WO2014104720A1 - Organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDFInfo
- Publication number
- WO2014104720A1 WO2014104720A1 PCT/KR2013/012123 KR2013012123W WO2014104720A1 WO 2014104720 A1 WO2014104720 A1 WO 2014104720A1 KR 2013012123 W KR2013012123 W KR 2013012123W WO 2014104720 A1 WO2014104720 A1 WO 2014104720A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- aryl
- membered
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 129
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- 125000005104 aryl silyl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000001769 aryl amino group Chemical group 0.000 claims description 14
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- DRKSMCFPUOMHMK-UHFFFAOYSA-N 2,3,4,5,6,9-hexahydro-1h-carbazole Chemical class C1=CCCC2=C1NC1=C2CCCC1 DRKSMCFPUOMHMK-UHFFFAOYSA-N 0.000 claims description 10
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- -1 2-methylbut-2-enyl Chemical group 0.000 description 52
- 239000010410 layer Substances 0.000 description 48
- 239000000463 material Substances 0.000 description 39
- 238000002360 preparation method Methods 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000002019 doping agent Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 10
- 0 C(*1)C=C(c(cc2)ccc2-c2ccccc2)N=C1[n]1c2cc(-c3ccccc3)ccc2c2c1ccc1c2cccc1 Chemical compound C(*1)C=C(c(cc2)ccc2-c2ccccc2)N=C1[n]1c2cc(-c3ccccc3)ccc2c2c1ccc1c2cccc1 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 5
- 238000001665 trituration Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000002971 oxazolyl group Chemical group 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 125000005493 quinolyl group Chemical group 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000335 thiazolyl group Chemical group 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000004306 triazinyl group Chemical group 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 3
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 3
- WRGKKASJBOREMB-UHFFFAOYSA-N 1,4-dibromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1Br WRGKKASJBOREMB-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- ZGNCKIDXVHSMJL-UHFFFAOYSA-N 2-methylquinoline-8-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=NC(C)=CC=C21 ZGNCKIDXVHSMJL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-M 4-phenylphenolate Chemical compound C1=CC([O-])=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-M 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- NXTRQJAJPCXJPY-UHFFFAOYSA-N 910058-11-6 Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 NXTRQJAJPCXJPY-UHFFFAOYSA-N 0.000 description 1
- KMUVDIRGTVYHND-UHFFFAOYSA-N C(C1)C=Cc(cc2)c1c(c(c1c3)ccc3-c3ccccc3)c2[n]1-c(cc1)ccc1-c1cc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound C(C1)C=Cc(cc2)c1c(c(c1c3)ccc3-c3ccccc3)c2[n]1-c(cc1)ccc1-c1cc(-c2ccccc2)nc(-c2ccccc2)n1 KMUVDIRGTVYHND-UHFFFAOYSA-N 0.000 description 1
- BJKKUSSBTACULY-UHFFFAOYSA-N CC(C)(c1c2)c3cc(-[n]4c(cc(cc5)-c6ccccc6)c5c5c4ccc4c5cccc4)ccc3-c1ccc2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound CC(C)(c1c2)c3cc(-[n]4c(cc(cc5)-c6ccccc6)c5c5c4ccc4c5cccc4)ccc3-c1ccc2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 BJKKUSSBTACULY-UHFFFAOYSA-N 0.000 description 1
- ZUDMWDCEDBSZLF-UHFFFAOYSA-N CC1(C)c2cc(-c3ccnc(-[n]4c(cc(cc5)-c6ccccc6)c5c5c4ccc4c5cccc4)n3)ccc2-c2ccccc12 Chemical compound CC1(C)c2cc(-c3ccnc(-[n]4c(cc(cc5)-c6ccccc6)c5c5c4ccc4c5cccc4)n3)ccc2-c2ccccc12 ZUDMWDCEDBSZLF-UHFFFAOYSA-N 0.000 description 1
- GTJPJGVPTUXBBI-UHFFFAOYSA-N CC1=[O]COC(C)=C1 Chemical compound CC1=[O]COC(C)=C1 GTJPJGVPTUXBBI-UHFFFAOYSA-N 0.000 description 1
- HZNBRKIGJMLFFV-UHFFFAOYSA-N CC1C([n]2c3cc(-c4ccccc4)c(cccc4)c4c3c(cc3)c2cc3-c2ccccc2)=NC(c2cc(-c3ccccc3)ccc2)=NC1c1cccc(-c2ccccc2)c1 Chemical compound CC1C([n]2c3cc(-c4ccccc4)c(cccc4)c4c3c(cc3)c2cc3-c2ccccc2)=NC(c2cc(-c3ccccc3)ccc2)=NC1c1cccc(-c2ccccc2)c1 HZNBRKIGJMLFFV-UHFFFAOYSA-N 0.000 description 1
- GJVGVUGDDYPUFZ-UHFFFAOYSA-N CC1C(c2ccccc2)=CC(c2nc(-c3ccccc3)nc(-[n]3c4cc(-c5ccccc5)c(cccc5)c5c4c(cc4)c3cc4-c3ccccc3)n2)=CC1 Chemical compound CC1C(c2ccccc2)=CC(c2nc(-c3ccccc3)nc(-[n]3c4cc(-c5ccccc5)c(cccc5)c5c4c(cc4)c3cc4-c3ccccc3)n2)=CC1 GJVGVUGDDYPUFZ-UHFFFAOYSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- YCQJSDSFILAATH-UHFFFAOYSA-N Fc(cc1)ccc1-c1nc(-c(cc2)ccc2F)nc(-[n]2c(cc(cc3)-c4ccccc4)c3c3c2ccc2c3cccc2)n1 Chemical compound Fc(cc1)ccc1-c1nc(-c(cc2)ccc2F)nc(-[n]2c(cc(cc3)-c4ccccc4)c3c3c2ccc2c3cccc2)n1 YCQJSDSFILAATH-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- SOKHRJMZRMBWGO-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc([n](c2c3)-c4nc(-c5ccccc5)ccn4)c1c2c(cccc1)c1c3-c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1)cc([n](c2c3)-c4nc(-c5ccccc5)ccn4)c1c2c(cccc1)c1c3-c1ccccc1 SOKHRJMZRMBWGO-UHFFFAOYSA-N 0.000 description 1
- XXPPRJUXDIABDE-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc2c1c(c(cccc1)c1cc1)c1[n]2-c(cc1)ccc1-c1nc(-c2ccccc2)cc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)cc2c1c(c(cccc1)c1cc1)c1[n]2-c(cc1)ccc1-c1nc(-c2ccccc2)cc(-c2ccccc2)n1 XXPPRJUXDIABDE-UHFFFAOYSA-N 0.000 description 1
- DLSYVYFBRPGUCM-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c(cc12)ccc1c(c(cccc1)c1cc1)c1[n]2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c(cc12)ccc1c(c(cccc1)c1cc1)c1[n]2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 DLSYVYFBRPGUCM-UHFFFAOYSA-N 0.000 description 1
- KRLDXLCSWAITEW-UHFFFAOYSA-N c(cc1)ccc1-c(cc12)ccc1c(c(cccc1)c1cc1)c1[n]2-c1nc(-c2cccc(-c3ccccc3)c2)ccn1 Chemical compound c(cc1)ccc1-c(cc12)ccc1c(c(cccc1)c1cc1)c1[n]2-c1nc(-c2cccc(-c3ccccc3)c2)ccn1 KRLDXLCSWAITEW-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000005584 chrysenylene group Chemical group 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000005565 oxadiazolylene group Chemical group 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000005563 perylenylene group Chemical group 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005559 triazolylene group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
Definitions
- the present invention relates to organic electroluminescent compounds and an organic electroluminescent device comprising the same.
