention, the above-mentioned organic layer may include an electron transport layer or an electron injection layer, and the above-mentioned electron transport layer or electron injection layer may contain the above-mentioned compound.
In the organic light emitting device of the present invention, the above organic layer may include a hole injection layer or a hole transport layer, and the above hole injection layer or hole transport layer may contain the above-mentioned compound.
In this case, the hole injection layer or the hole transport layer may be composed of only the above-mentioned compound, and the above-mentioned compound may be present in a state of being mixed or doped in the material of other hole injection layer or hole transport layer known in the art.
In the organic light-emitting device of the present invention, the above-mentioned organic layer includes a light-emitting layer containing the above-mentioned compound.
According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the above-mentioned compound as a dopant of the light emitting layer.
In another embodiment, the organic layer includes a light-emitting layer including the compound as a dopant of the light-emitting layer, and may further include a host.
According to another embodiment, the organic layer includes a light emitting layer including the compound as a dopant of the light emitting layer, and may further include the following chemical formula 1-a as a host.
[ chemical formula 1-A ]
In the above-mentioned chemical formula 1-a,
a1 to A3 are the same or different from each other and each independently is hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
l1 to L3 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
r11 is hydrogen, deuterium, a halogen group, cyano (-CN), nitro, silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q1 is an integer of 0 to 7, and when q1 is 2 or more, 2 or more R11 are the same or different from each other.
According to an embodiment of the present invention, the above A1 to A3 are the same or different from each other, and each is independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to another embodiment, A1 to A3 are the same as or different from each other, and each is independently hydrogen, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
In another embodiment, A1 to A3 are the same or different from each other, and each is independently hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
According to another embodiment, A3 is hydrogen.
In another embodiment, A1 is hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thienyl, or substituted or unsubstituted indolocarbazolyl.
According to another embodiment, A1 is hydrogen; phenyl substituted or unsubstituted with deuterium, alkyl of 1 to 10 carbon atoms, or aryl of 6 to 30 carbon atoms; naphthyl substituted or unsubstituted with deuterium, alkyl of 1 to 10 carbon atoms, or aryl of 6 to 30 carbon atoms; dibenzofuranyl substituted or unsubstituted with deuterium, alkyl of 1 to 10 carbon atoms, or aryl of 6 to 30 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; thienyl substituted or unsubstituted with deuterium, alkyl of 1 to 10 carbon atoms, or aryl of 6 to 30 carbon atoms; or an indolocarbazolyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
In another embodiment, A1 is hydrogen, phenyl substituted or unsubstituted with deuterium, naphthyl substituted or unsubstituted with methyl, dibenzofuranyl, naphthobenzofuranyl, thienyl substituted with phenyl, or indolocarbazolyl.
According to an embodiment of the present invention, A2 is hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, A2 is hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.
In another embodiment, A2 is hydrogen; phenyl substituted or unsubstituted with deuterium (D), a halogen group, cyano, silyl, alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 30 carbon atoms, or aryl of 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a naphthyl group substituted or unsubstituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
According to another embodiment, A2 is hydrogen; phenyl substituted or unsubstituted with cyclohexyl, phenyl or naphthyl; biphenyl substituted or unsubstituted with deuterium, fluorine, cyano, or trimethylsilyl; or naphthyl substituted or unsubstituted with methyl, phenyl, or naphthyl.
According to an embodiment of the present invention, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
In another embodiment, the above-mentioned L1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
According to another embodiment, the above-mentioned L1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
According to another embodiment, the above-mentioned L1 to L3 are the same or different from each other, and are each independently a directly bonded, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In another embodiment, the above L1 to L3 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
According to another embodiment, the above-mentioned L1 to L3 are identical to or different from each other and are each independently a direct bond, phenylene, or naphthylene.
According to an embodiment of the present invention, R11 is hydrogen, deuterium, a halogen group, cyano (-CN), nitro, silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted phosphine oxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
According to another embodiment, R11 is hydrogen, deuterium, a halogen group, cyano (-CN), nitro, silyl, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
In another embodiment, R11 is hydrogen.
