JP2016001749A - 新規有機電界発光化合物およびこれを使用する有機電界発光素子 - Google Patents
新規有機電界発光化合物およびこれを使用する有機電界発光素子 Download PDFInfo
- Publication number
- JP2016001749A JP2016001749A JP2015160532A JP2015160532A JP2016001749A JP 2016001749 A JP2016001749 A JP 2016001749A JP 2015160532 A JP2015160532 A JP 2015160532A JP 2015160532 A JP2015160532 A JP 2015160532A JP 2016001749 A JP2016001749 A JP 2016001749A
- Authority
- JP
- Japan
- Prior art keywords
- organic electroluminescent
- compound
- aryl
- alkyl
- mmol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 160
- 239000000126 substance Substances 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 239000010410 layer Substances 0.000 claims description 16
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 12
- -1 amine compounds Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 11
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 7
- 125000005104 aryl silyl group Chemical group 0.000 claims description 7
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 6
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 5
- 239000002019 doping agent Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 4
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 4
- 125000006820 (C1-C60) alkylthio group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 4
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000005106 triarylsilyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 claims 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 47
- 239000000463 material Substances 0.000 abstract description 37
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000000034 method Methods 0.000 description 26
- 239000000203 mixture Substances 0.000 description 23
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 239000012153 distilled water Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 0 C*c1c2[o]c(cccc3)c3c2ccc1 Chemical compound C*c1c2[o]c(cccc3)c3c2ccc1 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-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
- 125000002950 monocyclic group Chemical group 0.000 description 2
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000002061 vacuum sublimation Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 125000006753 (C1-C60) heteroaryl group Chemical group 0.000 description 1
- JKATVFUXWHHCFA-UHFFFAOYSA-N 1,4-dibromo-2,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=C(Br)C=CC(Br)=C1[N+]([O-])=O JKATVFUXWHHCFA-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- JNGKNTZYAKKNLQ-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1h-triazine Chemical compound N=1N(Cl)NC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 JNGKNTZYAKKNLQ-UHFFFAOYSA-N 0.000 description 1
- FRNLBIWVMVNNAZ-UHFFFAOYSA-N 2-iodonaphthalene Chemical compound C1=CC=CC2=CC(I)=CC=C21 FRNLBIWVMVNNAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- KOAYJGBVKMFCPY-UHFFFAOYSA-N 3-chloro-1,5-diphenyl-2h-pyridine Chemical compound C1C(Cl)=CC(C=2C=CC=CC=2)=CN1C1=CC=CC=C1 KOAYJGBVKMFCPY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 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
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-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
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- VNICRWVQYFRWDK-UHFFFAOYSA-N naphthalen-2-ylhydrazine Chemical compound C1=CC=CC2=CC(NN)=CC=C21 VNICRWVQYFRWDK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/022—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position not provided for in one of the sub groups C09B5/04 - C09B5/20
- C09B5/028—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position not provided for in one of the sub groups C09B5/04 - C09B5/20 only N-containing hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/2409—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62
- C09B5/2436—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62 only nitrogen-containing hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen 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
- H10K85/654—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
-
- 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
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
-
- 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
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
【解決手段】6員環・5員環・6員環・5員環・6員環がこの順に縮合した新規の有機電界発光化合物およびこれを含む有機電界発光素子。非常に良好な駆動寿命を有するOLED素子を製造するために使用されうる。
【選択図】なし
Description
Z1〜Z8は独立してC(Ar3)およびNから選択され、Ar3は互いに異なっていてもよく、並びに隣り合うAr3基は一緒に結合して環を形成していてもよく;
Ar1およびAr2は独立して(C1−C60)アルキル、(C3−C60)シクロアルキル、N、O、S、SiおよびPから選択される1以上のヘテロ原子を含む5員もしくは6員のヘテロシクロアルキル、(C7−C60)ビシクロアルキル、アダマンチル、(C2−C60)アルケニル、(C2−C60)アルキニル、(C6−C60)アリールおよび(C3−C60)ヘテロアリールから選択され;
Ar3は独立して水素、(C1−C60)アルキル、ハロゲン、シアノ、(C3−C60)シクロアルキル、N、O、S、SiおよびPから選択される1以上のヘテロ原子を含む5員もしくは6員のヘテロシクロアルキル、(C7−C60)ビシクロアルキル、アダマンチル、(C2−C60)アルケニル、(C2−C60)アルキニル、(C6−C60)アリール、(C1−C60)アルコキシ、(C6−C60)アリールオキシ、(C3−C60)ヘテロアリール、(C6−C60)アリールチオ、(C1−C60)アルキルチオ、モノもしくはジ(C1−C30)アルキルアミノ、モノもしくはジ(C6−C30)アリールアミノ、トリ(C1−C30)アルキルシリル、ジ(C1−C30)アルキル(C6−C30)アリールシリル、トリ(C6−C30)アリールシリル、モノもしくはジ(C6−C30)アリールボラニル、モノもしくはジ(C1−C60)アルキルボラニル、ニトロおよびヒドロキシルから選択され;並びに