- An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
- An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
- the most important factor determining luminous efficiency in the organic EL device is light-emitting materials.
- fluorescent materials have been widely used as light-emitting material.
- phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, phosphorescent light-emitting materials are widely being researched.
- Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
- CBP 4,4’-N,N’-dicarbazol-biphenyl
- BCP bathocuproine
- BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
- Korean Patent Application Laying-Open No. 2005-0100694 discloses compounds for an organic EL device, in which a benzocarbazole backbone is substituted with an aryl group; and Korean Patent Application Laying-Open No. 2010-0015581 discloses compounds for an organic EL device, in which a dibenzocarbazole backbone is substituted with a nitrogen-containing heteroaryl group.
- the above references fail to specifically disclose organic electroluminescent compounds, in which a cycloalkyl group, an aryl group, or a heteroaryl group is bonded to one of the carbon atoms of a benzocarbazole backbone and a nitrogen-containing heteroaryl group is bonded to a nitrogen atom of the benzocarbazole backbone.
- Korean Patent Application Laying-Open No. 2010-0108924 discloses compounds in which an aryl group is bonded to a carbon atom of a benzocarbazole and a nitrogen-containing heteroaryl group is bonded to a nitrogen atom of the benzocarbazole.
- the above reference fails to specifically disclose organic electroluminescent compounds, in which a substituent such as a cycloalkyl group, an aryl group, a hexahydrocarbazole group, or a heteroaryl group is bonded to the 2 position of a benzocarbazole.
- the device using the compound of the above reference needs to be improved in terms of driving voltage, lifespan, and power efficiency.
- the objective of the present invention is to provide an organic electroluminescent compound, which can provide an organic electroluminescent device having a low driving voltage, a long lifespan, and high power efficiency.
- L 1 represents a single bond, a substituted or unsubstituted (3- to 30-membered) heteroarylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (C6-C30)cycloalkylene;
- X 1 and X 2 each independently, represent -CH- or -N-;
- Ar 1 and Ar 2 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
- Ar 3 represents a substituted or unsubstituted (C6-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted hexahydrocarbazole, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
- R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 3 R 4 , -SiR 5 R 6 R 7 , -SR 8 , -OR 9 , a cyano, a nitro or a hydroxyl;
- R 3 to R 9 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
- the organic electroluminescent compound can provide an organic electroluminescent device having a low driving voltage, a long lifespan, and high power efficiency.
- the present invention provides the organic electroluminescent compound of formula 1 above, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the material.
- alkyl includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.
- Alkenyl includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
- Alkynyl includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
- “Cycloalkyl” includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- aryl(ene) indicates a monocyclic or fused ring derived from an aromatic hydrocarbon, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc.
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
- the substituents for the substituted groups of L 1 , Ar 1 to Ar 3 , and R 1 to R 9 of formula 1, each independently, are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl unsubstituted or substituted with a halogen; a (C1-C30)alkoxy; a (C6-C30)aryl; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C3-C30)cycloalkyl; a (5- to 7-membered)heterocycloalkyl; a tri(C1-C30)alkylsilyl
- L 1 represents a single bond, a substituted or unsubstituted (3- to 30-membered)heteroarylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (C6-C30)cycloalkylene; preferably, a single bond, or a substituted or unsubstituted (C6-C20)arylene; and more preferably, a single bond, or a (C6-C15)arylene unsubstituted or substituted with a (C1-C6)alkyl.
- X 1 and X 2 each independently, represent -CH- or -N-.
- Ar 1 and Ar 2 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; preferably, each independently, hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and, more preferably, each independently, hydrogen; a (C1-C6)alkyl; a (C6-C19)aryl unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (5- to 15-member
- Ar 3 represents a substituted or unsubstituted (C6-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted a hexahydrocarbazole, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and preferably, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted hexahydrocarbazole, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.
- Ar 3 represents a (C1-C6)alkyl; a (C6-C19)aryl unsubstituted or substituted with a (5- to 15-membered)heteroaryl or a di(C6-C10)arylamino; a hexahydrocarbazole unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C10)aryl; or a (5- to 19-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl.
- R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR 3 R 4 , -SiR 5 R 6 R 7 , -SR 8 , -OR 9 , a cyano, a nitro or a hydroxyl; and preferably, each independently, hydrogen, a substituted or unsubstituted (C1-C20)alkyl,
- R 1 and R 2 each independently, represent hydrogen; a (C1-C6)alkyl; a (C6-C19)aryl unsubstituted or substituted with a (C1-C6)alkyl; or a (5- to 19-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl.
- R 3 to R 9 each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked with an adjacent substituent(s) to form a substituted or unsubstituted, (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
- L 1 represents a single bond, or a substituted or unsubstituted (C6-C20)arylene;
- X 1 and X 2 each independently, represent -CH- or -N-;
- Ar 1 and Ar 2 each independently, represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;
- Ar 3 represents a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted hexahydrocarbazole, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and
- R 1 and R 2 each independently, represent hydrogen, a substituted or unsubstituted (C1-C20)al
- L 1 represents a single bond, or a (C6-C15)arylene unsubstituted or substituted with a (C1-C6)alkyl
- X 1 and X 2 each independently, represent -CH- or -N-
- Ar 1 and Ar 2 each independently, represent hydrogen; a (C1-C6)alkyl; a (C6-C19)aryl unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (5- to 15-membered)heteroaryl, a tri(C6-C10)arylsilyl, a (C1-C6)alkyldi(C6-C10)arylsilyl, a di(C6-C10)arylamino or a (C1-C6)alkyl(C6-C15)aryl; or a (5
- L 1 represents a single bond, a (3- to 30-membered)heteroarylene or a (C6-C30)arylene
- X 1 and X 2 each independently, represent -CH- or -N-
- Ar 1 and Ar 2 each independently, represent hydrogen, a (C1-C30)alkyl, a (C6-C30)aryl or a (3- to 30-membered)heteroaryl
- Ar 3 represents a (C6-C30)cycloalkyl, a (C6-C30)aryl or a (3- to 30-membered)heteroaryl
- R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl, a (C6-C30)aryl, a (3- to 30-membered)heteroaryl, -NR 3 R 4 or -SiR 5 R 6 R 7 ; R 3 to R 7 , each independently,
- organic electroluminescent compounds of formula 1 of the present invention include the following, but are not limited thereto:
- organic electroluminescent compounds of the present invention can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the following reaction scheme 1.
- L 1 , X 1 , X 2 , Ar 1 to Ar 3 , R 1 , R 2 , a, and b are as defined in formula 1 above, and Hal represents a halogen.