According to an embodiment of the present invention, q1 is an integer of 0 to 2.
In another embodiment, q1 is 0 or 1.
In one embodiment of the present specification, the above chemical formula 1-a may be represented by any one of the following compounds.
In the case of containing the compound of the present invention as a dopant of the light emitting layer and containing the above chemical formula 1-a as a host, the content of the dopant may be 1 to 10 parts by weight based on 100 parts by weight of the host.
According to another embodiment, the organic layer includes a light-emitting layer including the compound as described above as a dopant of the light-emitting layer, and may further include 2 or more kinds of compounds represented by the following chemical formulas 1-B and 1-C as main bodies.
[ chemical formula 1-B ]
[ chemical formula 1-C ]
In the above chemical formulas 1-B and 1-C,
a4 to A8 are the same or different from each other and are each independently hydrogen, or a substituted or unsubstituted aryl group,
a9 is a substituted or unsubstituted heterocyclic group,
l4 to L9 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
r12 and R13 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano (-CN), nitro, silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q2 and q3 are each integers from 0 to 7, and when q2 and q3 are each 2 or more, substituents in brackets are the same or different from each other.
According to an embodiment of the present invention, A4 to A8 are the same as or different from each other, and each is independently hydrogen or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
According to another embodiment, A4 to A8 mentioned above are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, A6 and A8 are hydrogen.
In another embodiment, A5 and A7 are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
In another embodiment, A5 and A7 are the same or different from each other, each independently hydrogen; phenyl substituted or unsubstituted with deuterium (D), a halogen group, cyano, silyl, alkyl of 1 to 10 carbon atoms, cycloalkyl of 3 to 30 carbon atoms, or aryl of 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a naphthyl group substituted or unsubstituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
According to another embodiment, A5 and A7 above, equal to or different from each other, are each independently hydrogen; phenyl substituted or unsubstituted with cyclohexyl, phenyl or naphthyl; biphenyl substituted or unsubstituted with deuterium, fluorine, cyano, or trimethylsilyl; or naphthyl substituted or unsubstituted with methyl, phenyl, or naphthyl.
According to an embodiment of the present invention, A4 is hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.
According to another embodiment, A4 is hydrogen; phenyl substituted or unsubstituted with deuterium, alkyl of 1 to 10 carbon atoms, or aryl of 6 to 30 carbon atoms; or a naphthyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
In another embodiment, A4 is hydrogen, phenyl substituted or unsubstituted with deuterium, or naphthyl substituted or unsubstituted with methyl.
According to one embodiment of the present specification, A9 is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
According to another embodiment, A9 is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
In another embodiment, A9 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted thienyl group, or a substituted or unsubstituted indolocarbazolyl group.
According to another embodiment, A9 is a dibenzofuranyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; thienyl substituted or unsubstituted with deuterium, alkyl of 1 to 10 carbon atoms, or aryl of 6 to 30 carbon atoms; or an indolocarbazolyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
In another embodiment, A9 is dibenzofuranyl, naphthobenzofuranyl, thienyl substituted with phenyl, or indolocarbazolyl.
According to an embodiment of the present invention, the above-mentioned L4 to L9 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
In another embodiment, the above-mentioned L4 to L9 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
According to another embodiment, the above-mentioned L4 to L9 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
According to another embodiment, the above-mentioned L4 to L9 are the same or different from each other, and are each independently a directly bonded, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In another embodiment, the above-mentioned L4 to L9 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
According to another embodiment, the above-mentioned L4 to L9 are identical to or different from each other and are each independently a direct bond, phenylene, or naphthylene.
According to an embodiment of the present invention, R12 and R13 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, cyano (-CN), nitro, silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
According to another embodiment, the above R12 and R13 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano (-CN), nitro, silyl, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
In another embodiment, R12 and R13 are hydrogen.
According to an embodiment of the present specification, q2 is an integer of 0 to 7, and when q2 is 2 or more, 2 or more R12 are the same or different from each other.
According to another embodiment, q2 is an integer from 0 to 2.
According to another embodiment, q2 is 0 or 1.
