WO2008082164A1 - Cyclized aryl amine derivatives and organic light emitting diode using the same - Google Patents
Cyclized aryl amine derivatives and organic light emitting diode using the same Download PDFInfo
- Publication number
- WO2008082164A1 WO2008082164A1 PCT/KR2007/006912 KR2007006912W WO2008082164A1 WO 2008082164 A1 WO2008082164 A1 WO 2008082164A1 KR 2007006912 W KR2007006912 W KR 2007006912W WO 2008082164 A1 WO2008082164 A1 WO 2008082164A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- substituted
- unsubstituted
- aryl amine
- oled
- Prior art date
Links
- 150000004982 aromatic amines Chemical class 0.000 title claims abstract description 23
- 230000005525 hole transport Effects 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 22
- 239000010410 layer Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- -1 naphthalene-1-yl Chemical group 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000009477 glass transition Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- MWMNLUGPPZOPJQ-UHFFFAOYSA-N 4-(4-aminophenyl)-3-naphthalen-1-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC2=CC=CC=C12 MWMNLUGPPZOPJQ-UHFFFAOYSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 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 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- DPKKOVGCHDUSAI-UHFFFAOYSA-N 1,3-dibromo-5-methylbenzene Chemical compound CC1=CC(Br)=CC(Br)=C1 DPKKOVGCHDUSAI-UHFFFAOYSA-N 0.000 description 1
- BSHSCWRTJSBWLY-UHFFFAOYSA-N 1-cyclohexyl-4-phenylbenzene Chemical group C1CCCCC1C1=CC=C(C=2C=CC=CC=2)C=C1 BSHSCWRTJSBWLY-UHFFFAOYSA-N 0.000 description 1
- SRQOBNUBCLPPPH-UHFFFAOYSA-N 1-ethyl-4-phenylbenzene Chemical group C1=CC(CC)=CC=C1C1=CC=CC=C1 SRQOBNUBCLPPPH-UHFFFAOYSA-N 0.000 description 1
- GPYDMVZCPRONLW-UHFFFAOYSA-N 1-iodo-4-(4-iodophenyl)benzene Chemical group C1=CC(I)=CC=C1C1=CC=C(I)C=C1 GPYDMVZCPRONLW-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical group C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
Classifications
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D259/00—Heterocyclic compounds containing rings having more than four nitrogen atoms as the only ring hetero atoms
-
- 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]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/17—Carrier injection layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to a cyclized aryl amine derivative and an organic light emitting diode (OLED) using the same, and more particularly to a new cyclized aryl amine derivative represented by Formula 1, as defined herein, which is used as a hole transport material of an OLED having a multilayered structure, and thus provides an OLED of high thermal stability, improved lifetime, and high luminous brightness/efficiency, and an OLED using the same.
- OLED organic light emitting diode
- organic EL electroluminescence
- a fluorescent material when an electric field is formed by the organic semiconductor inserted between both electrodes, a fluorescent material emits light by recombination energy of a hole injected from an anode and an electron injected from a cathode.
- Such an OLED is a new concept advanced display device, and has been recently widely used for outside/inside windows of a cellular phone, displays of an MP3 player and a digital camera, etc. due to low power consumption, a high response speed, and a wide viewing angle.
- the OLED instead of PDP or LCD, may be applied to a wall-mounted TV and a scrolling TV.
- the first report regarding an OLED was "a low-voltage- driven organic electroluminescent device using a double layered structure" (C.
- An OLED includes a hole transport layer and an electron transport layer, and herein, the hole transport layer adjacent to an anode contains a hole transport material and mainly functions of transporting a hole to a light-emitting layer within an OLED device, and on the other hand, the electron transport layer adjacent to a cathode contains an electron transport material and functions of transporting an electron within the OLED device.
- the hole transport layer adjacent to an anode contains a hole transport material and mainly functions of transporting a hole to a light-emitting layer within an OLED device
- the electron transport layer adjacent to a cathode contains an electron transport material and functions of transporting an electron within the OLED device.
- an OLED can show luminescence properties of high efficiency and high brightness only when the OLED has a multilayer system including a hole transfer layer (such as a hole injection layer and a hole transport layer) , an electron transport layer, a hole blocking layer, etc.