- the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
- the material may consist of the organic electroluminescent compound of formula 1. Otherwise, the material may further comprise a conventional compound(s) which has been comprised of an organic electroluminescent material, in addition to the compound of formula 1.
- the organic electroluminescent device may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
- the organic layer may comprise at least one organic electroluminescent compound of formula 1.
- the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
- the organic layer may comprise a light-emitting layer in which the organic electroluminescent compound of formula 1 may be comprised as a host material, and if needed, another compound(s) other than the compound of formula 1 may be further comprised.
- a phosphorescent dopant which is used for an organic electroluminescent device together with the host material according to the present invention, may be selected from the compounds represented by the following formula 2:
- M 1 is selected from the group consisting of Ir, Pt, Pd and Os;
- L 101 , L 102 and L 103 are each independently selected from the following structures:
- R 201 to R 203 each independently, represent hydrogen, deuterium, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C6-C30)aryl unsubstituted or substituted with a (C1-C30)alkyl, or a halogen;
- R 204 to R 219 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF 5 , a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a
- R 220 to R 223 each independently, represent hydrogen, deuterium, a (C1-C30)alkyl unsubstituted or substituted with a halogen, or a (C6-C30)aryl unsubstituted or substituted with a (C1-C30)alkyl;
- R 224 and R 225 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a halogen, or R 224 and R 225 may be linked with an adjacent substituent(s) to form a (C5-C30), mono- or polycyclic, alicyclic or aromatic ring;
- R 226 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- or 30-membered) heteroaryl or a halogen;
- R 227 to R 229 each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl or a halogen;
- R 231 to R 242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C1-C30)alkoxy, a halogen, a substituted or unsubstituted (C6-C30)aryl, a cyano, or a substituted or unsubstituted (C5-C30)cycloalkyl, or may be linked with an adjacent substituent(s) via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked with R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
- the dopants of formula 2 are preferred as the dopants of formula 2, but the dopants of formula 2 are not limited thereto:
- the present invention provides a composition for preparing an organic electroluminescent device.
- the composition may comprise the compound of the present invention as a host material.
- the organic electroluminescent device of the present invention comprises a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes.
- the organic layer comprises a light-emitting layer in which the composition of the present invention may be comprised.
- the organic electroluminescent device of the present invention comprises the organic electroluminescent compound of formula 1 of the present invention, and may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
- the organic layer may further comprise, in addition to the compound of formula 1, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
- the organic layer may comprise a light-emitting layer and a charge generating layer.
- the organic electroluminescent device of the present invention may emit white light by further comprising at least one light-emitting layer, which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, besides the compound of the present invention.
- a surface layer may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer.
- a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer
- a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
- the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
- the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
- a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
- the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
- the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
- the oxidative dopant includes various Lewis acids and acceptor compounds
- the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
- a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
- dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
- a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
- the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
- Compound 2-2 (14.2 g, 41%) was prepared in the same manner as in the preparation of compound 1-2 of Example 1 by using compound 2-1 (22 g, 128.16 mmol) and 2,5-dibromonitrobenzene (30 g, 106.80 mmol).
- Compound 2-3 (12 g, 92%) was prepared in the same manner as in the preparation of compound 1-2 of Example 1 by using compound 2-2 (14.2 g, 43.27 mmol) and phenylboronic acid (5.3 g, 43.27 mmol).
- Compound C-29 (6.5 g, 81%) was prepared in the same manner as in the preparation of compound C-27 of Example 1 by using compound 2-5 (3.6 g, 13.4 mmol) and compound 1-4 (4.8 g, 13.4 mmol).
- Compound C-54 (6.0 g, 60%) was prepared in the same manner as in the preparation of compound C-27 of Example 1 by using compound 4-1 (6.4 g, 17.30 mmol) and compound 2-5 (5.1 g, 19.10 mmol).
- Compound 5-3 (7.6 g, 92%) was prepared in the same manner as in the preparation of compound 1-2 of Example 1 by using compound 5-2 (7.0 g, 18.80 mmol) and [1,1'-biphenyl]-4-yl boronic acid (4.1 g, 20.70 mmol).
- OLED device was produced using the compound of the present invention.
- a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
- the ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus.
- N 1 ,N 1’ -([1,1’-biphenyl]-4,4’-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
- N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was then introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound C-28 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-11 was introduced into another cell as a dopant.
- the two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 4 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
- 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was then introduced into one cell, and lithium quinolate was introduced into another cell.
- the two materials were evaporated at the same rate, so that they were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer.
- an Al cathode having a thickness of 150 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer.
- All the material used for producing the OLED device were those purified by vacuum sublimation at 10 -6 torr.
- the produced OLED device showed red emission having a luminance of 1,030 cd/m 2 and a current density of 8.7 mA/cm 2 at a driving voltage of 4.1 V.
- the time taken to be reduced to 90% of the luminance at 5,000 nit was 60 hours or more.
- OLED device was produced in the same manner as in Device Example 1, except for using compound C-29 as a host material and compound D-7 as a dopant to form a light-emitting layer.
- the produced OLED device showed red emission having a luminance of 980 cd/m 2 and a current density of 5.5 mA/cm 2 at a driving voltage of 3.8 V.
- the time taken to be reduced to 90% of the luminance at 5,000 nit was 90 hours or more.
- OLED device was produced in the same manner as in Device Example 1, except for using compound C-54 as a host material and compound D-11 as a dopant to form a light-emitting layer.
- the produced OLED device showed red emission having a luminance of 1,020 cd/m 2 and a current density of 11.0 mA/cm 2 at a driving voltage of 3.7 V.
- the time taken to be reduced to 90% of the luminance at 5,000 nit was 60 hours or more.
- OLED device was produced in the same manner as in Device Example 1, except for using compound C-83 as a host material and compound D-11 as a dopant to form a light-emitting layer.
- the produced OLED device showed red emission having a luminance of 950 cd/m 2 and a current density of 10.7 mA/cm 2 at a driving voltage of 3.8 V.
- the time taken to be reduced to 90% of the luminance at 5,000 nit was 75 hours or more.
- OLED device was produced in the same manner as in Device Example 1, except for using compound C-56 as a host material and compound D-7 as a dopant to form a light-emitting layer.
- the produced OLED device showed red emission having a luminance of 980 cd/m 2 and a current density of 7.2 mA/cm 2 at a driving voltage of 3.5 V.
- the time taken to be reduced to 90% of the luminance at 5,000 nit was 90 hours or more.
- OLED device was produced in the same manner as in Device Example 1, except for using compound C-27 as a host material and compound D-7 as a dopant to form a light-emitting layer.
- the produced OLED device showed red emission having a luminance of 1,050 cd/m 2 and a current density of 6.6 mA/cm 2 at a driving voltage of 3.7 V.
- the time taken to be reduced to 90% of the luminance at 5,000 nit was 90 hours or more.
- An OLED device was produced in the same manner as in Device Example 1, except for using compound A-1 shown below as a host material and compound D-11 as a dopant to form a light-emitting layer.
- the produced OLED device showed red emission having a luminance of 1,000 cd/m 2 and a current density of 10.6 mA/cm 2 at a driving voltage of 4.7 V.
- the time taken to be reduced to 90% of the luminance at 5,000 nit was 20 hours or more.
