KR100884437B1 - 전자발광 디바이스용 유기 소자 - Google Patents
전자발광 디바이스용 유기 소자 Download PDFInfo
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- KR100884437B1 KR100884437B1 KR1020030012801A KR20030012801A KR100884437B1 KR 100884437 B1 KR100884437 B1 KR 100884437B1 KR 1020030012801 A KR1020030012801 A KR 1020030012801A KR 20030012801 A KR20030012801 A KR 20030012801A KR 100884437 B1 KR100884437 B1 KR 100884437B1
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- dopant
- substituents
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- 239000002019 doping agent Substances 0.000 claims abstract description 62
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 150000001639 boron compounds Chemical class 0.000 claims abstract description 12
- 239000003446 ligand Substances 0.000 claims abstract description 9
- -1 anthracene compound Chemical class 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 229910052796 boron Inorganic materials 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 239000010410 layer Substances 0.000 description 114
- 239000000463 material Substances 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000004020 luminiscence type Methods 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 230000032258 transport Effects 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 18
- 229910052715 tantalum Inorganic materials 0.000 description 17
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000000151 deposition Methods 0.000 description 14
- 230000008021 deposition Effects 0.000 description 14
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 125000005259 triarylamine group Chemical group 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 238000005401 electroluminescence Methods 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000013112 stability test Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001638 boron Chemical class 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 6
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 125000000732 arylene group Chemical group 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000007773 negative electrode material Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 229930192334 Auxin Natural products 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002363 auxin Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
- 230000006798 recombination Effects 0.000 description 4
- 238000005215 recombination Methods 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- LQRAULANJCQXAM-UHFFFAOYSA-N 1-n,5-n-dinaphthalen-1-yl-1-n,5-n-diphenylnaphthalene-1,5-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC(=C2C=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC2=CC=CC=C12 LQRAULANJCQXAM-UHFFFAOYSA-N 0.000 description 2
- KMQPLEYEXDZOJF-UHFFFAOYSA-N 1-naphthalen-2-ylanthracene Chemical compound C1=CC=C2C=C3C(C4=CC5=CC=CC=C5C=C4)=CC=CC3=CC2=C1 KMQPLEYEXDZOJF-UHFFFAOYSA-N 0.000 description 2
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 2
- OOHZFEFUGYMQMD-UHFFFAOYSA-N 2-pyridin-2-yl-1h-quinolin-2-amine Chemical compound N1C2=CC=CC=C2C=CC1(N)C1=CC=CC=N1 OOHZFEFUGYMQMD-UHFFFAOYSA-N 0.000 description 2