- a device in order to utilize the OLED and improve its properties, a device has to include a thermally and electrically stabilized material (especially, as a hole transport material) , as well as the above described multilayer system because, when heat is generated from a device by voltage application, molecules having low thermal stability are rearranged due to low crystal stability. Accordingly, there occurs partial crystallization, and thus, there exists an inhomogeneous portion.
- an electric field is concentrated on the inhomogeneous portion, thereby causing deterioration and destruction of the device. Therefore, because of the above described reasons, an organic layer in an amorphous state is generally used. Also, since an OLED is a current-injection type device, a material having low glass transition temperature (Tg) generates heat in use, and thus deteriorates the OLED, and shortens the lifetime of the device. Therefore, it is preferable that a material used for the OLED has high glass transition temperature.
- a hole transport material which has been used up to now, includes m-MTDATA[4, 4 ' , 4"-tris (N-3-methylphenyl-N- phenylamino) -triphenylamine, 2-TNATA[4, 4 ' , 4"-tris (N-
- NPB N, N'-di (naphthalene-1-yl) -N, N 1 -diphenylbenzidine
- m-MTDATA and 2-TNATA have low glass transition temperatures (Tg) of 78 ° C and 108 ° C, respectively, and also various problems in the mass production process. Thus, it is difficult to realize full natural colors.
- TPD and NPB have low glass transition temperatures (Tg) of 60 ° C and 96 ° C, and thus shorten the lifetime of a device due to the described reasons.
- the conventional hole transport material used for an OLED still has many problems, and is reguired to be improved in properties such as thermal stability, glass transition temperature, etc. Therefore, it is required that a good material, which improves the luminous efficiency of an OLED, and has high thermal stability and high glass transition temperature, be developed.
- the present invention has been made in view of the above-mentioned problems, and the present invention provides a cyclized aryl amine derivative represented by Formula 1 as defined herein, which is used as a hole transport material of an organic light emitting diode (OLED) having a multilayered structure, and thus provides an OLED of high thermal stability, improved lifetime, and high brightness/luminous efficiency, and an OLED using the same.
- OLED organic light emitting diode
- HIL hole injection layer
- HTL hole transport layer
- an OLED including a hole injection layer and/or a hole transport layer being prepared by the cyclized aryl amine derivative according to the present invention.
- the present invention relates to a cyclized aryl amine derivative represented by Formula 1. [ Formula 1 ]
- Ari - Arg may be the same or different from each other, and each of Ari ⁇ Ar 8 is independently an aromatic ring selected from the group including benzene, naphthalene, biphenyl, and anthracene; and each of Ari ⁇ Ar 6 may be independently substituted with a group selected from the group including a substituted or unsubstituted Ci ⁇ C 3 o linear, branched or cyclic alkyl or alkenyl group, a substituted or unsubstituted Ci-C 30 condensed ring, a substituted or unsubstituted Ci-C 30 aryl group, a substituted or unsubstituted
- Ci ⁇ C 30 arylalkyl group a substituted or unsubstituted Ci-C 30 aryloxy group, a substituted or unsubstituted Ci-C 3O aryamine group, a substituted or unsubstituted Ci-C 30 heteroaryl group, a substituted or unsubstituted Ci-C 30 heterocycloalkyl group, and halogen.
- the present invention relates to a cyclized aryl amine derivative represented by Formula 1 as defined herein, which is used as a hole transport material of an organic light emitting diode (OLED) having a multilayered structure, and thus provides an OLED having high thermal stability, improved lifetime, high brightness and high luminous efficiency, and an OLED using the same.
- OLED organic light emitting diode
- the substituted or unsubstituted Ci-C 30 alkyl group includes, but is not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group, a 2- phenyl isopropyl group, a trichloromethyl group, a trifluoromethyl group, a benzyl group, an a-phenoxybenzyl group, an a,a-dimethylbenzyl group, an a, a-methylphenylbenzyl group, an a, a-ditrifluoromethylbenzyl group, a triphenylmethyl group, etc.
- the substituted or unsubstituted Ci-C 30 condensed ring includes, but is not limited to, naphthalene, anthracene, tetracene, phenanthrene, etc.