- the organic electroluminescent compound of the present invention can produce an organic electroluminescent device having an excellent lifespan and a lowered driving voltage so that power efficiency is improved. Furthermore, by using the compound of the present invention, it is possible to omit a hole blocking layer which has been necessary for an organic electroluminescent device using a conventional compound.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound according to the present invention, an organic electroluminescent device can have a low driving voltage, a long lifespan, and high power efficiency.
Description
The present invention relates to organic electroluminescent compounds and an organic electroluminescent device comprising the same.
An electroluminescent (EL) device is a self-light-emitting device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. An organic EL device was first developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials to form a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
The most important factor determining luminous efficiency in the organic EL device is light-emitting materials. Until now, fluorescent materials have been widely used as light-emitting material. However, in view of electroluminescent mechanisms, since phosphorescent materials theoretically enhance luminous efficiency by four (4) times compared to fluorescent materials, phosphorescent light-emitting materials are widely being researched. Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp)2), tris(2-phenylpyridine)iridium (Ir(ppy)3) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red-, green- and blue-emitting materials, respectively.
At present, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer (Japan) et al., developed a high performance organic EL device using bathocuproine (BCP) and aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq) etc., as host materials, which were known as hole blocking materials.
Although these materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of the organic EL device is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage. Although the organic EL device comprising phosphorescent host materials provides higher current efficiency (cd/A) than one comprising fluorescent materials, a significantly high driving voltage is necessary. Thus, there is no merit in terms of power efficiency (lm/W). (3) Furthermore, the operational lifespan of the organic EL device is short, and luminous efficiency is still required in order to be improved.
Korean Patent Application Laying-Open No. 2005-0100694 discloses compounds for an organic EL device, in which a benzocarbazole backbone is substituted with an aryl group; and Korean Patent Application Laying-Open No. 2010-0015581 discloses compounds for an organic EL device, in which a dibenzocarbazole backbone is substituted with a nitrogen-containing heteroaryl group. However, the above references fail to specifically disclose organic electroluminescent compounds, in which a cycloalkyl group, an aryl group, or a heteroaryl group is bonded to one of the carbon atoms of a benzocarbazole backbone and a nitrogen-containing heteroaryl group is bonded to a nitrogen atom of the benzocarbazole backbone.
Korean Patent Application Laying-Open No. 2010-0108924 discloses compounds in which an aryl group is bonded to a carbon atom of a benzocarbazole and a nitrogen-containing heteroaryl group is bonded to a nitrogen atom of the benzocarbazole. However, the above reference fails to specifically disclose organic electroluminescent compounds, in which a substituent such as a cycloalkyl group, an aryl group, a hexahydrocarbazole group, or a heteroaryl group is bonded to the 2 position of a benzocarbazole. Furthermore, the device using the compound of the above reference needs to be improved in terms of driving voltage, lifespan, and power efficiency.
The objective of the present invention is to provide an organic electroluminescent compound, which can provide an organic electroluminescent device having a low driving voltage, a long lifespan, and high power efficiency.
The present inventors found that the above objective can be achieved by a compound represented by the following formula 1:
wherein
L1 represents a single bond, a substituted or unsubstituted (3- to 30-membered) heteroarylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (C6-C30)cycloalkylene;
X1 and X2, each independently, represent -CH- or -N-;
Ar1 and Ar2, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
Ar3 represents a substituted or unsubstituted (C6-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted hexahydrocarbazole, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
R1 and R2, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR3R4, -SiR5R6R7, -SR8, -OR9, a cyano, a nitro or a hydroxyl;
R3 to R9, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;
a represents an integer of 1 to 6; b represents an integer of 1 to 3; where a or b represents an integer of 2 or more, each of R1 or R2 may be the same or different; and
the heteroarylene, the heterocycloalkyl and the heteroaryl, each independently, contain at least one hetero atom selected from B, N, O, S, P(=O), Si, and P.
The organic electroluminescent compound, according to the present invention, can provide an organic electroluminescent device having a low driving voltage, a long lifespan, and high power efficiency.
Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
The present invention provides the organic electroluminescent compound of formula 1 above, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the material.
The compound of formula 1 of the present invention is described in detail.
Herein, “alkyl” includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “Alkenyl” includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. “Alkynyl” includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. “Cycloalkyl” includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. “(5- to 7-membered) heterocycloalkyl” indicates a cycloalkyl having 5 to 7 ring backbone atoms including at least one hetero atom selected from B, N, O, S, P(=O), Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. Furthermore, “aryl(ene)” indicates a monocyclic or fused ring derived from an aromatic hydrocarbon, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. “(3- to 30-membered) heteroaryl(ene)” indicates an aryl group having 3 to 30 ring backbone atoms including at least one, preferably 1 to 4, hetero atom selected from the group consisting of B, N, O, S, P(=O), Si, and P; may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, etc. Furthermore, “halogen” includes F, Cl, Br, and I.
Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent. The substituents for the substituted groups of L1, Ar1 to Ar3, and R1 to R9 of formula 1, each independently, are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl unsubstituted or substituted with a halogen; a (C1-C30)alkoxy; a (C6-C30)aryl; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C3-C30)cycloalkyl; a (5- to 7-membered)heterocycloalkyl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a cyano; a di(C1-C30)alkylamino; a di(C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; a (C1-C30)alkyl(C6-C30)aryl; a carboxyl; a nitro; and a hydroxyl; and preferably, at least one selected from the group consisting of deuterium; a halogen; a (C1-C6)alkyl; a (C1-C6)alkoxy; a (C6-C15)aryl; a (5- to 15-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl; a tri(C6-C10)arylsilyl; a (C1-C6)alkyldi(C6-C10)arylsilyl; a di(C6-C10)arylamino; and a (C1-C6)alkyl(C6-C15)aryl.
In formula 1, L1 represents a single bond, a substituted or unsubstituted (3- to 30-membered)heteroarylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (C6-C30)cycloalkylene; preferably, a single bond, or a substituted or unsubstituted (C6-C20)arylene; and more preferably, a single bond, or a (C6-C15)arylene unsubstituted or substituted with a (C1-C6)alkyl.
X1 and X2, each independently, represent -CH- or -N-.
Ar1 and Ar2, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; preferably, each independently, hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and, more preferably, each independently, hydrogen; a (C1-C6)alkyl; a (C6-C19)aryl unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (5- to 15-membered)heteroaryl, a tri(C6-C10)arylsilyl, a (C1-C6)alkyldi(C6-C10)arylsilyl, a di(C6-C10)arylamino, or a (C1-C6)alkyl(C6-C15)aryl; or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C10)aryl.
Ar3 represents a substituted or unsubstituted (C6-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted a hexahydrocarbazole, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and preferably, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted hexahydrocarbazole, or a substituted or unsubstituted (5- to 20-membered)heteroaryl. More preferably, Ar3 represents a (C1-C6)alkyl; a (C6-C19)aryl unsubstituted or substituted with a (5- to 15-membered)heteroaryl or a di(C6-C10)arylamino; a hexahydrocarbazole unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C10)aryl; or a (5- to 19-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl.
