KR20070011185A - 합성 방법 - Google Patents
합성 방법 Download PDFInfo
- Publication number
- KR20070011185A KR20070011185A KR1020060067953A KR20060067953A KR20070011185A KR 20070011185 A KR20070011185 A KR 20070011185A KR 1020060067953 A KR1020060067953 A KR 1020060067953A KR 20060067953 A KR20060067953 A KR 20060067953A KR 20070011185 A KR20070011185 A KR 20070011185A
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- unsubstituted
- anthracene
- carbon atoms
- aryl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 230000008569 process Effects 0.000 title description 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims abstract description 55
- 150000001454 anthracenes Chemical class 0.000 claims abstract description 39
- -1 aryl boric acid Chemical compound 0.000 claims abstract description 35
- 239000004327 boric acid Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 230000002140 halogenating effect Effects 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Chemical group 0.000 claims abstract description 4
- 150000002367 halogens Chemical group 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- HHQJWDKIRXRTLS-UHFFFAOYSA-N n'-bromobutanediamide Chemical compound NC(=O)CCC(=O)NBr HHQJWDKIRXRTLS-UHFFFAOYSA-N 0.000 claims description 5
- DCMWJXWYTURQIM-UHFFFAOYSA-N naphthalen-2-yloxyboronic acid Chemical compound C1=CC=CC2=CC(OB(O)O)=CC=C21 DCMWJXWYTURQIM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 62
- 230000002194 synthesizing effect Effects 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 62
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- 229910052751 metal Inorganic materials 0.000 description 23
- 239000002184 metal Substances 0.000 description 23
- 230000005525 hole transport Effects 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000872 buffer Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000002739 metals Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- WBPXZSIKOVBSAS-UHFFFAOYSA-N 2-tert-butylanthracene Chemical compound C1=CC=CC2=CC3=CC(C(C)(C)C)=CC=C3C=C21 WBPXZSIKOVBSAS-UHFFFAOYSA-N 0.000 description 4
- BWFOVZDGMFZPFX-UHFFFAOYSA-N 9,10-dibromo-2-tert-butylanthracene Chemical compound C1=CC=CC2=C(Br)C3=CC(C(C)(C)C)=CC=C3C(Br)=C21 BWFOVZDGMFZPFX-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 150000001629 stilbenes Chemical class 0.000 description 4
- 235000021286 stilbenes Nutrition 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 229920000128 polypyrrole Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- MVIXNQZIMMIGEL-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MVIXNQZIMMIGEL-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BBDFECYVDQCSCN-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-[4-(n-(4-methoxyphenyl)anilino)phenyl]-n-phenylaniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(OC)=CC=1)C1=CC=CC=C1 BBDFECYVDQCSCN-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical compound C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JUMBSPQABSHVMN-UHFFFAOYSA-N (4-tert-butylphenoxy)boronic acid Chemical compound CC(C)(C)C1=CC=C(OB(O)O)C=C1 JUMBSPQABSHVMN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 description 1