Ar1〜Ar3のアルキル、シクロアルキル、ヘテロシクロアルキル、ビシクロアルキル、アダマンチル、アルケニル、アルキニル、アリール、アルコキシ、アリールオキシ、ヘテロアリール、アリールチオ、アルキルチオ、アルキルアミノ、アリールアミノ、トリアルキルシリル、ジアルキルアリールシリル、トリアリールシリル、アリールボラニルもしくはアルキルボラニルは、(C1−C60)アルキル、ハロゲン、シアノ、(C3−C60)シクロアルキル、N、O、S、SiおよびPから選択される1以上のヘテロ原子を含む5員もしくは6員のヘテロシクロアルキル、(C7−C60)ビシクロアルキル、アダマンチル、(C2−C60)アルケニル、(C2−C60)アルキニル、(C6−C60)アリール、(C1−C60)アルコキシ、(C6−C60)アリールオキシ、P(=O)RaRbで置換された(C6−C60)アリール[RaおよびRbは独立して(C1−C60)アルキルもしくは(C6−C60)アリールを表す]、(C3−C60)ヘテロアリール、(C6−C60)アリールで置換された(C3−C60)ヘテロアリール、(C1−C60)アルキルで置換された(C3−C60)ヘテロアリール、(C6−C60)アリール(C1−C60)アルキル、(C6−C60)アリールチオ、(C1−C60)アルキルチオ、モノもしくはジ(C1−C30)アルキルアミノ、モノもしくはジ(C6−C30)アリールアミノ、トリ(C1−C30)アルキルシリル、ジ(C1−C30)アルキル(C6−C30)アリールシリル、トリ(C6−C30)アリールシリル、モノもしくはジ(C6−C30)アリールボラニル、モノもしくはジ(C1−C60)アルキルボラニル、ニトロおよびヒドロキシルからなる群から選択される1種以上の置換基によってさらに置換されていてよく、
ただし、XおよびYの双方がN(Ar1)であり、かつZ1〜Z8の全てがC(Ar3)である場合を除く。
ブロモ−2−ニトロベンゼン(30g、148.5mmol)、1−ナフタレンボロン酸(30.6g、178.2mmol)、Pd(PPh3)4(5.14g、4.45mmol)、2MのK2CO3水溶液(297.01mmol)、トルエン(500mL)およびエタノール(200mL)の混合物を還流下で4時間攪拌した。この混合物を周囲温度まで冷却した後で、これに蒸留水を添加した。得られた混合物を酢酸エチルで抽出し、その抽出物を硫酸マグネシウムで乾燥させ、減圧下で蒸留した。カラムを通した精製で化合物(A−1)(31g、124.3mmol、84.03%)を得た。
化合物(A−1)(31g、124.3mmol)およびトリエチルホスファイト(300mL)の混合物を還流下で10時間攪拌した。この混合物を周囲温度まで冷却した後で、減圧下で有機溶媒を蒸留除去した。これに蒸留水を添加し、混合物を酢酸エチルで抽出した。この抽出物を硫酸マグネシウムで乾燥させ、減圧下で蒸留した。カラムを通した精製で化合物(A−2)(18g、82.84mmol、66.81%)を得た。
化合物(A−2)(18g、82.84mmol)、1,5−ジフェニル−3−クロロピリジン(26.4g、99.41mmol)、Pd(OAc)2(1.85g、8.28mmol)、P(t−bu)3(8.17ml、16.5mmol、キシレン中50%)、NaOt−bu(23.8g、248.5mmol)およびトルエン(500mL)の混合物を還流下で12時間攪拌した。この混合物を周囲温度まで冷却した後で、これに蒸留水を添加し、混合物を酢酸エチルで抽出した。この抽出物を硫酸マグネシウムで乾燥させ、減圧下で蒸留した。カラムを通した精製で化合物(A−3)(19g、42.54mmol、51.36%)を得た。
DMF(200mL)に溶解した化合物(A−3)(19g、42.54mmol)の溶液に、NBS(8.33g、46.80mmol)を添加した。周囲温度で10時間後、減圧下で有機溶媒を蒸留除去した。これに蒸留水を添加し、混合物を酢酸エチルで抽出した。この抽出物を硫酸マグネシウムで乾燥させ、減圧下で蒸留した。カラムを通した精製で化合物(A−4)(20g、38.06mmol、89.47%)を得た。
THF200mLに溶解した化合物(A−4)(20g、38.06mmol)の溶液に、n−buLi(15.22mL、38.06mmol、ヘキサン中2.5M)を−78℃でゆっくりと添加した。1時間攪拌した後で、これにホウ酸トリメチル(5.51mL、49.48mmol)を添加した。この混合物をゆっくりと周囲温度まで暖め、12時間攪拌した。蒸留水を添加し、混合物を酢酸エチルで抽出した。この抽出物を硫酸マグネシウムで乾燥させ、減圧下で蒸留した。カラムを通した精製で化合物(A−5)(8g、16.31mmol、42.86%)を得た。
化合物(A−5)(8g、16.31mmol)、ブロモ−2−ニトロベンゼン(3.95g、19.57mmol)、Pd(PPh3)4(0.56g、0.48mmol)、2MのK2CO3水溶液(16mL、32.62mmol)、トルエン(70mL)、およびエタノール(20mL)の混合物を還流下で攪拌した。化合物(A−1)の合成と同じ手順に従って、化合物(A−6)(7g、12.33mmol、75.62%)が得られた。
化合物(A−6)(7g、12.33mmol)がトリエチルホスファイト(100mL)と混合され、化合物(A−2)の合成と同じ手順が行われて、化合物(A−7)(4g、7.46mmol、58.33%)を得た。
化合物(A−7)(4g、7.46mmol)、ヨードベンゼン(1.25mL、11.20mmol)、銅粉体(0.17g、11.20mmol)、K2CO3(3.09g)、18−クラウン−6(0.15g、1.59mmol)および1,2−ジクロロベンゼン(100mL)の混合物を還流下で15時間攪拌した。この反応混合物を周囲温度まで冷却した後で、減圧下で有機溶媒を蒸留除去した。これに蒸留水を添加し、混合物を酢酸エチルで抽出した。この抽出物をカラムを通して精製して、化合物(A)(3.6g、5.88mmol、78.88%)を得た。
1,4−ジブロモ−2,3−ジニトロベンゼン(20g、61.36mmol)、1−ナフタレンボロン酸(26g、153.42mmol)、Pd(PPh3)4(3.54g、3.06mmol)、2MのK2CO3水溶液(90mL)、トルエン(200mL)およびエタノール(100mL)の混合物を還流下で10時間攪拌した。この反応混合物を周囲温度まで冷却した後で、これに蒸留水を添加し、得られた混合物を酢酸エチルで抽出した。この抽出物を硫酸マグネシウムで乾燥させ、減圧下で蒸留した。カラムを通した精製で化合物(B−1)(22g、52.32mmol、85.28%)を得た。
化合物(B−1)(22g、52.32mmol)およびトリエチルホスファイト(200mL)を混合して180℃で攪拌した。化合物(A−2)の合成と同じ手順に従って、化合物(B−2)(10g、28.05mmol、53.95%)を得た。
化合物(B−2)(10g、28.05mmol)、2−ヨードナフタレン(7.1g、28.05mmol)、銅粉体(2.67g、42.08mmol)、K2CO3(11.63g、84.17mmol)、18−クラウン−6(0.59g、2.24mmol)および1,2−ジクロロベンゼン(100mL)の混合物を190℃で20時間攪拌した。周囲温度まで冷却した後で、減圧下で有機溶媒を蒸留除去した。これに蒸留水を添加し、この混合物を酢酸エチルで抽出した。この抽出物を硫酸マグネシウムで乾燥させ、減圧下で蒸留した。カラムを通した精製で化合物(B−3)(4g、8.28mmol、29.60%)を得た。
DMF(20mL)中に溶解されたNaH(0.49g、12.43mmol、鉱物油中60%分散物)を収容する反応容器に、DMF(20mL)中に溶解された化合物(B−3)(4g、8.28mmol)の溶液を添加した。1時間後、これに、DMF(20mL)中に溶解された2−クロロ−4,6−ジフェニルトリアジン(2.66g、9.94mmol)の溶液を添加した。12時間の攪拌後、蒸留水を添加し、生じた固体を減圧下で濾別した。酢酸エチルおよびDMFからの再結晶化によって化合物(B)(3.5g、4.90mmol、59.21%)を得た。
エタノール(1000mL)中に溶解した1,2−シクロヘキシルジオン(42.52g、379.26mmol)の溶液に、2−ナフチルヒドラジン(20g、126.42mmol)をゆっくりと添加した。これに酢酸(0.28mL、5.05mmol)を添加し、この混合物を40℃に加熱した。2時間後、この混合物を冷却し、これに蒸留水を添加した。生じた固体は減圧下で濾別されて、化合物(C−1)(17g、67.37mmol、53.47%)を得た。
酢酸(100mL)中に溶解した化合物(C−1)(17g、67.37mmol)に、トリフルオロ酢酸(10mL)を添加した。周囲温度で2時間攪拌後、これに蒸留水を添加した。この混合物をNaOH水溶液で中和し、酢酸エチルで抽出した。この抽出物を硫酸マグネシウムで乾燥させ、減圧下で蒸留した。カラムを通した精製で化合物(C−2)(11g、46.75mmol、69.39%)を得た。
化合物(B−3)の合成と同じ手順に従って、化合物(C−3)(10g、32.11mmol、68.69%)を得た。
化合物(C−1)の合成と同じ手順に従って、化合物(C−4)(12g、29.88mmol、93.07%)を得た。
化合物(C−2)の合成と同じ手順に従って、化合物(C−5)(6g、15.68mmol、52.50%)を得た。
化合物(B)の合成と同じ手順に従って、化合物(C)(5g、8.14mmol、51.95%)を得た。
化合物(A−1)の合成と同じ手順に従うが化合物(D−1)を用いて、化合物(D−2)(11g、38.02mmol、89.22%)を得た。
化合物(A−2)の合成と同じ手順に従って、化合物(D−3)(8g、31.09mmol、81.78%)を得た。
化合物(B)の合成と同じ手順に従って、化合物(D)(6g、12.30mmol、38.70%)を得た。
化合物(A−1)の合成と同じ手順に従うが化合物(E−1)を用いて、化合物(E−2)(15g、51.85mmol、86.51%)を得た。
化合物(A−2)の合成と同じ手順に従って、化合物(E−3)(6g、23.31mmol、44.97%)を得た。
化合物(B)の合成と同じ手順に従って、化合物(E)(5g、10.25mmol、43.99%)を得た。
化合物(A−2)の合成と同じ手順に従って、化合物(F−1)(3g、11.65mmol、22.48%)を得た。
化合物(B)の合成と同じ手順に従って、化合物(F)(3g、6.15mmol、52.81%)を得た。
カルバゾール(20g、119.6mmol)、ヨードベンゼン(20mL、179.41mmol)、銅(11.4g、179.41mmol)、K2CO3(49g、358.8mmol)、18−クラウン−6(2.5g、9.56mmol)および1,2−ジクロロベンゼンの混合物を190℃で12時間攪拌した。周囲温度まで冷却した後で、この反応混合物を減圧下で蒸留した。これに蒸留水を添加し、得られた混合物を酢酸エチルで抽出した。この抽出物を硫酸マグネシウムで乾燥させ、減圧下で蒸留した。カラムを通して精製して、化合物(G−1)(22g、90.42mmol、75.60%)を得た。
化合物(A−4)の合成と同じ手順に従って、化合物(G−2)(25g、77.59mmol、85.81%)を得た。
化合物(A−5)の合成と同じ手順に従って、化合物(G−3)(11g、38.31mmol、49.37%)を得た。
化合物(A−1)の合成と同じ手順に従って、化合物(G−4)(12g、32.84mmol、85.72%)を得た。
化合物(A−2)の合成と同じ手順に従って、反応が4時間行われて、化合物(G−5)(6g、17.99mmol、54.80%)を得た。
化合物(B)の合成と同じ手順に従って、化合物(G)(7g、12.39mmol、68.91%)を得た。
化合物(A−2)の合成と同じ手順に従って、反応が4時間行われて化合物(H−1)(2g、5.99mmol、18.26%)を得た。
化合物(B)の合成と同じ手順に従って、化合物(H)(1.7g、3.01mmol、50.26%)を得た。
本発明の有機電界発光化合物を使用したOLEDの製造
本発明の電界発光化合物を使用することによりOLED素子が製造された。
まず、OLED用ガラス(サムスン−コーニングにより製造)から調製された透明電極ITO薄膜(15Ω/□)を、トリクロロエチレン、アセトン、エタノールおよび蒸留水を順に使用した超音波洗浄にかけ、イソプロパノール中に貯蔵し、その後使用した。
次に、真空蒸着装置の基体ホルダにITO基体を取り付け、この真空蒸着装置のセル内に4,4’,4”−トリス(N,N−(2−ナフチル)−フェニルアミノ)トリフェニルアミン(2−TNATA)(この化学構造は以下に示される)を入れ、次いでチャンバー内を10−6torrの真空に至るまで通気させた。セルに電流を適用して、2−TNATAを蒸発させ、それによりITO基体上に60nmの厚みを有する正孔注入層の蒸着物を生じさせた。