- VNHXBLBWQFQTTG-UHFFFAOYSA-N 4-phenylquinolin-2-amine Chemical compound C=12C=CC=CC2=NC(N)=CC=1C1=CC=CC=C1 VNHXBLBWQFQTTG-UHFFFAOYSA-N 0.000 description 2
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical class C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 0 Cc(cc1)cc(N(C)c(cc23)c4cc2N(C)*(cc(cc2)P)c2C3=O)c1C4=O Chemical compound Cc(cc1)cc(N(C)c(cc23)c4cc2N(C)*(cc(cc2)P)c2C3=O)c1C4=O 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 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 2
- 239000000975 dye Substances 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 2
- UHVLDCDWBKWDDN-UHFFFAOYSA-N n-phenyl-n-[4-[4-(n-pyren-2-ylanilino)phenyl]phenyl]pyren-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=CC3=CC=CC4=CC=C(C2=C43)C=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC4=CC=CC5=CC=C(C3=C54)C=2)C=C1 UHVLDCDWBKWDDN-UHFFFAOYSA-N 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001544 thienyl group Chemical group 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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 1
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- GNLSNQQRNOQFBK-UHFFFAOYSA-N n-[4-[4-[4-(dinaphthalen-2-ylamino)phenyl]phenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical group C1=CC=CC2=CC(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 GNLSNQQRNOQFBK-UHFFFAOYSA-N 0.000 description 1
- NBHXGUASDDSHGV-UHFFFAOYSA-N n-[4-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 NBHXGUASDDSHGV-UHFFFAOYSA-N 0.000 description 1
- RJSTZCQRFUSBJV-UHFFFAOYSA-N n-[4-[4-[n-(1,2-dihydroacenaphthylen-3-yl)anilino]phenyl]phenyl]-n-phenyl-1,2-dihydroacenaphthylen-3-amine Chemical group C1=CC(C2=3)=CC=CC=3CCC2=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=2CCC3=CC=CC(C=23)=CC=1)C1=CC=CC=C1 RJSTZCQRFUSBJV-UHFFFAOYSA-N 0.000 description 1
- MEYJVORNUBJAIX-UHFFFAOYSA-N n-isoquinolin-1-ylisoquinolin-1-amine Chemical compound C1=CC=C2C(NC=3C4=CC=CC=C4C=CN=3)=NC=CC2=C1 MEYJVORNUBJAIX-UHFFFAOYSA-N 0.000 description 1
- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical group C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-UHFFFAOYSA-N 0.000 description 1
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- FWRJQLUJZULBFM-UHFFFAOYSA-N n-phenyl-n-[4-[4-(n-tetracen-2-ylanilino)phenyl]phenyl]tetracen-2-amine Chemical group C1=CC=CC=C1N(C=1C=C2C=C3C=C4C=CC=CC4=CC3=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=C4C=C5C=CC=CC5=CC4=CC3=CC=2)C=C1 FWRJQLUJZULBFM-UHFFFAOYSA-N 0.000 description 1
- LKKVSUQIZFOEEK-UHFFFAOYSA-N n-pyridin-2-ylquinolin-2-amine Chemical compound C=1C=C2C=CC=CC2=NC=1NC1=CC=CC=N1 LKKVSUQIZFOEEK-UHFFFAOYSA-N 0.000 description 1
- USPVIMZDBBWXGM-UHFFFAOYSA-N nickel;oxotungsten Chemical compound [Ni].[W]=O USPVIMZDBBWXGM-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
TBADN 중 화학식 1-1의 화합물에 대한 평가 결과a | ||||||
실시예 | 유형 | 도판트 (농도)1 | 수율 (cd/A) | λmax (㎚) | 색 | 손실(%) (275 h)2 |
3-1 | 비교 | (0.0%) | 1.50 | 460 | 청색 | 55.2 |
3-2 | 본 발명 | (0.2%) | 1.70 | 444 | 청색 | 56.6 |
3-3 | 본 발명 | (0.4%) | 1.72 | 444 | 청색 | 52.9 |
3-4 | 본 발명 | (0.6%) | 1.80 | 444 | 청색 | 45.6 |
3-5 | 본 발명 | (0.8%) | 1.66 | 444 | 청색 | 39.6 |
