WO2008133459A1 - New diamine derivatives and organic electronic device using the same - Google Patents
New diamine derivatives and organic electronic device using the same Download PDFInfo
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- WO2008133459A1 WO2008133459A1 PCT/KR2008/002380 KR2008002380W WO2008133459A1 WO 2008133459 A1 WO2008133459 A1 WO 2008133459A1 KR 2008002380 W KR2008002380 W KR 2008002380W WO 2008133459 A1 WO2008133459 A1 WO 2008133459A1
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- compound
- mmol
- organic
- light emitting
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- 150000004985 diamines Chemical class 0.000 title claims abstract description 29
- 239000011368 organic material Substances 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 125000005264 aryl amine group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000000732 arylene 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
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 238000010030 laminating Methods 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 238000013086 organic photovoltaic Methods 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 61
- 239000002019 doping agent Substances 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 description 180
- 238000002360 preparation method Methods 0.000 description 127
- 239000010410 layer Substances 0.000 description 75
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 238000006243 chemical reaction Methods 0.000 description 43
- 239000012044 organic layer Substances 0.000 description 35
- 239000012299 nitrogen atmosphere Substances 0.000 description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 238000004440 column chromatography 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 20
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- 239000011734 sodium Substances 0.000 description 19
- 229960005235 piperonyl butoxide Drugs 0.000 description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 17
- 239000012153 distilled water Substances 0.000 description 16
- 230000005684 electric field Effects 0.000 description 16
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- 239000011541 reaction mixture Substances 0.000 description 14
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000000151 deposition Methods 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- 239000010409 thin film Substances 0.000 description 9
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- CZYAFTZIQWCKOI-UHFFFAOYSA-N 1,5-dibromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1Br CZYAFTZIQWCKOI-UHFFFAOYSA-N 0.000 description 6
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- -1 arylamine compound Chemical class 0.000 description 6
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- IBGUDZMIAZLJNY-UHFFFAOYSA-N 1,4-dibromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=C(Br)C2=C1 IBGUDZMIAZLJNY-UHFFFAOYSA-N 0.000 description 2
- PJZDEYKZSZWFPX-UHFFFAOYSA-N 2,6-dibromonaphthalene Chemical compound C1=C(Br)C=CC2=CC(Br)=CC=C21 PJZDEYKZSZWFPX-UHFFFAOYSA-N 0.000 description 2
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 2
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- 0 CCCc1ccc*2*cccc12 Chemical compound CCCc1ccc*2*cccc12 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KRBPSCKCVTVUQF-UHFFFAOYSA-N [4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-(1-phenylbenzimidazol-2-yl)methanone Chemical compound C=1C=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=CC=1C(=O)C1=NC2=CC=CC=C2N1C1=CC=CC=C1 KRBPSCKCVTVUQF-UHFFFAOYSA-N 0.000 description 2
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- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
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- 230000007246 mechanism Effects 0.000 description 1
- GWPBTAWWDURSSQ-UHFFFAOYSA-N n-(2,5-dinaphthalen-2-ylphenyl)-9-[4-(2-naphthalen-2-ylanilino)phenyl]carbazol-1-amine Chemical compound C1=CC=CC2=CC(C3=CC=CC=C3NC=3C=CC(=CC=3)N3C4=C(NC=5C(=CC=C(C=5)C=5C=C6C=CC=CC6=CC=5)C=5C=C6C=CC=CC6=CC=5)C=CC=C4C4=CC=CC=C43)=CC=C21 GWPBTAWWDURSSQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- 229920002098 polyfluorene Polymers 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical class 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 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- ZDBNGNFESHFGPV-UHFFFAOYSA-N toluene;tributylphosphane Chemical compound CC1=CC=CC=C1.CCCCP(CCCC)CCCC ZDBNGNFESHFGPV-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07C211/44—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 only one six-membered aromatic ring
- C07C211/49—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 only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—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 only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- 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
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- C07C211/54—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 two or three six-membered aromatic rings
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- 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
- C07C211/61—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 with at least one of the condensed ring systems formed by three or more rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
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- 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
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/30—Germanium compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/50—Pyrenes; Hydrogenated pyrenes
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- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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
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- H—ELECTRICITY
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- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to a new diamine derivative, and an organic electronic device using the same.
- the organic electronic device refers to a device which requires charge exchange between an electrode and an organic material using holes and electrons.
- the organic electronic device can be largely classified into two types according to its operation principle as follows.
- One type is an electronic device having a configuration in which an exciton is formed in an organic material layer by photons flown from an external light source into the device and the exciton is separated into an electron and a hole, the formed electron and hole are transported to a different electrode, respectively and used as a current source (voltage source), and the other type is an electronic device having a configuration in which a hole and/or electron are/is injected into an organic material semiconductor forming an interface with an electrode by applying a voltage or current to two or more electrodes to allow the device to operate by means of the injected electron and hole.
- Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) and an organic transistor, which all require a hole injecting or hole transporting material, an electron injecting or electron transporting material, or a light emitting material for driving the device.
- OPC organic photoconductor
- the organic light emitting device will be mainly and specifically described, but in the above-mentioned organic electronic devices, the hole injecting or hole transporting material, the electron injecting or electron transporting material, or the light emitting material injection functions according to a similar principle.
- the term organic light emitting phenomenon refers to a phenomenon in which electric energy is converted to light energy by means of an organic material.
- the organic light emitting device using the organic light emitting phenomenon has a structure usually comprising an anode, a cathode and an organic material layer interposed therebetween.
- the organic material layer may be mostly formed in a multilayer structure comprising layers of different materials, for example, the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron injecting layer and the like, in order to improve efficiency and stability of the organic light emitting device.
- the organic light emitting device having such a structure, when a voltage is applied between two electrodes, holes from the anode and electrons from a cathode are injected into the organic material layer, the holes and the electrons injected are combined together to form excitons. Further, when the excitons drop to a ground state, lights are emitted.
- Such the organic light emitting device is known to have characteristics such as self- luminescence, high brightness, high efficiency, low drive voltage, wide viewing angle, high contrast and high-speed response.
- the materials used for the organic material layer of the organic light emitting device can be classified into a light emitting material and a charge transporting material, for example, a hole injecting material, a hole transporting material, an electron transporting material and an electron injecting material, according to their functions.
- the light emitting material can be classified into a high molecular weight type and a low molecular weight type, according to their molecular weight, and divided into a fluorescent material from singlet excited states and a phosphorescent material from triplet excited states according to their light emitting mechanism. Further, the light emitting material can be classified into a blue, green or red light emitting material and a yellow or orange light emitting material required for giving more natural color, according to a light emitting color.
- an efficiency of a device is lowered owing to maximum luminescence wavelength moved to a longer wavelength due to the interaction between the molecules, the deterioration of color purity and the reduction in light emitting efficiency when only one material is used for the light emitting material, and therefore a host/dopant system can be used as the light emitting material for the purpose of enhancing the color purity and the light emitting efficiency through energy transfer. It is based on the principle that if a small amount of a dopant having a smaller energy band gap than a host which forms a light emitting layer, excitons which are generated in the light emitting layer are transported to the dopant, thus emitting a light having a high efficiency.
- a material constituting the organic material layer in the device for example, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material should be essentially composed of a stable and efficient material.
- a stable and efficient organic material layer material for the organic light emitting device has not yet been fully realized. Accordingly, the development of new materials is continuously desired. The development of such a material is equally required to the above-mentioned other organic electronic devices. Disclosure of Invention Technical Problem
- the present inventors synthesized a novel diamine derivative, and further found that the diamine derivative can be used as a hole injecting, hole transporting, electron injecting, electron transporting or light emitting material, in particular, a light emitting dopant in light emitting layer, and exhibit effects of increased efficiency, lower operating voltage, increased life-time, and higher stability of an organic electronic device, thereby completing the present invention.
- the present invention provides a diamine derivative, represented by the following
- Ll and L2 are same or different from each other, and are each independently a direct bond; a C ⁇ C arylene group unsubstituted or substituted with one or more
- ArI, Ar2, Ar3and Ar4 are same or different from each other, and are each independently hydrogen, a C ⁇ C aryl group unsubstituted or sunstituted with halogen,
- ⁇ C cycloaliyl group -OR, -SR, -SeR, -TeR, -BRR', -AlRR', -SRR'R", -GeRR 1 R", or -SnRR 1 R"; a C ⁇ C heterocyclic group comprising O, N or S; or a condensed ring
- R 4 20 6 20 and R" are same or different from each other, and are each independently hydrogen, a C - C alkyl group, a C ⁇ C cycloalkyl group, a C ⁇ C aryl group or a C ⁇ C
- the diamine derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material in an organic electronic device including an organic light emitting device. Particularly, it can serve as a light emitting dopant as used alone, in particular, a blue light emitting dopant.
- the organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, drive voltage, life time, and stability.
- FIG. 1 illustrates the structure of the organic light emitting device according to one embodiment of the present invention. Best Mode for Carrying Out the Invention
- the present invention provides a diamine derivative, represented by Formula 1.
- the diamine derivative represented by Formula 1 is preferably represented by any one of the following Formulae 2 to 6. [24] [Formula 2]
- Ll, L2, ArI, Ar2, Ar3 and Ar4 are the same as defined in Formula 1.
- Ll and L2 may be same or different from each other, and are each independently a direct bond, or selected from the group consisting of a phenylene group and a naphthylene group, but are not limited thereto.