本発明の電界発光化合物を使用することによるOLEDの製造
実施例1〜10のOLEDについてのと同じ手順に従うが、ホスト材料として本発明の化合物(例えば、化合物TA4−H4−H4)を使用し、かつ電界発光ドーパントとして以下の化学式で表される有機イリジウム錯体(Ir(ppy)3)を使用して、OLEDが製造された。
OLEDを製造するために使用されたそれぞれ材料は10−6torrでの真空昇華によって精製された後で電界発光材料として使用された。
従来の電界発光材料を使用することによるOLEDの製造
実施例1および11に記載されるのと同じ手順に従うが、真空蒸着装置の他方のセルに、ホスト材料として本発明の電界発光化合物の代わりに、ビス(2−メチル−8−キノリナト)(p−フェニルフェノラト)アルミニウム(III)(BAlq)を入れて、OLEDが製造された。
Claims (8)
- 下記化学式5で表される有機電界発光化合物:
Z1〜Z8は独立してC(Ar3)およびNから選択され、Ar3は互いに異なっていてもよく、並びに隣り合うAr3基は一緒に結合して環を形成していてもよく;
Ar1は(C6−C60)アリールおよび(C3−C60)ヘテロアリールから選択され;
Ar3は独立して水素、(C1−C60)アルキル、ハロゲン、シアノ、(C3−C60)シクロアルキル、N、O、S、SiおよびPから選択される1以上のヘテロ原子を含む5員もしくは6員のヘテロシクロアルキル、(C7−C60)ビシクロアルキル、アダマンチル、(C2−C60)アルケニル、(C2−C60)アルキニル、(C6−C60)アリール、(C1−C60)アルコキシ、(C1−C60)アルキルチオ、トリ(C1−C30)アルキルシリル、ジ(C1−C30)アルキル(C6−C30)アリールシリル、トリ(C6−C30)アリールシリル、モノもしくはジ(C6−C30)アリールボラニル、モノもしくはジ(C1−C60)アルキルボラニル、ニトロおよびヒドロキシルから選択され;並びに
Ar1およびAr3のアルキル、シクロアルキル、ヘテロシクロアルキル、ビシクロアルキル、アダマンチル、アルケニル、アルキニル、アリール、アルコキシ、ヘテロアリール、アルキルチオ、トリアルキルシリル、ジアルキルアリールシリル、トリアリールシリル、アリールボラニルもしくはアルキルボラニルは、(C1−C60)アルキル、ハロゲン、シアノ、(C3−C60)シクロアルキル、N、O、S、SiおよびPから選択される1以上のヘテロ原子を含む5員もしくは6員のヘテロシクロアルキル、(C7−C60)ビシクロアルキル、アダマンチル、(C2−C60)アルケニル、(C2−C60)アルキニル、(C6−C60)アリール、(C1−C60)アルコキシ、(C6−C60)アリールオキシ、P(=O)RaRbで置換された(C6−C60)アリール[RaおよびRbは独立して(C1−C60)アルキルもしくは(C6−C60)アリールを表す]、(C3−C12)ヘテロアリール、(C6−C60)アリールで置換された(C3−C60)ヘテロアリール、(C1−C60)アルキルで置換された(C3−C60)ヘテロアリール、(C6−C60)アリール(C1−C60)アルキル、(C6−C60)アリールチオ、(C1−C60)アルキルチオ、モノもしくはジ(C1−C30)アルキルアミノ、モノもしくはジ(C6−C30)アリールアミノ、トリ(C1−C30)アルキルシリル、ジ(C1−C30)アルキル(C6−C30)アリールシリル、トリ(C6−C30)アリールシリル、モノもしくはジ(C6−C30)アリールボラニル、モノもしくはジ(C1−C60)アルキルボラニル、ニトロおよびヒドロキシルからなる群から選択される1種以上の置換基によってさらに置換されていてよく、
ただし、XおよびYの双方がN(Ar1)であり、かつZ1〜Z8の全てがC(Ar3)である場合を除き、並びに、
有機電界発光化合物が下記の化合物である場合を除く:
(下記式中のRおよR’は、R及びR’のいずれもがプロピル基、ブチル基もしくはベンジル基であるか又は、Rがプロピル基でありかつR’がブチル基である。)。
- 請求項1又は2に記載の有機電界発光化合物を含む有機電界発光素子。
- 第1の電極;第2の電極;並びに、第1の電極と第2の電極との間に設けられた1以上の有機層;を含む有機電界発光素子であって、前記有機層が請求項1又は2に記載の有機電界発光化合物の1種以上と、1種以上のリン光ドーパントとを含む、請求項3に記載の有機電界発光素子。
- 有機層が、アリールアミン化合物およびスチリルアリールアミン化合物からなる群から選択される1種以上のアミン化合物をさらに含む、請求項4に記載の有機電界発光素子。
- 有機層が、第1族、第2族、第4周期および第5周期遷移金属、ランタニド金属並びにd−遷移元素、またはこれらから形成される複合体の有機金属からなる群から選択される1種以上の金属をさらに含む、請求項4に記載の有機電界発光素子。
- 有機層が電界発光層および電荷発生層を含む、請求項4に記載の有機電界発光素子。
- 有機電界発光素子が白色光を発光する有機電界発光素子であり、有機層が青色、赤色もしくは緑色の光を発光する1以上の有機電界発光層を同時に含む、請求項4に記載の有機電界発光素子。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20090023944A KR101511072B1 (ko) | 2009-03-20 | 2009-03-20 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자 |
KR10-2009-0023944 | 2009-03-20 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012500717A Division JP2012520872A (ja) | 2009-03-20 | 2010-03-17 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016001749A true JP2016001749A (ja) | 2016-01-07 |
JP6153976B2 JP6153976B2 (ja) | 2017-06-28 |
Family
ID=42740124
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012500717A Pending JP2012520872A (ja) | 2009-03-20 | 2010-03-17 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
JP2015000550A Active JP6073933B2 (ja) | 2009-03-20 | 2015-01-05 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
JP2015000551A Active JP6114763B2 (ja) | 2009-03-20 | 2015-01-05 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
JP2015160532A Active JP6153976B2 (ja) | 2009-03-20 | 2015-08-17 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
JP2016139598A Active JP6356183B2 (ja) | 2009-03-20 | 2016-07-14 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012500717A Pending JP2012520872A (ja) | 2009-03-20 | 2010-03-17 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
JP2015000550A Active JP6073933B2 (ja) | 2009-03-20 | 2015-01-05 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
JP2015000551A Active JP6114763B2 (ja) | 2009-03-20 | 2015-01-05 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016139598A Active JP6356183B2 (ja) | 2009-03-20 | 2016-07-14 | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 |
Country Status (5)
Country | Link |
---|---|
JP (5) | JP2012520872A (ja) |
KR (1) | KR101511072B1 (ja) |
CN (9) | CN105176523B (ja) |
TW (2) | TW201105768A (ja) |
WO (1) | WO2010107244A2 (ja) |
Families Citing this family (207)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102103062B1 (ko) | 2006-02-10 | 2020-04-22 | 유니버셜 디스플레이 코포레이션 | 시클로금속화 이미다조[1,2-f]페난트리딘 및 디이미다조[1,2-a:1',2'-c]퀴나졸린 리간드, 및 이의 등전자성 및 벤즈고리화된 유사체의 금속 착체 |
WO2010131855A2 (ko) | 2009-05-13 | 2010-11-18 | 덕산하이메탈(주) | 오원자 헤테로고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
WO2009148016A1 (ja) * | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | ハロゲン化合物、多環系化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
US8049411B2 (en) | 2008-06-05 | 2011-11-01 | Idemitsu Kosan Co., Ltd. | Material for organic electroluminescence device and organic electroluminescence device using the same |
EP2796448B1 (en) * | 2008-08-22 | 2018-04-25 | Lg Chem, Ltd. | Material for organic electronic device and organic electronic device using the same |
KR101511072B1 (ko) * | 2009-03-20 | 2015-04-10 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자 |
KR101477613B1 (ko) * | 2009-03-31 | 2014-12-30 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전자 소자 |
US10020452B2 (en) * | 2011-12-15 | 2018-07-10 | Samsung Mobile Display Co., Ltd. | Compound containing a 5-membered heterocycle and organic light-emitting diode using same, and terminal for same |
DE102009023155A1 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
KR101108154B1 (ko) * | 2009-08-10 | 2012-02-08 | 삼성모바일디스플레이주식회사 | 축합환 화합물 및 이를 포함한 유기층을 구비한 유기 발광 소자 |