- VVJKFZOOFYHKRU-UHFFFAOYSA-N 2-tert-butyl-9,10-diphenylanthracene Chemical compound C=12C=CC=CC2=C(C=2C=CC=CC=2)C2=CC(C(C)(C)C)=CC=C2C=1C1=CC=CC=C1 VVJKFZOOFYHKRU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- MBPRTQOJXVLLOX-UHFFFAOYSA-N 3-chloro-n,n-bis[4-[4-(n-(4-methylphenyl)anilino)phenyl]phenyl]aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(C)=CC=1)C=1C=C(Cl)C=CC=1)C1=CC=CC=C1 MBPRTQOJXVLLOX-UHFFFAOYSA-N 0.000 description 1
- JTYQCTFXIFJEJQ-UHFFFAOYSA-N 3-chloro-n-[4-[4-(n-[4-[4-(n-(3-chlorophenyl)anilino)phenyl]phenyl]-4-methylanilino)phenyl]phenyl]-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(Cl)C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(Cl)C=CC=2)C=C1 JTYQCTFXIFJEJQ-UHFFFAOYSA-N 0.000 description 1
- YSHILDHWLYZFRM-UHFFFAOYSA-N 3-methyl-n-[4-[4-(4-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]anilino)phenyl]phenyl]-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=C(C)C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=C1 YSHILDHWLYZFRM-UHFFFAOYSA-N 0.000 description 1
- HNGFXAZKPAMUBA-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 HNGFXAZKPAMUBA-UHFFFAOYSA-N 0.000 description 1
- QZBHQKMPXHETKV-UHFFFAOYSA-N 3-methyl-n-[4-[4-[n-(3-methylphenyl)-4-[4-(n-(3-methylphenyl)anilino)phenyl]anilino]phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 QZBHQKMPXHETKV-UHFFFAOYSA-N 0.000 description 1
- AHDTYXOIJHCGKH-UHFFFAOYSA-N 4-[[4-(dimethylamino)-2-methylphenyl]-phenylmethyl]-n,n,3-trimethylaniline Chemical compound CC1=CC(N(C)C)=CC=C1C(C=1C(=CC(=CC=1)N(C)C)C)C1=CC=CC=C1 AHDTYXOIJHCGKH-UHFFFAOYSA-N 0.000 description 1
- MEIBOBDKQKIBJH-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]-4-phenylcyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCC(CC1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MEIBOBDKQKIBJH-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- UMLCUVMYTCNXSI-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-[4-[4-(n-(4-methylphenyl)anilino)phenyl]phenyl]anilino)phenyl]phenyl]-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(C)=CC=1)C1=CC=CC=C1 UMLCUVMYTCNXSI-UHFFFAOYSA-N 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
Claims (20)
- 치환 또는 치환되지 않은 안트라센을 할로겐화제와 반응시켜 할로겐화된 안트라센을 생성하는 단계; 및상기 할로겐화된 안트라센을 아릴 붕산 또는 붕산 에스테르와 반응시켜 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 생성하는 단계를 포함하는 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제1 항에 있어서,상기 치환 또는 치환되지 않은 9,10-디아릴 안트라센은 2-터트-부틸-9,10-비스-(β-나프틸)안트라센인 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제1 항에 있어서,상기 치환 또는 치환되지 않은 9,10-디아릴 안트라센은 다음의 [화학식 1]로 표시되고:[화학식 1]여기서 R1과 R2 각각은 (1) 수소; (2) 약 1 내지 약 24개의 탄소 원자들을 포함하는 알킬 그룹; (3) 약 5 내지 약 20개의 탄소 원자들을 포함하는 치환되지 않은 아릴 또는 치환된 아릴; (4) 