R1 and R2, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR3R4, -SiR5R6R7, -SR8, -OR9, a cyano, a nitro or a hydroxyl; and preferably, each independently, hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl. More preferably, R1 and R2, each independently, represent hydrogen; a (C1-C6)alkyl; a (C6-C19)aryl unsubstituted or substituted with a (C1-C6)alkyl; or a (5- to 19-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl.
R3 to R9, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked with an adjacent substituent(s) to form a substituted or unsubstituted, (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur.
According to one embodiment of the present invention, in formula 1 above, L1 represents a single bond, or a substituted or unsubstituted (C6-C20)arylene; X1 and X2, each independently, represent -CH- or -N-; Ar1 and Ar2, each independently, represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; Ar3 represents a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted hexahydrocarbazole, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and R1 and R2, each independently, represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.
According to another embodiment of the present invention, in formula 1 above, L1 represents a single bond, or a (C6-C15)arylene unsubstituted or substituted with a (C1-C6)alkyl; X1 and X2, each independently, represent -CH- or -N-; Ar1 and Ar2, each independently, represent hydrogen; a (C1-C6)alkyl; a (C6-C19)aryl unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (5- to 15-membered)heteroaryl, a tri(C6-C10)arylsilyl, a (C1-C6)alkyldi(C6-C10)arylsilyl, a di(C6-C10)arylamino or a (C1-C6)alkyl(C6-C15)aryl; or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C10)aryl; Ar3 represents a (C6-C19)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (5- to 15-membered)heteroaryl or a di(C6-C10)arylamino; a hexahydrocarbazole unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C10)aryl; or a (5- to 19-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl; and R1 and R2, each independently, represent hydrogen, a (C1-C6)alkyl, a (C6-C19)aryl unsubstituted or substituted with a (C1-C6)alkyl, or a (5- to 19-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl.
Specifically, L1 represents a single bond, a (3- to 30-membered)heteroarylene or a (C6-C30)arylene; X1 and X2, each independently, represent -CH- or -N-; Ar1 and Ar2, each independently, represent hydrogen, a (C1-C30)alkyl, a (C6-C30)aryl or a (3- to 30-membered)heteroaryl; Ar3 represents a (C6-C30)cycloalkyl, a (C6-C30)aryl or a (3- to 30-membered)heteroaryl; R1 and R2, each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl, a (C6-C30)aryl, a (3- to 30-membered)heteroaryl, -NR3R4 or -SiR5R6R7; R3 to R7, each independently, represent hydrogen, deuterium, a halogen, a (C1-C30)alkyl, a (C6-C30)aryl or a (3- to 30-membered)heteroaryl; the arylene and the heteroarylene of L1 and the alkyl, the cycloalkyl, the aryl and the heteroaryl of Ar1, Ar2, and R1 to R9 may be further substituted with at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C6-C30)aryl, a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a tri(C1-C30)alkylsilyl, a tri(C6-C30)arylsilyl, a di(C1-C30)alkyl(C6-C30)arylsilyl, a (C1-C30)alkyldi(C6-C30)arylsilyl, a di(C1-C30)alkylamino, a di(C6-C30)arylamino, a (C1-C30)alkyl(C6-C30)arylamino, and a (C1-C30)alkyl(C6-C30)aryl.
More specifically, L1 represents a single bond, phenylene, biphenylene, terphenylene, indenylene, fluorenylene, triphenylenylene, pyrenylene, perylenylene, chrysenylene, naphthacenylene, fluoranthenylene, thiophenylene, pyrrolylene, pyrazolylene, thiazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, furazanylene, pyridylene, benzofuranylene, benzothiophenylene, indolylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzoxazolylene, benzothiadiazolylene, dibenzofuranylene or dibenzothiophenylene; Ar1 and Ar2, each independently, represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl, fluoranthenyl, terphenylyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, or quinoxalinyl; R1 and R2, each independently, represent hydrogen, deuterium, chloro, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, anthryl, biphenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, indenyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl or triphenylsilyl; the groups of L1, Ar1, Ar2, R1 and R2 may be further substituted with at least one selected from the group consisting of deuterium, chloro, fluoro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, methyldiphenylsilyl, triphenylsilyl, N-carbazolyl, and N-phenylcarbazolyl.
Even more specifically, organic electroluminescent compounds of formula 1 of the present invention include the following, but are not limited thereto:
The organic electroluminescent compounds of the present invention can be prepared by a synthetic method known to one skilled in the art. For example, they can be prepared according to the following reaction scheme 1.
[Reaction Scheme 1]
In reaction scheme 1, L1, X1, X2, Ar1 to Ar3, R1, R2, a, and b are as defined in formula 1 above, and Hal represents a halogen.
The present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the material.
The material may consist of the organic electroluminescent compound of formula 1. Otherwise, the material may further comprise a conventional compound(s) which has been comprised of an organic electroluminescent material, in addition to the compound of formula 1.
The organic electroluminescent device may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes. The organic layer may comprise at least one organic electroluminescent compound of formula 1.
One of the first and second electrodes may be an anode, and the other may be a cathode. The organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
Furthermore, the organic layer may comprise a light-emitting layer in which the organic electroluminescent compound of formula 1 may be comprised as a host material, and if needed, another compound(s) other than the compound of formula 1 may be further comprised.
In addition, a phosphorescent dopant, which is used for an organic electroluminescent device together with the host material according to the present invention, may be selected from the compounds represented by the following formula 2:
wherein
M1 is selected from the group consisting of Ir, Pt, Pd and Os;
L101, L102 and L103 are each independently selected from the following structures:
R201 to R203, each independently, represent hydrogen, deuterium, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C6-C30)aryl unsubstituted or substituted with a (C1-C30)alkyl, or a halogen;
R204 to R219, each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C2-C30)alkenyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF5, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a cyano or a halogen;
R220 to R223, each independently, represent hydrogen, deuterium, a (C1-C30)alkyl unsubstituted or substituted with a halogen, or a (C6-C30)aryl unsubstituted or substituted with a (C1-C30)alkyl;
R224 and R225, each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a halogen, or R224 and R225 may be linked with an adjacent substituent(s) to form a (C5-C30), mono- or polycyclic, alicyclic or aromatic ring;
R226 represents a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- or 30-membered) heteroaryl or a halogen;
R227 to R229, each independently, represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl or a halogen;
Q represents 
or 
R231 to R242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl unsubstituted or substituted with a halogen, a (C1-C30)alkoxy, a halogen, a substituted or unsubstituted (C6-C30)aryl, a cyano, or a substituted or unsubstituted (C5-C30)cycloalkyl, or may be linked with an adjacent substituent(s) via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked with R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
Specifically, the following compounds are preferred as the dopants of formula 2, but the dopants of formula 2 are not limited thereto:
Furthermore, the present invention provides a composition for preparing an organic electroluminescent device. The composition may comprise the compound of the present invention as a host material.
The organic electroluminescent device of the present invention comprises a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes. The organic layer comprises a light-emitting layer in which the composition of the present invention may be comprised.
The organic electroluminescent device of the present invention comprises the organic electroluminescent compound of formula 1 of the present invention, and may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
In the organic electroluminescent device of the present invention, the organic layer may further comprise, in addition to the compound of formula 1, at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising said metal. The organic layer may comprise a light-emitting layer and a charge generating layer.
In addition, the organic electroluminescent device of the present invention may emit white light by further comprising at least one light-emitting layer, which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, besides the compound of the present invention.
In the organic electroluminescent device of the present invention, at least one layer (hereinafter, "a surface layer”) may be placed on an inner surface(s) of one or both electrode(s), selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer. Specifically, a chalcogenide (includes oxides) layer of silicon or aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In the organic electroluminescent device of the present invention, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
In order to form each layer of the organic electroluminescent device of the present invention, dry film-forming methods such as vacuum evaporation, sputtering, plasma and ion plating methods, or wet film-forming methods such as spin coating, dip coating, and flow coating methods can be used.
When using a wet film-forming method, a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
Hereinafter, the organic electroluminescent compound, the preparation method of the compound, and the luminescent characteristics of the device will be explained in detail with reference to the following examples.
Example 1: Preparation of compound C-27
Preparation of compound 1-2
Compound 1-1 (18.5 g, 66 mmol), 2,5-dibromonitrobenzene (18 g, 72.6 mmol), Na2CO3 (16.8 g, 158.4 mmol), and Pd(PPh3)4 (3.8 g, 3.3 mmol) were added to a mixture of toluene (320 mL), ethanol (80 mL), and purified water (80 mL). The mixture was stirred at 90-100 ℃ for 3 hours. After completing the reaction, the mixture was stood to remove an aqueous layer. The organic layer was concentrated, was subjected to trituration with methylene chloride (MC), and was filtered to obtain compound 1-2 (19 g, 71.2%).
Preparation of compound 1-3
Compound 1-2 (10 g, 24.7 mmol), phenylboronic acid (3.6 g, 29.7 mmol), Na2CO3 (7.8 g, 74.1 mmol) and Pd(PPh3)4 (1.4 g, 1.2 mmol) were added to a mixture of toluene (150 mL), ethanol (37 mL), and purified water (37 mL). The mixture was stirred at 90-100 ℃ for 3 hours. After completing the reaction, the mixture was cooled to room temperature, and then was stood to remove an aqueous layer. The organic layer was concentrated, was subjected to trituration with MC, and was filtered to obtain compound 1-3 (9 g, 90.9%).
Preparation of compound 1-4
Compound 1-3 (9 g, 22.4 mmol) was dissolved in P(OEt)3 (100 mL). The mixture was stirred at 160 ℃ for a day, and then was distilled under vacuum to remove P(OEt)3. Thereafter, the mixture was extracted with MC and distilled water, was subjected to trituration with MC, and then was filtered to obtain compound 1-4 (4.9 g, 60%).
Preparation of compound C-27
After suspending compound 1-4 (4.0 g, 10.83 mmol) and compound 1-5 (3.1 g, 11.91 mmol) in dimethylformamide (DMF) (80 mL), 60% NaH (702 mg, 16.1 mmol) was added to the mixture at room temperature. Thereafter, the mixture was stirred for 12 hours, and then purified water (1L) was added thereto. After a filteration under reduced pressure, the obtained solids was subjected to trituration with methanol/ethylacetate (EA), was dissolved in MC, was filtered through silica, and then was subjected to trituration with MC/n-hexane to obtain compound C-27 (4.5 g, 69%).
MW : 600.71, UV : 382 nm, PL : 493 nm, melting point : 324 ℃
Example 2: Preparation of compound C-28
Preparation of compound 2-2
Compound 2-2 (14.2 g, 41%) was prepared in the same manner as in the preparation of compound 1-2 of Example 1 by using compound 2-1 (22 g, 128.16 mmol) and 2,5-dibromonitrobenzene (30 g, 106.80 mmol).
Preparation of compound 2-3
Compound 2-3 (12 g, 92%) was prepared in the same manner as in the preparation of compound 1-2 of Example 1 by using compound 2-2 (14.2 g, 43.27 mmol) and phenylboronic acid (5.3 g, 43.27 mmol).
Preparation of compound 2-4
After dissolving compound 2-3 (12 g, 36.88 mmol) in triethylphosphate (120 mL), compound 2-4 (6.4 g, 62%) was prepared in the same manner as in the preparation of compound 1-3 of Example 1.
Preparation of compound C-28
Compound C-28 (6.4 g, 58%) was prepared in the same manner as in the preparation of compound C-27 of Example 1 by using compound 2-4 (6.4 g, 21.81 mmol) and compound 2-5 (5.8 g, 23.99 mmol).
MW : 524.61, UV : 334 nm, PL : 495 nm, melting point: 273 ℃
Example 3: Preparation of compound C-29
Compound C-29 (6.5 g, 81%) was prepared in the same manner as in the preparation of compound C-27 of Example 1 by using compound 2-5 (3.6 g, 13.4 mmol) and compound 1-4 (4.8 g, 13.4 mmol).
MW : 600.71, UV : 334 nm, PL : 385 nm, melting point: 349 ℃
Example 4: Preparation of compound C-54
Compound C-54 (6.0 g, 60%) was prepared in the same manner as in the preparation of compound C-27 of Example 1 by using compound 4-1 (6.4 g, 17.30 mmol) and compound 2-5 (5.1 g, 19.10 mmol).
MW : 676.81, UV : 344 nm, PL : 495 nm, melting point: 336 ℃
Example 5: Preparation of compound C-56
Preparation of compound 5-2
After dissolving compound 5-1 (35 g, 86.60 mmol) in triethylphosphate (350 mL), compound 5-2 (7.0 g, 22%) was prepared in the same manner as in the preparation of compound 1-4 of Example 1.
Preparation of compound 5-3
Compound 5-3 (7.6 g, 92%) was prepared in the same manner as in the preparation of compound 1-2 of Example 1 by using compound 5-2 (7.0 g, 18.80 mmol) and [1,1'-biphenyl]-4-yl boronic acid (4.1 g, 20.70 mmol).
Preparation of compound C-56
Compound C-56 (4 g, 70%) was prepared in the same manner as in the preparation of compound C-27 of Example 1 by using compound 5-3 (3.8 g, 8.53 mmol) and compound 2-5 (2.5 g, 9.38 mmol).
MW : 599.72, UV : 324 nm, PL : 485 nm, melting point: 264 ℃
Example 6: Preparation of compound C-83
Preparation of compound 6-1
After dissolving compound 2-4 (3.7 g, 13 mmol) and cyanuric acid (12 g, 63 mmol) in tetrahydrofuran (THF) (300 mL), compound 6-1 (4.3 g, 77%) was prepared in the same manner as in the preparation of compound C-27 of Example 1.
Preparation of compound C-83
Compound C-83 (37 g, 62%) was prepared in the same manner of in the preparation of compound 1-2 of Example 1 by using compound 6-1 (4 g, 9 mmol) and 3-biphenyl boronic acid (7.2 g, 36 mmol).
MW : 599.72, UV : 324 nm, PL : 485 nm, melting point: 264 ℃
[Device Example 1] Production of an OLED device using the organic
electroluminescent compound of the present invention
OLED device was produced using the compound of the present invention. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor depositing apparatus. N1,N1’-([1,1’-biphenyl]-4,4’-diyl)bis(N1-(naphthalen-1-yl)-N4,N4-diphenylbenzene-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was then introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying an electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound C-28 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-11 was introduced into another cell as a dopant. The two materials were evaporated at different rates, so that the dopant was deposited in a doping amount of 4 wt% based on the total amount of the host and dopant to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was then introduced into one cell, and lithium quinolate was introduced into another cell. The two materials were evaporated at the same rate, so that they were respectively deposited in a doping amount of 50 wt% to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. After depositing lithium quinolate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was then deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the material used for producing the OLED device were those purified by vacuum sublimation at 10-6 torr.
The produced OLED device showed red emission having a luminance of 1,030 cd/m2 and a current density of 8.7 mA/cm2 at a driving voltage of 4.1 V. The time taken to be reduced to 90% of the luminance at 5,000 nit was 60 hours or more.
[Device Example 2] Production of an OLED device using the organic
electroluminescent compound of the present invention
OLED device was produced in the same manner as in Device Example 1, except for using compound C-29 as a host material and compound D-7 as a dopant to form a light-emitting layer.
The produced OLED device showed red emission having a luminance of 980 cd/m2 and a current density of 5.5 mA/cm2 at a driving voltage of 3.8 V. The time taken to be reduced to 90% of the luminance at 5,000 nit was 90 hours or more.
[Device Example 3] Production of an OLED device using the organic
electroluminescent compound of the present invention
OLED device was produced in the same manner as in Device Example 1, except for using compound C-54 as a host material and compound D-11 as a dopant to form a light-emitting layer.
The produced OLED device showed red emission having a luminance of 1,020 cd/m2 and a current density of 11.0 mA/cm2 at a driving voltage of 3.7 V. The time taken to be reduced to 90% of the luminance at 5,000 nit was 60 hours or more.
[Device Example 4] Production of an OLED device using the organic
electroluminescent compound of the present invention
OLED device was produced in the same manner as in Device Example 1, except for using compound C-83 as a host material and compound D-11 as a dopant to form a light-emitting layer.
The produced OLED device showed red emission having a luminance of 950 cd/m2 and a current density of 10.7 mA/cm2 at a driving voltage of 3.8 V. The time taken to be reduced to 90% of the luminance at 5,000 nit was 75 hours or more.
[Device Example 5] Production of an OLED device using the organic
electroluminescent compound of the present invention
OLED device was produced in the same manner as in Device Example 1, except for using compound C-56 as a host material and compound D-7 as a dopant to form a light-emitting layer.
The produced OLED device showed red emission having a luminance of 980 cd/m2 and a current density of 7.2 mA/cm2 at a driving voltage of 3.5 V. The time taken to be reduced to 90% of the luminance at 5,000 nit was 90 hours or more.
[Device Example 6] Production of an OLED device using the organic
electroluminescent compound of the present invention
OLED device was produced in the same manner as in Device Example 1, except for using compound C-27 as a host material and compound D-7 as a dopant to form a light-emitting layer.
The produced OLED device showed red emission having a luminance of 1,050 cd/m2 and a current density of 6.6 mA/cm2 at a driving voltage of 3.7 V. The time taken to be reduced to 90% of the luminance at 5,000 nit was 90 hours or more.
[Comparative Device Example 1] Production of an OLED device by using
conventional organic electroluminescent compounds
An OLED device was produced in the same manner as in Device Example 1, except for using compound A-1 shown below as a host material and compound D-11 as a dopant to form a light-emitting layer.
The produced OLED device showed red emission having a luminance of 1,000 cd/m2 and a current density of 10.6 mA/cm2 at a driving voltage of 4.7 V. The time taken to be reduced to 90% of the luminance at 5,000 nit was 20 hours or more.
The organic electroluminescent compound of the present invention can produce an organic electroluminescent device having an excellent lifespan and a lowered driving voltage so that power efficiency is improved. Furthermore, by using the compound of the present invention, it is possible to omit a hole blocking layer which has been necessary for an organic electroluminescent device using a conventional compound.
Claims (6)
- An organic electroluminescent compound represented by the following formula 1:
whereinL1 represents a single bond, a substituted or unsubstituted (3- to 30-membered) heteroarylene, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (C6-C30)cycloalkylene;X1 and X2, each independently, represent -CH- or -N-;Ar1 and Ar2, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;Ar3 represents a substituted or unsubstituted (C6-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted hexahydrocarbazole, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;R1 and R2, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -NR3R4, -SiR5R6R7, -SR8, -OR9, a cyano, a nitro or a hydroxyl;R3 to R9, each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (5- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted, (3- to 30-membered), mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;a represents an integer of 1 to 6; b represents an integer of 1 to 3; where a or b represents an integer of 2 or more, each of R1 or R2 may be the same or different; andthe heteroarylene, the heterocycloalkyl and the heteroaryl, each independently, contain at least one hetero atom selected from B, N, O, S, P(=O), Si, and P. - The organic electroluminescent compound according to claim 1, wherein the substituents for the substituted groups of L1, Ar1 to Ar3, and R1 to R9, each independently, are at least one selected from the group consisting of deuterium; a halogen; a (C1-C30)alkyl unsubstituted or substituted with a halogen; a (C1-C30)alkoxy; a (C6-C30)aryl; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C3-C30)cycloalkyl; a (5- to 7-membered) heterocycloalkyl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a cyano; a di(C1-C30)alkylamino; a di(C6-C30)arylamino; a (C1-C30)alkyl(C6-C30)arylamino; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; a (C1-C30)alkyl(C6-C30)aryl; a carboxyl; a nitro; and a hydroxyl.
- The organic electroluminescent compound according to claim 1, whereinL1 represents a single bond, or a substituted or unsubstituted (C6-C20)arylene;X1 and X2, each independently, represent -CH- or -N-;Ar1 and Ar2, each independently, represent hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;Ar3 represents a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted hexahydrocarbazole, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; andR1 and R2, each independently, represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.
- The organic electroluminescent compound according to claim 1, whereinL1 represents a single bond, or an (C6-C15)arylene unsubstituted or substituted with a (C1-C6)alkyl;X1 and X2, each independently, represent -CH- or -N-;Ar1 and Ar2, each independently, represent hydrogen; a (C1-C6)alkyl; a (C6-C19)aryl unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl, a (C1-C6)alkoxy, a (5- to 15-membered)heteroaryl, a tri(C6-C10)arylsilyl, a (C1-C6)alkyldi(C6-C10)arylsilyl, a di(C6-C10)arylamino, or a (C1-C6)alkyl(C6-C15)aryl; or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C10)aryl;Ar3 represents a (C6-C19)aryl unsubstituted or substituted with a (C1-C6)alkyl, a (5- to 15-membered)heteroaryl, or a di(C6-C10)arylamino; a hexahydrocarbazole unsubstituted or substituted with a (C1-C6)alkyl or a (C6-C10)aryl; or a (5- to 19-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl; andR1 and R2, each independently, represent hydrogen, a (C1-C6)alkyl, a (C6-C19)aryl unsubstituted or substituted with a (C1-C6)alkyl, or a (5- to 19-membered)heteroaryl unsubstituted or substituted with a (C6-C10)aryl.