KR101193182B1 (ko) * | 2009-09-02 | 2012-10-19 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US8288187B2 (en) | 2010-01-20 | 2012-10-16 | Universal Display Corporation | Electroluminescent devices for lighting applications |
JP5931051B2 (ja) * | 2010-04-06 | 2016-06-08 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 置換カルバゾール誘導体および有機エレクトロニクスにおけるその使用 |
KR101531904B1 (ko) * | 2010-10-13 | 2015-06-29 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20120052879A (ko) * | 2010-11-16 | 2012-05-24 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
EP2644607A4 (en) * | 2010-11-22 | 2014-05-28 | Idemitsu Kosan Co | OXYGENIC FUSIONED RING DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT THEREWITH |
JP5699581B2 (ja) * | 2010-12-15 | 2015-04-15 | Jnc株式会社 | 縮合ピロール多環化合物、発光層用材料およびこれを用いた有機電界発光素子 |
JP2012140367A (ja) * | 2010-12-28 | 2012-07-26 | Idemitsu Kosan Co Ltd | 縮合多環化合物、有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子 |
JP5756288B2 (ja) * | 2010-12-28 | 2015-07-29 | 出光興産株式会社 | 縮合多環化合物、有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子 |
US9543526B2 (en) | 2011-03-16 | 2017-01-10 | Nippon Steel & Sumikin Chemical Co., Ltd. | Nitrogen-containing aromatic compounds and organic electroluminescent device |
US9373793B2 (en) * | 2011-06-27 | 2016-06-21 | Lg Chem, Ltd. | Compound and organic light-emitting device using same |
JP5938175B2 (ja) * | 2011-07-15 | 2016-06-22 | 出光興産株式会社 | 含窒素芳香族複素環誘導体およびそれを用いた有機エレクトロルミネッセンス素子 |
KR20130011405A (ko) * | 2011-07-21 | 2013-01-30 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
KR101887003B1 (ko) * | 2011-07-21 | 2018-08-13 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
DE112012006817B3 (de) | 2011-07-22 | 2020-06-10 | Semiconductor Energy Laboratory Co., Ltd. | Verfahren zur Synthese einer Dibenzo[c,g]carbazol-Verbindung. |
US20140217393A1 (en) * | 2011-09-09 | 2014-08-07 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
CA2849087A1 (en) * | 2011-09-21 | 2013-03-28 | Merck Patent Gmbh | Carbazole derivatives for organic electroluminescent devices |
KR101380335B1 (ko) | 2011-10-10 | 2014-04-10 | 삼성디스플레이 주식회사 | 헤테로시클릭 화합물, 이를 포함하는 유기 발광 소자 및 평판 표시 장치 |
KR101971198B1 (ko) | 2011-10-19 | 2019-04-23 | 삼성디스플레이 주식회사 | 헤테로시클릭 화합물, 이를 포함하는 유기 발광 소자 및 평판 표시 장치 |
KR101903216B1 (ko) | 2011-10-20 | 2018-10-01 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 재료 |
WO2013081315A1 (ko) * | 2011-11-28 | 2013-06-06 | 덕산하이메탈(주) | 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
KR101497124B1 (ko) | 2011-11-28 | 2015-03-06 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
KR101497123B1 (ko) * | 2011-12-30 | 2015-03-09 | 덕산네오룩스 주식회사 | 오원자 헤테로 고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
KR102012047B1 (ko) | 2012-01-06 | 2019-08-19 | 유니버셜 디스플레이 코포레이션 | 효율이 큰 인광 물질 |
KR102054229B1 (ko) * | 2012-01-13 | 2019-12-11 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
US9386657B2 (en) | 2012-03-15 | 2016-07-05 | Universal Display Corporation | Organic Electroluminescent materials and devices |
KR101973166B1 (ko) * | 2012-03-27 | 2019-04-29 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함하는 유기 발광 표시 장치 |
KR101390616B1 (ko) * | 2012-03-28 | 2014-04-29 | 주식회사 두산 | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20130114785A (ko) * | 2012-04-10 | 2013-10-21 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101447959B1 (ko) * | 2012-05-25 | 2014-10-13 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
KR102025834B1 (ko) * | 2012-06-29 | 2019-09-27 | 삼성디스플레이 주식회사 | 신규한 유기 발광 화합물 및 이를 포함한 유기 발광 소자 |
US9540329B2 (en) | 2012-07-19 | 2017-01-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102086544B1 (ko) | 2012-07-31 | 2020-03-10 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
WO2014025114A1 (ko) * | 2012-08-10 | 2014-02-13 | 주식회사 두산 | 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR101742403B1 (ko) * | 2012-08-10 | 2017-05-31 | 주식회사 두산 | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR101452579B1 (ko) | 2012-08-17 | 2014-10-21 | 주식회사 두산 | 신규 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102082532B1 (ko) * | 2012-08-20 | 2020-02-27 | 마낙 가부시끼가이샤 | 보린산 유도체의 제조 방법 및 신규 보린산 유도체 |
EP2890221A4 (en) * | 2012-08-24 | 2016-09-14 | Konica Minolta Inc | TRANSPARENT ELECTRODE, ELECTRONIC DEVICE AND METHOD FOR PRODUCING THE TRANSPARENT ELECTRODE |
JP5896863B2 (ja) | 2012-08-27 | 2016-03-30 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料 |
KR102023028B1 (ko) * | 2012-09-14 | 2019-09-23 | 삼성디스플레이 주식회사 | 포스핀 옥사이드계 화합물 및 이를 포함한 유기 발광 소자 |
US9252363B2 (en) | 2012-10-04 | 2016-02-02 | Universal Display Corporation | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
KR101438080B1 (ko) * | 2012-11-22 | 2014-09-11 | (주)피엔에이치테크 | 새로운 유기전계발광소자용 화합물 및 그를 포함하는 유기전계발광소자 |
US9166175B2 (en) * | 2012-11-27 | 2015-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN104797571A (zh) * | 2012-12-04 | 2015-07-22 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物和包含所述化合物的有机电致发光装置 |
US9196860B2 (en) | 2012-12-04 | 2015-11-24 | Universal Display Corporation | Compounds for triplet-triplet annihilation upconversion |
US8716484B1 (en) | 2012-12-05 | 2014-05-06 | Universal Display Corporation | Hole transporting materials with twisted aryl groups |
US9653691B2 (en) | 2012-12-12 | 2017-05-16 | Universal Display Corporation | Phosphorescence-sensitizing fluorescence material system |