약 5 내지 약 24 개의 탄소 원자들을 포함하는 치환되지 않은 헤테로아릴 또는 치환된 헤테로아릴, 여기서 상기 탄소 원자들은 접합 헤테로 고리(fused heterocyclic ring)를 완성할 수 있다; (5) 약 1 내지 약 24 개의 탄소 원자들을 포함하는 알콕실, 아미노, 알킬 아미노, 또는 아릴 아미노; 그리고 (6) 할로겐 원자들로 구성되는 그룹으로부터 독립적으로 선택되고, 그리고 동일하거나 다른 R3와 R4는 그룹 (2), (3), (4)와 위에서 정의된 그룹 (5)의 아릴 아미노로 구성되는 그룹으로부터 개별적으로 선택될 수 있는 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제1 항에 있어서,상기 치환 또는 치환되지 않은 안트라센은 알킬 그룹들, 알킬렌 그룹들, 아릴 그룹들, 아릴렌 그룹들, 알콕시 그룹들, 아릴옥시 그룹들, 그리고 할로겐들로 구성되는 그룹으로부터 선택된 적어도 하나의 치환체로 치환되는 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제4 항에 있어서,상기 치환 또는 치환되지 않은 안트라센은 알킬 그룹으로 치환되는 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제5 항에 있어서,상기 알킬 그룹은 t-부틸 그룹인 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제1 항에 있어서,상기 할로겐화제는 N-브로모숙신아미드인 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제1 항에 있어서,상기 치환 또는 치환되지 않은 안트라센은 극성 액체의 존재하에서 할로겐화제와 반응되는 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제8 항에 있어서,상기 극성 액체는 디메틸포름아미드인 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제1 항에 있어서,상기 치환 또는 치환되지 않은 안트라센은 상온에서 3시간 동안 할로겐화제와 반응되는 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제1 항에 있어서,상기 할로겐화된 안트라센은 [화학식 2]로 표현되고,[화학식 2]여기서 R1과 R2 각각은 수소; 약 1 내지 약 24개의 탄소 원자들을 포함하는 알킬 그룹; 약 5 내지 약 20개의 탄소 원자들을 포함하는 치환되지 않은 아릴 또는 치환된 아릴; 약 5 내지 약 24 개의 탄소 원자들을 포함하는 치환되지 않은 헤테로 아릴 또는 치환된 헤테로아릴, 여기서 탄소 원자들은 접합 헤테로 고리(fused heterocyclic ring)를 완성할 수 있다; 약 1 내지 약 24개의 탄소 원자들을 포함하는 알콕실, 아미노, 알킬 아미노, 또는 아릴 아미노로 구성되는 그룹; 할로겐 원자들로부터 독립적으로 선택될 수 있고,여기서 X는 할로겐 원자이고,n은 약 1 내지 약 9의 정수인 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제1 항에 있어서,상기 아릴 붕산은 2-나프틸붕산인 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 할로겐화된 안트라센을 아릴 붕산 또는 붕산 에스테르와 반응시켜 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 생성하는 단계를 포함하는 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제14 항에 있어서,상기 할로겐화된 안트라센은 [화학식 2]로 표현되고:[화학식 2]여기서 R1과 R2 각각은 수소; 약 1 내지 약 24개의 탄소 원자들을 포함하는 알킬 그룹; 약 5 내지 약 20개의 탄소 원자들을 포함하는 치환되지 않은 아릴 또는 치환된 아릴; 약 5 내지 약 24 개의 탄소 원자들을 포함하는 치환되지 않은 헤테로아릴 또는 치환된 헤테로아릴, 여기서 탄소 원자들은 접합 헤테로 고리(fused heterocyclic ring)를 완성할 수 있다; 약 1 내지 약 24개의 탄소 원자들을 포함하 는 알콕실, 아미노, 알킬 아미노, 또는 아릴 아미노로 구성되는 그룹; 할로겐 원자들로부터 독립적으로 선택될 수 있고,여기서 X는 할로겐 원자이고,n은 약 1 내지 약 9의 정수인 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 제14 항에 있어서,상기 아릴 붕산은 2-나프틸붕산인 것을 특징으로 하는 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 조제하기 위한 방법.
- 치환 또는 치환되지 않은 9,10-디아릴 안트라센을 포함하는 발광층을 포함하고, 상기 치환 또는 치환되지 않은 9,10-디아릴 안트라센은 아릴 붕산을 [화학식 2]로 표시되는 할로겐화된 안트라센과 반응시키는 것에 의하여 조제되고,[화학식 2]여기서 R1과 R2 각각은 수소; 약 1 내지 약 24개의 탄소 원자들을 포함하는 알킬 그룹; 약 5 내지 약 20개의 탄소 원자들을 포함하는 치환되지 않은 아릴 또는 치환된 아릴; 약 5 내지 약 24 개의 탄소 원자들을 포함하는 치환되지 않은 헤테로아릴 또는 치환된 헤테로아릴, 여기서 탄소 원자들은 접합 헤테로 고리(fused heterocyclic ring)를 완성할 수 있다; 약 1 내지 약 24개의 탄소 원자들을 포함하는 알콕실, 아미노, 알킬 아미노, 또는 아릴 아미노로 구성되는 그룹; 할로겐 원자들로부터 독립적으로 선택될 수 있고,여기서 X는 할로겐 원자이고,n은 약 1 내지 약 9의 정수인 것을 특징으로 하는 전계발광 소자.
- 제18 항에 있어서,상기 치환 또는 치환되지 않은 9,10-디아릴 안트라센은 2-터트-부틸-9,10-비스-(β-나프틸)안트라센인 것을 특징으로 하는 전계발광 소자.