- the substituted or unsubstituted Ci-C 30 aryl group includes, but is not limited to, a phenyl group, a 2- methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a biphenyl group, a 4- methylbiphenyl group, a 4-ethylbiphenyl group, a 4- cyclohexylbiphenyl group, a terphenyl group, a 3,5- dichlorophenyl group, a naphthyl group, a 5-methylnaphthyl group, an anthryl group, a pyrenyl group, etc.
- the substituted or unsubstituted Ci-C 30 arylalkyl group includes, but is not limited to, a benzyl group, an ⁇ - methylbenzyl group, an ⁇ -ethylbenzyl group, an ⁇ , ⁇ -dimethyl benzyl group, a 4-methylbenzyl group, a 4-ethylbenzyl group, a 2-tert-butyl benzyl group, a 4-n-octyl benzyl group, a naphthylmethyl group, a diphenylmethyl group, etc.
- the substituted or unsubstituted Ci-C 30 aryloxy group includes, but is not limited to, a phenoxyl group, a naphthyloxyl group, an anthryloxyl group, a pyrenyloxyl group, a fluorantenyloxyl group, a chrysenyloxyl group, a perylenyloxyl group, etc.
- the substituted or unsubstituted Ci-C 30 arylamine group includes, but is not limited to, a diphenylamine group, a dinaphthylamine group, a dibiphenylamine group, a phenylnaphthylamine group, a phenyldiphenylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group, a triphenylamine group, etc.
- the aryl group is the same as defined above, and the heteroaryl group includes, but is not limited to, a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a pyridazine group, a quinolinyl group, an isoquinoline group, an acridine group, etc.
- the substituted or unsubstituted C ⁇ C 3 o heterocycloalkyl group includes, but is not limited to, a pyridyl group, a diethyl group, a furyl group, a quinolyl group, a carbazolyl group, etc.
- the substituents may be substituted or unsubstituted, and herein, when the substituents may include, but are not limited to: halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.; alkyl groups, such as a methyl group, an ethyl group, an n-propyl group, and an isopropyl group; alkoxyl groups, such as a methoxyl group and an ethoxyl group; aryloxy groups, such as a phenoxyl group; arylalkyl groups, such as a benzy] group, a phenethyl group, and a phenylpropyl group; a nitro group; a cyano group; substituted amino groups such as a dimethylamino group, a dibenzylamino group, a diphenylamino group, and a morpholino group; ary
- novel cyclized aryl amine derivative represented by Formula 1 of the present invention representatively includes the following compouonds:
- an OLED includes a layered structure including a substrate (glass or plastic) , an anode, a hole injection layer (HIL) , a hole transport layer (HTL) , an organic emitting layer (EML), an electron injection layer (EIL), an electron transport layer (ETL), and a cathode.
- HIL hole injection layer
- HTL hole transport layer
- EML organic emitting layer
- EIL electron injection layer
- ETL electron transport layer
- cathode cyclized aryl amine derivative represented by Formula 1 of the present invention may be used as a hole transport material
- FIG. 1 illustrates an UV/VTS spectrum and a PL spectrum of DBDNBA of Example 1
- FIG. 2 illustrates an UV/VIS spectrum and a PL spectrum of m-DBDNBA of Example 2.
- Example 1 preparation of a compound DBDNBA according to the present invention
- reaction solution was cooled to room temperature, purified by chromatography on a thin silica pad, and was cleaned by dichloromethane. Next, through an enrichment process, the used solvent was removed. Then, the resultant product was dissolved in 30 ml of dichloromethane, and was slowly added in 450 ml of methanol to obtain a solid of N4,N4' -di (naphthalene-1-yl) biphenyl-4, 4' - diamine (1.7g yield 80%).
- the maximum absorption wavelength was 335 nm, and the maximum light-emitting wavelength was 444 nm.
- the energy level of HOMO highest occupied molecular orbital
- the energy level of LUMO lowest unoccupied molecular orbital
- the maximum absorption wavelength was 346 nm, and the maximum light-emitting wavelength was 458 nm.
- the energy level of HOMO highest occupied molecular orbital
- the energy level of LUMO lowest unoccupied molecular orbital
- a cyclized aryl amine derivative according to the present invention has high thermal stability because of high glass transition temperature and thermal decomposition temperature. Accordingly, when the cyclized aryl amine derivative is used as a hole transport material of an organic light emitting diode (OLED) having a multilayered structure, it is possible to solve the problem of low brightness and luminous efficiency, which is a main disadvantage of a conventional OLED. Also, since the cyclized aryl amine derivative has high glass transition temperature, it is possible to manufacture an OLED having high thermal stability and advanced efficiency, and to commercialize an OLED device of full natural colors, which requires high efficiency and brightness, and improved lifetime.