EP2941469A2 (de) * | 2013-01-03 | 2015-11-11 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
KR101556822B1 (ko) * | 2013-02-25 | 2015-10-01 | 주식회사 두산 | 유기 전계 발광 소자 |
KR102050484B1 (ko) | 2013-03-04 | 2019-12-02 | 삼성디스플레이 주식회사 | 안트라센 유도체 및 이를 포함하는 유기전계발광소자 |
KR102167038B1 (ko) | 2013-03-27 | 2020-10-19 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
WO2014156342A1 (ja) * | 2013-03-28 | 2014-10-02 | 新日鉄住金化学株式会社 | 有機トランジスタ用有機半導体材料及び有機トランジスタ素子 |
KR102107106B1 (ko) | 2013-05-09 | 2020-05-07 | 삼성디스플레이 주식회사 | 스티릴계 화합물 및 이를 포함한 유기 발광 소자 |
KR102304715B1 (ko) | 2013-06-14 | 2021-09-27 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US20160155955A1 (en) * | 2013-06-14 | 2016-06-02 | Hodogaya Chemical Co., Ltd. | Dicarbazole derivatives and organic electroluminescent devices |
KR102269131B1 (ko) | 2013-07-01 | 2021-06-25 | 삼성디스플레이 주식회사 | 화합물 및 이를 포함한 유기 발광 소자 |
WO2015005351A1 (ja) * | 2013-07-09 | 2015-01-15 | 東ソー株式会社 | アダマンチル基を有する環状アジン化合物、製造方法、及びそれを構成成分とする有機電界発光素子 |
US10074806B2 (en) | 2013-08-20 | 2018-09-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US9831437B2 (en) | 2013-08-20 | 2017-11-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102158000B1 (ko) * | 2013-09-26 | 2020-09-22 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
US9876173B2 (en) | 2013-12-09 | 2018-01-23 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN103936749B (zh) * | 2013-12-12 | 2016-06-22 | 石家庄诚志永华显示材料有限公司 | 含有杂原子桥联咔唑结构单元的化合物及其制备方法与应用 |
US10062850B2 (en) | 2013-12-12 | 2018-08-28 | Samsung Display Co., Ltd. | Amine-based compounds and organic light-emitting devices comprising the same |
WO2015093878A1 (en) * | 2013-12-18 | 2015-06-25 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound, and multi-component host material and organic electroluminescent device comprising the same |
KR20150071624A (ko) * | 2013-12-18 | 2015-06-26 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR102214622B1 (ko) * | 2013-12-27 | 2021-02-15 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
WO2015099507A1 (en) * | 2013-12-27 | 2015-07-02 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compound, and multi-component host material and organic electroluminescent device comprising the same |
US10361377B2 (en) * | 2014-01-14 | 2019-07-23 | Samsung Sdi Co., Ltd. | Condensed cyclic compound and organic light emitting device including the same |
KR101802861B1 (ko) | 2014-02-14 | 2017-11-30 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US9450198B2 (en) | 2014-04-15 | 2016-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20150132795A (ko) | 2014-05-16 | 2015-11-26 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102253440B1 (ko) | 2014-06-02 | 2021-05-20 | 삼성디스플레이 주식회사 | 아민계 화합물 및 이를 포함한 유기 발광 소자 |
KR102327086B1 (ko) | 2014-06-11 | 2021-11-17 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
DE102014008722A1 (de) | 2014-06-18 | 2015-12-24 | Merck Patent Gmbh | Zusammensetzungen für elektronische Vorrichtungen |
KR20160010333A (ko) * | 2014-07-17 | 2016-01-27 | 롬엔드하스전자재료코리아유한회사 | 전자전달재료 및 이를 포함하는 유기 전계 발광 소자 |
WO2016010380A1 (en) | 2014-07-17 | 2016-01-21 | Rohm And Haas Electronic Materials Korea Ltd. | Electron transport material and organic electroluminescent device comprising the same |
KR102212972B1 (ko) * | 2014-07-21 | 2021-02-05 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2016024637A1 (ja) * | 2014-08-15 | 2016-02-18 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 |
KR102242791B1 (ko) * | 2014-08-29 | 2021-04-21 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR102331466B1 (ko) * | 2014-08-29 | 2021-12-01 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
KR102465590B1 (ko) * | 2014-12-08 | 2022-11-14 | 삼성디스플레이 주식회사 | 유기 발광 소자 및 이를 포함하는 표시 장치 |
KR102490882B1 (ko) | 2014-12-31 | 2023-01-25 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
CN105753629B (zh) * | 2015-01-07 | 2018-11-16 | 机光科技股份有限公司 | 化合物和使用其的有机电致发光装置 |
KR102343145B1 (ko) | 2015-01-12 | 2021-12-27 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
KR102338908B1 (ko) * | 2015-03-03 | 2021-12-14 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US11495749B2 (en) | 2015-04-06 | 2022-11-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11818949B2 (en) | 2015-04-06 | 2023-11-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20160293855A1 (en) | 2015-04-06 | 2016-10-06 | Universal Display Corporation | Organic Electroluminescent Materials and Devices |
US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672996B2 (en) | 2015-09-03 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102626916B1 (ko) * | 2015-09-09 | 2024-01-19 | 삼성전자주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR20170051762A (ko) * | 2015-10-30 | 2017-05-12 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102399570B1 (ko) | 2015-11-26 | 2022-05-19 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US11910707B2 (en) | 2015-12-23 | 2024-02-20 | Samsung Display Co., Ltd. | Organic light-emitting device |
KR102419178B1 (ko) | 2015-12-29 | 2022-07-11 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US20170229663A1 (en) | 2016-02-09 | 2017-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20170101128A (ko) | 2016-02-26 | 2017-09-05 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102479135B1 (ko) * | 2016-04-18 | 2022-12-21 | 롬엔드하스전자재료코리아유한회사 | 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자 |