3-6 | 본 발명 | (1.0%) | 1.66 | 444 | 청색 | 36.9 |
평균 | 1.71 | 46.3 | ||||
a20mA/㎝2의 전류 밀도에 대해 보고된 데이터 1호스트 중 중량% 2안정성 시험은 70℃에서 수행함 |
TBADN 중 화학식 1-5의 화합물에 대한 평가 결과a | ||||||
실시예 | 유형 | 도판트 (농도)1 | 수율 (cd/A) | λmax (㎚) | 색 | 손실(%) (200 h)2 |
4-1 | 비교 | (0.0%) | 1.56 | 456 | 청색 | 51.0 |
4-2 | 본 발명 | (0.2%) | 1.76 | 448 | 청색 | 52.4 |
4-3 | 본 발명 | (0.5%) | 1.85 | 448 | 청색 | 51.1 |
4-4 | 본 발명 | (0.75%) | 1.94 | 448 | 청색 | 47.1 |
4-5 | 본 발명 | (1.0%) | 1.89 | 448 | 청색 | 45.3 |
4-6 | 본 발명 | (2.0%) | 1.89 | 448 | 청색 | 43.2 |
평균 | 1.87 | 47.8 | ||||
a20mA/㎝2의 전류 밀도에 대해 보고된 데이터 1호스트 중 중량% 2안정성 시험은 70℃에서 수행함 |
CBP 중 화학식 1-1의 화합물에 대한 평가 결과a | |||||
실시예 | 유형 | 도판트 (농도)1 | 수율 (cd/A) | λmax (㎚) | 색 |
5-1 | 비교 | (0.0%) | 1.56 | 472 | 청색 |
5-2 | 본 발명 | (0.2%) | 2.18 | 444 | 청색 |
5-3 | 본 발명 | (0.4%) | 2.08 | 444 | 청색 |
5-4 | 본 발명 | (0.6%) | 2.09 | 444 | 청색 |
5-5 | 본 발명 | (0.8%) | 2.10 | 444 | 청색 |
5-6 | 본 발명 | (1.0%) | 1.80 | 444 | 청색 |
평균 | 2.05 | ||||
a20mA/㎝2의 전류 밀도에 대해 보고된 데이터 1호스트 중 중량% |
TBADN 중 화학식 1-2의 화합물에 대한 평가 결과a | ||||||
실시예 | 유형 | 도판트 (농도)1 | 수율 (cd/A) | λmax (㎚) | 색 | 손실(%) (200 h)2 |
6-1 | 비교 | (0.0%) | 1.42 | 460 | 청색 | 33.6 |
6-2 | 본 발명 | (0.25%) | 1.55 | 464 | 청색 | 28.8 |
6-3 | 본 발명 | (0.5%) | 1.61 | 464 | 청색 | 31.8 |
6-4 | 본 발명 | (0.75%) | 1.52 | 464 | 청색 | 32.6 |
6-5 | 본 발명 | (2.0%) | 1.64 | 468 | 청색 | 28.8 |
평균 | 1.58 | 30.5 | ||||
a20mA/㎝2의 전류 밀도에 대해 보고된 데이터 1호스트 중 중량% 2안정성 시험은 70℃에서 수행함 |
TBADN 중 화학식 1-3의 화합물에 대한 평가 결과a | ||||||
실시예 | 유형 | 도판트 (농도)1 | 수율 (cd/A) | λmax (㎚) | 색 | 손실(%) (200 h)2 |
7-1 | 비교 | (0.0%) | 1.51 | 464 | 청색 | 44.4 |
7-2 | 본 발명 | (0.25%) | 1.71 | 472 | 청색 | 22.3 |
7-3 | 본 발명 | (0.5%) | 1.78 | 472 | 청색 | 24.7 |
7-4 | 본 발명 | (0.75%) | 1.83 | 472 | 청색 | 25.2 |
7-5 | 본 발명 | (1.0%) | 1.73 | 472 | 청색 | 22.9 |
7-6 | 본 발명 | (2.0%) | 1.81 | 472 | 청색 | 20.4 |
평균 | 1.77 | 23.1 | ||||
a20mA/㎝2의 전류 밀도에 대해 보고된 데이터 1호스트 중 중량% 2안정성 시험은 70℃에서 수행함 |
TBADN 중 도판트에 대한 평가 결과a | |||||
도판트 | 도판트 (농도)1 | 수율 (cd/A) | λmax (㎚) | 색 | 손실(%) (200 h)2 |
1-27 | 1.0% | 2.27 | 452 | 청색 | 26.8% |
1-29 | 1.0% | 2.18 | 456 | 청색 | 11.9% |
1-32 | 1.0% | 2.47 | 452 | 청색 | 32.4% |
1-35 | 1.0% | 2.63 | 456 | 청색 | 24.0% |
a20mA/㎝2의 전류 밀도에 대해 보고된 데이터 1호스트 중 중량% 2안정성 시험은 70℃에서 수행함 |
TBADN 중 도판트에 대한 평가 결과a | |||||
도판트 | 도판트 (농도)1 | 수율 (cd/A) | λmax (㎚) | 색 | 손실(%) (200 h)2 |
1-27 | 1.0% | 1.65 | 448 | 청색 | 22.3% |
1-29 | 1.0% | 1.97 | 452 | 청색 | 16.8% |
1-34 | 1.0% | 2.39 | 452 | 청색 | 28.0% |
a20mA/㎝2의 전류 밀도에 대해 보고된 데이터 1호스트 중 중량% 2안정성 시험은 70℃에서 수행함 |
TBADN 중 도판트에 대한 평가 결과a | |||||
도판트 | 도판트 (농도)1 | 수율 (cd/A) | λmax (㎚) | 색 | 손실(%) (200 h)2 |
1-30 | 1.0% | 1.48 | 448 | 청색 | 42.1% |
1-31 | 1.0% | 2.12 | 456 | 청색 | * |
1-32 | 1.0% | 1.66 | 452 | 청색 | 22.8% |
1-33 | 1.0% | 2.05 | 448 | 청색 | 17.7% |
1-36 | 1.0% | 2.96 | 464 | 청색 | 22.0% |
1-37 | 1.0% | 3.37 | 464 | 청색 | 19.0% |
a20mA/㎝2의 전류 밀도에 대해 보고된 데이터 1호스트 중 중량% 2안정성 시험은 70℃에서 수행함 *조기 디바이스 단락으로 인한 미완결된 시험 |
트리사이클릭 붕소 착체의 비교 | |||
실시예 | 유형 | 구조 | λmax 1 |
8-1 | 본 발명 | 430 (청색) | |
8-2 | 비교 | 520 (녹색) | |
8-3 | 비교 | 590 (오렌지색) | |
8-4 | 비교 | 696 (암적색) | |
1 용액 형광 |
Claims (10)
- 호스트 및 도판트를 함유한 발광층을 포함하는 유기 발광 다이오드(OLED) 디바이스로서, 도판트가 탈양성자화 비스(아지닐)아민 리간드의 2개의 고리 질소에 의해 착화된 붕소 화합물을 포함하는 OLED 디바이스.