- OLED organic light emitting diode
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Abstract
Disclosed is a cyclized aryl amine derivative and an organic light emitting diode (OLED) using the same, and more particularly a cyclized aryl amine derivative represented by Formula 1, which is used as a hole transport material of an OLED having a multilayered structure, and thus provides an OLED of high thermal stability, improved lifetime, and high luminous brightness/efficiency, and an OLED using the same.
Description
[DESCRIPTION] [invention Title]
CYCLIZED ARYL AMINE DERIVATIVES AND ORGANIC LIGHT EMITTING DIODE USING THE SAME [Technical Field]
The present invention relates to a cyclized aryl amine derivative and an organic light emitting diode (OLED) using the same, and more particularly to a new cyclized aryl amine derivative represented by Formula 1, as defined herein, which is used as a hole transport material of an OLED having a multilayered structure, and thus provides an OLED of high thermal stability, improved lifetime, and high luminous brightness/efficiency, and an OLED using the same. [Background Art] In general, an organic light emitting diode (OLED) , which is also referred to as organic EL (electroluminescence) , is a self emitting device using an organic (low molecular weight or polymer) semiconductor of a conjugated structure as a light-emitting material. In the OLED, when an electric field is formed by the organic semiconductor inserted between both electrodes, a fluorescent material emits light by recombination energy of a hole injected from an anode and an electron injected from a cathode. Such an OLED is a new concept advanced display device, and has been recently widely used for outside/inside windows of a cellular phone, displays of an MP3 player and a digital camera, etc. due to low power consumption, a high response speed, and a wide viewing angle. Also, it is expected that the OLED, instead of PDP or LCD, may be applied to a wall-mounted TV and a scrolling TV. The first report regarding an OLED was "a low-voltage- driven organic electroluminescent device using a double layered structure" (C. W. Tang, S .A.Vanslyke, Applied Physics Letters, 51,913 (1987)) by C. W. Tang et al. of the Eastman
Kodak Company in 1987. Also, since patent application (US Patent No. 4,356,429) regarding an organic light-emitting diode of a double structure including two organic layers between an anode and a cathode, light-emitting device materials including a variety of organic materials have been developed.
An OLED includes a hole transport layer and an electron transport layer, and herein, the hole transport layer adjacent to an anode contains a hole transport material and mainly functions of transporting a hole to a light-emitting layer within an OLED device, and on the other hand, the electron transport layer adjacent to a cathode contains an electron transport material and functions of transporting an electron within the OLED device. Recently, materials forming the hole transport layer and the electron transport layer have been actively researched.
Especially, an OLED can show luminescence properties of high efficiency and high brightness only when the OLED has a multilayer system including a hole transfer layer (such as a hole injection layer and a hole transport layer) , an electron transport layer, a hole blocking layer, etc. In addition, in order to utilize the OLED and improve its properties, a device has to include a thermally and electrically stabilized material (especially, as a hole transport material) , as well as the above described multilayer system because, when heat is generated from a device by voltage application, molecules having low thermal stability are rearranged due to low crystal stability. Accordingly, there occurs partial crystallization, and thus, there exists an inhomogeneous portion. Then, an electric field is concentrated on the inhomogeneous portion, thereby causing deterioration and destruction of the device. Therefore, because of the above described reasons, an organic layer in an amorphous state is generally used. Also, since an
OLED is a current-injection type device, a material having low glass transition temperature (Tg) generates heat in use, and thus deteriorates the OLED, and shortens the lifetime of the device. Therefore, it is preferable that a material used for the OLED has high glass transition temperature.
A hole transport material, which has been used up to now, includes m-MTDATA[4, 4 ' , 4"-tris (N-3-methylphenyl-N- phenylamino) -triphenylamine, 2-TNATA[4, 4 ' , 4"-tris (N-
(naphthylene-2-yl) -N-phenylamino) -triphenylamine] , TPD [N, N'- diphenyl-N,N' -di (3-methylphenyl) -4,4' -diaminobiphenyl] ,
NPB[N, N'-di (naphthalene-1-yl) -N, N1 -diphenylbenzidine] , etc. Herein, m-MTDATA and 2-TNATA have low glass transition temperatures (Tg) of 78 °C and 108°C, respectively, and also various problems in the mass production process. Thus, it is difficult to realize full natural colors. Also, TPD and NPB have low glass transition temperatures (Tg) of 60°C and 96°C, and thus shorten the lifetime of a device due to the described reasons.