WO2017183859A1 (en) | 2016-04-18 | 2017-10-26 | Rohm And Haas Electronic Materials Korea Ltd. | A plurality of host materials and organic electroluminescent device comprising the same |
KR102577653B1 (ko) * | 2016-04-29 | 2023-09-13 | 솔루스첨단소재 주식회사 | 유기 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20170127101A (ko) | 2016-05-10 | 2017-11-21 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR20170129599A (ko) * | 2016-05-17 | 2017-11-27 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물, 유기 전계 발광 재료, 및 이를 포함하는 유기 전계 발광 소자 |
KR102211337B1 (ko) * | 2016-05-19 | 2021-02-03 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
WO2017205425A1 (en) * | 2016-05-24 | 2017-11-30 | President And Fellows Of Harvard College | Compounds for organic light emitting diode materials |
KR101877678B1 (ko) * | 2016-06-09 | 2018-07-11 | 주식회사 엘지화학 | 화합물 및 이를 이용한 유기 발광 소자 |
US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10862054B2 (en) | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR101959047B1 (ko) * | 2016-07-15 | 2019-03-18 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
KR102435083B1 (ko) * | 2016-07-27 | 2022-08-24 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
KR20180017682A (ko) | 2016-08-10 | 2018-02-21 | 삼성전자주식회사 | 실릴계 화합물 및 이를 포함하는 유기 발광 소자 |
US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102529341B1 (ko) * | 2016-10-05 | 2023-05-09 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
US11283028B2 (en) * | 2016-10-05 | 2022-03-22 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN106565687B (zh) * | 2016-10-31 | 2019-05-07 | 中节能万润股份有限公司 | 一种新型oled材料、制备方法及其应用 |
US20180130956A1 (en) | 2016-11-09 | 2018-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102109545B1 (ko) | 2016-12-22 | 2020-05-12 | 삼성에스디아이 주식회사 | 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치 |
US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102582797B1 (ko) | 2017-01-10 | 2023-09-27 | 롬엔드하스전자재료코리아유한회사 | 유기 전계 발광 소자 |
US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102174388B1 (ko) * | 2017-05-12 | 2020-11-04 | 주식회사 엘지화학 | 고리 화합물 및 이를 포함하는 유기 발광 소자 |
US20180370999A1 (en) | 2017-06-23 | 2018-12-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR101895949B1 (ko) * | 2017-09-28 | 2018-09-06 | 덕산네오룩스 주식회사 | 오원자 헤테로 고리를 포함하는 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
US20190161504A1 (en) | 2017-11-28 | 2019-05-30 | University Of Southern California | Carbene compounds and organic electroluminescent devices |
EP3492480B1 (en) | 2017-11-29 | 2021-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102536247B1 (ko) | 2017-12-22 | 2023-05-25 | 삼성디스플레이 주식회사 | 헤테로고리 화합물 및 이를 포함한 유기 발광 소자 |
US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR102191157B1 (ko) * | 2018-03-06 | 2020-12-15 | 주식회사 엘지화학 | 다환 화합물 및 이를 포함하는 유기 발광 소자 |
JP7138466B2 (ja) * | 2018-04-09 | 2022-09-16 | 日本放送協会 | 有機エレクトロルミネッセンス素子、表示装置、照明装置 |
TWI660028B (zh) * | 2018-07-13 | 2019-05-21 | 祥德科技股份有限公司 | 用於有機發光元件的發光層主體材料 |
EP3604477A1 (en) | 2018-07-30 | 2020-02-05 | Idemitsu Kosan Co., Ltd. | Polycyclic compound, organic electroluminescence device, and electronic device |
US20200075870A1 (en) | 2018-08-22 | 2020-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN111072666A (zh) * | 2018-10-19 | 2020-04-28 | 北京鼎材科技有限公司 | 有机电致发光材料及其应用 |
US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US11834459B2 (en) | 2018-12-12 | 2023-12-05 | Universal Display Corporation | Host materials for electroluminescent devices |
US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
US20200251664A1 (en) | 2019-02-01 | 2020-08-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20200295291A1 (en) | 2019-03-12 | 2020-09-17 | Universal Display Corporation | OLED WITH TRIPLET EMITTER AND EXCITED STATE LIFETIME LESS THAN 200 ns |
JP2020158491A (ja) | 2019-03-26 | 2020-10-01 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
CN110028459B (zh) * | 2019-05-24 | 2023-04-18 | 武汉天马微电子有限公司 | 化合物、显示面板以及显示装置 |
CN110156756A (zh) * | 2019-05-27 | 2019-08-23 | 上海天马有机发光显示技术有限公司 | 化合物、显示面板以及显示装置 |
US20210032278A1 (en) | 2019-07-30 | 2021-02-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210047354A1 (en) | 2019-08-16 | 2021-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20210135130A1 (en) | 2019-11-04 | 2021-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP7488091B2 (ja) | 2019-11-14 | 2024-05-21 | ユニバーサル ディスプレイ コーポレイション | 有機エレクトロルミネセンス材料及びデバイス |
US20210217969A1 (en) | 2020-01-06 | 2021-07-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
KR20210111574A (ko) * | 2020-03-03 | 2021-09-13 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
CN112812119A (zh) * | 2020-05-20 | 2021-05-18 | 陕西莱特光电材料股份有限公司 | 一种有机化合物以及使用其的电子元件和装置 |
CN111689946A (zh) * | 2020-06-17 | 2020-09-22 | 深圳大学 | 一种咔唑并芳环热活化延迟荧光材料及其有机电致发光器件 |
EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
JP2023156534A (ja) * | 2020-08-07 | 2023-10-25 | 国立大学法人京都大学 | 化合物、発光材料および有機発光素子 |
US20220158096A1 (en) | 2020-11-16 | 2022-05-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN112480077B (zh) * | 2020-11-17 | 2022-04-12 | 上海和辉光电股份有限公司 | 一种用于有机发光的化合物及其应用 |
US20220162243A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220165967A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220271241A1 (en) | 2021-02-03 | 2022-08-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4060758A3 (en) | 2021-02-26 | 2023-03-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4059915A3 (en) | 2021-02-26 | 2022-12-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298192A1 (en) | 2021-03-05 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298190A1 (en) | 2021-03-12 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220298193A1 (en) | 2021-03-15 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220340607A1 (en) | 2021-04-05 | 2022-10-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