- ArI and Ar3 may be same or different from each other, and are each independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a phenyl group substituted with -SRR'R" or -GeRR 1 R", but are not limited thereto, wherein R, R', and R" may be same or different from each other, and are each independently hydrogen, a C ⁇ C alfed group, a C ⁇ C cycloalfed
- Ar2 and Ar4 may be same or different from each other, and are each independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a pherylenyl group, a phenyl group substituted with -SRR'R" or -GeRR 1 R", a C ⁇ C heterocyclic group
- R, R', and R" may be same or different from each other, and are each independently hydrogen, a C ⁇ C alfyl group, a C ⁇ C cycloalfyl group, a C 6 ⁇ C 20 aryl group or a C 5 ⁇ C 20 heterocyclic g c rou-p i .
- Ll, L2, ArI, Ar2, Ar3 and Ar4 in Formulae 1 to 6 are illustrated in the following Table 1, but are not limited thereto.
- the present invention provides a method for preparing the diamine derivative represented by Formula 1.
- the diamine derivative according to the present invention can be prepared by reacting a dibromoaryl compound with an arylamine compound in the presence of a palladium catalyst. A specific preparation method will be described in the following Preparation Examples.
- the present invention provides an organic electronic device comprising the diamine derivative represented by Formula 1.
- the diamine derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material in an organic electronic device including an organic light emitting device. Particularly, it can serve as a light emitting dopant as used alone, in particular, a blue light emitting dopant.
- the organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, drive voltage, life time, and stability.
- the organic electronic device of the present invention can be prepared by usual methods and materials for preparing an organic electronic device, except that the above-described compounds are used to form at least one organic material layer.
- the organic light emitting device will be exemplified.
- the above-described compounds can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material, and particularly serve as a light emitting material as used alone, as well as a light emitting host with an appropriate light emitting dopant or a light emitting dopant with an appropriate light emitting host.
- the organic light emitting device may have a structure that comprises a first electrode, a second electrode and organic material layers interposed therebetween, and can be prepared by usual methods and materials for preparing an organic light emitting device, except that the above- described compound according to the present invention is used to form at least one of the organic material layers in an organic light emitting device.
- the structure of the organic light emitting device according to the present invention is shown in FIG. 1.
- the organic light emitting device can be prepared by depositing a metal, a metal oxide having conductivity or an alloy thereof on a substrate using a PVD (physical vapor deposition) process such as sputtering and e-beam evaporation to form an anode; forming an organic material layer comprising a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the anode; and depositing a material, which can be used as a cathode, thereon.
- the organic light emitting device can be prepared by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
- the organic material layer may be of a multilayer structure containing a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and the like, but not limited thereto, and may be of a monolayer structure. Further, the organic material layer can be produced to have a fewer number of layers, by using a variety of polymeric materials, by means of a solvent process rather than a deposit process, such as spin coating, dip coating, doctor blading, screen printing, ink jet printing, and heat transfer processes.
- the anode material is preferably a material having a large work function to facilitate hole injection usually to an organic material layer.
- Specific examples of the anode material which can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold, or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium- tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al and SnO :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene- 1 ,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto.
- the cathode material is preferably a material having a small work function to facilitate electron injection usually to an organic material layer.
- Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or an alloy thereof; multilayer structure materials such as IiF/ Al and IiO 2 /Al, but not limited thereto.
- the hole injecting material is a material facilitating hole injection from an anode at low voltage.
- the HOMO (highest occupied molecular orbital) level of the hole injecting material is preferably located between the work function of the anode materials and the HOMO level of its neighboring organic material layer.
- Specific examples of the hole injecting material include metal porphyrin, oligothiophene, organic materials of arylamine series, hexanitrile hexaazatriphenylene, organic materials of qiinacridone series, organic materials of perylene series, anthraqiinone, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.
- the hole transporting material is preferably a material having high hole mobility, which can transfer holes from the anode or the hole injecting layer toward the light emitting layer.
- Specific examples thereof include organic materials of arylamine series, conductive polymers and block copolymers having both conjugated portions and non- conjugated portions, but are not limited thereto.
- the light emitting material are a material capable of emitting visible light by accepting and recombining holes from the hole transporting layer and electrons from the electron transporting layer, preferably a material having high quantum efficiency for fluorescence and phosphorescence.
- Specific examples thereof include 8 -hydroxy qiinoline aluminum complex (AIq ); compounds of carbazole series; dimerized styryl compounds; BAIq; 10-hydroxybenzoquinoline-metal compounds; compounds of benzoxazole, benzthiazole and benzimidazole series; polymers of poly(p-phenylenevinylene) (PPV) series; spiro compounds; and compounds of polyfluorene and rubrene series, but are not limited thereto.
- AIq 8 -hydroxy qiinoline aluminum complex
- PV poly(p-phenylenevinylene) series
- spiro compounds and compounds of polyfluorene and rubrene series, but are not limited thereto.
- the electron transporting material is suitably a material having high electron mobility, which can transfer electrons from the cathode to the light emitting layer.
- a material having high electron mobility which can transfer electrons from the cathode to the light emitting layer.
- Specific examples thereof include 8 -hydroxy qiinoline aluminum complex; complexes including AIq ; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited thereto.
- the organic light emitting device according to the present invention may be of a front-side, backside or double-sided light emission according to the materials used.
- the compound according to the present invention can function in an organic electronic device including an organic solar cell, an organic photoconductor and an organic transistor, according to a principle similar to that applied to the organic light emitting device.
- the compound of Formula 1 according to the present invention can be prepared in multi-step chemical reactions.
- the preparation of the compound is described by way of Examples below.
- a certain intermediate compound is first prepared, and then the intermediate compound is used to prepare the compound of Formula 1.
- Exemplary intermediate compounds are listed below as Compounds A through Y. In these compounds, Br or Cl may be substituted with any other reactive atoms or functional groups.
- the organic layer was extracted with THF, dried over magnesium sulfate, and then filtered under reduced pressure. The filtrate was concentrated to remove the solvent, and the resultant was dissolved in THF. An excessive amount of aqueous solution was added thereto, and the organic layer was separated with dimethylchloromethane. A hydrochloric acid aqueous solution was added to the separated aqueous layer, precipitated, filtered to obtain a compound (2.7 g, 42%).
- a Compound 3-52 (3.64 g, 60%) was obtained in the same manner as in Example 4, except that the compound F (3.07 g, 8.5 mmol) prepared in Preparation Example 6 was used instead of compound B (3.07 g, 8.5mmol) prepared in Preparation Example 2 in Example 4.
- a Compound 4-52 (3.64 g, 60%) was obtained in the same manner as in Example 4, except that the compound D (3.07 g, 8.5 mmol) prepared in Preparation Example 4 was used instead of compound B (3.07 g, 8.5mmol) prepared in Preparation Example 2 in Example 4.
- a Compound 2-64 (4.5 g, 62%) was obtained in the same manner as in Example 3, except that the compound B (3.07 g, 8.5 mmol) prepared in Preparation Example 2 was used instead of compound A (2.43 g, 8.5 mmol) prepared in Preparation Example 1 in Example 3.
- a Compound 2-68 (4.01 g, 60%) was obtained in the same manner as in Example 3, except that the compound T (6.CB g, 20.4 mmol) prepared in Preparation Example 20 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 4.
- a Compound 2-70 (3.77 g, 50%) was obtained in the same manner as in Example 4, except that the compound U (7.00 g, 20.4 mmol) prepared in Preparation Example 21 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 4.
- a Compound 3-78 (3.64 g, 60%) was obtained in the same manner as in Example 10, except that the compound F (3.07 g, 8.5 mmol) prepared in Preparation Example 6 was used instead of compound B (3.07 g, 8.5 mmol) prepared in Preparation Example 2 in Example 10.
- a Compound 4-78 (3.64 g, 60%) was obtained in the same manner as in Example 10, except that the compound D (3.07 g, 8.5 mmol) prepared in Preparation Example 4 was used instead of compound B (3.07 g, 8.5 mmol) prepared in Preparation Example 2 in Example 10.
- a glass substrate (Corning 7059 glass), on which a thin film of ITO (indium tin oxide) was coated to a thickness of 1,000 A, was immersed in distilled water having a detergent dissolved therein to wash the substrate with ultrasonic waves.
- the detergent as used herein was a product commercially available from Fisher Co. and the distilled water was one which had been twice filtered by using a filter commercially available from Millipore Co.
- ITO was washed for 30 minutes, and then washing with ultrasonic waves was repeated twice for 10 minutes by using distilled water. After the completion of washing with distilled water, washing with ultrasonic waves was carried out by using solvents such as isopropyl alcohol, acetone and methanol.
- solvents such as isopropyl alcohol, acetone and methanol.
- the resultant product was dried, and then transported to a plasma washing machine.
- the substrate was washed for 5 minutes using an oxygen plasma, and then transported to a vacuum depositing machine.
- the compound 2-1 prepared in Example 1 (2 wt%) was deposited thereon with the following compound Z (300 A) to form a light emitting layer, and then 9,10-bis-2-naphthyl-2-[4-(N-phenylbenzoimidazoyl)phenyl]anthracene (300 A) was coated by thermal vacuum deposition to form an electron transporting layer.
- lithium fluoride pF) and aluminum were sequentially deposited on the electron transporting layer to thicknesses of 12 A and 2,000 A, respectively, to form a cathode, thereby obtaining an organic light emitting device.
- HAT hexanitrile hexaazatriphenylene
- the compound 2-52 (400 A) prepared in Example 4 was vacuum- deposited to form a hole transporting layer.
- AIq was vacuum-deposited to a thickness of 300 A, thus to form a light emitting layer.
- the electron transporting layer material of the following Formula was deposited to a thickness of 200 A, thus to form an electron transporting layer.
- lithium fluoride pF lithium fluoride pF
- aluminum were sequentially vacuum-deposited to a thickness of 12 A and 2,000 A, respectively, to form a cathode.