According to an embodiment of the present specification, q3 is an integer of 0 to 7, and when q3 is 2 or more, 2 or more R13 are the same or different from each other.
According to another embodiment, q3 is an integer from 0 to 2.
According to another embodiment, q3 is 0 or 1.
In one embodiment of the present specification, the above chemical formula 1-B may be represented by any one of the following compounds.
In one embodiment of the present specification, the above chemical formulas 1 to C may be represented by any one of the following compounds.
In the case where the compound of the present invention is contained as a dopant of the light emitting layer and 2 or more of the compounds represented by the above chemical formulas 1-B and 1-C are contained as a host, the content of the dopant may be 1 to 10 parts by weight based on 100 parts by weight of the host.
According to another embodiment, the above compound may be included as a dopant of the light emitting layer, and the compound represented by the above chemical formula 1-B and the compound represented by the above chemical formula 1-C may be included as a host of the light emitting layer, and the mixed weight ratio (1-B: 1-C) of the above host may be 95:5 to 5:95.
In another embodiment, the organic layer includes a light-emitting layer including the compound as a dopant of the light-emitting layer, including a fluorescent host or a phosphorescent host, and may include other organic compounds, metals, or metal compounds as dopants.
As another example, the organic layer includes a light emitting layer containing the above compound as a dopant of the light emitting layer, containing a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant.
According to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include the compound as a host of the light-emitting layer.
As another example, the organic layer includes a light-emitting layer including the compound as a host of the light-emitting layer, and may further include a dopant.
In the organic light-emitting device of the present invention, the organic layer may include an electron-inhibiting layer, and the electron-inhibiting layer may include the compound.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.
For example, the above-described organic light emitting device may have a stacked structure as shown below, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(15) Anode/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/cathode
(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppressing layer/electron transport layer/electron injection layer/cathode
The structure of the organic light emitting device of the present invention may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described light-emitting layer 3.
Fig. 2 illustrates a structure of an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described hole injection layer 5, hole transport layer 6, light-emitting layer 7, or electron transport layer 8.
For example, the organic light emitting device according to the present invention may be manufactured by: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical vapor deposition) method such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), and then an organic layer including a hole injection layer, a hole transport layer, a layer which performs hole injection and hole transport simultaneously, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, and a layer which performs electron injection and electron transport simultaneously is formed on the anode, followed by vapor deposition of a substance which can be used as a cathode on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer that performs electron injection and electron transport simultaneously, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that performs electron injection and electron transport simultaneously, or the like, but the organic layer is not limited to this and may have a single-layer structure. The organic layer may be formed in a smaller number or larger number by using various polymer materials and using a solvent process (solvent process) other than vapor deposition, for example, spin coating, dip coating, doctor blading, screen printing, ink jet printing, or thermal transfer printing.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc Oxide, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2)-dioxy) thiophenes]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that functions to smoothly inject holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well inject holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer. The thickness of the hole injection layer may be 1 to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the movement of holes can be prevented.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring them to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples thereof include arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated portions, but the hole transport layer may be formed in 1 or more layers in an organic light-emitting device.
A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
An electron-suppressing layer may be provided between the hole-transporting layer and the light-emitting layer. The electron-inhibiting layer may be formed using the above-described compound or a material known in the art.
The light-emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The host material of the light-emitting layer includes an aromatic condensed ring derivative, a heterocyclic compound, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, etc., but are not limited thereto.
When the light-emitting layer emits red light, as the light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonide), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) acetylacetonate), PQIr (tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin) or a fluorescent substance such as Alq3 (tris (8-hydroxyquinoline) aluminum) may be used, but not limited thereto. When the light-emitting layer emits green light, a phosphorescent substance such as Ir (ppy) 3 (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or a fluorescent substance such as Alq3 (tris (8-hydroxyquinoline) aluminum, may be used as the light-emitting dopant, but is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4, 6-F2 ppy) 2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymer, PPV-based polymer may be used as the light-emitting dopant, but is not limited thereto.
A hole-suppressing layer may be provided between the electron-transporting layer and the light-emitting layer, and materials known in the art may be used.