US20220352478A1 (en) | 2021-04-14 | 2022-11-03 | Universal Display Corporation | Organic eletroluminescent materials and devices |
US20230006149A1 (en) | 2021-04-23 | 2023-01-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20220407020A1 (en) | 2021-04-23 | 2022-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230133787A1 (en) | 2021-06-08 | 2023-05-04 | University Of Southern California | Molecular Alignment of Homoleptic Iridium Phosphors |
EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN118103376A (zh) | 2021-10-14 | 2024-05-28 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
EP4212539A1 (en) | 2021-12-16 | 2023-07-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230292592A1 (en) | 2022-03-09 | 2023-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230337516A1 (en) | 2022-04-18 | 2023-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20230389421A1 (en) | 2022-05-24 | 2023-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240016051A1 (en) | 2022-06-28 | 2024-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN117777137A (zh) * | 2022-09-22 | 2024-03-29 | 陕西莱特光电材料股份有限公司 | 有机化合物、有机电致发光器件及电子装置 |
US20240188419A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240180025A1 (en) | 2022-10-27 | 2024-05-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240196730A1 (en) | 2022-10-27 | 2024-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240188316A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
US20240188319A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
EP4386065A1 (en) | 2022-12-14 | 2024-06-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009148015A1 (ja) * | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | ハロゲン化合物、多環系化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2009148016A1 (ja) * | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | ハロゲン化合物、多環系化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2009148062A1 (ja) * | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | 多環系化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2507902B2 (ja) * | 1991-03-13 | 1996-06-19 | 工業技術院長 | 含硫黄有機系三次非線形光学材料 |
US5942340A (en) * | 1997-10-02 | 1999-08-24 | Xerox Corporation | Indolocarbazole electroluminescent devices |
JP3933591B2 (ja) * | 2002-03-26 | 2007-06-20 | 淳二 城戸 | 有機エレクトロルミネッセント素子 |
TWI314947B (en) * | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
JP4408382B2 (ja) * | 2004-03-18 | 2010-02-03 | 株式会社 日立ディスプレイズ | 有機発光表示装置 |
US7402681B2 (en) * | 2004-12-14 | 2008-07-22 | Xerox Corporation | Compound with indolocarbazole moieties and devices containing such compound |
JP5055689B2 (ja) * | 2004-08-26 | 2012-10-24 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置および表示装置 |
EP1805280B1 (en) * | 2004-09-20 | 2011-02-09 | LG Chem, Ltd. | Carbazole derivative and organic light emitting device using same |
JP4747558B2 (ja) * | 2004-11-08 | 2011-08-17 | ソニー株式会社 | 表示素子用有機材料および表示素子 |
US8334058B2 (en) * | 2005-04-14 | 2012-12-18 | Merck Patent Gmbh | Compounds for organic electronic devices |
DE102005023437A1 (de) * | 2005-05-20 | 2006-11-30 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
JP2006339577A (ja) * | 2005-06-06 | 2006-12-14 | Konica Minolta Holdings Inc | 有機半導体薄膜及び有機薄膜トランジスタ |
JP2006351638A (ja) * | 2005-06-13 | 2006-12-28 | Fujifilm Holdings Corp | 発光素子 |
KR101404299B1 (ko) * | 2005-09-08 | 2014-06-05 | 도레이 카부시키가이샤 | 발광 소자 재료 및 발광 소자 |
WO2007063796A1 (ja) * | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | 有機電界発光素子 |
EP1956022B1 (en) * | 2005-12-01 | 2012-07-25 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent element and organic electroluminescent element |
JP5157079B2 (ja) * | 2006-04-19 | 2013-03-06 | コニカミノルタホールディングス株式会社 | 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ |
DE102006025846A1 (de) * | 2006-06-02 | 2007-12-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102006031990A1 (de) * | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
JP5272345B2 (ja) * | 2006-08-28 | 2013-08-28 | 東ソー株式会社 | ヘテロアセン誘導体、テトラハロターフェニル誘導体及びそれらの製造方法 |
WO2008026602A1 (fr) * | 2006-08-28 | 2008-03-06 | Tosoh Corporation | Dérivé hétéroacène, dérivé tétrahalotérphényle, et leurs procédés de production |
CN101511834B (zh) * | 2006-11-09 | 2013-03-27 | 新日铁化学株式会社 | 有机场致发光元件用化合物及有机场致发光元件 |
JP5160078B2 (ja) * | 2006-12-06 | 2013-03-13 | 国立大学法人広島大学 | 電界効果トランジスタ |
WO2008132103A1 (de) * | 2007-04-26 | 2008-11-06 | Basf Se | Pentaphenylenderivate als photosensibilisatoren in solarzellen |
TWI468489B (zh) * | 2007-05-29 | 2015-01-11 | Nippon Steel & Sumikin Chem Co | Organic electroluminescent element compounds and organic electroluminescent elements |
EP2169029A4 (en) * | 2007-05-30 | 2013-05-29 | Nippon Steel & Sumikin Chem Co | COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE AND ORGANIC ELECTROLUMINESCENCE DEVICE |
JP2009009965A (ja) * | 2007-06-26 | 2009-01-15 | Mitsui Chemicals Inc | 有機トランジスタ |
CN100548984C (zh) * | 2007-11-26 | 2009-10-14 | 山东大学 | 一种吲哚[3,2-b]咔唑衍生物类有机电致发光材料 |
JP2009203183A (ja) * | 2008-02-27 | 2009-09-10 | Tosoh Corp | ヘテロアセン誘導体の製造方法 |