There was Japanese Patent Application Laid-open No. 2006-128716, regarding a 4, 4 ' -biphenylenediamine derivative including a structure as described below, and an OLED containing the same as a hole transport layer material. According to the technology, in such a device, driving voltage is decreased, and luminescence lifetime is significantly improved. Also, there was US Patent Publication No. 2006/0082294, regarding a phenylenediamine derivative which has a hole mobility of 10"4cm2/V when the derivative is used as a layer or a zone, and an organic EL device using the same. According to the technology, in such a device, driving voltage is decreased, and lifetime is improved.
However, the conventional hole transport material used for an OLED still has many problems, and is reguired to be improved in properties such as thermal stability, glass
transition temperature, etc. Therefore, it is required that a good material, which improves the luminous efficiency of an OLED, and has high thermal stability and high glass transition temperature, be developed. [Disclosure]
[Technical Problem]
Therefore, the present invention has been made in view of the above-mentioned problems, and the present invention provides a cyclized aryl amine derivative represented by Formula 1 as defined herein, which is used as a hole transport material of an organic light emitting diode (OLED) having a multilayered structure, and thus provides an OLED of high thermal stability, improved lifetime, and high brightness/luminous efficiency, and an OLED using the same. In accordance with an aspect of the present invention, there is provided a cyclized aryl amine compound derivative represented by Formula 1.
In accordance with another aspect of the present invention, there is provided a hole injection layer (HIL) prepared by the cyclized aryl amine derivative according to the present invention.
In accordance with a further aspect of the present invention, there is provided a hole transport layer (HTL) prepared by the cyclized aryl amine derivative according to the present invention.
In accordance with a still further aspect of the present invention, there is provided an OLED including a hole injection layer and/or a hole transport layer being prepared by the cyclized aryl amine derivative according to the present invention.
[Technical Solution]
The present invention relates to a cyclized aryl amine derivative represented by Formula 1.
[ Formula 1 ]
In Formula 1, Ari - Arg may be the same or different from each other, and each of Ari ~ Ar8 is independently an aromatic ring selected from the group including benzene, naphthalene, biphenyl, and anthracene; and each of Ari ~ Ar6 may be independently substituted with a group selected from the group including a substituted or unsubstituted Ci~C3o linear, branched or cyclic alkyl or alkenyl group, a substituted or unsubstituted Ci-C30 condensed ring, a substituted or unsubstituted Ci-C30 aryl group, a substituted or unsubstituted
Ci~C30 arylalkyl group, a substituted or unsubstituted Ci-C30 aryloxy group, a substituted or unsubstituted Ci-C3O aryamine group, a substituted or unsubstituted Ci-C30 heteroaryl group, a substituted or unsubstituted Ci-C30 heterocycloalkyl group, and halogen.
Hereinafter, the present invention will be described in more detail.
The present invention relates to a cyclized aryl amine derivative represented by Formula 1 as defined herein, which is used as a hole transport material of an organic light emitting diode (OLED) having a multilayered structure, and thus provides an OLED having high thermal stability, improved lifetime, high brightness and high luminous efficiency, and an OLED using the same.
Hereinafter, the substituents of Formula 1 will be defined.
"The substituted or unsubstituted Ci-C30 alkyl group"
includes, but is not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group, a 2- phenyl isopropyl group, a trichloromethyl group, a trifluoromethyl group, a benzyl group, an a-phenoxybenzyl group, an a,a-dimethylbenzyl group, an a, a-methylphenylbenzyl group, an a, a-ditrifluoromethylbenzyl group, a triphenylmethyl group, etc. "The substituted or unsubstituted C2-C30 alkenyl group" includes, but is not limited to, propenyl, butenyl, etc.