The electron transport layer can perform the function of smooth electron transport. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the reduction of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage in order to improve the movement of electrons can be prevented when the thickness of the electron transport layer is too thick.
The electron injection layer can perform a function of smoothly injecting electrons. The electron injecting substance is preferably the following compound: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like, Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the hole injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the invention
In the following, examples are given to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present application should not be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present description to those skilled in the art.
Synthesis example
Synthesis example 1.
Under nitrogen, the mixture was charged with starting material A-1 (80 g) and starting material A-2 (87.5 g), bis (tri-tert-butylphosphine) palladium (0) [ Bis (tri-tert-butylphosphine) -paladium (0)](0.38g)、K 2 CO 3 A flask of the solution (152.6 g dissolved in 300mL of water (152.6g in 300mL of water)) and Tetrahydrofuran (THF) 900mL was stirred at 50℃for 5 hours. After the reaction solution was cooled to room temperature, water and ethyl acetate (ethyl acetate) were added thereto, followed by extraction and washing. The organic layer was recovered and the extraction solvent was removed to give intermediate A-3.
Under nitrogen atmosphere, the mixture was charged with A-3 and K without further purification 2 CO 3 (44g) And NMP (N-methyl-2-pyrrolidone) 1L flask was heated and stirred at 150℃for 5 hours. At the end of the reaction, the reaction mixture was cooled to room temperature, 700mL of water was further added, and the mixture was stirred for 30 minutes. The resulting solid was filtered to give a solid, which was purified using ethyl acetate and saturated NH 4 After separating the Cl solution, the organic layer was recovered and dried over MgSO 4 (anhydrous) for treatment and filtration. The solvent of the filtered solution was distilled off under reduced pressure, and after recrystallization (hexane), it was dried, whereby 58.4g of intermediate A-4 was obtained.
Synthesis example 2.
After 30g of intermediate A-4 was dissolved in 300mL of acetonitrile (acetonitrile), a potassium carbonate solution (46 g of potassium carbonate was dissolved in 100mL of H) was further added at room temperature 2 O), 67.5g of nonafluorobutanesulfonyl fluoride [ Nonafluorobutanesulfonyl fluoride ] were then added dropwise]. After stirring for 2 hours, 200mL of water was added and stirred for 30 minutes. The resulting solid was filtered to give a solid, which was purified using ethyl acetate and saturated NH 4 After separating the Cl solution, the organic layer was recovered with Na 2 SO 4 (anhydrous) treatment and filtration. Distilling off the solvent of the filtered solution under reduced pressure, and weighingCrystallization (ethyl acetate/hexane) followed by drying gave 41g of intermediate A-5.
Synthesis example 3.
4g of intermediate A-5, 4.8g of bis (4- (tert-butyl) phenyl) amine are reacted under nitrogen]7g of potassium phosphate [ potassium phosphate ]]0.12g of bis (dibenzylideneacetone) palladium (0) [ Bis (dibenzylideneacetone) paladium (0) Pd (dba) 2 ]0.19g of 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (Xphos) was dissolved in 100mL of di-waterAfter the alkane, the mixture was heated and stirred at 100℃for 36 hours. After the reaction, the reaction solution was cooled to room temperature, and water and NH were added 4 Cl solution, after separation, was treated with MgSO 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by column chromatography (EA/hx=30/1), whereby 3.1g of compound BD-1 was obtained.
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]Peaks were confirmed at=777.
Synthesis example 4.
3.0g of compound BD-2 was synthesized by the same method as that of Synthesis example 3.
The MS measurement spectrum of the above compound BD-2 is shown in FIG. 3, at [ M+H ] + ]The peak was confirmed at=897.
Synthesis example 5.
4.0g of compound BD-3 was synthesized by the same method as that of Synthesis example 3.
The MS measurement spectrum of the above compound BD-3 is shown in FIG. 4, at [ M+H ] + ]The peak was confirmed at=937.
Synthesis example 6.
2.9g of compound BD-4 was synthesized by the same method as that for synthesizing compound BD-1 of Synthesis example 3.
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]Peak was confirmed at=913.
Synthesis example 7.
2.7g of compound BD-5 was synthesized by the same method as that for synthesizing the compound BD-1 of Synthesis example 3.
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]Peak was confirmed at=913.
Synthesis example 8.
3.8g of compound BD-6 was synthesized by the same method as that of Synthesis example 3.
The MS measurement spectrum of the above compound BD-6 is shown in FIG. 5, at [ M+H ] + ]Peaks were confirmed at=997.
Synthesis example 9.
2.9g of compound BD-7 was synthesized by the same method as that for synthesizing compound BD-1 of Synthesis example 3.
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]Peaks were confirmed at=997.
Synthesis example 10.
2.2g of compound BD-8 was synthesized by the same method as that for synthesizing compound BD-1 of Synthesis example 3.
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]Peaks are identified at =905.
Synthesis example 11.
2.7g of compound BD-9 was synthesized by the same method as that for synthesizing compound BD-1 of Synthesis example 3.
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]The peak was confirmed at=767.
Synthesis example 12.
4.2g of compound BD-10 was synthesized by the same method as that for synthesizing the compound BD-1 of Synthesis example 3.
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]The peak was confirmed at =1141.
Synthesis example 13.
A flask containing 28g of intermediate A-4, 5g of NaH, 400mL of Dimethylformamide (DMF) was stirred at 0deg.C for 30 minutes under nitrogen. Then, 21g of 4-methoxybenzyl chloride (4-methoxybenzyl chloride) was further added, followed by stirring at room temperature for 8 hours. After the reaction was completed, 400mL of water was added thereto and stirred for 30 minutes. The resulting solid was filtered to give a solid, which was purified using ethyl acetate and saturated NH 4 After separating the Cl solution, the organic layer was recovered with Mg 2 SO 4 (anhydrous) treatment and filtration. The solvent of the filtered solution was distilled off under reduced pressure, and after recrystallization (ethyl acetate/hexane), drying was performed, whereby 31g of intermediate B-1 was obtained.
31g of intermediate B-1 was dissolved in 300mL of tetrahydrofuran (anhydrous) cooled to 0deg.C under nitrogen, placed in a flask, and 41.5mL of n-Butyllithium [ n-butyl thium,2.5M hexane solution (2.5M in hexane) was slowly added dropwise]After that, stirring was carried out for 1 hour. 13g of bromine was slowly added dropwise at 0℃and the temperature was then raised to room temperature and stirred for 3 hours. After the reaction is finished, saturated NaS is added 2 O 3 And NaCl solution, separating, and using MgSO 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure, and purified by recrystallization (ethyl acetate/hexane), whereby 23g of intermediate B-2 was obtained.
Synthesis example 14.
Intermediate B-3 was synthesized by the same method as the method of synthesizing intermediate a-3 of synthesis example 1, and the next reaction was carried out without further purification.
Was charged with 9.5g of DDQ (2, 3-dichloro-5,6-dicyano-p-benzoquinone,2, 3-dichloro-5, 6-dicyano-p-benzoquinone), 130mL of CHCl without further purification of intermediate B-3 3 The flask was stirred at room temperature for 2 hours. At the end of the reaction, the reaction solution was filtered through celite (celite), and the filtrate was added with NaCl solution, followed by separation with MgSO 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure to give intermediate B-4 without further purification.
Intermediate B-5 was synthesized by the same method as that of intermediate A-5 of Synthesis example 2, and 11g of intermediate B-5 was obtained by silica gel column chromatography (eluent: ethyl acetate/hexane).
Synthesis example 15.
2.5g of compound BD-11 was synthesized using intermediate B-5 in the same manner as in the synthesis of compound BD-1 of Synthesis example 3.
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]Peaks were confirmed at=917.
Synthesis example 16.
2.2g of compound BD-12 was synthesized using intermediate B-5 in the same manner as in the synthesis of compound BD-1 of Synthesis example 3.
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]The peak was confirmed at=865.
Synthesis example 17.