- The organic electroluminescent compound according to claim 1, wherein the compound of formula 1 is selected from the group consisting of:
- An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201380065763.8A CN104870434A (en) | 2012-12-24 | 2013-12-24 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2012-0152219 | 2012-12-24 | ||
| KR1020120152219A KR20140082351A (en) | 2012-12-24 | 2012-12-24 | Organic Electroluminescent Compounds and Organic Electroluminescent Device Comprising the Same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2014104720A1 true WO2014104720A1 (en) | 2014-07-03 |
Family
ID=51021686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/KR2013/012123 WO2014104720A1 (en) | 2012-12-24 | 2013-12-24 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
Country Status (4)
| Country | Link |
|---|---|
| KR (1) | KR20140082351A (en) |
| CN (1) | CN104870434A (en) |
| TW (1) | TW201435043A (en) |
| WO (1) | WO2014104720A1 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016129819A1 (en) * | 2015-02-12 | 2016-08-18 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN107231801A (en) * | 2015-02-12 | 2017-10-03 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and the Organnic electroluminescent device comprising organic electroluminescent compounds |
| WO2018056645A1 (en) * | 2016-09-22 | 2018-03-29 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent device comprising an electron buffer layer and an electron transport layer |
| JP2019500316A (en) * | 2015-10-22 | 2019-01-10 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| US11107997B2 (en) | 2016-09-22 | 2021-08-31 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent device comprising an electron buffer layer and an electron transport layer |
| CN113544133A (en) * | 2019-08-20 | 2021-10-22 | 株式会社Lg化学 | Novel compound and organic light emitting device using the same |
| US11563183B2 (en) | 2017-06-21 | 2023-01-24 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| US11588111B2 (en) | 2017-08-04 | 2023-02-21 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting device including the same |
| US12084433B2 (en) | 2018-03-23 | 2024-09-10 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101864473B1 (en) * | 2014-09-22 | 2018-06-04 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| WO2016195370A1 (en) * | 2015-06-01 | 2016-12-08 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device including same |
| KR20170109430A (en) * | 2016-03-21 | 2017-09-29 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR102620860B1 (en) * | 2016-06-14 | 2024-01-03 | 솔루스첨단소재 주식회사 | Organic light-emitting compound and organic electroluminescent device using the same |
| CN111063818A (en) * | 2019-12-26 | 2020-04-24 | 武汉华星光电半导体显示技术有限公司 | Display panel and preparation method thereof |
| CN111129330A (en) * | 2019-12-26 | 2020-05-08 | 武汉华星光电半导体显示技术有限公司 | Display panel and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011019156A1 (en) * | 2009-08-10 | 2011-02-17 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| KR20120021203A (en) * | 2010-08-31 | 2012-03-08 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| US20130048956A1 (en) * | 2011-08-26 | 2013-02-28 | E-Ray Optoelectronics Technology Co., Ltd. | Compound for electroluminescent device and organic electroluminescent devices using the same |
| WO2013105747A1 (en) * | 2012-01-13 | 2013-07-18 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using same and electronic device thereof |
-
2012
- 2012-12-24 KR KR1020120152219A patent/KR20140082351A/en not_active Application Discontinuation
-
2013
- 2013-12-24 WO PCT/KR2013/012123 patent/WO2014104720A1/en active Application Filing
- 2013-12-24 CN CN201380065763.8A patent/CN104870434A/en active Pending
- 2013-12-24 TW TW102147927A patent/TW201435043A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011019156A1 (en) * | 2009-08-10 | 2011-02-17 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| KR20120021203A (en) * | 2010-08-31 | 2012-03-08 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| US20130048956A1 (en) * | 2011-08-26 | 2013-02-28 | E-Ray Optoelectronics Technology Co., Ltd. | Compound for electroluminescent device and organic electroluminescent devices using the same |
| WO2013105747A1 (en) * | 2012-01-13 | 2013-07-18 | 덕산하이메탈(주) | Compound for organic electronic element, organic electronic element using same and electronic device thereof |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016129819A1 (en) * | 2015-02-12 | 2016-08-18 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN107231801A (en) * | 2015-02-12 | 2017-10-03 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and the Organnic electroluminescent device comprising organic electroluminescent compounds |
| CN107231801B (en) * | 2015-02-12 | 2021-03-23 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent devices comprising the same |
| JP2019500316A (en) * | 2015-10-22 | 2019-01-10 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| WO2018056645A1 (en) * | 2016-09-22 | 2018-03-29 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent device comprising an electron buffer layer and an electron transport layer |
| US11107997B2 (en) | 2016-09-22 | 2021-08-31 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent device comprising an electron buffer layer and an electron transport layer |
| US11563183B2 (en) | 2017-06-21 | 2023-01-24 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| US11844273B2 (en) | 2017-06-21 | 2023-12-12 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| US11588111B2 (en) | 2017-08-04 | 2023-02-21 | Samsung Display Co., Ltd. | Condensed-cyclic compound and organic light-emitting device including the same |
| US12084433B2 (en) | 2018-03-23 | 2024-09-10 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| CN113544133A (en) * | 2019-08-20 | 2021-10-22 | 株式会社Lg化学 | Novel compound and organic light emitting device using the same |
| CN113544133B (en) * | 2019-08-20 | 2023-10-13 | 株式会社Lg化学 | Compound and organic light emitting device using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104870434A (en) | 2015-08-26 |
| TW201435043A (en) | 2014-09-16 |
| KR20140082351A (en) | 2014-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2014104720A1 (en) | Organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| EP3446345A1 (en) | A plurality of host materials and organic electroluminescent device comprising the same | |
| WO2013032297A1 (en) | Benzocarbazole compounds and electroluminescent devices involving them | |
| EP2694619A1 (en) | Novel organic electroluminescent compounds and an organic electroluminescent device using the same | |
| WO2013073874A1 (en) | Novel organic electroluminescent compounds and an organic electroluminescent device using the same | |
| WO2015012618A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2015099485A1 (en) | An organic electroluminescent compound and an organic electroluminescent device comprising the same | |
| EP2828254A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2015084114A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2014038867A1 (en) | A novel combination of a host compound and a dopant compound and an organic electroluminescence device comprising the same | |
| WO2012141499A1 (en) | Novel compounds for organic electronic material and organic electroluminescent device using the same | |
| WO2013073896A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2014196805A1 (en) | Organic electroluminescent compound and organic electroluminescent device comprising the same | |
| WO2013151297A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2013180478A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device containing the same | |
| WO2015037965A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2015099486A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2013081416A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2015056993A1 (en) | Combination of a host compound and a dopant compound and organic electroluminescent device comprising the same | |
| WO2013012297A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device using the same | |
| WO2013109045A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device using the same | |
| WO2013073859A1 (en) | Novel organic electroluminescence compounds and organic electroluminescence device comprising the same | |
| EP2841527A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device comprising the same | |
| WO2014061991A1 (en) | Novel organic electroluminescent compounds and organic electroluminescent device containing the same | |
| WO2013012298A1 (en) | 9h-carbazole compounds and electroluminescent devices involving them |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13869252 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 13869252 Country of ref document: EP Kind code of ref document: A1 |