"The substituted or unsubstituted Ci-C30 condensed ring" includes, but is not limited to, naphthalene, anthracene, tetracene, phenanthrene, etc. "The substituted or unsubstituted Ci-C30 aryl group" includes, but is not limited to, a phenyl group, a 2- methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, a biphenyl group, a 4- methylbiphenyl group, a 4-ethylbiphenyl group, a 4- cyclohexylbiphenyl group, a terphenyl group, a 3,5- dichlorophenyl group, a naphthyl group, a 5-methylnaphthyl group, an anthryl group, a pyrenyl group, etc.
"The substituted or unsubstituted Ci-C30 arylalkyl group" includes, but is not limited to, a benzyl group, an α- methylbenzyl group, an α-ethylbenzyl group, an α,α-dimethyl benzyl group, a 4-methylbenzyl group, a 4-ethylbenzyl group, a 2-tert-butyl benzyl group, a 4-n-octyl benzyl group, a naphthylmethyl group, a diphenylmethyl group, etc.
"The substituted or unsubstituted Ci-C30 aryloxy group" includes, but is not limited to, a phenoxyl group, a naphthyloxyl group, an anthryloxyl group, a pyrenyloxyl group, a fluorantenyloxyl group, a chrysenyloxyl group, a perylenyloxyl group, etc.
"The substituted or unsubstituted Ci-C30 arylamine group" includes, but is not limited to, a diphenylamine group, a dinaphthylamine group, a dibiphenylamine group, a phenylnaphthylamine group, a phenyldiphenylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group, a triphenylamine group, etc.
In "the substituted or unsubstituted Cχ~C3o heteroaryl group", "the aryl group" is the same as defined above, and the heteroaryl group includes, but is not limited to, a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a pyridazine group, a quinolinyl group, an isoquinoline group, an acridine group, etc. "The substituted or unsubstituted Cχ~C3o heterocycloalkyl group" includes, but is not limited to, a pyridyl group, a diethyl group, a furyl group, a quinolyl group, a carbazolyl group, etc.
The substituents may be substituted or unsubstituted, and herein, when the substituents may include, but are not limited to: halogen atoms, such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.; alkyl groups, such as a methyl group, an ethyl group, an n-propyl group, and an isopropyl group; alkoxyl groups, such as a methoxyl group and an ethoxyl group; aryloxy groups, such as a phenoxyl group; arylalkyl groups, such as a benzy] group, a phenethyl group, and a phenylpropyl group; a nitro group; a cyano group; substituted amino groups such as a dimethylamino group, a dibenzylamino group, a diphenylamino group, and a morpholino group; aryl groups, such as a phenyl group, a tolyl group, a biphenyl group, a naphthyl group, an anthryl group, and a pyrenyl group; and heterocyclic groups, such as a pyridyl group, a tiethyl group, a furyl group, a quinolyl group, and a
carbazolyl group.
The novel cyclized aryl amine derivative represented by Formula 1 of the present invention representatively includes the following compouonds:
In general, an OLED includes a layered structure including a substrate (glass or plastic) , an anode, a hole injection layer (HIL) , a hole transport layer (HTL) , an organic emitting layer (EML), an electron injection layer (EIL), an electron transport layer (ETL), and a cathode. Also, the cyclized aryl amine derivative represented by Formula 1 of the present invention may be used as a hole transport material
(that is, a material used for a hole injection layer and/or a hole transport layer in an OLED of a layered structure) , or else, as an emitting layer material.
[Description of Drawings]
FIG. 1 illustrates an UV/VTS spectrum and a PL spectrum of DBDNBA of Example 1; and
FIG. 2 illustrates an UV/VIS spectrum and a PL spectrum of m-DBDNBA of Example 2. [Best Mode]
Hereinafter, the process of preparing an anthracene derivative according to the present invention will now be described in detail with reference to following Examples.
However, the following examples are illustrative only, and the scope of the present invention is not limited thereto.