Under nitrogen, 10g of intermediate B-2 was dissolved in 80mL of tetrahydrofuran (anhydrous) cooled to-78deg.C, placed in a flask, and 8.6mL of n-Butyllithium [ n-Butylllithium, 2.5M in hexane (2.5M in hexane) was slowly added dropwise]After that, stirring was carried out for 30 minutes. 3.5mL of chlorotrimethylsilane (chlorotrimethylsilane) was slowly added dropwise at-78℃and then stirred at the same temperature for a further 30 minutes, after which the temperature was slowly raised to room temperature and stirred for 6 hours. After the reaction is finished, saturated NH is added 4 Cl solution, after separation, was treated with Na 2 SO 4 (anhydrous) treatment and filtration. Intermediate C-1 was obtained without further purification and was subjected to the next reaction.
By the same method as that for synthesizing intermediate B-5 from intermediate B-3 in Synthesis example 14, 7.4g of intermediate C-3 was obtained using intermediate C-1.
Synthesis example 18.
By the same method as that for synthesizing the compound BD-1 of Synthesis example 3, compound BD-13 was synthesized using intermediate C-3, and 1.76g of Compound BD-13 was synthesized using column chromatography (eluent: toluene/hexane).
The mass spectrum measurement result of the obtained solid is shown in [ M+H ] + ]The peak was confirmed at=837.
< example >
Example 1.
ITO (indium tin oxide) toThe glass substrate (corning 7059 glass) coated with the film was put into distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was distilled water filtered twice using a Filter (Filter) manufactured by millbore co., ltd. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the ITO transparent electrode thus prepared, the following compound HAT was usedAnd performing thermal vacuum evaporation to form a hole injection layer. Vacuum deposition as a hole transport layer on the hole injection layer>The following compound HT-A, followed by evaporation of +.>The following compound HT-B. BH-1 as a host and BD-2 as a dopant were added at 2 wt% on the light emitting layer, (-) -on the light emitting layer>Vacuum evaporation was performed on the thickness of (c).
Then, vapor deposition is carried out in a ratio of 1:1Compound ET-a and compound Liq of (a) on which +. >Magnesium (Mg) doped with 10 wt% silver (Ag) in thickness>Aluminum of a thickness is sequentially vapor-deposited to form a cathode, thereby manufacturing an organic light-emitting device.
In the above process, the vapor deposition rate of the organic matter is maintainedLiF maintenance->Is kept at>To->Is a vapor deposition rate of (a). />
Example 2.
An organic light-emitting device was manufactured in the same manner as in example 1, except that the compound BD-3 was used instead of the compound BD-2 in example 1 described above.
Example 3.
An organic light-emitting device was manufactured in the same manner as in example 1, except that the compound BD-6 was used instead of the compound BD-2 in example 1 described above.
Example 4.
An organic light-emitting device was manufactured in the same manner as in example 1, except that the compound BD-8 was used instead of the compound BD-2 in example 1 described above.
Example 5.
An organic light-emitting device was manufactured in the same manner as in example 1, except that the compound BD-11 was used instead of the compound BD-2 in example 1 described above.
Example 6.
An organic light-emitting device was manufactured in the same manner as in example 1, except that the compound BD-13 was used instead of the compound BD-2 in example 1 described above.
Example 7.
An organic light-emitting device was manufactured in the same manner as in example 1, except that in example 1, the compound BH-2 (weight ratio of BH-1 to BH-2: 1:1) was further included.
Comparative example
Comparative example 1.
An organic light-emitting device was manufactured in the same manner as in example 1, except that the compound D-1 was used instead of the compound BD-2 in example 1.
Comparative example 2.
An organic light emitting device was manufactured in the same manner as in example 1, except that the compound D-2 was used instead of the compound BD-2 in example 1 described above.
Comparative example 3.
An organic light-emitting device was manufactured in the same manner as in example 1, except that the compound D-3 was used instead of the compound BD-2 in example 1 described above.
Comparative example 4.
An organic light-emitting device was manufactured in the same manner as in example 1, except that the compound D-4 was used instead of the compound BD-2 in example 1 described above.