- 제 1 항에 있어서,도판트가 호스트의 0.01 내지 10중량%의 양으로 존재하는 OLED 디바이스.
- 제 1 항에 있어서,도판트가 호스트의 0.1 내지 5.0중량%의 양으로 존재하는 OLED 디바이스.
- 제 1 항 내지 제 3 항중 어느 한 항에 있어서,아지닐기가 피리딜기인 OLED 디바이스.
- 제 1 항 내지 제 3 항중 어느 한 항에 있어서,호스트가 킬레이트화 옥시노이드 화합물, 디카바졸-비페닐 화합물 또는 안트라센 화합물을 포함하는 OLED 디바이스.
- 제 1 항 내지 제 3 항중 어느 한 항에 있어서,치환기가 청색 색조를 갖는 도판트로부터 방출된 광을 제공하도록 선택된 OLED 디바이스.
- 제 1 항 내지 제 3 항중 어느 한 항에 있어서,도판트 화합물이 하기 화학식 1로 표시되는 OLED 디바이스:화학식 1상기 식에서,A 및 A'는 하나 이상의 질소를 함유하는 6원 방향족 고리계에 상응하는 독립적인 아진 고리계를 나타내고,Xa 및 Xb는 각각 독립적으로 선택된 치환기이며, 이들은 결합하여 A 또는 A'에 접합된 고리 기를 형성할 수 있고,m 및 n은 독립적으로 0 내지 4이고,Za 및 Zb는 독립적으로 선택된 치환기이고,1, 2, 3, 4, 1', 2', 3' 및 4'는 탄소 원자 또는 질소 원자로서 독립적으로 선택된다.
- 제 1 항 내지 제 3 항중 어느 한 항에 있어서,2개의 고리 질소가 상이한 6,6 접합 고리계의 하나 이상이 아릴 또는 헤테로아릴 치환기를 함유하는 상기 접합 고리계의 원인 OLED 디바이스.
- 제 7 항에 있어서,A 및 A'는 하나 이상의 질소를 함유하는 6원 방향족 고리계에 상응하는 독립적인 아진 고리계를 나타내고,Xa 및 Xb는 각각 독립적으로 선택된 치환기이며, 이들 각각은 결합하여 A 및 A' 고리에 각각 접합된 고리로서 B 및 B' 고리를 형성하고, 여기서 A, A', B 또는 B' 고리는 아릴 또는 헤테로아릴 치환기를 포함하고,m 및 n은 독립적으로 2 내지 4이고,Za 및 Zb는 독립적으로 선택된 치환기이고,1, 2, 3, 4, 1', 2', 3' 및 4'는 탄소 원자 또는 질소 원자로서 독립적으로 선택된다.
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US10/183,242 US6661023B2 (en) | 2002-02-28 | 2002-06-27 | Organic element for electroluminescent devices |
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- 2003-02-17 EP EP03075445A patent/EP1340798B1/en not_active Expired - Lifetime
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Also Published As
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TW200303348A (en) | 2003-09-01 |
US6661023B2 (en) | 2003-12-09 |
EP1340798A3 (en) | 2004-02-04 |
JP4050633B2 (ja) | 2008-02-20 |
KR20030071581A (ko) | 2003-09-03 |
DE60300488T2 (de) | 2006-02-23 |
CN100380706C (zh) | 2008-04-09 |
US20030201415A1 (en) | 2003-10-30 |
EP1340798A2 (en) | 2003-09-03 |
CN1441630A (zh) | 2003-09-10 |
JP2003257670A (ja) | 2003-09-12 |
DE60300488D1 (de) | 2005-05-19 |
TWI267543B (en) | 2006-12-01 |
EP1340798B1 (en) | 2005-04-13 |
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