Examples and Comparative Examples
In the present Examples, representative compounds represented by Formula 1 of the present invention were obtained through the following processes. Example 1: preparation of a compound DBDNBA according to the present invention
[Reaction Scheme 1]
As shown in Reaction Scheme L, 2g of 4, 4' -diiodobiphenyl (4.93 mmol) and 1.4g of naphthalene-1-amine (9.86 mmol) were dissolved in toluene, and then, 0.2Og of tris (dibenzylidine acetone) dipalladium (0.20 mmol) was added under a nitrogen atmosphere. Then, 1.2Og of sodium butoxide (12.44 mmol) was added to the reaction mixture, and 0.09g of (t-bu)3P (0.39 mmol) was fed into a reactor. The reaction mixture was refluxed and agitated for 4 hours. The reaction solution was cooled to room temperature, purified by chromatography on a thin silica pad, and was cleaned by dichloromethane. Next, through an enrichment process, the used solvent was removed. Then, the resultant product was dissolved in 30 ml of dichloromethane, and was slowly added in 450 ml of methanol to obtain a solid of N4,N4' -di (naphthalene-1-yl) biphenyl-4, 4' - diamine (1.7g yield 80%).
[Reaction Scheme 2]
DBDNBA
As shown in Reaction Scheme 2, 2g of N4,N4'- di (naphthalene-1-yl) biphenyl-4, 4' -diamine (4.58 mmol) prepared by Reliction Scheme 1, and 1.08g of dibromobenzene (4.58 mmol) were dissolved in toluene, and then, O.lδg of tris
(dibenzylidine acetone) dipalladium (0.18 mmol) was added under a nitrogen atmosphere. Then, l.lOg of sodium butoxide (11.44 mmol) was added to the reaction mixture, and 0.08g of (t-bu)3P
(0.36 mmol) was fed into a reactor. The reaction mixture was refluxed and agitated for 6 hours. The reaction solution was cooled to room temperature, purified by chromatography on a thin silica pad, and was cleaned by dichloromethane. Next, through an enrichment process, the used solvent was removed. Then, the resultant product was purified through chromatography using dichloromethane/n-hexane solution (1:5) to obtain Ig of a compound (yield 42%) .
1H-NMR(CDCl3, 300NMR) δ (ppm) 8.03(d, 4H), 7.61(d, 4H), 7.46(m, 16H), 7.16(m, 8H), 6.76(t, 2H), 6,52(m, 12H), 5.82(d, 4H), 5.66(s, 2H)
As shown in FIG. 1, based on the result of the determination of optical and thermal characteristics on the compound DBDNBA as prepared above, the maximum absorption wavelength was 335 nm, and the maximum light-emitting wavelength was 444 nm. In the measurement performed in a THF solution, the energy level of HOMO (highest occupied molecular orbital) was 5.2 eV, and the energy level of LUMO (lowest unoccupied molecular orbital) was 2.1 eV. As a result of thermogravimetric analysis (TGA) , it was determined that the
compound is stable even at temperatures higher than 500°C.
Example 2 : preparation of a compound m-DBDNBA according to the present invention [Reaction Scheme 3]
3g of N4,N4' -di (naphthalene-1-yl) biphenyl-4, 4' -diamine
(6.87 mmol) prepared by Reaction Scheme 1, and 1.62g of 1,3- dibromo-5-methylbenzene (6.87 mmol) were dissolved in toluene, and then, 0.25g of tris (dibenzylidine acetone) dipalladium
(0.27 mmol) was added under a nitrogen atmosphere. Then, 1.65g of sodium butoxide (17.2 mmol) was added to the reaction mixture, and O.llg of (t-bu)3P (0.55 mmol) was fed into a reactor. The reaction mixture was refluxed and agitated for 6 hours. The reaction solution was cooled to room temperature, purified by chromatography on a thin silica pad, and was cleaned by dichloromethane. Next, through an enrichment process, the used solvent was removed. Then, the resultant product was purified through chromatography using 20% dichloromethane/n-hexane solution to obtain 2.5g of a compound
(yield 70%) .
1H-NMR(CDCl3, 300NMR) δ (ppm) 8.03 (d, 4H), 7.61 (d, 4H), 7.46(m, 16H), 7.16 (m, 8H), 6,52(m, 12H), 5.62(s, 4H), 5.47(s, 2H), 2.35(s, 6H)
As shown in FIG. 2, based on the result of the determination of optical and thermal characteristics on the compound m-DBDNBA as prepared above, the maximum absorption wavelength was 346 nm, and the maximum light-emitting
wavelength was 458 nm. In the measurement performed in a THF solution, the energy level of HOMO (highest occupied molecular orbital) was 5.2 eV, and the energy level of LUMO (lowest unoccupied molecular orbital) was 2.0 eV. As a result of thermogravimetric analysis (TGA) , it was determined that the compound is stable even at temperatures higher than 500 °C. [industrial Applicability]
As can be seen from the foregoing, a cyclized aryl amine derivative according to the present invention has high thermal stability because of high glass transition temperature and thermal decomposition temperature. Accordingly, when the cyclized aryl amine derivative is used as a hole transport material of an organic light emitting diode (OLED) having a multilayered structure, it is possible to solve the problem of low brightness and luminous efficiency, which is a main disadvantage of a conventional OLED. Also, since the cyclized aryl amine derivative has high glass transition temperature, it is possible to manufacture an OLED having high thermal stability and advanced efficiency, and to commercialize an OLED device of full natural colors, which requires high efficiency and brightness, and improved lifetime.