- 제18 항에 있어서,상기 할로겐화된 안트라센은 할로겐화제를 다음의 [화학식 1]로 표시되는 치환 또는 치환되지 않은 9,10-디아릴 안트라센과 반응시키는 것에 의하여 조제되고[화학식 1]여기서 R1과 R2 각각은 (1) 수소; (2) 약 1 내지 약 24개의 탄소 원자들을 포함하는 알킬 그룹; (3) 약 5 내지 약 20개의 탄소 원자들을 포함하는 치환되지 않은 아릴 또는 치환된 아릴; (4) 약 5 내지 약 24 개의 탄소 원자들을 포함하는 치환되지 않은 헤테로아릴 또는 치환된 헤테로아릴, 여기서 상기 탄소 원자들은 접합 헤테로 고리(fused heterocyclic ring)를 완성할 수 있다; (5) 약 1 내지 약 24 개의 탄소 원자들을 포함하는 알콕실, 아미노, 알킬 아미노, 또는 아릴 아미노; 그리고 (6) 할로겐 원자들로 구성되는 그룹으로부터 독립적으로 선택되고, 그리고 동일하거나 다른 R3와 R4는 그룹 (2), (3), (4)와 위에서 정의된 그룹 (5)의 아릴 아 미노로 구성되는 그룹으로부터 개별적으로 선택될 수 있는 것을 특징으로 하는 전계발광 소자.
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CN101628847B (zh) | 2002-08-23 | 2013-05-29 | 出光兴产株式会社 | 有机电致发光器件和蒽衍生物 |
JP2004179142A (ja) | 2002-09-30 | 2004-06-24 | Sanyo Electric Co Ltd | 発光素子 |
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JP2005043303A (ja) | 2003-07-25 | 2005-02-17 | Toyota Industries Corp | 水分・ガス検出方法、水分・ガスセンサ、当該センサを用いた水分・ガス検出装置、当該水分・ガスセンサ及び前記水分・ガス検出装置の保管方法並びに保管器 |
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US7138763B2 (en) * | 2003-11-14 | 2006-11-21 | Eastman Kodak Company | Organic electroluminescent devices having a stability-enhancing layer |
JP2005174700A (ja) | 2003-12-10 | 2005-06-30 | Toyota Industries Corp | 電界発光デバイス |
US20050245752A1 (en) | 2004-04-29 | 2005-11-03 | Eastman Kodak Company | Synthesis of unsymmetric anthracene compounds |
KR20060118913A (ko) * | 2005-05-17 | 2006-11-24 | 엘지전자 주식회사 | 호스트 물질 및 그 유기전계발광소자 |
US8766023B2 (en) * | 2005-07-20 | 2014-07-01 | Lg Display Co., Ltd. | Synthesis process |
-
2005
- 2005-07-20 US US11/184,775 patent/US7622619B2/en active Active
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2006
- 2006-06-28 DE DE102006029721A patent/DE102006029721B4/de not_active Revoked
- 2006-06-30 TW TW095124074A patent/TWI302162B/zh active
- 2006-07-18 GB GB0614245A patent/GB2428684B/en active Active
- 2006-07-19 FR FR0606559A patent/FR2888844B1/fr active Active
- 2006-07-20 JP JP2006197531A patent/JP4746492B2/ja active Active
- 2006-07-20 KR KR1020060067953A patent/KR100836497B1/ko active IP Right Grant
- 2006-07-20 CN CNA2006100994370A patent/CN1900031A/zh active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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KR100841417B1 (ko) * | 2006-10-31 | 2008-06-25 | 주식회사 대림화학 | 2,6-치환기를 갖는 9,10-디페닐안트라센 발광 화합물 및이를 발광재료로서 채용하고 있는 발광소자 |
KR100877344B1 (ko) * | 2007-08-10 | 2009-01-07 | (주)루디스 | 녹색/청색 형광 발광물질 및 이를 포함하는유기전계발광소자 |
Also Published As
Publication number | Publication date |
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JP2007023041A (ja) | 2007-02-01 |
FR2888844A1 (fr) | 2007-01-26 |
TW200704752A (en) | 2007-02-01 |
TWI302162B (en) | 2008-10-21 |
US20070020480A1 (en) | 2007-01-25 |
FR2888844B1 (fr) | 2014-08-08 |
GB2428684B (en) | 2010-02-10 |
US7622619B2 (en) | 2009-11-24 |
JP4746492B2 (ja) | 2011-08-10 |
CN1900031A (zh) | 2007-01-24 |
DE102006029721B4 (de) | 2008-02-07 |
GB2428684A (en) | 2007-02-07 |
GB0614245D0 (en) | 2006-08-30 |
KR100836497B1 (ko) | 2008-06-09 |
DE102006029721A1 (de) | 2007-04-05 |
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