- the diamine derivative according to the present invention was found to exhibit effects of lower operating voltage and increased efficiency of an organic electronic device.
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Abstract
The present invention relates to a new diamine derivative, and an organic electronic device using the same. The diamine derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material in an organic electronic device including an organic light emitting device. Particularly, it can serve as a light emitting dopant as used alone, in particular, a blue light emitting dopant. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, drive voltage, life time, and stability.
Description
Description
NEW DIAMINE DERIVATIVES AND ORGANIC ELECTRONIC DEVICE USING THE SAME
Technical Field
[1] The present invention relates to a new diamine derivative, and an organic electronic device using the same.
[2] This application claims priority benefits from Korean Patent Application No.
10-2007 -0040965, filed on April 26, 2007, the entire contents of which are fully incorporated herein by reference. Background Art
[3] The organic electronic device refers to a device which requires charge exchange between an electrode and an organic material using holes and electrons. The organic electronic device can be largely classified into two types according to its operation principle as follows. One type is an electronic device having a configuration in which an exciton is formed in an organic material layer by photons flown from an external light source into the device and the exciton is separated into an electron and a hole, the formed electron and hole are transported to a different electrode, respectively and used as a current source (voltage source), and the other type is an electronic device having a configuration in which a hole and/or electron are/is injected into an organic material semiconductor forming an interface with an electrode by applying a voltage or current to two or more electrodes to allow the device to operate by means of the injected electron and hole.
[4] Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) and an organic transistor, which all require a hole injecting or hole transporting material, an electron injecting or electron transporting material, or a light emitting material for driving the device.
[5] Hereinafter, the organic light emitting device will be mainly and specifically described, but in the above-mentioned organic electronic devices, the hole injecting or hole transporting material, the electron injecting or electron transporting material, or the light emitting material injection functions according to a similar principle.
[6] In general, the term organic light emitting phenomenon refers to a phenomenon in which electric energy is converted to light energy by means of an organic material. The organic light emitting device using the organic light emitting phenomenon has a structure usually comprising an anode, a cathode and an organic material layer
interposed therebetween. Herein, the organic material layer may be mostly formed in a multilayer structure comprising layers of different materials, for example, the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron injecting layer and the like, in order to improve efficiency and stability of the organic light emitting device. In the organic light emitting device having such a structure, when a voltage is applied between two electrodes, holes from the anode and electrons from a cathode are injected into the organic material layer, the holes and the electrons injected are combined together to form excitons. Further, when the excitons drop to a ground state, lights are emitted. Such the organic light emitting device is known to have characteristics such as self- luminescence, high brightness, high efficiency, low drive voltage, wide viewing angle, high contrast and high-speed response.
[7] The materials used for the organic material layer of the organic light emitting device can be classified into a light emitting material and a charge transporting material, for example, a hole injecting material, a hole transporting material, an electron transporting material and an electron injecting material, according to their functions. The light emitting material can be classified into a high molecular weight type and a low molecular weight type, according to their molecular weight, and divided into a fluorescent material from singlet excited states and a phosphorescent material from triplet excited states according to their light emitting mechanism. Further, the light emitting material can be classified into a blue, green or red light emitting material and a yellow or orange light emitting material required for giving more natural color, according to a light emitting color.
[8] On the other hand, an efficiency of a device is lowered owing to maximum luminescence wavelength moved to a longer wavelength due to the interaction between the molecules, the deterioration of color purity and the reduction in light emitting efficiency when only one material is used for the light emitting material, and therefore a host/dopant system can be used as the light emitting material for the purpose of enhancing the color purity and the light emitting efficiency through energy transfer. It is based on the principle that if a small amount of a dopant having a smaller energy band gap than a host which forms a light emitting layer, excitons which are generated in the light emitting layer are transported to the dopant, thus emitting a light having a high efficiency. Here, since the wavelength of the host is moved according to the wavelength of the dopant, a light having a desired wavelength can be obtained according the kind of the dopant.
[9] In order to allow the organic light emitting device to fully exhibit the above- mentioned excellent characteristics, a material constituting the organic material layer in the device, for example, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material should be essentially composed of a stable and efficient material. However, the development of a stable and efficient organic material layer material for the organic light emitting device has not yet been fully realized. Accordingly, the development of new materials is continuously desired. The development of such a material is equally required to the above-mentioned other organic electronic devices. Disclosure of Invention Technical Problem
[10] Accordingly, the present inventors synthesized a novel diamine derivative, and further found that the diamine derivative can be used as a hole injecting, hole transporting, electron injecting, electron transporting or light emitting material, in particular, a light emitting dopant in light emitting layer, and exhibit effects of increased efficiency, lower operating voltage, increased life-time, and higher stability of an organic electronic device, thereby completing the present invention.
[11] It is an object of the present invention to provide a novel diamine derivative.
[12] Further, it is another object of the present invention to provide a method for preparing a novel diamine derivative.
[13] Further, it is still another object of the present invention to provide an organic electronic device comprising the diamine derivative. Technical Solution
[14] The present invention provides a diamine derivative, represented by the following
Formula 1.
[15] [Formula 1]
[17] wherein Ll and L2 are same or different from each other, and are each independently a direct bond; a C ~ C arylene group unsubstituted or substituted with one or more
6 20 groups selected from the group consisting of a C ~ C ahtyl group, a C ~ C alkenyl
1 20 2 20 group, a C 2 ~ C 20 ahtynyl group, a C 3 ~ C 20 cycloahty ./ l goroujp-, a C 2 ~ C 20 hetero- cycloahtyl group, a C 6 ~ C 20 aryl group and a C 5 ~ C 20 heteroary ./ l gorou-pL ; or a C 5 ~ C 20
heteroarylene group unsubstituted or substituted with one or more groups selected from the group consisting of a C ~ C alfyl group, a C ~ C alkenyl group, a C ~ C
20 alkynyl group, a C 3 ~ C 20 cycloalk Jyl g orou rp, a C 2 ~ C 20 heterocycloallw J l g orou rp, a C 6 ~
C aryl group and a C ~ C heteroaryl group; and
20 5 20
[18] ArI, Ar2, Ar3and Ar4 are same or different from each other, and are each independently hydrogen, a C ~ C aryl group unsubstituted or sunstituted with halogen,
6 30
CN, NO , a C ~ C aliyl group, a C ~ C alktxy group, a C ~ C aryl group, a C ~
2 1 20 1 20 6 20 5
C heteroaryl group, a C ~ C aryl amine group, a C ~ C aryl thiophene group, a C
20 6 20 6 20 3
~ C cycloaliyl group, -OR, -SR, -SeR, -TeR, -BRR', -AlRR', -SRR'R", -GeRR1R", or -SnRR1R"; a C ~ C heterocyclic group comprising O, N or S; or a condensed ring
5 20 formed by fusing a C ~ C alfedene group with a C ~ C aryl group, wherein R, R'
4 20 6 20 and R" are same or different from each other, and are each independently hydrogen, a C - C alkyl group, a C ~ C cycloalkyl group, a C ~ C aryl group or a C ~ C
1 20 3 20 J o r 6 20 5 20 heterocyclic group.
Advantageous Effects
[19] The diamine derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material in an organic electronic device including an organic light emitting device. Particularly, it can serve as a light emitting dopant as used alone, in particular, a blue light emitting dopant. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, drive voltage, life time, and stability.
Brief Description of the Drawings
[20] FIG. 1 illustrates the structure of the organic light emitting device according to one embodiment of the present invention. Best Mode for Carrying Out the Invention
[21] Hereinafter, the present invention will be described in detail.
[22] The present invention provides a diamine derivative, represented by Formula 1.
[23] The diamine derivative represented by Formula 1 is preferably represented by any one of the following Formulae 2 to 6. [24] [Formula 2]
[34] wherein Ll, L2, ArI, Ar2, Ar3 and Ar4 are the same as defined in Formula 1. [35] wherein Ll and L2 may be same or different from each other, and are each independently a direct bond, or selected from the group consisting of a phenylene group
and a naphthylene group, but are not limited thereto.
[36] wherein ArI and Ar3 may be same or different from each other, and are each independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a phenyl group substituted with -SRR'R" or -GeRR1R", but are not limited thereto, wherein R, R', and R" may be same or different from each other, and are each independently hydrogen, a C ~ C alfed group, a C ~ C cycloalfed
1 20 3 20 group, a C ~ C aryl group or a C ~ C heterocyclic group.
6 20 5 20
[37] wherein Ar2 and Ar4 may be same or different from each other, and are each independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a pherylenyl group, a phenyl group substituted with -SRR'R" or -GeRR1R", a C ~ C heterocyclic group
5 20 comprising S, a C ~ C aryl amine group, and a C ~ C aryl group, but are not
6 20 6 20 limited thereto, wherein R, R', and R" may be same or different from each other, and are each independently hydrogen, a C ~ C alfyl group, a C ~ C cycloalfyl group, a C 6 ~C 20 aryl group or a C 5 ~ C 20 heterocyclic g crou-pi .
[38] Preferred examples of Ll, L2, ArI, Ar2, Ar3 and Ar4 in Formulae 1 to 6 are illustrated in the following Table 1, but are not limited thereto.
[39] A variety of derivatives may be prepared in combination of the compounds of
Formulae 2 to 6 and the groups illustrated in the following Table 1. For example, a compound prepared by Formula 2 and a group 1 of the following Table 1 is designated as compound 2-1.
[40] [Table 1]
[41]
[47]
[63]
[72]
[74]
[S)] Further, the present invention provides a method for preparing the diamine derivative represented by Formula 1. [81] The diamine derivative according to the present invention can be prepared by reacting a dibromoaryl compound with an arylamine compound in the presence of a palladium catalyst. A specific preparation method will be described in the following Preparation Examples.
[82] Further, the present invention provides an organic electronic device comprising the diamine derivative represented by Formula 1. [83] The diamine derivative according to the present invention can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material in an organic electronic device including an organic light emitting device. Particularly, it can serve as a light emitting dopant as used alone, in particular, a blue light emitting dopant. The organic electronic device according to the present invention exhibits excellent characteristics in terms of efficiency, drive voltage, life time, and stability.
[84] The organic electronic device of the present invention can be prepared by usual methods and materials for preparing an organic electronic device, except that the above-described compounds are used to form at least one organic material layer.
[85] Hereinbelow, the organic light emitting device will be exemplified. [86] The above-described compounds can serve as a hole injecting, hole transporting, electron injecting, electron transporting, or light emitting material, and particularly serve as a light emitting material as used alone, as well as a light emitting host with an appropriate light emitting dopant or a light emitting dopant with an appropriate light emitting host.
[87] In one embodiment of the present invention, the organic light emitting device may have a structure that comprises a first electrode, a second electrode and organic material layers interposed therebetween, and can be prepared by usual methods and materials for preparing an organic light emitting device, except that the above- described compound according to the present invention is used to form at least one of the organic material layers in an organic light emitting device. The structure of the organic light emitting device according to the present invention is shown in FIG. 1.
[88] For example, the organic light emitting device according to the present invention can be prepared by depositing a metal, a metal oxide having conductivity or an alloy thereof on a substrate using a PVD (physical vapor deposition) process such as sputtering and e-beam evaporation to form an anode; forming an organic material layer comprising a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the anode; and depositing a material, which can be used as a cathode, thereon. Alternatively, the organic light emitting device can be prepared by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
[89] The organic material layer may be of a multilayer structure containing a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and the like, but not limited thereto, and may be of a monolayer structure. Further, the organic material layer can be produced to have a fewer number of layers, by using a variety of polymeric materials, by means of a solvent process rather than a deposit process, such as spin coating, dip coating, doctor blading, screen printing, ink jet printing, and heat transfer processes.
[90] The anode material is preferably a material having a large work function to facilitate hole injection usually to an organic material layer. Specific examples of the anode material which can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold, or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium- tin oxide (ITO), and indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO:Al and SnO :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene- 1 ,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but not limited thereto.
[91] The cathode material is preferably a material having a small work function to facilitate electron injection usually to an organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or an
alloy thereof; multilayer structure materials such as IiF/ Al and IiO 2 /Al, but not limited thereto.
[92] The hole injecting material is a material facilitating hole injection from an anode at low voltage. The HOMO (highest occupied molecular orbital) level of the hole injecting material is preferably located between the work function of the anode materials and the HOMO level of its neighboring organic material layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, organic materials of arylamine series, hexanitrile hexaazatriphenylene, organic materials of qiinacridone series, organic materials of perylene series, anthraqiinone, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.
[93] The hole transporting material is preferably a material having high hole mobility, which can transfer holes from the anode or the hole injecting layer toward the light emitting layer. Specific examples thereof include organic materials of arylamine series, conductive polymers and block copolymers having both conjugated portions and non- conjugated portions, but are not limited thereto.
[94] The light emitting material are a material capable of emitting visible light by accepting and recombining holes from the hole transporting layer and electrons from the electron transporting layer, preferably a material having high quantum efficiency for fluorescence and phosphorescence. Specific examples thereof include 8 -hydroxy qiinoline aluminum complex (AIq ); compounds of carbazole series; dimerized styryl compounds; BAIq; 10-hydroxybenzoquinoline-metal compounds; compounds of benzoxazole, benzthiazole and benzimidazole series; polymers of poly(p-phenylenevinylene) (PPV) series; spiro compounds; and compounds of polyfluorene and rubrene series, but are not limited thereto.
[95] The electron transporting material is suitably a material having high electron mobility, which can transfer electrons from the cathode to the light emitting layer. Specific examples thereof include 8 -hydroxy qiinoline aluminum complex; complexes including AIq ; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited thereto.
[96] The organic light emitting device according to the present invention may be of a front-side, backside or double-sided light emission according to the materials used.
[97] The compound according to the present invention can function in an organic electronic device including an organic solar cell, an organic photoconductor and an organic transistor, according to a principle similar to that applied to the organic light
emitting device.
Mode for the Invention
[98] Hereinbelow, the preferred Examples of the present invention will be presented for further understanding the present invention. However, the following Examples are presented merely for illustrative purpose, and thus do not limit the scope of the present invention.
[99] The compound of Formula 1 according to the present invention can be prepared in multi-step chemical reactions. The preparation of the compound is described by way of Examples below. As will be clear in Examples, a certain intermediate compound is first prepared, and then the intermediate compound is used to prepare the compound of Formula 1. Exemplary intermediate compounds are listed below as Compounds A through Y. In these compounds, Br or Cl may be substituted with any other reactive atoms or functional groups.
[100]
[101]
[102] <Preparation Example 1> Preparation of Compound A
[103] Under cooling conditions, 1,5-diaminonaphthalene (12 g, 75.9 mmol) was dissolved in H O (30OmL) and concentrated sulfuric acid (20 niL). NaNO dissolved in H O (300
2 2 2 rnL) was slowly added dropwise, and then stirred at O0C for 45 min. The reaction mixture was filtered, and then CuBr (30 g, 52.3 mmol), HBr (48%, 450 mL), and H O
2 2
(450 mL) were added to the filtrate. The reaction solution was stirred at O0C for 1 hr and at room temperature for 2 hrs, and then stirred again at 7O0C for 30 min. The reaction solution was separated using benzene. The organic layer was dried over sodium sulfate, and then distilled under reduced pressure. The residue was purified by column chromatography to obtain a compound A (5.9 g, 27%). [104] MS: [M] = 286.
[105] <Preparation Example 2> Preparation of Compound B [106] Under N atmosphere, 1,5-dibromonaphthalene (5 g, 17.5 mmol),
2
4-bromophenylboronic acid (3.5 g, 17.5 mmol), and Pd(PPh ) (1.0 g, 0.88 mmol) were
3 4
added to a 2 M K CO aqueous solution (10 niL) and THF (tetrahydrofuran, 200 niL),
2 3 and refluxed under stirring for about 24 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture. The organic layer was dried over magnesium sulfate, and then distilled under reduced pressure. The residue was purified by column chromatography to obtain a compound B (3.16 g, 50%). [107] MS: [M] = 362.
[ICB] <Preparation Example 3> Preparation of Compound C [109] Under N atmosphere, 1,5-dibromonaphthalene (5 g, 17.5 mmol),
4-chlorophenylboronic acid (6.6 g, 42.0 mmol), and Pd(PPh ) (1.0 g, 0.87 mmol) were
3 4 added to a 2 M K CO aqueous solution (20 mL) and THF (tetrahydrofuran, 200 mL),
2 3 and refluxed under stirring for about 24 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture. The organic layer was dried over magnesium sulfate, and then distilled under reduced pressure. The residue was purified with THF/EtOH to obtain a compound C (5.9 g, 97%). [110] MS: [M+H]+ = 348.
[I l l] <Preparation Example 4> Preparation of Compound D [112] A compound D (3.16 g, 50%) was prepared in the same manner as in Preparation
Example 2, except that 1.4-dibromonaphthalene (5 g, 17.5 mmol) was used instead of 1,5-dibromonaphthalene (5 g, 17.5 mmol) in Preparation Example 2. [113] MS: [M] = 362.
[114] <Preparation Example 5> Preparation of Compound E [115] A compound E (5.9 g, 97%) was prepared in the same manner as in Preparation
Example 3, except that 1.4-dibromonaphthalene (5 g, 17.5 mmol) was used instead of 1,5-dibromonaphthalene (5 g, 17.5 mmol) in Preparation Example 3. [116] MS: [M] = 348.
[117] <Preparation Example 6> Preparation of Compound F [118] A compound F (3.16 g, 50%) was prepared in the same manner as in Preparation
Example 2, except that 2.6-dibromonaphthalene (5 g, 17.5 mmol) was used instead of 1,5-dibromonaphthalene (5 g, 17.5 mmol) in Preparation Example 2. [119] MS: [M] = 362.
[120] <Preparation Example 7> Preparation of Compound G [121] A compound G (5.9 g, 97%) was prepared in the same manner as in Preparation
Example 3, except that 2.6-dibromonaphthalene (5 g, 17.5 mmol) was used instead of
1,5-dibromonaphthalene (5 g, 17.5 mmol) in Preparation Example 3. [122] MS: [M] = 348. [123] <Preparation Example 8> Preparation of Compound H
[124] 2-Thiophene boronic acid (10 g, 78.1 mmol) and bromo benzene (7.48 mL, 70.3 mmol) were dissolved in anhydrous THF (300 mL), and then Pd(PPh ) (4.51 g, 3.91
3 4 mmol) and a K CO aqueous solution (156 mL, 312.4 mmol) were added thereto,
2 3 refluxed for 3 hrs. The organic layer was extracted with ethyl acetate, and dried over magnesium sulfate. The organic layer was filtered under reduced pressure, and concentrated to remove the solvent. The residue was purified by column chromatography, and then recrystallized in THF and ethanol to obtain a white solid compound (1O g, 83%).
[125] MS: [M+H] = 161.
[126] The prepared white solid compound (5 g, 31.3 mmol) were dissolved in anhydrous THF (200 mL), and then cooled to -1O0C. Then, n-butyllithium (15 mL, 37.5 mmol) was slowly added dropwise, and stirred for 1 hr. Subsequently, the reaction temperature was decreased to -780C, and then boronic acid trimethylester (10.5 mL, 93.75 mmol) was slowly added, stirred for 12 hrs. After the temperature was decreased to O0C, a 2 N hydrochloric acid aqueous solution (16 mL) was added thereto, and stirred to obtain a white precipitate. The organic layer was extracted with THF, dried over magnesium sulfate, and then filtered under reduced pressure. The filtrate was concentrated to remove the solvent, and the resultant was dissolved in THF. An excessive amount of aqueous solution was added thereto, and the organic layer was separated with dimethylchloromethane. A hydrochloric acid aqueous solution was added to the separated aqueous layer, precipitated, filtered to obtain a compound (2.7 g, 42%).
[127] 3-Bromoiodobenzene (3.5 g, 12.3 mmol) and the above prepared compound (2.5 g, 12.3 mmol) were dissolved in anhydrous THF (100 mL), and Pd(PPh ) (0.71 g, 0.61 mmol) were added thereto. K CO (3.4 g, 24.6 mmol) dissolved in H O (50 mL) was added thereto, and then refluxed under stirring. After 3 hrs, the resultant was washed with brine, and the organic layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered under reduced pressure, and concentrated to remove the solvent. The residue was purified by column chromatography to obtain a compound H (2.9 g, 75%).
[128] MS: [M+H]+ = 315.
[129] <Preparation Example 9> Preparation of Compound I
[130] Aniline (10 ml, 109.74 mmol) and the compound H prepared in Preparation Example
8 (34.5 g, 109.7 mmol) were dissolved in 300 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 1.26 g, 2.20 mmol), 50 wt% of tή-t -butylphosphine (1.30 ml, 3.29 mmol) and sodium ?-butoxide (21.09 g, 219.5 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound I (15 g, yield 56%). [131] MS: [M+H]+ = 327.
[132] <Preparation Example 10> Preparation of Compound J [133] Under nitrogen atmosphere, aniline (10 ml, 109.74 mmol) and 4-bromo biphenyl (25.6 g, 109.7 mmol) were dissolved in 300 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 1.26 g, 2.20 mmol), 50 wt% of tή-t -butylphosphine (1.30 ml, 3.29 mmol) and sodium ?-butoxide (21.09 g, 219.5 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound J (15 g, yield 56%).
[134] MS: [M+H]+ = 245.
[135] <Preparation Example 11> Preparation of Compound K [136] 1-Aminonaphthalene (7.4 g, 51.48 mmol) and 4-bromobiphenyl (12 g, 51.48 mmol) were dissolved in 200 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 0.89 g, 1.54 mmol), 50 wt% of tri-?-butylphosphine (0.60 ml, 1.54 mmol) and sodium ?-butoxide (9.90 g, 103.0 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (15/1), stirred in pet. Ether, and dried under vacuum to obtain a compound K (6.3 g, yield 42%). [137] MS: [M+H]+ = 295.
[138] <Preparation Example 12> Preparation of Compound L [139] Under nitrogen atmosphere, 4.18 g of N,N-diphenylamine (24.7 mmol) and 4.72 g of l-bromo-4-chlorophenyl (24.7 mmol) were dissolved in 200 ml of toluene. Then, 5.94 g of sodium ?-butoxide (61.8 mmol), 0.43 g of bis(dibenzylidene-acetone)palladium (0) (0.74 mmol), and 0.61 ml of 50 wt% tri-?-butylphosphine (1.24 mmol) were added thereto, and refluxed under nitrogen atmosphere for 5 hrs. Distilled water was added to
the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound L (2.9 g, yield 42%).
[140] MS: [M+H] += 279.
[141] <Preparation Example 13> Preparation of Compound M
[142] 4-aminobiphenyl (30.5 g, 183.17 mmol) and 4-bromo biphenyl (40 g, 171.59 mmol) were dissolved in 500 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 2.07 g, 3.60 mmol), 50 wt% of tri- t-butylphosphine (2.2 ml, 5.41 mmol) and sodium ?-butoxide (51.94 g, 540.5 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (15/1), stirred in pet. Ether, and dried under vacuum to obtain a compound M (32 g, yield 58%).
[143] MS: [M+H]+ = 321.
[144] <Preparation Example 14> Preparation of Compound N
[145] Aniline (10 ml, 109.74 mmol) and the compound L prepared in Preparation Example 12 (30.7 g, 109.7 mmol) were dissolved in 300 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 1.26 g, 2.20 mmol), 50 wt% of tri-? -butylphosphine (1.30 ml, 3.29 mmol) and sodium ?-butoxide (21.09 g, 219.5 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound N (15 g, yield 56%).
[146] MS: [M+H]+ = 336.
[147] <Preparation Example 15> Preparation of Compound O
[148] Dibromobenzene (20 g, 84.78 mmol) was dried under nitrogen atmosphere at room temperature, and dissolved in THF (200 mL). The solution was cooled to -780C. n- Butyl lithium (34 mL, 2.5 M pentane solution) were slowly added to the solution at - 780C, and the temperature of the mixture was raised to O0C for about 1 hr. Trimethyl- germanium bromide (18 ml, 101.74 mmol) was added thereto, and the temperature was raised to room temperature for 1 hr. After completion of the reaction, the mixture was extracted with ethyl acetate, and then dried over magnesium sulfate. The residue was distilled under reduced pressure to obtain a compound O (20 g, 90%).
[149] MS: (M+) = 273.
[150] <Preparation Example 16> Preparation of Compound P
[151] Under nitrogen atmosphere, the compound O (18 g, 65.45 mmol), aniline (6.6 ml, 72 mmol), Pd(dba) (0.125 g, 0.13 mmol), P(t-Bu) (0.04 g, 0.2 mmol) and sodium t -
2 3 butoxide (1.8O g, 18.7 mmol) were added to toluene (200 mL), and refluxed for about 3 hrs. After completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixture of THF and H O. The organic layer was
2 separated, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography to obtain a compound P (16 g, 85%). [152] MS: [M] = 286.
[153] <Preparation Example 17> Preparation of Compound Q [154] Dibromobenzene (20 g, 84.78 mmol) was dried under nitrogen atmosphere at room temperature, and dissolved in THF (200 mL). The solution was cooled to -780C. n- Butyl lithium (34 mL, 2.5 M pentane solution) were slowly added to the solution at - 780C, and the temperature of the mixture was raised to O0C for about 1 hr. Chloro trimethylsilane (13 ml, 101.74 mmol) was added thereto, and the temperature was raised to room temperature for 1 hr. After completion of the reaction, the mixture was extracted with ethyl acetate, and then dried over magnesium sulfate. The residue was distilled under reduced pressure to obtain a compound Q (18 g, 93%). [155] MS: (M+) = 229.
[156] <Preparation Example 18> Preparation of Compound R [157] Under nitrogen atmosphere, the compound Q (15 g, 65.45 mmol), aniline (6.6 ml, 72 mmol), Pd(dba) (0.125 g, 0.13 mmol), P(t-Bu) (0.04 g, 0.2 mmol) and sodium t - butoxide (1.8O g, 18.7 mmol) were added to toluene (200 mL), and refluxed for about 3 hrs. After completion of the reaction, the reaction mixture was cooled to room temperature, and added to a mixture of THF and H O. The organic layer was separated, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography to obtain a compound R (15 g, 86%). [158] MS: [M] = 143.
[159] <Preparation Example 19> Preparation of Compound S [160] Under N atmosphere, 1,5-diboronate naphthalene (6.65 g, 17.5 mmol),
2,6-dibromophenyl (10 g, 35.0 mmol), Pd(PPh ) (1.0 g, 0.87mmol) were added to a 2 M K CO aqueous solution (20 mL) and THF (200 mL), and refluxed under stirring for about 24 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the organic layer was separated from the reaction mixture. The organic layer was dried over magnesium sulfate, and purified by column chro-
matography to obtain a compound S (2.8g, 30%). [161] MS: [M+H]+ = 538. [162] <Preparation Example 20> Preparation of Compound T
[163] Aniline (10 ml, 109.74 mmol) and 1-bromopyrene (30.84 g, 109.7 mmol) were dissolved in 300 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 1.26 g, 2.20 mmol), 50 wt% of tri-?-butylphosphine (1.30 ml, 3.29 mmol)
2 and sodium ?-butoxide (21.09 g, 219.5 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound T (18.3 g, yield 56%). [164] MS: [M+H]+ = 298.
[165] <Preparation Example 21> Preparation of Compound U [166] Aniline (10 ml, 109.74 mmol) and 1-bromoperylene (36.33 g, 109.7 mmol) were dissolved in 300 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 1.26 g, 2.20 mmol), 50 wt% of tri-?-butylphosphine (1.30 ml, 3.29 mmol)
2 and sodium ?-butoxide (21.09 g, 219.5 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound U (20 g, yield 56%). [167] MS: [M+H]+ = 331.
[168] <Preparation Example 22> Preparation of Compound V [169] Under nitrogen atmosphere, 4.00 g of 4-chlorobiphenyl-N,N-diphenylamine (11.2 mmol) and 1.13 ml of aniline (12.4 mmol) were dissolved in 100 ml of toluene. Then, sodium ?-butoxide (2.70 g, 28.1 mmol), bis(dibenzylidene-acetone)palladium (0) (0.13 g, 0.23 mmol), and 50 wt% of a tri-?-butylphosphine toluene solution (0.17 ml, 0.34 mmol) were added thereto, and refluxed under nitrogen atmosphere for 5 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound V (3.8 g, yield 81%).
[170] MS: [M+H] + = 412.
[171] <Preparation Example 23> Preparation of Compound W [172] Under nitrogen atmosphere, 8.80 g of 4-chlorobiphenyl-N,N-diphenylamine (24.7
mmol) and 6.28 g of 4-aminobiphenyl (37.1 mmol) were dissolved in 200 ml of toluene. Then, sodium ?-butoxide (5.94 g, 61.8 mmol), bis(dibenzylidene-acetone)palladium (0) (0.43 g, 0.74 mmol), and 50 wt% of a tri- 1 - butylphosphine toluene solution (0.61 ml, 1.24 mmol) were added thereto, and refluxed under nitrogen atmosphere for 5 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound W (7.0 g, yield 58%).
[173] MS: [M+H]+= 489.
[174] <Preparation Example 24> Preparation of Compound X
[175] Under nitrogen atmosphere, 6.28 g of 4-aminobiphenyl (37.1 mmol), 8.12 g of
4-chlorophenyl-N,N-(l-naphthyl)phenylamine (24.7 mmol) were dissolved in 300 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 1.26 g, 2.20 mmol), 50 wt% of tri-?-butylphosphine (1.30 ml, 3.29 mmol) and sodium ?-butoxide (21.09 g, 219.5 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n- hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound X (6.39 g, yield 56%).
[176] MS: [M+H]+ = 462.
[177] <Preparation Example 25> Preparation of Compound Y
[178] 1-Aminonaphthalene (16.37 g, 109.74 mmol) and the compound H prepared in Preparation Example 8 (34.5 g, 109.7 mmol) were dissolved in 300 ml of toluene. Then, bis(dibenzylidene-acetone)palladium (0) (Pd(dba) , 1.26 g, 2.20 mmol), 50 wt% of tri-?-butylphosphine (1.30 ml, 3.29 mmol) and sodium ?-butoxide (21.09 g, 219.5 mmol) were added thereto, and refluxed under nitrogen atmosphere for 2 hrs. Distilled water was added to the reaction solution to terminate the reaction. The organic layer was extracted, and separated by column chromatography using n-hexane/THF (10/1), stirred in pet. Ether, and dried under vacuum to obtain a compound Y (23 g, yield 56%).
[179] MS: [M+H]+ = 377.
[183] <Example 1> Preparation of Compound 2-1
[181] Under nitrogen atmosphere, the compound A prepared in Preparation Example 1 (2.4 g, 8.5 mmol), the compound R prepared in Preparation Example 18 (2.9 g, 20.4 mmol), Pd(dba) (0.097 g, 0.17 mmol), P(t-Bu) (0.05 g, 0.255 mmol) and sodium t -
2 3
butoxide (2.45 g, 25.5 mmol) were dissolved in toluene (100 rnL), and refluxed for 2 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the reaction mixture was added to a mixture of THF and H O. The organic layer was separated, dried over MgSO , and concentrated. The residue was purified by column
4 chromatography to obtain a compound 2-1 (3.19 g, 62%). [182] MS: [M] = 606. [183] <Example 2> Preparation of Compound 2-6
[184] Under nitrogen atmosphere, the compound A prepared in Preparation Example 1 (2.4 g, 8.5 mmol), the compound P prepared in Preparation Example 16 (5.83 g, 20.4 mmol), Pd(dba) (0.097 g, 0.17 mmol), P(t-Bu) (0.05 g, 0.255 mmol) and sodium t -
2 3 butoxide (2.45 g, 25.5 mmol) were dissolved in toluene (100 mL), and refluxed for 2 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the reaction mixture was added to a mixture of THF and H O. The organic layer was separated, dried over MgSO , and concentrated. The residue was purified by column
4 chromatography to obtain a compound 2-6 (3.64 g, 60%). [185] MS: [M] = 696. [186] <Example 3> Preparation of Compound 2-12
[187] Under nitrogen atmosphere, the compound A prepared in Preparation Example 1 (2.4 g, 8.5 mmol), the compound H prepared in Preparation Example 8 (6.43 g, 20.4 mmol), Pd(dba) (0.097 g, 0.17 mmol), P(t-Bu) (0.05 g, 0.255 mmol) and sodium t -
2 3 butoxide (2.45 g, 25.5 mmol) were dissolved in toluene (100 mL), and refluxed for 2 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the reaction mixture was added to a mixture of THF and H O. The organic layer was separated, dried over MgSO , and concentrated. The residue was purified by column
4 chromatography to obtain a compound 2-12 (4.29 g, 65%). [188] MS: [M] = 778. [189] <Example 4> Preparation of Compound 2-52
[190] Under nitrogen atmosphere, the compound B prepared in Preparation Example 2
(3.07 g, 8.5 mmol), the compound J prepared in Preparation Example 10 (5.00 g, 20.4 mmol), Pd(dba) (0.097 g, 0.17 mmol), P(t-Bu) (0.05 g, 0.255 mmol) and sodium t -
2 3 butoxide (2.45 g, 25.5 mmol) were dissolved in toluene (100 mL), and refluxed for 2 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the reaction mixture was added to a mixture of THF and H O. The organic layer was separated, dried over MgSO , and concentrated. The residue was purified by column
4 chromatography to obtain a compound 2-52 (3.64 g, 60%).
[191] MS: [M] = 690.
[192] <Example 5> Preparation of Compound 3-52
[193] A Compound 3-52 (3.64 g, 60%) was obtained in the same manner as in Example 4, except that the compound F (3.07 g, 8.5 mmol) prepared in Preparation Example 6 was used instead of compound B (3.07 g, 8.5mmol) prepared in Preparation Example 2 in Example 4.
[194] MS: [M] = 690.
[195] <Example 6> Preparation of Compound 4-52
[196] A Compound 4-52 (3.64 g, 60%) was obtained in the same manner as in Example 4, except that the compound D (3.07 g, 8.5 mmol) prepared in Preparation Example 4 was used instead of compound B (3.07 g, 8.5mmol) prepared in Preparation Example 2 in Example 4.
[197] MS: [M] = 690.
[198] <Example 7> Preparation of Compound 2-64
[199] A Compound 2-64 (4.5 g, 62%) was obtained in the same manner as in Example 3, except that the compound B (3.07 g, 8.5 mmol) prepared in Preparation Example 2 was used instead of compound A (2.43 g, 8.5 mmol) prepared in Preparation Example 1 in Example 3.
[200] MS: [M] = 854.
[201] <Example 8> Preparation of Compound 2-68
[202] A Compound 2-68 (4.01 g, 60%) was obtained in the same manner as in Example 3, except that the compound T (6.CB g, 20.4 mmol) prepared in Preparation Example 20 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 4.
[203] MS: [M] = 786.
[204] <Example 9> Preparation of Compound 2-70
[205] A Compound 2-70 (3.77 g, 50%) was obtained in the same manner as in Example 4, except that the compound U (7.00 g, 20.4 mmol) prepared in Preparation Example 21 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 4.
[206] MS: [M] = 886.
[207] <Example 10> Preparation of Compound 2-78
[2C8] Under nitrogen atmosphere, the compound B prepared in Preparation Example 2
(3.07 g, 8.5 mmol), the compound M prepared in Preparation Example 13 (6.56 g, 20.4 mmol), Pd(dba) (0.097 g, 0.17 mmol), P(t-Bu) (0.05 g, 0.255 mmol) and sodium t -
2 3
butoxide (2.45 g, 25.5 mmol) were dissolved in toluene (150 rnL), and refluxed for 2 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the reaction mixture was added to a mixture of THF and H O. The organic layer was separated, dried over MgSO , and concentrated. The residue was purified by column
4 chromatography to obtain a compound 2-78 (4.65 g, 65%). [209] MS: [M] = 842. [210] <Example 11> Preparation of Compound 3-78
[211] A Compound 3-78 (3.64 g, 60%) was obtained in the same manner as in Example 10, except that the compound F (3.07 g, 8.5 mmol) prepared in Preparation Example 6 was used instead of compound B (3.07 g, 8.5 mmol) prepared in Preparation Example 2 in Example 10.
[212] MS: [M] = 842.
[213] <Example 12> Preparation of Compound 4-78
[214] A Compound 4-78 (3.64 g, 60%) was obtained in the same manner as in Example 10, except that the compound D (3.07 g, 8.5 mmol) prepared in Preparation Example 4 was used instead of compound B (3.07 g, 8.5 mmol) prepared in Preparation Example 2 in Example 10.
[215] MS: [M] = 842.
[216] <Example 13> Preparation of Compound 2-104
[217] Under nitrogen atmosphere, the compound C prepared in Preparation Example 3
(2.96 g, 8.5 mmol), the compound J prepared in Preparation Example 10 (5.00 g, 20.4 mmol), Pd(dba) (0.097 g, 0.17 mmol), P(t-Bu) (0.05 g, 0.255 mmol) and sodium t - butoxide (2.45 g, 25.5 mmol) were dissolved in toluene (150 mL), and refluxed for 2 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the reaction mixture was added to a mixture of THF and H O. The organic layer was separated, dried over MgSO , and concentrated. The residue was purified by column chromatography to obtain a compound 2-104 (4.23 g, 65%).
[218] MS: [M] = 766.
[219] <Example 14> Preparation of Compound 2-113
[220] Under nitrogen atmosphere, the compound C prepared in Preparation Example 3
(2.96 g, 8.5 mmol), the compound M prepared in Preparation Example 13 (6.56 g, 20.4 mmol), Pd(dba) (0.097 g, 0.17 mmol), P(t-Bu) (0.05 g, 0.255 mmol) and sodium t - butoxide (2.45 g, 25.5 mmol) were dissolved in toluene (150 mL), and refluxed for 2 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the reaction mixture was added to a mixture of THF and H O. The organic layer was
separated, dried over MgSO , and concentrated. The residue was purified by column chromatography to obtain a compound 2-113 (5.07 g, 65%). [221] MS: [M] = 918.
[222] <Example 15> Preparation of Compound 2-119 [223] A Compound 2-119 (4.39 g, 60%) was obtained in the same manner as in Example
13, except that the compound T (6.CB g, 20.4 mmol) prepared in Preparation Example
20 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 13.
[224] MS: [M] = 862.
[225] <Example 16> Preparation of Compound 2-121
[226] A Compound 2-121 (4.CB g, 50%) was obtained in the same manner as in Example
13, except that the compound U (7.00 g, 20.4 mmol) prepared in Preparation Example
21 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 13.
[227] MS: [M] = 962.
[228] <Example 17> Preparation of Compound 2-125
[229] A Compound 2-125 (6.CB g, 65%) was obtained in the same manner as in Example 13, except that the compound V (8.41 g, 20.4 mmol) prepared in Preparation Example
22 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 13.
[230] MS: [M] = 1100.
[231] <Example 18> Preparation of Compound 2-127
[232] A Compound 2-127 (6.12 g, 60%) was obtained in the same manner as in Example 13, except that the compound X (9.44 g, 20.4 mmol) prepared in Preparation Example
24 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 13.
[233] MS: [M] = 1200.
[234] <Example 19> Preparation of Compound 2-131
[235] A Compound 2-131 (5.25 g, 60%) was obtained in the same manner as in Example 13, except that the compound Y (7.70 g, 20.4 mmol) prepared in Preparation Example
25 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 13.
[236] MS: [M] = 1030.
[237] <Example 20> Preparation of Compound 2-155
[238] Under nitrogen atmosphere, the compound S prepared in Preparation Example 19
(4.58 g, 8.5 mmol), the compound J prepared in Preparation Example 10 (5.00 g, 20.4 mmol), Pd(dba) (0.097 g, 0.17 mmol), P(t-Bu) (0.05 g, 0.255 mmol) and sodium t - butoxide (2.45 g, 25.5 mmol) were dissolved in toluene (150 mL), and refluxed for 2 hrs. After completion of the reaction, the mixture was cooled to room temperature, and the reaction mixture was added to a mixture of THF and H O. The organic layer was separated, dried over MgSO , and concentrated. The residue was purified by column chromatography to obtain a compound 2-155 (4.78 g, 65%).
[239] MS: [M] = 866.
[240] <Example 21> Preparation of Compound 2-179
[241] A Compound 2-179 (5.19 g, 60%) was obtained in the same manner as in Example
13, except that the compound M (6.56 g, 20.4 mmol) prepared in Preparation Example 13 was used instead of compound J (5.00 g, 20.4 mmol) prepared in Preparation Example 10 in Example 13.
[242] MS: [M] = 1018.
[243] <Experimental Example 1>
[244] A glass substrate (Corning 7059 glass), on which a thin film of ITO (indium tin oxide) was coated to a thickness of 1,000 A, was immersed in distilled water having a detergent dissolved therein to wash the substrate with ultrasonic waves. The detergent as used herein was a product commercially available from Fisher Co. and the distilled water was one which had been twice filtered by using a filter commercially available from Millipore Co. ITO was washed for 30 minutes, and then washing with ultrasonic waves was repeated twice for 10 minutes by using distilled water. After the completion of washing with distilled water, washing with ultrasonic waves was carried out by using solvents such as isopropyl alcohol, acetone and methanol. The resultant product was dried, and then transported to a plasma washing machine. The substrate was washed for 5 minutes using an oxygen plasma, and then transported to a vacuum depositing machine. [245] On the ITO electrode,
3,6-bis-2-naphthylphenylamino-N-[4-(2-naphthylphenyl)aminophenyl]carbazole (800 A), and 4,4'-bis[N-(l-naphthyl)-N-phenyl amino]biphenyl (NPB) (300 A) were sequentially deposited to form a hole injecting layer and a hole transporting layer, respectively. The compound 2-1 prepared in Example 1 (2 wt%) was deposited thereon with the following compound Z (300 A) to form a light emitting layer, and then 9,10-bis-2-naphthyl-2-[4-(N-phenylbenzoimidazoyl)phenyl]anthracene (300 A) was coated by thermal vacuum deposition to form an electron transporting layer.
[246] lithium fluoride pF) and aluminum were sequentially deposited on the electron transporting layer to thicknesses of 12 A and 2,000 A, respectively, to form a cathode, thereby obtaining an organic light emitting device.
[247] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 A/sec and the deposition rate of lithium fluoride on the cathode was maintained at 0.3 A/sec and the deposition rate of aluminum was maintained at 2 A/
7 -8 sec. The degree of vacuum upon deposition was maintained at 2 x 10 to 5 x 10 torr. [248] When a forward electric field of 7.8 V was applied to the organic light emitting device as prepared above, blue light emission of 4.9 cd/A was observed with x =
0.170, and y = 0.150 based on the 1931 CIE color coordinate at a current density of
100 mA/cnf.
[251] <Experimental Example 2>
[252] An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound 2-68 prepared in Example 8 was used instead of the compound 2-1 in Experimental Example 1.
[253] When a forward electric field of 7.9 V was applied to the organic light emitting device as prepared above, blue light emission of 4.7 cd/A was observed with x = 0.170, and y = 0.151 based on the 1931 CIE color coordinate at a current density of 100 mA/cnf.
[254] <Experimental Example 3>
[255] An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound 2-70 prepared in Example 9 was used instead of the compound 2-1 in Experimental Example 1.
[256] When a forward electric field of 7.7 V was applied to the organic light emitting device as prepared above, blue light emission of 4.8 cd/A was observed with x = 0.171, and y = 0.153 based on the 1931 CIE color coordinate at a current density of 100 mA/cnf.
[257] Experimental Example 4>
[258] An organic light emitting device was prepared in the same manner as in Ex-
perimental Example 1, except that the compound 2-119 prepared in Example 15 was used instead of the compound 2-1 in Experimental Example 1.
[259] When a forward electric field of 7.7 V was applied to the organic light emitting device as prepared above, blue light emission of 4.9 cd/A was observed with x = 0.171, and y = 0.153 based on the 1931 CIE color coordinate at a current density of 100 mA/cnf.
[260] <Experimental Example 5>
[261] An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound 2-121 prepared in Example 16 was used instead of the compound 2-1 in Experimental Example 1.
[262] When a forward electric field of 7.8 V was applied to the organic light emitting device as prepared above, blue light emission of 4.8 cd/A was observed with x = 0.172, and y = 0.153 based on the 1931 CIE color coordinate at a current density of 100 mA/cnf.
[263] <Experimental Example 6>
[264] An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound 2-179 prepared in Example 21 was used instead of the compound 2-1 in Experimental Example 1.
[265] When a forward electric field of 7.9 V was applied to the organic light emitting device as prepared above, blue light emission of 4.9 cd/A was observed with x = 0.173, and y = 0.152 based on the 1931 CIE color coordinate at a current density of 100 mA/cnf.
[266] Experimental Example 7>
[267] On the ITO electrode thus prepared, hexanitrile hexaazatriphenylene (hereinafter, referred to as HAT) of the following Formula was coated to thicknesses of 500 by thermal vacuum deposition, so as to form anode comprising an ITO conducting layer and an n-type organic material.
[268] [HAT]
[271] [Electron transporting layer material]
[273] On the electron transporting layer, lithium fluoride pF) and aluminum were sequentially vacuum-deposited to a thickness of 12 A and 2,000 A, respectively, to form a cathode.
[274] In the above process, the deposition rate of the organic material was maintained at
0.3 to 0.8 A/sec and the deposition rates of lithium fluoride and aluminum of the cathode were maintained at 0.3 A/sec and 1.5 to 2.5 A/sec, respectively. The vacuum degree during deposition was maintained at 1 x 10 - 3 x 10 torr.
[275] An electric field of 4.54 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of 1.89 ImAV. light emitting by the device at the above drive voltage indicates that the compound 2-52 of Example 4 formed between the hole injecting layer and light emitting layer functions to transport a hole.
[276] <Experimental Example 8>
[277] An organic light emitting device was prepared in the same manner as in Experimental Example 7, except that the compound 3-78 prepared in Example 11 was used instead of the compound 2-52 used as a hole transporting layer in Experimental Example 7.
[278] An electric field of 4.52 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of 1.91 ImAV. light emitting by the device at the above drive voltage indicates that the compound 3-78 formed between the thin film on the substrate and hole transporting
layer functions to transport a hole. [279] <Experimental Example 9>
[283] An organic light emitting device was prepared in the same manner as in Experimental Example 7, except that the compound 4-78 prepared in Example 12 was used instead of the compound 2-52 used as a hole transporting layer in Experimental Example 7.
[281] An electric field of 4.53 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of 1.90 ImAV. light emitting by the device at the above drive voltage indicates that the compound 4-78 formed between the thin film on the substrate and hole transporting layer functions to transport a hole.
[282] <Experimental Example 10>
[283] An organic light emitting device was prepared in the same manner as in Experimental Example 7, except that the compound 2-104 prepared in Example 13 was used instead of the compound 2-52 used as a hole transporting layer in Experimental Example 7.
[284] An electric field of 4.50 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of 1.89 ImAV. light emitting by the device at the above drive voltage indicates that the compound 2-104 formed between the thin film on the substrate and hole transporting layer functions to transport a hole.
[285] Experimental Example 11>
[286] An organic light emitting device was prepared in the same manner as in Experimental Example 7, except that the compound 2-113 prepared in Example 14 was used instead of the compound 2-52 used as a hole transporting layer in Experimental Example 7.
[287] An electric field of 4.31 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of 1.98 ImAV. light emitting by the device at the above drive voltage indicates that the compound 2-113 formed between the thin film on the substrate and hole transporting layer functions to transport a hole.
[288] Experimental Example 12>
[289] An organic light emitting device was prepared in the same manner as in Experimental Example 7, except that the compound 2-125 prepared in Example 17 was used instead of the compound 2-52 used as a hole transporting layer in Experimental
Example 7.
[290] An electric field of 4.52 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of 1.91 ImAV. light emitting by the device at the above drive voltage indicates that the compound 2-125 formed between the thin film on the substrate and hole transporting layer functions to transport a hole.
[291] <Experimental Example 13>
[292] An organic light emitting device was prepared in the same manner as in Experimental Example 7, except that the compound 2-127 prepared in Example 18 was used instead of the compound 2-52 used as a hole transporting layer in Experimental Example 7.
[293] An electric field of 4.53 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of
1.90 ImAV. light emitting by the device at the above drive voltage indicates that the compound 2-127 formed between the thin film on the substrate and hole transporting layer functions to transport a hole.
[294] <Experimental Example 14>
[295] An organic light emitting device was prepared in the same manner as in Experimental Example 7, except that the compound 2-131 prepared in Example 19 was used instead of the compound 2-52 used as a hole transporting layer in Experimental Example 7.
[296] An electric field of 4.31 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of 1.96 ImAV. light emitting by the device at the above drive voltage indicates that the compound 2-131 formed between the thin film on the substrate and hole transporting layer functions to transport a hole.
[297] Experimental Example 15>
[298] An organic light emitting device was prepared in the same manner as in Experimental Example 7, except that the compound 2-155 prepared in Example 20 was used instead of the compound 2-52 used as a hole transporting layer in Experimental Example 7.
[299] An electric field of 4.52 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of
1.91 ImAV. light emitting by the device at the above drive voltage indicates that the compound 2-155 formed between the thin film on the substrate and hole transporting
layer functions to transport a hole. [300] <Comparative Experimental Example 1>
[301] An organic light emitting device was prepared in the same manner as in Experimental Example 7, except that a commercial NPB material of the following Formula was used instead of the compound 2-52 used as a hole transporting layer in Experimental Example 7.
[302] [NPB]
[304] An electric field of 4.82 V was observed in the above prepared device at a forward current density of 100 mA/cnf, and spectrum was observed with a light efficiency of
1.87 ImAV. [305] The diamine derivative according to the present invention was found to exhibit effects of lower operating voltage and increased efficiency of an organic electronic device.
Claims
[Formula 1]
6 20 with one or more groups selected from the group consisting of a C ~ C alfyl group, a C ~ C alkenyl group, a C ~ C alWnyl group, a C ~ C cycloaltod
2 20 2 20 3 20 group, a C 2 ~ C 20 heterocycloalk .y/ l goroujp-, a C 6 ~ C 20 aryl group and a C 5 ~ C 20 heteroaryl group; or a C ~ C heteroarylene group unsubstituted or substituted with one or more groups selected from the group consisting of a C ~ C alfod
1 20 group, a C ~ C alkenyl group, a C ~ C alkynyl group, a C ~ C cycloalkyl
2 20 2 20 3 20 group, a C ~ C heterocycloalkyl group, a C ~ C aryl group and a C ~ C
2 20 6 20 5 20 heteroaryl group; and
ArI, Ar2, Ar3and Ar4 are same or different from each other, and are each independently hydrogen, a C ~ C aryl group unsubstituted or substituted with
6 30 halogen, CN, NO , a C ~ C alkyl group, a C ~ C alkoxy group, a C ~ C
2 1 20 1 20 6 20 aryl group, a C 5 ~ C 20 heteroaryl group, a C 6 ~ C 20 aryl amine g σrouxp-, a C 6 ~ C 20 aryl thiophene group, a C ~ C cycloalkyl group, -OR, ^SR, ^SeR, -TeR, -BRR', -AlRR', -SRR'R", -GeRR1R", or -SnRR1R"; a C ~ C heterocyclic group
5 20 comprising O, N or S; or a condensed ring formed by fusing a C ~ C alkylene
4 20 group with a C ~ C aryl group, wherein R, R', and R" are same or different
6 20 from each other, and are each independently hydrogen, a C ~ C alkyl group, a C 3 - C 20 cycloalky ./ l gorouxp-, a C 6 ~ C 20 aryl group or a C 5 ~ C 20 heterocyclic group.
[2] The diamine derivative according to claim 1, wherein Formula 1 is represented by any one of the following Formulae 2 to 6: [Formula 2]
[3] The diamine derivative according to claim 1, wherein Ll and L2 of Formula 1 are same or different from each other, and are each independently a direct bond, or selected from the group consisting of a phenylene group and a naphthylene group.
[4] The diamine derivative according to claim 1, wherein ArI and Ar3 of Formula 1 are same or different from each other, and are each independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and
a phenyl group substituted with ^SRR1R" or -GeRR1R", wherein R, R', and R" are same or different from each other, and are each independently hydrogen, a C ~ C alkyl group, a C ~ C cycloalkyl group, a C ~ C aryl group or a C ~ C
20 3 20 J o r 6 20 5 20 heterocyclic group.
[5] The diamine derivative according to claim 1, wherein Ar2 and Ar4 of Formula 1 are same or different from each other, and are each independently selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a pherylenyl group, a phenyl group substituted with ^SRR1R" or -GeRR1R", a C ~ C heterocyclic group
5 20 comprising S, a C ~ C aryl amine group, and a C ~ C aryl group, wherein R,
6 20 6 20
R', and R" are same or different from each other, and are each independently hydrogen, a C ~ C ahtyl group, a C ~ C cycloahtyl group, a C ~C aryl
1 20 3 20 6 20 group or a C ~ C heterocyclic group.
[6] The diamine derivative according to claim 1, wherein Ll, L2, ArI, Ar2, Ar3, and
Ar4 of Formula 1 are selected from the groups of the following Table 1. [Table 1]
[7] An organic electronic device comprising a first electrode, a second electrode and
one or more organic material layers interposed therebetween, wherein at least one organic material layer comprises the diamine derivative of any one of claims l to 6. [8] The organic electronic device according to claim 7, wherein the organic electronic device has a normal structure prepared by sequentially laminating an anode, one or more organic material layers, and a cathode on a substrate. [9] The organic electronic device according to claim 7, wherein the organic el ectronic device has an inverted structure prepared by sequentially laminating a cathode, one or more organic material layers, and an anode on a substrate. [10] The organic electronic device according to claim 7, wherein the organic material layer comprises at least one of a hole injecting layer, a hole transporting layer, and a hole injecting and hole transporting layer, and at least one of the layers comprises the diamine derivative of Formula 1. [11] The organic electronic device according to claim 7, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the diamine derivative of Formula 1. [12] The organic electronic device according to claim 7, wherein the organic material layer comprises an electron transporting layer, and the electron transporting layer comprises the diamine derivative of Formula 1. [13] The organic electronic device according to claim 7, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic photovoltaic cell, an organic photoconductor (OPC) and an organic transistor.
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| CN200880013651.7A CN101668730B (en) | 2007-04-26 | 2008-04-25 | Diamine derivative and use the organic electronic device of this derivant |
| US12/451,063 US8026514B2 (en) | 2007-04-26 | 2008-04-25 | Diamine derivatives and organic electronic device using the same |
| JP2010506071A JP5373769B2 (en) | 2007-04-26 | 2008-04-25 | Novel diamine derivative and organic electronic device using the same |
| EP08753194.3A EP2139846B1 (en) | 2007-04-26 | 2008-04-25 | New diamine derivatives and organic electronic device using the same |
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| US (1) | US8026514B2 (en) |
| EP (1) | EP2139846B1 (en) |
| JP (2) | JP5373769B2 (en) |
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| US20110163300A1 (en) * | 2010-01-06 | 2011-07-07 | National Chiao Tung University | Organic light-emitting material, organic light-emitting element using the same and method of forming the same |
| CN102257097A (en) * | 2008-12-18 | 2011-11-23 | 东友精细化工有限公司 | Asymmetrical aryl amine derivative for organic electroluminescence devices, method for preparing same, organic thin film for organic electroluminescence devices and organic electroluminescence device using same |
| EP2776386B1 (en) * | 2011-11-11 | 2019-11-20 | Merck Patent GmbH | Process for producing arylamines |
| US11968887B2 (en) | 2019-11-27 | 2024-04-23 | Samsung Display Co., Ltd. | Organic electroluminescence device and diamine compound for organic electroluminescence device |
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| EP2139846B1 (en) * | 2007-04-26 | 2016-09-07 | LG Chem, Ltd. | New diamine derivatives and organic electronic device using the same |
| WO2013169918A1 (en) * | 2012-05-08 | 2013-11-14 | Carl Wagner | Naphthyl-containing compounds for light-emitting devices |
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Also Published As
| Publication number | Publication date |
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| EP2139846A4 (en) | 2011-08-24 |
| TW200904782A (en) | 2009-02-01 |
| EP2139846A1 (en) | 2010-01-06 |
| TWI478898B (en) | 2015-04-01 |
| CN101668730A (en) | 2010-03-10 |
| JP2010525054A (en) | 2010-07-22 |
| US8026514B2 (en) | 2011-09-27 |
| CN101668730B (en) | 2016-09-21 |
| EP2139846B1 (en) | 2016-09-07 |
| JP2014005283A (en) | 2014-01-16 |
| KR20080096440A (en) | 2008-10-30 |
| US20100187504A1 (en) | 2010-07-29 |
| KR101012578B1 (en) | 2011-02-07 |
| JP5373769B2 (en) | 2013-12-18 |
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