Claims
[CLAIMS]
[Claim l]
A cyclized aryl amine derivative represented by Formula 1: [Formula 1]
[Claim 2]
The aryl amine derivative as claimed in claim 1, wherein the cyclized aryl amine derivative represented by Formula 1 is selected from the group including compounds represented by the following structures: 
[Claim 3]
A hole injection layer, which is prepared by the aryl amine derivative as claimed in claim 1 or 2. [Claim 4]
A hole transport layer, which is prepared by the aryl amine derivative as claimed in claim 1 or 2. [Claim 5]
An organic light emitting diode comprising a hole injection layer and/or a hole transport layer being prepared by the aryl amine derivative as claimed in claim 1 or 2.
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| WO2012163480A1 (en) * | 2011-05-27 | 2012-12-06 | Merck Patent Gmbh | Organic electronic device |
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| KR101891773B1 (en) | 2011-10-18 | 2018-08-27 | 삼성디스플레이 주식회사 | Novel heterocyclic compound and organic light emitting device containing same |
| KR20130049075A (en) | 2011-11-03 | 2013-05-13 | 삼성디스플레이 주식회사 | Novel heterocyclic compound and organic light emitting device containing same |
| KR101798009B1 (en) | 2016-09-23 | 2017-11-16 | 재단법인대구경북과학기술원 | Hole Transfer material for Solar Cell and Solar Cell consisting of the Same |
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|---|---|---|---|---|
| JP2004323509A (en) * | 2003-04-07 | 2004-11-18 | Mitsubishi Chemicals Corp | 2,7-diaminonaphthalene compound, electric charge transporting material, material for organic electroluminescent element and the organic electroluminescent element |
| JP2004362930A (en) * | 2003-06-04 | 2004-12-24 | Mitsubishi Chemicals Corp | Organic electroluminescent element, charge transport material, and organic electroluminescent element material |
| JP2005026084A (en) * | 2003-07-02 | 2005-01-27 | Mitsubishi Chemicals Corp | Organic electroluminescent element and manufacturing method of the same |
| US6936189B2 (en) * | 2000-09-28 | 2005-08-30 | Chisso Corporation | Cyclic tertiary amine compound and organic electroluminescent device containing the compound |
-
2006
- 2006-12-28 KR KR1020060136019A patent/KR100808974B1/en not_active IP Right Cessation
-
2007
- 2007-12-28 WO PCT/KR2007/006912 patent/WO2008082164A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6936189B2 (en) * | 2000-09-28 | 2005-08-30 | Chisso Corporation | Cyclic tertiary amine compound and organic electroluminescent device containing the compound |
| JP2004323509A (en) * | 2003-04-07 | 2004-11-18 | Mitsubishi Chemicals Corp | 2,7-diaminonaphthalene compound, electric charge transporting material, material for organic electroluminescent element and the organic electroluminescent element |
| JP2004362930A (en) * | 2003-06-04 | 2004-12-24 | Mitsubishi Chemicals Corp | Organic electroluminescent element, charge transport material, and organic electroluminescent element material |
| JP2005026084A (en) * | 2003-07-02 | 2005-01-27 | Mitsubishi Chemicals Corp | Organic electroluminescent element and manufacturing method of the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012163480A1 (en) * | 2011-05-27 | 2012-12-06 | Merck Patent Gmbh | Organic electronic device |
| CN103563120A (en) * | 2011-05-27 | 2014-02-05 | 默克专利有限公司 | Organic electronic device |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100808974B1 (en) | 2008-03-04 |
| KR20070101752A (en) | 2007-10-17 |
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