The organic light emitting devices of examples 1 to 7 and comparative examples 1 to 4 were set at 10mA/cm 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20mA/cm 2 The time required for the initial luminance to be 95% with respect to the initial luminance (LT 95) was measured. The results are shown in table 1 below.
TABLE 1
From table 1 above, it can be confirmed that examples 1 to 7 using the compound of chemical formula 1 of the present application have excellent efficiency and lifetime characteristics compared with comparative examples 1 to 4.
Claims (12)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a silyl group substituted with an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms,
ar1 to Ar4 are the same or different and each is independently a substituted or unsubstituted hydrocarbon ring group having 3 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, wherein the "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, cyano group, silyl group, alkyl group having 1 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, and heterocyclic group having 2 to 30 carbon atoms, or a substituent bonded with 2 or more substituents among the above substituents, or does not have any substituent,
n1 is an integer of 0 to 3, and when n1 is 2 or more, 2 or more R1 s are the same or different from each other,
n2 is an integer of 0 to 5, and when n2 is 2 or more, 2 or more R2 are the same or different from each other.
2. The compound according to claim 1, wherein each of Ar1 to Ar4 is the same or different from each other and is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted hydrogenated naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group, wherein the "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, or a substituent bonded with 2 or more substituents among the above substituents, or does not have any substituent.
3. The compound of claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:
4. the compound of claim 1, wherein the compound has a maximum luminescence peak of 430nm to 470nm.
5. An organic electronic device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 4.
6. The organic electronic device of claim 5, wherein the organic layer comprises a hole injection layer or a hole transport layer, the hole injection layer or the hole transport layer comprising the compound.
7. The organic electronic device of claim 5, wherein the organic layer comprises an electron transport layer or an electron injection layer, the electron transport layer or the electron injection layer comprising the compound.
8. The organic electronic device of claim 5, wherein the organic layer comprises a light-emitting layer comprising the compound.
9. The organic electronic device of claim 5, wherein the organic layer comprises a light-emitting layer comprising the compound as a dopant to the light-emitting layer.
10. The organic electronic device of claim 5, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor OPC, and an organic transistor.
11. The organic electronic device of claim 9, wherein the light emitting layer further comprises the following chemical formula 1-a as a host:
chemical formula 1-A
In the chemical formula 1-a described above,
a1 to A3 are the same or different from each other and each independently is hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
l1 to L3 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
r11 is hydrogen, deuterium, a halogen group, cyano, nitro, silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted phosphino, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q1 is an integer of 0 to 7, and when q1 is 2 or more, 2 or more R11 are the same or different from each other.
12. The organic electronic device according to claim 9, wherein the light-emitting layer further comprises 2 or more of compounds represented by the following chemical formulas 1-B and 1-C as a host:
chemical formula 1-B
Chemical formula 1-C
In the chemical formulas 1-B and 1-C,
a4 to A8 are the same or different from each other and are each independently hydrogen, or a substituted or unsubstituted aryl group,
A9 is a substituted or unsubstituted heterocyclic group,
l4 to L9 are identical to or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
r12 and R13 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, nitro, silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,
q2 and q3 are each integers from 0 to 7, and when q2 and q3 are each 2 or more, substituents in brackets are the same or different from each other.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104672126A (en) * | 2014-12-31 | 2015-06-03 | 北京鼎材科技有限公司 | Benzo-naphtho five-membered heterocycle derivative and application thereof |
| KR20160141361A (en) * | 2015-05-27 | 2016-12-08 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| KR20160141360A (en) * | 2015-05-27 | 2016-12-08 | 삼성디스플레이 주식회사 | Organic light-emitting device |
| WO2017204557A1 (en) * | 2016-05-26 | 2017-11-30 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using same and electronic device therefor |
| CN107698601A (en) * | 2016-08-09 | 2018-02-16 | 株式会社Lg化学 | Heterocyclic compound and the organic electroluminescent device for including it |
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| Publication number | Publication date |
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| WO2019194615A1 (en) | 2019-10-10 |
| KR102206855B1 (en) | 2021-01-25 |
| CN111556865A (en) | 2020-08-18 |
| KR20190116946A (en) | 2019-10-15 |
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