JP5200099B2 (ja) * | 2008-05-08 | 2013-05-15 | 新日鉄住金化学株式会社 | 有機電界発光素子用化合物及び有機電界発光素子 |
CN102017220B (zh) * | 2008-05-08 | 2012-11-07 | 新日铁化学株式会社 | 有机场致发光元件用化合物及有机场致发光元件 |
JP5493309B2 (ja) * | 2008-08-18 | 2014-05-14 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
US9169206B2 (en) * | 2008-12-23 | 2015-10-27 | Luminano Co., Ltd. | Organic semiconductor compound, method for preparing the same, and organic semiconductor composition, and organic semiconductor thin film and element containing the same |
KR101511072B1 (ko) * | 2009-03-20 | 2015-04-10 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자 |
DE102009051172A1 (de) * | 2009-10-29 | 2011-05-05 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
-
2009
- 2009-03-20 KR KR20090023944A patent/KR101511072B1/ko active IP Right Grant
-
2010
- 2010-03-17 CN CN201510586398.6A patent/CN105176523B/zh active Active
- 2010-03-17 CN CN201310560064.2A patent/CN103524510B/zh active Active
- 2010-03-17 JP JP2012500717A patent/JP2012520872A/ja active Pending
- 2010-03-17 WO PCT/KR2010/001647 patent/WO2010107244A2/en active Application Filing
- 2010-03-17 CN CN201310560173.4A patent/CN103641832A/zh active Pending
- 2010-03-17 CN CN201310559971.5A patent/CN103641831A/zh active Pending
- 2010-03-17 CN CN201310560948.8A patent/CN103555322B/zh active Active
- 2010-03-17 CN CN201310559945.2A patent/CN103641830B/zh active Active
- 2010-03-17 CN CN2010800224996A patent/CN102482571A/zh active Pending
- 2010-03-17 CN CN201510340976.8A patent/CN105001224A/zh active Pending
- 2010-03-17 CN CN201510847414.2A patent/CN105294712A/zh active Pending
- 2010-03-18 TW TW099107944A patent/TW201105768A/zh unknown
- 2010-03-18 TW TW104106210A patent/TW201522570A/zh unknown
-
2015
- 2015-01-05 JP JP2015000550A patent/JP6073933B2/ja active Active
- 2015-01-05 JP JP2015000551A patent/JP6114763B2/ja active Active
- 2015-08-17 JP JP2015160532A patent/JP6153976B2/ja active Active
-
2016
- 2016-07-14 JP JP2016139598A patent/JP6356183B2/ja active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2009148015A1 (ja) * | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | ハロゲン化合物、多環系化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2009148016A1 (ja) * | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | ハロゲン化合物、多環系化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2009148062A1 (ja) * | 2008-06-05 | 2009-12-10 | 出光興産株式会社 | 多環系化合物及びそれを用いた有機エレクトロルミネッセンス素子 |
Also Published As
Publication number | Publication date |
---|---|
WO2010107244A3 (en) | 2010-12-09 |
CN103641831A (zh) | 2014-03-19 |
JP6073933B2 (ja) | 2017-02-01 |
CN103641832A (zh) | 2014-03-19 |
CN103555322A (zh) | 2014-02-05 |
WO2010107244A2 (en) | 2010-09-23 |
JP2015122508A (ja) | 2015-07-02 |
JP6114763B2 (ja) | 2017-04-12 |
KR20100105099A (ko) | 2010-09-29 |
CN103641830A (zh) | 2014-03-19 |
CN105294712A (zh) | 2016-02-03 |
TW201522570A (zh) | 2015-06-16 |
CN102482571A (zh) | 2012-05-30 |
CN103641830B (zh) | 2017-04-12 |
CN105176523A (zh) | 2015-12-23 |
CN103524510B (zh) | 2016-02-10 |
CN105176523B (zh) | 2017-10-10 |
JP2015120702A (ja) | 2015-07-02 |
JP6356183B2 (ja) | 2018-07-11 |
TW201105768A (en) | 2011-02-16 |
CN105001224A (zh) | 2015-10-28 |
KR101511072B1 (ko) | 2015-04-10 |
JP2017008061A (ja) | 2017-01-12 |
JP2012520872A (ja) | 2012-09-10 |
CN103524510A (zh) | 2014-01-22 |
CN103555322B (zh) | 2016-08-17 |
JP6153976B2 (ja) | 2017-06-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6356183B2 (ja) | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 | |
KR101313730B1 (ko) | 유기 전계 발광 소자 | |
KR100974562B1 (ko) | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기 발광 소자 | |
KR100910153B1 (ko) | 신규한 적색 인광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자 | |
KR20110049217A (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
JP2013526014A (ja) | 新規有機電界発光化合物およびこれを使用する有機電界発光素子 | |
JPWO2010113755A1 (ja) | 燐光発光素子用材料及びこれを用いた有機電界発光素子 | |
KR20100106014A (ko) | 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계발광 소자 | |
KR20120116282A (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
KR20110008723A (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
JP2013546171A (ja) | 有機電子材料のための新規化合物、およびこれを使用する有機電界発光素子 | |
JP5591464B2 (ja) | 新規な赤色エレクトロルミネセント化合物及びこれを使用する有機エレクトロルミネセントデバイス | |
KR20110116618A (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
JP2009149607A (ja) | 新規な有機エレクトロルミネセント化合物及びこれを使用する有機エレクトロルミネセントデバイス | |
KR20140072295A (ko) | 중수소 치환된 유기금속 착물 및 이를 포함하는 유기 발광 소자 | |
JP7422430B2 (ja) | ヘテロ環化合物及びこれを含む有機発光素子 | |
JP2009170883A (ja) | 電気発光用の有機金属化合物及びこれを使用する有機電気発光素子 | |
KR101778046B1 (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
JP2023503108A (ja) | 化合物及び当該化合物を含有する有機エレクトロルミネッセンス素子 | |
KR101682893B1 (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
KR101650294B1 (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
KR101552477B1 (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
KR20140130637A (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
KR20140023406A (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
KR20140053056A (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20160707 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160830 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20161118 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20170508 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170531 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6153976 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |